TW200836629A - Insecticidal composition for seeds or harvested crops and method for using the same - Google Patents
Insecticidal composition for seeds or harvested crops and method for using the same Download PDFInfo
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- TW200836629A TW200836629A TW96148242A TW96148242A TW200836629A TW 200836629 A TW200836629 A TW 200836629A TW 96148242 A TW96148242 A TW 96148242A TW 96148242 A TW96148242 A TW 96148242A TW 200836629 A TW200836629 A TW 200836629A
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- alkyl
- base
- phenyl
- atom
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- 238000000034 method Methods 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 241000238631 Hexapoda Species 0.000 claims abstract description 8
- 230000006378 damage Effects 0.000 claims abstract description 4
- -1 benzynyl group Chemical group 0.000 claims description 739
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 572
- 229910052739 hydrogen Inorganic materials 0.000 claims description 227
- 125000005843 halogen group Chemical group 0.000 claims description 126
- 125000000217 alkyl group Chemical group 0.000 claims description 111
- 239000000460 chlorine Substances 0.000 claims description 99
- 125000001424 substituent group Chemical group 0.000 claims description 91
- 239000007789 gas Chemical group 0.000 claims description 85
- 125000003545 alkoxy group Chemical group 0.000 claims description 79
- 125000004429 atom Chemical group 0.000 claims description 79
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 74
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 74
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 68
- 125000000623 heterocyclic group Chemical group 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 64
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 63
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 60
- 229910052736 halogen Inorganic materials 0.000 claims description 57
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 53
- 229910052799 carbon Inorganic materials 0.000 claims description 50
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 50
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 47
- 125000004076 pyridyl group Chemical group 0.000 claims description 46
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 44
- 125000003282 alkyl amino group Chemical group 0.000 claims description 44
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 42
- 125000003277 amino group Chemical group 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 38
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 37
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 36
- 239000005864 Sulphur Substances 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- 125000005605 benzo group Chemical group 0.000 claims description 34
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 33
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 33
- 125000001544 thienyl group Chemical group 0.000 claims description 33
- 241000196324 Embryophyta Species 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 239000004575 stone Substances 0.000 claims description 31
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
- 125000001188 haloalkyl group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 27
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
- 125000000335 thiazolyl group Chemical group 0.000 claims description 26
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 25
- 125000002541 furyl group Chemical group 0.000 claims description 25
- 125000002971 oxazolyl group Chemical group 0.000 claims description 25
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 24
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 23
- 150000001721 carbon Chemical group 0.000 claims description 22
- 125000002883 imidazolyl group Chemical group 0.000 claims description 22
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000002923 oximes Chemical class 0.000 claims description 22
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 21
- 229910052707 ruthenium Inorganic materials 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 239000000843 powder Substances 0.000 claims description 20
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 20
- 239000002689 soil Substances 0.000 claims description 20
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 19
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 19
- 125000001425 triazolyl group Chemical group 0.000 claims description 19
- 241000607479 Yersinia pestis Species 0.000 claims description 18
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 18
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 18
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 18
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 18
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 18
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 17
- 125000002837 carbocyclic group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 17
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 17
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 17
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 15
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 15
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 14
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 14
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 14
- 238000003306 harvesting Methods 0.000 claims description 14
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 14
- 240000007594 Oryza sativa Species 0.000 claims description 13
- 235000007164 Oryza sativa Nutrition 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 235000009566 rice Nutrition 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 12
- 125000006612 decyloxy group Chemical group 0.000 claims description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004997 halocarbonyl group Chemical group 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- 150000003973 alkyl amines Chemical class 0.000 claims description 11
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 11
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 10
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical group O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 238000003958 fumigation Methods 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 10
- 125000004354 sulfur functional group Chemical group 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 229910001347 Stellite Inorganic materials 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 8
- 229910052797 bismuth Inorganic materials 0.000 claims description 7
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
- 150000004141 diterpene derivatives Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 7
- 229930192474 thiophene Natural products 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
- 206010036790 Productive cough Diseases 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 229930004069 diterpene Natural products 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 210000003802 sputum Anatomy 0.000 claims description 6
- 208000024794 sputum Diseases 0.000 claims description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
- 125000004149 thio group Chemical group *S* 0.000 claims description 6
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 5
- 244000241257 Cucumis melo Species 0.000 claims description 5
- 241000255925 Diptera Species 0.000 claims description 5
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 5
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 5
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 150000003463 sulfur Chemical class 0.000 claims description 5
- 229940075420 xanthine Drugs 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- 244000205754 Colocasia esculenta Species 0.000 claims description 4
- 235000006481 Colocasia esculenta Nutrition 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 240000005979 Hordeum vulgare Species 0.000 claims description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 235000015429 Mirabilis expansa Nutrition 0.000 claims description 4
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- 235000021307 Triticum Nutrition 0.000 claims description 4
- 229930013930 alkaloid Natural products 0.000 claims description 4
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 4
- 238000001354 calcination Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- AHICWQREWHDHHF-UHFFFAOYSA-N chromium;cobalt;iron;manganese;methane;molybdenum;nickel;silicon;tungsten Chemical compound C.[Si].[Cr].[Mn].[Fe].[Co].[Ni].[Mo].[W] AHICWQREWHDHHF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
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- 235000013536 miso Nutrition 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
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- 235000010469 Glycine max Nutrition 0.000 claims description 3
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- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 229920001774 Perfluoroether Polymers 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 3
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- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 claims description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 claims description 2
- TWAVLAUIQVYLOR-UHFFFAOYSA-N 1-pyrrol-1-ylpyrrole Chemical group C1=CC=CN1N1C=CC=C1 TWAVLAUIQVYLOR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
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- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
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- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- RTAYJOCWVUTQHB-UHFFFAOYSA-H yttrium(3+);trisulfate Chemical group [Y+3].[Y+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RTAYJOCWVUTQHB-UHFFFAOYSA-H 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyrane Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
200836629 九、發明說明: 【發明所屬之技術領域】 =發明係關於-種新穎之殺蟲組成物,及_種新穎的預防蟲 防方法,係將練蟲域物翻於植物種子或農業植物之 收穫物而預防蟲害。 【先前技術】 國際公開第2GG5/G21488號小冊以及國際公開第2()_73165 就小冊有殺蟲劑及其使用方法之記載。 又’以往絲_於植物種子以驗蟲害之藥劑,有益達胺200836629 IX. Description of the invention: [Technical field to which the invention pertains] = The invention relates to a novel insecticidal composition, and a novel method for preventing insect pests, which is to turn the pests into plant seeds or agricultural plants. Harvesting and preventing pests. [Prior Art] International Publication No. 2 GG5/G21488 and International Publication No. 2 ()_73165 have records of insecticides and methods of use thereof. And 'the past silk _ in the plant seeds to test the insecticide, beneficial to the amine
Litpnd)劑、thiamethoxiam劑、芬普尼㈣·切劑等,已知 對於種子進行喷佈處理、塗抹處理、浸泡處理或粉衣 處理4來發揮效果。 專利文獻1 :國際公開第2005/021488號小冊 專利文獻2 :國際公開第2〇〇5/〇73165號小冊 【發明内容】 (發明欲解決之問題) ,是前述殺蟲在林能預防或難關防之絲。因 二目的在於提供一種新的殺蟲組成物及預防各種蟲害之 此預防在植物種子或農業植物之收穫物中的各種蟲害。 人女發日狀等’為了解決上述問題努力研究之結果,發現將 細式(5)表示之化合物中1種或2種以= 二=杈轴組成物對於植物種子或農業植物之收穫物預 防蟲害,乃完成本發明。 、用肊預 亦即,本發明如下所示。 ㈣2、!^植f種刊或轉細殺蟲、喊物,其特徵在於含有 ^於通式(1)表示之化合物中1種或2種以上的化合物作為有Ϊ 200836629 通式(i) Q I 2 N、 (Χ)η ⑴ ♦X. i式中’ Ai、A2、A3、A4各表示石卢盾 ^ 氮原子, 反原子、氮原子或經氧化之 彼此獨立表示氫原子、C1—C4、pLitpnd), thiamethoxiam, fentanyl (tetra), dicing agent, etc., are known to be applied to the seed by spraying, smearing, soaking or powder coating. Patent Document 1: International Publication No. 2005/021488, pamphlet Patent Document 2: International Publication No. 2〇〇5/〇73165, Volume [Invention] (The problem to be solved by the invention) is that the aforementioned insecticidal prevention in forest can be prevented. Or difficult to prevent the silk. The second objective is to provide a new insecticidal composition and to prevent various pests from preventing various pests in plant seeds or harvests of agricultural plants. In order to solve the above problems, we found that one or two of the compounds represented by the formula (5) were used to prevent the harvest of plant seeds or agricultural plants. Pests are the completion of the present invention. In other words, the present invention is as follows. (4) A compound containing one or more compounds of the compound represented by the formula (1) as a ruthenium of the compound of the formula (1). 2 N, (Χ)η (1) ♦X. In the formula i', Ai, A2, A3, and A4 each represent a stone atom, a nitrogen atom, and an anti-atomic, nitrogen atom or an oxidized one independently represents a hydrogen atom, C1-C4, p
Gi、彼此獨立表示氧原子或硫原子二土 —C4燒幾基, x可為相同或不同,表示氫眉早' 三氟曱基, 4原子、自素原子、Cl —C3烷基或 n表示0至4之整數,Gi, independently of each other, represents an oxygen atom or a sulfur atom, a C4 group, and x may be the same or different, meaning hydrogen eyebrow early 'trifluoromethyl, 4 atom, self atom, Cl - C3 alkyl or n An integer from 0 to 4,
Qi表示苯基, 取代苯基:具有擇自於鹵素原子、C1—r |基=代之C1-C4絲、C2〜C4稀=基cf鹵稀^ 美、Ci,S:C4ri炔基、C3-C8環烷基、C3-C8 *環烷 A 乳基 C3鹵垸氧基、C1—C3烧硫基、C1— 鹵、元瓜基、Cl 一C3烷基亞磺醯基、C1 — C3鹵烷基亞磺醯基、 C1-C3絲磺醯基、Cl-C3鹵絲績醯基、C1—C4烧胺基、二 C1 C4烧胺基、胺基、氰基、硝基、經基、C1—C4烧魏基、C1 ~C4鹵烧羰基、C1—C4烷羰氧基、C1 — C4鹵烷羰氧基、cl — C4烧氧羰基、ci 一C4 i烷氧羰基、C1—C4烷羰胺基、C1—C4 鹵烧羰胺基、Cl —C4烧基石黃醯氧基、ci —C4鹵烧基石黃醢氧基、 芳磺醯氧基、五氟硫烷基、苯炔基或苯基之中相同或不同之1個 以上取代基, 碳環基(在此之碳環基表示萘基、四氳萘基、二氫茚基、苐基、 9—侧氧基苐基、金剛烷基、蒽基或降福基。), 取代碳環基:具有擇自於鹵素原子、C1—C4炫基、C1 — C4 鹵規基、經取代之Cl —C4烷基、C2-C4烯基、C2 — C4鹵烯基、 200836629 C2—C4块基、C2-C4鹵块基、C3 — C8環烧基、C3 — C8 _環烷 基、Cl —C3烧氧基、C1-C3 i烧氧基、C1—C3烷硫基、C1-C3齒燒硫基、C1 一C3烷基亞磺醯基、C1一C3 i烷基亞磺醯基、 Cl —C3院基石黃醯基、C1 — C3鹵烷基石黃醯基、C1_C4烷胺基、二 C1 —C4烧胺基、胺基、氰基、硝基、羥基、C1—C4烷羰基、α —C4,烧幾基、C1 — C4烷羰氧基、C1_C4鹵烷羰氧基、ci — C4烧氧幾基、C1-C4 _烧氧数基、C1—C4烷幾胺基、C1_C4 基、C1-C4烧基石練氧基、C1 —C4鹵烧基磺酿氧基、 芳〜1&氧基、五氟硫烷基、苯炔基或苯基之中相同或不同之i個 以上取代基(在此之碳環基表示萘基、四氫萘基、二氫茚基、苐基、 9一侧氡基第基、金剛烷基、蒽基或降葙基。), —雜%基(在此之雜環基表示吡畊基、吡啶基、N__氧化吡啶基、 °密咬基、料基、ϋ夫喃基、齡基ϋ基L錄”号二嗤 基、嘆唑基、異嘆唑基、嗟二唑基、α比略基、咪嗤基、三唑基、 H、Γ哇基、苯并_基、苯并絲、苯并σ夫喃基、苯并 ,吩基、啥琳基、異钱基、f朵基、異啊基、1Η_異脅朵基、 /一 二糾基、苯并[1,3]二料基、四氫㈣ 基、吖啶基或二氫哌喃基。),或 代:具有擇自於_素原子、C1〜C4烧基、C1—C4 鹵烧基、經取代之C1-C4絲、C2—C4 _ C2-C4炔基、C2-C4幽炔基、C3 —崎基 I η—口厌丞C8^垸基、C3 —C8鹵環烷 ί基、C1 —C3 ^烷氧基、Cl—C3 烷硫基、C1 — 3 齡基亞麵基、 C 磺酸基、C1-C4烧胺基、二 -C4鹵燒羰基、C1 —C4烧羰氧基、Ci〜C4 f J基二C1 C4烧驗基、C1—C4姐氧絲、C1〜C4 基、= 函烧幾胺基、Cl-C4絲石黃醯氧基、C1 气C1 —c4 芳磺醯氧基、五氟硫絲、顧姆基之中相 200836629 ΐΐϊ代f (在此之㈣基表示対基吻定基、N-氧化呢咬基、 噹《疋土、σ合畊基、呋喃基、噻吩基、噚唑基、異噚唑基、二唑 基、嗟哇基、異麵基、嗟二哇基、轉基、咪唾基、三哇^、 °比唾基、四铺、苯并+ 坐基、苯并啊基、苯并七南基、i并 噻吩基、喹啉基、異喹啉基、吲哚基、異吲哚基、lH—異吲哚基、 2,3-二氫-苯并[M]二今井基、苯并明 1南 吖啶基或二氫哌喃基。); 飞疋南丞 Q2表示:Qi represents a phenyl group, a substituted phenyl group: a C1-C4 filament selected from a halogen atom, a C1-r | group = a C2 to a C4 thin group, a cf halogen, a Ci, an S: C4ri alkynyl group, a C3 -C8 cycloalkyl, C3-C8*cycloalkane A, C3-halomethoxy, C1-C3 sulphur, C1-halo, guar, Cl-C3 alkylsulfinyl, C1-C3 Alkylsulfinyl, C1-C3 sulphonyl, Cl-C3, fluorenyl, C1-C4 acryl, di-C1 C4 aminyl, amine, cyano, nitro, thiol, C1-C4 burnt Wei, C1 ~ C4 halogenated carbonyl, C1-C4 alkoxycarbonyl, C1-C4 halocarbonyloxy, cl-C4 alkoxycarbonyl, ci-C4 i alkoxycarbonyl, C1-C4 alkane Carbonyl group, C1-C4 halogenated carbonylamino group, Cl-C4 alkyl sulphate, ci-C4 halogenated fluorenyl fluorenyloxy, arylsulfonyloxy, pentafluorosulfanyl, benzynyl or One or more substituents which are the same or different among the phenyl groups, a carbocyclic group (wherein the carbocyclic group represents a naphthyl group, a tetradecylnaphthyl group, a dihydroindenyl group, a fluorenyl group, a 9-side oxyalkyl group, a diamond Alkyl, fluorenyl or fluorenyl.), substituted carbocyclyl: selected from a halogen atom, C1-C4 leukoxene, C1-C 4 halo group, substituted C1-C4 alkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, 200836629 C2-C4 block, C2-C4 halo block, C3 - C8 cycloalkyl, C3 - C8 _cycloalkyl, Cl -C3 alkoxy, C1-C3 i alkoxy, C1-C3 alkylthio, C1-C3 thiol, C1 - C3 alkyl sulfinyl, C1 - C3 i Alkyl sulfinyl, Cl—C3, sulphate, C1—C3 haloalkyl fluorenyl, C1—C4 alkylamino, di C1-C4 acryl, amine, cyano, nitro, hydroxy, C1-C4 alkane Carbonyl group, α-C4, aryl group, C1-C4 alkoxycarbonyl group, C1_C4 haloalkylcarbonyloxy group, ci-C4 alkoxy group, C1-C4-burning oxygen group, C1-C4 alkanoamine group, a C1_C4 group, a C1-C4 alkyl group, an oxygen group, a C1-C4 halogen group sulfomethoxy group, an aryl group 1~amp; an oxy group, a pentafluorosulfanyl group, a phenyl alkynyl group or a phenyl group, the same or different ones The above substituent (wherein the carbocyclic group represents a naphthyl group, a tetrahydronaphthyl group, an indanyl group, a fluorenyl group, a 9-membered fluorenyl group, an adamantyl group, a fluorenyl group or a fluorenyl group), % base (the heterocyclic group here means pyridinyl, pyridyl, N__oxidized pyridyl, ° dense Biting base, material base, sulphonyl group, age-based fluorenyl group L-recorded dimercapto group, oxazolyl, isotazolyl, oxadiazolyl, α-l-butyryl, imidazolyl, triazolyl, H, oxime, benzo-yl, benzo-, benzo-S-furanyl, benzo, phenyl, fluorenyl, iso-kilo, f-radical, iso-yl, 1-indole / / 2, benzo, benzo [1,3] dibasic, tetrahydro (tetra), acridinyl or dihydropyranyl. ), or generation: having a source derived from a γ atom, a C1 to C4 alkyl group, a C1-C4 halogen group, a substituted C1-C4 wire, a C2-C4 _C2-C4 alkynyl group, a C2-C4 alkynyl group , C3 — 崎基 I η—mouth 丞 丞 C8 垸 、, C 3 —C 8 halocycloalkano, C 1 —C 3 ^ alkoxy, Cl—C 3 alkylthio, C 1 — 3 age base subunit, C Sulfonic acid group, C1-C4 acrylamine group, di-C4 halogen-burning carbonyl group, C1-C4-burning carbonyloxy group, Ci~C4 f J-based di-C1 C4 calcining group, C1-C4 oxidizing wire, C1~C4 group , = calcined amino group, Cl-C4 smectite, C1 gas C1 - c4 aryl sulfonyloxy, pentafluorosulfide, Gumki middle phase 200836629 f generation f (here (four) base対 吻 吻 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、嗟二哇基,转基,米唾基,三哇^, ° than saliva, Sipu, benzoxyl, benzoyl, benzoheptanyl, i-thienyl, quinolinyl, Isoquinolinyl, fluorenyl, isodecyl, lH-isoindolyl, 2,3-dihydro-benzo[M]dijinjing, benzopyrene 1 Nanxun The base or dihydro-pyran-yl); Cheng fly piece goods South Q2 represents:
一长,環基(在此之碳環基表示萘基、四氫萘基、C3—C8環烷基、 一氫茚基、苐基、9一侧氧基苐基、金剛烷基或降福基。), 取代碳環基:具有擇自鹵素原子、C1_C4烷基、C1—C4鹵 烷基、經取代之Cl —C4唬基、C2-C4烯基、C2 — C4 _基、 C2-C4炔基、C2-C4鹵炔基、C3-C8環烷基、C3-C8鹵環烷 基、Cl —C3烧氧基、C1 — C3 ii烧氧基、C1-C3烧硫基、C1 — C3處烧硫基、ci —C3烧基亞礦醯基、C1 — C3鹵烧基亞石黃醯基、 Cl.— C3烷基磺醯基、Cl— C3鹵烷基磺醯基、C1 _C4烷胺基、二 Cl C4烧胺基、氰基、硝基·、經基、ci一C4烧幾基、ci~C4 ^烷羰基、C1 — C4烷羰氧基、ci一C4鹵烷羰氧基、C1 — C4烷氧 碳基、C1 一C4鹵烧氧幾基、C1—C4烷幾胺基、C1 一C4鹵烷幾胺 基、C1—C4烷基石黃醯氧基、C1 一C4鹵烷基磺醯氧基、芳磺醯氧 基、.五氟硫烷基或苯基之中相同或不同之1個以上取代基(在此之 石反環基表示奈基、四氫萘基、C3 — C8環烧基、二氫茚基、結基、 9~側氧基第基、金剛烷基或降福基。), 雜環基(在此之雜環基表示吡呼基、吡啶基、N —氧化吡啶基、 嘧啶基、嗒畊基、呋喃基、噻吩基、噚唑基、異噚唑基、噚二唑 基、噻唑基、異噻唑基、噻二唑基、吡咯基、咪唑基、三唑基、 ϋ比唑基、四唑基、苯并噻唑基、苯并噚唑基、苯并呋喃基、苯并 嗟吩基、喹啉基、異喹啉基Ί朵基、異吲哚基、m—異吲哚基、 2,3~二氫一苯并[I,4]二噚啩基、苯并[1,3]二噚唑基、四氫哌喃基、 200836629 本弁味哇基或二氮旅喃基。), 取代雜環基··具有擇自於鹵素原子、C1 一C4烷基、C1 — C4 鹵烧基、經取代之Cl —C4烧基、C2 —C4稀基、C2 — C4鹵烯基、 C2—C4炔基、C2 — C4鹵炔基、〇 — C8環烧基、C3 —C8鹵環烷 基、C1 — C3烧氧基、C1 — C3鹵烷氧基、Ci — C3烷硫基、α_ C3鹵烧石瓜基、Cl —C3烧基亞石黃醢基、ci —C3鹵烧基亞石黃酸基、 C1 一C3嫁基石黃醢基、C1 — C3鹵烧基石黃醯基、C1 — C4烧胺基、二 C1 一 C4烧fe基、氰基、確基、經基、ci —C4烧幾基、C1 — C4 函烧幾基、C1 一C4烷羰氧基、C1 一C4鹵烷羰氧基、C1 — C4烧氧 幾基、ci-c4 i烷氧羰基、C1_C4烷羰胺基、C1—C4鹵烷幾胺 基、C1-C4烷基磺醯氧基、C1_C4 _烷基續醯氧基、芳磺醯氧 基、五氟硫烧基或苯基之中相同或不同之1個以上取 力 雜瓖基表示t井基吻定一 2 一基“比咬一4_基、N 一氧定基之 嘧啶基、嗒畊基、呋喃基、噻吩基、噚唑基、異^ 基、售錄、異射基、嗟二唾基、咖各基、。米=基三^上 吨唑基、四唑基、苯并噻唑基、苯并噚唑基、苯并呋喃基、 噻吩基、喹啉基、異喹啉基、吲哚基、異巧哚基、出一里^ 、 2,3-二氫-苯并[1,4]二今井基、苯并[⑶二今 &喃^ 苯并咪唑基或二氫哌喃基。), 2瓜甬暴 C1 — C6烧基, 取代C1-C6烧基··具有擇自於鹵素原子、α—c C2-C4?基、C2-C4 .稀基、C2 —…夬基、C2_C4齒快工、 C3-C8 環絲、C3-C8 i環絲、C1 —C3 絲基、a—g Ϊ氧C3姐硫基、C1—咖基亞磺醯 基、Cl —C3鹵烷基亞石頁醯基、C1__C3烧基石黃醯基、C1—c J輕基、Cl-C4烧胺基、二α.—C4烧胺基、1基、雜:、; 基、C1-C4,幾基、C1—C4鹵基、C1—C4烧幾氧基、^ -C4鹵烧幾氧基、C1 —C4燒氧幾基、C1—C4函烧氧幾^a long, cyclic group (wherein the carbocyclic group represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, a monohydroindenyl group, a fluorenyl group, a 9-side oxyalkyl group, an adamantyl group or a blessing group) Substituted carbocyclic group: having a halogen atom, a C1_C4 alkyl group, a C1-C4 haloalkyl group, a substituted Cl-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4- group, a C2-C4 group Alkynyl, C2-C4 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, Cl-C3 alkoxy, C1-C3 ii alkoxy, C1-C3 sulphur, C1-C3 Sulfur-based, ci-C3 alkyl sulfonium, C1 - C3 halogenated sulfastyl sulfhydryl, Cl.-C3 alkylsulfonyl, Cl-C3 haloalkylsulfonyl, C1 -C4 alkylamine , diCl C4 amine group, cyano group, nitro group, thiol group, ci-C4 alkyl group, ci~C4 alkyl alcohol group, C1-C4 alkylcarbonyloxy group, ci-C4 haloalkylcarbonyloxy group, C1 —C4 alkoxycarbonyl, C1—C4 halooxyalkyl, C1-C4 alkanoamine, C1—C4 haloalkylamino, C1-C4 alkyl fluorenyloxy, C1-C4 haloalkyl sulfonate One or more substituents which are the same or different among the decyloxy group, the arylsulfonyloxy group, the pentafluorosulfanyl group or the phenyl group (the stone here) A cyclic group means a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group, a carboxyl group, a 9-oxooxy group, an adamantyl group or a ruthenium group.), a heterocyclic group (herein Heterocyclyl means pyridyl, pyridyl, N-oxidized pyridyl, pyrimidinyl, hydrazine, furyl, thienyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazole Base, thiadiazolyl, pyrrolyl, imidazolyl, triazolyl, indolozolyl, tetrazolyl, benzothiazolyl, benzoxazolyl, benzofuranyl, benzoxenyl, quinoline , isoquinolinyl fluorenyl, isodecyl, m-isodecyl, 2,3~dihydro-benzo[I,4]diindolyl, benzo[1,3]dioxime Azolyl, tetrahydropyranyl, 200836629, benzoic acid or dinitrocarbenyl.), substituted heterocyclic group · having a halogen atom, a C1 - C4 alkyl group, a C1 - C4 halogen group, Substituted Cl—C4 alkyl, C2-C4 dilute, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, fluorene-C8 cycloalkyl, C3-C8 halocycloalkyl, C1 — C3 alkoxy, C1-C3 haloalkoxy, Ci—C3 alkane , α_ C3 halogen-burned squash base, Cl-C3 alkyl sulphate, ci-C3 halogenated sulphate, C1 - C3 sulphate, C1 - C3 halogenated sulphate, C1 - C4 sulphur Base, two C1 - C4, a cyano group, a cyano group, a decyl group, a thio-C4 group, a C1 - C4 group, a C1 - C4 alkylcarbonyl group, a C1 - C4 halocarbonyloxy group , C1 - C4 aerobic acid group, ci-c4 i alkoxycarbonyl group, C1_C4 alkylcarbonylamino group, C1-C4 haloalkylamino group, C1-C4 alkylsulfonyloxy group, C1_C4-alkyl group One or more of the same or different ones of the arylsulfonyloxy group, the pentafluorosulfoxy group or the phenyl group, which means that the t-well is a one-two base. A pyridyl group, a ruthenium group, a furyl group, a thienyl group, a carbazolyl group, an iso-yl group, a commercially available, a fluorenyl group, a hydrazide group, a caffeyl group. m = benzyl oxazolyl, tetrazolyl, benzothiazolyl, benzoxazolyl, benzofuranyl, thienyl, quinolyl, isoquinolinyl, fluorenyl, hydrazino , one out of ^, 2,3-dihydro-benzo[1,4] dioxin, benzo[(3) dioxin & benzobenzimidazolyl or dihydropyranyl. ), 2 甬 甬 C C1 — C6 alkyl, substituted C1-C6 alkyl ·· has selected from halogen atom, α-c C2-C4?, C2-C4. dilute, C2 —... sulfhydryl, C2_C4 Rapid tooth, C3-C8 ring wire, C3-C8 i-ring wire, C1-C3 wire base, a-g Ϊ oxygen C3 sister thio group, C1-macakisulfonyl group, Cl-C3 haloalkyl sulphite醯 醯, C1__C3 alkyl sulphate, C1-c J light base, Cl-C4 amine group, two α.—C4 amine group, 1 group, hetero:, base, C1-C4, several groups, C1— C4 halo, C1-C4 caloxy, ^-C4 halooxy, C1-C4 oxygenated, C1-C4 functional oxygen
-C4驗胺基、Cl-C4自燒幾胺基、α — C4⑥基雜氧1Q 200836629 -C4鹵炫基石黃酿氧基、芳顧氧基、域硫感或苯基之中相同 或不同之1個以上取代基, 以通式(2)表示之基:-C4 test amine group, Cl-C4 self-burning amine group, α-C46-based hetero-oxygen 1Q 200836629 -C4 halogen-based sapphire yellow oxy group, argon oxy group, domain sulphur sensation or phenyl group the same or different One or more substituents, which are represented by the formula (2):
(2) 可為相同或不同,表示 (式中,γι、γ2、γ3、Y4、Y5 氳原子, 鹵素原子, C1 一 C6燒基, ri 絲:具有擇自於較原子、C1—C3烧氧基、 p其氧土、C1—C3烧硫基、C1—C3自烧硫基、α—α ί基?C3齒烧基亞俩基、C1—C3錄磺酿基、 i t醢基、C1—U触基、二C1—C4燒胺基、氰 “負^ 土、C1 —C4烷羰基、C1-C4鹵烷羰基、C1-C4 η 4自鎌氧基、C1 —C4烧氧幾基、C1-C4鹵烧 ί Ϊί U4烷羰胺ΐ、C1,烷羰胺基、C1 -C4賴 Χδ夕^美之+ 絲顧氧基、料醯氧基、五氟號基或炫 基石夕腐土之中相同或不同之1個以上取代基, ^ ^ c^c4 ' C2~C4^ C6嫁氧基、a—C6 _烧氧基,衣'—C8鹵環烧基、C1— 、_ 烧氧基:經過擇自於氫原子、織、氯原子、(2) may be the same or different, indicating (wherein, γι, γ2, γ3, Y4, Y5 氲 atom, halogen atom, C1 - C6 alkyl group, ri wire: having a choice from a lower atom, C1-C3 burning oxygen Base, p its oxygen soil, C1-C3 sulfur-burning group, C1-C3 self-burning sulfur group, α-α ί-based C3 dentate base, C1-C3 sulphonate, it thiol, C1— U-contact group, di-C1-C4 amine group, cyanide "negative", C1-C4 alkylcarbonyl, C1-C4 halocarbonyl, C1-C4 η4 from decyloxy, C1-C4 aerobic group, C1 -C4 卤烧ί Uί U4 alkyl carbonyl hydrazine, C1, alkyl carbonyl amine, C1 - C4 赖 Χ 夕 ^ 美 美 丝 丝 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基 氧基One or more substituents which are the same or different, ^ ^ c^c4 ' C2~C4^ C6 grafted oxy group, a-C6 _ alkoxy group, clothing '-C8 halocycloalkyl group, C1—, _ alkoxy group : selected from hydrogen atoms, woven, chlorine atoms,
漠原子/、原子、C1-C6烷氧基4C1 — C 不同之1細上取代基, ⑽魏之中相同或 矸經1個以上羥基取代之C1—C6鹵烷基, =1,上C1—C6鹵燒基取代之C1—C6 _絲, 7、、二1個以上烷氧基取代之Cl—C6鹵烷基, <經1個以上鹵烷氧基取代之C1—C6 s烷基, 200836629 C1—C6烷硫基, Cl —C6鹵烷硫基, 漠原=峨料' 、氣原子、 不同之丨基或α—«銳緣之中相同或 C1 — C6烷基亞磺醯基, C1 —C6鹵烷基亞磺醯基, C6鹵燒氧基之中 料取ί —C6鹵烧基亞石黃醯基:'經過擇自於氫原子、經笑、衰 原子、_子、C1—C6絲基或ci—i匕基、乳Atom atom, atom, C1-C6 alkoxy 4C1 - C different substituents, (10) C1-C6 haloalkyl which is the same or substituted by one or more hydroxy groups, =1, upper C1-C6 halogen C1-C6 _ silk substituted by alkyl group, 7, or more than one alkoxy-substituted C1-C6 haloalkyl group, <C1-C6 s alkyl substituted by one or more haloalkoxy groups, 200836629 C1 —C6 alkylthio, Cl—C6 haloalkylthio, Moyuan=峨', gas atom, different sulfhydryl or α—“the same in the sharp edge or C1—C6 alkyl sulfinyl, C1 — C6 haloalkyl sulfinyl group, C6 halo alkoxy group is taken from ί-C6 halocarbazide fluorenyl group: 'after selection from hydrogen atom, laughter, fading atom, _ sub, C1-C6 silk base Or ci-i 匕 base, milk
相同或不同之1個以上取代基所取代, C1〜C6烷基磺醯基, C1〜C6鹵烷基石黃醯基, 2代C1 — C0鹵烷基磺醯基:經過擇自於氫原子、羥 子' _子、α—⑽氧基或C1—C6鹵 = 同或不同之1個以上取代基所取代, 又干相Substituted by the same or different substituents, C1~C6 alkylsulfonyl, C1~C6 haloalkyl fluorenyl, 2nd C1 - C0 haloalkylsulfonyl: selected from hydrogen atom, hydroxyl group '_子, α—(10) oxy or C1-C6 halogen = substituted with one or more substituents of the same or different, dry phase
Cl C4烧氧友基、ci—C4鹵烧氧幾基、C1—C4烧幾胺其、 CK4 4絲胺基、C1 —C6絲石黃醯氧基, 贱基 C1 — C6鹵烷基磺醯氧基、C1—C4烷羰基、C1_C4鹵烷羰 土 ^i—C4烧羰氧基、C1_C4鹵烷羰氧基、氰基、硝基、羥基= 五氟硫烷基、羧基、胺曱醯基、C1_C3烷胺基羰基、笨 吼咬氧基, 取代吼啶氧基:具有擇自於鹵素原子、Cl —C4烷基、C1 — C4鹵垸基、經取代之C1_C4烷基、C2_C4烯基、C2 —C4鹵烯 C2 —C4块基、C2—C4鹵炔基、C3 —C8環烷基、C3 — C8自 被烧基、C1 — C3烷氧基、C1—C3鹵烷氧基、C1-C3烷硫基、 C3 _烧硫基、C1 — C3烧基亞石黃醢基、C1 一C3鹵烧基亞石黃醱 ,、C1—C3烷基石黃醯基、ci —C3鹵烷基石黃醯基、Cl —C4烷胺基、 二Cl —C4烷胺基、氰基、硝基、羥基、C1—C4烷羰基、C1 —C4 ί燒幾基、Cl 一C4烷羰氧基、C1 _C4鹵烷羰氧基、ci 一C4烷氧 11 200836629 獄基、Cl一C4鹵烷氧徵基、Cl —C4烷獄胺基、Cl一C4鹵烷獄胺 基、C1-C4烷基磺醯氧基、C1 — C4鹵烷基磺醯氧基、芳續醯氧 基、五氟硫院基或苯基之中相同或不同之1個以上取代基, 苯基, 取代苯基:具有擇自於鹵素原子、C1 — C4烷基、Cl —C4鹵 烷基、經取代之C1 — C4烷基、C2 — C4烯基、C2 — C4鹵烯基、 C2 —C4炔基、C2 —C4鹵炔基、C3 — C8環烷基、C3 — C8 烧 基(在此之雜%基表示σ比呀基、吼咬基、Ν—氧化II比咬美、 嘧啶基、嗒畊基、呋喃基、噻吩基、噚唑基、異噚唑基、噚2嗤 基、噻唑基、異噻唑基、噻二唑基、吡咯基、咪唑基、三唑美、 ^坐,、四絲、苯并♦錄、苯并今坐基、苯并π夫錄、J并 基、Cl —C3烷氧基、Cl —C3鹵烷氧基、C1-C3烷硫基、d C3鹵烧硫基、Cl — C3烧基亞石黃酿基、Cl —C3鹵烧基亞石黃酿基、 C1 — C3烷基磺醯基、Cl —C3鹵烷基磺醯基、C1 — C4烧胺基Γ二 C1 — C4烷胺基、氰基、硝基、羥基、C1 一C4烷羰基、C1 — C4 鹵烷羰基、C1 一C4烷羰氧基、〇1一€4鹵烷羰氧基、。1~〇4烧氧 %基、C1 — C4鹵烧氧幾基、C1 一C4烧戴胺基、Cl — C4 1¾烧幾胺 基、C1:C4烧基磺醢氧基、α一C4 _烷基續醯氧基、芳續^氧 基、五氟硫烧基或苯基之中相同或不同之1個以上取代基, 1Η—異吲哚基、 基、四氫哌喃基 或二氫旅喃基。), 或, ϋ塞吩基、金林基、異啥琳基、喻朵基、異弓卜朵基、 2,3-二氫一苯并[I,4]二噚畊基、苯并以,3]二噚唑基、Cl C4 Oxygenophilic group, ci-C4 halogenated oxygen group, C1-C4 alkaloid, CK4 4 silk amine, C1-C6 silkyxanthine, fluorenyl C1 - C6 haloalkyl sulfonate , C1-C4 alkylcarbonyl, C1_C4 halocarbonyl carbonyl ^i-C4 carbonyloxy, C1_C4 halocarbonyloxy, cyano, nitro, hydroxy = pentafluorosulfanyl, carboxyl, amine sulfhydryl, C1_C3 alkylaminocarbonyl, alkoxy, substituted acridineoxy: having a halogen atom, a C1-C4 alkyl group, a C1-C4 halogen group, a substituted C1_C4 alkyl group, a C2_C4 alkenyl group, a C2 group —C4 halene C2—C4 block, C2-C4 haloalkynyl, C3-C8 cycloalkyl, C3-C8 self-alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 Alkylthio group, C3 _ sulphur group, C1 - C3 alkyl sulphate, C1 - C3 halogenated sulphate, C1 - C3 alkyl sulphate, ci - C3 haloalkyl sulphate, Cl - C4 Amino, diCl-C4 alkylamino, cyano, nitro, hydroxy, C1-C4 alkylcarbonyl, C1-C4 oxalate, Cl-C4 alkylcarbonyloxy, C1_C4 halocarbonyloxy, ci a C4 alkoxygen 11 200836629 Prison base, Cl-C4 haloalkoxy levy Cl—C4 alkylamine, Cl—C4 haloalkylamine, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, alkyl sulfoxide, pentafluorosulfurate or One or more substituents which are the same or different among the phenyl groups, a phenyl group, a substituted phenyl group: having a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a substituted C1-C4 alkyl group, C2 - C4 alkenyl, C2 - C4 haloalkenyl, C2 - C4 alkynyl, C2 - C4 haloalkynyl, C3 - C8 cycloalkyl, C3 - C8 alkyl (wherein the heteropoly group represents σ ratio) , biting base, Ν-oxidation II than bite, pyrimidinyl, hydrazine, furyl, thienyl, carbazolyl, isoxazolyl, fluorenyl, thiazolyl, isothiazolyl, thiadiazole Base, pyrrolyl, imidazolyl, triazole, ^ sit, tetrafilament, benzoxyl, benzoxanthene, benzopyridin, J-mercapto, Cl-C3 alkoxy, Cl-C3 Haloalkoxy, C1-C3 alkylthio, d C3 halogenated sulfur, Cl - C3 alkyl sulphate, Cl - C3 halogenated sulphate, C1 - C3 alkyl sulfonyl , Cl—C3 haloalkylsulfonyl, C1—C4 acrylamine ΓC1—C 4 alkylamino, cyano, nitro, hydroxy, C1 - C4 alkylcarbonyl, C1 - C4 halocarbonyl, C1 - C4 alkylcarbonyloxy, 〇1 - 4 halocarbonyloxy, 1~〇4 Oxygenated %, C1 - C4 halogenated oxygen group, C1 - C4 burned amine group, Cl - C4 13⁄4 burned amine group, C1: C4 alkylsulfonyloxy group, α-C4 alkyl group One or more substituents which may be the same or different among the oxy group, the pentafluorosulfide group or the phenyl group, a 1 hydrazine-isoindenyl group, a tetrahydropyranyl group or a dihydronenyl group. ), or, thiophene, jinlinji, iso-linyl, yuduji, iso-broadenyl, 2,3-dihydro-benzo[I,4]dioxin, benzo, 3 Dicarbazolyl,
12 20083662912 200836629
基、五氟硫烷基或笨基之 雜環基轰示咕吨:S:. C4燒羰氧基、Cl —C4鹵烷羰氧基、Cl —C4烷氧 、C1 一C4 烧幾基、C1 一C4 ^燒氣羰基、Cl —C4烷羰胺基、(:1一〇4鹵烷羰胺 良基、C1—C4鹵烧基石黃酿氧基、芳石黃酿氧 之中相同或不同之1個以上取代基(在此之Heterocyclic, pentafluorosulfanyl or stupid heterocyclic ring bombardment: S: C4 carbonyloxy, Cl-C4 halocarbonyloxy, Cl-C4 alkoxy, C1 - C4 alkyl, C1 - C4 ^ aerated carbonyl, Cl - C4 alkylcarbonylamine, (: 1 - 4 haloalkyl carbonyl amine good, C1 - C4 halogenated sulphur yellow oxy, aryl stone yellow oxygen in the same or different More than one substituent (here
^ 基、N—氧化口比啶基、嘧口定基、嗒π井基、 号哇基、異今嗤基、噚二峻基、嘆嗤基、異嗟 11比略基、味嗤基、三tr坐基、π比唾基、四嗤基、 •嗅基、苯并呋喃基、苯并噻吩基、喹啉基、 異吲哚基、1H—異吲哚基、2,3—二氫一苯并 關^^基^笨并明二今坐基^氫㈣基或二^南基); n m1 \5可為相同或不同且表示鹵素原子、C1-C4烷基、 —^鹵烧基、C1〜C3烷硫基、C1—C3 _烷硫基、C1 —C3烷 土亞石買醯基、〜C3鹵烷基亞磺醯基、ci—C3烷基磺醯基、C1 -C3鹵烧基石黃^基或氰基之情形,不含γ3表示C2—C6全氣烧 基、C1 一C6全氟垸硫基、C1 一C6全氟烷基亞磺醯基或C1 —C6 全氟烧基磺醯基之情形),或 以通式(3)表示之基^ base, N-oxidation mouth ratio pyridine group, pyridinyl group, 嗒π well base, ke ke group, 嗤 嗤 base, 噚 峻 基 base, 嗤 嗤 base, 嗟 嗟 11 略 基 base, miso base, three Tr sitting group, π-barryl group, tetradecyl group, • olfactyl group, benzofuranyl group, benzothienyl group, quinolyl group, isodecyl group, 1H-isodecyl group, 2,3-dihydrogen Benzene is ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ , C1~C3 alkylthio, C1-C3 _ alkylthio, C1-C3 alkane sulphate, decyl C3 halosulfonyl, ci-C3 alkyl sulfonyl, C1-C3 In the case of burning a basestone or a cyano group, the absence of γ3 means C2-C6 all-gas burned base, C1-C6 perfluorosulfonylthio group, C1-C6 perfluoroalkylsulfinyl group or C1-C6 perfluoroalkyl In the case of a sulfonyl group, or a group represented by the formula (3)
(式中’ Y6、Y7、Ys、Y9可為相同或不同,表示氫原子、鹵素 原子、C1 — C6烷基、ci —C6鹵烷基、C2 —C4烯基、C2 —C4鹵 烯基、C2 —C4炔基、C2 —C4 _炔基、C3 — C8環烷基、C3 — C8 鹵環烷基、Cl—C4烷氧基、C1 一C4鹵烷氧基、可經1個以上經 基取代之C1 — C6鹵烷基、可經1個以上烷氧基取代之C1 —C6鹵 烷基、可經1個以上鹵烷氧基取代之Cl 一C6鹵烷基、Cl —C6烧 硫基、C1 一 C6鹵烧硫基、C1 一 C6烧基亞續酿基、C1 一 C6鹵燒基 亞石黃醯基、C1—C6燒基石黃醯基' Cl —C6鹵烧基石黃醢基、C1 — C6 13 200836629 烷基磺醯氧基、Cl—C6 i烷基磺醯氧基、Cl —C4烷羰基、ci一 C4鹵烷羰基、C1-C4烷羰氧基、C1 一C4鹵烷羰氧基、氰基、蹲 基、羥基、五氟硫烧基、苯基, 取代苯基:具有擇自於鹵素原子、C1 — C4烧基、C1~C4鹵 烷基、經取代之Cl —C4烷基、C2 —C4烯基、C2 —C4 _稀基、 C2-C4炔基、C2 —C4鹵炔基、C3-C8環烧基、C3 —C8鹵環烧 基、C1 — C3烷氧基、C1-C3鹵烷氧基、C1 — C3烷硫基、C1_ C3鹵烧硫基、Cl —C3烧基亞磺醯基、Cl —C3鹵烧基亞石黃酿基、 Cl—C3烷基磺醯基、C1 一C3鹵烷基磺醯基、Cl —C4垸胺基Γ二 Cl—C4烷胺基、氰基、硝基、羥基、C1—C4烷羰基、ct_c4 鹵烧羰基、Cl一C4烧羰氧基、C1-C4鹵燒羰氧基、C1 — C4烧氧 幾基、C1 — C4 _烷氧羰基、C1一C4烷羰胺基、C1 — C4鹵烧幾胺 基、C1 — C4烷基磺醯氧基、C1 一C4 _烷基磺醯氧基、芳續醯氧 基、五氟硫烷基或苯基之中相同或不同之1個以上取代基f 〜雜環基(在此之雜環基表示吡畊基、吡啶基、N-氧化吡啶基、 他、啶基、嗒畊基、呋喃基、噻吩基、噚唑基、異噚唑基、噚二唑 基、噻唑基、異噻唑基、噻二唑基、吡咯基、咪唑基、三唑^、 ,唑基、四唑基、苯并噻唑基、苯并噚唑基、苯并呋喃基、J并 噻吩基、喹啉基、異喹啉基、吲哚基、異吲哚基、1H—異吲哚基、 一 &鼠本并[1,4]一u号17井基、本并[1,3]二喝嗤基、四氫η辰喃基 或二氧哌喃基。), 或, 取代雜環基:具有擇自於鹵素原子、C1_C4烷基、〇 ^燒,、經取代之C1 —C4说基、C2 —C4烯基、C2 —C4崎基、 4炔基、C2 —C4鹵炔基、C3 —C8環烷基、C3 —c8鹵環烷 C3燒氧基、C1—C3鹵烧氧基、C1—C3烧硫基、Cl— 二=硫基、Cl—C3烷基亞磺醯基、Cl —C3鹵烷基亞磺醯基、 3燒基石黃醯基、C1 一 C3鹵烧基石黃酸基、C1 一 C4烧胺基、二 C4燒胺基、氰基、石肖基、經基、ci — c4烧幾基、C1 — C4 14 200836629 鹵烧幾基、Cl—* 羰基、0-C4 基、C1—C4鹵絲氧基、C卜C4燒氧 基、C1 — C4絲、C1—C4烧幾胺基、C1-C4鹵烧羧胺 基、五氟硫垸醯氧基、芳磺醒氧 雜環基表示対ί基巾細或不同之1伽X上取代基(在此之 :=;::基;基二氧,,;,、、 唑基、唭二4其:上基異坊唑基、°亏二唑基、噻唑基、異噻 苯并、十坐基、三唾基、♦坐基、四唾基、 ί 基、1H—異邮基、2,3—二氳—苯并 惟了γ γ ίΐ: ]二喝唾基、四氫旅喃基或二氫派喃基)’ C1-C4 a C3 ίΐ J} cf cff^' C1-C4^' 其凸石生酼& ΓΜ 3说瓜基、C1 — C3南烧硫基、Cl一C3烷 :C3 基亞石黃酿基、C1 —C3絲石黃酿基、C1 C2-C6 = ϋ土或鼠基之情形,不含Υδ為C1 —C4鹵絲基、 某戍ci王全氟垸硫基、ci—c6全氟絲亞磺醯 基或Cl —C6全氟烷基磺醯基之情形。)}。 通式g中如[1]之殺蟲組成物,其中,以通式⑴表示之化合物,係 八1表不碳原子、氮原子或經氧化之氮原子· A2、A3、A4表示碳原子; ’ R1、R2彼此獨立表示氫原子或C1—C4烷基·(wherein Y6, Y7, Ys, Y9 may be the same or different and represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a ci-C6 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, C2-C4 alkynyl, C2-C4-alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, Cl-C4 alkoxy, C1-C4 haloalkoxy, may pass through more than one Substituted C1 - C6 haloalkyl, C1-C6 haloalkyl which may be substituted by one or more alkoxy groups, Cl-C6 haloalkyl group which may be substituted by one or more haloalkoxy groups, Cl-C6 sulfur-burning group , C1 - C6 halogen-burning sulfur group, C1 - C6 alkyl sulphide, C1 - C6 halogenated sulphate, sulphate, C1 - C6 sulphur base sulphate 'Cl - C6 halogenated sulphate sulphate, C1 - C6 13 200836629 Sulfosulfonyloxy, Cl—C6 ialkylsulfonyloxy, Cl—C4 alkylcarbonyl, ci-C4 halocarbonyl, C1-C4 alkoxycarbonyl, C1-C4 halocarbonyloxy, cyano, Sulfhydryl, hydroxy, pentafluorosulfanyl, phenyl, substituted phenyl: having a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a substituted Cl-C4 alkyl group, a C2-C4 group Alkenyl, C2-C4-thinyl, C2-C4 alkynyl C2—C4 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1_C3 halogenated sulfur , Cl—C3 alkyl sulfinyl group, Cl—C3 halogenated sulfite yellow aryl, Cl—C 3 alkyl sulfonyl, C 1 —C 3 haloalkyl sulfonyl, Cl —C 4 decyl fluorene Cl—C4 alkylamino group, cyano group, nitro group, hydroxyl group, C1-C4 alkylcarbonyl group, ct_c4 halogenated carbonyl group, Cl-C4 carbonyloxy group, C1-C4 halogenated carbonyloxy group, C1-C4 alkoxy group , C1 - C4 - alkoxycarbonyl, C1 - C4 alkylcarbonylamino, C1 - C4 halogenated amino group, C1 - C4 alkylsulfonyloxy, C1 - C4 - alkylsulfonyloxy, aromatic One or more substituents f to heterocyclic groups which are the same or different among the oxy group, the pentafluorosulfanyl group or the phenyl group (herein, the heterocyclic group means pyridinyl group, pyridyl group, N-oxidized pyridyl group, Pyridyl, hydrazine, furyl, thienyl, carbazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrrolyl, imidazolyl, triazole^, Azyl, tetrazolyl, benzothiazolyl, benzoxazolyl, benzofuranyl, J-thienyl, quinolyl, isoquinolyl, fluorenyl, isodecyl, 1H-isoindolyl, a & azobenz [1,4]-u 17 well, Ben [1,3] Di-indenyl, tetrahydron-n-butyl or di-oxypiperidinyl.), or a substituted heterocyclic group: having a halogen atom, a C1_C4 alkyl group, a hydrazine, a substituted C1 - C4, C2 - C4 alkenyl, C2 - C4, 4, alkynyl, C2 - C4 haloalkynyl, C3 - C8 cycloalkyl, C3 - c8 halocycloalkane C3 alkoxy, C1 - C3 halogenated oxy group, C1-C3 sulphur-based group, Cl-di-thio group, Cl-C3 alkyl sulfinyl group, Cl-C3 haloalkyl sulfinyl group, 3-alkyl sulphate, C1-C3 halogen Pyrite phthalic acid group, C1 - C4 amine group, di-C4 amine group, cyano group, schiffyl group, thio-c4 group, C1 - C4 14 200836629 halogen group, Cl-* carbonyl, 0 -C4 group, C1-C4 halogen-siloxy group, C-C4 alkoxy group, C1-C4 wire, C1-C4-burning amine group, C1-C4 halogen-burning carboxamide group, pentafluorosulfanyloxy group, aromatic The sulfonyloxyheterocyclic group means a substituent on the gamma or a different gamma X (here: =;:: group; basal dioxin, ,;,,, oxazolyl, fluorene 2: 4: carbaziryl, oxadiazolyl, thiazolyl, isothiazolidine, decyl, tris-s, s, s, ί base, 1H-extra-mail base, 2,3-bi-quinone-benzo-only γ γ ΐ ΐ: ] two-salt, tetrahydro-bromo or dihydro-pyranyl) ' C1-C4 a C3 ίΐ J } cf cff^' C1-C4^' embossed oysters & ΓΜ 3 said melon, C1 - C3 South sulphur, Cl - C3 alkane: C3 kiwi yellow wine, C1 - C3 slate yellow Base, C1 C2-C6 = case of bauxite or murine base, excluding Υδ is C1-C4 halogen wire base, 戍ci king perfluoro sulfonium thio group, ci-c6 perfluoromethanesulfinyl group or Cl-C6 The case of perfluoroalkylsulfonyl. )}. The insecticidal composition of the formula [1], wherein the compound represented by the formula (1) is a carbon atom, a nitrogen atom or an oxidized nitrogen atom, A2, A3, and A4; 'R1, R2 independently of each other represent a hydrogen atom or a C1-C4 alkyl group.
Gi、彼此獨立表示氧原子或硫原子· 土’ $為^^不^示氫原子、鹵素原子或三 η表不〇至4之整數;Gi, independently of each other, represents an oxygen atom or a sulfur atom. The soil '$ is ^^ does not indicate a hydrogen atom, a halogen atom or a triple η which is not an integer of 4;
Qi表示苯基, 取代苯基:具有擇自於鹵素原子、C 卜 —C4 伊美 πγ^ι C2—C4 烯基、C2—C4 鹵烯基、C2 C1 — C3 H C3 ^ C8 環烷基、C3 — C8 i 環烷基、 d C3燒乳基、C1 —C3鹵垸氧基、α —c3燒硫基、α —ο齒 15 200836629 烷硫基、Cl —C3烷基亞磺醯基、ci—C3鹵烷基亞磺醯基、Cl 一 C3烷基石黃醯基、C1 — C3鹵烷基磺醯基、C1 — C4烷胺基、二C1 —C4烷胺基、氰基、硝基、羥基、ci 一C4烷羰基、C1 一C4鹵烷 羰基、C1 一C4烷羰氧基、C1 一C4鹵烷羰氧基、C1 一€4烷氧羰基、 C1—C4 iS烧氧獄基、Cl —C4烧幾胺基、Cl—C4 ii烧幾胺基、 Cl—C4烧基石黃醯氧基、C1 一C4 i|烧基續醯氧基、芳績醯氧基、 五氟硫烷基或苯基之中相同或不同之1個以上取代基, 雜玉衣基(在此之雜ί哀基表示他呼基、吼12定基、N 一氧化U比咬基、 疋基、σ合呼基、咬喃基、嗟吩基、号嗤基、異tr号唾基、tr号二0坐 基、嗟嗤基、異售嗤基、嗟二XI坐基、π比T7各基、味峻基、三0坐基、 "比唑基、四唑基、2,3 —二氫—苯并[1,4]二噚唯基、苯并[切二口号 唆基、四氫旅喃基或二氫|喃基。) 或, 取代雜環基:具有擇自於函素原子、C1 一C4烧基、C1 一C4 鹵烧基、經取代之C1 — C4烧基、C2 — C4稀基、C2 — C4鹵烯基、 C2—C4炔基、C2 — C4鹵炔基、C3 — C8環烧基、C3 —C8鹵環烷 基、C1—C3烧氧基、C1 — C3鹵烷氧基、Cl-C3烷硫基、C1 — C3鹵烷硫基、C1 — C3烷基亞磺醯基、Cl —C173鹵烷基亞磺醯基、 Cl一C3烧基石黃醯基、C1 一C3鹵烧基石黃醯基、C1 一C4烧胺基、二 C1 一C4烧胺基、氰基、硝基、經基、Cl —C4烧幾基、C1 一C4 鹵烧羰基、C1 一C4烧幾氧基、C1 — C4鹵燒幾氧基、ci 一C4烧氧 幾基、C1 一C4鹵烧氧羰基、C1 一C4烧羰胺基、ci 一C4鹵烧羰胺 基、C1 — C4烧基石黃醯氧基、Cl—C4鹵烧基石黃酿氧基、芳石黃醯氧 基、五氟硫烧基或苯基之中相同或不同之1個以上取代基(在此之 雜環基表示°比17井基、吼咬基、N—氧化吼咬基、u密咬基、。荅呼基、 呋喃基、噻吩基、噚唑基、異噚唑基、噚二嗤基、噻哇基、異售 哇基、嘆二嗤基、ϋ比洛基、味嗤基、三峻基、π比嗤基、四峻基、 2,3—二氫一苯并[1,4]二今ϋ井基、苯并[1,3]二今π坐基、四氫旅喃基 或二氫旅喃基。); 16 200836629 Q2為通式(2)Qi represents a phenyl group, a substituted phenyl group: having a halogen atom, a C-C4 Imi πγ^ι C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2 C1 - C3 H C3 ^ C8 cycloalkyl group, C3 — C8 i cycloalkyl, d C3 calcined base, C1-C3 halooxy, α-c3 sulfur-burning, α-o-tooth 15 200836629 alkylthio, Cl-C3 alkylsulfinyl, ci- C3 haloalkylsulfinyl, Cl-C3 alkyl fluorenyl, C1-C3 haloalkylsulfonyl, C1-C4 alkylamino, di-C1-C4 alkylamino, cyano, nitro, hydroxy, ci a C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkoxycarbonyl group, a C1-C4 haloalkylcarbonyloxy group, a C1-a4 alkoxycarbonyl group, a C1-C4 iS azide base, a C-C4 burn Amino, Cl—C4 ii, aminyl, Cl—C4, fluorenyl fluorenyloxy, C1—C4 i|alkyl decyloxy, aryloxy, pentafluorosulfanyl or phenyl One or more substituents which are the same or different, and a miscellaneous jade group (in this case, he represents a group of heptyl groups, a ruthenium group 12, an N-oxide U-bite group, a thiol group, a sigma group, a bite Base, porphinyl, sulfhydryl, iso-tr-salt, tr-numbered , fluorenyl, stilbene, bismuth XI, π to T7, succinyl, trisyl, "bisazolyl, tetrazolyl, 2,3-dihydro-benzo [1,4] Diterpenyl, benzo[[2], tetrahydroindenyl or dihydro-carbyl.) or, substituted heterocyclic: having a selected atom, C1-C4 Alkyl, C1 - C4 haloalkyl, substituted C1 - C4 alkyl, C2 - C4, C2 - C4 halo, C2 - C4 alkynyl, C2 - C4 haloalky, C3 - C8 , C 3 -C 8 halocycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, Cl-C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylsulfinyl, Cl—C173 haloalkyl sulfinyl group, Cl—C3 alkyl decyl fluorenyl group, C1—C3 halogenated fluorenyl fluorenyl group, C1—C4 acryl group, di C1—C4 acryl group, cyano group, nitro group, thiol group, Cl—C4, a C1, a C4, a halogenated carbonyl group, a C1—C4 caloxy group, a C1-C4 halogenated oxy group, a ci-C4 aerobic acid group, a C1-C4 halogen-burned oxycarbonyl group, a C1-C4 group. Burning carbonylamine group, ci-C4 halogen-burning carbonylamine group, C1-C4 sulphur base xantheneoxy group, Cl-C4 halogen group One or more substituents which may be the same or different among the yellow oxy, aryl xanthine, pentafluorosulfoxy or phenyl groups (herein, the heterocyclic group represents a ratio of 17 wells, a bite base, N - cerium oxide base, u-density base, oxime, furyl, thienyl, carbazolyl, isoxazolyl, indenyl, thioxyl, isovalent wahyl, succinyl, ϋ 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛 洛Present π-based, tetrahydro-branched or dihydro-branched. ); 16 200836629 Q2 is of general formula (2)
(2) -C6 相^或不同,表示M原子、C1—C6規基、α 基、基、C1—C6鹵烧氧基、Cl—C6烧硫 磺醯基、α—76烧基亞麵基、C1~~C6 i烷基亞 基; 絲石Λ基、Cl-C6姐基磺ϋ基、氰基或确 烷基U可為相同或不同’表示氫原子、自素原子或C1—a 卜C6全氟垸氧基、五氟硫垸基, 原子、峨原子、=自於氫原子、經基、氯原子、>1 同之i個=。基= 鐵C1—C6鹵驅之中相同或不 原子取烧硫基:經擇自於氫原子、經基、氯原子、、、拿 円、/、原子、Cl—C6烷氧基或C1—C6 lir顏其夕由Γ /臭 同之1個以上取代基所取代, m之中相同或不 ^代Cl-C6 _垸基亞石黃醯基:經擇自於 子、/臭原子、硬原子、C1 — C6惊气 、二’、 工基、氣原 同或不同之1個以上取代基所取C6銳氧基之中相 或, 取代C1 — C6鹵烷基磺醯基:姐摆白 溴原子、碘原子、C1—C6烷基、於虱原子、羥基、氯原子、 不同之1個以上取代基所取C6醜氧基之中相同或 通式(i)3i如[1]之殺蟲組成物,其中,以通式⑴表示之化合物,係 A!表示碳原子、氮原子或經氧化之氮原子; 17 200836629 A2、a3、a4表示碳原子; >、I彼此獨立表示氫原子或ci—C4烷基; 1 &彼此獨立表示氧原子或硫原子; XJ為相同減不同,表示氫原子、'、素 η表示〇至4之整數; 人軋甲暴,(2) -C6 phase ^ or different, indicating M atom, C1-C6 group, α group, group, C1-C6 halogen alkoxy group, Cl-C6 sulphur sulfonyl group, α-76 alkyl group, C1~~C6 ialkyl subunit; sulphate, Cl-C6 sulphonyl, cyano or arginyl U may be the same or different 'representing hydrogen atom, self atom or C1—a C6 Perfluorodecyloxy, pentafluorosulfonyl, atom, ruthenium atom, = from hydrogen atom, via group, chlorine atom, >1 with i =. Base = iron C1-C6 halogen drive with the same or non-atomic sulfur-based group: selected from a hydrogen atom, a hydrogen group, a chlorine atom, a ruthenium, an atom, a Cl-C6 alkoxy group or a C1- C6 lir 颜其夕 is replaced by Γ / odor with more than one substituent, m is the same or not ^ Cl-C6 _ 垸 亚 亚 醯 醯 : : :: selected from the child, / stinky atom, hard atom, C1 - C6 stun, two', working group, gas or the same or different one or more substituents taken from the C6 sharp oxygen phase or substituted C1 - C6 haloalkylsulfonyl group: sister white bromine atom , an iodine atom, a C1-C6 alkyl group, an anthracene atom, a hydroxyl group, a chlorine atom, a C6 ugly oxy group which is the same as one or more substituents, or an insecticidal composition of the formula (i) 3i such as [1] A compound represented by the formula (1), wherein A! represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom; 17 200836629 A2, a3, a4 represent a carbon atom; >, I independently represent a hydrogen atom or ci —C4 alkyl; 1 & independently represent an oxygen atom or a sulfur atom; XJ is the same minus, meaning a hydrogen atom, ', prime η represents an integer from 〇 to 4;
Qi表示苯基, 其、基:具有擇自於4素原子、C1 — C4烧基、C1 -C4鹵烧 燒基、C2~C4 烯基、C2 —C4 南烯基、C2 C1-C3 ^氧X C1,基、C3 —C8 環絲、C3—C8 4 環烧基、 二:_基、C1-C3 烧硫基、d-C3 齒 ^ cl- 一C4烷脍其A I 鹵烷基石Kfe基、Cl —C4烷胺基、二C1 幾基、a-基、絲、C1—C4絲基、C1—C4函烧Qi represents a phenyl group, which has a group selected from a 4-atom atom, a C1-C4 alkyl group, a C1-C4 halogen group, a C2~C4 alkenyl group, a C2-C4 south alkenyl group, and a C2 C1-C3^ oxygen group. X C1, group, C3 - C8 ring filament, C3 - C8 4 cycloalkyl, 2: _ group, C1-C3 sulphur group, d-C3 tooth ^ cl- a C4 alkane 脍 AI haloalkyl stone Kfe group, Cl—C4 alkylamino group, di-C1 group, a-group, silk, C1-C4 silk group, C1-C4 letter
Cl—C4 iif基、ci — c4鹵烷羰氧基、C1—C4烷氧羰基、Cl—C4 iif, ci — c 4 halocarbonyloxy, C 1—C 4 alkoxycarbonyl,
Cl—C4 —C4烷羰胺基、C1—C4自烷幾胺基、 五氟魏相烷f:黃醯氧基、芳磺醯氧基、 艾中相同或不同之1個以上取代基, 旅咬k,二ί之雜環基表示ϋ㈣基“喊基、Ν—氧化吼唆基、 i4唑i:噢2基、噻吩基、噚唑基、異噚唑基、噚二唑 咖坐i 1基”塞二°坐基、轉基、♦坐基、三嗤基、 巫其土 = 2,3''二氫一苯并[1.,4]二口号畊基、苯并[13]二噚 吐基、四祕喃基或二氫㈣基。) L ,J ^ 或, ㈣取代雜壤基:具有擇自於鹵素原子、Cl - C4烷基、C1 - C4鹵 C1〜C4烧基、C2—C4稀基、C2—C4鹵烯基、 二7快基、鹵炔基、C3 — C8環烧基、C3 — C8 li環烧 、* 燒氣基、C1 — C3鹵烧乳基、C1 一C3烧硫基、C1 一 C3鹵烧石瓜基尸〜C3燒基亞石黃酿基、C1—產烧基亞續酸基、 C1-C3絲石f si基、α —a鹵絲雜基、a_C4烧胺基、二 18 200836629 C1—C4烷胺基、氰基、硝基、羥基、ci —C4烷羰基、C1 — C4 鹵烧氣基、Cl—C4烧幾氧基、ci一C4鹵烧叛氧基、C1 一C4烧氧 罗厌基、C1 — C4鹵烧乳幾基、C1 一C4烧魏胺基、C1 — C4鹵烧幾胺 基、C1 — C4烧基績醯氧基、C1—C4鹵烷基績醯氧基、芳磺醯氧 基、五氟硫烧基或苯基之中相同或不同之1個以上取代基(在此之 雜環基表示吼呼基、σ比咬基、N—氧化12比咬基、嗜嚏基、塔τι井基、 σ夫喃基、ϋ塞吩基、今峻基、異#嗅基、喝二嗤基、嗟tr坐基、異嗟 唑基、嘆二峻基、吡洛基、咪嗤基、三唑基、ϋ比峻基、四唑基、 2,3 —二氫—苯并[1,4]二今井基、苯并[1,3]二今坐基、四氳σ底喃基 或二氫旅喃基。); Q2為通式(2)Cl—C4—C4 alkylcarbonylamino group, C1-C4 from alkanoamine, pentafluorodivertinane f: xantheneoxy, arylsulfonyloxy, or the same or different substituents in Aizhong, brigade k , a heterocyclic group of ί ϋ 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四塞二°坐基,转基,♦坐基,三嗤基, 巫其土 = 2,3'' dihydro-benzo[1.,4] two slogan, benzo[13] Base, tetramethylene or dihydro (tetra). L , J ^ or, (iv) substituted heterobasic group: having a halogen atom, a Cl - C4 alkyl group, a C1 - C4 halogen C1 - C4 alkyl group, a C2 - C4 dilute group, a C2 - C4 haloalkenyl group, 7 fast radical, haloalkynyl, C3 - C8 cycloalkyl, C3 - C8 li ring burning, * burning gas base, C1 - C3 halogen burning dairy base, C1 - C3 sulfur-burning base, C1 - C3 halogen burning stone melon尸~C3 烧基亚石石基, C1—alkyl sulphonate, C1-C3 stellite f si, α-ahalo, a_C4 arunyl, ss. Amine, cyano, nitro, hydroxy, ci-C4 alkylcarbonyl, C1-C4 halogen-burning gas group, Cl-C4 decyloxy group, ci-C4 halogen-burning oxo group, C1-C4 oxynol , C1 - C4 halogenated calorific acid base, C1 - C4 burned Wei amine group, C1 - C4 halogenated amino group, C1 - C4 alkyl group, oxime, C1 - C4 haloalkyl group, aryl sulfonate One or more substituents which are the same or different among the decyloxy group, the pentafluorosulfoxy group or the phenyl group (herein, the heterocyclic group represents a oxime group, a σ ratio bite group, an N-oxidation 12 ratio bite group, an eosinophilic group) Base, tower τι well base, σ 喃 基 ϋ, ϋ 吩 基 , , , , , , , , , , , , , , , , , , , , , , Tr-based, isoxazolyl, succinyl, pyrrolyl, imidaz, triazolyl, indole, tetrazolyl, 2,3-dihydro-benzo[1,4] The current well, benzo[1,3] octagonal, tetradecyl succinyl or dihydro bromo.); Q2 is of formula (2)
(式中’ Y〗表不C1 ~C4烧綠基、C1 — C4鹵烧裁基、C1 — C4 烧羰氧基、C1-C4鹵烷羰氧基、C1 一C4烷氧羰基、C1 一C4鹵烷 氧羰基、Cl —C4烷羰胺基、C1 — C4鹵烷羰胺基、ci —C4烷基 磺醯氧基、Cl —C4鹵烷基磺醯氧基, 取代C1 — C4烧基:經過擇自於鹵素原子、C1 — C3烷氧基、 C1 — C3鹵烷氧基、C1 — C3烷硫基、C1_C3鹵烷硫基、C1_C3 烧基亞磺醯基、Cl 一 C3鹵烧基亞績醢基、Cl —C3烧基續醢基' C1 — C3鹵垸基石黃醯基、C1 — C4烧胺基、二C1—C4烧胺基、氰 基、石肖基、备基、C1 一C4烧幾基、Cl—C4鹵烧幾基、C1 — C4 ,幾氧基、C1〜C4鹵烷羰氧基、C1 — C4烷氧羰基、C1 一C4鹵烷 基、C1〜C4烷羰胺基、Cl —C4鹵烷羰胺基、ci 一C4烷基磺 酿氧基、C1〜C4鹵烷基磺醯氧基、芳磺醯氧基、五氟硫烷基或烷 基矽烷基之中相同或不同之1個以上取代基所取代; γ5表示4素原子、C1—C6烷基、C1—C6鹵烷基、C1—C6 19 200836629 S氧*烧氧基、C1—C6烧硫基、ci—C6 *燒硫基、 «、a-C6桃基磺祕、氰基或確基; C6烷基石戸' Y2、Y4可為相同或不同,表示氫原子、鹵素原子、Cl_C6 P二3表二C1 —C4鹵烧氧基、C2—C6全I絲、全氣 ; C1-C6 ^ 弗UT丞C6全虱烷軋基、五氟硫烷基, 局;取t1 —C6齒烧氧基:經擇自於氫原子、經基、氯原子、潰 原子、峨原子、Cl —C6烷氧基或Cl —C6 i烷氣其之^、子‘ 同之1個以上取代基所取代, 自紅基之中相同或不 α «' ^ 同之1個以上取代基所取代^ 6 s垸氧基之中相同或不 子、烧基亞石黃酸基:經擇自於氫原子、經基、㈣ 同或不同之1個以上取代基所取代d —C6自絲基之中相 或, 取代C1—C6鹵烷基磺醯基·經摆 漠原子、填原子、c! — C6 土其ς擇祕虱原子、經基、氯原子、 不同之1個以上取代基所取代平)广~C6由燒氧基之中相同或 [4]如[1]之殺蟲組成物,苴 $ 通式,,A】表示碳原子、氮原 ^化合物,係 禹、Α3、入4表示石炭原子; t工乳化之鼠原子, 二、>彼此獨立表示氫原子或c]—c i %彼此獨立表示氧原子或硫原子土 ’ X可為相同或不同,表示氫原’、I 一 11表示0至4之整數· ’、 齒素原子或三氟尹基; Q!表示苯基, 20 200836629 •,代苯基.經擇自於鹵素原子、Cl-C4燒基、Cl-C4鹵烧 基^^代之Cl—U烧基、C2—W烯基、C2—C4 _基、C2 C4自块基、C3~C8環烷基、C3 —C8鹵環烷基、 - 盆、=氧土、C^C3鹵烷氧基、Cl —C3烷硫基、Cl—C3鹵 ’元瓜土、Cl —C3燒基亞磺醯基、C1—C3鹵烷基亞旙醯基、ci — .C3烧基,酸基:C1^C3鹵烧基石黃醯基、C1_C4烧胺基、二C1 •n胺,、,基、確基、減、C1—C4烧絲、ci—c4齒烧 ί基氧基、C1 —C4自題氧基、C1—C4錄幾基、 C1_C4 、C1_C4烧幾胺基、C1—C4鹵烧獄胺基、 • ^氣基、C1 — C4 _烧基石黃醯氧基、芳石黃醯氧基、 中_或獨之1個以上取代基所取代, 口穷二衣二Li之雜每基表示吼呼基“比淀基…—氧化吼咬基、 i夫喃基、β塞吩基、啊基、解絲二唾 土、土〇 土、,、噻唑基、噻二唑基、吡咯基、咪唑基、三唑美、 ^四巧ί其2,3 —二氫—苯并[1,4]二啊基、苯并ίί,3“ 唑基、四虱=喃基或二氫哌喃基。),或, 可 浐某取ίίΪί cf擇自於幽素原子、C1 —C4烷基、C1—C4 _ ^C4=HC4/基、&C4 烯基、C2 —C4 鹵烯基、 • 基、a—ct烷氧美Γΐ块基、C3_C8環烧基、C3—C8i環烷 C3 > Cl "c3 C'7? ^ ' C1~ a -C4烷胺基、氰基、硝美鹵二基;01 -C4烷胺基、二 C4Fhr,碳氧基、C1_C4鹵絲氧基、C1 —C4燒氧 =基、a - C4鹵燒錢基、C1—C4燒羰胺基、C1—c = ί、氧基、C1—C4鹵絲磺醯氧基、“ Η基Μ基塞吩基、糾基、異啊基D縫、♦坐 21 200836629 基、異噻唑基、噻二唑基、吡咯基、咪唑基、三唑基、吡唑基、 四嗤基、2,3-二氫—苯并[1,4]二今井基、苯并[切工噚唑基、四 氳哌喃基或二氳哌喃基); Q2為通式(2)(In the formula, 'Y〗 is not C1 ~ C4 burning green base, C1 - C4 halogen burning base, C1 - C4 burning carbonyloxy, C1-C4 halocarbonyloxy, C1 - C4 alkoxycarbonyl, C1 - C4 Haloalkyloxycarbonyl, Cl-C4 alkylcarbonylamino, C1-C4 haloalkylcarbonyl, ci-C4 alkylsulfonyloxy, Cl-C4 haloalkylsulfonyloxy, substituted C1-C4 alkyl: Selected from a halogen atom, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1_C3 haloalkylthio group, a C1_C3 alkylsulfinyl group, a Cl-C3 halogen alkyl group醢 、, Cl — C 3 烧 醢 ' ' ' C1 — C3 垸 垸 醯 醯 醯 、 、 、 、 、 C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C , Cl—C4 halogenated alkyl, C1-C4, alkoxy, C1-C4 halocarbonyloxy, C1-C4 alkoxycarbonyl, C1-C4 haloalkyl, C1-C4 alkylcarbonyl, Cl— The same or different among C4 haloalkylcarbonylamino, ci-C4 alkylsulfonic acid, C1~C4 haloalkylsulfonyloxy, arylsulfonyloxy, pentafluorosulfanyl or alkyldecylalkyl One or more substituents are substituted; γ5 represents a 4-atom atom, a C1-C6 alkyl group, and a C1- C6 haloalkyl, C1-C6 19 200836629 S oxygen* alkoxy, C1-C6 sulphur-based, ci-C6*sulfuryl, «, a-C6 peach sulfonate, cyano or exact; C6 alkane The base stone 戸 ' Y2, Y4 may be the same or different, meaning hydrogen atom, halogen atom, Cl_C6 P 2 3 table 2 C1 - C4 halogen alkoxy group, C2 - C6 full I wire, total gas; C1-C6 ^ 弗 UT 丞C6 all-decane rolling base, pentafluorosulfanyl group, s.; taking t1 - C6 tooth alkoxy: selected from a hydrogen atom, a trans group, a chlorine atom, a catalyzed atom, a ruthenium atom, a Cl-C6 alkoxy group or Cl—C6 i alkane gas, which is substituted with one or more substituents, the same or not α «' ^ from the red group, substituted with more than one substituent ^ 6 s 垸 oxy The same or a nonionic, pyrenic acid group: substituted by a hydrogen atom, a hydrazine group, a (d) or more than one substituent substituted by d-C6 from the filament group or substituted C1- C6 haloalkylsulfonyl group · swayed by atomic atoms, filled with atoms, c! — C6, which is replaced by a secret atom, a sulfhydryl atom, a chlorine atom, and more than one substituent. An insecticidal composition which is the same in the oxy group or [4] as in [1]苴$ General formula, A] represents a carbon atom, a nitrogen atom, a compound, a ruthenium, a ruthenium 3, a 4 represents a carbon atom; a t-emulsified mouse atom, 2, > independently represents a hydrogen atom or c]-ci % Independent of each other, the oxygen atom or sulfur atom 'X may be the same or different, meaning hydrogenogen', I-11 represents an integer from 0 to 4, ', dentate atom or trifluoro-indenyl; Q! represents phenyl, 20 200836629 •, substituted by phenyl. Selected from halogen atom, Cl-C4 alkyl, Cl-C4 halogenated group, ^-alkyl group, C2-Wene, C2-C4 _ group, C2 C4 From block base, C3~C8 cycloalkyl, C3-C8 halocycloalkyl, - basin, = oxo, C^C3 haloalkoxy, Cl-C3 alkylthio, Cl-C3 halo' Cl—C3 alkyl sulfinyl, C1-C3 haloalkyl fluorenyl, ci — C3 alkyl, acid group: C1^C3 halogenated fluorenylxanthyl group, C1_C4 acryl group, di C1 • n amine, ,, base, deterministic, subtractive, C1-C4 calcined, ci-c4 tooth succinyloxy, C1-C4 self-problem oxy, C1-C4-recording, C1_C4, C1_C4, amino group, C1- C4 halogen burned amine base, • ^ gas base, C1 - C4 _ burnt stone xanthine Aromatic fluorescein, _ or one or more substituents are substituted, and the sulphonyl group of Li is represented by a thiol group.塞 基 基, 啊 基, 解丝二唾土, 土土土,, thiazolyl, thiadiazolyl, pyrrolyl, imidazolyl, triazolam, ^四巧ί, 2,3 - dihydro- Benzo[1,4]diyl, benzo-, 3" oxazolyl, tetradecyl-pyranyl or dihydropyranyl. ), or, may take ίίΪί cf from a crypto atom, C1-C4 alkyl, C1-C4 _ ^C4=HC4/yl, & C4 alkenyl, C2-C4 haloalkenyl, A-ct alkoxy oxime block, C3_C8 cycloalkyl, C3—C8i naphthenic C3 > Cl "c3 C'7? ^ 'C1~ a -C4 alkylamino, cyano, nitro-diyl ; 01 -C4 alkylamino, di C4Fhr, carboxy, C1_C4 halosiloxy, C1-C4 calcination = base, a-C4 halogen burnt group, C1-C4 burnt carbonyl group, C1-c = ί , oxy, C1-C4 halosulfonyloxy, "nonyl fluorenyl thiophene, rectifying, iso-based D-slit, ♦ sitting 21 200836629, isothiazolyl, thiadiazolyl, pyrrolyl, Imidazolyl, triazolyl, pyrazolyl, tetradecyl, 2,3-dihydro-benzo[1,4]dijin, benzo[cutinoxazolyl, tetrahydropyranyl or hydrazine Piperidyl); Q2 is of formula (2)
(2) 心i式中,Yl表示C1—C6烧氧基、Cl - C6鹵烧氧基、α—C6 ίί石mi ^硫基、ci—c6烧基亞顧基、ci—π鹵烧 烧基礦醯基或C1—C6自烧基石黃酿基; 美5表子、—C1—C6烷基、C1—C6鹵烧基、C1—C6烷氧 :C6烷美亞ίίί基、C1 —C6烧硫基、C1 — C6姚硫基、Cl 基、C1:C6 i j^、*C1:C6齒燒基亞石黃酸基、C1 —C6烧基磺酸 I C6鹵烷基磺醯基、氰基或硝基; ^ C1-C6 通式⑴中,[]之心組祕’其中,以通式(1)表示之化合物,係 5表示,子、氮原子或經氧化之氮原子. 2 A3、A4表示碳原子; ’、, ^、汉2彼此獨立表示氣原子或C1 ^(2) In the formula i, Yl represents C1-C6 alkoxy, Cl-C6 halo alkoxy, α-C6 ίί stone mi ^thio, ci-c6 alkyl amide, ci-π halogen burning Base ore sulfhydryl or C1-C6 self-burning basal yellow wine base; US 5 table, -C1-C6 alkyl, C1-C6 halogen alkyl, C1-C6 alkoxy: C6 alkane ίίί, C1 - C6 Sulfur, C1 - C6 Yaothio, Cl, C1:C6 ij^, *C1:C6 dentate tartaric acid, C1-C6 alkylsulfonic acid I C6 haloalkylsulfonyl, cyano Or nitro; ^ C1-C6 In the formula (1), the group of [] is a compound represented by the formula (1), and the formula 5 represents a sub, a nitrogen atom or an oxidized nitrogen atom. 2 A3, A4 represents a carbon atom; ',, ^, and Han 2 are independent of each other to represent a gas atom or C1 ^
Gl、G2彼此獨立表示氧 4烷基; x可為相同或不同,if或硫原子; n表示0至4之整數厂7^原子、_素原子或三氟曱基;Gl, G2 independently of each other represent an oxygen 4 alkyl group; x may be the same or different, if or a sulfur atom; n represents an integer of 0 to 4, 7 atom, _ atom or trifluoromethyl group;
Qi表示笨基, ’ 取代笨基:具擇自於自素 基、赵取代之α-。4烷美二;子、C1—C4烷基、C1-C4鹵烧 C1 一C4炔基、C2-C4鹵炔美、Γ1 C4烯基、C2 —C4鹵烯基、C2 l—C3燒氧基、a-cr4垸氧^燒基、C3—C8鹵環烧基、 虱基、Cl —C3烷硫基、C1 — C3鹵 22 200836629 烷硫基、Cl —C3烷基亞磺醯基、Cl —C3鹵烷基亞續醯基、ci 一 C3烧基石頁醯基、ci—*C3鹵炫基磺醯基、C1 — C4烧胺基、二C1 —C4烧胺基、氰基、硝基、羥基、ci 一C4烧羰基、ci 一C4鹵烧 幾基、C1 一 C4烷羰氧基、C1 — C4鹵烷羰氧基、C1 一 C4烷氧羰基、 C1 — C4 _烷氧羰基、C1 —C4烷羰胺基、C1_C4鹵烷羰胺基、 ^ C1 一C4烧基續醯氧基、C1 — C4鹵烧基石黃醯氧基、芳確醯氧基、 五氟硫烧基或苯基之中相同或不同之1個以上取代基, 雜環基(在此之雜環基表示咕畊基、tj比唆基、N—氧化η比咬基、 嘧啶基、嗒畊基、呋喃基、噻吩基、噚唑基、異噚唑基、噚二唑 • 基、噻唑基、異噻唑基、噻二唑基、吡咯基、咪唑基、三唑基、 °比唑基、四唑基、2,3—二氫一苯并[1,4]二噚呼基、苯并[丨,3]二噚 唑基、四氫哌喃基或二氫哌喃基。), 或, 取代雜環基:具擇自於鹵素原子、Cl —C4烧基、C1 一C4鹵 烧基、經取代之C1 — C4烷基、C2 —C4烯基、C2-C4鹵烯基、 C2—C4炔基、C2 — C4鹵炔基、C3 — C8環烧基、C3 — C8鹵環烷 基、Cl —C3烷氧基、C1 — C3鹵烷氧基、C1_C3烷硫基、α — C3鹵烧硫基、Cl一C3烷基亞磺醯基、Cl一C3鹵烷基亞磺醯基、 ⑩ C1~C3烷基績醯基、C1 一C3鹵烷基確醯基、C1 — C4烷胺基、二 C1 — C4烧胺基、氰基、石肖基、經基、(^一64烧幾基、〇:1 — 〇4 鹵烷羰基、C1 一C4烷羰氧基、C1 一C4鹵烷羰氧基、C1 一 C4烷氧 魏基、C1 一C4鹵烷氧羰基、C1_C4烷羰胺基、C1 — C4鹵烷羰胺 基、C1 一C4烷基續醯氧基、C1 一C4鹵烷基磺醯氧基、芳磺醯氧 基、五氟硫烷基或苯基之中相同或不同之丨個以上取代基(在此之 雜環基表示吡畊基、吡啶基、N一氧化吡啶基、嘧啶基、嗒啡基、 呋喃基、噻吩基、噚唑基、異噚唑基、噚二唑基、噻唑基、^嗟 唾基、嚷一嗤基、吼T7各基、咪嗤基、三嗤基、。比嗤基 '四峻基、 2,3一二氫一苯并[i,4]二噚畊基、苯并[1,3]二噚唑基、四氫哌喃基 或二氫哌喃基。); 23 200836629 Q2為通式(4)Qi means stupid base, ‘substituting stupid base: α- selected from self-primary and Zhao-substituted. 4 alkylene II; sub, C1-C4 alkyl, C1-C4 halogenated C1-C4 alkynyl, C2-C4 haloacetylene, Γ1 C4 alkenyl, C2-C4 haloalkenyl, C2 l-C3 alkoxy , a-cr4 垸 ^ 烧, C3—C8 halocycloalkyl, fluorenyl, Cl—C3 alkylthio, C1-C3 halogen 22 200836629 alkylthio, Cl—C3 alkylsulfinyl, Cl — C3 haloalkyl sulfhydryl, ci-C3 alkyl fluorenyl, ci-*C3 halosulfonyl, C1-C4 acryl, di-C1-C4 acryl, cyano, nitro, Hydroxy, ci-C4 calcined carbonyl, ci-C4 haloalkyl, C1-C4 alkoxycarbonyl, C1-C4 halocarbonyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxycarbonyl, C1- C4 alkylcarbonylamino, C1_C4 haloalkylcarbonyl, ^C1 -C4 alkyl decyloxy, C1 - C4 halogenated fluorenyl fluorenyloxy, aryl decyloxy, pentafluorosulfanyl or phenyl One or more substituents which may be the same or different, a heterocyclic group (herein, a heterocyclic group means a ruthenium base, a tj thiol group, an N-oxygen η ratio octyl group, a pyrimidinyl group, a hydrazine group, a furyl group, a thiophene group Base, carbazolyl, isoxazolyl, oxadiazole, thiazolyl, isothiazolyl, thiadipine Azyl, pyrrolyl, imidazolyl, triazolyl, °, oxazolyl, tetrazolyl, 2,3-dihydro-benzo[1,4]dioxinyl, benzo[丨,3]dioxin Zinyl, tetrahydropyranyl or dihydropyranyl.), or, substituted heterocyclic: optionally selected from a halogen atom, a C—C4 alkyl group, a C1—C4 halogen group, a substituted C1—C4 Alkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, Cl-C3 alkoxy , C1 - C3 haloalkoxy, C1_C3 alkylthio, α - C3 halogen thiol, Cl - C3 alkyl sulfinyl, Cl - C3 haloalkyl sulfinyl, 10 C1 ~ C3 alkyl Sulfhydryl, C1 - C3 haloalkyl, decyl, C1 - C4 alkylamino, di C1 - C4 acryl, cyano, schiffyl, thiol, (^^64), 〇:1 - 〇4 Halocarbonyl, C1 - C4 alkoxycarbonyl, C1 - C4 halocarbonyloxy, C1 - C4 alkoxycarbyl, C1 - C4 haloalkoxycarbonyl, C1 - C4 alkylcarbonylamine, C1 - C4 haloalkylamine , C1 -C4 alkyl decyloxy, C1 -C4 haloalkylsulfonyloxy, arylsulfonyloxy, pentafluorosulfanyl The same or different one or more substituents in the phenyl group (the heterocyclic group here means pyridinyl, pyridyl, N-pyridylpyridyl, pyrimidinyl, morphine, furyl, thienyl, carbazolyl) , isoxazolyl, oxadiazolyl, thiazolyl, oxime, fluorenyl, hydrazine T7, imidazolyl, tridecyl.嗤基基's tetracycline, 2,3-dihydro-benzo[i,4]dioxin, benzo[1,3]dioxazolyl, tetrahydropentanyl or dihydropiperidyl . ); 23 200836629 Q2 is of general formula (4)
Ra⑷ Y4 Rc1Ra(4) Y4 Rc1
( Vi I 基、Cl^可為相同或不同,表示鹵素原子、Cl —〇6烧 烷守美6自燒基、C1一C6烧氧基、C1 一C6 _烧氧基、C1 — 鹵1〜C6 _燒硫基、C1—C6烧基亞磺醯基、C1 — C6 氰酿基、Cl—C6烧基石黃蕴基、C1 一C6鹵烧基石黃醯基、 烷基Y2、Y4可為相同或不同,表示氫原子、鹵素原子、Cl—€6 Ra表示南素原子或羥基; 烷基示氫原子、誠、«原子或Ci-a齒 漠原子或^子^其中之一具有1個以上氫原子、減、氯原子、 & 組成物’其中,通式⑴怜 擇自主物種子用或收穫物用殺蟲組成物,其特徵在於含有 ^通式()表示之化合物中1種或2種以上的化合物作為= (X)n 2(The Vi I group and Cl^ may be the same or different, and represent a halogen atom, a Cl—〇6 alkane Shoumei 6 self-burning group, a C1—C6 alkoxy group, a C1—C6 _ alkoxy group, a C1 — a halogen 1~ C6 _ sulphur-burning group, C1-C6-alkyl sulfinyl sulfonyl group, C1-C6 cyano sulphonyl group, Cl-C6 sulphonyl fluorenyl group, C1-C6 halogenated sulphate sulphate group, alkyl group Y2, Y4 may be the same or different, indicating A hydrogen atom, a halogen atom, or a Cl-€6 Ra represents a south atom or a hydroxyl group; an alkyl group represents a hydrogen atom, an atom, or an atom or a Ci-a tooth atom or a ^^^ having one or more hydrogen atoms, minus , a chlorine atom, a & composition, wherein the formula (1) is a pesticidal composition for seed or harvest, and is characterized by containing one or more compounds of the compound represented by the formula (). As = (X)n 2
N、 R- G2 ⑸ 氮原子或經氧化之 > {式中,Αρ A2、A3、A4各表示碳原子 虱原子, Z表示一isp^SC^Q〗或—叫反灿; 24 200836629 ?、R2彼此獨立表示氫原*、C1—C4絲 G2表不氧原子或硫原子; 烷叛基, 三氟甲^為相同或不同’表7^氫原子、鹵素原子、C1—C3烧基或 η表示〇至4之整數;N, R- G2 (5) Nitrogen atom or oxidized > {wherein, Αρ A2, A3, A4 each represent a carbon atom 虱 atom, Z represents an isp^SC^Q〗 or - called anti-can; 24 200836629 ? R2 independently of each other means hydrogenogen*, C1-C4 filament G2 is a non-oxygen atom or a sulfur atom; an alkyl group, trifluoromethyl is the same or different 'Table 7 ^ hydrogen atom, halogen atom, C1-C3 alkyl or η Indicates an integer from 〇 to 4;
Qi表示苯基,Qi means phenyl,
取代苯基:具擇自於自素原子、C1_C4烷基、d 基、經取代之C1-C4烷基、C2—C4烯基、C2—C4函稀基L =块基,-C4自炔基、C3 __ C8環絲、C3 — C8 _環^基、 1^3烧氧基、Cl-C3函烧氧基、C1_C3烧琉基、a_C3鹵 烷石瓜基、Cl —C3烷基亞磺醯基、C1_C3 -燒基亞續酸基、α — C3絲石黃酸基、C1 —C3 _烧基石黃醯基、C1 —C4烧胺基、二α :C4烷胺基、氰基、硝基、羥基、C1 — C4烷羰基、ci —c4齒烧 羰基、Cl - C4烷羰氧基、ci - C4鹵烧羰氧基、C1 — C4烷氧幾基、 C1 — C4鹵烷氧羰,、C1—C4烷羰胺基、C1_C4 _烷羰胺基、 C1尸C4烧基石頁氧基、ci — c4鹵烧基磺醯氧基、芳石黃醯氧基、 五氟硫烧基、胺基或苯基之中相同或不同之1個以上取代基, p礙環基(在此之碳環基表示萘基、四氫萘基、C3 一 C8環1烧基、 二氫茚基、葬基、9〜側氧基第基、金剛烷基或降福基。),土 取代碳環基··具擇自於鹵素原子、C1 — C4烧基、Cl —C4鹵 烷基、經取代之Cl —C4烷基、C2 — C4烯基、C2 — C4鹵烯基、 C2 C4快基、C2 —C4鹵炔基、C3 —C8環烧基、C3 — C8鹵環垸 基、C1 — C3烷氧基、C1 — C3鹵烷氧基、C1—C3烷硫基、C1 — C3鹵烷硫基、Cl —C3烷基亞磺醯基、Cl —C3鹵烷基亞磺醯基、 Cl C3烧基石頁S&基、C1 — C3鹵烧基石黃酿基、C1 —C4烧胺基、-Cl —C4烷胺基、氰基、硝基、羥基、C1 — C4烷羰基、C1 —C4 鹵烷羰基、Cl — C4烷羰氧基、Cl 一C4鹵烷羰氧基、Cl ~C4燒氧 羰基、C1 — C4鹵烷氧羰基、C1 —C4烷羰胺基、C1 — C4鹵烷緩胺 基、Cl —C4烷基磺醯氧基、C1 — C4鹵烷基磺醯氧基、芳續酿氧 25 200836629 五氟,烷基或苯基之中相同或不同之1個以上取代基(在此之 礙環气表示萘基、四氫萘基、C3—C8環烷基、二氫茚基、第基、 9一側氧基第基、金剛烧基或降福基。), 〜錶環基(在此之雜環基表示吡啡基、吡啶基、氧化咄啶基、 ♦定基、科基、吱喃基、麵基、啊基、異,錢、号二坐 基、嘆唑基、異噻唑基、噻二唑基、吡咯基、咪唑基、三唑基、 吼唾基、四唾基、苯并參坐基、苯并十坐基、苯并咬喃基、▲ 嗟吩基、麵基、異钟基、,緣、異邮基、1H — 基、柳,料錄、四氯^基 或, 取代雜環基:具擇自於_素原子、C1 — C4 、 S C2-C4 ^'C2- 美、Cl r?二:基、C3—㈣烷基、C3-C8 _烷 忘奸炉ϋ,基、C1 —C3 *烧氧基、C1-C3烧硫基、ci-C1 、Λ 絲亞顧基、C1—C3自絲亞顧基、 C1-C4 ^4T^、C1 —C3 幽絲雜基、C1 —C4 烧胺基、二 C1 C4烷胺基、氰基、硝基 、一^ ^ ^ 鹵烧絲、C1—C4沪m π 说基^ 鲈其、Γ1—ΓΜ上ί叛虱基、C1 一 C4鹵烷羰氧基、Cl—C4烷氧 it C1, Cl,烧_基、C1-C4 i燒幾胺 基、五氣炉;C1—C4鹵絲石黃醯氧基、芳石黃酸氧 此&基或本基之中相同或不同之1個以上取代基(在 美ui表不吼呼基、D比咬基、n—氧化°比咬基”密咬基、办井 基、吱喃基、嗟吩基、喝唆基、 井 基、苯并嗟唾基、、巧基、三唆基、対基、四峻 ί并ί Γί 基、異邮基、1Η—異辦基、二ί f )D,4]二㈣基、苯并明二啊基、四氫㈣基或二氮上 26 200836629 q2為苯基; 取代苯基··具擇自於鹵素原子、Cl —C4烷基、Cl —C4鹵烷 基、取代Cl —C4燒基、C2—C4烯基、C2 — C4鹵烯基、C2 — C4 . 炔基、C2一C4自炔基、C3 — C8環烷基、C3 —C8鹵環烷基、C1 一C3烧氧基、C1 — C3鹵烷氧基、C1 — C3烷硫基、C1—C3鹵烷 硫基、C1 一烧基亞績醯基、C1 一C3鹵烧基亞續醯基、C1 — C3 烧基石頁基、C1 一C3鹵烧基磺酸基、ci—*C4烧胺基、二Cl —C4 烷胺基、氰基、硝基、羥基、C1 — C4烷羰基、ci 一C4 i烷羰基、 Cl—C4L氧基、C1 一C4鹵烧幾氧基、C1—C4烧氧幾基、C1 φ —C4鹵烧氧羰基、C1 一C4烷羰胺基、C1 一C4 i|烷羰胺基、C1 一C4烷基磺醯氧基、C1_C4 _烷基磺醯氧基、芳磺醯氧基、五 氟硫烧基或苯基之中相同或不同之1個以上取代基, 碳環基(在此之碳環基表示萘基、四氫萘基、C3 — C8環烷基、 二氫茚基、第基、9 —側氧基苐基、金剛烷基或降福基。), 取代碳環基:具擇自於鹵素原子、C1 一C4烷基、C1—C4鹵 院基、經取代之Cl —C4烷基、C2 — C4烯基、C2 —C4齒稀基、 C2 —C4炔基、C2-C4鹵炔基、C3-C8環烷基、C3 — C8鹵環烷 基、C1-C3烧氧基、C1 — C3鹵烧氧基、C1 — C3烧硫基、ci-C3鹵烧硫基、C1-C3烷基亞磺醯基、C1 一C3鹵烷基亞磺醯基、 攀 C1 一C3烷基石黃醯基、Cl —C3鹵烷基確醯基、ci —C4烷胺基、二 C1 一C3烧胺基、氰基、硝’基、經基、ci — C4燒幾基、ci 一C4 鹵烧羰基、C1-C4烧羰氧基、C1 一C4鹵烧羰氧基、ci~c4烧氧 魏基、ci—C4 i烷氧羰基、C1_C4烷羰胺基、C1—C4 烧幾胺 基、C1:C4烧基磺醯氧基、C1_C4鹵烷基磺醯氧基、芳礦醯氧 基、五氟硫烷基或苯基之中相同或不同之Η固以上取代基(在此之 碳環基表示萘基、四氫萘基、C3一C8環烷基、二氫茚第基、 9一侧氧基第基、金剛烷基或降福基。), 土 雜環基(在此之雜環基表示吼呼基、^比咬基、ν一氧化^比^定基、 嘧啶基、嗒畊基、呋喃基、噻吩基、噚唑基、異噚唑基、噚^嗤 27 200836629 基、噻唑基、異噻唑基、噻二唑基、吡咯基、咪唑基、三唑基、 比1基、四唾基、苯并嗟嗤基、苯并口夸0坐基、苯并吱喃基、苯并 "塞吩基、啥啉基、異喹啉基,卜朵基、異吲哚基、1H—異吲蜂基、 2,3~二氫一苯并[I,4]二今井基、苯并[⑶工噚唑基、四氫哌^旲 或一氮旅喃基。), — 取代雜環基:具擇自於鹵素原子、C1-C4烷基、C1—C4南 烷基、經取代之Cl—C4烷基、C2 — C4烯基、C2 —C4鹵烯基、 C2 C4炔基、C2 —C4鹵炔基、C3 —C8環炫基、C3 —C8南環院 基、C1 — C3烧氧基、C1 一 C3函烧氧基、C1 一 C3燒硫基、d • C3鹵烧硫基、C1 一C3烷基亞磺醯基、Cl一C3鹵烷基亞石黃醯基、 Cl —C3烧基績醯基、ci — C3 iS烧基確醯基、C1 — C4烧胺基、二 C1~C4烷胺基、氰基、硝基、羥基、C1 — C4烷羰基、C1 — c4 鹵燒魏基、Cl 一C4烷羰氧基、Cl-C4鹵烷羰氧基、Cl —C4烷氧 幾基、C1—C4 i烷氧羰基、α 一C4烷羰胺基、C1_C4 _烷羰胺 基、C1-C4烷基續醯氧基、ci 一C4鹵烷基磺醯氧基、芳磺醯氧 基、五氟硫烷基或笨基之中相同或不同之〗個以上取代基(在此之 雜環基表示吡畊基、吡啶基、N_氧化咄啶基、嘧啶基、嗒畊基、 呋喃基、噻吩基、喝唑基、異噚唑基、噚二唑基、噻唑^^嗟 坐基、嗟一嗤基、ϋ比嘻基、喘哇基、三嗤基、η比嗤基、四唾基、 笨并噻唑基、苯并噚唑基、苯并呋喃基、苯并噻吩基、喹啉基、 異喹啉基、吲哚基、異吲哚基、1Η—異吲哚基、2,3 —二氫—苯并 [I,4]二今井基、苯并[丨,3]二噚唑基、四氳哌喃基或二氫哌喃基。), Cl—C6烷基,或 取代C1—C6烷基··具擇自於鹵素原子、C1 — C4鹵烷基、C2 —C4烯基、C2 —C4 i烯基、C2-C4炔基、C2-C4鹵炔基、C3 :C8環烧基、C3 — C8鹵環烷基、Cl—C3烷氧基、C1 一C3鹵烷 氧基、C1—C3烷硫基、C1 — C3鹵烷硫基、C1 — C3烷基亞石黃醯基、 C1 — C3鹵烷基亞磺醯基、C1 — C3烷基續醯基、C1 — C3鹵烷基磺 醯基、C1 — C4烷胺基、二C1 —C4烷胺基、氰基、硝基、羥基: 28 200836629 C1-C4垸幾基、C1 —C4鹵烷幾基、ci—c 函,氧基、C1-C4 垸氧縣、α —c4 、C1-C4 烧羰胺基、C1—C4鹵餘靜λμ 元乳叛基、Cl—C4 ^ ' Cl-C4 同之1個以上取代基}。 鼠瓜烷基或本基之中相同或不 項之Ϊ蟲其特徵在於猶述⑴〜⑺中任-項之殺蟲組成觸其特徵在於:使前述⑴〜m中任一 對種其^接觸植物種子之方法,為 mi二T1 土抹處理、浸泡處理或粉衣處理。 ,、稻、甜菜、小麥、大麥、向日葵、 馬鈴薯、甘藷、之種字卓食百人之種子’芋頭、 [12]如前述间之預防方、口,至曰之球根。 麵物鮮:伽 中任=====子其特徵在於:將前_〜[7] ::子之 _ 燻蒸燻煙處理。 土布處里π泡處理、粉衣處理或 -項將前糊,中任 處理、燻蒸燻煙處理或加屋注入。 〜包處理叔衣 依,、、、本發明’缺供對於働種子或農業獅之魏物產生 29 200836629 之棘°顯不南預防效果之殺蟲組成物及各種蟲害之預防方法。 【貫施方式】 (實施發明之最佳職) 之整下^t發轉加綱。赋+,「Ca—Cb(a、b表亍1以上 意指碳原子數1〜3個, —J表示正(n〇nnaD f C4」表示破原子數1〜4個》又,「η 弟二」表示第三(tertiaiy)。 」表不弟外―)、 「幽素原子原子」及各「基」之具體例如以下所示。 原子、氯原子、溴原子或硬原子。 基等直鏈狀例如/甲基、乙基、正喊、異丙基、環丙 三丁基等’例如,正丁基、第二丁基、異丁基、第 烷基」,除了 碳原子數1〜4個之院基,「C1—C6 ^ ^ ^ ^ 2-^ . 3- C4齒烷基、」_^取f基,例如:鹵素原子、d — C4鹵炔基、C3sC8jm "二鹵烤基力—以炔基、。— C1 —C3 ώ俨 衣烷基、C3 — C8鹵環烷基、€1_€3烷氧基、 烷基亞磺^、m=硫基、α—〇緣硫基、ci—ο Cl-C3幽燒基罐献、Ci-C3絲賴基、 基、硝基、C C4 _基、二C1—C4烧胺基、氰 絲氧基、CltC4自4烧C1 —C4鹵職基、Cl-C4 氧羰基、C^C4 ==、Cl-C4烷氧羰基、Cl-C4 4烷 醯氧基、ci〜C4 C4 S烧叛胺基、C1_C4烷基石黃 基。取代C1〜CM ?^*基~醯氧基、芳磺醯氧基、五氟硫烷基或苯 C4燒基’具有擇自於該等之相同或不同之1個以上 30 200836629 取代基。 單氯鹵田ΐ基」例如,單氟曱基、二氟曱基、三I曱基、 $虱曱 '、—乳甲基、二氯甲基、單漠甲基、二漠甲基、三 二氯乙H2—ί乙基、2,2—二氟乙基、2,2,2—三氟乙基、1 〇土 2一虱乙基、2,2 —二氯乙基、2,2,2—三氯乙基、〗—淳 溴乙基、2,2—二溴乙基、如―三溴乙基、2—碘乙基、、 土、3—氟一正丙基、3一氯一正丙基、3一溴一正丙基、 1一斤氣〜丙基、1,3 一二氯一2—丙基、l1,1 一三氟—2〜丙基、 _丙基 美 ' 土、2,2,3,3,3 —五氟一正丙基、七氟一異丙 ^不ir正丙基、卜漠—u,2,3,3,3—六氟_2_丙基等經過相 . 1個以上鹵素原子取代之直鏈狀或分支鏈狀碳原子數 「C1—C4 s燒基」’除「ci—c3函燒基」以外尚 =不:氣—正丁基、九氣-正丁基、九氣-2-丁基等S 數lif之Λ1個二上*素原子取代之直鏈狀*分支鏈狀碳原子 =26,6 —三氟正己基、九氟-正丁基、九氟-2-丁基等 原^數tfH1。似上自辆子取代之直織或分支鏈狀碳 媒麟ίίϊ4稀基」例如,乙稀基、烯丙基、2—丁烯基、3-丁 二广鏈m子數2〜4之烯基’「c2—c4 4烯基」 之 丁 === 上 甲例如,块丙基、卜丁块—3-基、卜丁块 2〜4之二,^中具參鍵之直鏈狀或分支鏈狀碳原子數 原子取代ΐ石户鏈中:^絲」例如經相同不同之1個以上鹵素 猶中具麥鍵之直鏈狀或分支鍵狀碳原子數2〜4之块 31 200836629 基。 基環^基^環丙基、環丁基、環戊基、2-甲 子數3〜8 ^庚基等《狀構造之碳原 基、2-氯環己λ 8 ’烧基」例如2,2,3,3-四氟環丁 素原子取代之ί/狀·^ f等經具綱或相異之1個以上鹵 「C1 ^ 5構造讀子數3〜8之環烷基。 氧基等直鏈狀或:^^ ’甲&基二丙氧基、異丙 氧基」除了「Cl-C3 ^軒數1 3之垸氧基,「C1—C4烧 或分支鏈狀碳原子數1〜4 ϋ如二2:丁氧基等直鏈狀 氟甲氧基、1,1 2—:氟乙气C3 *烷氧基」例如三 -三氣乙氧基、,似H六氟—2—丙氧基、2,2,2 氧基、1 1 2 m? 氟—正丙氧基、U,2,2—四氟乙 Ϊί代iSi·:ί麟氧鮮經_衫同之Η該上岭原 支鏈狀碳原子數1〜3之銳氧基,「Cl—C4 ί 3 *燒氧基」以外,有例如,3一 二ΐ,3,3,4,4,4—八氟—2 —丁氧基等經相同或不Ϊ ^^上4素原子取代之直鏈狀或分支鏈狀縣子數1〜4之^ ㈣硫基」例如,甲硫基、乙硫基、正丙硫基、里丙 Ιΐϊΐ ίΐ鍵狀或分支錄碳原子數1〜3之燒硫基,;C1 =4烧硫基」除「C1 — C3烧硫基」以外,有例如,正丁硫基、 又支鏈Ϊ石第三丁硫基、_基甲硫基等直鏈狀或 刀支鏈狀石反原子數1〜4之烧硫基,「C1_C6烧硫基」除、 基心'外列如’正戊硫基、正己硫基等直鏈狀或分支 鏈狀故原子數1〜6個之烧硫基。 「C1 — C3鹵烷硫基」例如,三氟甲硫基、五氟乙硫基、 敦乙硫基、2,2,2—-三氟乙硫基、七氟—正丙硫基、七氣—異丙炉 基],1,2,2-四氟乙硫基、^2,3,3,3 —六氟丙硫基等經過相同^ 不同之1似上較原子取狀直鏈狀或分支鏈狀碳原子數Μ 32 200836629 之烧硫基’「C1-C4鹵垸硫基除「C1 例如,九氟-正丁硫基、九氣」_4二 ==3 基」f外,有 硫基等經過相同或不同之丨個以 ,4,4—二鼠—正丁 鏈狀碳原子數1〜4之紗A,「rj素軒取代之鏈狀或分支 .烧硫基」以外’有例如^氟—正戊:6基鹵㈡ 以上咖子取代之直鏈狀或分支以原: 其、不亞石黃酿基」例如’甲基亞石黃酸基、乙基亞麵 ^分支f喊亞磺縣、辆基亞雜基等直鏈 ΪΪ: =:3〜3之烷基亞磺酸基,「C1 -C6烷基亞錯 i! 丁f基亞磺醢基」以外’有例如’正丁基亞石黃醯 土弟一丁基亞石頁醯基、正戊基亞石黃酿基、正己美亞於醎装榮士 鏈狀,分支鏈狀碳原子數丨〜6之絲亞磺酸基。1 μ 土專直 r其ϋ1^3姐基亞^絲」例如’三氟曱基亞雜基、五氟 其土 :〜、2,2,2—三氣乙基亞磺醯基、七氟—正丙基亞碏醯 fT二t—i丙基料醯基、u,2,2—四氟乙基亞續酿基 ,,,W — /、氟丙基亞磺醯基等經過相同或不同之i個以上 1取!^5鏈狀或分支雜碳原子數1〜3之絲亞確酿基’,、 C1-C6鹵烧基亞石黃醯基」除rcl —ο _垸基亞磺醯基」以 有例^,九氟-正丁基亞石黃醯基、九就_ f二丁基亞石雜基、4,4 4 :氟一正丁基亞確醢基、全氟一正戊基亞續醯基、全氟正己吴 亞石男&&基等經過相同或不同之1個以上鹵素原子取代之直大 分支鏈狀碳原子數1〜6之烷基亞磺醯基。 或Substituted phenyl: optionally derived from a self atom, a C1_C4 alkyl group, a d group, a substituted C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 functional group L=block group, a -C4 alkynyl group , C3 __ C8 cyclofilament, C3 - C8 _ ring ^ base, 1 ^ 3 alkoxy, Cl-C3 functional alkoxy, C1_C3 decyl, a_C3 halocarbazide, Cl - C3 alkyl sulfin Base, C1_C3 - alkyl sulphonate, α - C3 sulphate, C1 - C3 _ sulphur sulphate, C1 - C4 acryl, bis: C4 alkylamino, cyano, nitro, hydroxy , C1—C4 alkylcarbonyl, ci—c4 tooth carbonyl, Cl—C4 alkylcarbonyloxy, ci—C4 halogen carbonyloxy, C1-C4 alkoxy, C1-C4 halooxycarbonyl, C1- C4 alkylcarbonylamino, C1_C4-alkylcarbonylamine, C1 cadaverine C4 alkyl sulfonate, ci-c4 halosulfonyloxy, aryl sulfoxide, pentafluorosulfanyl, amine or benzene One or more substituents which are the same or different in the group, p a ring group (here, a carbocyclic group represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 ring 1 alkyl group, a dihydroindenyl group, a burial group, 9 ~Sideoxydiyl, adamantyl or ruthenium.), soil-substituted carbocyclic group · selected from halogen Atom, C1-C4 alkyl, Cl-C4 haloalkyl, substituted C1-C4 alkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2 C4 fast radical, C2-C4 haloalkynyl, C3 —C8 cycloalkyl, C 3 —C 8 halocycloalkyl, C 1 —C 3 alkoxy, C 1 —C 3 haloalkoxy, C 1—C 3 alkylthio, C 1 —C 3 haloalkylthio, Cl —C 3 alkyl Sulfonyl, Cl-C3 haloalkylsulfinyl, Cl C3 alkyl sulphide S& base, C1 - C3 halogenated sulphur base, C1-C4 arunyl, -Cl-C4 alkylamine, cyanide Base, nitro, hydroxy, C1-C4 alkylcarbonyl, C1-C4 halocarbonyl, Cl-C4 alkylcarbonyloxy, Cl-C4 halocarbonyloxy, Cl~C4 alkoxycarbonyl, C1-C4 haloalkoxy Carbonyl group, C1-C4 alkylcarbonylamino group, C1-C4 haloalkyl slow amine group, Cl-C4 alkylsulfonyloxy group, C1-C4 haloalkylsulfonyloxy group, aromatic continuous brewing oxygen 25 200836629 pentafluoro, alkane One or more substituents which are the same or different among the phenyl groups or the phenyl groups (here, the ring gas represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, a dihydroindenyl group, a aryl group, and a 9-side oxygen group).第基基, 金刚烧基或降福基.), 〜表环基(在此Cyclic group means pyridyl, pyridyl, oxalyldinyl, ♦ group, keyl, fluorenyl, quinone, argyl, iso, m, sylylene, oxazolyl, isothiazolyl, thiazepine Azyl, pyrrolyl, imidazolyl, triazolyl, oxime, tetrasal, benzoxanthene, benzoxanthyl, benzoxanyl, ▲ porphinyl, face group, heteronym ,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, Cl r? 2: base, C3 - (tetra) alkyl, C3-C8 _ alkaloid furnace, base, C1 - C3 * alkoxy, C1-C3 sulfur-burning, ci-C1, 丝丝亚基基, C1-C3 from A. sylvestris, C1-C4^4T^, C1-C3 filegyl, C1-C4 acryl, di-C1 C4 alkylamino, cyano, nitro, one ^^^ Silk, C1—C4, Shanghai, m π, base, 鲈, Γ1—ΓΜ上·, 虱, C, C, 虱, 虱, C, C, C, C, C, C, C, Cl, Cl, Burning amine-based, five-gas furnace; C1-C4 halogen-silica xanthine, arsenic acid oxygen, the same or different ones in the base or the base Daiji (in the United States ui table does not call the base, D than bite base, n-oxidation ° bite base) dense bite base, do well base, 吱 基 base, 嗟 基 、, 唆 base, well base, benzo嗟 基 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Base, tetrahydro (tetra) or dinitrogen 26 200836629 q2 is phenyl; substituted phenyl · selected from halogen atom, Cl - C4 alkyl, Cl - C4 haloalkyl, substituted Cl - C4 alkyl, C2 —C 4 alkenyl, C 2 —C 4 haloalkenyl, C 2 —C 4 . alkynyl, C 2 —C 4 alkynyl, C 3 —C 8 cycloalkyl, C 3 —C 8 halocycloalkyl, C 1 —C 3 alkoxy, C 1 — C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1, an alkyl, a C1, a C3, a halogen, a sulfhydryl, a C1 - C3, a sulphate, a C1 a C3 halogenated sulfonic acid group, ci-*C4 acrylamine group, diCl-C4 alkylamino group, cyano group, nitro group, hydroxyl group, C1-C4 alkylcarbonyl group, ci-C4 i-alkylcarbonyl group, Cl-C4L oxygen Base, C1 - C4 halogenated oxy group, C1-C4 aerobic group, C1 φ - C4 halogenated oxycarbonyl, C1 - C4 Alkylcarbonylamino, C1 -C4 i|alkylcarbonylamino, C1 -C4 alkylsulfonyloxy, C1_C4-alkylsulfonyloxy, arylsulfonyloxy, pentafluorosulfanyl or phenyl One or more substituents which may be the same or different, a carbocyclic group (wherein the carbocyclic group represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, a dihydroindenyl group, a aryl group, a 9-side oxime group) Base, adamantyl or ruthenium. Substituted carbocyclic group: selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 halogen-based group, a substituted Cl-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 dentate group, C2 —C 4 alkynyl, C 2 -C 4 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 —C 8 halocycloalkyl, C 1 -C 3 alkoxy, C 1 —C 3 halo alkoxy, C 1 —C 3 sulphur, ci -C3 halogenated sulfur group, C1-C3 alkyl sulfinyl group, C1 - C3 haloalkyl sulfinyl group, C1 - C3 alkyl fluorenyl group, Cl - C3 haloalkyl group, ci - C4 alkane Amine group, di C1 - C3 acrylamine group, cyano group, nitro group, thiol group, ci-C4 group, ci-C4 halogen carbonyl group, C1-C4 carbonyloxy group, C1-C4 halogen carbonyl oxide Base, ci~c4 calcined weigen, ci-C4 i alkoxycarbonyl, C1_C4 alkylcarbonylamine, C1-C4 succinylamine, C1:C4 alkylsulfonyloxy, C1_C4 haloalkylsulfonyloxy The same or different oxime substituents in the aryloxy group, pentafluorosulfanyl group or phenyl group (wherein the carbocyclic group represents a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, two Hydroquinone, 9-oxyl, adamantyl or ruthenium.), soil heterocyclic (here The ring group represents a oxime group, a thiol group, a ν-oxygen group, a pyridyl group, a pyridyl group, a furyl group, a thienyl group, a carbazolyl group, an isoxazolyl group, a thiol group, and a thiazole. Base, isothiazolyl, thiadiazolyl, pyrrolyl, imidazolyl, triazolyl, specific 1 group, tetrasyl, benzofluorenyl, benzoxanthene, benzofuranyl, benzo "Sepeno, porphyrin, isoquinolinyl, bromo, isodecyl, 1H-isoindole, 2,3~dihydro-benzo[I,4]二今井基,苯And [(3) oxazolyl, tetrahydropiperidinium or mononitrocarbamic acid.), substituted heterocyclic group: selected from halogen atom, C1-C4 alkyl group, C1-C4 south alkyl group, substituted Cl—C4 alkyl, C 2 —C 4 alkenyl, C 2 —C 4 haloalkenyl, C 2 C 4 alkynyl, C 2 —C 4 haloalkynyl, C 3 —C 8 cyclodyl, C 3 —C 8 South ring, C 1 —C 3 Oxy, C1 - C3 functional alkoxy, C1 - C3 sulphur, d · C3 halogen thiol, C1 - C3 alkyl sulfinyl, Cl - C3 haloalkyl sulphate, Cl - C3 Base 醯 、, ci — C3 iS alkyl base, C1 — C4 amine group, two C1~C 4 alkylamino, cyano, nitro, hydroxy, C1-C4 alkylcarbonyl, C1 - c4 halogenated thiol, Cl-C4 alkylcarbonyloxy, Cl-C4 halocarbonyloxy, Cl-C4 alkoxy , C1-C4 i alkoxycarbonyl, α-C4 alkylcarbonylamino, C1_C4 _alkylcarbonylamino, C1-C4 alkyl decyloxy, ci-C4 haloalkylsulfonyloxy, arylsulfonyloxy The same or different substituents among the groups, pentafluorosulfanyl groups or stupid groups (herein, the heterocyclic group means pyridinyl, pyridyl, N-oxaridinyl, pyrimidinyl, hydrazine, Furanyl, thienyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolidine, fluorenyl, fluorenyl, whipyl, tridecyl, η thiol, Tetrasinyl, stupid and thiazolyl, benzoxazolyl, benzofuranyl, benzothienyl, quinolyl, isoquinolinyl, fluorenyl, isodecyl, 1 Η-isodecyl, 2,3-dihydro-benzo[I,4]dipin, benzo[丨,3]dioxazolyl, tetrahydropyranyl or dihydropyranyl. , a Cl—C6 alkyl group, or a substituted C1-C6 alkyl group, selected from a halogen atom, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 i alkenyl group, a C2-C4 alkynyl group, C2-C4 haloalkynyl, C3: C8 cycloalkyl, C3 - C8 halocycloalkyl, Cl-C3 alkoxy, C1 - C3 haloalkoxy, C1-C3 alkylthio, C1 - C3 haloalkyl , C1 - C3 alkyl sulphate, C1 - C3 haloalkyl sulfinyl, C1 - C3 alkyl fluorenyl, C1 - C3 haloalkyl sulfonyl, C1 - C4 alkylamino, C1 —C4 alkylamino, cyano, nitro, hydroxy: 28 200836629 C1-C4 fluorenyl, C1-C4 haloalkyl, ci-c, oxy, C1-C4 oxime, α-c4, C1-C4 is a carbonylamine group, a C1-C4 halogen residue, a ruthenium group, and a Cl-C4^'Cl-C4 group having one or more substituents}. The same or none of the aphids in the murine alkyl group or the base is characterized in that the insecticidal composition of any of the items (1) to (7) is characterized by: contacting any one of the above (1) to m The method of plant seeds is mi 2 T1 soil treatment, soak treatment or powder coating treatment. , rice, sugar beet, wheat, barley, sunflower, potato, sweet potato, the seeds of the seeds of a hundred people, 'Taro, [12] as in the prevention of the above, mouth, to the root of the ball. Fresh noodles: gamma Ren ===== Sub-characteristics: It treats the former _~[7]::子子_ fumigation fumigation. In the earthen cloth, π bubble treatment, powder coating treatment or - item will be paste, medium treatment, fumigation fumigation or room injection. 〜包处理叔衣 依,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, [Common application method] (the best position for implementing the invention) Assign +, "Ca-Cb (a, b indicates that 1 or more means that the number of carbon atoms is 1 to 3, -J means positive (n〇nnaD f C4" means the number of broken atoms is 1 to 4", and "η" The second is the third (tertiaiy). The table is not the other one--, the "ceto atom" and the "base" are as follows. Atom, chlorine, bromine or hard atom. For example, /methyl, ethyl, yoke, isopropyl, propylene butyl, etc. 'e.g., n-butyl, t-butyl, isobutyl, alkyl", except for carbon atoms 1 to 4 The base of the house, "C1—C6 ^ ^ ^ ^ 2-^ . 3- C4 dentate alkyl, " _ ^ f base, for example: halogen atom, d - C4 haloalkynyl, C3sC8jm " dihalide - alkynyl, -C1 - C3 decyl, C3 - C8 halocycloalkyl, €1_3 alkoxy, alkyl sulfinyl, m = thio, alpha - sulfhydryl , ci—ο Cl-C3 kiln base, Ci-C3 lysine, base, nitro, C C4 _ group, two C1-C4 amine group, cyanide group, CltC4 from 4 burning C1 - C4 Halogen, Cl-C4 oxycarbonyl, C^C4 ==, Cl-C4 alkoxycarbonyl, Cl-C4 4 alkoxy, ci~C4 C4 S Tertamine, C1_C4 alkyl sulphate. Substituting C1~CM?^*yl-nonyloxy, arylsulfonyloxy, pentafluorosulfanyl or benzene C4 alkyl' has the same or different One or more 30 200836629 Substituents. Monochlorohalide sulfhydryl groups, for example, monofluoroindolyl, difluoroindolyl, tri-indolyl, 虱曱', y-methyl, dichloromethyl, mono Methyl, dimethyl methyl, trichloroethylene H2-ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 2 2 虱 ethyl, 2, 2 —dichloroethyl, 2,2,2-trichloroethyl, 淳-bromoethyl, 2,2-dibromoethyl, such as tribromoethyl, 2-iodoethyl, earth, 3 —Fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-p-propyl, 1 kg-propyl, 1,3-dichloro-2-propyl, l1,1-trifluoro- 2~propyl, _propylmei' soil, 2,2,3,3,3-pentafluoro-n-propyl, heptafluoro-isopropyl^not ir-propyl, pu-u, 2,3, 3,3-hexafluoro-2-propyl group, etc., a linear or branched chain of carbon atoms substituted by one or more halogen atoms, "C1-C4 s alkyl", except for "ci-c3 functional base" Outside = no Gas-n-butyl, non-n-butyl-n-butyl, non-n-butyl-2-butyl, etc. S number lif Λ 1 bis-*-atom substituted straight chain * branched chain carbon atom = 26,6 - trifluoro N-hexyl, nonafluoro-n-butyl, nonafluoro-2-butyl and the like tfH1. It seems to be a straight-woven or branched-chain carbon-based lining of a carbon-based alloy. For example, ethylene or alkene Propyl, 2-butenyl, 3-butadiene-chain wide-chain m-number 2~4 alkenyl '"c2-c4 4 alkenyl" butyl === upper arm, for example, block propyl, bubut block - 3-base, butyl block 2 to 4 bis, ^ in the linear or branched chain of carbon atoms with a reference to replace the fluorite chain: ^ silk", for example, the same different one or more halogens A block having a linear or branched bond carbon number of 2 to 4 in the middle of a wheat bond 31 200836629. a ring-like propyl group, a cyclobutyl group, a cyclopentyl group, a 2-methyl group number of 3 to 8 ^heptyl group, and the like, a carbon-based carbonyl group, a 2-chlorocyclohexane λ 8 'alkyl group, for example, 2, 2,3,3-tetrafluorocyclobutane atom substituted by ί / 状 · ^ f such as one or more different halogens "C1 ^ 5 structure reader number 3 ~ 8 cycloalkyl. Oxy Or a straight chain or: ^^ 'A & yldipropoxy, isopropoxy" In addition to "Cl-C3 ^ 数 1 3 decyloxy, "C1 - C4 burned or branched chain carbon number 1~4 For example, 2: a linear fluoromethoxy group such as a butoxy group, a 1,1 2:fluoroethylene C3*alkoxy group such as a tris-trisethoxy group, and a H-hexafluoro group. 2-propoxy, 2,2,2 oxy, 1 1 2 m? Fluorine-n-propoxy, U, 2,2-tetrafluoroethylene i iSi·: 麟麟氧鲜经_ 衫同Η The amphoteric acid having a branched chain of 1 to 3 carbon atoms, and "Cl-C4 ί 3 * alkoxy group", for example, 3, 2, 3, 3, 4, 4, 4 - 8 a linear or branched chain number of 1 to 4 of a fluorine- 2 -butoxy group substituted by the same or a 4-substituted atom, such as a methylthio group, an ethylthio group, N-propylthio, propyl propionate a sulfur-burning group having a carbon number of 1 to 3, or a C1 = 4 sulfur-burning group, in addition to a "C1 - C3 sulfur-burning group", for example, n-butylthio group and branched-chain vermiculite a sulfur- or s-methylthio group such as a sulphur-based group having a reverse atomic number of 1 to 4, such as a "C1_C6 sulfur-burning group", and a base column such as a 'n-pentylthio group, a positive one. A sulfur-based group or the like having a linear or branched chain shape and having 1 to 6 atomic numbers. "C1 - C3 haloalkylthio", for example, trifluoromethylthio, pentafluoroethylthio, thioethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, seven Gas-isopropyl furnace base], 1,2,2-tetrafluoroethylthio group, ^2,3,3,3-hexafluoropropylthio group, etc. Or the number of branched chain carbon atoms Μ 32 200836629 The sulfur-burning group 'C1-C4 halogen thiol group except C1, for example, nonafluoro-n-butylthio group, nine gas _4 two ==3 base" f A sulphur-based group or the like which has the same or different enthalpy, 4,4 - 2 - y-n-chained carbon atoms having a carbon number of 1 to 4, "rj-xuan replaced by a chain or a branch. For example, there is a linear or branched branch of the above-mentioned fluoro-n-pentyl group: 6-based halogen (2). The original: it is not a stone-branched base, for example, 'methyl linoleic acid group, ethyl sub-surface ^ branch f Shouting the linear chain of the sulfinamide, the carcinogen, etc.: =: 3 to 3 alkyl sulfinate, "C1 - C6 alkyl sub-error i! D-f-sulfinyl" For example, 'n-butyl sulphite, scorpion scorpion, butyl sulphite, n-pentyl sulphate, and yin Meiya Shi-chain, branched-chain carbon number of Shu Siya ~ 6 of a sulfonic acid group. 1 μ soil straightening r ϋ 1^3 sister Kea ^ silk" such as 'trifluoromethyl sulfenyl, pentacene: ~, 2, 2, 2 - tri-glyethyl sulfinyl, heptafluoro - n-propyl fluorene fT di t-i propyl sulfhydryl, u, 2, 2 - tetrafluoroethyl hydrazine,, W - /, fluoropropyl sulfinyl, etc. Different i or more 1 take! ^5 chain or branched heterocarbon atom number 1~3 of the silk of the arginine base,, C1-C6 halogenated sulphate yttrium group "except rcl - ο 垸 sulfinyl sulfhydryl" by example ^, nine Fluorine-n-butyl sulphate sulphate, sulphate _f dibutyl sulphate, 4,4 4: fluoro-n-butyl ylidene, perfluoro-n-pentyl sulfhydryl, perfluorinated An alkyl sulfinyl group having 1 to 6 straight-chain branched carbon atoms substituted by the same or different one or more halogen atoms, such as Wu Yashi male &&>. or
Cl C3烧基石頁酿基」例如’曱基石黃酿基、乙基石黃酸基、正 丙基確醯基、異丙基磺醯基、環丙基石黃酿基等直鏈狀或分支鏈 之碳原子數1〜3之烷基磺醯基,「C1 — C6烷基磺醯基」除、「α 一C3烧基石黃釀基」以外,例如,正丁基石黃酿基、第三丁基石黃酸美 正戊基磺醯基、正己基磺醯基等直鏈狀或分支鏈狀碳原^數 之烷基磺醯基。 〜 33 200836629 #且二 基續醯基」例如,三氟甲基顧基、五氟乙其 ί:ΐ—二氟乙基磺醯基、七氟一正丙基磺《、七氟土 異丙基响基、U,2,2-四氟乙基俩基、〗 六= 令鏈狀故原子數1〜3之絲磺醯基,「C1_C6鹵垸基瑞釀美二 鹵烧基磺醯基」以外,有例如,九氟—正丁基错^于、 九,2二丁基石錄基、4,4,4 —三氟—正丁基石練基、全二 戊基雜基、全氟正己基磺醯基等觸_或不社丨個以 素原之?1鏈狀或分支鏈狀碳原子數1〜6之絲續醯基。自 + 芳%、fe氧基」例如,苯基磺醯氧基、對甲苯石黃醯 〜 蔡,石^氧^、2—萘基俩氧基、蒽基雜氧基、菲基麵氧基、 -風,基、麵氧基等具料環之碳原子數6〜14之芳錯酸美。 「C1 — C4烷胺基」例如,曱基胺基、乙基胺基、正丙基胺^ ίΐίΐί叙冗餘基、環丙基胺基等直鏈狀或分支鏈狀i環 狀之妷原子數1〜4之烷胺基,「二C1 — C4烷胺基」例如,二甲 胺基、二乙基絲、N_乙基—N—甲基胺基等經姻或不同之1 個直鏈狀或分支鏈狀碳原子數1〜4之烧基取代之胺基。 「C1—C4全氟烷基」例如,三氟甲基、五氟乙基、七氟—正 丙基I七氟Γ異丙基、九氟—正丁基、九氟―2—丁基、九氟-異 丁基等經過氟原子全部取代之直鏈狀或分支鏈狀碳原 絲,「〜C6全紐基」例如,五氟乙基、七^ = 異丙基、九氟~正丁基、九氟_2_丁基、九氟一異丁基、十 一氟一正戊基、十三氟正己基等經過氟原子全部取代之直鏈狀或 分支鍵狀碳原子數2〜6之烧基。 ^ C1 — C6全氟烧硫基」例如,三氟甲硫基、五氟乙硫基、七 ^一正丙硫基、七氟一異丙硫基、九氟一正丁硫基、九氟一2_丁 硫基二九氟一異丁硫基、十一氟—正戊硫基、十三氟正己硫基等 經過氟原子全部取代之直鏈狀或分支鏈狀碳原子數丨〜6之烷硫 基。 34 200836629 ^ 「C1-C6全氟烷基亞磺醯基」例如,三氟曱基亞磺醯基、五 氟乙基,磺醯基、七氟一正丙基亞磺醯基、七氟一異丙基亞磺醯 基、九^二正丁基亞磺醯基、九氟—2 —丁基亞磺醯基、九氟一異 丁费亞基、十一氟一正戊基亞續酿基、十三氟正己基亞續酿 基等經過敦原子全部取代之直鏈狀或分支鏈狀碳原子數丨〜6之烷 基亞續醯基。 全氟烧基磺醯基」例如,三氟甲基磺醯基、五氟乙 土磺七氟—正丙基磺醯基、七氟—異丙基磺醯基、九氟— =基雜基、九氟—2—τ基雜基、九氟_異丁基磺醯基、十 Ιϋ戊基雜基、十三1正认雜基等經過氟原子全部取 代之予鏈狀或*支鏈狀碳原子數丨〜6之絲雜基。 烧a箄!ϊϊΐί基i例如,曱基魏基、三甲基魏基、乙基石夕 尋二矽原子之直鏈狀或分支鏈狀烷基。 或多示之!合物,有時在其構造式中包含1個 構式中,存在來自於碳—碳雙鍵之2插a f;構物,通式(1)或通式(5)表示之化合物,包含所 物及將此如任意_包含之混合物。W所有各種幾何異構 子或式(5)表示之化合物,較佳為,例如具以下所示原 盾工1门义2入3、八4車父佳為,Al為碳原子、氮;f子-〜 A2、A3、、全為碳原子=子或”化之氮 為碳原子。 局Al、A2、A3、A4全 為氫原子、C1—C4燒基,更佳為氯爱工、 G、G2 ί氯原子、C1 — C4烧基,更佳為氫原子、甲Ϊ、乙基。Cl C3 base stone slab base", such as 'silk base yellow base, ethyl rhein base, n-propyl decyl group, isopropyl sulfonyl group, cyclopropyl stellite base, etc. An alkylsulfonyl group having 1 to 3 carbon atoms, a "C1 - C6 alkylsulfonyl group", and an "α-C3 alkyl sulphate base", for example, n-butyl stellite base, tert-butyl stone An alkylsulfonyl group having a linear or branched chain carbon number such as a meso-pentylsulfonyl group or a n-hexylsulfonyl group. ~ 33 200836629 #且二基续醯基" For example, trifluoromethyl-carbyl, pentafluoroacetic acid, fluorene-difluoroethylsulfonyl, heptafluoro-n-propylsulfonate, heptafluoroisopropyl Base group, U, 2,2-tetrafluoroethyl yl group, 〗 6 = sulphide group with a chain number of 1 to 3, "C1_C6 bismuth aryl ruthenium dihalo sulfonyl sulfonyl group In addition, there are, for example, nonafluoro-n-butyl sulfonate, 9,2-dibutyllithium, 4,4,4-trifluoro-n-butylstone, all-dipentylhetero, perfluoro-n-hexane Is the sulfonyl group and so on? A chain or branched chain of carbon atoms having a number of 1 to 6 is a fluorenyl group. From + aryl%, fe oxy" for example, phenylsulfonyloxy, p-toluene xanthine ~ cai, sulphur, oxygen, 2-naphthyloxy, fluorenyloxy, phenanthryloxy - Wind, base, surface oxygen, etc. The number of carbon atoms in the ring of 6~14 is the same. "C1 - C4 alkylamino group", for example, a mercaptoamine group, an ethylamino group, a n-propylamine group, a cyclopropylamino group, or the like, a linear or branched chain i-ring atom Alkylamino group of 1 to 4, "di-C1-C4 alkylamino group", for example, dimethylamino, diethyl silk, N-ethyl-N-methylamino group, etc. Alkyl group substituted with a chain or branched chain of 1 to 4 carbon atoms. "C1-C4 perfluoroalkyl group", for example, trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl I heptafluoroindole isopropyl, nonafluoro-n-butyl, nonafluoro-2-butyl, a linear or branched chain carbon precursor which is completely substituted by a fluorine atom such as nonafluoro-isobutyl group, "~C6 all-neutral", for example, pentafluoroethyl, sulphate, hexafluoro-n-butyl a linear or branched bond carbon number of 2,6, which is substituted by a fluorine atom, such as a hexafluoro-2-butyl group, a nonafluoro-isobutyl group, an undecafluoro-n-pentyl group, or a trifluoro-n-hexyl group. Burning base. ^ C1 — C6 perfluorosulfuryl group”, for example, trifluoromethylthio, pentafluoroethylthio, sulphate, heptafluoro-isopropylthio, nonafluoro-n-butylthio, nonafluoro a linear or branched chain carbon atom 全部~6 which is completely substituted by a fluorine atom, such as 2-butyryl hexafluoro-isobutylthio group, undecafluoro-n-pentylthio group, and tridecafluoro-n-hexylthio group. Alkylthio group. 34 200836629 ^ "C1-C6 perfluoroalkylsulfinyl", for example, trifluoromethanesulfinyl, pentafluoroethyl, sulfonyl, heptafluoro-n-propylsulfinyl, heptafluoro- Isopropyl sulfinyl, hexa-di-n-butylsulfinyl, nonafluoro-2-butylsulfinyl, nonafluoro-isobutyl-based, eleven-fluoro-n-pentyl A linear or branched chain carbon atom having a total number of 丨~6 alkyl groups, such as a fluorenyl group, a trifluoro-n-hexyl hydride group, or the like. Perfluoroalkylsulfonyl", for example, trifluoromethylsulfonyl, pentafluoroethanesulfonate heptafluoro-n-propylsulfonyl, heptafluoro-isopropylsulfonyl, nonafluoro-yl-based a non-chain-like or *branched group which is completely substituted by a fluorine atom, such as a nonafluoro-2-t-t-yl-heteroyl group, a nonafluoro-isobutylsulfonyl group, a decaenylpentylheteroyl group, or a thirteen-l-n-negative hetero group. A carbon-based 丨~6 filament hetero group. Burn a! For example, a mercapto-Wiki group, a trimethyl-Wilyl group, or an alkyl group is a linear or branched chain alkyl group. Or more, the compound sometimes has one configuration in its structural formula, and there are two insertions of af from the carbon-carbon double bond; the structure, the general formula (1) or the general formula (5) A compound comprising the substance and a mixture of such as any. All of the various geometric isomers or compounds represented by the formula (5) are preferably, for example, the following: the original shield 1 1 meaning 2 into 3, 8 4 car father Jia, Al is carbon atom, nitrogen; Sub-~ A2, A3, all carbon atoms = sub- or "formed nitrogen" are carbon atoms. Al, A2, A3, A4 are all hydrogen atoms, C1-C4 alkyl, more preferably chlorine, G , G2 ί chlorine atom, C1 - C4 alkyl group, more preferably hydrogen atom, formamidine, ethyl group.
X 佳為均為氧原子。η較佳為。、1 A :基、乙基。 較佺為氧原子、鹵素 2更佳為〇或1 ⑽原于更L為虱原子或氣原子。 35 200836629X is preferably an oxygen atom. η is preferably. , 1 A : base, ethyl. More preferably, it is an oxygen atom, and halogen 2 is preferably ruthenium or 1 (10). The original L is a ruthenium atom or a gas atom. 35 200836629
Qi較佳為苯基,或 取代苯基:具擇自於鹵素原子、Cl —C4烷基、Cl —C4鹵烷 基、C2 —C4烯基、C2 —C4鹵烯基、C2 — C4炔基、C2 —C4鹵炔 基、C3—€6環烧基、C3 — C6 i|環统基、Cl—C3烧氧基、ci一 C3鹵烧氧基、Cl—C3烧石荒基、ci一C3鹵烧石荒基、Cl —C3烧基 亞磺醯基、C1—C3鹵烷基亞磺醯基、C1 — C3烷基磺醯基、cl — C3鹵烷基磺醯基、Cl —C4烷胺基、二Cl—C4烷胺基、氰基、瑞 基、羥基、Cl —C4烷羰基、Cl —C4烷羰氧基、47C1 —C4烷氧羰 基、乙醯基胺基中1個以上可相同或不同之取代基,Qi is preferably a phenyl group or a substituted phenyl group: optionally selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group. , C 2 —C 4 haloalkynyl, C 3 —€ 6 cycloalkyl, C 3 —C 6 i|cycloalkyl, Cl—C 3 alkoxy, ci—C 3 halo alkoxy, Cl—C 3 calcined base, ci—C 3 halo Calcined base, Cl-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, cl-C3 haloalkylsulfonyl, Cl-C4 alkylamine, One or more of diCl—C 4 alkylamino group, cyano group, ruthyl group, hydroxyl group, Cl—C 4 alkylcarbonyl group, Cl—C 4 alkylcarbonyloxy group, 47C1-C4 alkoxycarbonyl group, and ethyl hydrazino group may be the same or different. Substituent,
口比咬基,或 取代σ比唆基:具擇自於_素原子、C1 — C4烧基、Cl —C4鹵烧 基、C2 —C4烯基、C2 —C4鹵烯基、C2—C4炔基、C2 —C4鹵炔 基、C3 —C6環烷基、C3 — C6鹵環烷基、Cl —C3烷氧基、ci — C3鹵烷氧基、Cl —C3烷硫基、ci 一C3 i烷硫基、C1 — C3烷基 亞磺醯基、C1-C3鹵烷基亞磺醯基、C1—C3烷基磺醯基、〇一 C3鹵烧基磺醯基、Cl —C4烷胺基、二Cl —C4烷胺基、氰基、石肖 基、經基、C1 一C4烧羰基、C1 —C4烷羰氧基、α _C4烷氧^基、‘ 乙醯基胺基中1個以上可相同或不同之取代基。Orbital base, or substituted σ than thiol: selected from _ atom, C1 - C4 alkyl, Cl - C4 halogen, C2 - C4 alkenyl, C2 - C4 halo, C2 - C4 alkyne , C 2 -C 4 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, Cl -C 3 alkoxy, ci - C 3 haloalkoxy, Cl -C 3 alkylthio, ci -C3 i Alkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, fluorene-C3 halosulfonyl, Cl-C4 alkylamino , diCl—C 4 alkylamino group, cyano group, schlossyl group, thiol group, C1—C4 alkylene group, C1-C4 alkoxycarbonyl group, α—C 4 alkoxy group, and one or more of 'ethoxylated amino group. Or different substituents.
Qi更佳為苯基, —取代苯基^擇自於氟原子、氯原子、溴原子、破原子、甲基、 =氟曱基、曱氧基、三氟曱氧基、曱硫基、甲基亞磺醯基、甲基 f氟甲f基、f氟曱基亞石黃醯基、三氟甲基石黃醯基、甲 土 -甲基基、氰基、墙基中W個可相同或不同之取代 美取擇ΐ域原子、氯原子、溴原子、_子、 基、二亂甲基、甲氧基、三a甲氧基 曱基石#醯基、二t甲;w # I 丞f基亞石戸、酉皿基 脸其-氣基亞石黃、三氟甲基磺_ 甲基祕、一甲基胺基、氰基、石肖基中Μ個可相同或不同之 36 200836629Qi is more preferably a phenyl group, and a substituted phenyl group is selected from a fluorine atom, a chlorine atom, a bromine atom, a broken atom, a methyl group, a fluorenyl group, a decyloxy group, a trifluoromethoxy group, a thiol group, and a W sulfonyl, methyl f fluoromethyl f, f fluorinyl sulfastyl, trifluoromethyl fluorenyl, methane-methyl, cyano, wall, W, may be the same or different substitution取 ΐ 原子 原子 原子 氯 氯 氯 氯 氯 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子 原子, 酉 基 脸 其 - - - - - - - - - 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008 2008
啶基,其中,於通式(2)之情形, (i) Yi、A較佳為,可相同或不同,表示氟原子 碘原子、曱基、乙基、正丙基、異丙基、正丁 曱基、曱硫基、甲基亞石黃酿基、曱基石黃酿基、 曱基亞石黃醯基、三氟甲基石黃醯基、氰基; 、氣原子、溴原子、 I、2—丁基、三氟 ^氣曱硫基、^氯i Y2、Y4較佳為氫原子; Ο’/3,,為二^曱基、五氟硫烧基、U,2,3,3,3-六氟丙氧基、 2,2,2—二氟一;!一三氟甲基乙氧基、2一三氟甲氧基—一三 士,基、1,1」2二2-四氟乙氧基、i,i,2,3,3,3 —六氣丙硫基、2,2,2一 ^氟—1 一三氟甲基乙硫基、2 —三氟甲氧基一 1,1,2 —三氟乙硫 土、一1,1,2,2—四氟乙硫基、1,1,2,3,3,3 —六氟丙基亞磺醯基、2,2, 2一三氟一1 一三氟甲基乙基亞磺醯基、2—三氟甲氧基—u,2一三 氟乙基亞石頁gf基、1,1,2,2—四氟乙基亞磺酿基、i,i,2,3,3,3—六氟 丙基磺醯基、2,2,2 —三氟一 1 一三氟甲基乙基磺醯基、2一三氟甲 氧基一1,1,2-三氟乙基磺釀基、U,2,2—四氟乙基磺醯基,一或是 ⑼1較佳為,羥基曱基、曱氧基曱基、甲硫基甲基、曱基亞磺 酿基甲,、甲基磺醯基甲基、乙醯基、三氟乙醯基、乙醯氧基、 羰氧基、三氟乙醯氧基、甲氧羰基、乙氧羰基、乙醯基胺基、 ^氟乙醯基胺基、甲基石黃醯氧基、三氟甲基磺醯氧基、較佳為 氟原子、氯原子、溴原子、碘原子、曱基、乙基、正丙基、異丙 正丁苎二2~丁基、三氟甲基、甲硫基、甲基亞石黃醯基、甲基 磺醯基、三氟甲硫基、三氟甲基亞磺醯基、三氟甲基綠醯基、氰 基, 、 Υ2、Υ4較佳為氫原子; Υ3較佳為五氟乙基、七氟一正丙基、七氟一異丙基、九氟一 正丁基:九氟〜2—丁基、九氟一異丁基、三氟甲硫基、五氟乙硫 基、七氣一正丙硫基、七氟一異丙硫基、九氟一正丁硫基、九氟 37 200836629 -2-丁硫基、二氟甲基亞磺酿基、五氟乙基亞磺醯基、七氣一正 丙,亞基、七氣-異丙基亞石黃酿基、九氟一正丁基亞石黃醯基、 ,氟-2-丁基歸醯基、三氟甲基續酿基、五氟乙基》練基、七 氟-正丙基磺醯基、七氟—異丙基磺醯基、九氟一正丁基谱醯 九氟-2-丁基雜基、三氟曱基、u,2,3,3,3_六氣丙氧基ϋ -三氣-1-三氟甲基乙氧基、2_三氟甲氧基—u,2—三乙气 基、U,2,2-四氟乙氧基、U,2,3,3,3 —六氣丙硫基、2,22—三= -1-三氟I基乙硫基、2-三氟甲氧基一 u,2 —三氟乙疏基、 1」1二2,2—四,^硫基、1,1,2,3,3,3 —六氟丙基亞磺醯基、2,2,2 — 二氟一 1 一二氟甲基乙基亞石黃醯基、2一三氟甲氧基一2一二友 乙基亞磺驢基、1,1,2,2-四氟乙基亞續酿基、u,2,3,3^_ = 基雜基、2,2,2-三氟-i-三就甲基乙基石黃酿基、〔三/說 基一 1山2 —二氟乙基磺醯基、m2—四氟乙基磺醯基, 年 為氧气、五氟乙基、三氟甲硫基、五氟乙ΐ基、 鼠丙瓜基七氟異丙硫基、二氟甲基亞績醯基、五 醯基、七就丙基亞石黃酿基、七氣異丙基亞石黃醯基、三 1 = 基、jit石黃酿基、七氣丙基石黃酿基、七氟異丙基磺酸, 一友Y5j父佳為氟原子、氣原子、溴原子、碘原子、曱基、乙 二^曱氧基、五氟乙基、三氟曱硫基、五氟乙硫基、 1、a pyridine group, wherein, in the case of the formula (2), (i) Yi, A are preferably the same or different, and represent a fluorine atom iodine atom, a thiol group, an ethyl group, a n-propyl group, an isopropyl group, and a positive group. Butyl sulfhydryl, sulfonium thiol, methyl sulphate, sulphur base, fluorenyl fluorenyl, trifluoromethyl sulphate, cyano; gas atom, bromine atom, I, 2-butyl, Trifluoromethane thiol, chloro i Y2, Y4 are preferably a hydrogen atom; Ο'/3, is a dithiol group, a pentafluorosulfuryl group, U, 2,3,3,3-hexafluoro Propyloxy, 2,2,2-difluoro-;!-trifluoromethylethoxy, 2trifluoromethoxy-tris, 1,1,2,2-difluoroethoxy Base, i, i, 2, 3, 3, 3 - hexapropylpropylthio, 2,2,2-fluoro-l-trifluoromethylethylthio, 2-trifluoromethoxy-1,1 , 2 - trifluoroethyl sulfide, 1,1,2,2-tetrafluoroethylthio, 1,1,2,3,3,3-hexafluoropropylsulfinyl, 2,2, 2 Trifluoro-1,3-trifluoromethylethylsulfinyl, 2-trifluoromethoxy-u, 2-trifluoroethyl sulfite gf, 1,1,2,2-tetrafluoro Keasulfonic acid, i, i, 2, 3, 3, 3 - hexafluoropropyl Sulfonyl, 2,2,2-trifluoro-l-trifluoromethylethylsulfonyl, 2trifluoromethoxy-1,1,2-trifluoroethylsulfonyl, U,2 , 2-tetrafluoroethylsulfonyl, one or (9) 1 is preferably, hydroxyindenyl, decyloxymethyl, methylthiomethyl, decylsulfinyl, methylsulfonyl , ethyl fluorenyl, trifluoroethyl fluorenyl, ethoxycarbonyl, carbonyloxy, trifluoroacetoxy, methoxycarbonyl, ethoxycarbonyl, ethionylamino, fluoroethenylamine, Methyl ferrocyanoxy, trifluoromethylsulfonyloxy, preferably fluorine atom, chlorine atom, bromine atom, iodine atom, sulfhydryl group, ethyl group, n-propyl group, isopropyl n-butyl hydrazine 2~ Butyl, trifluoromethyl, methylthio, methyl sulfite, methylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylphosphonium, cyano, Υ2, Υ4 is preferably a hydrogen atom; Υ3 is preferably pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluoro-n-butyl: nonafluoro-2-butyl, nonafluoro Isobutyl, trifluoromethylthio, pentafluoroethylthio, heptaqi-n-propylthio, heptafluoro-isopropyl Base, nonafluoro-n-butylthio, nonafluoro37 200836629 2-butylthio, difluoromethylsulfinyl, pentafluoroethylsulfinyl, seven gas, one, one, seven -Isopropyl sulphate, nonafluoro-n-butyl sulphate, fluoro-2-butylindole, trifluoromethyl aryl, pentafluoroethyl, hexafluoro- N-propylsulfonyl, heptafluoro-isopropylsulfonyl, nonafluoro-n-butyl spectrum, nonafluoro-2-butylhetero, trifluoromethyl, u, 2, 3, 3, 3_ Hexapropoxy fluorene-tris-l-trifluoromethylethoxy, 2-trifluoromethoxy-u, 2-triethoxy, U, 2,2-tetrafluoroethoxy, U , 2,3,3,3—hexapropanylthio, 2,22—tris=-1-trifluoromethylsulfanyl, 2-trifluoromethoxy-u,2-trifluoroethylidene, 1"1 2 2,2 - 4,^thio, 1,1,2,3,3,3-hexafluoropropylsulfinyl, 2,2,2-difluoro-1,4-difluoromethyl Ethyl sulphate, 2,3-trifluoromethoxy-2,2-diethyl sulfinyl, 1,1,2,2-tetrafluoroethyl sulphate, u, 2, 3, 3^ _ = base hetero group, 2,2,2-trifluoro-i-three on methyl ethyl stellite base, [three / say base one 1 mountain 2 - Difluoroethylsulfonyl, m2-tetrafluoroethylsulfonyl, annual oxygen, pentafluoroethyl, trifluoromethylthio, pentafluoroacetamido, murine citrate, heptafluoroisopropylthio , difluoromethyl sulfhydryl, quinone, hexamethyl sulfite, seven gas isopropyl sulfite, sulphate, sulphate, sulphate, sulphate Base, heptafluoroisopropylsulfonic acid, a friend Y5j parent is a fluorine atom, a gas atom, a bromine atom, an iodine atom, a sulfhydryl group, an ethanediyloxy group, a pentafluoroethyl group, a trifluorosulfonylthio group, a Fluoroethylthio group, 1,
巧異丙硫基、三I甲基亞顧基、五氣乙基亞贿美、七W ΐϊΐ醯基、七氟異丙基亞磺、三氟甲基磺醯基、五氟I臭 石只鲶基、七氟丙基磺醯基、七氟異丙基磺醯基; 土 Y2、Y4較佳為氫原子; ’ Υ3為氟原子、氣原子、溴原子、破原子· 於通式(4)之情形, ’ 挑原m交佳S可相同ί不同,為a原子、氯原子、漠原子、 ,、二 曱基、乙基、正丙基、異丙基、正丁基、2一丁其、一友 曱基、曱硫基、甲基亞績酿基、甲基礦、 甲基亞確醯基、三氟曱基雜基、氰基;4曱硫基、二氟 38 200836629 Y2、I較佳為氫原子; 氟美基、Rb為氣原子、Rc為三氟甲基,或Ra為氯二 亂基、Rb為經基、Rc為氯二氣甲基較佳。 此箄⑴Ϊ不之化合物,例如以下化合物1〜舊1之化合物。 絲之觀鱗看,為較佳可使用者。 化合物I,係通式(1)中, fi表不奴原子、氮原子或經氧化之氮原子· Α2、Α3、Α4表示碳原子; ,Isopropylthio, tri-Imethyl-Agaki, five-gas ethyl-branth, seven-W-decyl, heptafluoroisopropylsulfinyl, trifluoromethylsulfonyl, pentafluoro I streak Sulfhydryl, heptafluoropropylsulfonyl, heptafluoroisopropylsulfonyl; soils Y2, Y4 are preferably hydrogen atoms; 'Υ3 is a fluorine atom, a gas atom, a bromine atom, a broken atom · in the formula (4) In the case of ', pick the original m, the best S can be the same, is a atom, chlorine atom, desert atom, ,, di-mercapto, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl It is a friend, a sulfhydryl group, a thiol group, a methyl sulfonyl group, a methyl ore, a methyl sulfenyl group, a trifluoromethyl group, a cyano group; a 4 thiol group, a difluoro group 38 200836629 Y2 I is preferably a hydrogen atom; a fluoromethym, Rb is a gas atom, Rc is a trifluoromethyl group, or Ra is a chloroform group, Rb is a mesogenic group, and Rc is a chlorodimethyl group. The compound of the above (1) is not a compound, for example, the following compound 1 to the compound of the old one. It is better to be user-friendly. Compound I, in the formula (1), fi represents a slave atom, a nitrogen atom or an oxidized nitrogen atom, Α2, Α3, Α4 represents a carbon atom;
Rl、R2彼此獨立表示氫原子或Cl —C4烷基·Rl and R2 independently of each other represent a hydrogen atom or a Cl—C4 alkyl group.
Gi、〇2彼此獨立表示氧原子或硫原子;, 乂^為相同或不同,表示氫原子素 η表示0至4之整數; ^Gi and 〇2 independently represent an oxygen atom or a sulfur atom; and 乂^ is the same or different, and represents a hydrogen atom η representing an integer from 0 to 4;
Qi表不未基, 取代苯基··具擇自於鹵素原子、ci — 經,之a-C4烧基、C2— 二 -C3烧氧基、C1—C3齒烧Hf·、齒環烧基、α 硫基、a-C3烧基亞麵硫基、ci—C3姐 p装译妒I n A :、 C1〜C3鹵烷基亞磺醯基、Cl —C3 絲石*基、C1-C3 _烧基石黃酸基 烧胺基、氰基、石肖基、·、C1 m 4ci—C4 n] 一na ϋ Α γμ〜上 元参厌基Cl C4鹵烧爹厌基、Qi is not unsubstituted, substituted phenyl··from halogen atom, ci—, a-C4 alkyl group, C2-di-C3 alkoxy group, C1-C3 tooth-burning Hf·, tooth ring , α thio, a-C3 alkyl sulfenyl, ci—C3 p 妒 n I n A :, C1~C3 haloalkyl sulfinyl, Cl—C3 stellite*, C1-C3 _ burnt fluorescens-based amphotery group, cyano group, succinyl group, · C1 m 4ci-C4 n] a na ϋ Α γμ ~ 上元 厌 Cl Cl Cl C4 halogen 爹 爹 base,
Cl C4说祕基、C1 —C4鹵垸幾氧基 卢 一C4鹵烷氧羰基、C1〜C4烷幾 匕4烷虱叛基C1 一至妒β甘 私基、C1 —C4鹵烷羰胺基、C1 -C4烷基砀酗虱基、a_C4南燒基‘醯 氟硫烧^或苯基中可相同或不同之巧個以上^代* H 土、 f環基(在此之雜環基表示Μ基、nfct基^ 基、嗟峻基、異嗟^ 、,唾基、喝二嗤 吼嗤基、四錢、2,3t 44t 1基、料基、三嗤基、 一二本开f1,4]二噚啡基、苯并[1,3]二嘮 39 200836629 σ坐基、四氫派喃基或二氫u底喃基。) 或, 取代雜環基:具擇自於自素料、C1—a絲、C1—〇4姐 基、經取代之Cl —C4燒基、—C4烯基、C2 —C4鹵烯基、C2 • —C4炔基、C2 —C4函炔基、C3 — C8環烷基、C3-C8幽環烷基、 • C1 一C3烷氧基、C1 一C3鹵烷氧基、C1-C3烷硫基、C1_C3鹵 烷硫基、C1 一 C3烷基亞磺醯基、C1—C3 _烷基亞磺醯基、C1 — C3烧基石頁基、C1 — C3幽烧基石黃|藍基、ci —C4烧胺基、二Cl 一C4烷胺基、氰基、硝基、羥基、C1_C4烷羰基、C1_C4鹵烷 ⑩ 羰基、C1 —C4烧羰氧基、C1 — C4鹵烧羰氧基、C1 — C4烧氧羰基、 C1 一C4鹵烷氧羰基、C1 一C4烷羰胺基、C1—C4鹵烷羰胺基、 C1—C4烧基石頁醯氧基、C1 一C4 _烧基石黃醢氧基、芳石黃醯氧基、 五氟硫烷基或苯基中可相同或不同之1個以上取代基(在此之雜環 基表示吡喷基、吡啶基、N—氧化吡啶基、嘧啶基、嗒畊基、呋喃 基、脅吩基、噚峻基、異噚唑基、噚二唑基、嗟嗤基、異嗔嗤基、 噻二唑基、u比嘻基、咪唑基、三唑基、^比唑基、四唑基、2,3 一二 氮本并[I,4]一今井基、苯并[1,3]二喝嗤基、四氫旅味基或二氫派 σ南基。 Q2為通式(2)Cl C4 is said to be a secret group, a C1-C4 halogenated oxime oxime-C4 haloalkoxycarbonyl group, a C1~C4 alkane group, a decyl group, a C1 group to a 妒β-glycol group, a C1-C4 haloalkylcarbonyl group, The C1 -C4 alkyl fluorenyl group, the a_C4 succinyl group, the fluorinated sulphur sulphur or the phenyl group may be the same or different, and the hexyl group is the same as the H ring, and the ring group (wherein the heterocyclic group represents Μ) Base, nfct base ^ base, 嗟 基 base, iso 嗟 ^,, sulphate, diterpene, tetraki, 2, 3t 44t 1 base, material base, triterpene, one or two open f1, 4 Di- morphinyl, benzo[1,3]dioxene 39 200836629 σ, 1, tetrahydropyranyl or dihydro-u- yl.) or, substituted heterocyclyl: selected from its own C1-a silk, C1-—4 sister group, substituted Cl—C4 alkyl group, —C4 alkenyl group, C2-C4 haloalkenyl group, C2•—C4 alkynyl group, C2-C4 alkynyl group, C3—C8 Cycloalkyl, C3-C8 sec-cycloalkyl, • C1 - C3 alkoxy, C1 - C3 haloalkoxy, C1-C3 alkylthio, C1_C3 haloalkylthio, C1 - C3 alkyl sulfinyl , C1-C3 _alkyl sulfinylene, C1 - C3 sulphur base, C1 - C3 sulphur base yellow | blue base, ci - C4 amine group, two C l C4 alkylamino, cyano, nitro, hydroxy, C1_C4 alkylcarbonyl, C1_C4 haloalkyl 10 carbonyl, C1-C4 carbonyloxy, C1-C4 carbonyl carbonyl, C1-C4 oxycarbonyl, C1 a C4 haloalkoxycarbonyl group, a C1 to C4 alkylcarbonylamino group, a C1-C4 haloalkylcarbonylamino group, a C1-C4 alkyl fluorenyloxy group, a C1-C4-calcinyl fluorenyloxy group, a fluorite xanthine oxygen One or more substituents which may be the same or different in the group, pentafluorosulfanyl group or phenyl group (herein, heterocyclic group means pyridyl group, pyridyl group, N-oxidized pyridyl group, pyrimidinyl group, hydrazine group, furan group) Base, thiophene, thiophene, isoxazolyl, oxadiazolyl, fluorenyl, isodecyl, thiadiazolyl, u-indenyl, imidazolyl, triazolyl, thiazolyl , tetrazolyl, 2,3, dinitrogen, [I, 4], a well, benzo[1,3], diterpene, tetrahydron, or dihydrogen, sigma. Formula (2)
(式中,γι、Υ5可為相同或不同,表示鹵素原子、C1—C6烷 土 Cl C6鹵燒基、ci — C6嫁氧基、C1 —'C6鹵烧氧基、C1 一 =燒硫基C1~C6 _烧硫基、C1 — C6烷基亞續酿基、C1 — C6 鹵烷基亞磺醯基、C1 — C6烷基石黃醯基、C1 — C6鹵烷基石黃醯基、 氰基或硝基; I、Y4可為相同或不同,表示氫原子、鹵素原子或C1—C6 200836629 Y3表不三氣甲某、pi r^r: . ^ 取代鼠,基、五氣硫,’ 原子、蛾原子、Cl-C6烧rf氣原子、搜基、氯原子、溴 同之1個以上取代基所取代丨或C1〜C6姐氧基中可相同或不 原子、自於氫原子、羥基、氯原子、溴 同之1個以上取代基所取=,土 4 C1—C6姐氧基中可相同或不 子、itr、烧,自於氫原子、經基、氯原 ,或不同之!個以上取代基所^基或ci—c6函烧氧基中可相 或’ 不同之1個以上取代基所取H或C1—C6姐氧基巾可相同或 (化合物II) 化合物Π,係通式(1)中, ^表不碳原子、氮原子或經氧化之氮原七 2 A3、Α4表不碳原子; 、R2彼此獨立表示氫原子或C1_C4烷基; 1、>彼此獨立表示氧原子或硫原子; I為相同或不同,表示氫原子、鹵素原子或三氟曱基· η表示〇至4之整數; ,(wherein, γι and Υ5 may be the same or different, and represent a halogen atom, a C1-C6 alkane Cl C6 halogen group, a ci-C6 graft oxy group, a C1 - 'C6 halogen alkoxy group, a C1 group = a sulfur-burning group C1~C6 _ sulphur-burning group, C1-C6 alkyl sulfonyl, C1 - C6 haloalkyl sulfinyl, C1 - C6 alkyl fluorenyl, C1 - C6 haloalkyl fluorenyl, cyano or nitro; I, Y4 may be the same or different, and represent a hydrogen atom, a halogen atom or a C1-C6 200836629 Y3, which is not a gas, a pi r^r: . ^ a substituted mouse, a base, a five-gas sulfur, an atom, a moth atom, Cl-C6 calcined rf gas atom, thiol, chlorine atom, bromine substituted with more than one substituent 丨 or C1~C6 sister oxy group may be the same or non-atom, from hydrogen atom, hydroxyl group, chlorine atom, bromine With the same substituent taken by one or more substituents, the 4 C1-C6 oxy group of the soil may be the same or not, itr, or burned, from a hydrogen atom, a thiol group, a chloroform, or a different substituent. ^ or ci-c6 function in the alkoxy group may be phase or 'different one or more substituents taken H or C1-C6 sister's oxygen towel may be the same or (compound II) compound Π, in the formula (1) , ^ The carbon atom, the nitrogen atom or the oxidized nitrogen atom seven 2 A3, Α4 represents a carbon atom; and R2 independently of each other represents a hydrogen atom or a C1_C4 alkyl group; 1. > independently of each other represents an oxygen atom or a sulfur atom; The same or different, meaning that a hydrogen atom, a halogen atom or a trifluoromethyl group η represents an integer of 〇 to 4;
Qi表示苯基, 取代笨基:具擇自鹵素原子、C1—C4烷基、C1—C4 鹵烷基 ^美 r?Cl —C4 烷基、C2—C4 烯基、C2—C4 鹵稀基、C2—C4 二忘j:C4鹵炔基、C3 —C8環烷基、C3-C8自環烷基、Cl 琉基、氧基、C1—C3烧硫基、C1~C3鹵烧 烫其石至妒3烷土亞IS醯基、C1_C3鹵烧基亞石黃醯基、C1 一 C3 凡土只基、Cl —56C3鹵烷基磺醯基、C1 —C4烷胺基、二cl_ 41 200836629 C4烧胺基、氣基、硝基、經基、Cl — C4院幾基、ci — C4鹵烧幾 基、Cl —C4烧叛氧基、ci~C4鹵烧幾氧基、Cl —C4烧氧獄基、 Cl—C4鹵烷氧羰基、C1-C4烷羰胺基、C1-C4鹵烧幾胺基、 Cl—C4烧基磺醯氧基、ci一C4鹵烧基石黃醢氧基、芳石黃醯氧基、 五氟硫烷基或苯基申可相同或不同之1個以上取代基, 雜環基(在此之雜環基表示吡嗜基、吡啶基、氧化吡咬基、 嘧啶基、嗒啡基、呋喃基、噻吩基、噚唑基、異噚唑基、噚二哇 基、噻唑基、異噻唑基、噻二唑基、吡咯基、咪唑基、三唑基、 吡唑基、四唑基、2,3 —二氲一苯并[1,4]二噚啡基、苯并夸 唑基、四氫哌喃基或二氫哌喃基。), ’ 或 取代雜壞春具擇自於自素原子……㈣、“—Μ國現 基、餐取代之C1-C4烷基、C2—C4烯基、C2 —C4自稀基、C2 基=—C4幽块基、C3 一⑶魏基、C3 — C8鹵環烧基、 =烧乳基、Cl—C3 -烧氧基、C1_C3烧硫基、C1—〇鹵 二f、Cl —C3烷基亞磺醯基、α —C3鹵烷基亞磺醯基、α — 、a—57C3祕基磺醯基、Cl—c4驗基、二 内、烷ί基二鼠基、硝基、羥基、C1—C4烧羰基、C1—C4 二?羰氧基、cl-C4鹵烷羰氧基、C1-C4烷氧 美t C1 — Γ4基、C1 一 C4燒幾胺基、C1 — C4鹵烧羰胺 i、五隨基、C1—C4自絲續醢氧基、芳磺酸氧 i基表it,或仰之1個以上取代基(在此之雜 喃基、嗟吩基、今唾笑基:氧,比咬基、•定基、塔絲、吱 基、嗟二唆基、对i 4=基、錄、勉基、異嗟嗤 二氫i南Γΐ,基、苯并[切二啊基、四氫旅喃基或 Q2為通式(2) 42 (2) 2 1 200836629Qi represents a phenyl group, a substituted phenyl group: optionally selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a r?Cl-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 halogen group, C2—C4 二忘 j: C4 haloalkynyl, C3-C8 cycloalkyl, C3-C8 self-cycloalkyl, Cl decyl, oxy, C1-C3 sulphur-based, C1~C3 halogen-burning stone to妒3 alkaloids Y sulfhydryl, C1_C3 halogenated carbazite, C1 - C3, sulphate, Cl - 56C3 haloalkyl sulfonyl, C1 - C4 alkylamino, di cl_ 41 200836629 C4 amine , gas base, nitro, thiol, Cl - C4, several groups, ci - C4 halogen group, Cl - C4 burnt alkoxy, ci ~ C4 halogen burned oxy, Cl - C4 burned oxygen base, Cl-C4 haloalkoxycarbonyl, C1-C4 alkylcarbonylamine, C1-C4 halogenated amino group, Cl-C4 alkylsulfonyloxy, ci-C4 halogenated fluorenylxanthine, arsenite xanthine An oxy group, a pentafluorosulfanyl group or a phenyl group may have the same or different one or more substituents, and a heterocyclic group (herein a heterocyclic group means a pyridyl group, a pyridyl group, an oxypyridyl group, a pyrimidyl group, an anthracene group). Pentyl, furyl, thienyl, oxazolyl, isoxazolyl, anthracenyl, thiazolyl, Thiazolyl, thiadiazolyl, pyrrolyl, imidazolyl, triazolyl, pyrazolyl, tetrazolyl, 2,3-diphenylbenzo[1,4]dioxinyl, benzoquinazolyl , tetrahydropyranyl or dihydropyranyl.), ' or substituted miscellaneous springs are selected from the self-atomic atom... (4), "----------------- C1-C4 alkyl, C2- C4 alkenyl, C2-C4 from dilute base, C2 base = -C4 cleavage group, C3-(3) wei group, C3 - C8 halocycloalkyl group, = calcined base, Cl-C3 - alkoxy group, C1_C3 sulfur-burning Base, C1 - hydrazine, dif, Cl - C3 alkyl sulfinyl, α - C3 haloalkyl sulfinyl, α - , a - 57C3, sulfonyl, Cl - c4, base , alkyl 2, nitro, hydroxy, C1-C4 carbonyl, C1-C4 biscarbonyloxy, cl-C4 halocarbonyloxy, C1-C4 alkoxy t C1 - Γ4, C1 a C4-burning amine group, a C1-C4 halogen-burning carbonylamine i, a penta-propanyl group, a C1-C4 self-spinning oxo group, an arylsulfonyloxy group i-based table, or a substituent of more than one (here) Heterogeneous group, porphinyl group, present smirk base: oxygen, bite base, • base, tas, thiol, fluorenyl, i 4 = base Recording, Mian group, iso-dihydro sigh laugh i South Γΐ, group, benzo [ah two cut-yl, tetrahydro-thiopyran trip or Q2 is a group of the general formula (2) 42 (2) 21200836629
(式中,Υι表示Cl —C4烷羰基、C1 — C4鹵烷羰基、C1~C4 烧幾氧基、Cl —C4齒烧幾氧基、ci 一C4烧氧幾基、Cl —C4鹵烧 氧羰基、C1 — C4烷羰胺基、C1 — C4 58齒烷羰胺基、C1—C4烷 基石黃醯氧基、C1 一C4幽烧基石黃醢氧基, 或 取代Cl—"C4烧基··經擇自於鹵素原子、ci —C3烧氧基、C1(wherein Υι denotes Cl—C4 alkylcarbonyl, C1-C4 halocarbonyl, C1~C4 caloxy, Cl—C4 chiral oxy, ci—C4 aerobic acid, Cl—C4 halogenated oxygen Carbonyl, C1 - C4 alkylcarbonylamino, C1 - C4 58 alkanocarbonylamino, C1-C4 alkyl fluorenyloxy, C1 - C4 cryptoyl fluorenyloxy, or substituted Cl-"C4 alkyl ··Selected from halogen atom, ci—C3 alkoxy, C1
—C3 i烷氧基、C1 — C3烷硫基、C1 — C3 _烷硫基、C1 — C3烷 基亞續醯基、C1 — C3 _烧基亞續醯基、ci —C3烧基磺盤基、C1 —C3鹵烧基磺醯基、C1 一C4燦胺基、二C1 — C4烧胺基、氰基、 硝基、羥基、C1 一C4烷羰基、C1 一C4鹵烷羰基、C1 一C4烷羰氧 基、C1 — C4鹵烧羰氧基、C1 — C4烷氧羰基、C1 —C4鹵烷氧羰基、 C1—C4烧幾胺基、C1 — C4 d烧幾胺基、C1 — C4烧基石黃醯氧基、 C1 — C4鹵烷基確醯氧基、芳磺醯氧基、五氟硫烷基或烷基矽烷基 中可相同或不同之1個以上取代基所取代; Y5表示鹵素原子、C1—C6烷基、C1—C6 i烧基、C1_C6 烧氧基、Cl —C6鹵烧氧基、a —C6垸硫基、α —C6函烧硫基、 C1 — C6烧基亞磺酿基、C1—C6 _烷基亞續醯基、C1 — c 醯基、Cl—C6鹵烷基磺醯基、氰基或硝基; 兀土 ’、 γ2、γ4可為相同或不同,表示氫原子、_素原子、ci_c6 院基; LZ· ϊ3表不C1-C4鹵烷氧基〜—坌氟烷基 、:?ί其C1;C6纖細_基、Cl-C6錢烷基碏醯ί —亂甲基、C1—C6全氟烷氧基、五氟硫烷基, ’、· 取代C1 — C6鹵烷氧基:經擇自於氫原子、羥 a 、 原子、換原子、C1—〇6炫氧基或a_c ,原子、〉 之1個以上取代基取代, 虱基中相同或不ί 取代Cl-C6鹵烷硫基··經擇自於氫原子、經其> 二$、氣原子、溴 43 200836629—C 3 i alkoxy, C 1 —C 3 alkylthio, C 1 —C 3 —alkylthio, C 1 —C 3 alkyl sulfhydryl, C 1 —C 3 —alkyl sulfhydryl, ci —C 3 alkyl sulfonate Base, C1-C3 halosulfonylsulfonyl, C1-C4 butylamine, di-C1-C4 acrylamine, cyano, nitro, hydroxy, C1-C4 alkylcarbonyl, C1-C4 halocarbonyl, C1 C4 alkylcarbonyloxy, C1-C4 halogenated carbonyloxy, C1-C4 alkoxycarbonyl, C1-C4 haloalkyloxycarbonyl, C1-C4 succinyl, C1-C4d succinyl, C1-C4 Substituting one or more substituents which may be the same or different in the pyridylxanthine, C1-C4 haloalkyl group, arylsulfonyloxy group, pentafluorosulfanyl group or alkylalkylene group; Y5 represents Halogen atom, C1-C6 alkyl group, C1-C6 i alkyl group, C1_C6 alkoxy group, Cl-C6 halogen alkoxy group, a-C6 thiol group, α-C6 functional thio group, C1 - C6 alkyl group Sulfonic acid, C1-C6-alkyl sulfhydryl, C1-c fluorenyl, Cl-C6 haloalkylsulfonyl, cyano or nitro; alumina ', γ2, γ4 may be the same or different, Represents hydrogen atom, _ atom, ci_c6 courtyard; LZ· ϊ3 represents C1-C4 Haloalkoxy~-fluoroalkyl,: ?? C1; C6 slastic _ group, Cl-C6 hydroxyalkyl 碏醯 - chaotic methyl, C1-C6 perfluoroalkoxy, pentafluorosulfanyl , ', · Substituted C1 - C6 haloalkoxy: substituted by one or more substituents selected from the group consisting of a hydrogen atom, a hydroxy a, an atom, a transatom, a C1-hexanoxy group or a_c, an atom, 虱The same or no substitute for the Cl-C6 haloalkylthio group is selected from a hydrogen atom, via its > two, a gas atom, bromine 43 200836629
Cl〜C6鹵烧氧基中相同或不同 原子、碘原子、Cl—C6烷氧; 之1個以上取代基取代, 取代C1 — C6鹵烷基亞磺醯基·叙 子、漠原子、碘原子、巧自於虱原子、羥基、氯原 或不同之1個以上取代基所取代,平土或C1~C6鹵烷氧基中相同 或, 取代C1—C6鹵烷基磺醯基:經擇 漠原子、礙原子、C1_C6烧氧擇,於^子、錄、氯原子、 同之1個以上取代基所取代)。a U—C6鹵烷氧基中相同或不 (化合物III) 通式⑴中, ^表村軒、子或魏化 八2、A3、A4表示碳原子; 火” ’Cl~C6 halogenated alkoxy group in the same or different atom, iodine atom, Cl-C6 alkoxy; substituted by more than one substituent, substituted C1 - C6 haloalkyl sulfinyl group, sulphur, iodine atom Substituted by a ruthenium atom, a hydroxyl group, a chlorinogen or a different substituent or more, in the plain or C1~C6 haloalkoxy group, the same or substituted C1-C6 haloalkylsulfonyl group: Atom, an intrusive atom, C1_C6 is an oxygen-selective substitution, and is replaced by a substituent, a chlorine atom, and one or more substituents. a U-C6 haloalkoxy group the same or not (compound III) In the formula (1), ^表村轩,子 or 魏化 八2, A3, A4 represents a carbon atom;
Ri、R2彼此獨立表示氫原子或ci〜c Gi、G2彼此獨立表示氧原子或硫原子·兀土,Ri and R2 independently of each other represent a hydrogen atom or ci~c Gi, and G2 independently represents an oxygen atom or a sulfur atom.
Qi表示苯基, 叫自於函素原子、C1〜C4燒基、Cl—C4鹵院基、 、、工,代之Cl—C4烷基、C2_C4烯基 炔基、C2-C4齒伊美、C3_C8产㈠ 14®减C2 C4 I ^ I L8衣烧基、C3 — C8鹵環烧基、C1 护美、ΐι "ci J:C3 ^氧基、C1—C3烷硫基、C1 -C3鹵烷 3石4^ 3基亞磺醯基、C1~C3 *絲亞績·、C1-C3 ϊί f卞:〇一。鹵烷基磺醯基、Cl,烷胺基、三C1-C4 二一ϋ::确基、經基、α 一c4烧幾基、ci—c4鹵烧幾基、 二二、氧基、C1_C4齒烧幾氧基、C1 —C4烧氧幾基、C1 —α 碳,、C1_C4烧幾胺基、C1 — C4鹵烧幾胺基、C1 龜氧基、C1 一C4齒烧基確酿氧基、芳石黃酸氧基、五 亂瓜烷基或本基中相同或不同之1個以上取代基, 44 200836629 、雜環基(在此之雜環基表示ϋ比畊基、定基、N —氧化。比咬基、 唯'啶基、嗒畊基、呋喃基、噻吩基、噚嗤基、異噚峻基、噚二唑 基、嗟峻基、異嗟唾基、嗟二嗤基、Π比略基、味嗤基、三唾基、 °比唑基、®唑基、2,3 —二氫一苯并[I,4]二十井基、苯并[切二口号 哇基、四氫旅喃基或二氫派喃基。),或 - 取代雜環基:具擇自於鹵素原子、C1 — C4烧基、Cl —C4鹵烧 基、經取代之C1-C4烷基、C2 —C4烯基、C2 —C4鹵烯基、C2 —C4炔基、C2 — C4 i炔基、C3 一C8環烷基、C3 — C8齒環烷基、 C1 一C3烧氧基、C1 — C3鹵烷氧基、C1 — C3烧硫基、C1 — C3鹵 • 烷硫基、C1 一 C3烷基亞磺醯基、C1 — C3 i烷基亞磺醯基、C1 — C3烧基石黃醯基、Cl 一C3鹵烧基石黃醯基、C1 — C4烧胺基、二01 一C4烧胺基、氰基、硝基、羥基、— 羰基、C1 — C4鹵燒 羰基、C1 — C4烷羰氧基、C1 — C4鹵烷羰氧基、C1_C4烷氧羰基、 C1 一 C4鹵烧氧魏基、C1 一C4烷羰胺基、C1 — C4 _烷羰胺基、 C1 一C4烷基磺醯氧基、C1-C4鹵烷基績醯氧基、芳磺醯氧基、 五氟硫烧基或苯基中相同或不同之1個以上取代基(在此之雜環 基表示吼畊基、吼咬基、N—氧化η比咬基、嘧^定基、塔畊基、咬 基、噻吩基、噚唑基、異噚唑基、噚二唑基、噻唑基、異噻唑基、 °奏二嗤基、吼略基、味唾基、三嗤基、吼唾基、四嗤基、2,3〜二 氫-苯并[1,4]二今井基、苯并[切工喝嗤基、四氮派喃基或 哌喃基。); ^ Q2為通式(2)Qi represents phenyl, which is called from a hydroxyl atom, a C1~C4 alkyl group, a Cl-C4 halogen compound, a work, a Cl-C4 alkyl group, a C2_C4 alkenyl alkynyl group, a C2-C4 tooth Yimei, a C3_C8 Production (1) 14® minus C2 C4 I ^ I L8, C3 — C8 halocycloalkyl, C1 护美, ΐι "ci J: C3 ^oxy, C1-C3 alkylthio, C1-C3 halo 3 stone 4^ 3 sulfinyl, C1 ~ C3 * silk Asian performance ·, C1-C3 ϊί f卞: 〇 one. Haloalkylsulfonyl, Cl, alkylamino, tri-C1-C4 di-anthracene:: exact group, trans-group, α-c4 alkyl group, ci-c4 halogen group, di-, oxy, C1_C4 Chiral oxy group, C1-C4 aerobic acid group, C1 -α carbon, C1_C4 succinylamine, C1 - C4 halogen sulphate, C1 toroxy, C1 - C4 dentate , arsenate, sulphate or the same or different one or more substituents in the group, 44 200836629, heterocyclic group (herein, heterocyclic group means argon, basal, N - Oxidation. butyl group, only pyridine group, hydrazine, furyl, thienyl, fluorenyl, isoindolyl, oxadiazolyl, anthracenyl, isoindolyl, fluorenyl, fluorene Biletyl, miso base, trisalyl, °bazolyl, oxazolyl, 2,3-dihydro-benzo[I,4]20-well, benzo[cut two slogan wah, four Hydrogen bromo or dihydropyranyl.), or - substituted heterocyclic: optionally selected from a halogen atom, a C1 - C4 alkyl group, a C-C4 halogen group, a substituted C1-C4 alkyl group, C2 —C 4 alkenyl, C 2 —C 4 haloalkenyl, C 2 —C 4 alkynyl, C 2 —C 4 i alkynyl, C 3 —C 8 cycloalkyl , C3 — C8 cyclyl, C1—C3 alkoxy, C1-C3 haloalkoxy, C1-C3 sulphur-based, C1-C3 halo-alkylthio, C1-C3 alkylsulfinyl, C1 — C3 i-alkylsulfinyl, C1—C3 alkyl ruthenium, Cl-C3 halogenated ruthenium, C1-C4 arunyl, 2-1, C4, cyano, nitro, hydroxy, — Carbonyl, C1-C4 halogenated carbonyl, C1-C4 alkoxycarbonyl, C1-C4 halocarbonyloxy, C1_C4 alkoxycarbonyl, C1-C4 halooxycarbonyl, C1-C4 alkylcarbonyl, C1 — One or more of C4-alkylcarbonylamino, C1-C4 alkylsulfonyloxy, C1-C4 haloalkyloxy, arylsulfonyloxy, pentafluorosulfoxy or phenyl Substituent (heterocyclic group here means hydrazine, biting group, N-oxidizing η than biting group, pyrimidine group, argonyl group, biting group, thienyl group, carbazolyl group, isoxazolyl group, hydrazine group Diazolyl, thiazolyl, isothiazolyl, ° dioxin, oxime, sulphonyl, tridecyl, oxime, tetradecyl, 2,3~dihydro-benzo[1,4 ]二今井基,苯苯[切工嗤嗤,四氮派基基或Piperidyl.); ^ Q2 is of formula (2)
(式中,Υι表示C1-C6烷氧基、C1 — C6鹵烷氧基、C1〜 烧硫基、Cl —C6齒烧硫基、C1-C6烧基亞磺醯基、C1_C6 6尸 基亞磺醯基、Cl —C6烷基磺醯基或C1 — C6鹵烷基磺醯基;凡 Y5表示鹵素原子、Cl —C6烷基、C1 — C6鹵烷基、C1〜C6 45 200836629 =6 姆、a-硫基、 酿基γ基==酿基、C1,絲續 烧基,2 4可為相同或不同,表示氫原子、鹵素原子、C1-C6 Y3表示鹵素原子。)。 (化合物IY) 通式(二A1=;以 》、,彼此獨立表示氫原子或C1_C4烧基; ^2彼此獨立表示氧原子或硫原子;, J為相同或不同,表示氫原子 η表示〇至4之整數; u牙、你丁义―鼠甲丞,(wherein Υι denotes C1-C6 alkoxy, C1-C6 haloalkoxy, C1~ thiol, Cl-C6 thiol, C1-C6 alkylsulfinyl, C1_C6 6 cadaveric Sulfonyl, Cl—C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl; where Y5 represents a halogen atom, a Cl—C6 alkyl group, a C1-C6 haloalkyl group, C1~C6 45 200836629 =6 , a-thio group, ketone group γ group == brewing group, C1, silk group, and 24 may be the same or different, and represent a hydrogen atom, a halogen atom, and C1-C6 Y3 represents a halogen atom. (Compound IY) The formula (IIA1=; to "," independently represents a hydrogen atom or a C1_C4 alkyl group; ^2 independently represents an oxygen atom or a sulfur atom; and J is the same or different, and represents a hydrogen atom η represents 〇 to 4 integer; u tooth, you Dingyi - mouse armor,
Qi為苯基, ’ 执其、Γ9 上烷ί C2 — C4烯基、C2 —C4鹵烯基、C2—C4 二乂 C8 環烷基、C3-C8 _烷基、α 氧基、C1—c3燒硫基、C1—C3鹵烧 Ϊϋ : 練基、C1 —C3 *烧基亞顧基、C1-C3 燒基石頁喊、a-C3自絲麵基、C1—C4餅基、 ί 基、絲、C1—C4 顧基、C1—C4 “、 烷镟氧基、C1-C4鹵燒羰氧基、C1_C4烷氧幾基、以 -C4 S燒氧幾基、C1 —C4絲胺基、α—C4函燒幾胺基、Q -C4烷基石黃酸氧基、C1 —C4自燒基石黃醯氧基、芳石黃釀氧基 氟硫烷基或苯基中相同或不同之1個以上取代基, 雜環基(在此之雜環基表示吡啡基、吡啶基、N—氧化吡啶美、 嘧啶基、嗒啡基、呋喃基、噻吩基、噚唑基、異噚唑基'噚 基、嗟唾基、異嗟峻基、嗟二唾基、咖各基、^坐基:三二-味 吡唑基、四唑基、2,3 —二氫一苯并K4]二噚畊基、苯并[丨 46 200836629 tr坐基、四氫ϋ底喃基或二氳旅鳴基。) 或, 取代雜環基:具擇自於鹵素原子、C1 — C4絲、C1 — C4齒烧 基、經取代之C1-C4烧基、C2 —C4烯基、C2—C4鹵烯基、C2 -C4炔基、C2-C4鹵炔基、C3-C8環烧基、C3-C8 _環烷基、 ci—c3烧氧基、ci—c3 i烷氧基、C1_C3烷硫基、C1_C3鹵 烧硫基、C1 一C3烧基亞磺醯基、C1 — C3鹵烷基亞磺醯基、C1 — C3院基石頁基、Cl — C3鹵烧基石黃酿基、ci — C4烧胺基、二C1 yC4烧胺基、氰基、硝基、羥基、— 羰基、C1 — C4鹵烷Qi is phenyl, 'execution, Γ9, alkane C2 - C4 alkenyl, C2-C4 haloalkenyl, C2-C4 di-C8 cycloalkyl, C3-C8-alkyl, alpha oxy, C1-c3 Sulfur-burning, C1-C3 halogen-burning Ϊϋ: base, C1—C3* 烧基亚基基, C1-C3 burning base stone shouting, a-C3 self-filament base, C1-C4 base, ί base, silk , C1-C4 Guji, C1-C4", alkyl alkoxy, C1-C4 halogen carbonyloxy, C1_C4 alkoxy group, -C4 S alkoxy group, C1-C4 silk amine, α- C4 calcined amino group, Q-C4 alkyl tartrazine oxy group, C1-C4 self-calcining sulphate xanthoxy group, aryl stone yellow oxy fluorosulfanyl group or phenyl group with the same or different one or more substitutions A heterocyclic group (wherein a heterocyclic group means pyridyl, pyridyl, N-oxidized pyridyl, pyrimidinyl, morphinyl, furyl, thienyl, oxazolyl, isoxazolyl'yl) , 嗟 基 、, 嗟 嗟 嗟, 嗟 唾 、 、, 各 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基Benzene [丨46 200836629 tr sitin, tetrahydroindenyl or diterpene). or, substituted heterocyclic: From halogen atom, C1 - C4 filament, C1 - C4 dentate, substituted C1-C4 alkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 halo Alkynyl, C3-C8 cycloalkyl, C3-C8-cycloalkyl, ci-c3 alkoxy, ci-c3 i alkoxy, C1_C3 alkylthio, C1_C3 halogen thiol, C1 - C3 alkyl Sulfonyl, C1 - C3 haloalkyl sulfinyl, C1 - C3, sulphate, Cl - C3, sulphur, yellow, ci - C4, amine, cyano, cyano Nitro, hydroxy, carbonyl, C1 - C4 halane
幾基、C1-C4烧羰氧基、C1 一C4 _烷羰氧基、ci 一C4烷氧幾基、 C1—C4 _烷氧羰基、C1 一C4烷羰胺基、ci一C4鹵烷羰胺基、 C1二C4烷基續醯氧基、C1 一C4 i烧基確醯氧基、芳續醯氧基、 五氟硫烷基或苯基中相同或不同之1個以上取代基(在此之雜環基 表不吡畊基、吡啶基、N—氧化吡啶基、嘧啶基、嗒畊基、呋喃基、 噻吩基、噚唑基、異噚唑基、噚二唑基、噻唑基、異噻唑基、噻 一=基、°比嘻基、咪唾基、三π坐基、ϋ比唾基、四唾基、2,3—二氫 ^并[1,4]二噚畊基、苯并[1,3]二噚唑基、四氫哌喃基或二氫哌 喃基。乂 仏為通式(4)a few groups, a C1-C4 carbonyloxy group, a C1-C4-alkylcarbonyloxy group, a ci-C4 alkoxy group, a C1-C4-alkoxycarbonyl group, a C1-C4 alkylcarbonylamino group, a ci-C4 haloalkyl carbonyl group Amino, C1 di-C4 alkyl decyloxy, C1 - C4 i decyloxy, aryl methoxy, pentafluorosulfanyl or phenyl, the same or different one or more substituents The heterocyclic group is not pyridinyl, pyridyl, N-oxidized pyridyl, pyrimidinyl, hydrazine, furyl, thienyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, Isothiazolyl, thiazide=yl, 嘻 嘻 、, imidazo, tri-π, ϋ, 唾, 四, 四, 四, 四, 2, 2, 2, 2, 2 Benzo[1,3]dioxazolyl, tetrahydropentanyl or dihydropiperidyl. 乂仏 is of formula (4)
I、Υ5可為相同或不同’表示鹵素原子、Ci —C6产美、C1 燒基、C1—C6嫁氧基、C1—C6 4絲基、ci_=烧硫 i醯自絲基、紐科縣、C1—c6齡基亞 £· 土、1— C6烷基磺醯基、Cl —C6 4烧基石黃醯基、氰基、硝 Y2、Y4可為相同或不同,表示氫原子、鹵素原子、C1_C6 47 200836629 烧基;Ra表示鹵素原子或經基;I, Υ5 may be the same or different 'representing halogen atom, Ci-C6 producing beauty, C1 burning base, C1-C6 grafting oxygen, C1-C6 4 silk base, ci_= burning sulfur i醯 from silk base, New County , C1—c6 age bases, soils, 1-C6 alkylsulfonyl groups, Cl—C6 4 basestones, sulfonyl groups, cyano groups, nitrates Y2, Y4, which may be the same or different, represent a hydrogen atom, a halogen atom, C1_C6 47 200836629 alkyl; Ra represents a halogen atom or a meridine;
Rb、Rc各自獨立地表示氳原子、羥基、鹵 基,至少Rb、Rc其中之一具“固以上气早’、、,或C1 — C6鹵垸 原子或碘原子。)。 ^ ’、子、羥基、氯原子、溴 (化合物V〜VIII) 前述化合物I〜IV中鳴^少其中 物。 為Cl〜C4烷基化合 通式(1)或通式(5)表不之化合物可以用 通^)下製造方法所不通式中,Q2與前述[1]中之q2 同義,或為Rb and Rc each independently represent a halogen atom, a hydroxyl group, a halogen group, and at least one of Rb and Rc has a "solid gas early", or a C1 - C6 halogen atom or an iodine atom.) ^ ', sub, Hydroxy group, chlorine atom, bromine (compounds V to VIII) Among the above-mentioned compounds I to IV, the compound is a compound of the above-mentioned compounds I to IV. It is a compound of the formula (1) or the formula (5) which can be used for the alkyl group of C1 to C4. In the general formula of the manufacturing method, Q2 is synonymous with q2 in the above [1], or
(2) (式中,Yi、Y2、Y3 Ys同義。)或通式(3) 'Y4'Y5^Wi4[l]t^Y^Y2.Y3.Y4(2) (wherein, Yi, Y2, Y3 Ys are synonymous.) or general formula (3) 'Y4'Y5^Wi4[l]t^Y^Y2.Y3.Y4
YY
(3) (ί造中方ΪΓ7、Υ8、Υ9與蝴^ 48 200836629(3) (The Chinese party ΪΓ 7, Υ 8, Υ 9 and butterfly ^ 48 200836629
α〇) 還原反應 P<>n ¢21)Α〇) reduction reaction P<>n ¢21)
a2、a3、a4、Gl、r2 Rl、r2、x、n、Qi、Q2與前述[1]中之 Al 原子=等具‘’義,L表示齒: 益丄.、通式(l9)+通式(20) 一通式(21) 劑中i無溶ΖίΊΐΐ之化合物與通式(20)表示之化合祕 用鹼。 ^ 衣化通式(21)表不之化合物。本步驟亦可 例如,水、苯、甲苯 二乙輕、二概、四ΐϊ南m四/化碳等南素化_ 乙酸乙醋、乙酸丁_類;甲狀或德 等腈紙3-H2 —等二胺等ϋ胺類;乙崩 使用或將2種以上混合使用。 、、’谷蜊,此等溶劑可單獨 又,鹼例如··三乙胺、三正丁基胺、吡 等有機鹼類、氫氧化鈉、氫氧化鉀等 〜一甲基胺基吡咬 碳酸鉀等碳酸鹽類;磷酸一氫二鉀、確^ ^鈿梦金屬類;碳酸氫鈉、 氫化驗金屬魏;f醇納、乙醇納等驗膝碌酸鹽類;氫化勒等 對於通式(19)表示之化合物,於^轉。此等驗,相 擇使用即可。 吴耳當量之範園適當選 49 200836629 反應溫度,從— 2Gt:〜使麟劑之回流溫度,反應時間,從 數为鐘至96小時之範圍各適當選擇即可。 /例如,通式(19)表示之化合物為間靖基芳香族緩酸鹵化物之情 形,間硝基芳香族羧酸鹵化物可藉由使對應芳香族羧酸與鹵素化 ,反,而輕易地製造。鹵素化劑,例如,亞硫醯氯、亞硫醯溴、 輕基氯化碟、草醯氯、三氯化磷等鹵素化劑。 另一方面,不使用鹵素化劑,而藉由使通式(19)表示之化合物 與通式(20)表示之化合物反應,能製造通式(21)表示之化合物。例 如’ Chem· Ber.p· 788(1970)記載之製造方法,顯示亦即適當使 -經基苯并三岭添加劑,並使用耶,—二環己基^醯^ 縮合劑的方法。此情形中使用之其他縮合劑,例如丨一乙基_3一 (3 —二甲基胺基丙基)羰二醯亞胺、,一羰基雙—1H_咪唑等。 又’製造通式(21)表示之化合物之其他方法,例如使用氯甲酸 酉曰類之此合酸酐法,藉由依照j· Am· chem· Soc· ρ·5012(1967)之方 法二可製造通式(21)表示之化合物。此情形使用之氯甲酸酯類,例 如氯甲酸異丁酯、氯曱酸異丙酯等,氣曱酸§|類以外,例如氯化 二乙基乙酿基、氯化三曱基乙醯基等。 使用縮合劑之方法、混合贿法,均不限於前敎獻記載之 二別、反應溫度、反麟間,只錢使料顯著妨礙適當反應進 彳 性溶劑即可’關於反應温度、反應時間,亦視反應進行適 當選擇即可。 1 一⑼:通式(21)—通式(22) ,式(^表不之化合物,可藉由還原反應,得到通式(22)表示 物。遠原反應,例如,使用加氫反應之方法及使用金屬化 合物、氯化錫(1)(無水物)、鐵粉、鋅粉等)之方法。 法’可於適當溶劑巾,觸媒存在下,於常壓下或加壓 :鼠錢目巾反應。觸媒例如,κ雜麟、倫尼鎳等鎳 觸女气觸,、釕觸媒、铑觸媒、銘觸媒等,溶劑例如水、甲醇、 乙醇ά類;苯、曱料芳香族烴類;m四氳柄等鍵狀 50 200836629 乙_旨類。動從αΐ〜1_,反應溫度從- 久白、^二―之回m反應喃從數分鐘至96小時之範圍 各U選脚可,能有效率地製造通式(22)之化合物。乾圍 V哉 方法’例如以n〇rganiC Syntheses,,Coil. ν〇1.ΙΠ P453 载^^,使用氯化錫W(無水物)作為金屬化合物使用之方法。 — ㈣.通式(22)+通式(23)—通式(24) Ϊ由ΐίί(ϊ21 絲之化合物與通式(23)表示之化合物於溶劑中反 w ^衣k通式(24)表示之化合物。本步驟亦可使用鹼。 溶劑,只要不顯著妨礙本反應進行者即可,例如,水、苯、 二I笨等t香族烴類;二氯甲烧、氯仿、四氯化碳等齒素化 、四氫Π夫喃、丨,2 —"甲氧基乙烧等鏈狀或環— ^巧,乙k乙醋、乙酸丁g旨等醋類;甲醇、乙醇等醇氣丙綱、甲基 ϋϊ、環己嗣等嗣類;二曱基甲酿胺、二曱基乙_等醯胺氟 猜類;1,3~二曱基—2 —咖域酮等鈍性溶劑,此等溶劑可 早獨使用或將2種以上混合使用。 耸右例如:三乙胺、三正丁基胺、咖定、4—二甲基胺基咖定 ^有機鹼類、氫氧化鈉、氫氧化鉀等氫氧化鹼金屬類;碳酸氫鈉、 石反酸鉀等碳酸鹽類;磷酸一氫二鉀、磷酸三鈉等麟 氫化驗金屬鹽類;甲_、乙醇鱗驗金屬醇鹽_。 對於通式(22)表示之化合物,在_〜5倍莫耳當量之範圍適當選 ^使用即可。反應溫度’從— 2Gt:〜使聽劑之回流溫度,反應 間攸數为鐘至96小時之範圍適當選擇即可。又,亦可使用前述 1 一(i)記載之使用縮合劑之方法、混合酸酐法製造。 —丨一㈣:通式(24)+通式(25)—通式(26) ,由使通式(24)表示之化合物與通式(25)表示之化合物於溶劑中或 幾/谷(反應’可製造通式(26)表示之化合物。通式(25)表示之化合 物,例如碘甲烷、蛾乙烧、漠化正丙烷等鹵烷類、氯化乙醯基^ 鹵素化基類等。又,本步驟可使用適當的驗或溶劑,該驗或溶 劑’例如m述1一(i)例示者。關於反應溫度、反應時間等,亦可依 51- 200836629 照前述1 一 (i)之例示。 又’就其他方法而言,藉由將通式(25)表示之化合物改為將二 曱基硫酸、二乙基硫酸等烷基化劑與通式(24)表示之化合物反應, 亦能製造通式(26)表示之化合物。 製造方法2A2, a3, a4, Gl, r2 Rl, r2, x, n, Qi, Q2 have the same meaning as the Al atom in the above [1], and L means a tooth: Yiyi., general formula (l9)+ In the formula (20), the compound of the formula (21) is a compound which is not dissolved and which is represented by the formula (20). ^ Compounds of the formula (21). This step can also be, for example, water, benzene, toluene, light, two, four, south, m, and carbon, etc. _acetic acid, vinegar, acetic acid, butyl ketone, ketone or denitrile paper 3-H2 - a guanamine such as a diamine; or a mixture of two or more types. , '谷蜊, these solvents can be used alone, alkali such as · triethylamine, tri-n-butylamine, pyridin and other organic bases, sodium hydroxide, potassium hydroxide, etc. ~ monomethylaminopyrazole Potassium and other carbonates; dipotassium phosphate, ^ ^ 钿 金属 metal; sodium bicarbonate, hydrogenation test metal Wei; f-alcohol, ethanol and other test knee acid salts; hydrogenation and so on for the general formula ( 19) The compound indicated is transferred to ^. For this test, you can use it as you like. The appropriate choice for the Wuer Equivalent Fan Park is to be selected. 49 200836629 Reaction temperature, from -2Gt: ~ The reflow temperature of the arsenic, the reaction time, from the number of clocks to 96 hours, the appropriate choice. / For example, in the case where the compound represented by the formula (19) is a mesenyl-based aromatic acid-lowering halide, the m-nitroaromatic carboxylic acid halide can be easily obtained by halogenating the corresponding aromatic carboxylic acid. Manufacturing. A halogenating agent such as a halogenating agent such as sulfinium chloride, sulfinium bromide, light-based chlorinated dish, grass chloroform, phosphorus trichloride or the like. On the other hand, a compound represented by the formula (21) can be produced by reacting a compound represented by the formula (19) with a compound represented by the formula (20) without using a halogenating agent. For example, the production method described in 'Chem. Ber.p. 788 (1970) shows a method in which a benzotriazole additive is suitably used and a ruthenium-dicyclohexyl condensate is used. Other condensing agents used in this case are, for example, monoethyl-3-(3-dimethylaminopropyl)carbonyldiimide, monocarbonylbis-1H-imidazole and the like. Further, another method of producing a compound represented by the formula (21), for example, a method using the hydrazine chloroformate, can be produced by the method according to J. Am. Chem. Soc. ρ. 5012 (1967) A compound represented by the formula (21). The chloroformate used in this case, for example, isobutyl chloroformate, isopropyl chlorate, etc., other than gas phthalic acid § |, for example, diethyl ethyl chlorinated, trimethyl ethyl chloride Wait. The method of using a condensing agent and the method of mixing bribes are not limited to the two types of the former transcripts, the reaction temperature, and the reverse lining, and only the money makes the material significantly hinder the proper reaction of the hydrazine solvent, 'about the reaction temperature, the reaction time, It is also possible to make an appropriate selection depending on the reaction. 1 - (9): a compound of the formula (21) - formula (22), which is represented by the formula (2), which can be represented by the reduction reaction to give a compound of the formula (22). The far-end reaction, for example, using a hydrogenation reaction The method and the method of using a metal compound, tin chloride (1) (anhydrous), iron powder, zinc powder, etc.). The method can be carried out under normal pressure or under pressure in the presence of a suitable solvent towel or a catalyst: a mouse money towel. Catalysts such as κ heterolin, Lenny nickel and other nickel-touch female gas, ruthenium catalyst, ruthenium catalyst, and sensitizer, solvents such as water, methanol, ethanol oximes; ;m four handles and other key shapes 50 200836629 B. The reaction is carried out from αΐ~1_, and the reaction temperature is from -the white, the second, and the m reaction is from the range of several minutes to 96 hours. Each U can be selected to efficiently produce the compound of the formula (22). The dry 哉V哉 method 'for example, n〇rganiC Syntheses, Coil. ν〇1.ΙΠ P453 is used, and tin chloride W (anhydrous) is used as a metal compound. — (4). General formula (22) + general formula (23) - general formula (24) Ϊ ΐίί (ϊ21 silk compound and compound represented by formula (23) in the solvent anti-w^ clothing k general formula (24) The compound may be used in this step. The solvent may be used as long as it does not significantly hinder the progress of the reaction, for example, water, benzene, di-I stupid, etc.; dichloromethane, chloroform, tetrachlorination Carbon or other dentate, tetrahydrofurfuran, hydrazine, 2 -" methoxy ethene, etc. chain or ring - 巧, 乙 k 乙 vinegar, acetic acid butyl g, etc.; methanol, ethanol, etc. Anthraquinones such as aglycone, methylhydrazine, cyclohexanide, etc.; diterpene-based amide, dimercapto-ethyl hydrazine, etc.; 1,3~dimercapto-2, ketone, etc. Solvents, these solvents may be used alone or in combination of two or more. Shallow right, for example: triethylamine, tri-n-butylamine, caiding, 4-dimethylamino-based caffeine, organic bases, hydroxide Alkali metal hydroxides such as sodium and potassium hydroxide; carbonates such as sodium hydrogencarbonate and potassium citrate; metal hydrides such as dihydrogen phosphate monobasic phosphate and trisodium phosphate; Salt _. For the general formula (22) The content may be appropriately selected in the range of _~5 times the molar equivalent. The reaction temperature may be appropriately selected from the range of -2 Gt:~ to the reflux temperature of the listener, and the number of turns between the reactions is from clock to 96 hours. Further, it can also be produced by the method using a condensing agent described in the above (i), or by a mixed acid anhydride method. - 丨 (4): Formula (24) + Formula (25) - Formula (26) a compound represented by the formula (24) and a compound represented by the formula (25) in a solvent or a few/valleys (reactions can produce a compound represented by the formula (26). A compound represented by the formula (25), such as methyl iodide, Molybdenum, desertified propane and other halogenated alkanes, chlorinated ethylidene groups, halogenated groups, etc. In addition, this step may use an appropriate test or solvent, such as m (1) For example, the reaction temperature, the reaction time, and the like may be exemplified by the above-mentioned 1 (i) according to 51-200836629. Further, in other methods, the compound represented by the general formula (25) is changed to An alkylating agent such as mercaptosulfuric acid or diethylsulfonic acid can be reacted with a compound represented by the formula (24) to produce a compound represented by the formula (26). Production Method 2
響 (通式(20)、通式(23)及通式(27)〜通式(30)中,E表示一C(=In the formula (20), the formula (23) and the formula (27) to the formula (30), E represents a C (=
Gi)-或-S02-,^、A2、A3、A4、G、G2、&、R2、X、n、Gi)- or -S02-,^, A2, A3, A4, G, G2, &, R2, X, n,
Qi、Q2 與前述[1]中之 Ai、A2、A3、A4、G]L、G2、、R2、x、n、Qi, Q2 and Ai, A2, A3, A4, G]L, G2, R2, x, n in the above [1]
Qi^Q2同義,L表示鹵素原子、羥基等具脱離能力之官能基,Hal 表示鹵素原子。) 2—(i) ··通式(27)+ 通式(23)—通式(28) 以通式(27)表示之化合物作為出發原料,依照前述1一①記載之條 件’與通式(23)表示之化合物反應,能製造通式(28)表示之化合物。 2~(ii):通式(28)—通式(29) • 藉^使通式(28)表示之化合物與亞硫醯氯、草醯氯、光氣、羥基氯 、五氯化磷、三氯化磷、亞硫醯溴、三溴化磷、二乙基胺基 硫二氟化物等反應的公知的常法,可製造通式(29)表示之化合物。 —2 — (m):通式(29)+ 通式(2〇)—通式(3〇) 藉由將通式(29)表示之化合物與通式(20)表示之化合物,依照卜 (1)記載之條件反應,可製造通式(30)表示之化合物。 _ 2~(iV):通式(28)+ 通式(2〇)—通式(3〇) =通式(28)表示之化合物,依照前述丨一①記載之使用縮合劑之條 =或使用混合酸酐法之條件,與通式(2〇)表示之化合物反應,可製 k通式(30)表示之化合物。 製造方法3 52 200836629Qi^Q2 is synonymous, and L represents a functional group having a detachment ability such as a halogen atom or a hydroxyl group, and Hal represents a halogen atom. 2—(i) ·· (27)+ Formula (23)—Formula (28) The compound represented by the formula (27) is used as a starting material, and the conditions and the formula are as described in the above 1-1. The compound represented by the formula (28) can be produced by reacting the compound represented by (23). 2~(ii): General formula (28) - General formula (29) • By using the compound represented by the general formula (28) with sulfinium chloride, chloroform, phosgene, hydroxy chloride, phosphorus pentachloride, A compound represented by the formula (29) can be produced by a known conventional method of a reaction such as phosphorus trichloride, sulfinium bromide, phosphorus tribromide or diethylaminosulfur difluoride. — 2 — (m): Formula (29) + Formula (2〇)—Formula (3〇) By using a compound represented by the formula (29) and a compound represented by the formula (20), 1) The conditions described in the reaction can produce a compound represented by the formula (30). _ 2~(iV): general formula (28) + general formula (2〇) - general formula (3〇) = a compound represented by the formula (28), according to the above-mentioned item 1, the use of a condensing agent strip = or The compound represented by the formula (30) can be produced by reacting with a compound represented by the formula (2) using the conditions of the mixed acid anhydride method. Manufacturing Method 3 52 200836629
A aA a
Ο ^ 拉威生試藥Ο ^ Rawweisheng test
% X mn β2) C23) aA4^Γγ' OOn 1! 闕 (通式(23)及通式(31)〜通式(33)中,Ε表示—c( = Gi)—或〜 lit 2„、Gl、Rl、R2、X、n、Ql、Q2_,W〒 鹵素原子、羥基等具有脱離能力之官能基。) 3—①:通式(31)—通式(32) ,照Synthesis第偏頁(1"3年)及咖此仏第η9頁(携 ,之公知條件,將通却1)絲德合物無威生試藥反應,可製 ,通式(32)表示之化合物。溶劑、反應溫度等條件,不限 ^ 獻記載者。 寸乂 —3-⑻:通式(32)+通式(23)—通式(33) 藉由將通式(32)表示之化合物與通式(23)表示之化合物,依照前述 卜®記載之條件反應,可製造通式(33)表示之化合物。 製造方法4% X mn β2) C23) aA4^Γγ' OOn 1! 阙 (in the general formula (23) and the general formula (31) to the general formula (33), Ε represents -c( = Gi)- or ~ lit 2„, Gl, Rl, R2, X, n, Ql, Q2_, W〒 a halogen atom, a hydroxyl group, etc. having a dissociable functional group.) 3-1: General formula (31) - general formula (32), according to Synthesis Page (1"3 years) and 仏9 page (carrying, the known conditions, will pass 1) silk compound without Weisheng reagent reaction, can be prepared, the compound represented by the formula (32). Solvent The conditions such as the reaction temperature are not limited to those described above. Inch 乂 - 3-(8): Formula (32) + Formula (23) - Formula (33) By using the compound represented by the formula (32) The compound represented by the formula (23) can be produced according to the conditions described in the above-mentioned product, and the compound represented by the formula (33) can be produced.
(35) (38) ^ (通式(34)至通式(36)中,\、A2、A3、A4、Rj、R2、X、n、(35) (38) ^ (In the general formula (34) to the general formula (36), \, A2, A3, A4, Rj, R2, X, n,
Qi、、Q2 與前述[1]中之 Ai、A2、A3、A4、K、r2、X、n、Qi、& 同義。)從通式(34)表示之化合物,依據前述3一①記載之條件,2 可製造通式(35)及通式(36)表示之化合物。溶劑、反應溫度等條件, 不限於文獻記載者。該等2個化合物,可藉矽膠管柱層析等公知 53 200836629 的分離精氣技術,輕易地分離精製 製造方法5 "Qi, Q2 are synonymous with Ai, A2, A3, A4, K, r2, X, n, Qi, & in the above [1]. From the compound represented by the formula (34), the compound represented by the formula (35) and the formula (36) can be produced according to the conditions described in the above 3-1. The conditions such as the solvent and the reaction temperature are not limited to those described in the literature. These two compounds can be easily separated and refined by the known separation technology of 53 200836629, such as rubber column chromatography.
〜^令1 ^A^Y' (X)n i (39) (23) R2~^令1 ^A^Y' (X)n i (39) (23) R2
,'2人' R (X)n ό °2 (38) >On Ji (37), '2 person' R (X)n ό °2 (38) >On Ji (37)
(通式(23)及通式(37)〜通式(39)中,e 二 S02-,、、A2、a3、a4、。、&、R 述⑴中之“ A3、A4、Gl、G2、Ri、Wn、Ql、Q2^ 義’ L表示鹵素原子、羥基等具有脱離二心、Qi、Q2同 5-(i):通式(37卜通式⑽ 之“基。) 依照例如J· Org· Chem· Ρ·280(1958)記載之你彼你阳— 化反應’可製造通式(示之丄載 ΪΓ文獻記載者’只要是使用不顯著妨礙適當反ΐ進行之I性溶 w p可,關於反應溫度、反應時間,亦視反應進行適當選擇即可。 .又’胺基化劑除氨以外,亦可例示如曱基胺、乙基胺等。 ^ 5〜⑼··通式(38)+通式(23) —通式(39) 藉由將通式(38)表示之化合物與通式(23)表示之化合物,依照前述 i — ®記载之條件反應,可製造通式(39)表示之化合物。 製造方法6 54 200836629(In the general formula (23) and the general formula (37) to the general formula (39), e 2 S02-, , A2, a3, a4, ., &, R, (1), "A3, A4, Gl, G2, Ri, Wn, Q1, Q2^ meaning 'L" means that a halogen atom, a hydroxyl group or the like has a cleavage center, Qi, Q2, and 5-(i): a formula (37) of a formula (10). J. Org·Chem· Ρ·280 (1958) describes the yin-chemical reaction of the yin-chemical reaction (shown in the literature) as long as it is used without any significant impediment to proper ruminant Wp can be used, and the reaction temperature and reaction time can be appropriately selected depending on the reaction. Further, in addition to ammonia, the aminating agent can also be exemplified by mercaptoamine, ethylamine, etc. ^ 5~(9)·· Formula (38) + Formula (23) - Formula (39) By reacting a compound represented by the formula (38) with a compound represented by the formula (23), it can be produced according to the conditions described in the above i- a compound represented by the formula (39). Manufacturing method 6 54 200836629
(43,2) <44-a> (通式(40)至通式(44—2)中,R2、Y2、Y4與前述[1]中之R2、 Y2、Y4同義,Yi'Ys各自獨立地表示氫原子、甲基、氣原子、溴 原子、碘原子,Rf表示Cl —C6全氟烷基,m為1、2。) 6 — (i) ·通式(4〇)+ 通式(41)—通式(42) 依照J· Fluorine Chem· ρ·207(1994)記載之方法,藉由使通式(4〇)表 示之胺硫基酴類與通式(41 )表示之蛾化鹵烧基反應,可製造通式 (42)表示之化合物。(43, 2) <44-a> (In the general formula (40) to the general formula (44-2), R2, Y2, and Y4 are synonymous with R2, Y2, and Y4 in the above [1], and each of Yi'Ys Independently represents a hydrogen atom, a methyl group, a gas atom, a bromine atom, or an iodine atom, and Rf represents a Cl—C6 perfluoroalkyl group, and m is 1, 2.) 6 — (i) • Formula (4〇)+ (41) - General formula (42) According to the method described in J. Fluorine Chem. ρ. 207 (1994), the amine thioguanidine represented by the general formula (4〇) and the moth represented by the general formula (41) The compound represented by the formula (42) can be produced by a halogen group reaction.
通式(41)表示之化合物(埃化鹵烷),例如,碘化三氟曱烷、碘 化五氟乙烷、碘化七氟一正丙烷、碘化七氟異丙烷、碘化九氟一 正丁烷、碘化九氟一2—丁烷等,該等可相對於通式(4〇)表示之化 ,合物,於1〜10倍莫耳當量之範圍適當使用。本步驟使用之溶劑 不限於前述文獻記載之溶劑,其溶劑只要不顯著妨礙本反應進行 即可,例如,水、苯、甲苯、二甲苯等芳香族烴類;二氯曱燒、氯 仿三四氯化碳等鹵素化烴類;二乙醚、二噚烷、四氳呋喃、U—二 甲氧基乙烧專鏈狀或環狀醚類;乙酸乙酯、乙酸丁醋等酯類甲醇、 乙醇等醇類;丙酮、甲基異丁細、環己_酮類;二甲基甲驢胺、 二甲基乙醯胺等醯胺類;乙腈等腈類;U —二甲基一2一味唑啶晒、 If魏三醯胺等鈍性賴,此等溶劑可單獨使用或將2種以 ^ δ使用、。尤其極性溶雜佳。反應溫度,可從〜使用 4之酿雜、反應_可從數分鐘至%小時之細分別適當 55 200836629 選擇。 6 — (ii):通式(42)—通式(43)a compound represented by the formula (41) (an alkyl halide), for example, trifluorodecane iodide, pentafluoroethane iodide, heptafluoro-n-propane iodide, heptafluoroisopropane iodide, nonafluoroheptide Or n-butane, hexafluoro-2-butane iodide, etc., which can be suitably used in the range of 1 to 10 times the molar equivalent of the compound represented by the formula (4). The solvent to be used in this step is not limited to the solvent described in the above document, and the solvent thereof may be, for example, water, aromatic hydrocarbons such as benzene, toluene or xylene; dichlorohydrazine or chloroform tris. Halogenated hydrocarbons such as carbon; diethyl ether, dioxane, tetrahydrofuran, U-dimethoxyethane-specific chain or cyclic ether; esters such as ethyl acetate and butyl acetate, methanol, ethanol, etc. Alcohols; acetone, methyl isobutylene, cyclohexanone; guanamines such as dimethylformamide, dimethylacetamide; nitriles such as acetonitrile; U-dimethyl-2-oxazolidine For example, sunbatch, If triterpenoid, etc., these solvents may be used alone or in combination with two kinds of δ. Especially the polar solution is good. The reaction temperature can be selected from ~ used 4, the reaction _ can be from a few minutes to the minute of the appropriate 55 200836629 selection. 6 — (ii): General formula (42)—general formula (43)
自素糊,可製造通_表示德合物,例如,可 便甩 Synth.C〇_UILp 126 1(1989)記載之方法。 J 祕ί ΐί劑例如’氯、溴、填、N—氯琥_酿亞胺、N-、、拿试 N—魏__亞胺等,可相對輯式 不之化。物,以1〜10倍莫耳當量之範圍適當使用。 t步驟亦可使用溶劑,使用之溶劑不限 齊,此溶劑只要不顯著妨礙本反應進行即可,^文=1之ς 四氣咬喃、u~二甲氧基乙垸等鏈狀或環狀 t j二3旨、j酸丁輯等峨曱醇、乙醇等醇細酮、ί基显 =腈類;u—二甲基—2—咪唑啶酮 $ :此等溶劑可單獨使用或將2種以上混合使用 =,溫度,可從—2叱〜使用溶劑之回流溫度,反應 寸間可攸數分鐘至96小時之範圍適當選擇。 ’ ^ 1一邱):通式(43)—通式(44) ^適當氧化劑,可製造通式(μ)麵之化合物。例如, 丄etrahedronLettp.49 55(1994)記載之方法。 几氧化劑例如,間氯過苯甲酸等有機過酸、 以―溴琥珀酸醯亞胺、亞碘醯基苄基、次亞氯酸第三丁酯等。、 本步=使狀溶劑,不限於前述文獻記載之溶劑,該溶劑只 f疋不顯者妨礙本反應進行者即可,此等溶劑可單獨使用 •〜^上混合使用。尤其極性溶劑較佳。反應溫度5從一2〇t:〜使 =劑之喊溫度、反麟目從數分鐘至96小叙細各自適當 選擇即可。 56 1 —㈣··通式(43)—通式(43—2) 200836629 藉由使用適當曱基化劑,可從通式(43)表示之化合物製造通式(43 - --------·2)(式中,Yi、Y5其中之一必需表示曱基。)表示之化合物。此方 法例如 Tetrahedron Lett ρ·6237(2000)記載之方法。 6 — (ν) ··通式(43 — 2)—通式(44一2) • 依照前述6 — (iii)記載之方法,可製造通式(44~2)(式中,至少Υ!、 、 Y5其中之一必需表示甲基。)表示之化合物。 又,使用通式(43)、通式(44)、通式(43 — 2)或通式(44一2)表示 之化合物,並藉由適當選擇前述所示方法,可製造通式(1)或通式 (5)表示之化合物。 以同樣方法,可製造通式(2)中之I、Υ2、γ4、¥5為C1—C6 全氟烧硫基、Cl —C6全氟烧基亞續醯基、Cl —C6全氟烧基績酸 基之以通式(1)或通式(5)表示之化合物。 土 ’、 製造方法7From the plain paste, it is possible to produce a compound, for example, a method described in Synth. C〇_UILp 126 1 (1989). J ί ΐ ΐ 剂 例如 例如 例如 例如 ’ ’ ’ 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯 氯The substance is suitably used in the range of 1 to 10 times the molar equivalent. The solvent can also be used in the t step, and the solvent to be used is not limited. The solvent can be carried out as long as it does not significantly hinder the reaction, and the chain or ring of the gas is entangled, and the ring is ring-shaped or ring-shaped. t 3 二 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 The above mixed use =, the temperature, can be selected from -2 叱 ~ using the reflux temperature of the solvent, the reaction range can be selected from the range of several minutes to 96 hours. ' ^ 1 Qiu): Formula (43) - Formula (44) ^ Suitable oxidizing agent, which can produce a compound of the formula (μ). For example, the method described in 丄 etrahedron Lettp. 49 55 (1994). A few oxidizing agents are, for example, organic peracids such as m-chloroperbenzoic acid, quinone iodide bromide, iodonium benzyl, and tert-butyl hypochlorite. In this step, the solvent is not limited to the solvent described in the above-mentioned literature, and the solvent may be used only if it does not interfere with the reaction. These solvents may be used alone or in combination. Especially polar solvents are preferred. The reaction temperature is from 2 to 2:t to make the temperature of the agent, and the reverse phase is selected from several minutes to 96 small details. 56 1 - (4) · Formula (43) - Formula (43-2) 200836629 By using a suitable thiolating agent, a compound of the formula (43) can be produced from the compound of the formula (43). ---·2) (wherein, one of Yi and Y5 must represent a thiol group.) A compound represented. This method is, for example, the method described in Tetrahedron Lett ρ. 6237 (2000). 6 — (ν) · · Formula (43-2)—Formula (44-2) • According to the method described in 6—(iii) above, the formula (44~2) can be produced (in the formula, at least Υ! One of Y, and Y5 must represent a compound represented by a methyl group.). Further, a compound represented by the formula (43), the formula (44), the formula (43-2) or the formula (44-2) can be produced, and the formula (1) can be produced by appropriately selecting the method described above. Or a compound represented by the formula (5). In the same manner, I, Υ2, γ4, and ¥5 in the formula (2) can be produced as a C1-C6 perfluorosulfothio group, a Cl-C6 perfluoroalkyl sulfhydryl group, and a Cl-C6 perfluoroalkyl group. The acid group is a compound represented by the formula (1) or the formula (5). Soil ‘, manufacturing method 7
(4?)(4?)
ηΤγ6)^;(,47)' 5R2'Y2'Y4 2“)猎式(45)表示之化合物作為出發原料,“祕、f造方 方法’可製造通式⑴或通式⑶表示之化』㈣㈣胸述所不 全氣為心⑶ 基之,⑴峨、C1、C6纖細 57 200836629 λΛ; 〇2 % (Χ)π (48) 將(通式(48)及通式(49)中,(4S> Q2與前述[1]中之Ά'α 1 2、3、A4、X、n、G2、R2、 式(48)表示之化合物與溶劑3 ) 4南'nj、1、(¾同羲。)通 (49)表示之化合物。 使用驗”反應劑反應,可製造通式 甲著妨礙本反應進行即可,例如,己m 甲基衣己烧專月曰肪族烴類;苯、 兀辰己炫、 烧、氯仿、四氯化破、丨2〜_ 了 = = I本專方香無烴類;二氯曱 烷、四氫呋喃、1,2~二甲氧:二鹵素化烴類;二乙醚、二噚 乙ϋ胺等蕴胺類;乙腈、丙氣二甲基甲_、二甲基 甲基乙基酮等酮類;乙酸乙酉旨、二 '酉允丁:: J基異丁基酉同、環己酮、 氣1,3-二甲基—2l 日相類醇、乙醇等醇 此等溶劑可翔制或將甲基㈣、水等溶劑, 鹼例如,三乙胺、二 鉀等碳酸鹽類;碟酸一奇細飞虱化鹼至屬頌,奴酸虱鈉、碳酸 金屬鹽類;甲_乙醇T等納f,酸鹽類;氫化納等氫化驗 乙基 當量之範圍適之二合可物’於_至5倍莫耳 =氟ΪίΪΐΧ峨、漠化乙烧,化三氟甲烧、破2,2,2 — ;婦等齒化丙稀類、溴化丙賴化丙块 商恤、二甲基硫 耳當示之化合物’於1至5倍莫 $ 〜擇使用,或作為溶劑使用。 心恤又攸一 80c至使用溶劑之回流溫度 '反應時間從數分 58 200836629 鐘至96小時之範圍各自適當選擇即可 製造方法9 R2Τ Τ γ6) ^; (, 47) ' 5R2 'Y2 'Y4 2 ") The compound represented by the formula (45) is used as a starting material, and the "secret, f-making method" can be used to produce the formula (1) or the formula (3). (4) (4) The description of the chest is not complete (3) Basic, (1) 峨, C1, C6 slender 57 200836629 λΛ; 〇 2 % (Χ) π (48) (General formula (48) and general formula (49), (4S> ; Q2 and the above [1] Ά 'α 1 2, 3, A4, X, n, G2, R2, the compound represented by the formula (48) and the solvent 3) 4 South 'nj, 1, (3⁄4 羲. The compound represented by the formula (49). The test "reactant reaction" can be used to produce a compound which hinders the reaction, for example, a m-methyl hexyl burned aquarium hydrocarbon; benzene, 兀辰Hyun, burn, chloroform, tetrachlorinated, 丨2~_ == I This compound has no hydrocarbons; dichlorodecane, tetrahydrofuran, 1,2-dimethoxy: dihalogenated hydrocarbons; diethyl ether , such as acetonitrile, acetonitrile, dimethyl ketone, dimethyl ketone, ketones, acetonitrile, acetonitrile, dimethyl ketone, etc.; Cyclohexanone, gas 1,3-dimethyl-2l, phase alcohol, ethanol, etc. a solvent such as methyl (tetra) or water, a base such as a carbonate such as triethylamine or dipotassium; a dish of a sulphuric acid; a sodium sulphate; a metal carbonate; Iso-f, acid salt; hydrogenation and other hydrogenation test ethyl equivalent range suitable for dimeric can be 'in _ to 5 times mol = fluoride Ϊ ΪΐΧ峨, desertified E-burn, trifluoromethane, broken 2 , 2, 2 —; Women's toothed propylene, brominated propyl sulphate, dimethyl sulphur as a compound shown in '1 to 5 times more than use, or used as a solvent. The compassion is further reduced to 80 ° to the reflux temperature of the solvent. The reaction time is from the range of 58 to 86,366,290 to 96 hours.
(X)n «I 、q2 (22) (50) 5 (通式(22)及通式(50)中,Al、A a、λ v η p 〜、Q2與前述Π]中之 Al、a2、a3、2a A3x A4、X/ n、G2、Rl、 同義。) 2 A3 dn、G2、Rl、R2、Q2 9 —(i):通式(22)—通式(5〇) Ϊ通物於Ϊ射細喊嶋反應,並添加觸 媒於虱㈣圍下反應,能製造通式⑽表示之化合物。 甲其33„礙本反應進行即可例如,己烧、環己烧、 ^ 3 類;苯、f曱笨、甲苯等芳香族烴類;二氯甲 二氣、四鼠石反、1,2-二氯乙燒等_素化烴類;二乙鍵、 ,、四氫料、二甲氧基乙辟嶋;二曱基甲胺、二甲基 ^胺巧麵;乙腈、丙腈等細;丙酉同、甲基異丁基嗣、環己嗣、 ^乙酮,乙酸乙1旨、⑽丁I旨等g旨類;1,3_二甲基—2—味唾 ,酮、環颯烧、二甲基亞石風、曱醇、乙醇等醇類;水等溶劑,此 溶劑可單獨使用或將2種以上混合使用。 、 觸媒,例如鈀一碳、氫氧化把一碳等鈀觸媒類、倫尼鎳等鎳 觸媒類、鈷觸媒類、鉑觸媒類、釕觸媒類、铑觸媒類等。 類例如,甲盤、乙醛、丙醛、三氟乙醛、二氟乙醛、氟乙 给、鼠乙路、一鼠乙、三氯乙盤、漠乙酸等酸類。 酮類例如,丙酮、全氟丙酮、甲乙酮等酮類。 、反應壓力於1氣壓至100氣壓之範圍各適當選擇即可。反應 溫度從一2(TC至使用溶劑之回流溫度、反應時間從數分鐘至96 ^ 時之範圍各自適當選擇即可。 59 200836629 9一(ii):通式(22) 通式(50)(他法丨) ^式(22)表示之化合物於溶劑中,與__類反應 劑處理,可製造通式(50)表示之化合物。 、心亚以逖原 溶劑只要不顯著妨礙本反應進行即可例如, 甲基環己烧等脂肪族烴類;笨、二甲苯、曱I耸 展、元、 烷、氯仿、四氯化碳、i 2— 一 香族烴類;二氯甲 夫喃、1,2-二曱氧基乙烧等_;二甲基甲 _ = 乙酸胺等醯義;乙腈、丙腈等腈_丙酮、甲基里丁基剩、5 土 甲乙酮等酮類;乙酸乙g旨、乙酸丁§旨等轉;i 3」二甲^己,、 唆酮、環石風燒、二甲基亞硬、甲醇、 醇:甲基;咪唾 溶劑可單獨使用或將2 _上混合制耗成水’此等 化物^細如,痛b鈉、錢氰钱、简三乙__氮 乙乙酸,、三氣乙駿、二氟乙搭、敗 。烚乳乙醃、一虱乙[二氯乙醛、溴乙醛等醛類。 酮類,例如,丙酮、全氟丙_、甲乙嗣等酉同類。 ^應溫度從-2(TC至使用溶劑之回流溫度、反 鐘至96小時之範圍各自適當選擇即可。 心' 寸間仗數刀 9「(iii广通式(22)—通式(5〇)(他法幻 化合物於溶劑中或無溶劑,與曱化劑反声, 溶劑只要不縣妨礙本反應進行即為If ^ J基環,肪族烴類;苯、二甲笨、甲以芳(X)n «I , q2 (22) (50) 5 (In the general formula (22) and the general formula (50), Al, a a, λ v η p 〜, Q2 and Al, a2 in the above Π] , a3, 2a A3x A4, X/n, G2, Rl, synonymous.) 2 A3 dn, G2, Rl, R2, Q2 9 - (i): general formula (22) - general formula (5〇) The compound represented by the formula (10) can be produced by a reaction of sputum and a reaction of adding a catalyst to the reaction of 虱(iv). A 33 of it can be subjected to the reaction, for example, hexane, cyclohexane, ^ 3; benzene, f 曱 st, toluene and other aromatic hydrocarbons; dichloromethane, tetrazolla, 1, 2 - Dichloroethane, etc. - sulfonated hydrocarbons; di-ethyl, tetrahydrogen, dimethoxyethane; dimercaptomethylamine, dimethylamine, acetonitrile, propionitrile, etc. ; propyl hydrazine, methyl isobutyl hydrazine, cyclohexyl hydrazine, ethyl ketone, acetic acid, ethyl acetate, (10) butyl I, etc.; 1,3 dimethyl-2, taste, ketone, oxime An alcohol such as dimethyl sulfite, sterol or ethanol; or a solvent such as water. The solvent may be used singly or in combination of two or more. Catalyst, for example, palladium-carbon, hydrogen peroxide, palladium such as carbon Catalysts, nickel catalysts such as Lenny nickel, cobalt catalysts, platinum catalysts, ruthenium catalysts, ruthenium catalysts, etc. Classes such as A plate, acetaldehyde, propionaldehyde, trifluoroacetaldehyde , difluoroacetaldehyde, fluoroethylene, rat B, a mouse B, trichloroethane, desert acetic acid and other acids. Ketones such as acetone, perfluoroacetone, methyl ethyl ketone and other ketones, reaction pressure at 1 atmosphere to The range of 100 air pressure can be appropriately selected. The reaction temperature The degree can be appropriately selected from the range of TC to the reflux temperature of the solvent, and the reaction time is from several minutes to 96 ^ 59. 59 200836629 9 one (ii): general formula (22) general formula (50) (he The compound represented by the formula (22) can be produced by treating the compound represented by the formula (22) with a __-type reactant to produce a compound represented by the formula (50). The heart-like solvent can be used as long as it does not significantly hinder the reaction. For example, aliphatic hydrocarbons such as methylcyclohexane; stupid, xylene, oxime I, aramid, chloroform, carbon tetrachloride, i 2 - an aromatic hydrocarbon; dichloromethyl fumon, 1 , 2-dimethoxyethane, etc. _; dimethylmethyl _ = acetic acid amine, etc.; acetonitrile, propionitrile and other nitrile _ acetone, methyl butyl residue, 5 methane ethyl ketone and other ketones; The purpose is to convert acetic acid to cis; i 3" dimethyl hexanol, fluorenone, cyclarene, dimethyl sulfoxide, methanol, alcohol: methyl; sodium saliva solvent can be used alone or 2 _ Mixed production of water into the 'such as the chemical ^ fine, such as pain b sodium, money cyanide, Jane San Yi __ nitrogen acetic acid, three gas, Jun, difluoroethylene, defeated. B [formaldehyde such as dichloroacetaldehyde or bromoacetaldehyde Ketones, for example, acetone, perfluoropropene, methyl ethyl hydrazine, etc. ^ The temperature should be appropriately selected from -2 (TC to the reflux temperature of the solvent, from the counterclockwise to the 96-hour range. Between the inch and the number of knives 9" (iii wide formula (22) - general formula (5 〇) (the phantom compound in the solvent or no solvent, anti-sounding agent with the sputum, as long as the solvent does not interfere with the reaction, For If ^ J base ring, aliphatic hydrocarbons; benzene, dimethyl stupid, Ai Yifang
i、石炭、n二氯乙燒等自素化烴類;二乙H 乙_麵胺類;乙腈、丙腈等腈類 =土 乙酸丁崎 疋闕、%砜烷、二甲基亞砜、甲醇、土. 十f 溶劑可單獨使用或將2種以上混Ϊ使广4_;水德劑,此等 60 200836629 甲醯基化劑,例如,曱酸、甲酸、氟曱酸、曱醯基(2,2—二曱 基丙酸)等曱酸酐類;曱酸苯酯等甲酸酯類;五氟苯曱醛 、口号口坐等。 γ γ添加劑例如,硫酸等無機酸、甲酸等有機酸、硼氫化鈉、硼 氫氰化鈉等硼氰化物類、硼酸、氫化鐘銘等。 反應溫度從一20。(:至使用溶劑之回流溫度、反應時間從數八 鐘至96小時之範圍適當選擇即可。 刀 製造方法10i, charcoal, n-dichloroethane and other self-acidified hydrocarbons; diethyl H-ethylamine; nitrile such as acetonitrile, propionitrile = acesulfame, sulfone, dimethyl sulfoxide, Methanol, earth. Ten f solvent can be used alone or in combination of two or more kinds of water; a hydrophile, such 60 200836629 a mercapto grouping agent, for example, citric acid, formic acid, fluoroantimonic acid, sulfhydryl ( 2,2-dimercaptopropionic acid and other phthalic anhydrides; formic acid esters such as phenyl phthalate; pentafluorobenzaldehyde, slogan, etc. The γ γ additive is, for example, an inorganic acid such as sulfuric acid, an organic acid such as formic acid, a boron cyanide such as sodium borohydride or sodium borohydride, boric acid or hydrogenated bell. The reaction temperature is from one to twenty. (: It is sufficient to use the reflux temperature of the solvent and the reaction time from the range of several to eight hours to 96 hours.
(53) (通式(22)、通式(25)、通式(S1)、通式及通式(53)中, A2、A3、A4、G2、Ri、R2、X、n、(^、q2與前述⑴中之 Ai y A3、A4、G2、R!、R2、x、n、(^、q2 同義,Hal 表示鹵素 2、 10 — (i):通式(22) +通式(51)~>通式(52) 、 °) 依照Tetrahedron Letters ρ·3789(1999)等記載之公知條件 (22)表示之化合物與通式(51)表示之化合物反應,可製造通通式 表示之化合物。溶劑、反應溫度等條件,不限於文獻記戴|(52) 10 —⑼:通式(52) +通式(25)—通式(53) σ 考。 將通式(52)表示之化合物與通式(25)表示之化合物,依照欺、,、 (iv)記載之條件反應,可製造通式(53)表示之化合物。〜別攻1〜 製造方法11(53) (in the general formula (22), the general formula (25), the general formula (S1), the general formula and the general formula (53), A2, A3, A4, G2, Ri, R2, X, n, (^ And q2 are synonymous with Ai y A3, A4, G2, R!, R2, x, n, (^, q2 in the above (1), Hal represents halogen 2, 10 - (i): general formula (22) + general formula ( 51)->General formula (52), °) A compound represented by the known condition (22) described in Tetrahedron Letters ρ·3789 (1999) or the like is reacted with a compound represented by the formula (51) to produce a general formula. Conditions such as a solvent, a reaction temperature, and the like are not limited to those in the literature. (52) 10 - (9): Formula (52) + Formula (25) - Formula (53) σ. The formula (52) is represented. The compound represented by the formula (25) can be produced by reacting the compound with the compound represented by the formula (25) according to the conditions described in (iv).
(通式(20)、通式(54)、通式(55)及通式(56)中,&、a A4、G2、Ri、R2、X、n、Qi、(¾ 與前述[1]中之 a、a、a 八3、 1 2、A3、A4、 61 200836629 G2、、r2、X、η、Qi、Q2同義,Hal表示鹵素原子。) U —(i):通式(54)—通式(55) ^ 將通式(54)表示之化合物,依照前述2 — 記載之條件反應,可製 ^ 造通式(55)表示之化合物。 η — © :通式(55) +通式(20)->通式(56) - 將通式(55)表示之化合物與通式(2〇)表示之化合物,依照前述1 一 (1)記载之條件反應,可製造通式(56)表示之化合物。 11 —(iii):通式(54) +通式(20)—通式(56) 將通式(54)表示之化合物,依照前述1 一①記載之使用縮合劑之條 _ 件或使用混合酸酐法之條件,與通式(20)表示之化合物反應,可製 造通式(56)表示之化合物。 /七述所不全部之製造方法中,目的物可於反應結束後從反應 =2單離即可,視需要可進行再結晶、管柱層析、蒸潑等操 ^精衣。又’可不從反應系將目的物單離,而供其次之反應步 之=顯(In the general formula (20), the general formula (54), the general formula (55), and the general formula (56), &, a A4, G2, Ri, R2, X, n, Qi, (3⁄4 and the above [1] a, a, a 八 3, 1 2, A3, A4, 61 200836629 G2, r2, X, η, Qi, Q2 are synonymous, Hal represents a halogen atom.) U — (i): general formula (54 - General formula (55) ^ The compound represented by the formula (54) can be produced according to the conditions described in the above 2-(2). η - © : Formula (55) + General formula (20)-> General formula (56) - A compound represented by the formula (55) and a compound represented by the formula (2) can be produced by reacting according to the conditions described in the above (1). a compound represented by the formula (56): 11 - (iii): a compound represented by the formula (54) + a formula (20) - a compound represented by the formula (54), which is condensed according to the above 1-1 The compound of the formula (56) can be produced by reacting the compound with the compound represented by the formula (20) under the conditions of the mixed acid anhydride method, and the compound represented by the formula (56) can be produced. After the reaction is completed, it can be separated from the reaction = 2, and if necessary, recrystallization, column chromatography, and steaming can be carried out. ^ Fine coating operation. And 'the desired product may not be isolated from the reaction system, and secondly for the reaction steps explicitly =
Bu」表示第二丁基、rt—B # 一 氫原子、「〇」表示氧原子、「S」表示「H」表示 N」表示氮原子、「F」表示氟原子、「=子、一C」表示碳原子 基、「s —Bu ·矣士筮-丁I、Ώ 、土1 Bu」表示異丁Bu" represents a second butyl group, rt-B #-hydrogen atom, "〇" means an oxygen atom, "S" means "H" means N" means a nitrogen atom, "F" means a fluorine atom, "= sub, a C" "carbon atom base, "s-Bu · gentleman 筮 - D, I, 1 1 Bu" means
Cl」表示氯原子、 氟甲基Cl" means chlorine atom, fluoromethyl group
Br」表 示溴原子、「I」表示碘原子、「CF3 ,表一 通式(A) ^Br represents a bromine atom, "I" represents an iodine atom, "CF3, Table 1 (A) ^
62 200836629 表1⑴ 化合物 編號 Qi a,2 A,3 A,4 Ri r2 〇2 1-1 苯基 CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-2 2-甲基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-3 3-甲基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-4 4-甲基苯基 CH CH CH CH H H 2,4-二溴各三氟甲基硫苯基 1-5 2-乙基苯基 CH CH CH CH H H 2,4-二廣-6-二氣甲基硫苯基 1-6 3-乙基苯基 CH CH CH CH H H 2,4-二>臭-6-二象甲基硫苯基 1-7 4-乙基苯基 CH CH CH CH H H 2,4-二、/臭-6-二敗甲基硫苯基 1-8 2-氟苯基 CH CH CH CH H H 2,4-二>臭-6-二敦甲基硫苯基 1-9 3-氟苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-10 4-氣苯基 CH CH CH CH H H 2,4-二>臭-6-二敦甲基硫苯基 1-11 2-氯苯基 CH CH CH CH H H 2,4-二>臭-6-二鼠曱基硫苯基 1-12 3-氯苯基 CH CH CH CH H H 2,4-二漠-6-二象甲基疏苯基 M3 4-氯苯基 CH CH CH CH H H 2,4-二溴-6·三氟甲基硫苯基 1-14 2-溴苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-15 3-溴苯基 CH CH CH CH H H 2,4-二>臭-6-二亂甲基硫苯基 1-16 4-溴苯基 CH CH CH CH H H 2,4-二 >臭-6-二亂曱基硫苯基 1-17 2-埃苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-18 3-蛾未基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-19 4-埃笨基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-20 3-氰基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基硫苯基 63 200836629 表 1(2) 化—合物 編號 Qi a,2 a,3 A,4 Ri r2 q2 1-21 4-氰基苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-22 2-硝基苯基 CH CH CH CH H H 2,4-二溴各三氟甲基硫苯基 1-23 3-頌基苯基 CH CH CH CH H H 2,4-二>臭-6-二氟甲基硫苯基 1-24 4-破基苯基 CH CH CH CH H H 2,4-二>臭-6-二亂甲基硫苯基 1-25 2-胺基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-26 3-胺基苯基 CH CH CH CH H H 2,4-二>臭-6-二鼠甲基硫苯基 1-27 4-胺基苯基 CH CH CH CH H H 2,4-二>臭-6-二默甲基硫苯基 1-28 2-三氟甲基苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-29 3-三氟曱基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-30 4-三氟甲基苯基 CH CH CH CH Π H 2,4-二 >臭-6-二亂甲基硫苯基 1-31 2-羥基苯基 CH CH CH CH H H 2,4-二漠-6-二氟甲基硫苯基 1-32 2-甲氧基苯基 CH CH CH CH H H 2,4-二〉臭-6-二氣曱基硫苯基 1-33 3-甲氧基苯基 CH CH CH CH H H 2,4-二 >臭-6-二敗甲基硫苯基 1-34 4-甲氧基苯基 CH CH CH CH H H 2,4-二>臭-6·二氣甲基硫苯基 1-35 2-苯氧基苯基 CH CH CH CH H H 2,4-二>臭-6-二氟甲基硫苯基 1-36 4-(1,1-二甲基乙基) 苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-37 3-(二甲基胺基苯 基) CH CH CH CH H H 2,4-二溴-6·三氟曱基硫苯基 1-38 4-(二甲基胺基苯 基) CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-39 4-三氟甲氧基苯基 CH CH CH CH H H 2,4-二>臭**6-二氣甲基硫苯基 1-40 2-(乙酿基胺基) 苯基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基硫苯基 64 200836629 表 1(3) it合物 編號 Qi Α5ι a,2 A,3 A,4 Ri r2 Q2 1 - 41 : 乙醯基胺基)苯基 CH CH CH CH H H : 2,4-二溴-6-三氟曱基硫苯基 1-42 4-(乙醯基胺基)苯基 CH CH CH CH H H : 2,4-二溴-6-三氟甲基硫苯基 1-43 2-乙醯氧苯基 CH CH CH CH H H : 2,4-二溴-6-三氟甲基硫苯基 1-44 2-(甲氧羰基)苯基 CH CH CH CH H H 2,4-二>臭-6-二敗甲基硫苯基 1-45 4-(曱氧羰基)苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-46 2,3-二曱基苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-47 2,4-二甲基苯基 CH CH CH CH H H 2,4-二漠-6-二氟甲基硫苯基 1-48 2,6-二甲基苯基 CH CH CH CH H H 2,4-二溴·6-三氟曱基硫苯基 1-49 2,3-二1苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-50 2,4-二氣苯基 CH CH CH CH H H 2,4-二溴各三氟甲基硫苯基 1-51 2,5-二氟苯基 CH CH CH CH H H 2,4-二溴各三氟甲基硫苯基 1-52 2,6-二默苯基 CH CH CH CH H H 2,4-二溴各三氟甲基硫苯基 1-53 3,4-二氟苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-54 3,5-二氣苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-55 2,3-二氯苯基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基硫苯基 1-56 2,4-二氯苯基 CH CH CH CH H 2,4-二>吴-6-二氣曱基硫苯基 1-57 2,5-二氯苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-58 2,6-二氣本基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-59 3,4-二氯苯基 CH CH CH CH H H 2,4-二〉臭-6-二篆曱基硫苯基 1-60 2,4-二硝基苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 65 200836629 表 1(4) 化合物 編號 Qi A、 a,2 a,3 A,4 Ri r2 q2 1-61 3,4-二硝'基苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-62 2,6-二甲氧基苯基 CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-63 3,5-二甲氧基苯基 CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-64 3-甲基-4-硝基苯基 CH CH CH CH H H 2,4-二>臭-6-二說曱基硫苯基 1-65 5-胺基-2-氣苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基琉苯基 1-66 3-氟-2-甲基苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-67 2-氣-5-确基苯基 CH CH CH CH H H 2,4-二>臭-6-二亂甲基硫苯基 1-68 4-氣-3-頌基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-69 5-氣-2-石肖基苯基 CH CH CH CH H H 2,4-二漠-6-二氣甲基硫苯基 1-70 2-氣-6-填苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-71 2-1-5-二氣曱基苯 基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-72 2-氯-4-頌基苯基 CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-73 2-氯-4-氣苯基 CH CH CH CH H H 2,4-二溴各三氟甲基硫苯基 1-74 2-氯-6-氣苯基 CH CH CH CH H H 2,4-二>臭-6-三敗曱基硫苯基 1-75 3-氯-4-1苯基 CH CH CH CH H H 2,4-二 >臭-6-二氣甲巷硫苯泰 1-76 4-氯-2-氣苯基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基疏苯基 1-77 4-氣-2-頌基本基 CH CH CH CH H H 2,4-二>臭-6-二鼠曱基硫苯基 1-78 3-甲氧基4-硝基苯 基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-79 2-甲氧基-4-确基苯 基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-80 2,3,4-三氟苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 66 200836629 表 1(5)62 200836629 Table 1(1) Compound number Qi a,2 A,3 A,4 Ri r2 〇2 1-1 Phenyl CH CH CH CH HH 2,4-Dibromo-6-trifluoromethylthiophenyl 1-2 2 -Methylphenyl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-3 3-methylphenyl CH CH CH CH HH 2,4-di> -6-dimethylthiophenyl 1-4 4-methylphenyl CH CH CH HH 2,4-dibromo-trifluoromethylsulfophenyl 1-5 2-ethylphenyl CH CH CH CH HH 2,4-二广-6-di-gasmethylthiophenyl 1-6 3-ethylphenyl CH CH CH H H 2,4-di> odor-6-di-m-methylthiophenyl 1-7 4-ethylphenyl CH CH CH CH HH 2,4-di,/odor 6-dioxomethylthiophenyl 1-8 2-fluorophenyl CH CH CH HH 2,4-di >Smelly-6-di-denylmethylthiophenyl 1-9 3-fluorophenyl CH CH CH HH 2,4-di>Smell-6-dimethylthiophenyl 1-10 4-gas Phenyl CH CH CH CH HH 2,4-di>Smell-6-didonylmethylthiophenyl 1-11 2-chlorophenyl CH CH CH CH HH 2,4-di>Smell-6-II Murine thiophenyl 1-12 3-chlorophenyl CH CH CH CH HH 2,4-di- -6-di-m-methylphenylphenyl M3 4-chlorophenyl CH CH CH H H 2,4- Dibromo-6·trifluoromethylthiobenzene 1-14 2-Bromophenyl CH CH CH CH HH 2,4-di>Smell-6-dimethylthiophenyl 1-15 3-bromophenyl CH CH CH CH HH 2,4-di> Odor-6-disintegrated methylthiophenyl 1-16 4-bromophenyl CH CH CH CH HH 2,4-di>Smell-6-disindolylthiophenyl 1-17 2-Ethylene CH CH CH CH HH 2,4-Dibromo-6-trifluoromethylthiophenyl 1-18 3-Mothyl CH CH CH CH HH 2,4-Dibromo-6-trifluoromethylthiobenzene Base 1-19 4-Ethyl CH CH CH CH HH 2,4-di>Smell-6-dimethylthiophenyl 1-20 3-cyanophenyl CH CH CH HH 2,4- II>Smell-6-di-mercaptothiophenyl 63 200836629 Table 1(2) Compound number Qi a,2 a,3 A,4 Ri r2 q2 1-21 4-cyanophenyl CH CH CH CH HH 2,4-dibromo-6-trifluoromethylthiophenyl 1-22 2-nitrophenyl CH CH CH HH 2,4-dibromo-trifluoromethylthiophenyl 1-23 3-mercaptophenyl CH CH CH CH HH 2,4-di>odor-6-difluoromethylthiophenyl 1-24 4-pyridylphenyl CH CH CH HH 2,4-di> Odor-6-disorder methylthiophenyl 1-25 2-aminophenyl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-26 3-amino Phenyl CH CH CH CH HH 2,4-di & Gt-6-dimethylthiophenyl 1-27 4-aminophenyl CH CH CH H H 2,4-di>odor-6-dimermethylthiophenyl 1-28 2- Trifluoromethylphenyl CH CH CH H H 2 2,4-dibromo-6-trifluoromethylthiophenyl 1-29 3-trifluorodecylphenyl CH CH CH CH HH 2,4-di> Odor-6-dimethylthiophenyl 1-30 4-trifluoromethylphenyl CH CH CH CH Π H 2,4-di > odor-6-disorder methylthiophenyl 1-31 2 -hydroxyphenyl CH CH CH H H 2,4-di--6-difluoromethylthiophenyl 1-32 2-methoxyphenyl CH CH CH CH HH 2,4-di>odor-6- Di-mercaptothiophenyl 1-33 3-methoxyphenyl CH CH CH CH HH 2,4-di >odor-6-dioxomethylthiophenyl 1-34 4-methoxyphenyl CH CH CH CH HH 2,4-di>Smelly-6·dimethylthiophenyl 1-35 2-phenoxyphenyl CH CH CH H H 2 2,4-di>Smell-6-II Fluoromethylthiophenyl 1-36 4-(1,1-dimethylethyl)phenyl CH CH CH HH 2,4-dibromo-6-trifluoromethylsulfophenyl 1-37 3- (Dimethylaminophenyl) CH CH CH CH HH 2,4-Dibromo-6·trifluorodecylthiophenyl 1-38 4-(dimethylaminophenyl) CH CH CH CH HH 2 ,4-dibromo-6-trifluorodecylthiophenyl 1-39 4-Trifluoromethoxyphenyl CH CH CH CH HH 2,4-di>Smell **6-Dimethylthiophenyl 1-40 2-(Ethylamino)phenyl CH CH CH CH HH 2,4-di>Smell-6-di-mercaptothiophenyl 64 200836629 Table 1 (3) It Compound No. Qi Α5ι a,2 A,3 A,4 Ri r2 Q2 1 - 41 : Ethylamino)phenyl CH CH CH H H : 2,4-dibromo-6-trifluoromethylthiophenyl 1-42 4-(ethinylamino)phenyl CH CH CH CH HH : 2,4-dibromo-6-trifluoromethylthiophenyl 1-43 2-acetoxyphenyl CH CH CH H H : 2,4-dibromo-6-trifluoromethylthiophenyl 1-44 2-(methoxycarbonyl)phenyl CH CH CH H H 2,4-di>odor-6-dioxomethylthiophenyl 1-45 4-(indolylcarbonyl)phenyl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-46 2,3-dimercaptophenyl CH CH CH CH HH 2,4-dibromo-6-trifluoromethyl Thiophenyl 1-47 2,4-dimethylphenyl CH CH CH HH 2,4-di--6-difluoromethylthiophenyl 1-48 2,6-dimethylphenyl CH CH CH CH HH 2,4-dibromo-6-trifluorodecylthiophenyl 1-49 2,3-diphenylphenyl CH CH CH H 2,4-di>odor-6-dimethylmethyl Thiophenyl 1-50 2,4-diphenyl CH CH CH CH HH 2,4-Dibromotrifluoromethylsulfophenyl 1-51 2,5-difluorophenyl CH CH CH CH HH 2,4-dibromotrifluoromethylthiophenyl 1 -52 2,6-dimerylphenyl CH CH CH HH 2,4-dibromotrifluoromethylsulfophenyl 1-53 3,4-difluorophenyl CH CH CH HH 2,4-di >Smelly-6-dimethylthiophenyl 1-54 3,5-diphenylphenyl CH CH CH H H 2,4-di>Smell-6-dimethylthiophenyl 1-55 2,3-dichlorophenyl CH CH CH CH HH 2,4-di>odor-6-di-mercaptothiophenyl 1-56 2,4-dichlorophenyl CH CH CH CH 2,4 -二> Wu-6-di-mercaptothiophenyl 1-57 2,5-dichlorophenyl CH CH CH H H 2 2,4-dibromo-6-trifluoromethylthiophenyl 1-58 2,6-digas base CH CH CH CH HH 2,4-dibromo-6-trifluoromethylthiophenyl 1-59 3,4-dichlorophenyl CH CH CH HH 2,4-di 〉 odor-6-dimercaptothiophenyl 1-60 2,4-dinitrophenyl CH CH CH H H 2,4-dibromo-6-trifluoromethylthiophenyl 65 200836629 Table 1 ( 4) Compound number Qi A, a, 2 a, 3 A, 4 Ri r2 q2 1-61 3,4-dinitro-phenylphenyl CH CH CH HH 2,4-dibromo-6-trifluoromethyl Thiophenyl 1-62 2,6-dimethoxyphenyl CH CH C H CH HH 2,4-dibromo-6-trifluorodecylthiophenyl 1-63 3,5-dimethoxyphenyl CH CH CH CH HH 2,4-dibromo-6-trifluorodecyl Thiophenyl 1-64 3-methyl-4-nitrophenyl CH CH CH H H 2 2,4-di> odor-6-di-decylthiophenyl 1-65 5-amino-2- Gas phenyl CH CH CH CH HH 2,4-di > odor-6-dimethylhydrazine phenyl 1-66 3-fluoro-2-methylphenyl CH CH CH H H 2,4-dibromo -6-trifluoromethylsulfophenyl 1-phenyl 2-gas-5-decylphenyl CH CH CH CH HH 2,4-di > odor-6-disorder methylthiophenyl 1-68 4 - gas-3-mercaptophenyl CH CH CH CH HH 2,4-di>Smell-6-dimethylthiophenyl 1-69 5-Gas-2-Gentocylphenyl CH CH CH H H 2 ,4-二漠-6-二气methylthiophenyl 1-70 2-gas-6-filled phenyl CH CH CH CH HH 2,4-di> odor-6-dimethylthiophenyl 1-71 2-1-5-Dimethyl nonylphenyl CH CH CH CH HH 2,4-Dibromo-6-trifluoromethylthiophenyl 1-72 2-chloro-4-indolylphenyl CH CH CH CH HH 2,4-dibromo-6-trifluorodecylthiophenyl 1-73 2-chloro-4-phenylphenyl CH CH CH CH HH 2,4-dibromo-trifluoromethylthiobenzene 1-74 2-Chloro-6-gas phenyl CH CH CH CH HH 2,4-di>Smell-6-trisole Phenyl 1-75 3-chloro-4-1 phenyl CH CH CH CH HH 2,4-di> odor-6-two gas thiophene 1-76 4-chloro-2-phenyl phenyl CH CH CH CH HH 2,4-di>Smell-6-dihalohydrazinophenyl 1-77 4-Ga-2-indole basic CH CH CH CH HH 2,4-di>Smell-6- Dimethyl thiophenyl 1-78 3-methoxy 4-nitrophenyl CH CH CH H H 2,4-dibromo-6-trifluoromethylthiophenyl 1-79 2-methoxy 4--4-phenylphenyl CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-80 2,3,4-trifluorophenyl CH CH CH HH 2, 4-II>Smell-6-dimethylthiophenyl 66 200836629 Table 1(5)
化合物 編號 Qi Α、 α,2 A,3 A,4 Ri r2 q2 1-81 2,4,6-三甲基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-82 2J,6-三氟苯基 CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-83 2,4,5-三甲氧基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基硫苯基 1-84 3,4,5-三曱氧基苯基 CH CH CH CH H H 2,4-二>臭-6-三敗甲基硫苯基 1-85 2,3,4,5,6-五氟苯基 CH CH CH CH H H 2,4-二>臭-6-二氟甲基硫苯基 1-86 2-聯苯 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-87 3-聯苯 CH CH CH CH H H 2,4-二>臭-6-二氟甲基硫苯基 1-88 1-奈基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基硫苯基 1-89 2-萘基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基硫苯基 1-90 ^比17定-2-基 CH CH CH CH H H 2,4-二、/臭-6-二氣曱基硫苯基 1-91 °比°定-3-基 CH CH CH CH H H 2,4-二>臭-6-二氟甲基硫苯基 1-92 吼。定-4-基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基硫苯基 1-93 2-甲基吼咬-5-基 CH CH CH CH H H 2,4-二浪-6-二氣曱基硫苯基 1-94 3-甲基吡啶-2-基 CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-95 2-氣吼唆·^-基 CH CH CH CH H H 2,4-二>臭-6-二氟甲基硫苯基 1-96 2·氣11比唆-3-基 CH CH CH CH H H 2,4-二>臭-6-二鼠甲基硫笨基 1-97 2-氯定-4-基 CH CH CH CH H H 2,4-二>臭-6-二亂甲基硫苯基 1-98 二-氣吼17定-6-基 CH CH :CH CH :H H 2,4-二>臭-6-二氣曱基硫苯基 1-99 2-氣 基 CH CH [CH CH :H H 2,4-二 >臭-6-二氣甲基硫苯基 1-100 5-鼠°比°定-2-基 CH CH [CH CH :H H 2,4-二>臭-6-二氣甲基硫苯基 67 200836629 表 1(6)Compound number Qi Α, α, 2 A, 3 A, 4 Ri r2 q2 1-81 2,4,6-trimethylphenyl CH CH CH HH 2,4-di>Smell-6-two gas Thiophenyl 1-82 2J,6-trifluorophenyl CH CH CH HH 2,4-dibromo-6-trifluorodecylthiophenyl 1-83 2,4,5-trimethoxyphenyl CH CH CH CH HH 2,4-di>Smell-6-di-mercaptothiophenyl 1-84 3,4,5-trimethoxyphenyl CH CH CH CH HH 2,4-di> Odor-6-tris-methylthiophenyl 1-85 2,3,4,5,6-pentafluorophenyl CH CH CH HH 2,4-di>odor-6-difluoromethylthiobenzene 1-86 2-biphenyl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-87 3-biphenyl CH CH CH CH HH 2,4-di> Odor-6-difluoromethylthiophenyl 1-88 1-nyl CH CH CH CH HH 2,4-di>odor-6-di-mercaptothiophenyl 1-89 2-naphthyl CH CH CH CH HH 2,4-di>Smell-6-di-mercaptothiophenyl 1-90 ^ ratio 17-but-2-yl CH CH CH CH HH 2,4-di,/odor-6-diox Mercaptothiophenyl 1-91 ° ratio -3--3-CH CH CH CH HH 2,4-di > odor-6-difluoromethylthiophenyl 1-92 oxime.定-4-yl CH CH CH CH HH 2,4-di>Smell-6-di-mercaptothiophenyl 1-93 2-methylindole-5-yl CH CH CH CH HH 2,4-二浪-6-二气曱 thiophenyl 1-94 3-methylpyridin-2-yl CH CH CH H H 2,4-dibromo-6-trifluorodecylthiophenyl 1-95 2- Gas 吼唆·^-based CH CH CH CH HH 2,4-di> odor-6-difluoromethylthiophenyl 1-96 2·gas 11 is more than 唆-3-yl CH CH CH CH HH 2, 4-II>Smell-6-di-methylmethylthiophenyl 1-97 2-Chloridine-4-yl CH CH CH CH HH 2,4-di>Smell-6-disorder methylthiophenyl 1-98 Di-gas 吼17 定-6-yl CH CH :CH CH :HH 2,4-di>odor-6-di-mercaptothiophenyl 1-99 2-gas-based CH CH [CH CH :HH 2,4-di>Smell-6-dimethylthiophenyl 1-100 5-molar ratio °-2-yl CH CH [CH CH :HH 2,4-di > odor - 6-dimethylthiophenyl 67 200836629 Table 1 (6)
化合物 編號 Qi Α、 α,2 A,3 A,4: RiJ Q2 1-101 4-三氟曱基吡啶各基 CH CH CH < CH H H: 2,4-二>臭-6-二氣甲基硫苯基 1-102 3 - 基^比。定-2 -基 CH CH CH丨 CH H H: 2,4-二溴-6-三氟甲基硫苯基 1-103 2-苯氧基吼啶-3-基 CH CH CH CH H H: 2,4-二>臭-6-二氣曱基硫苯基 1-104 2-甲基硫°比唆-3-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-105 2,6-二甲氧基吼啶-3-基 CH CH CH CH H H 2,4-二〉臭-6-二敗曱基硫苯基 1-106 2,3-二氣σ比u定-5-基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-107 2,5-二氣11比°定-3-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-108 2,6-二氣°比。定-3-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫笨基 1-109 3,5-二氣^比唆-斗-基 CH CH CH CH H H 2,4-二>臭-6-二敗曱基硫苯基 1-110 口比咬-^^-乳化^-基 CH CH CH CH H H 2,4-二漠-6-二氣甲基硫苯基 1-111 N-曱基吡咯-2-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-112 口比呼-2-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-113 2-曱基0比。井-5-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-114 4-二氟甲基σ密淀-5-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-115 11 夫喃-2-基 CH CH CH CH H H 二:^-二漠^^-二象曱基疏苯基 1-116 吱喃-3-基 CH CH CH CH H H 2,4-二>臭-6-二1甲基硫苯基 1-117 2-四氳呋喃基 CH CH CH CH :H H 2,4-二>臭-6-二鼠曱基硫苯基 1-118 3-四氳吱喃基 CH CH CH CE :H H 2,4-二>臭-6-二氣甲基硫苯基 1-119 苯并咬喃-2-基 CH CH CH CH [H H 2,4-二>臭-6-二氣甲基硫苯基 1-120 四氫1喃-2-基 CH CH CH CH [H H 2,4-二溴-6-三氟曱基硫苯基 68 200836629 表 1(7) 化合物 編號 Qi Α、 α,2 A,3 A,4 Ri r2 Q2 1-121 2-甲基-5,6·二氫-4H-ϋ瓜喃-3-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-122 σ塞吩-2-基 CH CH CH CH H H 2,4-二>臭-6·二鼠曱基硫苯基 1-123 嗟口分-3-基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基硫苯基 1-124 3-甲基噻吩-2·基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-125 2-梢基σ塞吩-4-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-126 2-甲基σ塞吩-5-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-127 3-氯噻吩-2-基 CH CH CH CH H H 2,4-二〉臭-6-二氣曱基硫苯基 M28 2-氯σ塞吩-5-基 CH CH CH CH H H 2,4-二漠-6-三氟甲基硫苯基 1-129 3 - >臭嗟吩-2-基 CH CH CH CH H H 2,4-二>臭-6-二說甲基硫苯基 1-130 2-溴嗟吩-5-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-131 3 -破^塞吩-2-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-132 3-苯基噻吩-2-基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-133 2,4-二甲基ϋ塞吩-5-基 CH CH CH CH H H 2,4-二>臭-6-二氟1甲基硫苯基 1-134 苯并σ塞吩-2-基 CH CH CH CH H H 2,4-二>臭-6-二亂甲基硫苯基 1-135 4-硝基-1Η吡咯-2-基 CH CH CH CH H H 2,4-二漠-6-二氣甲基硫苯基 1-136 3-乙基-3Η吡唑-4-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-137 1-甲基-3-硝基-1Η-。比嗤-4-基 CH CH CH CH H H 2,4-二、/臭-6-二氣甲基硫苯基 1-138 3-氯-1-曱基-1Η-吡 唑-4-基 CH CH CH CH H H 2,4-二>臭-6-三氟甲基硫苯基 1-139 3-溴小甲基-1Η-吡 唑-4-基 CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-140 1-甲基-3-氟甲基 -1Η- °比嗤-4-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 69 200836629 表 1(8) 化舍物 編號 Qi A5! a,2 A,3 A,4 Ri r2 q2 1-141 1-甲基-5-三氟甲基-1H-π比tr坐-4-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-142 異噚唑-5-基 CH CH CH CH H H 2,4·二溴各三氟曱基硫苯基 1-143 4-三氟曱基噻唑-5-基 CH CH CH CH H H 2,4-二溴-6-三氟曱基硫苯基 1-144 2,4-二曱基噻唑-5-基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1445 2-乙基-4-甲基噻唑-5-基 CH CH CH CH H H 2,4-二>臭-6-二氟甲基硫苯基 1-146 2-氯-4-甲基噻唑-5-基 CH CH CH CH H H 2,4-二溴三氟甲基硫苯基 1-147 3-甲基-異噻唑-5-基 CH CH CH CH H H 2,4-二>臭-6-二說甲基硫苯基 1-148 3,4-二氯-異噻唑-5-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-149 3-氯苯并噻唑-2-基 CH CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-150 2,2-二 1 苯并[1.3]二噚 唑-5-基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-151 2,2-二就-苯并[1.3]二噚 唑_4—基 CH CH CH CH H H 2,4-二>臭-6-二亂甲基硫本基 1-152 苯基 CF CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1-153 2-氣苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-154 4-氟苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-155 4-氯苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基硫苯基 1-156 2_鼠吼咬-3-基 CF CH CH CH H H 2,4-二溴-6-三氟甲基硫苯基 1457 4-硝基苯基 CF CH CH CH H H 2,4·二溴_6_三氟甲基硫苯基 1-158 4-氰基苯基 CF CH CH :CH H H 2,4-二>臭-6-二氣曱基硫苯基 1-159 苯基 CH CH :CH ;CE Me )H 2,4-二>臭-6-二氣曱基硫苯基 1-160 2-亂苯基 CH :CE [CH [CH ;Mc ^ H 2,4-二溴-6-三氟曱基硫苯基 70 200836629 表i⑼ 化合物 編號 Qi α,2 A,3 A,4 Ri r2 Q2 1-161 4-氟苯基 CH CH CH CH Me H 2,4-二溴各三氟甲基硫苯基 1-162 4-氯苯基 CH CH CH CH Me H 2,4-二>臭-6-二說甲基琉苯基 1-163 2-氣。比唆-3-基 CH CH CH CH Me H 2,4-二溴各三氟甲基硫苯基 1-164 4-硝基苯基 CH CH CH CH Me H 2,4-二溴-6-三氟甲基硫苯基 1-165 4-氰基苯基 CH CH CH CH Me H 2,4-二溴-6-三氟甲基硫苯基 1-166 苯基 CH CH CH CH H Me 2,4-二溴-6-二氟甲基硫苯基 ί-167 2-說苯基 CH CH CH CH H Me 2,4-二溴-6-三氟甲基硫苯基 1-168 4-就苯基 CH CH CH CH H Me 2,4-二溴-6-三敗甲基硫苯基 1-169 4-氯苯基 CH CH CH CH H Me 2,4-二溴-6-三氟甲基硫苯基 1-170 2-氯π比咬-3-基 CH CH CH CH H Me 2,4-二溴-6-三氟甲基硫苯基 1-171 4-硝基苯基 CH CH CH CH H Me 2,4_二>臭-6-三氟甲基硫苯基 1-172 4-氰基苯基 CH CH CH CH H Me 2,4-二溴-6-三氟甲基硫苯基 1-173 苯基 CH CH CH CH Me Me 2,4-二溴-6-三氟甲基硫苯基 1-174 2-氟苯基 CH CH GH CH Me Me 2,4-二>臭-6-二亂甲基硫苯基 1-175 4-敗苯基 CH CH CH CH Me Me 2,4-二溴各三氟甲基硫苯基 1-176 4-氯苯基 CH CH CH CH Me Me 2,4-二>吴-6-二氣甲基石瓦苯基 1-177 2-氣吼咬-!^-基 CH CH CH CH Me Me 2,4-二>臭-6-二氣甲基硫苯基 1-178 4-墙基苯基 CH CH CH CH Me Me 2,4-二 >臭-6-二氣甲基硫苯基 1-179 4-氰基苯基 CH CH CH CH Me Me 2,4_二>臭-6-二氟甲基硫苯基 1-180 苯基 CF CH CH CH H H 2,4-二溴-6-三氟甲基亞磺醯基 1 苯基 71 200836629 表 1(10) 化合物 編號 Qi A5! a,2 a,3 A,4 Ri r2 Q2 1-181 2-氣苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基亞石黃酿基苯基 1-182 4-氟苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基亞石黃酿基苯基 1-183 4-氯苯基 CF CH CH CH H H 2,4-二》臭-6-二氟i甲基亞石黃酿基苯基 1-184 2-氯吡啶-3-基 CF CH CH CH H H 2,4-二溴-6-三氟甲基亞磺醯基苯基 1-185 4-硝基苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基亞石黃酿基苯基 1-186 4-氮基苯基 CF CH CH CH H H 2,4-二>臭-6-三氣曱基亞石黃酸基苯基 1-187 笨基 CH CH CH CH Me H 2,4-二>臭-6-二氣甲基亞石黃酿基苯基 1-188 2-敗苯基 CH CH CH CH Me H 2,4-二>臭-6-二氣曱基亞石黃酿基苯基 M89 苯基 CH CH CH CH Me H 2,4-二>臭-6-二氣甲基亞石黃酿基苯基 1-190 4-氯苯基 CH CH CH CH Me H 2,4-二>臭-6-二氣甲基亞石黃酸基苯基 1-191 2-氯吡啶-3-基 CH CH CH CH Me H 2,4-二>臭-6-二氣甲基亞石黃酿基苯基 1-192 4-硝基苯基 CH CH CH CH Me H 2,4_二溴·6-三氟甲基亞磺醯基苯基 1:193 4-氰基苯基 CH CH CH CH Me H 2,4-二>臭-6-二鼠甲.基亞績酿基苯基 1-194 苯基 CH CH CH CH H Me 2,4-二溴-6-三氟甲基亞磺醯基苯基 1-195 2-氟苯基 CH CH CH CH H Me 2,4-二>臭-6-二鼠甲基亞石黃蕴基苯基 1-196 4-氟苯基 CH CH CH CH H Me 2,4-二>臭-〇-二亂甲基亞績酸泰本基 1-197 4-氯苯基 CH CH CH CH H Me ,2,4-二>臭-$-二鼠曱基亞石黃酿基苯基 1-198 2-鼠0比。定-3-基 CH CH CH CH H Me 〉2,4-二>臭-6-二鼠甲基亞石黃酿基苯基 1-199 4-硝基苯基 CH CH CH CH H Me 〉2,4-二溴-6-三氟甲基亞磺醯基苯基 1-200 4-氮基苯基 CH CH CH CH H Me ;2,4-二溴-6-三氟曱基亞磺醯基苯基 72 200836629 表 1(11) 化合物 編號 Qi A、 a,2 A,3 A,4 Ri r2 q2 1-201 苯基 CH CH CH CH Me Me: 2,4-二>臭-6-^氣甲基亞石黃酿基苯基 1-202 2-氟苯基 CH CH CH CH Me Me: 2,4-二溴-6-三氟甲基亞磺醯基苯基 1-203 4-氟苯基 CH CH CH CH Me Me: 2,4-二溴-6-三氟甲基亞磺醯基苯基 1-204 4-氯苯基 CH CH CH CH Me Me 2,4-二>臭-6-二鼠1曱基亞績酿基苯基 1-205 2-氯^比13定-3-基 CH CH CH CH Me Me 2,4-二>臭-6-二氣曱基亞石黃酿基苯基 1-206 4-硝基苯基 CH CH CH CH Me Me 2,4-二>臭-6-二氣甲基亞石黃酸基苯基 1-207 4-氣基苯基 CH CH CH CH Me Me 2,4-二溴-6-三氟曱基亞磺醯基苯基 1-208 苯基 CF CH CH CH H H 2,4-二溴-6-三氟甲基磺醯基苯基 1-209 2-it苯基 CF CH CH CH H H 2,4-二>臭-6-二亂曱基石黃酿基苯基 1-210 4-敦苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基石黃酸基苯基 1-211 4-氯苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基石黃酿基苯基 1-212 2-氣0比咬-3-基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基石黃酿基苯基 1-213 4-硝基苯基 CF CH CH CH H H 2,4-二溴-6-三氟甲基磺醯基苯基 1.214 4-氰基苯基 CF CH CH CH H H 2,4-二溴-6-三氟甲基磺醯基苯基 1-215 苯基 CH CH CH CH Me H 2,4-二>臭-6-^氣甲基石黃酿基苯基 1-216 2-敗苯基 CH CH CH CH Me H 2,4-二溴-6-三氟曱基磺醯基苯基 1-217 4-氟苯基 CH CH CH CH Me H 2,4-二溴-6-三氟曱基磺醯基苯基 1-218 4-氯苯基 CH CH CH CH Me H 2,4-二>臭-6-二氣曱基石黃酿基苯基 1-219 2-氣吼17定-3·基 CH CH CH CH :Me Π 2,4-二>臭-6-二氣甲基石黃酿基苯基 1-220 4-硝基苯基 CH CH CB :CH Me H 2,4·二溴_6_三氟甲基磺醯基苯基 73 200836629 表 1(12) 化合物 編號 Qi a,2 A,3 A,4 Ri r2 q2 1-221 4-氰基苯基 CH CH CH CH Me H 2,4-二>臭-6-二鼠甲基績酿基苯基 1-222 苯基 CH CH CH CH H Me 2,4-二>臭-6-二氣甲基石黃酿基苯基 1-223 2-氟苯基 CH CH CH CH H Me 2,4-二>臭-6-二氣甲基績酿基苯基 1-224 4-氟苯基 CH CH CH CH H Me 2,4-二〉臭-6-二亂曱基石黃酿基苯基 1-225 4-氣苯基 CH CH CH CH H Me 2,4-二>臭-6-二氣曱基石黃酿基苯基 1-226 2-氣°比0定-3-基 CH CH CH CH H Me 2,4-二溴-6-三氟甲基磺醯基苯基 1-227 4-硝基苯基 CH CH CH CH Π Me 2,4-二>臭-6_二氣曱基石黃酿基苯基 1-228 4-氰基苯基 CH CH CH CH H Me 2,4-二>臭-6-二氣曱基石黃基苯基 1-229 苯基 CH CH CH CH Me Me 2,4·二》臭-6-二亂甲基石黃酿基苯基 1-230 2-氟苯基 CH CH CH CH Me Me 2,4-二>臭-6-二鼠曱基石黃酿基苯基 1-231 4-氟苯基 CH CH CH CH Me Me 2,4-二、/臭·6-二氟甲基石黃酿基苯基 1-232 4-氣苯基 CH CH CH CH Me Me 2,4-二溴-6-三氟甲基磺醯基苯基 1-233 2-氣吼12定-3-基 CH CH CH CH Me Me 2,4-二溴-6-三氟曱基磺醯基苯基 1-234 4-硝基苯基 CH CH CH CH Me Me 2,4-二>臭-6-二氣曱基石黃酿基苯基 1-235 4-氰基苯基 CH CH CH CH Me Me 2,4-二>臭-6-二亂甲基石黃酿基本基 1-236 苯基 CF CH CH CH H H 2,4-二>臭-〇-二氣甲基亞績酿基苯基 1-237 2-氟苯基 CF CH CH CH H H 2,4-二>臭-6-二鼠曱基亞石黃酿基苯基 1-238 4-氟苯基 CF CH CH CH H H 2,4-二>臭-6-二氣曱基亞石黃酿基苯基 1-239 4-氯苯基 CF CH ;CE CH :H H 2,4-二>臭-6-三襄甲基亞石黃酿基苯基 1-240 2-氣吼11 定-3-基 CF CH CH CH :H H 2,4-二>臭-6-二氣甲基亞石黃酿基苯基 74 200836629 表 1(13) 化备物 編號 Qi a,2 A,3 A,4 Ri r2 Q2 1-241 4-硝基苯基 CF CH CH CH H H 2,4-二>臭-6-二氣甲基亞石黃酿基苯基 1-242 4-氰基苯基 CF CH CH CH H H 2,4-二>臭-6-二襄甲基亞石黃酿基苯基 1-243 苯基 CH CH CH CH Me H 2,4-二漠-6-三敦甲基亞石黃酸基苯基 1-244 2-氟苯基 CH CH CH CH Me H 2,4-二>臭-6-二氣曱基亞石黃酿基苯基 1-245 4-1苯基 CH CH CH CH Me H 2,4-二>臭-6-二鼠甲基亞石黃酿基苯基 1-246 4-氯苯基 CH CH CH CH Me H 2,4-二溴-6-三氟甲基亞磺醯基苯基 1-247 2-氯°比^定-3-基 CH CH CH CH Me H 2,4-二>臭-6-二鼠曱基亞礦酸基苯基 1-248 4-硝基苯基 CH CH CH CH Me H 2,4-二溴-6-三氟甲基亞磺醯基苯基 1-249 4-氣基苯基 CH CH CH CH Me H 2,4-二溴-6-三氟曱基亞磺醯基苯基 1-250 苯基 CH CH CH CH H Me 2,4-二>臭-6-二氣曱基亞石黃酿基苯基 1-251 2-氟苯基 CH CH CH CH H Me 2,4-二溴-6-三氟甲基亞磺醯基苯基 1-252 4-氟苯基 CH CH CH CH H Me 2,4-二溴-6-三氟甲基亞磺醯基苯基 1-253 4-氯苯基 CH CH CH CH H Me 2,4-二>臭-6-二說甲基亞石黃酿基苯基 1-254 2·氣0比°定-3-基 CH CH CH CH H Me :2,4-二溴-6-三氟甲基亞磺醯基苯基 1-255 4-硝基苯基 CH CH CH CH H Me ;2,4-二溴-6-三氟甲基亞磺醯基苯基 1-256 4-氰基苯基 CH CH CH CH ΊΓ X w Me ;z,4-二〉臭-6-二氣甲基亞石黃酿基笨基 1-257 苯基 CH CH CH CH :Me Me 丨2,4-二溴-6-三氟甲基亞磺醯基苯基 1-258 2-氟苯基 CH CH CH CH :Me Me ;2,4-二溴-6-三氟甲基亞磺醯基苯基 1-259 4-氟苯基 CH CH CH CE [Me ;2,4-二溴-6-三氟甲基亞磺醯基苯基 1-260 | 4-氯苯基 CH CH CE [CH [Me )2,4-二溴-6-三氟甲基亞磺醯基苯基 75 200836629 表 1(14) 化練 編號 Qi A' a,2 a,3 A’4 Ri r2 Q2 1-261 2-氣吼σ定-3-基 CH CH CH CH Me Me 2头二漠+三氟甲基亞續醯基苯基 1-262 4·硝基苯基 CH CH CH CH Me Me 2,Φ二溴+三氟曱基亞磺醯基苯基 1-263 4·^»基 CH CH CH CH Me Me 2,Φ二溴+三氟甲基亞續醯基苯基 1-264 笨基 CH CH CH CH H H 4·溴《2-氯各三氟甲基硫苯基 1-265 苯基 CH CH CH CH H H 2-漠冰氯各三氟甲基硫苯基 1-266 苯基 CH CH CH CH H H 2-氯冰(4>氰基苯基三氟甲基苯基 1-267 苯基 CH CH CH CH H H 2_氯4<2-三氟曱基苯基>6«三氟甲基硫苯基 1-268 苯基 CH CH CH CH H H 2,6·二甲基冰(2-备1M-三氟4-三氟曱基乙基)苯基 1-269 2-氟苯基 CH CH CH CH H H 2,6·二甲基4(2-溴三trl·三氟甲基乙基)苯基 1-270 丰氟苯基 CH CH CH CH H H 2,6-二甲基本(2-溴-1Λ2-三氣4-三氟甲基乙基)苯基 1-271 ‘氯苯基 CH CH CH CH H H 2,6-二曱基4<2-溴三氟-1-三氟甲基乙基)苯基 1-272 2-氯口比口定-3-基 CH CH CH CH H H 2,6-二甲基二氣-1-二氟^甲基乙基)苯基 1-273 4·硝 CH CH CH CH H H 2,6*二曱基4<2-溴三氟4-三氟甲基乙基)苯基 1-274 基 CH CH CH CH H H 2,6·二甲基4<2-溴-1Λ2-三氣-1-三氟甲基乙基)苯基 1-275 苯基 CF CH CH CH H H 2,6·二甲基4-(2-漠二氟4-二氟^基乙基)苯基 1-276 2-氟苯基 CF CH CH CH H H 2,6>二甲基冬(2-溴-Ιβ-三氣rl-三氟甲基乙基)苯基 1-277 丰氟苯基 CF CH CH CH H H 2,6»二甲基本(2-溴三氟4-三氟甲基乙基)苯基 1-278 ‘氯苯基 CF CH CH ce :H H 2,6>二曱基專(2-溴4二2-三氟-1-三氟甲基乙1)苯基 1-279 2-鼠口比口定,3-基 :CF CH OH CH :H H 2,6«二曱基车(2-溴4M-三氟-1-三氟甲基乙基)苯基 1-280 “肖絲基 CF CH :CH :CH [H H 2,6·二曱基 1(2-溴4M-三氟rl-三氟甲基乙勒苯基 76 200836629 表 1(15) ^____—一一 化知勿 編號 Qi K' a,2 A、 a,4 Ri r2 1-281 φ祕笨基 CF CH CH CH H H 1-282 笨基 CH CH CH CH Me H 2,6·二甲基4<2-漠 1-283 2-氟笨基 CH CH CH CH Me H 2,6·二曱基顿⑽ 1-284 丰氟笨基 CH CH CH CH Me H 2,6-二甲基"4<2善0三^^®^^^ 1-285 本氯笨基 CH CH CH CH Me H 2冬-曱基4(2·溴似二乙輕畢 1-286 2-氯%π定士某 CH CH CH CH Me H 2,6-二甲基车(2-^-0三氟-1-二氟甲基乙基)本基 1-287 丰硝基笨基 CH CH CH CH Me H 吵二曱基车(2-溴-1设三氟4-三氟甲基乙基)苯基 1-288 本II基笨基 CH CH CH CH Me H 2,6·—曱基4-(2-溴甲其乙笑其 1-289 笨基 CH CH CH CH H Me 2,6·二甲基车(2-溴《Ιβ-三氟士三氣甲芦見 1-290 2-氟苯基 CH CH CH CH H Me 2,6-二甲基溴三氟4-:敗甲声 1-291 车氟苯基 CH CH CH CH H Me 2,6·—甲基4»(2-溴二氟4-:氟曱,7 1-292 1-293 木氯苯基 CH CH CH CH H Me ------>Ss 2,孚:?基"HZ-'/lrIM-二氣甲, 2-氯轉3·基 • CH CH CH CH H Me 2,6~ 一甲基-4-(2-溴二螽田 | 1-294 木硝基苯基 CH CH :CH CH H Me ---—~~苯基 丨2,6·三曱基冬㈣似三臺μ : t術装徽 1-295 木fl基笨基 CH CH CH CH H Me 〉2,6·>—甲基*4·(2_溴—1^2^2-三氤二备 w上上u 77 200836629 表 1(16) 編號 Qi A?! a,2 A,3 A’4 Ri r2 q2 1-296 苯基 CH CH CH CH Me Me 2,6~二甲基4<2-溴-1总三氟冬三氟曱基乙基)笨臬 1-297 2-氟苯基 CH CH CH CH Me Me 2,6>二曱基4<2-溴三氟小三氟甲基乙基)茉某 1-298 4»氟苯基 CH CH CH CH Me Me 2,6·二曱基4<2-溴4故三三氟曱基乙基)茉某 1-299 丰氯苯基 CH CH CH CH Me Me 之6:二曱基^―溴·1二^三氟小三氟甲基乙基)茉某 1-300 2-氣口 tb7定各基 CH CH CH CH Me Me 基4<2·溴4总三氟-1-三氟曱基乙基)茉某 1-301 Φ硝基苯基 CH CH CH CH Me Me 2,6^曱基溴·〇三敦·ΐ_三氟曱基乙基)策某 1-302 Φ氰基苯基 CH CH CH CH Me Me 2,6·二甲基车(2·溴4及三氟-μ三氟甲基乙基)装某 1-303 苯基 CH CH CH CH H H 6·溴-8-七氟異丙基奎林基 1-304 2-氟苯基 CH CH CH CH H H 6·漠-8-七氟異丙基音淋-5-基 1-305 4·石肖基苯基 CH CH CH CH H H —----- 6·溴各七敗異丙基者淋-5-基 1-306 苯基 CH CH CH CH H H 2,6»二甲基邻養1又2-三敗-1_三氟甲基乙甚值其 1-307 苯基 CH CH CH CH H H --------- 2,6«二氯三氟4-三氟曱基乙氧慕 1-308 2_象苯基 CH CH CH CH H H 2,6·二氯三氟-1-三氟曱基乙氧勒苯其 1-309 苯基 CH CH CH CH H H 5,7-二溴-2^2,3,3-四敦-1,4·苯并二喝按'、莘 1-310 2-氟苯基 CH CH CH CH H H 5,7-二溴-2233-四敦-1,4«苯并二巧嫁人基 1-311 车氟苯基 CH CH CH CH H H 5,7-二漠-2又3,3_四氟4,本苯并二喝焓人芊 1-312 丰硝基苯基 CH CH CH CH H H 5,7-二溴-2233-四敦-1,4"苯并二喝掠人等 1-313 苯基 CH CH CH [CH H H 5,7-二漠-2^2-二氣 1,3·苯并二号口坐▲苺 1-314 2-氣苯基 CH CH CH [CE H H 2,6·二氯·Φ三氟曱基笨基 1-315 2,6-二氣苯基 CH CH OH [CH [H H 2,6-二氯冬三氟甲基笨基 —---- ——.^ 78 200836629 表 1(17)Compound No. Qi Α, α, 2 A, 3 A, 4: RiJ Q2 1-101 4-Trifluoropyridylpyridinyl CH CH CH < CH HH: 2,4-di> Odor-6-dioxin Methylthiophenyl 1-102 3 -base ratio. -2 -based CH CH CH丨CH HH: 2,4-dibromo-6-trifluoromethylsulfophenyl 1-103 2-phenoxyacridin-3-yl CH CH CH CH HH: 2, 4-II>Smell-6-di-mercaptothiophenyl 1-104 2-methylsulfate ratio 唆-3-yl CH CH CH CH HH 2,4-di>Smell-6-two gas Thiophenyl phenyl 1-105 2,6-dimethoxyacridin-3-yl CH CH CH CH HH 2,4-di>odor-6-dioxadecylthiophenyl 1-106 2,3- Dioxin σ ratio u--5-based CH CH CH CH HH 2,4-dibromo-6-trifluoromethylthiophenyl 1-107 2,5-digas 11 ratio °-3-yl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-80 2,6-diox ratio. Ding-3-yl CH CH CH CH HH 2,4-di>Smell-6-dimethylthiolocenyl 1-109 3,5-digas^specific 唆-bucket-based CH CH CH CH HH 2 , 4-II>Smell-6-dispeltylthiophenyl 1-110 mouth bite-^^-emulsified ^-based CH CH CH CH HH 2,4-di--6-di-methylsulfur Phenyl 1-111 N-mercaptopyrrol-2-yl CH CH CH CH HH 2,4-di>Smell-6-dimethylthiophenyl 1-112-rhept-2-yl CH CH CH CH HH 2,4-di> odor-6-dimethylthiophenyl 1-113 2-indenyl 0 ratio. Well-5-based CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-114 4-difluoromethyl σ-dense-5-yl CH CH CH CH HH 2 ,4-二>Smell-6-dimethylthiophenyl 1-115 11 Fu-2-yl CH CH CH CH HH II:^-二漠^^-二象曱基疏phenyl 1- 116 吱 -3--3-yl CH CH CH CH HH 2,4-di > odor-6-di 1 methyl thiophenyl 1-117 2-tetrafurfuryl CH CH CH CH : HH 2, 4- >Smelly-6-di-murmurylthiophenyl 1-118 3-tetramyl CH CH CH CE :HH 2,4-di>Smell-6-dimethylthiophenyl-1-19 Benzo-bromo-2-yl CH CH CH CH [HH 2,4-di> odor-6-dimethylthiophenyl 1-120 tetrahydrofuran-2-yl CH CH CH CH [HH 2 ,4-dibromo-6-trifluorodecylthiophenyl 68 200836629 Table 1 (7) Compound number Qi Α, α, 2 A, 3 A, 4 Ri r2 Q2 1-121 2-methyl-5,6 Dihydro-4H-indole-3-yl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-122 σ cephen-2-yl CH CH CH CH HH 2,4-di> odor-6·dimurazolylthiophenyl 1-123 oxime-3-yl CH CH CH CH HH 2,4-di> odor-6-di-mercaptosulfur Phenyl 1-124 3-methylthiophene-2·yl CH CH CH CH HH 2,4-di>Smell-6-di-gasmethylthiophenyl 1-125 2-Phase σ-secen-4-yl CH CH CH CH HH 2,4-di>Smell-6-II Gas methylthiophenyl 1-126 2-methyl σ-sept-5-yl CH CH CH CH HH 2,4-di > odor-6-dimethylthiophenyl 1-127 3-chlorothiophene -2-yl CH CH CH CH HH 2,4-di>odor 6-di-mercaptothiophenyl M28 2-chloro sigma-5-yl CH CH CH CH HH 2,4-di -6 -trifluoromethylthiophenyl 1-129 3 - > skoxin-2-yl CH CH CH CH HH 2,4-di > odor-6-di-methylthiophenyl 1-130 2- Bromoporphin-5-yl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl-1-31 3 -deca-but-2-yl CH CH CH CH HH 2, 4-II>Smell-6-dimethylthiophenyl 1-132 3-phenylthiophen-2-yl CH CH CH CH HH 2,4-dibromo-6-trifluoromethylthiophenyl 1 -133 2,4-dimethyldecaxene-5-yl CH CH CH CH HH 2,4-di>odor-6-difluoromethylsulfanyl 1-134 benzo-xethen-2- -Based CH CH CH CH HH 2,4-di>Smell-6-disorder methylthiophenyl 1-135 4-Nitro-1pyrrole-2-yl CH CH CH CH HH 2,4-II -6-dimethylthiophenyl 1-136 3-ethyl-3-oxapyrazol-4-yl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-137 1-methyl-3-nitro-1Η-.嗤-4-yl CH CH CH CH HH 2,4-di,/odor 6-dimethylthiophenyl 1-138 3-chloro-1-indolyl-1 Η-pyrazole-4-yl CH CH CH CH HH 2,4-di>Smell-6-trifluoromethylthiophenyl 1-139 3-bromo small methyl-1 Η-pyrazole-4-yl CH CH CH CH HH 2,4-II Bromo-6-trifluoromethylthiophenyl 1-140 1-methyl-3-fluoromethyl-1 Η- ° than 嗤-4-yl CH CH CH CH HH 2,4-di > Dimethylthiophenyl 69 200836629 Table 1 (8) Chemicals number Qi A5! a, 2 A, 3 A, 4 Ri r2 q2 1-141 1-methyl-5-trifluoromethyl-1H- π ratio tr sit-4-yl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-142 isoxazol-5-yl CH CH CH CH HH 2,4· Dibromo-trifluoromethylsulfenylphenyl 1-143 4-trifluoromethylthiazol-5-yl CH CH CH H H 2,4-dibromo-6-trifluorodecylthiophenyl 1-144 2, 4-Dimercaptothiazol-5-yl CH CH CH CH HH 2,4-dibromo-6-trifluoromethylthiophenyl 1445 2-ethyl-4-methylthiazol-5-yl CH CH CH CH HH 2,4-di>odor-6-difluoromethylthiophenyl 1-146 2-chloro-4-methylthiazol-5-yl CH CH CH CH HH 2,4-dibromotrifluoromethyl Thiophenyl 1-147 3-methyl-isothiazol-5-yl CH CH CH CH H H 2,4-di>Smell-6-di-methylthiophenyl 1-148 3,4-dichloro-isothiazol-5-yl CH CH CH CH HH 2,4-di> - dimethyl thiophenyl 1-149 3-chlorobenzothiazol-2-yl CH CH CH H H 2,4-dibromo-6-trifluoromethyl thiophenyl 1-150 2,2- 1 benzo[1.3]dioxazole-5-yl CH CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-151 2,2-di-benzo-[1.3 Dicarbazole _4-based CH CH CH CH HH 2,4-di > odor-6-disorder methylthiobenyl 1-152 phenyl CF CH CH CH HH 2,4-dibromo-6- Trifluoromethylthiophenyl 1-153 2-phenylphenyl CF CH CH H H 2,4-di>odor-6-dimethylthiophenyl 1-154 4-fluorophenyl CF CH CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-155 4-chlorophenyl CF CH CH HH 2,4-di>odor-6-dimethylthiophenyl 1-156 2_rat bite-3-yl CF CH CH CH HH 2,4-dibromo-6-trifluoromethylthiophenyl 1457 4-nitrophenyl CF CH CH H H 2,4·2 Bromo-6-trifluoromethylthiophenyl 1-158 4-cyanophenyl CF CH CH:CH HH 2,4-di>odor-6-di-mercaptothiophenyl 1-159 phenyl CH CH :CH ;CE Me )H 2,4-di>Smelly-6-digas sulfhydryl 1-160 2-Chlorophenyl CH:CE [CH [CH ;Mc ^ H 2,4-dibromo-6-trifluoromethylthiophenyl 70 200836629 Table i(9) Compound No. Qi α, 2 A, 3 A ,4 Ri r2 Q2 1-161 4-fluorophenyl CH CH CH Me H 2,4-dibromo-trifluoromethylsulfophenyl 1-162 4-chlorophenyl CH CH CH Me H 2,4 - two > odor-6 - two said methyl hydrazine phenyl 1-163 2-gas.唆-3-yl CH CH CH CH Me H 2,4-dibromo-trifluoromethylthiophenyl 1-164 4-nitrophenyl CH CH CH CH Me H 2,4-dibromo-6- Trifluoromethylthiophenyl 1-165 4-cyanophenyl CH CH CH Me H 2,4-dibromo-6-trifluoromethylthiophenyl 1-166 phenyl CH CH CH CH H Me 2 ,4-dibromo-6-difluoromethylthiophenyl ί-167 2-say phenyl CH CH CH H Me 2,4-dibromo-6-trifluoromethylthiophenyl 1-168 4- Phenyl CH CH CH CH H Me 2,4-dibromo-6-trioxamethylthiophenyl 1-169 4-chlorophenyl CH CH CH CH H Me 2,4-dibromo-6-trifluoro Methylthiophenyl 1-170 2-chloro π ratio -3-yl CH CH CH CH H Me 2,4-dibromo-6-trifluoromethyl thiophenyl 1-171 4-nitrophenyl CH CH CH CH H Me 2,4_二>Smell-6-trifluoromethylthiophenyl 1-172 4-cyanophenyl CH CH CH CH H Me 2,4-dibromo-6-trifluoromethyl Thiophenyl phenyl 1-173 phenyl CH CH CH Me Me 2,4-dibromo-6-trifluoromethylthiophenyl 1-174 2-fluorophenyl CH CH GH CH Me Me 2,4-II >Smelly-6-disorganized methylthiophenyl 1-175 4-decylphenyl CH CH CH Me Me 2,4-dibromo-trifluoromethylsulfophenyl 1-176 4-chlorophenyl CH CH CH CH Me Me 2,4-two> Wu-6-two gas基石瓦phenyl 1-177 2-gas bite-!^-based CH CH CH CH Me Me 2,4-di>odor-6-dimethylthiophenyl 1-178 4-wall phenyl CH CH CH CH Me Me 2,4-di>Smell-6-dimethylthiophenyl 1-179 4-cyanophenyl CH CH CH Me Me 2,4_2>Smelly-6- Difluoromethylthiophenyl 1-180 phenyl CF CH CH H H 2,4-dibromo-6-trifluoromethylsulfinyl 1 phenyl 71 200836629 Table 1 (10) Compound number Qi A5! a , 2 a,3 A,4 Ri r2 Q2 1-181 2-Phenylphenyl CF CH CH H H 2,4-di>Smell-6-di-gas methyl sulphite Yellow phenyl 1-182 4 -fluorophenyl CF CH CH HH 2,4-di>Smell-6-di-gas methyl sulphate phenyl 1-183 4-chlorophenyl CF CH CH H H 2,4-II Odor-6-difluoroimethyl sulfite yellow phenyl 1-184 2-chloropyridin-3-yl CF CH CH H H 2,4-dibromo-6-trifluoromethylsulfinyl benzene 1-185 4-Nitrophenyl CF CH CH CH HH 2,4-di>Smell-6-dimethylmethyl stellite phenyl 1-168 4-nitrophenyl CF CH CH CH HH 2,4-di> odor-6-trimethyl fluorenyl phenyl phthalate 1-187 stupid CH CH CH CH Me H 2,4-di > odor-6-dimethylmethyl stone Styrene phenyl 1-188 2-phenyl phenyl CH CH CH CH H H 2,4-di> odor-6-diqi fluorenyl phenyl phenylphenyl M89 phenyl CH CH CH CH H H 2 ,4-di>Smell-6-di-gas methyl sulphate yellow phenyl 1-190 4-chlorophenyl CH CH CH CH H 2,4-di> odor-6-dimethylmethyl Phosphine phenyl 1-191 2-chloropyridin-3-yl CH CH CH CH Me H 2,4-di > odor-6-di-gas methyl sulphate phenyl 1-192 4 -nitrophenyl CH CH CH CH Me H 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1:193 4-cyanophenyl CH CH CH Me H 2,4-di >Smell-6-two mouse A. Kea phenyl phenyl 1-194 phenyl CH CH CH H Me 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-195 2-fluorophenyl CH CH CH CH Me 2,4-di>Smell-6-di-mouse methyl sulphate phenyl 1-196 4-fluorophenyl CH CH CH H Me 2,4-II >Smelly-〇-二乱methyl亚绩酸泰本基1-197 4-Chlorophenyl CH CH CH CH H Me ,2,4-二>Smell-$-二鼠曱基亚石黄Phenyl 1-198 2-mouse 0 ratio. Ding-3-yl CH CH CH CH H Me 〉2,4-di>Smell-6-dimethylmethyl sulphate phenyl 1-109 4-nitrophenyl CH CH CH CH H Me 〉 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-200 4-nitrophenyl CH CH CH H Me ; 2,4-dibromo-6-trifluorodecylsulfin Nonylphenyl 72 200836629 Table 1 (11) Compound No. Qi A, a, 2 A, 3 A, 4 Ri r2 q2 1-201 Phenyl CH CH CH CH Me Me: 2,4-di > -^ gas methyl sulphate phenyl 1-202 2-fluorophenyl CH CH CH Me Me: 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-202 4 -fluorophenyl CH CH CH Me Me: 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-242 4-chlorophenyl CH CH CH CH Me Me 2,4-di > ; 臭-6-二鼠1曱基亚谱酿基1-205 2-Chlorine^13定-3-基CH CH CH CH Me Me 2,4-二>Smell-6-dioxin Kea stone yellow base phenyl 1-206 4-nitrophenyl CH CH CH CH Me Me 2,4-di > odor-6-di-gas methyl linoleate phenyl 1-207 4- Phenylphenyl CH CH CH CH Me Me 2,4-dibromo-6-trifluorodecylsulfenylphenyl 1-208 Phenyl CF CH CH CH HH 2,4-dibromo-6-trifluoro Methylsulfonyl Phenyl 1-209 2-it phenyl CF CH CH H H 2,4-di> odor-6-disorder fluorenyl yellow phenyl 1-210 4- phenyl phenyl CF CH CH H H 2 4-II>Smell-6-dimethylmethyl tartaric acid phenyl 1-211 4-chlorophenyl CF CH CH H H 2,4-di>Smell-6-dimethylmethyl sallow Phenylphenyl 1-212 2-gas 0-bite-3-yl CF CH CH CH HH 2,4-di>Smell-6-dimethylmethyl fluorenylphenyl 1-261 4-nitrobenzene CF CH CH CH HH 2,4-Dibromo-6-trifluoromethylsulfonylphenyl 1.214 4-cyanophenyl CF CH CH H H 2,4-dibromo-6-trifluoromethylsulfonate Nonylphenyl 1-215 Phenyl CH CH CH CH Me H 2,4-di>Smell-6-^Gasmethylglycolylphenyl 1-216 2-Phenyl CH CH CH CH Me H 2,4-Dibromo-6-trifluorodecylsulfonylphenyl1-217 4-fluorophenyl CH CH CH Me H 2,4-dibromo-6-trifluorodecylsulfonylphenyl 1-218 4-chlorophenyl CH CH CH CH H 2 2,4-di>Smell-6-dioxyl fluorenyl phenyl phenyl 1-219 2-gas hydrazine 17 1-3 base CH CH CH CH :Me Π 2,4-di>Smell-6-dimethylmethyl fluorenylphenyl 1-220 4-Nitrophenyl CH CH CB :CH Me H 2,4·Dibromo_6_ Trifluoromethylsulfonylphenyl 73 200836629 Table 1(12) Compound number Qi a,2 A,3 A,4 Ri r2 q2 1-221 4-cyanophenyl CH CH CH Me H 2,4-di>Smell-6-two mouse Base phenyl phenyl 1-222 phenyl CH CH CH CH H Me 2,4-di > odor-6-dimethylmethyl fluorenyl phenyl 1-223 2-fluorophenyl CH CH CH CH H Me 2,4-di>Smell-6-di-methylmethyl-branched phenyl 1-224 4-fluorophenyl CH CH CH CH 2 2,4-di>odor-6-disorder sill Yellow-brown phenyl 1-225 4-Phenylphenyl CH CH CH CH H 2,4-di>Smell-6-dioxyl fluorite yellow phenyl 1-226 2-gas ratio 0- 3-based CH CH CH CH H Me 2,4-dibromo-6-trifluoromethylsulfonylphenyl 1-227 4-nitrophenyl CH CH CH CH Π Me 2,4-di > -6_二气曱石石黄-based phenyl 1-228 4-cyanophenyl CH CH CH CH H Me 2,4-di> odor-6-diqi fluorenyl phenyl phenyl 1-229 benzene CH CH CH CH Me Me 2,4·二》臭-6-二乱乱methyl石黄毛基1-230 2-fluorophenyl CH CH CH CH Me Me 2,4-二> 6-two squirrel basestone yellow phenyl 1-231 4-fluorophenyl CH CH CH Me Me 2,4-di, / odor · 6-difluoromethyl zeolitic phenyl 1-232 4 -gas Phenyl CH CH CH CH Me Me 2,4-dibromo-6-trifluoromethylsulfonylphenyl 1-233 2-gas oxime 12 -3-yl CH CH CH CH Me Me 2,4-II Bromo-6-trifluorodecylsulfonylphenyl 1-234 4-nitrophenyl CH CH CH CH Me Me 2,4-di>odor-6-dioxyl fluorenyl phenyl 1- 235 4-cyanophenyl CH CH CH CH Me Me 2,4-di>Smell-6-disintegrated methyl stone yellow base base 1-263 phenyl CF CH CH CH HH 2,4-di> Odor-〇-di-gas methyl saponin phenyl 1-273 2-fluorophenyl CF CH CH CH HH 2,4-di> odor-6-dimur 曱 亚 亚 黄 黄 苯基 1 -238 4-fluorophenyl CF CH CH CH HH 2,4-di>odor-6-diqi fluorene phenyl phenyl 1-2-3 4-chlorophenyl CF CH ;CE CH :HH 2 ,4-di>Smell-6-trimethylsulfide yellow phenylphenyl 1-240 2-gas oxime 11 -3--3-CF CH CH CH :HH 2,4-di> - Di-gas methyl sulphate yellow phenyl 74 200836629 Table 1 (13) Chemical preparation number Qi a, 2 A, 3 A, 4 Ri r2 Q2 1-241 4-nitrophenyl CF CH CH CH HH 2,4-di>Smell-6-di-gas methyl garnet yellow phenyl 1-242 4-cyanophenyl CF CH CH H H 2,4-di>Smell-6-di Kia Phytophenyl phenyl 1-243 phenyl CH CH CH CH Me H 2,4-di -6-Santon methyl linoleic acid phenyl 1-244 2-fluorophenyl CH CH CH CH Me H 2,4-di>Smell-6-diqi fluorenyl sulphate phenyl 1-245 4-1 phenyl CH CH CH Me H 2,4-di>Smell-6-dual mouse Methyl sulphate phenyl 1-246 4-chlorophenyl CH CH CH CH Me H 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-247 2-chloro ratio ^定-3-基CH CH CH CH Me H 2,4-二>Smell-6-dimurium quinone phenylphenyl 1-248 4-nitrophenyl CH CH CH Me H 2, 4-dibromo-6-trifluoromethylsulfinylphenyl 1-245 4-oxylphenyl CH CH CH Me H 2,4-dibromo-6-trifluorodecylsulfinylbenzene 1-250 phenyl CH CH CH CH H 2 2,4-di> odor-6-diqi fluorenyl phenyl phenyl 1-251 2-fluorophenyl CH CH CH H Me 2, 4-Dibromo-6-trifluoromethylsulfinylphenyl 1-252 4-fluorophenyl CH CH CH H Me 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-253 4-chlorophenyl CH CH CH CH H Me 2,4-di>Smell-6-two said methyl slate yellow phenyl phenyl 1-254 2 · gas 0 ratio °-3-yl CH CH CH CH H Me : 2,4-dibromo-6-three Fluoromethylsulfinylphenyl 1-255 4-nitrophenyl CH CH CH H Me ; 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-256 4-cyano Phenylphenyl CH CH CH CH ΊΓ X w Me ;z,4-di>odor-6-diqimethyl yttrium yellow aryl base 1-257 phenyl CH CH CH CH :Me Me 丨2,4- Dibromo-6-trifluoromethylsulfinylphenyl 1-258 2-fluorophenyl CH CH CH : Me Me ; 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-259 4-fluorophenyl CH CH CH CE [Me ; 2,4-dibromo-6-trifluoromethylsulfinylphenyl 1-260 | 4-chlorophenyl CH CH CE [CH [Me 2,4-dibromo-6-trifluoromethylsulfinylphenyl 75 200836629 Table 1 (14) Chemical practice number Qi A' a, 2 a, 3 A'4 Ri r2 Q2 1-261 2-吼σ定-3-基CH CH CH CH Me Me 2 头二漠+Trifluoromethyl hydrazinyl 1-262 4·Nitrophenyl CH CH CH Me Me 2, Φ Dibromo + Trifluoromethanesulfinylphenyl phenyl 1-263 4·^»-based CH CH CH CH Me Me 2, Φ dibromo + trifluoromethyl succinyl phenyl 1-246 stupid CH CH CH CH HH 4. Bromine "2-chloro-trifluoromethylthiophenyl 1-265 phenyl CH CH CH H H 2 - Molycol Chlorine Trifluoromethylthiophenyl 1-266 phenyl CH CH CH CH HH 2-chloro ice (4> cyanophenyl trifluoromethylphenyl 1-267 phenyl CH CH CH H H 2 2 chloro 4 < 2-trifluoromethylphenyl >6 «trifluoromethylthiophenyl 1-268 phenyl CH CH CH H H 2 2,6·dimethyl ice (2-prepared 1M-trifluoro 4-trifluorodecylethyl)phenyl 1- 269 2-fluorophenyl CH CH CH CH HH 2,6· dimethyl 4(2-bromotritrt·trifluoromethylethyl)phenyl 1-270 fluorophenyl phenyl CH CH CH H H 2,6 - Dimethyl basic (2-bromo-1 fluorene 2-tris 4-trifluoromethylethyl)phenyl 1-271 'chlorophenyl CH CH CH CH HH 2,6-dimercapto 4<2-bromotrifluoro -1-trifluoromethylethyl)phenyl 1-172 2-Chloro-Butyl-3-yl CH CH CH CH HH 2,6-Dimethyldi-l-difluoro-methylethyl Phenyl 1-273 4 · Nit CH CH CH CH HH 2,6* Dimercapto 4<2-bromotrifluoro 4-trifluoromethylethyl)phenyl 1-274-based CH CH CH CH HH 2, 6·Dimethyl 4<2-bromo-1Λ2-triseo-1-trifluoromethylethyl)phenyl 1-275 phenyl CF CH CH CH HH 2,6·dimethyl 4-(2- Difluoro-4-difluoro(ethyl)phenyl)1-276 2-fluorophenyl CF CH CH HH 2,6>Dimethyl winter (2-bromo-Ιβ-tri-gas rl-trifluoromethyl Phenyl 1-27 7 fluorinated phenyl CF CH CH CH HH 2,6»dimethyl basic (2-bromotrifluoro 4-trifluoromethylethyl)phenyl 1-278 'chlorophenyl CF CH CH ce :HH 2,6> Diterpene-based (2-bromo-4-ditrifluoro-1-trifluoromethylethyl 1)phenyl 1-279 2-merole, 3-yl: CF CH OH CH :HH 2, 6 «二曱基车(2-Bromo 4M-trifluoro-1-trifluoromethylethyl)phenyl 1-280 "Shaws CF CH : CH : CH [HH 2,6 · Dimercapto 1 ( 2-Bromo 4M-trifluoro-rl-trifluoromethyle-phenylphenyl 76 200836629 Table 1 (15) ^____—I don't know how to number Qi K' a,2 A, a,4 Ri r2 1-281 φ Secret Stupid CF CH CH CH HH 1-282 Stupid CH CH CH CH Me H 2,6·Dimethyl 4<2-Mool 1-283 2-Fluoro Stable CH CH CH CH Me H 2,6·II曱基顿(10) 1-284 丰氟基基 CH CH CH CH Me H 2,6-dimethyl "4<2善0三^^®^^^ 1-285 This chlorinated CH CH CH CH Me H 2 winter - sulfhydryl 4 (2 · bromine like diethylene light complete 1-286 2-chloro% π 士士 a CH CH CH CH Me H 2,6-dimethyl car (2-^-0 trifluoro- 1-Difluoromethylethyl) Benzo 1-287 nitro-nitro stupyl CH CH CH CH Me H Noisy bismuth car (2-bromo-1 with trifluoro 4-trifluoromethylethyl) phenyl 1-288 this II基笨基 CH CH CH CH Me H 2,6·—曱基4-(2-Bromomethystamine II-89 Stupid CH CH CH CH H Me 2,6·Dimethyl car (2- Bromine "Ιβ-Trifluorostrip three gas reeds see 1-290 2-fluorophenyl CH CH CH CH H Me 2,6-dimethylbromotrifluoro 4-: defeated Acoustic 1-291 car fluorophenyl CH CH CH CH H Me 2,6·-methyl 4»(2-bromodifluoro 4-:fluoroantimony, 7 1-292 1-293 lichlorophenyl CH CH CH CH H Me ------> ;Ss 2, Fu:? Base"HZ-'/lrIM-two gas, 2-chloro to 3·yl • CH CH CH CH H 2,6~ monomethyl-4-(2-bromide) | 1-294 Phenyl phenyl CH CH : CH CH H Me ---~~ phenyl 丨 2,6 · triterpene winter (four) like three sets of μ : t surgery emblem 1-295 wood fl base stupid CH CH CH CH H Me 〉2,6·>-Methyl*4·(2_Bromo-1^2^2-三氤二备w上上u 77 200836629 Table 1(16) No. Qi A?! a, 2 A, 3 A'4 Ri r2 q2 1-296 Phenyl CH CH CH CH Me Me 2,6~Dimethyl 4<2-Bromo-1 Total Trifluoro-Winter Trifluorodecyl Ethyl) Clumpy 1-129 2- Fluorophenyl CH CH CH CH Me Me 2,6> Dimercapto 4<2-Bromotrifluorosuccinylethylethyl)Molyl 1-198 4»Fluorophenyl CH CH CH Me Me 2,6· Dimercapto 4<2-bromo 4, tritrifluorodecylethyl) Molybdenum 1-199 chlorophenyl phenyl CH CH CH CH Me Me 6: Dimercapto- bromo·1 bis trifluorotrifluoro Methyl ethyl) methane 1-300 2-air port tb7 each group CH CH CH CH Me Me base 4 < 2 · bromine 4 total trifluoro-1-trifluoromethylidene ethyl) methane 1-301 Φ nitrate Phenylphenyl CH CH CH Me Me 2,6^曱 溴 溴 〇 敦 敦 ΐ ΐ 曱 曱 曱 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 1-3 2,6· dimethyl car (2·Bromo 4 and trifluoro-μtrifluoromethylethyl) loaded with 1-103 phenyl CH CH CH H H 6 · bromo-8-heptafluoroisopropyl quinine 1-304 2-fluorophenyl CH CH CH H H 6 · -8 - heptafluoroisopropyl propyl -5 - yl 1-305 4 · succinyl phenyl CH CH CH CH HH —----- 6 · bromine each seven isopropyl lysine-5-yl 1-306 phenyl CH CH CH CH HH 2,6» dimethyl neighbor 1 and 2 - 3 -1 -trifluoromethyl B 1-307 phenyl CH CH CH CH HH --------- 2,6 «dichlorotrifluoro 4-trifluoromethyl ethoxy oxy 1-308 2_ like phenyl CH CH CH H H 2 ,6·dichlorotrifluoro-1-trifluorodecyl ethoxybenzene Benzene 1-109 phenyl CH CH CH CH HH 5,7-dibromo-2^2,3,3-tetrad-1,4 ·Benzene two drink according to ', 莘 1-310 2-fluorophenyl CH CH CH H H 5,7-dibromo-2233-four Dun-1,4« benzodiabene married base 1-311 car fluoride Phenyl CH CH CH CH HH 5,7-II--2 and 3,3_tetrafluoro 4, Benzo benzoquinone 芊1-312 nitrophenyl phenyl CH CH CH H H 5,7-II Bromo-2233-四敦-1,4"Benzene II, plucking people, etc. 1-313 Phenyl CH CH CH [CH HH 5,7-二漠-2^2-二气1,3·Benzene 2 Sit ▲ Raspberry 1-314 2-gas benzene CH CH CH [CE HH 2,6·dichloro·Φ trifluoromethyl phenyl 1-35 2,6-di-phenylphenyl CH CH OH [CH [HH 2,6-dichloro-t-trifluoromethyl] Base—---- ——.^ 78 200836629 Table 1 (17)
化 編號 Qi α,2 A,3 A,4 Ri r2 q2 1-316 苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基苯基 1-317 4_氣-3-石肖基苯基 CH CH CH CH H H 2,4-二溴-6-三氟曱基苯基 1-318 5-氟-2-頌基苯基 CH CH CH CH H H 2,4-二溴-6-二氟曱基苯基 1-319 2-氣-6-埃苯基 CH CH CH CH H H 2,4-二溴-6_三氟甲基苯基 1-320 4-硝基苯基 CH CH CH CH H H 2,4-二>臭-6-二敗曱基苯基 1-321 4-苯基偶氮苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基苯基 1-322 2-(4-三氟曱基苯基)苯基 CH CH CH CH H H 2,4·二溴-6-三氟甲基苯基 1-323 4-甲氧羰基苯基 CH CH CH CH H H 2,4-二漠-6-二氟甲基苯基 1-324 2,6-二曱氧基苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基苯基 1-325 吼嘻-2-基 - CH CH CH CH H H 2,4-二溴-6-三氟甲基苯基 1-326 5-(苯基乙快基)σ夫喃-2-基 CH CH CH CH H H 2,4-二>臭-6-二氣曱基苯基 1-327 5-(苯基乙快基户比°定-3-基 CH CH CH CH H H 2,4-二溴-6-三氟甲基苯基 1-328 4-吡啶基 CH CH CH CH H H 2,4-二溴各三氟甲基苯基 1-329 2,4-二氣-3-σ比σ定基 CH CH CH CH H H 2,4-二>臭-6-三氟甲基苯基 1-330 3-乙炔基 CH CH CH CH H H 2,4-二溴-6-三氟甲基苯基 1-331 2-甲氧基苯基 CH CH CH CH H H 2,4-二>臭-6-二氣甲基苯基 1-332 2-苯氧基苯基 CH CH CH CH H H 2,4-二溴-6-三氟甲基苯基 1-333 2-啥琳基 CH CH CH CH H H 2,4-二溴-6-三氟甲基苯基 1-334 4-喹I基 CH CH CH CH H H 2,4-二>臭-6-二氟曱基苯基 1-335 2-苯基啥琳-4-基 CH :CH CH CH :H H 2,4-二溴-6·三氟甲基苯基 79 200836629Chemical number Qi α,2 A,3 A,4 Ri r2 q2 1-316 Phenyl CH CH CH CH HH 2,4-Dibromo-6-trifluoromethylphenyl 1-317 4_Ga-3-Shi Xiaoji Phenyl CH CH CH CH HH 2,4-dibromo-6-trifluorodecylphenyl 1-318 5-fluoro-2-mercaptophenyl CH CH CH CH HH 2,4-dibromo-6-di Fluorodecylphenyl 1-319 2-Ga-6-Ethyl CH CH CH CH HH 2,4-Dibromo-6-trifluoromethylphenyl 1-320 4-Nitrophenyl CH CH CH CH HH 2,4-di>Smell-6-dispelenylphenyl 1-321 4-phenylazophenyl CH CH CH CH HH 2,4-dibromo-6-trifluoromethylphenyl 1 -322 2-(4-Trifluorodecylphenyl)phenyl CH CH CH HH 2,4·dibromo-6-trifluoromethylphenyl 1-232 4-methoxycarbonylphenyl CH CH CH CH HH 2,4-di--6-difluoromethylphenyl 1-324 2,6-dimethoxyphenyl CH CH CH CH HH 2,4-dibromo-6-trifluoromethylphenyl 1 -325 吼嘻-2-yl-CH CH CH CH HH 2,4-dibromo-6-trifluoromethylphenyl 1-326 5-(phenylethyl carbyl) succinyl-2-yl CH CH CH CH HH 2,4-di>Smell-6-di-p-decylphenyl 1-327 5-(phenylethyl fast keto ratio -3--3-CH CH CH CH HH 2,4-dibromo -6-trifluoromethylphenyl 1-328 4-pyridyl CH CH CH CH HH 2,4-dibromo-trifluoromethylphenyl 1-329 2,4-digas-3-σ ratio σ-based CH CH CH CH HH 2,4-di > odor-6-three Fluoromethylphenyl 1-330 3-ethynyl CH CH CH CH HH 2,4-dibromo-6-trifluoromethylphenyl 1-331 2-methoxyphenyl CH CH CH HH 2,4 -二>Smell-6-dimethylphenyl 1-332 2-phenoxyphenyl CH CH CH HH 2,4-dibromo-6-trifluoromethylphenyl 1-333 2-indole琳基 CH CH CH CH HH 2,4-dibromo-6-trifluoromethylphenyl 1-334 4-quino-based CH CH CH CH HH 2,4-di> odor-6-difluorodecyl Phenyl 1-335 2-phenylindolin-4-yl CH: CH CH CH :HH 2,4-dibromo-6·trifluoromethylphenyl 79 200836629
表 1(18) 化細勿 編號 Qi Α5! α,2 · A53 A,4 Ri r2 q2 1-336 秦基 CH CH i CH CH H H 2,4-二溴-6-三氟甲基苯基 1-337 蒽冬基 CH CH丨 CH CH H H 2,4-二溴各三氟甲基苯基 1-338 σ定-9-基 CH CH- CH CH H H 2,4-二 >臭-6-二氟甲基苯基 1-339 苯基 CH CH CH CH H H 2-溴-4,6-雙(三氟甲基)苯基 1-340 苯基 CH CH CH CH H H 2,4-雙(三氟曱基)苯基 1-341 2-氰基苯基 CH CH CH CH H H 2,4-雙(三|L甲基)苯基 1-342 3,5-二氣苯基 CH CH CH CH H H 2,4-雙(三氟甲基)苯基 1-343 2,6-二氣苯基 CH CH CH CH H H 2,4-雙(三甲基)苯基 1-344 2,3,4-三氟苯基 CH CH CH CH H H 2,4-雙(三Ιι甲基)苯基 1-345 4-氯苯基 CH CH CH CH H H 2,4-雙(三篆甲基)苯基 1-346 2,4-二氯苯基 CH CH CH CH H H 2,4-雙(三氣甲基)苯基 1-347 4,5-二氟τ2-硝基苯基 CH CH CH CH H H 2,4-雙(三1甲基)苯基 1-348 3-1-2-甲基苯基 CH CH CH CH H Π 2,4-雙(三氟甲基)苯基 1-349 4-甲基苯基 CH CH CH CH H H 2,4-雙(三氟曱基)苯基 1-350 4-乙基苯基 CH CH CH CH H H 2,4-雙(三氣甲基)苯基 1-351 3-曱氧基苯基 CH CH CH CH H H 2,4-雙(三氣甲基)苯基 1-352 4-曱氧基苯基 CH CH CH :CH H H 2,4·雙(三氟甲基)苯基 1-353 354,5_三甲氧基苯基 CH CH CH [CH Π H 2,4-雙(三氟曱基)苯基 1-354 1-萘基 CH CH CE [CH :H H 2,4-雙(三氟曱基)苯基 1-355 2-萘基 CH CH CH [CH ;H H 2,4-雙(三氣曱基)苯基 80 200836629 表 1(19) 化緣 編號 Qi α,2 AV A% Ri r2 Q2 1-356 5-氣-2-ϋ塞吩基 CH CH CH CH H H 2,4-雙(三氟甲基)笨基 1-357 2-氣-3·11比ϋ定基 CH CH CHi CH H H 2,4-雙(三氟甲基)苯基 1-358 6-甲基-2-11比σ定基 CH CH CH CH H H 2,4-雙(三氣甲基)苯基’ 1-359 5-氣-2-吼12定基 CH CH CH CH H H 2,4-雙(三氟甲基)苯基 1-360 6-輕基-2-吼唆基 CH CH CH CH H H 2,4-雙(三氟甲基)苯基 1-361 5-曱基-°比。井-2-基 CH CH CH CH H H 2,4_雙(三氟甲基)苯基 1-362 ϋ比畊-2-基 CH CH CH CH H H 2,4-雙(三|1甲基)苯基 1-363 5-甲基-2-噻吩基 CH CH CH CH H H 2,4-雙(三1甲基)苯基 1-364 3-甲基-2-噻吩基 CH CH CH CH H H 2,4-雙(三氟甲基)笨基 1-365 苯基 CH CH CH CH H H 2,5-雙(三氟甲基)苯基 1-366 苯基 CH CH CH CH H H 2-氯·4,6-雙(三氟曱基)苯基 1-367 2,6-二氟苯基 CH CH CH CH H H 2-氯-4,6-雙(三1甲基)苯基 1-368 4-硝基苯基 CH CH CH CH H H 2-氯-4,6-雙(三氟甲基)苯基 1-369 苯基 CH CH CH CH H Π 2-溴各曱基-4-(三氟甲烷磺 醯氧基)苯基 1-370 2-氟苯基 CH CH CH CH H H 2_溴-6-曱基冬(三氟曱烷磺 氧基)苯基 1-371 苯基 CH CH CH CH H H 2-氯-6-曱基-4-(二氣甲烧石黃 醯氧基)苯基 1-372 苯基 CH CH CH CE [H H 2_甲基_4-(三氟甲烷磺醯氧 基)苯基 1-373 苯基 CH CE CH CB [H H 4-(七氣異丙基)-2-曱基奈基 1-374 2-氟苯基 CH CH :CH CE H H 4-(七氟異丙基)-2-甲基萘基 1-375 苯基 1 CH CB :CH :ct H H 7-七氟異丙基二氳茚-4-基 81Table 1 (18) The details are not numbered Qi Α5! α,2 · A53 A,4 Ri r2 q2 1-336 Qinji CH CH i CH CH HH 2,4-Dibromo-6-trifluoromethylphenyl 1 -337 蒽冬基 CH CH丨CH CH HH 2,4-dibromo-trifluoromethylphenyl 1-38 σ-decyl-9-yl CH CH- CH CH HH 2,4-di > odor-6- Difluoromethylphenyl 1-39 phenyl CH CH CH CH HH 2-bromo-4,6-bis(trifluoromethyl)phenyl 1-340 phenyl CH CH CH H H 2,4-double (three Fluorodecyl)phenyl 1-341 2-cyanophenyl CH CH CH HH 2,4-bis(tri-L)phenyl 1-342 3,5-diphenylphenyl CH CH CH CH HH 2,4-bis(trifluoromethyl)phenyl 1-343 2,6-diphenylphenyl CH CH CH H H 2,4-bis(trimethyl)phenyl 1-344 2,3,4- Trifluorophenyl CH CH CH H H 2,4-bis(trimethylene)phenyl 1-345 4-chlorophenyl CH CH CH CH HH 2,4-bis(trimethyl)phenyl 1- 346 2,4-Dichlorophenyl CH CH CH H H 2 2,4-bis(trimethyl)phenyl 1-347 4,5-difluoroτ2-nitrophenyl CH CH CH HH 2,4 - bis(trimethyl)phenyl 1-348 3-1-2-methylphenyl CH CH CH CH Π 2,4-bis(trifluoromethyl)phenyl 1-349 4-methylbenzene CH CH CH CH HH 2,4-bis(trifluoromethyl) 1-350 4-ethylphenyl CH CH CH H H 2,4-bis(trimethyl)phenyl 1-351 3-decyloxyphenyl CH CH CH CH HH 2,4-double (three Gas methyl)phenyl 1-352 4-decyloxyphenyl CH CH CH :CH HH 2,4·bis(trifluoromethyl)phenyl 1-353 354,5-trimethoxyphenyl CH CH CH [CH Π H 2,4-bis(trifluoromethyl)phenyl 1-354 1-naphthyl CH CH CE [CH :HH 2,4-bis(trifluoromethyl)phenyl 1-355 2-naphthalene CH CH CH [CH;HH 2,4-bis(trimethylsulfonyl)phenyl 80 200836629 Table 1 (19) Fossil number Qi α, 2 AV A% Ri r2 Q2 1-356 5-Ga-2-ϋ Benzenyl CH CH CH CH HH 2,4-bis(trifluoromethyl)phenyl 1-357 2-gas-3·11 specific hydrazide CH CH CHi CH HH 2,4-bis(trifluoromethyl) Phenyl 1-358 6-methyl-2-11 ratio sigma CH CH CH CH HH 2,4-bis(trimethyl)phenyl ' 1-359 5- gas-2-fluorene 12-based CH CH CH CH HH 2,4-bis(trifluoromethyl)phenyl 1-560 6-light-2-yl CH CH CH CH HH 2,4-bis(trifluoromethyl)phenyl 1-361 5 - 曱 base - ° ratio. Well-2-yl CH CH CH CH HH 2,4_bis(trifluoromethyl)phenyl 1-362 ϋ比耕-基CH CH CH CH HH 2,4-bis(tri-l-methyl) Phenyl 1-163 5-methyl-2-thienyl CH CH CH CH HH 2,4-bis(trimethyl)phenyl 1-364 3-methyl-2-thienyl CH CH CH CH HH 2 ,4-bis(trifluoromethyl)phenyl 1-365 phenyl CH CH CH HH 2,5-bis(trifluoromethyl)phenyl 1-366 phenyl CH CH CH HH 2-chloro·4 ,6-bis(trifluoromethyl)phenyl 1-367 2,6-difluorophenyl CH CH CH HH 2-chloro-4,6-bis(trimethyl)phenyl 1-368 4- Nitrophenyl CH CH CH CH HH 2-chloro-4,6-bis(trifluoromethyl)phenyl 1-369 phenyl CH CH CH CH H Π 2-bromoindole-4-(trifluoromethane Sulfomethoxy)phenyl 1-370 2-fluorophenyl CH CH CH HH 2_bromo-6-fluorenyl winter (trifluorodecanesulfooxy)phenyl 1-371 phenyl CH CH CH CH HH 2-Chloro-6-mercapto-4-(dioxamethoate xanthyloxy)phenyl 1-327 phenyl CH CH CH CE [HH 2_methyl_4-(trifluoromethanesulfonyloxy) Phenyl 1-373 phenyl CH CE CH CB [HH 4-(seven isopropyl)-2-indenyl 1-734 2-fluorophenyl CH CH : CH CE HH 4-(heptafluoroiso) Propyl)-2-methylnaphthyl 1-375 Group 1 CH CB: CH: ct H H 7- heptafluoroisopropyl two Yun-inden-4-yl 81
ItMj 編號 Qi AV A,4: Ri r2 q2 1-376 苯基 CH CH< CH CH H H 2,6-二氯-4-五氟硫烷基苯基 1-377 苯基 CH CH( CH CH H H 4-(3,4-二氟苯基)-2,6-二甲基苯基 1-378 苯基 CH CH丨 CH CH H H 4-(4-氣-3-甲基苯基)-2,6-二甲基苯基 1-379 苯基 CH CH CH CH H H 4-(咬喃-3-基)-2,6-二甲基苯基 1-380 2-氯苯基 CH CH CH CH H H 2,6-二曱基-4-(°塞口分-2_基)苯基^ 1-381 2-氯苯基 CH CH CH CH H H 2,6-二甲基-4-(ϋ塞吩-3-基)苯基 1-382 苯基 CH CH CH CH H H 2,6-二>臭-4-5哀己基苯基 1-383 苯基 CH CH CH CH H H 4-環己基苯基 1-384 苯基 CH CH CH CH H H 2,6-二曱基-4-(五氟丙醯基)苯基 1-385 苯基 CH CH CH CH H H 4-(七氟丁醯基)-2,6-二甲基苯基 1-386 苯基 CH CH CH CH H H 2,6-二曱基-4-(2,2,2-二氣-1-二氣甲基 乙基)苯基 1-387 苯基 CH CH CH CH H H 2->臭-6-(2,2,2-二氣-1-二1甲基乙氧基) °比°定-3-基 1-388 苯基 CH CH CH CH H H 2,2,3,3,4,4,4-七氟丁基 1-389 苯基 CH CH CH CH H H 2,2,3,3,3-五氟丙基 1-390 苯基 CH CH CH [CH :H H 2,4,6-二漠-3-七貌丙基硫苯基 1-391 2-氣。比咬-3-基 CH CH CH [CH ;H H 2,4,6-二>臭-3-七亂丙基硫苯基 1-392 2-氣苯基 CH CH CH [CH L H H 2,4,6_二〉臭-3-七氟t丙基硫苯基 1-393 2-亂苯基 CH CH :CE [CH [H H 4-二氣甲基硫苯基 1,394 2-氟苯基 CH ;CH :CE [CE [H H 4-三氟甲基磺醯基苯基 1-395 苯基 CH [CH iCE ICE [H H 4-七氣丙基疏苯基 200836629 表 1(20) 82 200836629 表 1(21) 編號 Qi A5! a’2 A A,4 Ri r2 _________—-^— ___q2 1-396 笨基 CH CH CH CH H H 1-397 笨基 CH CH CH CH H H -----队,、1 丰舉 ------ ---- 4*七it丙某石n ψ装贫甘 1-398 4«笨基 CH CH CH CH Me Me ----- ^ 瓜二 τ __ 本七氟丙基磺醢基1其 1-399 2-氟笨基 CH CH CH CH H H — ---------—--- —硫-2-甲基笨某 1-400 苯基 CH CH CH CH H H 4-甲基邻兑三氟-μ三氟甲基七細 口比口定-3-基 1401 2邀笨基 CH CH CH CH H H 丰曱基邻总三氟4-三氟甲基_乙細 口比咬-3-基 1402 2-氟苯基 CH CH CH CH H H 2„2Ά三氟-1-三氟曱基》乙細 咖定各基 1-403 苯基 CH CH CH CH H H 4«{2又2-三氟-1·(三氟甲基> 乙氧基比唆各基 1404 2-氟苯基 CH CH CH CH H H 三氣-1«(三氟曱基μ乙氧基}咖定各基 1-405 苯基 CH CH CH CH H H 2,本二溴各三氟甲氧基笨基 1-406 2-氟苯基 CH CH CH CH H H J-------—1 ~ ---—- 2+夂溴-6»三氟甲氧美笑1 L 4-石肖基苯基 CH CH CH CH H H 2,4^漠》6^氟曱氧基苯基 i-408 苯基 CH CH CH CH H H 心溴-6«三氟曱氧基苯基 1屬9 2,本二氟苯基 CH CH CH CH H H 2,Φ二溴心三氟甲某装某 1410 苯基 CH CH CH CH H H 2,4· 一溴-6·{七氟丙基硫)苯基 1411 2-1苯基 CH CH CH CH H H 2,Φ二溴各(七氟丙基疏)苯基 1412 丰硝基苯基 CH CH CH CH H H 2斗二溴各(七氟丙基硫)苯基 1-413 苯基 CH CH CH CH H H 2,4«二溴》6·{九氟丁基硫;)苯基 1414 2-氟苯基 CH CH CH • CH H H 2-溴4»氯4三氟甲基苯基 1415 苯基 CH CH CH :CH H H 2-溴冬氯-6«三氟甲基苯基 83 200836629 表 1(22) 編號 Qi A5! a,2 A,3 AV Ri r2 q2 1-416 2-氟苯基 ΟΠί CH CH CH H H 2-溴-6-氯-4-三氟曱基苯基 1-417 苯基 CH CH CH CH H H 4->臭-2-氯-6-二氟曱基苯基 1-418 2,6-二氣苯基 CH CH CH CH H H 4->臭-2-氣-6-二氣甲基苯基 1-419 苯基 CH CH CH CH H H 2->臭-4-1-6-三氣甲基苯基 1-420 苯基 CH CH CH CH H H 4-氟-6-三氟甲基苯基 1-421 2-埃苯基 CH CH CH CH H H 4-七氟i異丙基-2-曱基苯基 1-422 苯基 CH CH CH CH H H 2-第二丁基-4-七氟異丙基苯基 1-423 苯基 CH CH CH CH H H 2-鼠-4-七氣異丙基苯基 1-424 2-氟苯基 CH CH CH CH H H 4-七氟異丙基苯基 1-425 苯基 CH CH CH CH H H 2-甲烧石黃酿基-4-七氣異丙基苯基 1-426 4-硝基苯基 CH CH CH CH H H 2-甲烧石黃酿基-4-七氣異丙基苯基 1-427 苯基 CH CH CH CH H H 2,6-二溴-4-三氟甲基苯基 1-428 2-氟苯基 CH CH CH CH H H 2,6-二漠-4-二氟^甲基苯基 1-429 2,6-二氣苯基 CH CH CH CH H H 2,6-二>臭-4-二氟1甲基苯基 1-430 苯基 CH CH CH CH H H 2,6-二氯-4-(2,2,3,3,3-五氟丙氧基)苯基 1-431 2-氟苯基 CH CH CH CH H H 2,6-二氯-4-(2,2,3,3,3-五氟丙氧基)苯基 1-432 苯基 CH CH CH CH H H 2-甲基·4-(2又2-三氟乙氧基)苯基 1-433 2-氯吼°定-3-基 CH CH CH CH H H 2,6-二氯-4-(2,2,3,3,3-五氟丙氧基)苯基 1-434 苯基 CH CH :CH CH H H 2,6-二甲基-4-(2-氣-2,2-二亂-1_ (氯二氟甲基)-1-羥乙基)苯基 1-435 苯基 CH CH [CH CH H H 2,6-二甲基-4-(2,2,2-二氟-1-二氟甲基 -1-甲氧基)苯基 84 200836629 表 1(23) 化 編號 Qi A、 A,2 A,3 A,4 Ri r2 q2 1-436 2-氣苯基 CH CH CH CH H H 2,6-二曱基-4-(2,2,2-三氟-1-三氟曱基小甲 氧基)苯基 1-437 苯基 CH CH CH CH H H 2,6-二氯-4-三氟甲氧基苯基 1-438 苯基 CH CH CH CH H H 2-甲基-4-二氟甲氧基苯基 1-439 笨基 CH CH CH CH H H 5-石肖基°比淀-2-基 1-440 苯基 CH CH CH CH H H 5-氯吼啶-2-基 1-441 苯基 CH CH CH CH H H 4-甲基-6-(七氣異丙基)-。比°定-3-基 1-442 苯基 CH CH CH CH H H 3-氣-5-二氣曱基σ比σ定-·2-基 1-443 苯基 CH CH CH CH H H 5-七鼠異丙基-2·甲氧戴基-4-甲基σ塞吩-3-基 1-444 2-歡苯基 CH CH CH CH H H 5-七氟異丙基-2-甲氧羰基斗甲基噻吩-3-基 1-445 苯基 CH CH CH CH H H 2->臭-6-氣-4-甲基σ比σ定-3-基 1-446 苯基 CH CH CH CH H H 2,6-二甲基-4-三氟甲基苯基 1-447 2-氟苯基 CH CH CH CH H H 2,6-二甲基-4-二氣甲基苯基 1-448 苯基 CH CH CH CH H H 4-三氟甲基苄基 1-449 苯基 CH CH CH CH H H 3-三氟甲基苄基 1-450 苯基 CH CH CH CH H TT 2-三氟曱基苄基 1-451 苯基 CH CH CH CH H H 4-墙基节基 1-452 苯基 CH CH CH CH H H 3,5-雙(三氟曱基)节基 1-453 苯基 CH CH CH CH H H 4-氣-2,6-二甲基苯基 1-454 苯基 CH CH CH CH H H 4-漠-2,6-二甲基苯基 1-455 苯基 CH CH CH CH :H H 4-埃-2,6-二甲基苯基 85 200836629 表 1(24) 化合物 編號 Qi A9! a,2 A,3 A,4 Ri: Q2 1-456 2,6-二敗苯基 CH CH CH CH H H 4-蛾-2,6-二甲基苯基 1-457 苯基 CH CH CH CH H H 4-氯-2-二氟^曱基苯基 1-458 苯基 CH CH CH CH H H 2-氯-6-二氟甲基苯基 1-459 苯基 CH CH CH CH H H 4-埃-2-二氣甲基苯基 1-460 苯基 CH CH CH CH H H 2-氣-4-蛾-6-甲基苯基 1-461 苯基 CH CH CH CH H H 2,6-二甲基苯基 1-462 苯基 CH CH CH CH H H 4-溴-2-曱基-5-三氟甲基-2H-吡唑-3-基 1-463 苯基 CH CH CH CH H H 2,3,5,6-四氟-4-三氟曱基苯基 1-464 苯基 CH CH CH CH H H 2,3,4,5,6-五氟苯基 1-465 2-氟苯基 CH CH CH CH H H 2,3,4-三氟苯基 1-466 2-說苯基 CH CH CH CH H H 4-三氟曱基苯基 1-467 2-亂苯基 CH CH CH CH H H 2->臭-4-二氣甲基苯基 1-468 苯基 CH CH CH CH H H 2-溴-6-氯-4-三氟甲基苯基 1-469 2-氣苯基 CH CH CH GH H H 2-三氟甲基苯基 1-470 苯基 CH CH CH CH H H 2,4-二氯-6-三氟甲基苯基 1-471 苯基 CH /^TT CH CH H H 2->臭-4-異丙基-6-二氣甲基苯基 1-472 2-氟苯基 CH CH CH CH H H 2-溴-4-異丙基-6-三氟甲基苯基 1-473 苯基 CH CH CH CH H H 4-(七氟異丙基羰基)苯基 1-474 苯基 CH CH CH CH H H 2-曱基-4-硝基苯基 1-475 苯基 CH CH CH CH H H 2,4-二氯苯基 86 200836629 表 1(25) 化合物 編號 Qi a,2 A,3 A,4 Ri r2 Q2 1-476 苯基 CH丨 CH CH CH H H 3-蛾-5-瑞基苯基 1-477 苯基 CH CH CH CH H H 2,6-二甲基-4-硝基苯基 1-478 苯基 CH CH CH CH H H 5-石肖基-2-。密σ定基 1-479 苯基 CH CH CH CH H H 1-480 苯基 CH CH CH CH H H 4-弟二丁基戴基氧-2-曱基苯基 1-481 苯基 CH CH CH CH H H 4-苯甲醯基氧-2-甲基苯基 1-482 苯基 CH CH CH CH H H 4-苯甲醯基氧-6-氯-2-甲基苯基 1-483 苯基 CH CH CH CH H H 6-氣-4-經基-2-曱基苯基 1-484 苯基 CH CH CH CH H H 2->臭-4-¾基-6-曱基苯基 1-485 苯基 CH CH CH CH H H 2-漠-6-甲基-4-(對甲苯績酿基氧)苯基 1-486 苯基 CH CH CH CH Me H 2,6-二 >臭-4-(°比洛°定-1 -缓基)苯基 1-487 苯基 CH CH CH CH Me H 2,6-二>臭-4-乙氧獄基苯基 1-488 苯基 CH CH CH CH H H 2,6-二氯-4-(2,5-二侧氧基-3,3,4,4-四氟吼略口定 -1-基)苯基 1-489 苯基 CH CH CH CH H H 2,6-二氣-4-(2,5-二側乳基°比嘻ϋ定-1-基)苯基 1-490 苯基 CH CH CH CH H H 2,6-二氯-4-(1,3-二側氧基異吲哚啉-2-基) 苯基 1-491 苯基 CH CH CH CH H H 苯并噻唑-2-基 1-492 苯基 CH CH [CH CH H H 苯并噻唑-6-基 1-493 苯基 CH CH [CH CH H H 6-氯苯并噻唑-2-基 1-494 苯基 CH CH [CH CH H H 5,6-二甲基苯并噻唑-2_基 1-495 苯基 CH CK [CH CH H H 6-甲氧基苯并噻唑-2-基 87 200836629 表 1(26) 化合物 編號 Qi a,2 A,3 A,4 Ri r2 q2 1-496 苯基 CH CH CH CH H H 5-氯苯并噚唑-2-基 1-497 苯基 CH CH CH CH H H 4,6-二溴-3H-苯并[d]咪唑-5-基 1-498 2-氣°比0定-3-基 CH CH CH CH H H 4,6-二溴-3H-苯并[d]咪唑-5-基 1-499 苯基 CH CH CH CH H H 唉琳-8-基 1-500 苯基 CH CH CH CH H H 喧嚇^-3-基 1-501 苯基 CH CH CH CH H H 異啥琳-1-基 1-502 苯基 CH CH CH CH H H 4-苯基偶氮本基 1-503 苯基 CH CH CH GH H H 4-苯基噻唑-2-基 1-504 苯基 CH CH CH CH H H 3-甲基異噻唑-5-基 1-505 苯基 CH CH CH CH H H 5-苯基-2H-吡唑-3-基 1-506 苯基 CH CH CH CH H H 苐-2-基 1-507 苯基 CH CH CH CH H H 9-侧氧基苐-2-基 1-508 苯基 CH CH CH CH H H 金剛烧-1-基 1-509 苯基 CH CH CH CH H H 金剛烷-2-基 1-510 苯基 CH CH CH CH H H 3H-異吲哚-1-基 Ι-5Π 苯基 CH CH CH CH 了 i H 2,6-二甲基嘧啶-4-基 1-512 苯基 CH CH CH CH H H 3,4-二氰基苯基 1-513 苯基 CH CH CH CH H H 5-甲基硫-1H-[1,2,4]三唑-3·基 1-514 苯基 CH CH CH CH Π H 5-漠嗟嗤-2-基 1-515 苯基 CH CH CH CH H H 4-甲基噻唑-2-基 88 200836629ItMj No. Qi AV A, 4: Ri r2 q2 1-376 Phenyl CH CH<CH CH HH 2,6-Dichloro-4-pentafluorosulfanylphenyl 1-377 Phenyl CH CH (CH CH HH 4 -(3,4-difluorophenyl)-2,6-dimethylphenyl 1-378 phenyl CH CH丨CH CH HH 4-(4-Ga-3-methylphenyl)-2,6 -Dimethylphenyl 1-379 phenyl CH CH CH HH 4-(N--3-yl)-2,6-dimethylphenyl 1-380 2-chlorophenyl CH CH CH CH HH 2 ,6-dimercapto-4-(° plug-in-2_yl)phenyl^ 1-381 2-chlorophenyl CH CH CH CH HH 2,6-dimethyl-4-(zesophene- 3-yl)phenyl 1-832 phenyl CH CH CH H H 2,6-di > odor-4-5 succinylphenyl 1-383 phenyl CH CH CH CH HH 4-cyclohexyl phenyl 1- 384 phenyl CH CH CH H H 2,6-dimercapto-4-(pentafluoropropenyl)phenyl 1-385 phenyl CH CH CH CH HH 4-(heptafluorobutylidene)-2,6-di Methylphenyl 1-386 phenyl CH CH CH H H 2,6-dimercapto-4-(2,2,2-diox-1-dimethylmethylethyl)phenyl 1-387 phenyl CH CH CH CH HH 2->Smelly-6-(2,2,2-diox-1-dimethylolethoxy) ° ratio -3-yl 1-388 phenyl CH CH CH CH HH 2,2,3,3,4,4,4-heptafluorobutyl 1-389 phenyl CH CH CH CH HH 2,2,3,3,3-pentafluoropropyl 1-390 phenyl CH CH CH [CH :HH 2,4,6-di-di--3-decyl propylthiophenyl 1-391 2-gas倍-3-基CH CH CH [CH ;HH 2,4,6-di> odor-3-septyl propyl phenyl 1-352 2- phenyl CH CH CH [CH LHH 2, 4,6_2>Smelly-3-heptafluorot-propylthiophenyl-1-93 2- disordered phenyl CH CH :CE [CH [HH 4-dimethylthiophenyl 1,394 2-fluorobenzene CH;CH:CE [CE [HH 4-trifluoromethylsulfonylphenyl 1-395 phenyl CH [CH iCE ICE [HH 4-heptylpropyl phenyl phenyl 200836629 Table 1 (20) 82 200836629 Table 1 (21) No. Qi A5! a'2 AA,4 Ri r2 _________—^^— ___q2 1-396 Stupid CH CH CH CH HH 1-397 Stupid CH CH CH CH HH ----- Team, , 1 Feng Feng ------ ---- 4 * seven it C a stone n ψ 甘 1-3 1-3 1-3 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Heptafluoropropylsulfonyl 1 is 1-99 2-fluoro-p-CH CH CH CH HH — --------------thio-2-methyl stupid 1-400 phenyl CH CH CH CH HH 4-methyl-neutral trifluoro-μ-trifluoromethyl seven-nose mouth ratio -3-yl 1401 2 invites stupid CH CH CH CH HH Methyl _ 乙 口 咬 -3- 基 基 基 1402 2-fluorophenyl CH CH CH H H 2 2 2 Ά trifluoro-1-trifluoromethyl 乙 细 咖 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- 1- HH 4 «{2 again 2-trifluoro-1·(trifluoromethyl) ethoxylated oxime 1404 2-fluorophenyl CH CH CH CH H three gas-1 « (trifluoromethyl thiophene b Ethyl} each group 1-405 phenyl CH CH CH H H 2, the present dibromo trifluoromethoxy stupid 1-406 2-fluorophenyl CH CH CH CH HH J------ -1~ ----- 2+夂Bromo-6»Trifluoromethoxy Appease 1 L 4-Shischyl Phenyl CH CH CH CH HH 2,4^漠》6^Fluoromethoxyphenyl i- 408 phenyl CH CH CH CH HH Heart bromine-6 «trifluoromethoxyphenyl 1 genus 9 2, the present difluorophenyl CH CH CH H H 2 2, Φ dibromocarditrifluoromethane, a certain 1410 phenyl CH CH CH CH HH 2,4·monobromo-6·{heptafluoropropylsulfide)phenyl 1411 2-1 phenyl CH CH CH HH 2, Φ dibromo(pentafluoropropyl)phenyl 1412丰nitrophenyl CH CH CH CH HH 2 piped dibromo (heptafluoropropyl thio) phenyl 1-413 phenyl CH CH CH CH HH 2,4 «dibromo 6·{nonafluorobutyl sulphate; Phenyl 1414 2-fluorophenyl CH CH CH • CH HH 2-bromo 4» chloro 4 trifluoromethyl Phenyl 1415 phenyl CH CH CH : CH HH 2-bromyl chloride-6 «trifluoromethylphenyl 83 200836629 Table 1 (22) No. Qi A5! a, 2 A, 3 AV Ri r2 q2 1-416 2 -fluorophenyl ΟΠ CH CH CH CH HH 2-bromo-6-chloro-4-trifluoromethylphenyl 1- phenyl phenyl CH CH CH HH 4-> odor-2-chloro-6-difluoroanthr Phenylphenyl 1-418 2,6-diphenylphenyl CH CH CH CH HH 4->Smelly-2-gas-6-dimethylphenyl 1-419 Phenyl CH CH CH CH HH 2-> ; stinky 4-1-6-trimethylphenylphenyl 1-420 phenyl CH CH CH CH HH 4-fluoro-6-trifluoromethylphenyl 1-421 2-Ethyl CH CH CH CH HH 4-heptafluoroi-isopropyl-2-mercaptophenyl 1-522 phenyl CH CH CH HH 2-t-butyl-4-heptafluoroisopropylphenyl 1-423 phenyl CH CH CH CH HH 2-murine-4-heven isopropylphenyl 1-424 2-fluorophenyl CH CH CH CH HH 4-heptafluoroisopropylphenyl 1-245 phenyl CH CH CH H H 2- Dioscorea-4-pyrrolidylphenyl 1-426 4-nitrophenyl CH CH CH CH HH 2-methyl sulphate yellow saponin-4-seven isopropyl phenyl 1-427 benzene CH CH CH CH HH 2,6-Dibromo-4-trifluoromethylphenyl 1-288 2-fluorophenyl CH CH CH CH HH 2,6-II- Fluoro[methylphenyl] 1-429 2,6-diphenylphenyl CH CH CH CH HH 2,6-di>odor-4-difluoro-1-methylphenyl 1-430 phenyl CH CH CH CH HH 2,6-Dichloro-4-(2,2,3,3,3-pentafluoropropoxy)phenyl 1-341 2-fluorophenyl CH CH CH CH HH 2,6-dichloro-4- (2,2,3,3,3-pentafluoropropoxy)phenyl 1-432 phenyl CH CH CH HH 2-methyl·4-(2,2-trifluoroethoxy)phenyl 1 -433 2-Chloropurine -3--3-CH CH CH CH HH 2,6-Dichloro-4-(2,2,3,3,3-pentafluoropropoxy)phenyl 1-344 phenyl CH CH :CH CH HH 2,6-Dimethyl-4-(2-Gas-2,2-disorder-1_(chlorodifluoromethyl)-1-hydroxyethyl)phenyl 1-435 phenyl CH CH [CH CH HH 2,6-Dimethyl-4-(2,2,2-difluoro-1-difluoromethyl-1-methoxy)phenyl 84 200836629 Table 1 (23) Qi A, A, 2 A, 3 A, 4 Ri r2 q2 1-436 2-Phenylphenyl CH CH CH CH HH 2,6-Dimercapto-4-(2,2,2-trifluoro-1- Trifluoromethyl methoxy phenyl) 1-437 phenyl CH CH CH H H 2,6-dichloro-4-trifluoromethoxyphenyl 1-438 phenyl CH CH CH H H 2- Base-4-difluoromethoxyphenyl 1-439 stupyl CH CH CH CH HH 5-stone succinyl ratio butyl-2-yl 1-440 phenyl CH CH CH CH H H 5-Chloroisridin-2-yl 1-441 Phenyl CH CH CH CH H H 4-Methyl-6-(seven isopropyl)-. °定-3-基1-442 phenyl CH CH CH CH HH 3-气-5-二气曱 σ ratio σ定-·2-yl 1-443 phenyl CH CH CH H H 5-7 Isopropyl-2·methoxy-methoxy-4-methyl σ- thiophene-3-yl 1-444 2-phenylphenyl CH CH CH H H 5-heptafluoroisopropyl-2-methoxycarbonyl Thiophen-3-yl 1-4545 phenyl CH CH CH HH 2-> odor-6-gas-4-methyl σ ratio sigma-3-yl 1-446 phenyl CH CH CH H H 2 6-Dimethyl-4-trifluoromethylphenyl 1-475 2-fluorophenyl CH CH CH H H 2,6-Dimethyl-4-dimethylmethylphenyl 1-448 phenyl CH CH CH CH HH 4-trifluoromethylbenzyl 1-449 phenyl CH CH CH CH HH 3-trifluoromethylbenzyl 1-450 phenyl CH CH CH CH H TT 2-trifluorodecyl benzyl 1- 451 phenyl CH CH CH CH HH 4-wall base group 1-452 phenyl CH CH CH CH HH 3,5-bis(trifluoromethyl) group 1-453 phenyl CH CH CH H H 4- gas -2,6-Dimethylphenyl 1-454 phenyl CH CH CH CH HH 4- Desert-2,6-Dimethylphenyl 1-455 phenyl CH CH CH CH :HH 4-A-2, 6-Dimethylphenyl 85 200836629 Table 1 (24) Compound number Qi A9! a, 2 A, 3 A, 4 Ri: Q2 1-456 2,6-di-phenyl phenyl CH CH C H CH HH 4-Moth-2,6-Dimethylphenyl 1-457 phenyl CH CH CH H H 4-chloro-2-difluoropyridylphenyl 1-458 phenyl CH CH CH CH HH 2 -Chloro-6-difluoromethylphenyl 1-245 phenyl CH CH CH HH 4-E-2-dimethylphenyl 1-450 Phenyl CH CH CH CH HH 2-Galy-4-Moth -6-methylphenyl 1-461 phenyl CH CH CH CH HH 2,6-dimethylphenyl 1-462 phenyl CH CH CH CH HH 4-bromo-2-indolyl-5-trifluoromethyl -2H-pyrazol-3-yl 1-463 phenyl CH CH CH H H 2,3,5,6-tetrafluoro-4-trifluorodecylphenyl 1-424 phenyl CH CH CH CH HH 2 ,3,4,5,6-pentafluorophenyl 1-455 2-fluorophenyl CH CH CH H H 2,3,4-trifluorophenyl 1-446 2-Phenyl CH CH CH CH HH 4 -trifluoromethylphenyl 1-467 2-plex phenyl CH CH CH HH 2-> odor-4-dimethylphenyl 1-68 phenyl CH CH CH HH 2-bromo-6- Chloro-4-trifluoromethylphenyl 1-469 2-phenylphenyl CH CH CH GH HH 2-trifluoromethylphenyl 1-470 phenyl CH CH CH CH HH 2,4-dichloro-6- Trifluoromethylphenyl 1-471 phenyl CH /^TT CH CH HH 2->odor 4-isopropyl-6-dimethylphenyl 1-452 2-fluorophenyl CH CH CH CH HH 2-bromo-4-isopropyl-6-three Methylphenyl 1-473 phenyl CH CH CH H H 4-(heptafluoroisopropylcarbonyl)phenyl 1-444 phenyl CH CH CH CH HH 2-mercapto-4-nitrophenyl 1-475 Phenyl CH CH CH CH HH 2,4-dichlorophenyl 86 200836629 Table 1 (25) Compound number Qi a,2 A,3 A,4 Ri r2 Q2 1-476 Phenyl CH丨CH CH CH HH 3- Moth-5-renylphenyl 1-475 phenyl CH CH CH H H 2 2,6-dimethyl-4-nitrophenyl 1-478 phenyl CH CH CH CH HH 5-stone succinyl-2-. Σσ定基1-479 Phenyl CH CH CH CH HH 1-480 Phenyl CH CH CH CH HH 4-Dicylene Diyl Oxo-2-Mercaptophenyl 1-481 Phenyl CH CH CH CH HH 4 -benzimidyloxy-2-methylphenyl 1-482 phenyl CH CH CH HH 4-benzylideneoxy-6-chloro-2-methylphenyl 1-843 phenyl CH CH CH CH HH 6-gas-4-carbyl-2-mercaptophenyl 1-484 phenyl CH CH CH HH 2-> odor-4-3⁄4 -6-nonylphenyl 1-485 phenyl CH CH CH CH HH 2-Moline-6-Methyl-4-(p-toluene)-Phenyl 1-486 Phenyl CH CH CH CH Me H 2,6-II>Smelly-4-(°Bilo定定-1 - slow base) phenyl 1-287 phenyl CH CH CH CH Me H 2,6-di > odor-4-ethoxy phenyl phenyl 1-488 phenyl CH CH CH H H 2 6-Dichloro-4-(2,5-di-oxy-3,3,4,4-tetrafluoroanthracene-1-yl)phenyl 1-089 phenyl CH CH CH HH 2, 6-diqi-4-(2,5-di-l-butyl-based decyl-1-yl)phenyl 1-490 phenyl CH CH CH CH HH 2,6-dichloro-4-(1, 3-tertiaryoxyisoindoline-2-yl)phenyl 1-451 phenyl CH CH CH HH benzothiazol-2-yl 1-492 phenyl CH CH [CH CH HH benzothiazole-6 -Base 1-493 phenyl CH CH [CH CH HH 6-Chlorobenzothiazol-2-yl 1-494 phenyl CH CH [CH CH HH 5,6-dimethylbenzothiazole-2 yl 1-495 phenyl CH CK [CH CH HH 6-methoxy Benzothiazol-2-yl 87 200836629 Table 1 (26) Compound No. Qi a,2 A,3 A,4 Ri r2 q2 1-496 Phenyl CH CH CH CH HH 5-Chlorobenzoxazole-2- Base 1-197 phenyl CH CH CH H H 4 4,6-dibromo-3H-benzo[d]imidazol-5-yl-4-98 2-gas ratio 0 -3--3-CH CH CH CH HH 4 ,6-Dibromo-3H-benzo[d]imidazol-5-yl-4-99 phenyl CH CH CH CH HH 唉琳-8-yl 1-500 phenyl CH CH CH CH HH 喧Base 1-501 phenyl CH CH CH CH HH isoindolin-1-yl 1-502 phenyl CH CH CH CH HH 4-phenylazobenyl 1-503 phenyl CH CH GH HH 4-phenyl Thiazol-2-yl 1-504 phenyl CH CH CH CH HH 3-methylisothiazol-5-yl 1-505 phenyl CH CH CH CH HH 5-phenyl-2H-pyrazole-3-yl 1- 506 phenyl CH CH CH CH HH 苐-2-yl 1-507 phenyl CH CH CH H H 9 9-side oxime-2-yl 1-508 phenyl CH CH CH CH HH -509 phenyl CH CH CH CH HH adamantane-2-yl 1-510 phenyl CH CH CH CH HH 3H-isoindole-1-ylindole-5苯基 phenyl CH CH CH CH i H 2,6-dimethylpyrimidin-4-yl 1-512 phenyl CH CH CH HH 3,4-dicyanophenyl 1-513 phenyl CH CH CH CH HH 5-methylsulfur-1H-[1,2,4]triazol-3yl-1-part phenyl CH CH CH CH Π H 5- Desert-2-yl 1-515 Phenyl CH CH CH CH HH 4-methylthiazole-2-yl 88 200836629
89 200836629 表 1(28) 化谷物 編號 Qi Α' A、 A,3 A,4 Ri r2 q2 1-536 2-氟苯基 CH CH CH CH H H 2,6-二漠-4-丙基疏苯基 1-537 2-氣苯基 CH CH CH CH H H 2,6-二溴丙基磺醯基苯基 1-538 2-氟苯基 CH CH CH CH H H 2,6-二溴-4-丙基亞磺醯基苯基 1-539 2-氟^苯基 CH CH CH CH H H 2,6-二、/臭-4-苯基硫苯基 1-540 苯基 CH CH CH CH H H 2,6-二>臭-4-苯基硫本基 1_541 苯基 CH CH CH CH H H 2,6-二溴-4-(4-三氟甲基苯基甲基硫) 苯基 1-542 2-氟苯基 CH CH CH CH H H 2,6-二>臭-4-(4-二氣甲基苯基甲基硫) 苯基 1-543 2-氯0比°定-3-基 CH CH CH CH H H 2,6-二漠-4-(4-三氟曱基笨基甲基硫) 苯基 1-544 4-硝基苯基 CH CH CH CH H H 2,6-二溴-4-(4-三氟曱基苯基甲基硫) 苯基 1-545 4-氣苯基 CH CH CH CH H H 2,6-二>臭-4-(4-三敦甲基苯基甲基硫) 苯基 1-546 苯基 CH CH CH CH H H 2,6-二溴冬(2又2-三氟乙基硫)苯基 1-547 2-1苯基 CH CH CH CH H H 2,6-二>臭-4-(2,2,2-二氣乙基硫)苯基 1-548 2-氯0比°定-3-基 CH CH CH CH H H 2,6-二>臭-4-(2,2,2-二亂乙基硫)本基 1-549 4-硝基苯基 CH CH CH CH H H 2,6-二>臭-4-(2,2,2-二亂乙基硫)苯基 1-550 笨基 CH CH CH CH H H 2,6-二氣-4-頌基-未基 1-551 苯基 CH CH CH CH Me ,H 2,6-二氣-4-氣基-苯基 1-552 苯基 CH CH CH CH H H 4-胺基-2,6-二氯苯基 1-553 苯基 CH CH CB CE H H 4-氰基-1-曱基-3-(4-三氟曱基苯基) -1H-吡唑-5-基 1-554 苯基 CH CH CH CH H H 4-乙醯基胺基-2,6-二氯苯基 1-555 苯基 CH CH CH [CE H H 4-苯甲酿基胺基-2,6-二氯苯基 90 200836629 表 1(29) 不匕奋物 編號 Qi A," 乂,4: Ri q2 1-556 苯基 CH :H( zm ^e: H 2,6«二漠4甲基胺甲醯基苯基 1-557 苯基 CH CH< 3H( CH H H K3-氯-5-三氟曱基你定-2-基)斗氰基 -1Η-口米哇》5_基 1-558 2-氯吼啶:基 CH CHI CHI CH H H 4»氰基-1-甲基坐-5-基 1-559 氟苯基 CHi CHi CH丨 CH H H 丰氰基-1-甲基-ΙΗ-岭坐各基 1-560 笨基 CH CH CH CH H H 本亂基-I-第二丁基ΊΗ-σ比11 坐~5-基 1-561 苯基 CH CH CH CH H H 丰甲基各(七氟異丙基)苯并[d]嗟嗤-2-基 1-562 苯基 CH CH CH CH H H 丰甲基-6<Φ三氟甲基苯基比嗤-5-基 1-563 苯基 CH CH CH CH Me H 2,6·二漠 1-564 苯基 CH CH CH CH Me H 2,孓二溴竭嗤4基)苯基 1-565 苯基 CH CH CH CH H H 2,6-二溴4<U3-嗟二嗤4»基)苯基 1-566 苯基 CH CH CH cri H H 本七氟異丙基-2-經基各甲基苯基 1-567 苯基 CH CH CH CH Me H ‘七氟異丙基·2-經基各曱基苯基 1-568 苯基 CH CH CH CH Me H 丰七氣異丙基-2-甲焼續醯基氧各甲基苯基 1-569 苯基 CH CH CH CH Me T: 丰七氟異丙基-2-三氟甲烧磺醯基氧 各曱基苯基 1-570 苯基 CH CH CH CH :Me H 2-乙醯氧基车七Ιι異丙基各曱基苯基 1-571 苯基 CH CH CH CH [H H 本七氣異丙基:羥基曱基各曱基苯基 1-572 苯基 CH CH [CH CE [H H 丰七氟異丙基-2-甲氧基甲基各 甲絲基 1-573 苯基 CH CK [CE CE [H H 2-曱基硫曱基车七氟異丙基>6 -三氟曱基苯基 1-574 笨基 CH CE [Ct Cl·. E 2-溴各氯邻,5-二氯·定-2-基氧)苯基 上575 苯基 CH Cl· ICt Ct ΪΜ( 2-溴·4<3-氯-5-三氟甲基此。定-2-_ [各甲基苯基 91 200836629 表 1(30) 編號 1-576 Qi Α9! α’2 A,3 A’4 Ri Qi 笨基 CH CH CH CH H H 2-溴4-(3-氣>5-三氟甲基吨务2-基氧>6»甲基苯基 1-577 2-氟苯基 CH CH CH CH H H 2-漠4<3-氯-5-三氟甲基定-2-基氧甲基苯基 1-578 2,6-«—氣苯基 CH CH CH CH H H 2_漆4<3-氯-5-三氟甲基1 定-2-基氧>6·甲基苯基 1-579 2-氯·定-3-基 CH CH CH CH H H 2·溴冬(3-氯·5-三氟曱基吻定-2-基氧曱基苯基 1-580 苯基 CH CH CH CH Me H 2-氯邻,5-二氯吻定-2-基氧)苯基 1-581 笨基 CH CH CH CH H H 2-氯4{本氟苯基>»6«三氟甲基硫苯基 1-582 2-氯口比口定-3-基 苯基 CH CH CH CH H 2-氯·4<4·氟苯基)>6»三氟甲基硫苯基 __一—一 1-583 . 1-584 絲 CH CH CH CH H H Φ(2,Φ雙(三氟甲基)苯基>«2-氯各三氟曱基琉苯基 一苯基 CH CH CH CH Me H 4-(3,5-雙(三氟甲基yiH-Ab坐-1-基)《2,6"二溴苯基 1-585 ___—一 1-586 2-氣苯基 CH CH CH CH Me H Φ(3,5-雙(三氟甲基基>2,6·二溴苯基 2-氯口比口定各基 CH CH CH OH Me H Φ(3,5-雙(三氟甲基坐-1-基>2,6·二溴苯基 1-587 苯基 CH CH CH CH H H Φ(3,5-雙(三氟甲基>lH-u比嗤-μ基〇二漠笨基 1-588 ^——- 1-589 2-氟苯基 CH CH CH CH IH H :Φ(3,5-雙(三氟甲基)4Η比唾4-基>2,6«二溴笨基 2-氯口比σ定,3-基 CH CH CH CK IH H :4<3,5-雙(三氟甲基)41^比嗤4-;^>2,6»二溴苯基 4»氟苯基 CH CH :CH CE IH H [4>(3,5-雙(三氟甲基>1H-比哇》1-基)》2,6·二^苯基 92 200836629 表 1(31)89 200836629 Table 1 (28) Chemical grain number Qi Α' A, A, 3 A, 4 Ri r2 q2 1-536 2-fluorophenyl CH CH CH H H 2 2,6-II -4-propyl benzene 1-537 2-Phenylphenyl CH CH CH CH HH 2,6-Dibromopropylsulfonylphenyl 1-538 2-fluorophenyl CH CH CH CH HH 2,6-Dibromo-4-propenyl Isosulfonylphenyl 1-549 2-fluoro^phenyl CH CH CH H H 2,6-di,/odor 4-phenylthiophenyl 1-540 phenyl CH CH CH H H 2,6 -二>odor-4-phenylthiobenyl 1_541 phenyl CH CH CH CH HH 2,6-dibromo-4-(4-trifluoromethylphenylmethylsulfate)phenyl 1-542 2- Fluorophenyl CH CH CH CH HH 2,6-di>Smelly-4-(4-dimethylphenylmethylsulfide)phenyl 1-543 2-Chloro 0 to °-3-yl CH CH CH CH HH 2,6-II-4-(4-trifluorodecyl-phenylthio)phenyl 1-544 4-nitrophenyl CH CH CH CH HH 2,6-dibromo-4- (4-trifluoromethylphenylmethylsulfanyl)phenyl 1-545 4-phenylphenyl CH CH CH CH HH 2,6-di >Smelly-4-(4-Tritonmethylphenylmethyl) Sulfur) phenyl 1-546 phenyl CH CH CH H H 2,6-dibromodong (2 bis 2-trifluoroethyl thio)phenyl 1-547 2-1 phenyl CH CH CH H H 2,6 -two> stinky -4-(2,2,2- Gas ethyl thio)phenyl 1-548 2-chloro 0 to °-3-yl CH CH CH CH HH 2,6-di > odor-4-(2,2,2-disorganoethyl sulphate) 1-49 4-Nitrophenyl CH CH CH CH HH 2,6-di> Odor-4-(2,2,2-disorder ethylthio)phenyl 1-550 Styyl CH CH CH CH HH 2,6-diox-4-mercapto-unsupplied 1-451 phenyl CH CH CH CH Me ,H 2,6-diox-4-yl-phenyl-1-552 phenyl CH CH CH CH HH 4-Amino-2,6-dichlorophenyl 1-553 phenyl CH CH CB CE HH 4-cyano-1-indolyl-3-(4-trifluorodecylphenyl)-1H- Pyrazol-5-yl 1-554 phenyl CH CH CH CH H 4- 4-decylamino-2,6-dichlorophenyl 1-255 phenyl CH CH CH [CE HH 4-Benzyl hexylamine Base-2,6-dichlorophenyl 90 200836629 Table 1 (29) No excitement number Qi A," 乂,4: Ri q2 1-556 phenyl CH :H( zm ^e: H 2,6 «二漠4methylamine-methylphenylphenyl 1-557 phenyl CH CH< 3H(CH HH K3-chloro-5-trifluoromethylidene-2-yl)pipecyano-1Η-Mimi 》5_基1-558 2-chloroacridine: base CH CHI CHI CH HH 4» cyano-1-methyl sit-5-yl 1-559 fluorophenyl CHi CHi CH丨CH HH cyano cyano-1 -Methyl-ΙΗ-ridge sitting on each base 1-560 CH CH CH CH HH This chaotic-I-second butyl ΊΗ-σ ratio 11 sits ~5-yl 1-561 phenyl CH CH CH CH HH hydroxymethyl each (heptafluoroisopropyl) benzo[ d] inden-2-yl 1-562 phenyl CH CH CH CH HH abundance methyl-6<Φ trifluoromethylphenylpyridin-5-yl 1-536 phenyl CH CH CH Me Me 2, 6·二漠1-564 phenyl CH CH CH Me H 2, 孓 dibromo 嗤 4 )) phenyl 1-565 phenyl CH CH CH CH HH 2,6-dibromo 4<U3-嗟二嗤4»yl)phenyl 1-536 phenyl CH CH CH cri HH heptafluoroisopropyl-2-carbylmethylphenyl 1-567 phenyl CH CH CH CH Me H 'heptafluoroisopropyl 2-Phenyl-p-phenylphenyl 1-568 phenyl CH CH CH CH H 七七气isopropyl-2-methyl hydrazine 醯 氧 氧 各 each 1-methyl phenyl 1-69 phenyl CH CH CH CH Me T: sevoflurane isopropyl-2-trifluoromethanesulfonyloxyl decylphenyl 1-570 phenyl CH CH CH CH :Me H 2-ethyloxy car Ι Ι isopropyl 曱Phenylphenyl 1-571 phenyl CH CH CH CH [HH Benqi isopropyl: hydroxy fluorenyl decyl phenyl 1-572 phenyl CH CH [CH CE [HH hexafluoroisopropyl-2- Methoxymethylmethylmethyl 1-753 phenyl CH CK [CE C E [HH 2-mercaptopurine-based heptafluoroisopropyl>6-trifluorodecylphenyl 1-574 stupyl CH CE [Ct Cl·. E 2-bromochloro-, 5-dichloro · Benz-2-yloxy)phenyl on 575 phenyl CH Cl · ICt Ct ΪΜ (2-bromo·4<3-chloro-5-trifluoromethyl.定-2-_ [Each methylphenyl 91 200836629 Table 1 (30) No. 1-576 Qi Α9! α'2 A,3 A'4 Ri Qi Stupid CH CH CH CH HH 2-Bromo 4-(3 -gas>5-trifluoromethyltonene 2-yloxy>6»methylphenyl 1-577 2-fluorophenyl CH CH CH HH 2- desert 4 <3-chloro-5-trifluoro Methyl-den-2-yloxymethylphenyl 1-577 2,6-«-gas phenyl CH CH CH H H 2 2 lacquer 4 <3-chloro-5-trifluoromethyl 1 1,4-yl Oxygen>6-methylphenyl 1-475 2-chloro-di--3-yl CH CH CH CH HH 2·bromo-t-(3-chloro·5-trifluorodecyl-butenyl-2-yloxycarbonyl) Phenyl 1-580 phenyl CH CH CH CH H H 2-chloro-, 5-dichloro-butoxy-2-yloxy)phenyl 1-581 stupyl CH CH CH CH HH 2-chloro 4{benzobenzene Base>»6 «trifluoromethylthiophenyl 1-582 2-chloro port specific -3--3-phenylphenyl CH CH CH H 2-chloro·4<4·fluorophenyl)>6» Trifluoromethylthiophenyl__一一一1-583. 1-584 Silk CH CH CH CH HH Φ(2,Φbis(trifluoromethyl)phenyl>«2-chlorotrifluoromethyl琉Phenyl-phenyl CH CH CH CH Me H 4-(3,5-bis(trifluoromethylyiH-Ab sitting-1-yl) "2,6"Dibromophenyl 1-85 ___—1 -586 2-Phenylphenyl CH CH CH CH Me H Φ( 3,5-bis(trifluoromethyl)>2,6·dibromophenyl 2-chloro-oryl group CH CH CH OH Me H Φ(3,5-bis(trifluoromethyl-seat- 1-based>2,6·dibromophenyl 1-587 phenyl CH CH CH HH Φ(3,5-bis(trifluoromethyl)<lH-u 嗤-μ 〇 漠 漠 漠 漠1-588 ^——- 1-589 2-fluorophenyl CH CH CH IH H : Φ(3,5-bis(trifluoromethyl)4Η is more than salivary 4-based>2,6«dibromo Base 2-Chloroport ratio σ, 3-based CH CH CH CK IH H : 4 < 3,5-bis(trifluoromethyl)41^ than 嗤4-;^>2,6»dibromophenyl 4»fluorophenyl CH CH :CH CE IH H [4>(3,5-bis(trifluoromethyl>1H-byw) 1-base) 2,6·di^phenyl 92 200836629 Table 1 (31)
化合物 編號 Qi Α5! a,2 A,3 A’4 Ri r2 q2 1-591 苯基 CH CH CH丨 CH Me H ‘ K3,5-雙(三氟曱基>1H』比嗤冬基>2斤二氯苯基 1-592 苯基 CH CH CH CH H H 4<3,5-雙(三氟曱基>1Η-♦坐-1-基曱基) -2->臭~6~甲基本基 1-593 2-氟苯基 CH CH CH CH H H Φ(3,5-雙(三氟甲基)4H^b嗤4-基甲基) -2-溴各甲基苯基 1-594 2-氯吼口定-3-基 CH CH CH CH H H Φ(3,5-雙(三氟甲基)4H-u比嗤4-基甲基) -2->臭~6~曱基苯基 1-595 苯基 CH CH CH CH Me H Φ(3,5-雙(三氟甲基坐4-基甲基) -2->臭-6-甲基苯基 1-596 苯基 CH CH CH CH H H 5-溴-7«(七氟異丙基h2,3-二IrlH-茚斗基 1-597 2-1苯基 CH CH CH CH H H 5-溴-7·(七|L異丙基>2,3-二氫4H射基 1-598 苯基 CH CH CH CH H H 5-氯-7-(七氟異丙基)-2,3-二氫-1H-印4·基 1-599 2-氟苯基 CH CH CH CH H H 5-氯-7·(七氣異丙基)-2,3_二氮-1H-讳*4·基 1-600 2-氣苯基 ca [CH CH CH [Me H 丰甲基各{2之> 三氟τΚ三氟甲基)乙氧基} 口比口定-3-;^ 1-601 苯基 CF CH CH CF H TJ 4-七氟異丙基-2-甲基苯基 1-602 笨基 ca [CH CH ;CH [H H 2,4·雙(三氟甲基)苯基 1-603 2-氟苯基 CH CH CH [CK [H Me 4-七氣異丙基·2-甲基石黃醢基苯基 1-604 苯基 CE [CH CE [CF [H n-Bi 3 2-弟二丁基4·七鼠異丙基苯基 1-605 苯基 CB [CH CB [Cl· I H H 2-氯-6·二氣曱基硫苯基 93 200836629 表 2(1) 化Ϋ物 編號 Qi a,2 A,3 A,4] R4] q2 2-1 苯基 CH CH丨 CH CH H H: 2,6·二溴-4-(151,2,3,3,3-六氟丙氧基)苯基 2-2 2-甲基苯基 CH CH CH CH H H: 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-3 3-甲基苯基 CH CH CH CH H H: 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)笨基 2-4 4-曱基苯基 CH CH CH CH H H: 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-5 2-乙基苯基 CH CH CH CH H H 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-6 3-乙基苯基 CH CH CH CH H H 2,6-二溴-4-(l,l,2,3,3,3-六氟丙氧基)苯基 2-7 4-乙基苯基 CH CH CH CH H H 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-8 2-氟苯基 CH CH CH CH H H 2,6-二溴冬(1,1,2,3,3,3-六氟丙氧基)苯基 2-9 3-氟苯基 CH CH CH CH H H 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-10 4-氣苯基 CH CH CH CH H H 2,6-二溴冰(1,1,2,3,3,3-六氟丙氧基)苯基 2-11 2-氯苯基 CH CH CH CH H H 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-12 3-氯苯基 CH CH CH CH H H 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-13 4-氯苯基 CH CH CH CH H H 2,6-二溴冬(1,1,2,3,3,3-六氟丙氧基)笨基 2-14 2-溴苯基 CH CH CH CH H H 2,6-二溴冰(1,1,2,3,3,3-六氟丙氧基)苯基 2-15 3->臭苯基 CH CH CH CH H H 2,6-二漠-4-(1,1,2,3,3,3-六氣丙氧基)苯基 246 4-溴苯基 CH CH CB CH H H 2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-17 2-埃苯基 CH CH CH [CH H H 2,6-二溴;-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-18 3-球·本基 CH CH CH [CH H H 2,6-二漠-4-(1,1,2,3,3,3-六氣丙氧基)苯基 2-19 4-碘苯基 CH CH CH [CH :H H :2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 2-20 3-氰基苯基 CH CH CE [CH ;H :2,6-二溴-4-(1,1,2,3,3,3-六氟丙氧基)苯基 94 200836629 表 2(2) 化 編號 Qi A5! A’2 A、 Μ Ri r2 —----- q2 2-21 4-氰基苯基 CH CH CH CH H H —--- 2,6·二溴4(1,1?2,353,3-六氟丙拳華)笨某 2-22 2-硝基苯基 CH CH CH CH H H 2,6»二溴》4<1,1?2,33,3-六氟丙氧甚後| 2-23 3-石肖基 CH CH CH CH H H 2,6«二溴4{1,1523,33-六氟丙拳菩样苍 2-24 丰硝基苯基 CH CH CH CH H H 2,6·—备车^幻^-六氟丙攀基作基 2-25 2-胺基苯基 CH CH CH CH H H --------— 2’6~—溴-4-(1,1^233,3-六氟丙章其偉其 2-26 2-27 3-胺基苯基 CH CH CH CH H H 又3,3,3-六^氧基)苹甚 丰胺基苯基 CH CH CH CH H H 二溴-4-(1,152,3,3,3-六貌丙梟其、f 装 2-28 2-三氟曱基苯基 CH CH CH CH H H 2,&二漠-4^142333-六氟丙龛其作其 2-29 3-三氟甲基苯基 CH CH CH CH H H 二溴·4>(1,1又3,3,3-六氣雨g其、学苠 2-30 4*三氟甲基苯基 CH CH CH CH H H 2,6-—》臭-4-(1,1 ^23,3,3-六翕 1¾ 备 1、也盆 2-31 2-經基苯基 CH CH CH CH H H 2方"二溪4·(1,ΐ52,3,3,3-六氟雨童其從其 2-32 2-曱氧基苯基 CH CH CH CH H H 2,6-二溴4-(1,1^2333-六氟而毚其從其 2-33 3-曱氧基苯基 CH CH CH CH H H 2,6-二溴4-(1,1^23,3}六氟而惫其读其 2-34 丰甲氧基苯基 CH CH CH CH H H 2,6-二溴-4"(1,1又3,3,3-六氟而毚其從其 2-35 2-苯氧基苯基 CH CH CH CH H H 二漠4-(1,1?2,3,3,3-六氣丙龛其信其 2-36 二曱基乙基) 苯基 CH CH CH CH H H 256-—/^4-(1,1^333-7^¾ a 2-37 3仁曱紐基) 苯基 CH CH CH :CH H H 2,6-二漠-4-(1,152,3,3,3-六_ _2-38 4·(二曱細基) 苯基 CH CH CE [CH H H _ 1二漠」μ(ΐ,1又3,3,3-:^龜而氧基)笨基 2-39 夂三氟甲氧基苯基 lOH CH CH [CE [H H 2,6-二漠-4-(1,1^2333-六氤丙®其^笑其 2-40 2仏醯基胺基) 苯基 |ck [CH CF ICE [H H 三漠 95 200836629 表 2(3) 編號 Qi Α?! a,2 A,3 A54 Ri r2 q2 241 3·{乙基)苯基 CH CH CH CH H H ------ 2,6»二溴4-(1,1?2,3,33-六氟丙氧基)苯基 242 丰(乙醯基胺基)苯基 CF CH CH CH H H 243 2-乙酸氧基笨基 CH CH CH CH H H 2,6«二漠斗(1,1?2,3,3,3-六氟丙荜甚)帑萃 244 2~(甲基)苯基 CH CH CH CH H H 2,6»二漠-4{1,1?2,3,3,3-六氟丙氧甚)苹甚 245 4"(甲氧戴基)苯基 CH CH CH CH H H 决工溴冬⑽幻^-六氟丙拳勤苹甚 246 23-二甲基苯基 CH CH CH CH H H 2,6·二漠3,3,3-六氤丙 _ 甚)帑苹 247 2,Φ二曱基苯基 CH CH CH CH H H 2,6»二溴斗(1,1?2,3,33-六氟丙氧基)苹基 248 2,6>二甲基苯基 CH CH CH CH H H 2,6»二漠4{1,1?2,3,3,3-六氟丙筚签)芊签 249 2,3-二氟苯基 CH CH CH CH H H 2,6> 二漠 4"(1,1?2,3,3,3-六氟丙|[甚)窄菴 2-50 2,‘二氟苯基 CH CH CH CH H H 2,6二溴·Φ(1,1又333-六氟丙奉基)羊基 2-51 2,5-二氟苯基 CH CH CH CH H H 2,6»二漠4<1,1?2,3,3,3-六氟丙筚莘)苹苹 2-52 2夺二氟苯基 CH CH CH CH H H 2,孚一>臭冬(1,152,3,3,3-六氟丙_基)掌甚 2-53 3,Φ二氟苯基 CH CH CH CH H H 2,6-—>臭4-(1,152,3,3,3-六氟丙氣基)笨墓 2-54 3>二氟苯基 CH CH CH CH H H 2,卜二溴4(1,1又3,3,3-六氟丙攀妇节荃 2-55 2,3-二氯苯基 CH CH CH CH H H 2,6-—漠4-(1,1523,3,3-六鼠丙氣基)苹基 2-56 2,4-二氯苯基 CH CH CH CH H H 2,6»二溴《4<1,1又3,3,3-六氟丙攀签)苄荃 2-57 2》二氯笨基 CH CH CH CH H H 2,6-—溪4-(1,152,3,3,3-六鼠丙氧某^笨某 2-58 2,孓二氯苯基 CH CH CH :OH H H 2,6*二溪4<1,1?2,3,3,3-六氟丙|1签)节签 2-59 3,4«二氯苯基 CH CH CH LCE [H H 六氟兩拏签)苹签 2-60 肖基苯基 CH :CH CH [OH [H H ---—----- 2介一/臭'车(W又3,3,3_六氟丙氧基)苯基 96 200836629 表次4) <匕為勿 編號 Qi a,2 A53 A54 Ri r2 Q2 2-61 肖基苯基 CH CH CH< CH H H 2,6>二溴4(1,1?2,3,3,3-六氟丙氧基)苯基 2-62 2,6·二甲氧基苯基 CH CH CH丨 CH H H 2,6«二溴车(1,1又3,3,3-六氟丙氧基)苯基 2-63 3>二甲氧基苯基 CH CH CH CH H H 2,6>二溴4-(1,123,33-六氟丙氧基)苯基 2-64 3-甲基4»硝基苯基 CH CH CH CH H H 2,孚二漠1(1,1?2,3,3,3-六氟丙氧羞)苯基 2-65 5-胺基-2-氣苯基 CH CH CH CH H H 2,6·二溴4(1,1^23,33-六氟丙氧基)苯基 2-66 3-氟-2-曱基苯基 CH CH CH CH H H 2,6·二溴1(1,1?2,3,3,3-六氟丙_苯基 2-67 2-氟-5-石肖基苯基 CH CH CH CH H H 2,6«二溴>4{1,1?2,3,3,3-六氟丙氧基)苯基 2-68 4-敦-3-石肖基苯基 CH CH CH CH H H 2,6-二溴4<1,1?2,33,3-六氟丙氧基)苯基 2-69 5-氣-2-石肖基苯基 CH CH CH CH H H 2,6«二溴》4<1,1;2,3,3,3-六氟丙氧基)苯基 2-70 2-氣-6-蛾苯基 CH CH CH CH H H 2,6·二溴4C1,U3,33-六氟丙氧基)笨基 2-71 2-氟-5-二1甲基苯基 CH CH CH CH H H 2,6·二溴1(1,1?2,3,3,3-六氟丙氧基)苯基 2-72 2-氯-4·石肖基苯基 CH CH CH CH H H 2斤二溴4<1,1又3,33-六氟丙氧基)苯基 2-73 2-氯·4~亂苯基 GH CH CH CH H H 2,6-二溴六氟丙氧基)苯基 2-74 2-氯-6·氣苯基 CH CH CH CH H H 2,6·二溴4<1,1又3,3,3-六氟丙氧基)苯基 2-75 3,氯-4-象苯基 CH CH CH [OH H H 2,6>二溴斗(1,1^2333-六氟丙氧基)苯基 2-76 4-氯-2-1苯基 CH CH CH CH H H 2,6»二漠冬(1,1?2,3,33-六氟丙氧基)苯基 2-77 4»氯-2-石肖基苯基 CH CH CE [CE I H H 2,6·二溴4<1,1?2,353,3-六氟丙氧基)苯基 2-78 3-曱氧基车石肖基苯基 :CH ;CH [CE ICF. I H H 2,6·二溴冬(1,1?2,3,3,3-六氟丙氧1)苯基 2-79 2-甲氧基4«瑞基苯遵 ,CH [CE [a ICF I H H 2,6»二漠4(1,12333-六氟丙氧基)苯基 2-80 2,3,4«三氟苯基 CE [CH [a Id I H H 2,6·二溴4<1,U3,3,3-六氟丙氧基)苯基 97 200836629 表 2(5)Compound No. Qi Α5! a,2 A,3 A'4 Ri r2 q2 1-591 Phenyl CH CH CH丨CH Me H ' K3,5-bis(trifluoromethyl hydrazone > 1H) than hydrazine base > 2 kg of dichlorophenyl 1-592 phenyl CH CH CH H H 4 <3,5-bis(trifluoromethyl)>1Η-♦sitting-1-ylindenyl) -2->Smelly~6~ Methyl group 1-593 2-fluorophenyl CH CH CH HH Φ(3,5-bis(trifluoromethyl)4H^b嗤4-ylmethyl)-2-bromomethylphenyl 1- 594 2-Chloropurine-3-yl CH CH CH CH HH Φ(3,5-bis(trifluoromethyl)4H-u 嗤4-ylmethyl)-2->Smelly~6~曱Phenylphenyl 1-95-phenyl CH CH CH CH Me H Φ(3,5-bis(trifluoromethyl-spin-4-ylmethyl)-2-> odor-6-methylphenyl 1-956 benzene CH CH CH CH HH 5-bromo-7«(heptafluoroisopropyl h2,3-di IrlH-indole group 1-597 2-1 phenyl CH CH CH CH HH 5-bromo-7·(seven | L-isopropyl>2,3-dihydro 4H-based 1-598 phenyl CH CH CH CH HH 5-chloro-7-(heptafluoroisopropyl)-2,3-dihydro-1H-imprint 4 ·Base 1-599 2-fluorophenyl CH CH CH CH HH 5-chloro-7·(seven isopropyl)-2,3_diazo-1H-讳*4·yl 1-600 2-benzene Base ca [CH CH CH [Me H 丰 methyl each {2>> trifluoro τΚ trifluoromethyl) ethoxy} Oral ratio -3-; ^ 1-601 phenyl CF CH CH CF T TJ 4-heptafluoroisopropyl-2-methylphenyl 1-602 stupid ca [CH CH ; CH [HH 2,4 Bis(trifluoromethyl)phenyl 1-603 2-fluorophenyl CH CH CH [CK [H Me 4-heptafluoroisopropyl 2-methyl fluorenylphenyl 1-604 phenyl CE [CH CE [CF [H n-Bi 3 2-dibutyl 4·heptazole isopropylphenyl 1-605 phenyl CB [CH CB [Cl· IHH 2-chloro-6·dimethyl thiophenyl) 93 200836629 Table 2(1) Chemical substance number Qi a,2 A,3 A,4] R4] q2 2-1 Phenyl CH CH丨CH CH HH: 2,6·Dibromo-4-(151,2 ,3,3,3-hexafluoropropoxy)phenyl 2-2 2-methylphenyl CH CH CH H HH: 2,6-dibromo-4-(1,1,2,3,3, 3-hexafluoropropoxy)phenyl2-3-3-methylphenyl CH CH CH H HH: 2,6-dibromo-4-(1,1,2,3,3,3-hexafluoropropyl Oxy)) 2-4 4-mercaptophenyl CH CH CH H H: 2,6-dibromo-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl 2-5 2-ethylphenyl CH CH CH H H 2 2,6-dibromo-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl 2-6 3-B Phenylphenyl CH CH CH CH HH 2,6-dibromo-4-(l,l,2,3,3,3-hexafluoropropoxy)phenyl 2-7 4-ethyl CH CH CH CH HH 2,6-Dibromo-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl 2-8 2-fluorophenyl CH CH CH H H 2 ,6-Dibromo-t-(1,1,2,3,3,3-hexafluoropropoxy)phenyl 2-9 3-fluorophenyl CH CH CH CH HH 2,6-dibromo-4-( 1,1,2,3,3,3-hexafluoropropoxy)phenyl 2-10 4-phenylphenyl CH CH CH CH HH 2,6-dibromo ice (1,1,2,3,3 ,3-hexafluoropropoxy)phenyl 2-11 2-chlorophenyl CH CH CH H H 2 2,6-dibromo-4-(1,1,2,3,3,3-hexafluoropropoxy Phenyl 2-12 3-chlorophenyl CH CH CH H H 2,6-dibromo-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl 2-13 4-Chlorophenyl CH CH CH CH HH 2,6-Dibromodong (1,1,2,3,3,3-hexafluoropropoxy) phenyl 2-14 2-bromophenyl CH CH CH CH HH 2,6-dibromo ice (1,1,2,3,3,3-hexafluoropropoxy)phenyl 2-15 3-> stinyl phenyl CH CH CH CH HH 2,6-two desert -4-(1,1,2,3,3,3-hexapropoxy)phenyl 246 4-bromophenyl CH CH CB CH HH 2,6-dibromo-4-(1,1,2 ,3,3,3-hexafluoropropoxy)phenyl 2-17 2-Ethyl CH CH CH [CH HH 2,6-dibromo;-4-(1,1,2,3,3, 3-hexafluoropropoxy)phenyl 2-18 3-sphere·local CH CH CH [CH HH 2,6-two desert-4-(1 ,1,2,3,3,3-hexapropoxy)phenyl 2-19 4-iodophenyl CH CH CH [CH :HH :2,6-dibromo-4-(1,1,2 ,3,3,3-hexafluoropropoxy)phenyl 2-20 3-cyanophenyl CH CH [CH ;H :2,6-dibromo-4-(1,1,2,3, 3,3-Hexafluoropropoxy)phenyl 94 200836629 Table 2(2) Chemical number Qi A5! A'2 A, Μ Ri r2 —----- q2 2-21 4-cyanophenyl CH CH CH CH HH —--- 2,6·dibromo 4 (1,1?2,353,3-hexafluoropropanol) stupid 2-22 2-nitrophenyl CH CH CH H H 2,6» two Bromine"4<1,1?2,33,3-hexafluoropropoxylate| 2-23 3-石肖基 CH CH CH CH HH 2,6«Dibromo 4{1,1523,33-hexafluoropropyl菩样苍2-24 nitrophenyl CH CH CH CH HH 2,6·—Carriage ^ Magic ^- hexafluoropropanyl base 2-25 2-Aminophenyl CH CH CH CH HH -- ------ 2'6~-Bromo-4-(1,1^233,3-hexafluoropropyl) Qi Weiqi 2-26 2-27 3-Aminophenyl CH CH CH H HH 3, 3,3-hexaoxy) acesulfame phenyl CH CH CH CH HH dibromo-4-(1,152,3,3,3-hexa-propionate, f 2-28 2-trifluoro Nonylphenyl CH CH CH CH HH 2, & Erm-4^142333-hexafluoropropionate as its 2-29 3-trifluoromethylbenzene CH CH CH CH HH Dibromo·4>(1,1,3,3,3-six gas rain g, 苠2-30 4*trifluoromethylphenyl CH CH CH H H 2,6-- 》臭-4-(1,1 ^23,3,3-六翕13⁄4 备1, also basin 2-31 2-Phenylphenyl CH CH CH CH HH 2方"二溪4·(1,ΐ52 , 3,3,3-hexafluoropond from its 2-32 2-decyloxyphenyl CH CH CH CH HH 2,6-dibromo 4-(1,1^2333-hexafluoro and its It is 2-33 3-decyloxyphenyl CH CH CH CH HH 2,6-dibromo 4-(1,1^23,3}hexafluoro and is read by its 2-34-fluorenyloxyphenyl CH CH CH CH HH 2,6-dibromo-4" (1,1 and 3,3,3-hexafluoro and 毚 from its 2-35 2-phenoxyphenyl CH CH CH H H (1,1?2,3,3,3-hexa-propion, its letter 2-36-didecylethyl) phenyl CH CH CH CH HH 256-—/^4-(1,1^333- 7^3⁄4 a 2-37 3 仁曱纽基) phenyl CH CH CH :CH HH 2,6-二漠-4-(1,152,3,3,3-六_ _2-38 4·(二曱细Phenyl CH CH CE [CH HH _ 1 二漠"μ(ΐ,1,3,3,3-:^ turtle and oxy) stupid 2-39 fluorene trifluoromethoxyphenyl lOH CH CH [CE [HH 2,6-二漠-4-(1,1^2333-六氤丙® its ^ laugh its 2-40 2 fluorenylamino) phenyl | ck [CH CF ICE [HH San Mo 95 200836629 Table 2 (3) No. Qi Α?! a, 2 A, 3 A54 Ri r2 q2 241 3·{Ethyl) phenyl CH CH CH CH HH ------ 2,6»dibromo 4-(1,1?2,3,33-hexafluoropropoxy)phenyl 242 abundance (acetamidoamine)phenyl CF CH CH CH HH 243 2-acetoxy CH CH CH CH H H 2,6 «Second Moist (1,1?2,3,3,3-hexafluoropropanol) extract 244 2~(methyl)phenyl CH CH CH CH HH 2, 6»二漠-4{1,1?2,3,3,3-hexafluoropropoxyphene) 245 4"(methoxylatyl)phenyl CH CH CH CH HH bromine winter (10) magic ^ - Hexafluoropropyl fistula 246 23-dimethylphenyl CH CH CH H H 2,6 · Er Mo 3,3,3-hexafluoropropene _ 帑 帑 247 2,Φ dinonylphenyl CH CH CH CH HH 2,6»Dibromo bucket (1,1?2,3,33-hexafluoropropoxy)-butyl 248 2,6>dimethylphenyl CH CH CH H H 2,6»二漠4{1,1?2,3,3,3-hexafluoropropene 芊 sign) 249 2,3-difluorophenyl CH CH CH H H 2,6>二漠4"(1,1 ?2,3,3,3-hexafluoropropene|[Very narrow] 2-50 2, 'difluorophenyl CH CH CH CH HH 2,6 dibromo·Φ (1,1 and 333-hexafluoropropyl Fengji) Sheep base 2-51 2,5-difluorophenyl CH CH CH H H 2,6 »二漠4<1,1?2,3,3,3-hexafluoropropanthine) Ping-Ping 2-52 2 nd difluorophenyl CH CH CH CH HH 2, Fuyi > Smelly Winter (1, 152,3,3,3-hexafluoropropyl-yl) palm 2-53 3,Φ difluorophenyl CH CH CH CH HH 2,6-->Smelly 4-(1,152,3,3, 3-hexafluoropropyl group) stupid tomb 2-54 3> difluorophenyl CH CH CH H H 2 2, dibromo 4 (1,1 and 3,3,3-hexafluoropropanone climbing 荃2- 55 2,3-Dichlorophenyl CH CH CH CH HH 2,6--Moist 4-(1,1523,3,3-hexa-propanyl)-yl 2-56 2,4-dichlorophenyl CH CH CH CH HH 2,6»Dibromo"4<1,1 and 3,3,3-hexafluoropropane climbing) Benzene 2-57 2"Dichlorophenyl CH CH CH CH HH 2,6- —溪4-(1,152,3,3,3-six rat propoxyl ^^2- 2- 2 2, 孓dichlorophenyl CH CH CH :OH HH 2,6*二溪4<1,1 ?2,3,3,3-hexafluoropropene|1 sign) section sign 2-59 3,4«dichlorophenyl CH CH CH LCE [HH hexafluoride two-handed sign) 2-60 Schottky phenyl CH :CH CH [OH [HH --------- 2 Jieyi / stinky car (W again 3,3,3_hexafluoropropoxy)phenyl 96 200836629 Table 4) <匕For the numbering Qi a, 2 A53 A54 Ri r2 Q2 2-61 Schottyl phenyl CH CH CH<CH HH 2,6> Dibromo 4 (1,1?2,3,3,3 -hexafluoropropoxy)phenyl 2-62 2,6·dimethoxyphenyl CH CH CH丨CH HH 2,6«dibromo car (1,1 and 3,3,3-hexafluoropropoxy Phenyl 2-63 3>dimethoxyphenyl CH CH CH H H 2 ,6>dibromo 4-(1,123,33-hexafluoropropoxy)phenyl 2-64 3-methyl 4» Nitrophenyl CH CH CH H H 2 , Fu Er Mo 1 (1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-65 5-Amino-2-phenylphenyl CH CH CH CH HH 2,6·Dibromo 4(1,1^23,33-hexafluoropropoxy)phenyl 2-66 3-fluoro-2-indolylphenyl CH CH CH HH 2,6· Dibromo 1(1,1?2,3,3,3-hexafluoropropanyl-2-phenyl 2-fluoro-5-schhoffylphenyl CH CH CH HH 2,6«dibromo>4{1 ,1?2,3,3,3-hexafluoropropoxy)phenyl 2-68 4-Den-3-Shischyl Phenyl CH CH CH CH HH 2,6-Dibromo 4<1,1?2, 33,3-Hexafluoropropoxy)phenyl 2-69 5-Gas-2-Gentocylphenyl CH CH CH CH HH 2,6«Dibromo 4<1,1;2,3,3,3- Hexafluoropropoxy)phenyl 2-70 2-gas-6-mothyl CH CH CH CH HH 2,6·dibromo 4C1, U3,33-hexafluoropropoxy) phenyl 2-71 2- Fluoro-5-di-1-methylphenyl CH CH CH CH HH 2,6·dibromo 1(1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-72 2-chloro- 4·Shi Xiaoji CH CH CH CH HH 2 kg of dibromo 4<1,1 and 3,33-hexafluoropropoxy)phenyl 2-73 2-chloro·4~disorganophenyl GH CH CH HH 2,6-II Bromohexafluoropropoxy)phenyl 2-74 2-chloro-6·gasphenyl CH CH CH CH HH 2,6·dibromo 4<1,1 and 3,3,3-hexafluoropropoxy) Phenyl 2-75 3, chloro-4-like phenyl CH CH CH [OH HH 2,6> Dibromo bucket (1,1^2333-hexafluoropropoxy)phenyl 2-76 4-chloro-2 -1phenyl CH CH CH CH HH 2,6»二漠冬(1,1?2,3,33-hexafluoropropoxy)phenyl 2-77 4»Chloro-2-stone basementyl CH CH CE [CE IHH 2,6·dibromo 4<1,1?2,353,3-hexafluoropropoxy)phenyl 2-78 3-decyloxycar Shikiylphenyl:CH;CH [CE ICF. IHH 2, 6·Dibromo- winter (1,1?2,3,3,3-hexafluoropropoxyl)phenyl 2-79 2-methoxy 4 «renylbenzene, CH [CE [a ICF IHH 2, 6»二漠4(1,12333-hexafluoropropoxy)phenyl 2-80 2,3,4«trifluorophenyl CE [CH [a Id IHH 2,6·dibromo 4<1, U3, 3,3-hexafluoropropoxy)phenyl 97 200836629 Table 2 (5)
編號 Qi A?! a’2 A A、 Ri r2 Qi 2-81 2,4,6>三甲基苯基 CH CH CH( CH H H 2,6·二溴冬(1,U3,3,3-六氟丙氧基)苯基 2-82 2,3,6·三氟苯基 CH CH CH丨 CH H H 2,6·二溴l(l,l又3,3,3-六氟丙氧基)苯基 2-83 2,4,5-三甲氧基苯基 CH CH CH CH H H 2,6>二备车(1,192,3,3,3-六氟丙氧基)苯基 2-84 3,4,5-三甲氧基苯基 CH CH CH CH H H 2,6·二漠冬(1,1又3,3,3-六氟丙氧基)苯基 2-85 2,3,4,5,6«五氟苯基 CH CH CH CH H H 2,6·二溴1(1,1又3,3,3-六氟丙氧基)苯基 2-86 2-聯苯基 CH CH CH CH H H 2,6-二溴斗(1,1?2,3,3,3-六氟丙氧基)苯基 2-87 3-聯苯基 CH CH CH CH H H 2,6~二^臭4{1,1?2,3,3,3-六氟丙氧基)苯基 2-88 1-蔡基 CH CH CH CH H H 2,6·二溴l(l,U3,33-六氟丙氧基)苯基 2-89 2-萘基 CH CH CH CH H H 2,6»二溴4<1,1;2,3,3,3-六氟丙氧基)苯基 2-90 11比0定-2-基 CH CH CH CH H H 2,6·二漠4^1,1又333-六氟丙氧基)苯基 2-91 ^比口定-3-;^ CH CH CH CH H H 2,6-二溴4<1,1又3,3,3-六氟丙氧基)苯基 2-92 *定冬基 CH CH CH CH H H 2,6·二溴4»(1,U3,33-六氟丙氧基)苯基 2-93 2-甲基nfcb2定-5-基 CH CH CH CH H H 2,孚二漠4<1,152,3,3,3-六氟丙氧勤苯基 2-94 3-甲基口比口定-2-基 CH CH CH OH H H 2介二溴冬(1,1二3,3,3-六氟丙氧基)苯基 2-95 2·敗咖定-3-基 CH CH CH CH H H 2知二溴^K1,U3,3,3-六氟丙氧基)苯基 2-96 2-氣吼。定-3-基 CH CH Oi CE H H 2,6>二漠冬(1,1;2,3,3,3-六氟丙氧基)苯基 2-97 2-氯口比口定*4·基 CH CH CH CK H H 2,6>二溴1(1,1又3,33-六氟丙祕)苯基 2-98 2-氣口比口定-6·基 CH CH CH :CE I H H 2,6>二溴牟(1,1又3,3,3-六氟丙氧基)苯基 2-99 2,氯口比口定-5-基 CH CH :CH a I H H 2,6·二漠叫以幻%-六氟丙氧基)苯基 2400 5-義/比口定-2-基 OH CH [OH a I H H 2知二漠六氟丙氧基)苯基 98 200836629 表2⑹ 化糾勿 編號 Qi Α9! α’2 A’3 A,4: Ri r2 q2 2-101 4~二氣甲基0比0定-3-基 CH CH CH CH H H: 2,孚二漠4<1,1又3,3,3-六氟丙氧基)苯基 2-102 比°定-2-^^ CH CH CH CH H Π: 2,6·二漠#1,12333-六氟丙氧基)苯基 2403 2-苯氧基°比。定-3_基 CH CH CH CH H H: 2,孚二溴1(1,1?2,3,3,3-六氟丙氧基)苯基 2-104 2-曱基硫口比口定-3-基 CH CH CH CH H H 2,孚二漠斗^^力乂六氟丙氧勤苯基 2-105 2,6·二甲乳基口比口定-3-基 CH CH CH CH H H 2,6«二漠4<1,1又3,3,3-六氟丙氧基)苯基 2406 2,3-二氯咖定-5-基 CH CH CH CH H H 2,6-二ilHKU又3,3,3-六氟丙氧基)苯基 2407 2,5-二氯吼唆-3-基 CH CH CH CH H H 2,6·二漠4(1,1又333-六氟丙氧基)苯基 2-108 2,6-二氯口比。定-3-基 CH CH CH CH H H 2,6·二/臭'4-{1,1?2,3,3,3-六氟丙氧基)苯基 2-109 3,5-二氯*定冬基 CH CH CH CH H H 2,6~二漠4<1,192,3,3,3-六氟丙氧基)苯基 2-110 邱匕口定-N-氧4 b~2-基 CH CH CH CH H H 2,6-二^臭·车(1,1又3,3,3-六氟丙氧基)苯基 2411 N-甲基^比络*~2-基> CH CH CH CH H H 2知二漠4<1:,1?2,3,3,3-六氟丙氧基)苯基 2-112 口比啡_2基 CH CH CH CH H H 2,6·二溴,以义^土六氟丙氧勤苯基 2-113 2H比呼-5-基 CH CH CH CH H H 2,6·二溴车六氟丙氧基)苯基 2414 4*三氟甲基愈定-5-基 CH ce CH CH H H 2,孚二漠4{1,192,3,3,3-六氟丙氧基)苯基 2-115 σ夫口南-2-基 CH CH iCH CH H H 2,6»二漠4(1,U3,33-六氟丙氧基)苯基 2-116 咬喃-3-基 CH CH [|CH CH H H 2,孚二溴4(1/1233,3-六氟丙氧D苯基 2-117 2-四氫吱喃基 CH CH [CH CH :H H 2,6>二溴3-六氟丙氧苯基 2418 3-四氫吱喃基 CH CK [CH CH :H H 2,6»二漠六氟丙氧基)苯基 2-119 苯并吱喃·2-基 CH Or DCH :CH [H H 2,孓二漠1(1,12333-六氟丙氧基)苯基 2420 四氫口夫喃-2-基 CH Ct ICH :CH [H H 2斤二^々^“,,,七六氟丙觸苯基 99 200836629 表 2(7) 化剖勿 編號 Qi A?! a,2 A,3 A,4 Ri r2 Q2 2-121 2-甲基-5,6·二氫4H -口底喃-3-基 CH CH CH CH H H : 於二漠3-六氟丙氧基)苯基 2-122 嗟务2-基 CH CH CH CH H H : 2,6_二漠斗(1,1又3,3,3-六氟丙氧基)苯基 2-123 σ塞口+3-基 CH CH CH CH H H : 2,6·二漠3,3-六氟丙氧基)苯基 2424 3-甲基售吩·2-基 CH CH CH CH H H : 之斤二^臭^^以幻:^-六氟丙氧勒苯基 2-125 2-石肖基口塞吩·4~基 CH CH CH CH H H : 2,6«二漠~4<1,U33,3-六氟丙氧基)苯基 2-126 2-甲基嗟吩^基 CH CH CH CH H H : 2,6«二漠4-(1,1^233,3-六氟丙氧基)苯基 2-127 3姻夺2-基 CH CH CH CH H H 2冬二溴冬(1,1又3,3,3-六氟丙氧基)苯基 2-128 2-氯口塞口七5-基 CH CH CH CH H H 2,6»二溴4»(1,1二3,3,3-六氟丙氧基)苯基 2-129 3-溴嗟吩·2-基 CH CH CH CH H H 2,6·二溴冬(1,1又3,3,3-六氟丙氧基)苯基 2430 2->臭。塞口^-5-基 CH CH CH CH H H 2,6>二漠冬(1,1又3,33-六氟丙氧基)苯基 2-131 CH CH CH CH H H 2,6-二>臭冰(1,152,3,3,3-六鼠丙乳基)苯基 2432 3-苯基齡2-基 CH CH CH CH H H 2,6·二漠六氟丙祕)苯基 2433 2,4»二甲基1參分*5-基 CH CH CH CH H H 2斤二^臭4<1,1又3,3,3-六氟丙氧基)苯基 2434 苯弁口塞口^"2_基 CH CH CH CH H H 2,6·二溴斗(1,1?2,3,3,3-六氟丙氧基)苯基 2-135 丰硝基捕口比口私基 CH CH CH CH H H 2,孚二溴冬(1/1?2,3,3,3-六氟丙氧基)笨基 2-136 3-乙基-3H*坐4基 CH CH CH CH H H 2,6·二溴冬(以幻”-六氟丙氧勤苯基 2-137 1-甲基-3-硝基4H-吼 口坐冬基 CH CH CH CH H H 2,6-二>臭-4-(1,152,3,3,3-六氟丙氧基)苯基 2-138 3-氯4-甲基-IHwb坐 4基 CH CH CH :CH L Π H 2,6·二3-六氟丙氧基)苯基 2-139 3-漠4-甲基-1H-咐邊 碌 CH CH :OH [CE [H H 2,6*二溴4<1,U3,33-六氟丙氧基)苯基 2-140 1-甲基-3-三氟曱基 CE :CH :CE [CE [H H 2,6»3臭冬(以么^-六氟丙^^苯基 100 200836629 表 2(8) 化秘 編號 Qi A a’2 A93 A,4 Ri r2 Q2 2441 1-甲基>5-三氟甲基-1H- 口比口坐冬基 CH CH CH CH H H: 2知二溴·4<1,192,3,3,3-六氟丙氧勤苯基 2-142 異噚嗤-5-基 ‘ CH CH CH CH H H : 2,孓二漠斗^:^^土六氟丙氧勒苯基 2-143 4>三氟甲基嗟嗤-5-基 CH CH CH CH H H : 2,&二漠冬(1,1?2,33,3-六氟丙氧基)苯基 2-144 2,Φ二曱基嗟嗤-5-基 CH CH CH CH H H : 2,6>二漠车(1,1?2,33,3-六氟丙氧基)苯基 2-145 2-乙基本甲基。塞。坐-5-基 CH CH CH CH H H 2,6·二溴4(1,U333-六氟丙氧基)苯基 2-146 2-氯4·甲基嗟嗤-5-基 CH CH CH CH H H 2,6·二溴1(1,192,33,3-六氟丙氧基)苯基 2-147 3-甲基-異嗟嗤-5-基 CH CH CH CH H H 2,6·二溴專(1,1又3,3,3·六氟丙氧1)苯* 2-148 3,Φ二氯-異嗟嗤-5-基 CH CH CH CH H H 2,孚二漠4(1,1义3,3>六氟丙氧基)苯基 2-149 3-氯苯并·-2-基 CH CH CH CH H H 2,6«二溴4(1,1^23,33-六氟丙氧基)苯基 2-150 二氟-苯并[1.3]〕f唑 -5-基 CH CH CH CH H H 2,6·二溴4(1,1二3β,3-六氟丙觸苯基 2451 二氟-苯并[13]二令坐 基 CH CH CH CH H H 2,6·二溴4(1,1又3?3,3-六氟丙氧基)苯基 2-152 苯基 CH CH CH CH H H 2,6·二漠斗(1,1二3,3,3-六氟丙氧基)苯基 2-153 m苯基 CH CH CH CH H H 2,6>二漠车(1,123,3,3-六氟丙氧基)苯基 2-154 4·氟苯基 CH CH CH CH H H 2,6·二漠冬(1,1;2,353,3-六氟丙氧基)苯基 2455 4·鼠笨基 CE CH CH CH H H 2,6·二溴4^12333-六氟丙氧基)苯S 2-156 2-氯口比唆-3-基 OH CH CH CH H H 2,6·二溴冬^幻一夕六氟丙氧基体基 2-157 β肖基苯基 CK CH CH CH H H 2,孓二溴4(U;2353,3-六氟丙氧基)苯基 2-158 4»氰基苯基 OE CH :ce CH H H 2,6»二^臭4(1,U33,3-六氟丙氧基)苯基 2-159 苯基 CE CH :CH :CH :M( ^ H 2,6>二溴專(1,1?2,3,33-六氟丙氧基)苯基 2460 2-氟苯基 CF CH ;CH :CH :M( 2,6«二漠4(1,1?2,3,3,3-六氟丙氧基)苯基 101 200836629 表 2(9) 化射匆 編號 Qi A5! a’2 A’3 A’4 Ri r2 Q2 2461 4·氟苯基 CH CH CH CH Me H 2,6>二漠4<1,1又3,3,3-六氟丙_苯基 2-162 车氯苯基 CH CH CH CH Me H 2,6·二溴4(1,1?2,3,3,3-六氟丙氧基)苯基 2-163 2-氯口比口定-3-基 CH CH CH CH Me H 2介二溴-KU二3,3,3-六氟丙氧基)苯基 2-164 本硝基苯基 CH CH CH CH Me H 2,6«二溴4<1,1又3,3,3-六氟丙氧基)苯基 2-165 丰氰基苯基 CH CH CH CH Me H 2,6>二溴六氟丙氧基)苯基 2466 苯基 CH CH CH CH H Me 2,6>二漠4«(1,1又3,3,3-六氟丙氧基)苯基 2467 2-氟苯基 CH CH CH CH H Me 2,6~二^冬六氟丙氧基)苯基 2-168 4-就苯基 CH CH CH CH H Me 2,6«二溴六氟丙氧基)苯基 2469 4-氯苯基 CH CH CH CH H Me 2,6·二溴冬^:^力土六氟丙氧勤苯基 2470 2-氣呢口定-3-基 CH CH CH CH H Me 2,6>二溴4<1,1?2,3,3,3-六氟丙氧基)苯基 2-171 车硝基苯基 CH CH CH CH H Me 2,6·二溴4<1,1?2,3,33-六氟丙氧基)苯基 2-172 苯基 CH CH CH CH H Me 2,6·二溴4(1,1又3,3,3·六氟丙氧基)苯基 2-173 2-氯-3-石肖基苯基 CH CH CH CH H Me 2,6·二溴·Φ{1,1二33,3-六氟丙氧勤苯基 2-174 苯基 CH CH CH CH Me Me 2,6·二漠4(1,U3,33-六氟丙氧基)苯基 2475 2-氟苯基 CH CH CH CH Me Me 2知二^4<1,1?2,33,3-六氟丙氧基)苯基 2-176 4-氣苯基 Οι CH CH CH Me Me 2,6·二漠4(1,;1?2,3,3,3-六氟丙氧基)苯基 2-177 4·氣苯基 CH CH CH CH Me Me 2,6>二漠斗(1,1又3,3,3-六氟丙氧基)苯基 2-178 2-鼠吼口定-3-基 CH CH CH CH Me Me 〉2,6-二;臭六氟丙氧基)苯基 2-179 本硝基苯基 CH CH CH CH Me Me 〉2,孚二漠-4<1,1;2,3,33-六氟丙氧基)苯基 2-180 4»氰基苯基 CH CH CH CH Me Me :2,6·二溴又3,3,3-六氟丙細苯基 200836629 表 2(10) 編號 Qi a’2 a’3 A Ri r2 q2 2-181 2-氣吼ϋ井-3-基 CH CH CH CH Me Me 2,6·二溴4<1,192,3,33-六氟丙氧羞)苯基 2-182 口密口定-5-基 CH CH CH CH Me Me 2,6-二漠冬(1,1^2333-六氟丙氧基)苯基 2-183 苯基 CH CH CH CH H H 2-溴4<1,1?2,3,3,3-六氟丙氧基)^甲基苯基 2484 苯基 CH CH CH CH Me H 2-溴冬(U^W-六氟丙氧基>各三氟甲絲基 2-185 苯基 CH CH CH CH H H 2-溴斗(1,1又3,3,3-六氟丙氧羞>^三氟曱基苯基 2-186 2-氣-3-口比口^^^ CH CH CH CH H H 2-溴4<1,1;2,3,3,3-六氟丙氧基>6»三氟甲基苯基 2487 苯基 CH CH CH CH Me H 2-溴々^“。。。-六氟丙氧基:岭硝基苯基 2-188 2-氣·3-σ 比 CH CH CH CH Me H 2-溴4<1,192,3,3,3-六氟丙氧基^瑞基苯基 2-189 苯基 CH CH CH CH H H 2,6·二甲基」K1,U3,3,3-六氟丙氧基)苯基 2490 2-氣 CH CH CH CH Me H 2,6·二甲基4<1,U3,3,3-六氟丙氧基)苯基 2-191 2-氣 11比口定,3基 CH CH CH CH Me H 2,6»二曱基4<1,U33,3-六氟丙氧基)苯基 2492 苯基 CF CH CH CH H H 2,6·二甲基4<1,152,3,3,3-六氟丙氧基)苯基 2-193 2-氟綠 CF CH CH CB :H H 2介二甲基1(1,1二3,3,3-六氟丙氧基)苯基 2494 2-氯 CF CH CH CH [H H 2,6·二甲基车(1,1又3,3,3-六氟丙氧基)苯基 2495 苯基 CH CF OH [CH [H H 2,6»二甲基车(1,1又3,3,3-六氟丙氧基)苯基 103 200836629 表 2(11) 編號 Qi A?! a,2 A,3 A,4 Ri r2 q2 2-196 2-鼠-3-α 比 CH CF CH CH H H 2斤二甲基车(1,192,3,3,3-六氟丙祕)苯基 2-197 苯基 CH CH CH CH H H 6·溴六氟丙氧基嗟嚇基) 2-198 2-氣苯基 CH CH CH CH H H 6·溴-8<1,1?2,3,3,3-六氟丙氧基者淋-5-基) 2-199 2-氯-3看緣 CH CH CH CH H H 6·漠各仏以^土^-六氟丙氧基嗟嚇^-基) 2-200 苯基 CH CH CH CH Me H 6·溴各(1,U353,3-六氟丙氧基令淋-5-基) 2-201 苯基 CH CH CH CH H H 2,6>二溴四氟乙氧基)苯基 2-202 2-氟苯基 CH CH CH CH H H 2,6-二漠四氟乙氧基)苯基 2-203 2-氯各口比口^^ CH CH CH CH H H 2,6~二>臭-4-(1,1?292-四氣1乙氧基)苯基 2-204 苯基 CH CH CH CH H H 2_溴雙(1,12333-六氟丙氧基)苯基 2-205 2·氟苯基 CH CH CH CH H H 2-漠46·雙(^^。,孓六氟丙氧勘苯基 2-206 2·氣-3-口比口 CH CH CH CH H H 2-溴4,6·雙(1,152,3,3,3-六氟丙氧基)苯基 2-207 苯基 CH CH CH CH H H 2,4,6«三(1,1又3,33·六氟丙氧基)苯基 2-208 2·襄苯基 CH CH CH CH H H 2,4,6>三(1,1?2,3,3,3-六氟丙氧基)苯基 2-209 2-氯-3,口比口 .CH CH CH CH H H 2,4,6-三(1,1又3,3,3-六氟丙氧基)苯基 2-210 苯基 CH CH CH CH H H 2,6«二溴^。^,”-六氟丙硫勤苯基 104 200836629 表 2(12) 化祝勿 編號 Qi A?! a’2 A’3 A,4 Ri r2 Q2 2-211 苯基 CH CH CH CH H H 2,6·二漠4{1,1又3,3,3-六氟丙硫基)苯基 2-212 2-氯各口比唆基 CH CH CH CH H H 2,6·二^臭4{1,1?2,3,3,3-六氟丙硫基)苯基 2-213 苯基 CH CH CH CH H H 2-溴各氯4^1,1^2,3,3,3-六氟丙硫基)苯基 2-214 2-氟苯基 CH CH CH CH H H 2-溴各氯4^123,33-六氟丙疏基)苯基 2-215 2-氣-3-口比 CH CH CH CH H H 2-溴各氯4<1,1?23,3,3-六氟丙硫基)苯基 2-216 苯基 CH CH CH CH Me H 2-溴-6>氯4<1,1又3,3,3-六氟丙硫基)苯基 2-217 2-說苯基 CH CH CH CH Me H 2-溴各氯4(1,U3,3,3-六氟丙硫基)苯基 2-218 2-鼠 CH CH CH CH Me H 2-溴各氯冬(1,1又3,3,3-六氟丙硫基)苯基 2-219 2-鼠-3-口比口^^· CH CH CH CH Me H 2,6·二甲基1,1>三氟r2-三氟甲氧基乙_ 苯基 2-220 2-氣-3·° 比 CH CH CH CH H H 2,6-二曱基·4-( 1,152,3,33-六氣丙氧基)苯基No. Qi A?! a'2 AA, Ri r2 Qi 2-81 2,4,6> Trimethylphenyl CH CH CH(CH HH 2,6·Dibromo-冬(1,U3,3,3-Six Fluoropropoxy)phenyl 2-82 2,3,6·trifluorophenyl CH CH CH丨CH HH 2,6·dibromo l (l,l and 3,3,3-hexafluoropropoxy) Phenyl 2-83 2,4,5-trimethoxyphenyl CH CH CH H H 2,6>Two preparation vehicles (1,192,3,3,3-hexafluoropropoxy)phenyl 2-84 3,4,5-trimethoxyphenyl CH CH CH H H 2 2,6·二漠冬(1,1,3,3,3-hexafluoropropoxy)phenyl 2-85 2,3,4 ,5,6«pentafluorophenyl CH CH CH CH HH 2,6·dibromo 1 (1,1 and 3,3,3-hexafluoropropoxy)phenyl 2-86 2-biphenyl CH CH CH CH HH 2,6-dibromo bucket (1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-87 3-biphenyl CH CH CH CH HH 2,6~2^ Stinky 4{1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-88 1-Cai CH CH CH CH HH 2,6·dibromo l (l, U3, 33-six Fluoropropoxy)phenyl 2-89 2-naphthyl CH CH CH CH HH 2,6»dibromo 4<1,1; 2,3,3,3-hexafluoropropoxy)phenyl 2-90 11 to 0-but-2-yl CH CH CH CH HH 2,6·二漠4^1,1 and 333-hexafluoropropoxy)phenyl 2-91 ^ 比口定-3-;^ CH CH CH CH HH 2,6-dibromo 4<1 1 again 3,3,3-hexafluoropropoxy)phenyl 2-92 *Dedyl CH CH CH CH HH 2,6·dibromo 4»(1,U3,33-hexafluoropropoxy)benzene 2-93 2-methyl nfcb2 determinate-5-yl CH CH CH CH HH 2, Fu Er Mo 4 <1,152,3,3,3-hexafluoropropoxyphene 2-94 3-methyl Oral ratio of 2-yl CH CH CH OH HH 2 dibromo-methanol (1,1 2,3,3,3-hexafluoropropoxy)phenyl 2-95 2· defeated -3-yl CH CH CH CH HH 2 knows dibromo^K1, U3,3,3-hexafluoropropoxy)phenyl 2-96 2-gas. Ding-3-yl CH CH Oi CE HH 2,6> Er Modong (1,1;2,3,3,3-hexafluoropropoxy)phenyl 2-97 2-chloro port ratio *4 ·Base CH CH CH CK HH 2,6>Dibromo 1 (1,1 and 3,33-hexafluoropropyl)phenyl 2-98 2-port ratio -6-based CH CH CH :CE IHH 2 ,6>Dibromoindole (1,1,3,3,3-hexafluoropropoxy)phenyl 2-99 2, chlorophenanthylamine-5-yl CH CH :CH a IHH 2,6·2 Indifference to pheno%-hexafluoropropoxy)phenyl 2400 5-yi/Butyl-2-yl OH CH [OH a IHH 2 知二漠 hexafluoropropoxy)phenyl 98 200836629 Table 2 (6) Do not number Qi Α9! α'2 A'3 A,4: Ri r2 q2 2-101 4~ Dimethylmethyl 0 to 0 -3--3-CH CH CH CH HH: 2, Fu Er Mo 4<1, 1 and 3,3,3-hexafluoropropoxy)phenyl 2-102 ratio °-2-^^ CH CH CH CH H Π: 2,6·二漠#1,12333-hexafluoropropoxy Phenyl 2403 2-phenoxy ° ratio.定-3_基CH CH CH CH HH: 2, Fulbazo 1 (1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-104 2-mercaptosulfate ratio -3-yl CH CH CH CH HH 2, Fu Er Modou ^^力乂 hexafluoropropoxybenzene phenyl 2-105 2,6·dimethyl emulsion base ratio -3-yl CH CH CH CH HH 2,6 «二漠4<1,1 and 3,3,3-hexafluoropropoxy)phenyl 2406 2,3-dichlorocadine-5-yl CH CH CH CH HH 2,6-di ilHKU Further 3,3,3-hexafluoropropoxy)phenyl 2407 2,5-dichloroindol-3-yl CH CH CH CH HH 2,6·2 desert 4 (1,1 and 333-hexafluoropropyl Oxy)phenyl 2-108 2,6-dichloroport ratio. Ding-3-yl CH CH CH CH HH 2,6·di/odor '4-{1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-109 3,5-dichloro *定冬基 CH CH CH CH HH 2,6~二漠4<1,192,3,3,3-hexafluoropropoxy)phenyl 2-110 Qiu Yukou Ding-N-Oxygen 4 b~2 -Base CH CH CH CH HH 2,6-二^臭·车(1,1,3,3,3-hexafluoropropoxy)phenyl 2411 N-methyl^pyro-*~2-based> CH CH CH CH HH 2 Zhi Er Mo 4<1:,1?2,3,3,3-hexafluoropropoxy)phenyl 2-112-portage- -2-yl CH CH CH CH HH 2,6· Dibromo, hexafluoropropoxybenzene phenyl 2-113 2H than hept-5-yl CH CH CH CH H 2 2,6 · dibromo car hexafluoropropoxy) phenyl 2414 4 * trifluoromethyl Kefuding-5-yl CH ce CH CH HH 2, Fu Er Mo 4{1,192,3,3,3-hexafluoropropoxy)phenyl 2-115 σ Fukou Nan-2-yl CH CH iCH CH HH 2,6»二漠4(1,U3,33-hexafluoropropoxy)phenyl 2-116 benzo-3-yl CH CH [|CH CH HH 2, bis 2 bromo 4 (1/ 1233,3-hexafluoropropoxyl D-phenyl 2-117 2-tetrahydrofurfuryl CH CH [CH CH :HH 2,6>dibromo 3-hexafluoropropoxyphenyl 2418 3-tetrahydrofuranyl CH CK [CH CH :HH 2,6»II hexafluoropropoxy)phenyl 2-119 benzopyran-2-yl CH Or DCH :CH [HH 2, 孓二漠1(1,12333-hexafluoropropoxy)phenyl 2420 tetrahydrofuran-2-yl CH Ct ICH :CH [HH 2 kg 2 ^々^", ,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, 4H - Oral-3-yl CH CH CH CH HH : Yu Erqian 3-hexafluoropropoxy)phenyl 2-122 2- 2- 2-yl CH CH CH CH HH : 2,6_二漠斗( 1,1,3,3,3-hexafluoropropoxy)phenyl 2-123 σ-port +3-based CH CH CH CH HH : 2,6· 二漠 3,3-hexafluoropropoxy) Phenyl 2424 3-methyl phenanthrene-2-yl CH CH CH CH HH : jin 2 odor ^^ with illusion: ^-hexafluoropropoxyl phenyl 2-225 2-shi Xiaojikou phenanthene 4~ CH CH CH CH HH : 2,6 «二漠~4<1,U33,3-hexafluoropropoxy)phenyl 2-126 2-methyl fluorene-based CH CH CH CH HH : 2,6 «二漠4-(1,1^233,3-hexafluoropropoxy)phenyl 2-127 3 marriage 2-based CH CH CH CH HH 2 winter dibromo winter (1,1 and 3,3, 3-hexafluoropropoxy)phenyl 2-128 2-Chloro-port 7-based CH CH CH CH HH 2,6»Dibromo 4»(1,1 2,3,3,3-hexafluoropropane Oxy)phenyl 2-129 3-bromophene·2- CH CH CH CH H H 2,6 · Winter dibromo (1,1 and 3,3,3-hexafluoro-propoxy) phenyl 2430 2- > smell. Plug mouth ^-5-based CH CH CH CH HH 2,6> Er Modong (1,1 and 3,33-hexafluoropropoxy)phenyl 2-131 CH CH CH CH HH 2,6-two> ; stinky ice (1,152,3,3,3-hexa-propyl propyl) phenyl 2432 3-phenyl-in 2-based CH CH CH CH HH 2,6·two hexafluoropropyl phenyl) phenyl 2433 2,4»dimethyl 1 parameter *5-based CH CH CH CH HH 2 kg 2 odor 4 < 1,1 and 3,3,3-hexafluoropropoxy)phenyl 2434 benzoquinone port ^"2_基CH CH CH CH HH 2,6·Dibromo bucket (1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-135 CH CH CH CH HH 2, dibromobutan (1/1?2,3,3,3-hexafluoropropoxy) phenyl 2-136 3-ethyl-3H* sitting 4 based CH CH CH CH HH 2,6·dibromo- winter (Imaginary)-hexafluoropropoxyphene 2-137 1-methyl-3-nitro 4H-吼口坐冬基 CH CH CH CH HH 2,6-二> Odor 4-(1,152,3,3,3-hexafluoropropoxy)phenyl 2-138 3-chloro-4-methyl-IHwb sitting on 4 base CH CH CH :CH L Π H 2,6 · bis 3-hexafluoropropoxy)phenyl 2-139 3-wet 4-methyl-1H-indole CH CH : OH [CE [HH 2,6* dibromo 4 < 1, U3, 33- Hexafluoropropoxy)phenyl 2-140 1-methyl-3-trifluorodecyl CE :CH :CE [CE [HH 2,6»3 stinky Winter (以^^-hexafluoropropene^^phenyl 100 200836629 Table 2 (8) Framing number Qi A a'2 A93 A,4 Ri r2 Q2 2441 1-methyl>5-trifluoromethyl-1H - mouth mouth is sitting on the winter base CH CH CH CH HH: 2 knows dibromo- 4<1,192,3,3,3-hexafluoropropoxyphenophenyl 2-142 isoindole-5-yl' CH CH CH CH HH : 2, 孓二漠斗^:^^土 hexafluoropropoxyl phenyl 2-143 4> trifluoromethyl fluoren-5-yl CH CH CH CH HH : 2, & (1,1?2,33,3-hexafluoropropoxy)phenyl 2-144 2,Φ diindolyl-5-yl CH CH CH CH HH : 2,6>Two desert vehicles (1, 1? 2,33,3-hexafluoropropoxy)phenyl 2-145 2-ethyl-p-methyl. Plug. -5-based CH CH CH CH HH 2,6·dibromo 4(1,U333-hexafluoropropoxy)phenyl 2-146 2-chloro-4-methylguanidin-5-yl CH CH CH CH HH 2,6·dibromo 1(1,192,33,3-hexafluoropropoxy)phenyl 2-147 3-methyl-isoindole-5-yl CH CH CH CH HH 2,6·2 Bromine (1,1,3,3,3·hexafluoropropoxy 1)benzene* 2-148 3,Φ dichloro-isoindole-5-yl CH CH CH CH HH 2, Fu Er Mo 4 (1 ,1 meaning 3,3>hexafluoropropoxy)phenyl 2-149 3-chlorobenzo--2-yl CH CH CH CH HH 2,6«dibromo 4 (1,1^23,33-six Fluoropropoxy)phenyl 2-150 difluoro-benzo[1.3]]fazole-5-yl CH CH CH CH HH 2,6·dibromo 4 (1,1 2 3β,3-hexafluoropropene Phenyl 2451 difluoro-benzo[13]dienyl CH CH CH CH HH 2,6·dibromo 4 (1,1 and 3?3,3-hexafluoropropoxy)phenyl 2-152 benzene CH CH CH CH H H 2,6·Second (1,1 2,3,3,3-hexafluoropropoxy)phenyl 2-153 m phenyl CH CH CH H H 2,6> (1,123,3,3-hexafluoropropoxy)phenyl 2-154 4·fluorophenyl CH CH CH CH HH 2,6·二漠冬(1,1;2,353,3-hexafluoropropoxy) Phenyl 2455 4 · 鼠基基CE CH CH CH HH 2,6·dibromo 4^12333-hexafluoropropoxy)benzene S 2-156 2-Chloro-port 唆-3-yl OH CH CH CH HH 2,6·Dibromo- winter phantom hexafluoropropoxy group 2-157 β-Schiffkiphenyl CK CH CH CH HH 2, bismuth dibromide 4(U; 2353,3-hexafluoropropoxy)phenyl 2-158 4»cyanophenyl OE CH :ce CH HH 2,6»二^臭4(1,U33,3-hexafluoropropoxylate Phenyl 2- phenyl phenyl CE CH : CH : CH : M ( ^ H 2, 6 > dibromo (1,1?2,3,33-hexafluoropropoxy)phenyl 2460 2-fluoro Phenyl CF CH ; CH : CH : M ( 2,6 « 二漠 4(1,1?2,3,3,3-hexafluoropropoxy)phenyl 101 200836629 Table 2 (9) Qi A5! a'2 A'3 A'4 Ri r2 Q2 2461 4·fluorophenyl CH CH CH CH Me H 2,6> Er Mo 4<1,1 and 3,3,3-hexafluoropropene-benzene 2-162 chlorophenyl CH CH CH CH Me H 2,6·dibromo 4 (1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-163 2-chloro port ratio Ordin-3-yl CH CH CH CH Me H 2 Dibromo-KU 2,3,3-hexafluoropropoxy)phenyl 2-164 nitrophenyl CH CH CH CH H 2,6 «Dibromo 4<1,1 and 3,3,3-hexafluoropropoxy)phenyl 2-165 cyanophenyl CH CH CH CH H H,6>dibromohexafluoropropoxy)benzene Base 2466 phenyl CH CH CH CH H Me 2,6> Er Mo 4«(1,1 Further 3,3,3-hexafluoropropoxy)phenyl 2467 2-fluorophenyl CH CH CH H Me 2,6~2^Winter hexafluoropropoxy)phenyl 2-168 4-phenyl CH CH CH CH H Me 2,6 «dibromohexafluoropropoxy)phenyl 2469 4-chlorophenyl CH CH CH CH H Me 2,6·dibromo-tung Base 2470 2-gas-n-but-3-yl CH CH CH CH H Me 2,6>dibromo 4<1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-171 Nitrophenyl CH CH CH CH H 2 2,6·dibromo 4<1,1?2,3,33-hexafluoropropoxy)phenyl 2-172 phenyl CH CH CH H Me 2,6 ·Dibromo 4(1,1,3,3,3·hexafluoropropoxy)phenyl 2-173 2-chloro-3-stone schylyl CH CH CH CH H Me 2,6·dibromo·Φ{ 1,1,2,33,3-hexafluoropropoxyphenephenyl 2-174 phenyl CH CH CH Me Me 2,6·二漠4(1,U3,33-hexafluoropropoxy)phenyl 2475 2 -fluorophenyl CH CH CH Me Me 2 knows 2^1<1,1?2,33,3-hexafluoropropoxy)phenyl 2-176 4-phenylphenyl oxime CH CH CH Me Me 2, 6·二漠4(1,;1?2,3,3,3-hexafluoropropoxy)phenyl 2-177 4·gas phenyl CH CH CH CH Me Me 2,6> ,1,3,3,3-hexafluoropropoxy)phenyl 2-178 2-purine oxime-3-yl CH CH CH CH Me Me 〉2,6-di; odorous hexafluoropropoxy)phenyl 2-179 nitrophenyl CH CH CH Me Me 〉2, Fu Erqian-4<1,1;2, 3,33-hexafluoropropoxy)phenyl 2-180 4»cyanophenyl CH CH CH Me Me : 2,6·dibromo and 3,3,3-hexafluoropropylphenyl 200836629 (10) No. Qi a'2 a'3 A Ri r2 q2 2-181 2-gas well -3-based CH CH CH CH Me Me 2,6·dibromo 4<1,192,3,33- Hexafluoropropoxy succinyl) phenyl 2-182 cryptophene-5-yl CH CH CH CH Me Me 2,6-two deserts (1,1^2333-hexafluoropropoxy)phenyl 2-183 Phenyl CH CH CH CH HH 2-bromo 4<1,1?2,3,3,3-hexafluoropropoxy)^methylphenyl 2484 Phenyl CH CH CH CH Me H 2-Bromodong (U ^W-hexafluoropropoxy group> each trifluoromethyl group 2-185 phenyl CH CH CH HH 2-bromo bucket (1,1 and 3,3,3-hexafluoropropoxyspirate>^3 Fluorodecylphenyl 2-186 2-gas-3-port ratio ^^^ CH CH CH CH HH 2-bromo 4<1,1;2,3,3,3-hexafluoropropoxy>6 »Trifluoromethylphenyl 2487 phenyl CH CH CH CH Me H 2-bromo 々^". . . -hexafluoropropoxy group: ridge nitrophenyl 2-188 2-gas·3-σ ratio CH CH CH CH Me H 2-bromo 4<1,192,3,3,3-hexafluoropropoxy^ Retyl phenyl 2-189 phenyl CH CH CH CH HH 2,6·dimethyl"K1,U3,3,3-hexafluoropropoxy)phenyl 2490 2-gas CH CH CH CH Me H 2, 6·Dimethyl 4<1,U3,3,3-hexafluoropropoxy)phenyl 2-191 2-gas 11 specific, 3 based CH CH CH CH Me H 2,6»dimercapto 4< ; 1, U33,3-hexafluoropropoxy)phenyl 2492 Phenyl CF CH CH CH HH 2,6·Dimethyl 4<1,152,3,3,3-hexafluoropropoxy)phenyl 2-193 2-fluorogreen CF CH CH CB :HH 2 Dimethyl 1 (1,1 2,3,3-hexafluoropropoxy)phenyl 2494 2-chloro CF CH CH CH [HH 2, 6· dimethyl car (1,1 and 3,3,3-hexafluoropropoxy)phenyl 2495 phenyl CH CF OH [CH [HH 2,6» dimethyl car (1,1 and 3, 3,3-Hexafluoropropoxy)phenyl 103 200836629 Table 2(11) No. Qi A?! a,2 A,3 A,4 Ri r2 q2 2-196 2-Mouse-3-α Than CH CF CH CH HH 2 kg dimethyl car (1,192,3,3,3-hexafluoropropyl) phenyl 2-197 phenyl CH CH CH H H 6 · bromohexafluoropropoxy fluorene) 2- 198 2-Phenylphenyl CH CH CH CH HH 6·Bromo-8<1 1?2,3,3,3-hexafluoropropoxyl lysyl-5-yl) 2-199 2-Chloro-3 look at CH CH CH CH HH 6 · 漠 仏 ^ ^ ^ ^ hexafluoropropyl嗟 嗟 ^ - 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- CH HH 2,6>dibromotetrafluoroethoxy)phenyl 2-202 2-fluorophenyl CH CH CH HH 2,6-di-difluoroethoxy)phenyl 2-203 2-chloro each Mouth ratio ^^ CH CH CH CH HH 2,6~2>Smelly-4-(1,1?292-tetrakis-1ethoxy)phenyl 2-204 Phenyl CH CH CH H H 2 2 Bromine Bis(1,12333-hexafluoropropoxy)phenyl 2-205 2·fluorophenyl CH CH CH CH HH 2- desert 46·double (^^. , hexafluoropropoxy phenyl 2-206 2 · gas -3- mouth ratio CH CH CH CH HH 2- bromo 4,6 · bis (1,152,3,3,3-hexafluoropropoxy Phenyl 2-207 Phenyl CH CH CH CH HH 2,4,6«Tris(1,1 and 3,33·hexafluoropropoxy)phenyl 2-208 2·襄phenyl CH CH CH CH HH 2,4,6>Tris(1,1?2,3,3,3-hexafluoropropoxy)phenyl 2-209 2-chloro-3, mouth ratio. CH CH CH CH HH 2,4, 6-Tris(1,1 and 3,3,3-hexafluoropropoxy)phenyl 2-210 phenyl CH CH CH H H 2 2,6 «dibromo^. ^,"-Hexafluoropropylthiophenyl 104 200836629 Table 2 (12) Hua Zhu Do not number Qi A?! a'2 A'3 A,4 Ri r2 Q2 2-211 Phenyl CH CH CH CH HH 2, 6·二漠4{1,1 and 3,3,3-hexafluoropropylthio)phenyl 2-212 2-chloro each than thiol CH CH CH CH HH 2,6·2^ odor 4{1 ,1?2,3,3,3-hexafluoropropylthio)phenyl 2-213 phenyl CH CH CH HH 2-bromochloro 4^1,1^2,3,3,3-hexafluoro Propylthio)phenyl 2-214 2-fluorophenyl CH CH CH CH HH 2-bromo-chloro 4^123,33-hexafluoropropanyl)phenyl 2-215 2-gas-3-port ratio CH CH CH CH HH 2-bromo-chloro 4<1,1?23,3,3-hexafluoropropylthio)phenyl 2-216 phenyl CH CH CH CH Me H 2-bromo-6>Chlorine 4<1 ,1,3,3,3-hexafluoropropylthio)phenyl 2-217 2-Phenyl CH CH CH CH Me H 2-bromo-chloro 4 (1,U3,3,3-hexafluoropropane sulphur Phenyl 2-218 2-rat CH CH CH CH Me H 2-bromo-chlorobutyric (1,1,3,3,3-hexafluoropropylthio)phenyl 2-219 2-rat-3- Mouth ratio ^^· CH CH CH CH Me H 2,6·dimethyl 1,1>trifluoro-r2-trifluoromethoxy-phenyl- 2-phenyl 2-gas-3·° ratio CH CH CH CH HH 2,6-dimercapto 4-( 1,152,3,33-hexapropoxy)phenyl
105 200836629105 200836629
表 2(13) 化糾勿 編號 Qi A9! a’2 a,3 A、 Ri Ri Q2 6-1 苯基 CH CH CH CH H H 2,6-二甲基本(2_溴氟乙基)苯基 6-2 2-氯*定-3_基 CH CH CH CH H H 2,6~二甲基溴四氟乙基)苯基 6-3 苯基 CH CH CH CH Me H 2,6»二甲基车(2-溴-1,1又2,氟乙基)苯基 64 2-氯口比口定-3-基 CH CH CH CH Me H 2,6-二甲基·4<2-溴4,1又2-四氟乙勤苯基 &5 苯基 CH CH CH CH Me H 2-漠*4<2-溴-1,0四氟乙基甲基苯基 &6 2-氣°比°定各基 CH CH CH CH Me H 2-溴冬(2-溴-U二2-四氟乙基>6«甲基苯基 6-7 苯基 CH CH CH CH H H 2-溴各(2-溴4,1又2-四氟乙基w甲基苯基 6-8 2-氯口比口定各基 CH CH CH CH H H 2-溴溴-Ι,ΙΘ-四氟乙基甲基苯基 6-9 苯基 CH CH CH CH H H 2-溴-4<2-溴-1,1又2-四氟乙基> 三氟甲基亞磺醯基笨基 6-10 2魯比口定各基 CH CH CH CH H H 2-溴各(2-溴"UM-四氟乙基外 三氟甲基亞磺酿基笨基 H1 苯基 CH CH CH CH Me H 2-溴溴4,〇四氟乙基$ 三氟甲基亞續醯基笨基 642 2-氯口比口定-3,基 CH in CH CH :Me :H 2-溴斗(2-溴4,1么2-四氟乙基$ 三氟甲基亞磺醯基笨農 j-----—-- 通式(B)Table 2 (13) Correction No. Qi A9! a'2 a, 3 A, Ri Ri Q2 6-1 Phenyl CH CH CH CH HH 2,6-Dimethyl Basic (2_Bromofluoroethyl)phenyl 6-2 2-Chloro*3 -yl CH CH CH CH HH 2,6-Dimethylbromotetrafluoroethyl)phenyl 6-3 Phenyl CH CH CH CH H H 2,6»dimethyl Car (2-bromo-1,1 and 2,fluoroethyl)phenyl 64 2-chloro-port -3-yl CH CH CH CH Me H 2,6-dimethyl·4<2-bromo 4 ,1,2-tetrafluoroethendylphenyl &5 phenyl CH CH CH CH Me H 2-moistry*4<2-bromo-1,0tetrafluoroethylmethylphenyl & 6 2-gas The ratio of CH CH CH CH Me H 2-bromodong (2-bromo-U di-tetrafluoroethyl) 6 «methylphenyl 6-7 phenyl CH CH CH H H 2-bromo (2-Bromo-4,1-2-tetrafluoroethyl-w-methylphenyl 6-8 2-Chloroyl group, CH CH CH CH HH 2-bromo bromide-oxime, ΙΘ-tetrafluoroethyl A Phenyl 6-9 phenyl CH CH CH CH HH 2-bromo-4<2-bromo-1,1 2-tetrafluoroethyl> Trifluoromethylsulfinyl stupid base 6-10 2 Lu Specific conditions CH CH CH CH HH 2-bromo each (2-bromine " UM-tetrafluoroethyl external trifluoromethyl sulfinyl aryl stylyl H1 phenyl CH CH CH CH H H bromo bromide 4, 〇tetrafluoroethyl $ three Methyl hydrazine 笨 笨 642 642 2-Chloro port specific mouth -3, based CH in CH CH : Me : H 2- bromine bucket (2-bromo 4,1 2-fluoroethyl ethyl trifluoromethyl Kea sulfonyl stupid j-------- general formula (B)
(B) N 106 200836629 表3⑴ 化糾勿 編號 Qi a,2 a,3 A,4 Ri r2 q2 4-1 苯基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 4-2 2-曱基苯基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 4-3 2-1苯基 CH CH CH CH H H 2,6·二甲基-4-七氟異丙基苯基 4-4 3-氟苯基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 4-5 4-氟苯基 CH CH CH CH H H 2,6-二甲基-4-七氣異丙基苯基 4-6 4-氯苯基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 4-7 2-溴苯基 CH CH CH CH H H 2,6-二甲基斗七氟異丙基苯基 4-8 2_碳苯基 CH CH CH CH H H 2,6·二甲基-4·七氣異丙基苯基 4-9 4-氰基苯基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 4-10 2-硝基苯基 CH CH CH CH H H 2,6-二甲基-4-七氣異丙基苯基 4-11 4-硝基苯基 CH CH CH CH H H 2,6·二甲基斗七氟異丙基苯基 4-12 2-三氟甲基苯基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 4-13 4-曱氧基苯基 CH CH CH CH H H 2,6-二甲基-4-七氟i異丙基苯基 4-14 2-(乙醯基胺基)苯基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 4-15 2,4-二氟苯基 CH CH CH CH H H 2,6-二甲基-4-七氣異丙基苯基 4-16 2,3,4,5,6-五氟苯基 CH CH CH CH H H 2,6-二甲基-4-七氟^異丙基苯基 4-17 °比。定-2-基 CH CH CH CH H H 2,6-二甲基-4-七亂異丙基苯基 4-18 σ比定-3·基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 4-19 吨咬-4-基 CH CH CH CH H H 2,6-二甲基-4-七氟^異丙基苯基 4-20 2-亂°比咬-3-基 CH CH CH CH [H H 2,6-二甲基-4-七氣異丙基苯基 107 200836629 表 3(2) 化料勿 編號 Qi A9! a,2 A,3 A’4 Ri r2 〇2 4-21 2-氣ϋ比口定-3-基 CH CH CH CH H H 2,孚二甲基斗七氟異丙基苯基 4-22 Ν,氧4 hr0tb口定-2-基 CH CH CH CH H H -2,6~二甲基本七氟i異丙基苯基 4-23 甲基 CH CH CH CH H H 2,6·二曱基4»七氟異丙基苯基 4-24 甲基 CH CH CH CH Me H 2,6-二甲基·4»七氟異丙基苯基 4-25 乙基 CH CH CH CH H H 2,6·二甲基车七氟異丙基苯基 4-26 乙基 CH CH CH CH Me H 2,6·二甲基冰七氟異丙基苯基 4-27 2么2-三氟乙基 CH CH CH CH H H 2,6>二甲基冬七象異丙基苯基 4-28 2^-三氟乙基 CH CH CH CH Me H 2,6>二甲基车七氟異丙基苯基 4-29 乙烯基 CH CH CH CH H H 2知二甲基冰七氟異丙基苯基 4-30 乙烯基 CH CH CH CH Me H 2,6~二甲基 1七氟異丙基苯基 4-31 丙基 CH CH CH CH H H 2,6·二甲基4»七氟異丙基苯基 4-32 丙基 CH CH CH CH Me H 2,6·二甲基斗七氟異丙基苯基 4-33 異丙基 CH CH CH CH H H 2,6~二甲基4»七亂異丙基苯基 4-34 苄基 CH CH CH CH H H 2,6·二甲基冬七氣異丙基苯基 4-37 苯基 CH CH CH CH H H 2·溴Λ6·雙(三氟甲基)苯基 4-38 苯基 CH CH CH CH H H 2,4·雙(三氟甲基)苯基 4-39 苯基 CH CH CH CH H H 2-溴(七氟異丙基>6«(曱基磺_苯基 440 苯基 CH CH CH CH H H 2,6-二溴七氣正丙基硫)苯基 441 苯基 CH CH CH CH H H 2,孚二^4«(七氟正丙基亞續_苯基 442 苯基 CH CH CH CH H H 2,6·二甲基车(九氟τ2-丁基)苯基 108 200836629 表 3(3) 化糾勿 編號 Qi A5! a,2 A、 A54 Ri Ri Qi 443 苯基 CH CH CH CH H H 2,6>二溴^(以幻”-六氟丙氧基体基 444 苯基 CH CH CH CH H H 2-溴冬(1,1又3,3,3-六氟丙氧基>·6·曱基苯基 445 苯基 CH CH CH CH H H 6->臭-8-七氣異丙基嗟1淋-5-基 446 苯基 CH CH CH CH H H 2,孚二甲基4<2·溴三氟-1-三氟甲基乙基)·苯基 447 苯基 CH CH CH CH H H 2,6·二氯三氟小三氟曱基乙_苯基 448 苯基 CH CH CE CH H H 2,6·二氯4三氟曱基苯基 449 苯基 CH CH CH CH H H 2,Φ二溴各三氟甲基苯基 丰50 苯基 CH CH CH CH H H 2_溴4,6>雙(三氟甲基)苯基 丰51 苯基 CH CH CH CH H H 2,Φ雙(三氟甲基)苯基 4-52 苯基 CH CH CH CH H H 2->臭~6-(2又2-二氣-1-二氟^甲基乙氧基户比唆各基 通式(C)(B) N 106 200836629 Table 3 (1) Correction number Qi a, 2 a, 3 A, 4 Ri r2 q2 4-1 Phenyl CH CH CH CH HH 2,6-Dimethyl-4-heptafluoroisopropyl Phenyl 4-2 2-mercaptophenyl CH CH CH HH 2,6-dimethyl-4-heptafluoroisopropylphenyl 4-3 2-1 phenyl CH CH CH HH 2,6· Dimethyl-4-heptafluoroisopropylphenyl 4-4 3-fluorophenyl CH CH CH HH 2,6-dimethyl-4-heptafluoroisopropylphenyl 4-5 4-fluorobenzene CH CH CH CH HH 2,6-Dimethyl-4-heptafluorophenyl 4-6 4-chlorophenyl CH CH CH H H 2 2,6-dimethyl-4-heptafluoroisopropyl Phenyl 4-7 2-bromophenyl CH CH CH H H 2,6-dimethylidene heptafluoroisopropylphenyl 4-8 2_carbophenyl CH CH CH CH HH 2,6·dimethyl Base-4·seven-p-isopropylphenyl 4-9 4-cyanophenyl CH CH CH HH 2,6-dimethyl-4-heptafluoroisopropylphenyl 4-10 2-nitrobenzene CH CH CH CH HH 2,6-Dimethyl-4-heptylisopropylphenyl 4-11 4-nitrophenyl CH CH CH HH 2,6·Dimethylidene heptafluoroisopropyl Phenyl 4-12 2-trifluoromethylphenyl CH CH CH H H 2,6-dimethyl-4-heptafluoroisopropylphenyl 4-13 4-decyloxyphenyl CH CH CH CH HH 2,6-dimethyl -4-heptafluoroi-isopropylphenyl 4-14 2-(ethenylamino)phenyl CH CH CH HH 2,6-dimethyl-4-heptafluoroisopropylphenyl 4-15 2,4-Difluorophenyl CH CH CH CH HH 2,6-Dimethyl-4-heptafluorophenyl 4-16 2,3,4,5,6-pentafluorophenyl CH CH CH CH HH 2,6-dimethyl-4-heptafluoropropylphenyl 4-17 ° ratio. -2--2-yl CH CH CH CH HH 2,6-dimethyl-4-seven isopropylphenyl 4-18 σ 定 -3 -yl CH CH CH CH HH 2,6-dimethyl- 4-heptafluoroisopropylphenyl 4-19 ton -4-yl CH CH CH CH HH 2,6-dimethyl-4-heptafluoropropanyl phenyl 4-20 2- disorder -3-based CH CH CH CH [HH 2,6-dimethyl-4-seven isopropylphenyl 107 200836629 Table 3 (2) Chemicals Do not number Qi A9! a, 2 A, 3 A'4 Ri r2 〇2 4-21 2-gas ϋ 口 -3- -3- CH CH CH CH HH 2, dimethyl benzene hexafluoroisopropyl phenyl 4-22 Ν, oxygen 4 hr0tb mouth -2- CH CH CH CH HH -2,6-dimethyl basic heptafluoroi-isopropylphenyl 4-23 methyl CH CH CH CH H 2 2,6·didecyl 4»heptafluoroisopropylphenyl 4- 24 Methyl CH CH CH CH H 2,6-Dimethyl·4»heptafluoroisopropylphenyl 4-25 Ethyl CH CH CH H H 2,6·Dimethyl carheptafluoroisopropylbenzene Base 4-26 Ethyl CH CH CH CH H H 2,6·Dimethyl ice heptafluoroisopropylphenyl 4-27 2 2-trifluoroethyl CH CH CH CH HH 2,6>Dimethyl Winter sylvestre isopropylphenyl 4-28 2^-trifluoroethyl CH CH CH CH H 2,6> dimethyl car heptafluoroisopropylphenyl 4-29 vinyl CH CH CH CH HH 2 Know Dimethyl Ice Heptafluoroisopropylphenyl 4-30 Vinyl CH CH CH CH Me H 2,6~Dimethyl 1heptafluoroisopropylphenyl 4-31 propyl CH CH CH CH HH 2,6·Dimethyl 4»heptafluoroisopropylphenyl 4-32 propyl CH CH CH CH H 2,6·dimethylso-heptafluoroisopropylphenyl 4-33 Propyl CH CH CH CH HH 2,6~Dimethyl 4»seven isopropylphenyl 4-34 benzyl CH CH CH CH HH 2,6· dimethyl winter seven isopropyl phenyl 4- 37 phenyl CH CH CH H H 2 2 bromofluorene 6·bis(trifluoromethyl)phenyl 4-38 phenyl CH CH CH H H 2,4·bis(trifluoromethyl)phenyl 4-39 phenyl CH CH CH CH HH 2-bromo(heptafluoroisopropyl)>6«(mercaptosulfonyl-phenyl 440 phenyl CH CH CH HH 2,6-dibromo-p-n-n-propylthio)phenyl 441 benzene CH CH CH CH HH 2, Fu 2^4«(heptafluoro-n-propyl sulphate _phenyl 442 phenyl CH CH CH HH 2,6· dimethyl car (nonafluoro τ2-butyl) phenyl 108 200836629 Table 3 (3) Correction No. Qi A5! a, 2 A, A54 Ri Ri Qi 443 Phenyl CH CH CH CH HH 2,6>Dibromo^ (Imaginary)-Hexafluoropropoxy Group 444 Phenyl CH CH CH CH HH 2-bromo winter (1,1 and 3,3,3-six Fluoropropoxy>·6·nonylphenyl 445 phenyl CH CH CH HH 6->Smelly-8-seven isopropyl hydrazine 1 lea-5-yl 446 phenyl CH CH CH CH HH 2 , ketone dimethyl 4 < 2 · bromotrifluoro-1-trifluoromethyl ethyl) phenyl 447 phenyl CH CH CH H H 2,6 · dichlorotrifluorotrifluoromethyl phenyl phenyl 448 Phenyl CH CH CE CH HH 2,6·dichlorotetrafluoromethylphenyl 449 phenyl CH CH CH HH 2, Φ dibromotrifluoromethylphenyl abundance 50 phenyl CH CH CH CH HH 2 _Bromo 4,6>bis(trifluoromethyl)phenyl abundance 51 phenyl CH CH CH H H 2 2, Φ bis(trifluoromethyl)phenyl 4-52 phenyl CH CH CH HH 2-> Stinky ~6-(2,2-di-gas-1-difluoro-methyl ethoxy group 唆 唆 each base formula (C)
R1 ^ /Qi NR1 ^ /Qi N
109 200836629 表 4(1) 化合物 編號 Qi A、 a,2. A,3- A,4: Ri r2 Q2 5-1 苯基 CH CH丨 CHi CH H H : 2,6-二甲基-4-七氟異丙基苯基 5-2 2-甲基苯基 CH CH丨 CH丨 CH H H : 2,6-二甲基4-七氟異丙基苯基 5-3 2-氟苯基 CH CH丨 CH丨 CH H H : 2,6-二甲基-4-七氣異丙基苯基 5-4 3-敗苯基 CH CH CH CH H H : 2,6-二甲基-4-七氟i異丙基苯基 5-5 4-溴苯基 CH CH CH CH H H 2,6-二曱基-4-七氣異丙基苯基 5-6 2-碘苯基 CH CH CH CH H H 2,6-二甲基-4-七氣異丙基苯基 5-7 4-氰基苯基 CH CH CH CH H H 2,6-二甲基-4-七氣異丙基苯基 5-8 2-硝基苯基 CH CH CH CH H H 2,6-二甲基-4-七象異丙基苯基 5-9 4-硝基苯基 CH CH CH CH H H 2,6-二曱基-4-七氣異丙基苯基 5-10 2-胺基苯基 CH CH CH CH Π H 2,6-二曱基_4-七氟異丙基苯基 5-11 4-胺基苯基 CH CH CH CH H H 2,6-二曱基-4-七氟異丙基苯基 5-12 3-三氟甲基苯基 CH CH CH CH H H 2,6-二甲基-4-七亂異丙基苯基 5-13 2-(乙醯基胺基)苯基 CH CH CH CH H H 2,6-二甲基-4-七氟異丙基苯基 5-14 4-(乙醯基胺基)苯基 CH CH CH CH H H 2,6-二甲基-4-七氣異丙基苯基 5-15 2,4-二氣苯基 CH CH CH CH :H H 2,6-二甲基-4-七氣異丙基苯基 5-16 °比。定-2-基 CH CH CH CB :H H 2,6-二甲基-4-七氣異丙基苯基 5-17 0比。定-3-基 CH CH CH CH [H H 2,6-二曱基-4-七氣異丙基苯基 5-18 °比0定-4-基 CH CH CH CH [H H 2,6-二甲基-4·七氟^異丙基苯基 5-19 2-氟吼啶-3-基 CH CH CH CH [H H 2,6-二甲基-4-七氟異丙基苯基 5-20 2-氯0比°定-3-基 CH CH CH CB [H H 2,6-二甲基-4-七氣異丙基苯基 110 200836629 表 4(2) 化射勿 編號 Qi A9! a’2 A,3 A,4 Ri r2丨 Q2 5-21 6~>臭0比口定-2_基^ CH CH CH CH H H : 2,6-二曱基冬七氟異丙基苯基 5-22 N-彰tr吻定-2-基 CH CH CH CH H H 2,6»二甲基车七氟異丙基苯基 5-23 5-胺基似4]噚二, -3-基 CH CH CH CH H H 2,6-二甲基-4·七氣異丙基苯基 5-24 3-胺基似4]噚二, •5-基 CH CH CH CH Π H 2,6~二甲基-4-七氣異丙基苯基 5-25 5-胺基-2H似4]三 口坐-3-基 CH CH CH CH H H 2,6-二曱基-4-七氣異丙基苯基 5-33 1-苯基乙基 CH CH CH CH Me H 2,孚二曱基车七1異丙基苯基 5-34 苯基 CH CH CH CH H Me 孓溴4,6«雙(三氟甲基)苯基 5-35 苯基 CH CH CH CH H H 2,Φ雙(三氟曱基)苯基 5-36 苯基 CH CH CH CH H H 2-溴车(七氟異丙基曱基石黃_苯基 5-37 苯基 CH CH CH CH H H 2,6-二溴-4»(七氟JL丙基硫)苯基 5-38 苯基 CH CH CH CH H H 2,6>二漠-4-(七liL丙基亞石黃醯基)苯基 5-39 苯基 CH CH CH CH ;H H 2,6~二甲基-4«(九氣-2-丁基)苯基 5-40 苯基 CH CH CH CH TT ‘XI H 2,6«二溴4~(1,152,3,33-六氟丙基氧)苯基 111 200836629 表 4(3) 化執勿 編號 (¾ A’i A’2 A’3 A 氏 R2 Q2 541 m CH CH CH CH Η H 2-溴丙基氧甲基苯基 542 苯基 CH CH CH CH Η Η 543 m CH CHCHCH η[η 2,6-二曱基土氟小三敗曱基乙基>苯基 544 苯基 CH CH CH CH Η Η 545 笨基 CH CH CH CH| Η | Η 546 三氟曱基乙氧基)苯基 2,6~一ίΙτ4-三氣甲基苯基 2,Φ二演^1 三氟曱基苯基109 200836629 Table 4(1) Compound No. Qi A, a, 2. A, 3- A, 4: Ri r2 Q2 5-1 Phenyl CH CH丨CHi CH HH : 2,6-Dimethyl-4-7 Fluoroisopropylphenyl 5-2 2-methylphenyl CH CH丨CH丨CH HH : 2,6-dimethyl 4-heptafluoroisopropylphenyl 5-3 2-fluorophenyl CH CH丨CH丨CH HH : 2,6-dimethyl-4-seven isopropylphenyl 5-4 3-phenylphenyl CH CH CH H H : 2,6-dimethyl-4-septafluoro Propylphenyl 5-5 4-bromophenyl CH CH CH HH 2,6-diamidino-4-heptafluorophenyl 5-6 2-iodophenyl CH CH CH H H 2,6 - dimethyl-4-seven isopropylphenyl 5-7 4-cyanophenyl CH CH CH HH 2,6-dimethyl-4-seven isopropylphenyl 5-8 2- Nitrophenyl CH CH CH CH HH 2,6-Dimethyl-4-seven isopropylphenyl 5-9 4-nitrophenyl CH CH CH CH HH 2,6-dimercapto-4- Hexaqi isopropylphenyl 5-10 2-aminophenyl CH CH CH CH Π H 2,6-dimercapto_4-heptafluoroisopropylphenyl 5-11 4-aminophenyl CH CH CH CH HH 2,6-dimercapto-4-heptafluoroisopropylphenyl 5-12 3-trifluoromethylphenyl CH CH CH HH 2,6-dimethyl-4-seven isopropyl Phenylphenyl 5-13 2-(ethyl hydrazine Amino)phenyl CH CH CH H H 2,6-dimethyl-4-heptafluoroisopropylphenyl 5-14 4-(ethenylamino)phenyl CH CH CH H H 2,6- Dimethyl-4-seven isopropylphenyl 5-15 2,4-diphenylphenyl CH CH CH :HH 2,6-dimethyl-4-seven isopropylphenyl 5-16 ° ratio. Ding-2-yl CH CH CH CB : H H 2,6-dimethyl-4-seven isopropylphenyl 5-17 0 ratio. Ding-3-yl CH CH CH CH [HH 2,6-dimercapto-4-seven isopropylphenyl 5-18 ° ratio 0 -4--4-CH CH CH CH [HH 2,6-II Methyl-4·heptafluoro-isopropylphenyl 5-19 2-fluoroacridin-3-yl CH CH CH CH [HH 2,6-dimethyl-4-heptafluoroisopropylphenyl 5- 20 2-Chloro 0 ratio °-3-yl CH CH CH CB [HH 2,6-dimethyl-4-seven isopropylphenyl 110 200836629 Table 4 (2) Deuteration not numbered Qi A9! a '2 A,3 A,4 Ri r2丨Q2 5-21 6~>Smelly 0 is more than -2_ base ^ CH CH CH CH HH : 2,6-dimercapto winter sevoflurane 5-22 N-张tr吻定-2-基CH CH CH CH HH 2,6»Dimethyl carheptafluoroisopropylphenyl 5-23 5-amino group 4]噚2, -3-yl CH CH CH CH HH 2,6-Dimethyl-4·heptafluorophenyl 5-24 3-Amino-like 4]噚2, • 5-based CH CH CH CH Π H 2,6~2 Methyl-4-heptafluorophenyl 5-25 5-amino-2H-like 4]tri-n-yl-3-CH CH CH CH HH 2,6-dimercapto-4-heptafluoroisopropyl Phenyl 5-33 1-phenylethyl CH CH CH CH H H, oxadicarbyl 7-isopropylphenyl 5-34 phenyl CH CH CH CH H Me bromo 4,6 «double ( Trifluoromethyl)phenyl 5-35 phenyl CH CH CH CH HH 2, Φ bis(trifluoromethyl)phenyl 5-36 phenyl CH CH CH HH 2-bromo cartas(heptafluoroisopropyl fluorenyl phenyl) 5-phenyl phenyl CH CH CH H H 2 6-Dibromo-4»(heptafluoroJL propyl thio)phenyl 5-38 phenyl CH CH CH HH 2,6> Erqin-4-(seven liL propyl sulphate) phenyl 5-39 Phenyl CH CH CH CH ;HH 2,6-dimethyl-4«(nine gas-2-butyl)phenyl 5-40 phenyl CH CH CH TT 'XI H 2,6«dibromo 4~ (1,152,3,33-hexafluoropropyloxy)phenyl 111 200836629 Table 4 (3) No number (3⁄4 A'i A'2 A'3 A's R2 Q2 541 m CH CH CH CH Η H 2-Bromopropyloxymethylphenyl 542 Phenyl CH CH CH CH Η 543 543 m CH CHCHCH η[η 2,6-Dimercaptofluoride tris(sulfonylethyl)>Phenyl 544 phenyl CH CH CH CH Η 545 545 Stupid CH CH CH CH| Η | Η 546 trifluoromethyl ethoxy) phenyl 2,6~1 Ι Ι 4- 4-trimethylphenyl 2, Φ bis ^1 trifluoroanthracene Phenyl
5-53 苯基 CH CH CH CH Η 5-54 苯基 CH CH CH CH Η j:邊;4,6-雙(三氟曱;5-53 phenyl CH CH CH CH Η 5-54 phenyl CH CH CH CH Η j: side; 4,6-bis(trifluoromethane;
處所示 112 200836629 表5⑴Shown 112 200836629 Table 5(1)
化合物編號 物性値 i 卜1 H-NMR(DMS〇-d6) d 7.51-7.62(4H, m), 7.78(1 H, d, J = ?.8Hz), 7.97~8.00(2H, m), 8.05-8O8(2H, m), 8.30(1 H, d, J = Z.4Hz), 8.37 ΊΗ, d, J = 2.0Hz), 10Λ8(1Κ s), 10.65C1H, s). " 1-159 H-NMR(GDQ13) $ 3.47C3H s), 7.12-7.18(ZH, m), 7.21-7.32 :5H,m),7.70(1 H, s), 7.72(1 H, t J = 7.8Hz), 7.82-7.83(2H, m), 8.56(1 H, s). 1-163 H-NMR(CDGi3) d 3.57(3H, s), 7.11-7.14(1 H, m), 7.40-7.41 (2H, m), 7.58(1 H, d, J = 7.8Hz), 7.69-7.78(2H m), 7.91-8.02 (3H? m); 8.24(1 H, d( J = 4,9Hz), 1-264 lH-NMR(CDOl3) & 7.49-7.63(4H, m), 7.70-7.73(1 H, m), 7.76 (1H, d, J = 2OHz), 7.86-7.93(3H, m), 7.9δ-δ.02(3Η, m), 8.23 (1K t J = 2.0Hz). 1-265 iH-NMF^DMSO-cya 7,52-7.64(4H, m), 7.79(1H, d, J 二 7.8Hz), 7.97-8.02(3H, m), 8.06-8.09(1 H, m), 8.21 (1H, d, J = 2.0Hz), 8.38 (1H, t, ϋ = 2.0Hz), 10.48(1H, s), 10.60(1H, broad). 1-266 i H-NMFKDMSO-ds) § 7.53-7,64(4H, m), 7.81(1H, d, J 二 7.8Hz), ?.B9-8.10(7H, m), δ.1δ(1Η, s), 8.27(1H, d, J = 2.0Hz), 8.41(1H, s), 10.50(1H, s), 10.75(1H, s). 1 一 267 !H-NMR(CDCl3) d 7.35(1H, d, J = 7.3Hz), 7.5〇-7.63(7H, m), 7.72-7.80(3H, m), 7.89-7.92(2H, m), 8.00(1H, s), 8.05-8.10 (2H, m), 8.22(1 H, t. J = 2.0Hz). 1-303 'H-NMRCDMSO-de) $ 7.48-7.67(4H, m), 7.78(1H, dd, J = 4.4ΛΒΗΖ), 7.9t(1H, d, J = 7.8Hz), B.00-8.03(2HS m), 8.12-8.17 (1H, m), 8.46-8.50(3H, m), 9.08(1H, dd, J = 2.0,4.4Hz), 10.54 (1H, s), 10.84(1^ s). 卜304 lH-NMR(DIVlS〇-d6) δ 7.33-7.40(2H, m), 7.57-7.63(2H, m), 7.68-7J3(1H? m), 7J7(1H, ddf J = 3.93.8Hz), 7.B〇i1Ht d, J = ?.8Hz), 8.03(1 H, d, J = 7.8Hz)} B.41-B.49(3H, m), 9.08(1 H, dd, J = 1.5, 3.9Hz), 10.70( 1H, s), 10.84(1 H; s). ' 1-305 lH-NMR(DMS〇-d6) (5 7.64(1H, t, vJ = 7.8Hz), 7.77(1H, dd, J = 3_93·8Ηζ), 7.95(1 Hs 二 7.8Hz), 8.13(1 H, d, J = 7.8Hz), 8.24C2H, d, J = δ.3Ηζ), 8.39-8.50(5Η, m), 9.08(1 H, dd, J = 1.5,3.9Hz), 10.84( 1H, si 10.85(1 H, s).Compound number physical properties 値i 1 H-NMR (DMS〇-d6) d 7.51-7.62(4H, m), 7.78(1 H, d, J = ?.8Hz), 7.97~8.00(2H, m), 8.05 -8O8(2H, m), 8.30(1 H, d, J = Z.4Hz), 8.37 ΊΗ, d, J = 2.0Hz), 10Λ8(1Κ s), 10.65C1H, s). " 1-159 H-NMR (GDQ13) $ 3.47C3H s), 7.12-7.18 (ZH, m), 7.21-7.32: 5H, m), 7.70 (1 H, s), 7.72 (1 H, t J = 7.8 Hz), 7.82-7.83(2H, m), 8.56(1 H, s). 1-163 H-NMR(CDGi3) d 3.57(3H, s), 7.11-7.14(1 H, m), 7.40-7.41 (2H, m), 7.58 (1 H, d, J = 7.8 Hz), 7.69-7.78 (2H m), 7.91-8.02 (3H? m); 8.24 (1 H, d ( J = 4, 9 Hz), 1-264 lH-NMR(CDOl3) & 7.49-7.63(4H, m), 7.70-7.73 (1 H, m), 7.76 (1H, d, J = 2OHz), 7.86-7.93 (3H, m), 7.9δ- Δ.02(3Η, m), 8.23 (1K t J = 2.0Hz). 1-265 iH-NMF^DMSO-cya 7,52-7.64(4H, m), 7.79(1H, d, J 7.8Hz ), 7.97-8.02(3H, m), 8.06-8.09(1 H, m), 8.21 (1H, d, J = 2.0Hz), 8.38 (1H, t, ϋ = 2.0Hz), 10.48(1H, s ), 10.60(1H, broad). 1-266 i H-NMFKDMSO-ds) § 7.53-7,64(4H, m), 7.81(1H, d, J two 7.8Hz), ?.B9-8.10(7H , m), δ.1δ(1Η, s), 8.27(1H, d, J = 2.0Hz), 8.41(1H, s), 10.50(1H, s), 10.75(1H, s). 1 267 !H-NMR(CDCl3) d 7.35(1H, d, J = 7.3Hz), 7.5〇-7.63(7H, m), 7.72-7.80 (3H, m), 7.89-7.92(2H, m), 8.00(1H, s), 8.05-8.10 (2H, m), 8.22(1 H, t. J = 2.0Hz). 1-303 'H- NMRCDMSO-de) $ 7.48-7.67(4H, m), 7.78(1H, dd, J = 4.4ΛΒΗΖ), 7.9t(1H, d, J = 7.8Hz), B.00-8.03(2HS m), 8.12 -8.17 (1H, m), 8.46-8.50(3H, m), 9.08(1H, dd, J = 2.0, 4.4Hz), 10.54 (1H, s), 10.84(1^ s). Bu 304 lH-NMR (DIVlS〇-d6) δ 7.33-7.40(2H, m), 7.57-7.63(2H, m), 7.68-7J3(1H? m), 7J7(1H, ddf J = 3.93.8Hz), 7.B〇 i1Ht d, J = ?.8Hz), 8.03(1 H, d, J = 7.8Hz)} B.41-B.49(3H, m), 9.08(1 H, dd, J = 1.5, 3.9Hz) , 10.70( 1H, s), 10.84(1 H; s). ' 1-305 lH-NMR(DMS〇-d6) (5 7.64(1H, t, vJ = 7.8Hz), 7.77(1H, dd, J = 3_93·8Ηζ), 7.95 (1 Hs = 7.8 Hz), 8.13 (1 H, d, J = 7.8 Hz), 8.24C2H, d, J = δ.3Ηζ), 8.39-8.50(5Η, m), 9.08 (1 H, dd, J = 1.5, 3.9 Hz), 10.84 ( 1H, si 10.85 (1 H, s).
113 200836629 表 5(2)113 200836629 Table 5 (2)
化刮勿編號 物性値 1-306 H-NMR(DMS〇-d5) 5 10.5 (1Hf s), 9.85 (1H} s), 8.36 (1H, t J=1.5 Hz),7J8—8Ό7 (3H,m),7.75 (1H,d, J二7.8 Hz), 150— 7.63 (4H, m). 7.42 (2H, s), Z.30 (6HS s). 1-307 H-NMR(CDC!3) ¢4.76-4.82 (1H, m), 7.15 (2H, s), 7.45-8.17 (10H, m), 8.30 (1H, brs). 1-308 H-NMR(CDGi3) (54.78-484 (1K m)? 7.19 (2H, s), 7.33-8.66 (10H m). 1-309 ‘H-NMFKDMSCHiy δ 7.53-7·63(4Η,m),7.79(1H, d,J = 7.8Hz), 7.9B-8.02(2H, m), 8.08(1H, dd? J = 1.5,7.8Hz), 8.18(1H, s), 8.39(1 H, t, vi = 1.5Hz), 10.50(1 H, s), 10.56(1 H, s). 1-310 'H-NMRiCDCIs) § ?.19-7.25(1HS m), 7.35(1H, t, ϋ = 7.8Hz)t 7.51-7,60(3Hf m), 7.76-7.78(2H, m), 7.92(1 H, d, J = 7.8Ης), 8.19(1H, d, J = 7.8Hz), 8.34(1Η, s), B.63(1H, d, J = 16.1Hz). 1-311 'H-NMRCDMSO-^) δ 7.37-7.4K2H, m), 7.56(1H, t, J = 7.8Hz), 7.79(1H,d, J = 7.8Hz), 8·06-8.14(3H, m), 8.18(1H,s), 8.36(1 H, s), 10.51(1 H, s), 10.56(1 H, s). H rsH rs Ι^ΟΙΔ W-NMRODMSO-cy δ 7.60(1H, d,J 二 6.8Hz), 7,83(1H, d5 J _ rs t \ #% Λ j * t i » -nr% ii \ <v #-v \ rv λ ^ -ο.οπζΛ c.uyun, α, u = ι.όηζ), e. i d-c.zo\4rt, m;, 5.4U (2H, d, J = 8.8Hz), 10.59OH, s), 10.81(1H? s). 1-313 'H-NMRCDMSO-dg) ά 7.53-7.64(4H, m), 7.77(1H5 d, J = 7.8Hz), 7.97-8.01 (3H, m), 8.07(1 H, dd, J = 1.5,7.8Hz), 8.41 (1H, s\ 10.49(1H, s), 10.52(1H, s). 1-314 lH-NMR(DMS〇-d5) δ 7.33-7.40(2H, m), 7.54-7.63(2R m), 7.68-7.72(1 H, m), 7.78(1 H, d, J = 7.8Hz), 7.98(1 Ht d, J = 8.3Hz), 8.10C2K s), 8.36(1H, s), 10.62(1K s), 10.67(1H, s). 1-315 ^H-NMRCDMSO-de) δ 7.25-7.30(2H, m), 7.56-7.65(2H, m), 7.80(1 H, df J = 8.3Hz), 7.92-7.95(1 Ht m), 8.10(2H, s), 8.32 (1H, sX 10.65(1 H, s), 11.06(1Hs), 1-316 lH-NIVlR(DMS〇-d6) δ 7.52-7.63(4HT m), 7.72(1H, d} J = 7.8Hz), 7.98-8.01 (2H? m), 8.05-8.07(2H, m), 8.34(1 H, t J = 2.0Hz), 8.44(1 H, d, J = 2.0Hz). 10,40(1 H. s), 10.48(1 H, s). 1-317 MS(APCI)=604(iVi-H) 1-318 MS(APGI)=604(M+1) 1-319 IVIS(APGI)=685(M+1) 1-320 MS(APCI)=586(M+1) . ^ | 化合物編號 物性値 1-321 MS(APCI)=645(M+1) 1-322 MS(APGI)=685(M+1) ‘1-323 MS(APGD:聊⑽+1) 1-324 _S(APO!)=601(_) 1-325 IMS(APGI)=530(M-M) 1-326 iMS(APCI)=63t(M+1) 1-327 MS(APGI)=642(M+1) 1-328 MS(AFCI)=542(M+1) 1-329 MS(APOI)=610(M-fl) 1-330 MS(APC1)=547 ⑽+1) 1-331 MS(APGI)=571(M+1) 1-332 IMS(APCI)=633(IV1+1) 1-333 MS(APOI)=582(M+t) 1-334 MS(APGI)=592(M-i-1) 、 1-335 MS(APCI)=668(lVi+l) 114 200836629 表5⑷ 化#tJ編號 物性値 1-336 MS(APCI)=591(M+1) 1-337 MS(APCI)=641(M+1) 1-338 MS(APCI)=642(iV!+1) 1-339 lH-NMR(DMS〇-d6) δ 7.53-7.63(4H; m), 7.75(1 H5 d, J = 7.8Hz), 7.98-B.09(3H, m), 8.20(1 H, s), 8.37(1 H, s), 8.6ΚΊΗ, s), 10.50(1H, s)? 10.64(1H, s). 1-340 'H-NMRCDMSO-dg) $ 7.53-7.64(4H, m), 7.70-7.73(1 H, m), 7.87(1H, d, J = δ.3Ηζ), 7.98-8O7(3H, m), δ.13-δ.17(2Η, m), 8.38(1 H? t J = 1.7Hz), 10.40(1 H, s), 10.50(1 H, s). 1-341 MS(APCIM78(M+1) 1-342 MS(APa)=489_1) 1-343 MS(APCI)=4B9(M+1) 1-344 MS(APCI)=507(M+1) 1-345 MS(APCI)=487(!Vi+1) 1-346 MS(APGI)=52KM+1) 1-347 MS(APGi)=534(M+D 1-348 MS(APCI)=485(M^1) 1-349 IV1S(APCI)=467(M+1) 1-^350 |MS(APOi)=4S1(M+1)No. 3061-30 H-NMR (DMS〇-d5) 5 10.5 (1Hf s), 9.85 (1H} s), 8.36 (1H, t J=1.5 Hz), 7J8—8Ό7 (3H,m ), 7.75 (1H, d, J 7.8 Hz), 150-7.63 (4H, m). 7.42 (2H, s), Z.30 (6HS s). 1-307 H-NMR (CDC!3) ¢ 4.76-4.82 (1H, m), 7.15 (2H, s), 7.45-8.17 (10H, m), 8.30 (1H, brs). 1-308 H-NMR(CDGi3) (54.78-484 (1K m)? 7.19 (2H, s), 7.33-8.66 (10H m). 1-309 'H-NMFKDMSCHiy δ 7.53-7·63(4Η,m), 7.79(1H, d,J = 7.8Hz), 7.9B-8.02 (2H, m), 8.08 (1H, dd? J = 1.5, 7.8 Hz), 8.18 (1H, s), 8.39 (1 H, t, vi = 1.5 Hz), 10.50 (1 H, s), 10.56 ( 1 H, s). 1-310 'H-NMRiCDCIs) § ?.19-7.25(1HS m), 7.35(1H, t, ϋ = 7.8Hz)t 7.51-7,60(3Hf m), 7.76-7.78 (2H, m), 7.92(1 H, d, J = 7.8Ης), 8.19(1H, d, J = 7.8Hz), 8.34(1Η, s), B.63(1H, d, J = 16.1Hz 1-311 'H-NMRCDMSO-^) δ 7.37-7.4K2H, m), 7.56(1H, t, J = 7.8Hz), 7.79(1H,d, J = 7.8Hz), 8·06-8.14 (3H, m), 8.18(1H, s), 8.36(1 H, s), 10.51(1 H, s), 10.56(1 H, s). H rsH rs Ι^ΟΙΔ W-NMRODMSO-cy δ 7.60 (1H, d, J two 6.8Hz), 7,83(1H, d5 J _ Rs t \ #% Λ j * ti » -nr% ii \ <v #-v \ rv λ ^ -ο.οπζΛ c.uyun, α, u = ι.όηζ), e. i dc.zo\4rt , m;, 5.4U (2H, d, J = 8.8Hz), 10.59OH, s), 10.81(1H? s). 1-313 'H-NMRCDMSO-dg) ά 7.53-7.64(4H, m), 7.77 (1H5 d, J = 7.8 Hz), 7.97-8.01 (3H, m), 8.07 (1 H, dd, J = 1.5, 7.8 Hz), 8.41 (1H, s\ 10.49(1H, s), 10.52 ( 1H, s). 1-314 lH-NMR (DMS〇-d5) δ 7.33-7.40 (2H, m), 7.54-7.63 (2R m), 7.68-7.72 (1 H, m), 7.78 (1 H, d, J = 7.8 Hz), 7.98 (1 Ht d, J = 8.3 Hz), 8.10 C2K s), 8.36 (1H, s), 10.62 (1K s), 10.67 (1H, s). 1-315 ^H -NMRC DMSO-de) δ 7.25-7.30 (2H, m), 7.56-7.65 (2H, m), 7.80 (1 H, df J = 8.3 Hz), 7.92-7.95 (1 Ht m), 8.10 (2H, s ), 8.32 (1H, sX 10.65(1 H, s), 11.06(1Hs), 1-316 lH-NIVlR(DMS〇-d6) δ 7.52-7.63(4HT m), 7.72(1H, d} J = 7.8 Hz), 7.98-8.01 (2H? m), 8.05-8.07(2H, m), 8.34(1 H, t J = 2.0Hz), 8.44(1 H, d, J = 2.0Hz). 10,40( 1 H. s), 10.48(1 H, s). 1-317 MS(APCI)=604(iVi-H) 1-318 MS(APGI)=604(M+1) 1-319 IVIS(APGI)= 685(M+1) 1-320 MS(APCI)=586(M+1) . ^ | Compound Number Physical Properties 値1-321 MS(APCI)=645(M+1) 1-322 MS(APGI)=685(M+1) '1-323 MS(APGD:聊(10)+1) 1-324 _S(APO!)=601(_ 1-325 IMS(APGI)=530(MM) 1-326 iMS(APCI)=63t(M+1) 1-327 MS(APGI)=642(M+1) 1-328 MS(AFCI)=542 (M+1) 1-329 MS(APOI)=610(M-fl) 1-330 MS(APC1)=547 (10)+1) 1-331 MS(APGI)=571(M+1) 1-332 IMS (APCI)=633(IV1+1) 1-333 MS(APOI)=582(M+t) 1-334 MS(APGI)=592(Mi-1) , 1-335 MS(APCI)=668(lVi +l) 114 200836629 Table 5(4) Chemical #tJ号性性値1-336 MS(APCI)=591(M+1) 1-337 MS(APCI)=641(M+1) 1-338 MS(APCI)=642 (iV!+1) 1-339 lH-NMR(DMS〇-d6) δ 7.53-7.63(4H; m), 7.75(1 H5 d, J = 7.8Hz), 7.98-B.09(3H, m) , 8.20(1 H, s), 8.37(1 H, s), 8.6ΚΊΗ, s), 10.50(1H, s)? 10.64(1H, s). 1-340 'H-NMRCDMSO-dg) $ 7.53- 7.64(4H, m), 7.70-7.73(1 H, m), 7.87(1H, d, J = δ.3Ηζ), 7.98-8O7(3H, m), δ.13-δ.17(2Η, m ), 8.38 (1 H? t J = 1.7 Hz), 10.40 (1 H, s), 10.50 (1 H, s). 1-341 MS (APCIM78(M+1) 1-342 MS(APa)=489_1 1-343 MS(APCI)=4B9(M+1) 1-344 MS(APCI)=507(M+1) 1-345 MS(APCI)=487(!Vi+1) 1-346 MS(APGI )=52KM+1) 1-3 47 MS(APGi)=534(M+D 1-348 MS(APCI)=485(M^1) 1-349 IV1S(APCI)=467(M+1) 1-^350 |MS(APOi)=4S1 (M+1)
表 5(5) 化合物編號 物性値 1-351 MS(APCI)=483(M+1) 1 - 352 MS(APOI)=483(M+1) 1-353 MS(APCI)=543(M+1) 1-354 MS(APGI)=503(M-M) 1-355 MS(AFCI)=503(M+1) 1-356 MS(APOI)=493(y+1) 1-357 MS(APGI)=488(IVi+1) 1-358 MS(APCI)=468(M-1) 1-359 IVIS(APCI)=488(M+1) 1-360 MS(APCI)=470(M+D 1-361 MS(APCI)=469(IV1+1) 1-362 MS(APGI)=455(iVl+l) 1-363 MS(APGI)=473〇Vt+1) 1-364 MS(APCI)=473(iVI+1) 1-365 'H-NMRCDMSO-ds) ά 7.53-7.73(5H,m), 7.93-8.09(6H?m), 8.38(1 HTdJ=2.0Hz), 10.4(1 H,s), 10.5(1 Ks). 115 200836629表5⑹Table 5 (5) Compound number physical properties 値 1-351 MS (APCI) = 483 (M + 1) 1 - 352 MS (APOI) = 483 (M + 1) 1-353 MS (APCI) = 543 (M+1) 1-354 MS(APGI)=503(MM) 1-355 MS(AFCI)=503(M+1) 1-356 MS(APOI)=493(y+1) 1-357 MS(APGI)=488 (IVi+1) 1-358 MS(APCI)=468(M-1) 1-359 IVIS(APCI)=488(M+1) 1-360 MS(APCI)=470(M+D 1-361 MS (APCI)=469(IV1+1) 1-362 MS(APGI)=455(iVl+l) 1-363 MS(APGI)=473〇Vt+1) 1-364 MS(APCI)=473(iVI+ 1) 1-365 'H-NMRC DMSO-ds) ά 7.53-7.73(5H,m), 7.93-8.09(6H?m), 8.38(1 HTdJ=2.0Hz), 10.4(1 H,s), 10.5( 1 Ks). 115 200836629 Table 5 (6)
--化合物號 物性値 1 1-366 、 H-NMR(DMS〇-d6) δ 7,53-7.63(4H, m), 7.74(1H, d, =7.8HzX 7.98-8.01 (2H, m), 8.07(1 H, dd, J = 1.5,7.8Hz), 8.18(1 HT s), 8.37(1 H, t ϋ = 1.5Hz), 8.51 (1H, d, J = 1.5Hz), 0.50(1 H, s), 10.62(1 H, s). 1 1-367 H-NMR( GDC!3,) (57.00-7.06C2H, m), 7.43-7.58(2H, m), 1JZ-1J9 (3H, m), 7.91-7.B3 (2H, m), 8.00 (1H, s), 8.26 1H, s). 1-368 H-NMR( ODCi3) ¢7.27-7.29 (1H, m), 7.54 (1H, t, J=8.3 Hz), 1.11 (IK d, J=8.3 Hz), 7.91 ClH, s)5 8.00 (1H, s), 8.21-8.34 ;5H, m), 8.91 (1H, s), 9.95 (1H, s). 1-36B H-NMR( DMS〇-d6) δ 2.32(3K,sX 7.52-?.63(5HTm), 7.76. ;1HfdJ=7.8Hz), 7.87(1 8.00(2Hfdd?J=1.5Hz, 7.8), 8.06(1 H,d,J=7.8Hz), 8.37(1 Ks), 1Q.18(1Ks), 10.47(1 Ks). 1-371 lH-NMR( DMS〇-d6) (5 2.32(3HTs),7.54-7.67.72-7.77(2^1^),7.98-8.08(3H?m)?8.37(l Ks)? 10.17( 1 Ks), 10.46(1 Ks). 1-372 ^-NM^ CDGl3) δ 2.32 (3H, s), 7.04-8.23 (14H, m). 1-373 lH-NMR(DMS〇-d6) δ 2.46(3H, s), 7.53-7.71 (6H, m)? 7.80 (1H, s), 7.90(1 H; d, J = 7.8Hz), 8.00-8.02(2Η, m), 8.ID-8.17 (2H, m), 8.38(1H, d, J = 7.8Hz), 8.45(1H, s), 10.5K1H s), 10.52(1 H, s). 1-374 lH^NMR(DMS〇-d6) δ 2.4δ(3Η} s), 7.33-7.40(2H, m), 7.57-7.63C2H, m), 7.66-7.?3(3H, m), 7.79(1H, s), 7.88-7.9K1H, m), 8.02(1 HT d, J = 7.8Hz), 8.10-8.12(1 H, m), 8.36-8.40(2H, m), 10.540H, s), 10.68(1H, s). 1-375 ^-NMRCDMSO-de) δ 2.04(2H, quint J = 7.3Hz), 2.91 (2H, t, J = 7.3Hz), 3.1K2H, dd, J = 7.3,12.2Hz), 7.40(1H, d, ϋ = 8.8Hz), 7.51-7,67(5H, m), 7.71 (1H, d, J = 7.8Hz), 7.98-8.07 (3H m), 8.35(1H, s), 10.10(1H, s), 10.48(1H. s). 1-376 lH-NMR(DMS〇-d6) δ 7.53-7.64(4H, m), 7.78(1 H, d? J = 7.8Hz), 7.99-8.02(2H, m), 8.08(1 H, dd J = 2.0?7.8Hz)? 8.32 (2H s), 8.40(1 H, t J = 2.0Hz), 10.5K1H, s), 10.66(1 H, s). 1-377 ιΗΗΜΐνΐΗ(00013) d2.33(6H,s), 7·18-7·38(5Η, m), 7.49-7.60 (5H( m), 7-72(1H, d, J=7.8Hz)f 7.87~7.96(3H, m), 8.10(1Η; s), 8.29(1 H, d, ϋ=Β.0Ηζ). 1-378 lH-NMR(CDCi3) 5Z.33(3H, s), 2.34(6H, s), 7O4(1H, t J=B.8Hz), 7.33-7.57(8H, m)f 7.77(1 Hu d, 8.00-8.02(2Ht m), 8.14(1 H, dd, B.3Hz), 8.36(1 HT t ϋ=2.0Ηζ), 8.81(1 H, s), 9.85(1 s). 1-379 'H-NMRCCDCIs) d2.29(6H, s), 6.67(1 H( s), 7.21 (2H, s), 7.47-7.59(6H, m), 7.7〇-7.72(2H( m)t 7.87-7.8^, m), 7.95(1 Ht d J=7.8Hz), 8.13(1H, s), 8.25(1H. s). 1-380 !H-NMR(CDC!3) 52.32(6H, s), 7.07-7.09(1 H, m), 7.27-7.29 (1H, m)t 7·37(2Η), 138-7·57(δΗ,m), 7.73-7J8(2H, m), 7.88 (1H, d, J=8.3Hz), 8.14C1H, s), 8.27(1H, s). 1-381 ' H-NMRCCDCis) $2.34(6H, s), 7.35-7.55(1 OH, m), 7.74-7.80 (2H, m), ?.89(tHf d, J=8.3Hz), 8.11(1H, s), δ.28(1Ητ s). 116 200836629- Compound No. 1-1 1-366, H-NMR (DMS〇-d6) δ 7,53-7.63(4H, m), 7.74(1H, d, =7.8HzX 7.98-8.01 (2H, m), 8.07 (1 H, dd, J = 1.5, 7.8 Hz), 8.18 (1 HT s), 8.37 (1 H, t ϋ = 1.5 Hz), 8.51 (1H, d, J = 1.5 Hz), 0.50 (1 H , s), 10.62(1 H, s). 1 1-367 H-NMR( GDC!3,) (57.00-7.06C2H, m), 7.43-7.58(2H, m), 1JZ-1J9 (3H, m ), 7.91-7.B3 (2H, m), 8.00 (1H, s), 8.26 1H, s). 1-368 H-NMR( ODCi3) ¢7.27-7.29 (1H, m), 7.54 (1H, t , J=8.3 Hz), 1.11 (IK d, J=8.3 Hz), 7.91 ClH, s)5 8.00 (1H, s), 8.21-8.34 ;5H, m), 8.91 (1H, s), 9.95 (1H , s). 1-36B H-NMR (DMS〇-d6) δ 2.32 (3K, sX 7.52-?.63 (5HTm), 7.76.; 1HfdJ=7.8Hz), 7.87 (1 8.00 (2Hfdd?J=1.5) Hz, 7.8), 8.06 (1 H, d, J = 7.8 Hz), 8.37 (1 Ks), 1Q.18 (1Ks), 10.47 (1 Ks). 1-371 lH-NMR ( DMS〇-d6) ( 5 2.32(3HTs), 7.54-7.67.72-7.77(2^1^), 7.98-8.08(3H?m)?8.37(l Ks)? 10.17( 1 Ks), 10.46(1 Ks). 1-372 ^-NM^ CDGl3) δ 2.32 (3H, s), 7.04-8.23 (14H, m). 1-373 lH-NMR(DMS〇-d6) δ 2.46(3H, s), 7.53-7.71 (6H, m ) 7.80 (1H, s), 7.90 (1 H; d, J = 7.8 Hz), 8.00-8.02 (2Η, m), 8.ID- 8.17 (2H, m), 8.38 (1H, d, J = 7.8Hz), 8.45(1H, s), 10.5K1H s), 10.52(1 H, s). 1-374 lH^NMR(DMS〇-d6 δ 2.4δ(3Η} s), 7.33-7.40(2H, m), 7.57-7.63C2H, m), 7.66-7.?3(3H, m), 7.79(1H, s), 7.88-7.9K1H , m), 8.02 (1 HT d, J = 7.8 Hz), 8.10-8.12 (1 H, m), 8.36-8.40 (2H, m), 10.540H, s), 10.68(1H, s). 375 ^-NMRC DMSO-de) δ 2.04 (2H, quint J = 7.3 Hz), 2.91 (2H, t, J = 7.3 Hz), 3.1K2H, dd, J = 7.3, 12.2 Hz), 7.40 (1H, d, ϋ = 8.8Hz), 7.51-7,67(5H, m), 7.71 (1H, d, J = 7.8Hz), 7.98-8.07 (3H m), 8.35(1H, s), 10.10(1H, s) , 10.48(1H. s). 1-376 lH-NMR(DMS〇-d6) δ 7.53-7.64(4H, m), 7.78(1 H, d? J = 7.8Hz), 7.99-8.02(2H, m ), 8.08(1 H, dd J = 2.0?7.8Hz)? 8.32 (2H s), 8.40(1 H, t J = 2.0Hz), 10.5K1H, s), 10.66(1 H, s). 1- 377 ιΗΗΜΐνΐΗ(00013) d2.33(6H,s), 7·18-7·38(5Η, m), 7.49-7.60 (5H(m), 7-72(1H, d, J=7.8Hz)f 7.87~7.96(3H, m), 8.10(1Η; s), 8.29(1 H, d, ϋ=Β.0Ηζ). 1-378 lH-NMR(CDCi3) 5Z.33(3H, s), 2.34( 6H, s), 7O4(1H, t J=B.8Hz), 7.33-7.57(8H, m)f 7.77(1 Hu d, 8.00-8.02(2Ht m), 8.14(1 H, dd, B.3Hz), 8.36(1 HT t ϋ=2.0Ηζ), 8.81(1 H, s), 9.85(1 s). 1-379 'H-NMRCCDCIs) d2.29(6H, s) , 6.67(1 H( s), 7.21 (2H, s), 7.47-7.59(6H, m), 7.7〇-7.72(2H( m)t 7.87-7.8^, m), 7.95(1 Ht d J= 7.8Hz), 8.13(1H, s), 8.25(1H.s). 1-380 !H-NMR(CDC!3) 52.32(6H, s), 7.07-7.09(1 H, m), 7.27-7.29 (1H, m)t 7·37(2Η), 138-7·57(δΗ,m), 7.73-7J8(2H, m), 7.88 (1H, d, J=8.3Hz), 8.14C1H, s) , 8.27(1H, s). 1-381 'H-NMRCCDCis) $2.34(6H, s), 7.35-7.55(1 OH, m), 7.74-7.80 (2H, m), ?.89(tHf d, J =8.3Hz), 8.11(1H, s), δ.28(1Ητ s). 116 200836629
化合物編號 物性値 1 1-382 2 H-NMR(DIVlS〇-d6) δ 1.23-1.39(5H, m), 1.57-1.71(5H, m), ..45-2.5K1H, m), 7.4〇-7.52(6Hs m), 7.66(1H, d, J = 7.8Hz)5 ?.85-7.97(3H, m), 8.23(1H, s), 10.17(1H, s), 10.37(TH s). 1 1-383 \ ( H-NyRCDMSO-c^) δ 1.20-1.40(5H, m), 1.67-1.79(5^ m), L45-Z50(1H, m), 7.19(2H, d, J = 8.8Hz), 7.47-7.6B(7H, m), ?.97-8.02(3H, m), B.29(1H, t J = ZOHz). 10.20(1H, s), 10.45 1H, s). 1-384 H-NMR(CDCi3) δ 2·19(6Η, s),7.00-7·09(2Η, m), 7.40-7.45 .3H, m), 7.53(1H, t, J=7.8HzX 7.63(1H, d, J=7.8Hz), 7,67(1H, s), ?.84(2HS d, J=7.8Hz), 7.95(1 H, dd, J=1.5, 7,8Hz), 8,18(1 H, s), 5.46(1 H, s). - 1-385 H-NMRCCDCb) 52.35(6H? s), 7.44-7.530H, m), 7.59(1 H, t J=7.8Hz), 7.72(1H, d, J=7.8Hz), 7.79-?.89(6H, m), 8.12(1H, s), B.36(1H, s). 1-386 H-NMR (CDCl3) d Z.33(6H, s), 4.11(1H, septet, J = 6.9Hz), 7.17C2H, s), 7.50-7.6K5H, m)f 7.7K1H, d, J = 7.8Hz), 7.87-7.90(3H, m), 8.03(1 H, s), 8.29( 1H, s). 1-387 1 H^NmRvGDClg) u 6.30 (1H, septet, J =6.8Hz), 7.01 (1H, d, J =8.8Hz)T 7.49-7.61 (4H, m), 7.68 (1H, dd, J =1.0,7.8Hz), 7.88-7.91 (2H, m)t 7.96-8.01 (2Ht m), 8.26 (1Ht t, J =1.9Hz), 8.33 (1H, s), 8.81 (1H, d, J =8.8Hz). 1-389 'H-NMRCCDGls) ά4.13(2Η, dt, J=6.4, 14.6Hz), 7.41-7.57(4H, m), 7.62(1 H, d, J=7.8Hz), 7.99-8.01 (2H, m), 8.09(2H, d, J=7.3Hz), , 8.Z2(1Ht t J=2.0Hz), 9.79(1H? s). 1-390 SH-NMR (CDGi3) δ 7.50-7.6K4H, m), 7,7δ(1Η, d, J = 7.8Hz), l.miH, d, J = 7.8HzX 7,93(1 H, s), 7.95(1 Ht s), 8.07(1 H, s), 8.10(1H, s), 8.33(^, s). 1-391 lH~NMR (GDCI3) δ 7.44(1H, dd, J = 4.9, 7.8Hz), ?.57(1H, t J = 7.8Hz), 7.79(1 H, d, J = 7.8Hz), 7.87-7.BK2H, m), 8.13 (1H, sX 8.23(1H, dd, J = 2.0, 7.8Hz), 8.3K1H, s), 8.42(1H, s)T 8.55(1 H, dd, J = 2.0, 4.9Hz). 1-392 'H-NMR (CDCi3) d 7.22(1Hf dd, J = 7.8, 12.2Hz), 7.35(1H, t,. J = 7.8Hz),7.53-7.60(2H,m),7.77(1H,d,J = 7.8Hz),7.90-7.92(2H, m), 8.13(1H, s)$ 8.19(1H? dt, J = 1-4, 7.8Hz), 8.34( 1H, s), 8.64(1H, d? J = 16.1Hz). 1-393 W-NiVlR(DMSO—4) d ?·31 -7.38(2H m),7·50-7.62(2Η,m), 7.66-7.72(4H, m), 7.92-7.96(3Η, m), 8.Z7(1H, s), 10,61(1H, s), 10.63(1 H, s). 1-394 'H-NMRCDMSO-dg) δ 7.32-7.38(2HT m)5 7.52-7.60C2H, m), 7.65-7.?3(2H m), 7.94(1H, d, J = 8.3Hz), 8.11(2H, d, J = 8.8Hz), 8.20-8.23(2H( m), 8.29(1H, s), 10.67(1H, s), 11.0K1H s). 1-395 lH-NMR(CDOI3) d7.45-7.62(6H, m)T 7.69(1H, d5 J=7.8Hz), 7.B3 (2H, d, J=7.3Hz), 8.01 (2H d, J=7.3H2), 8.14(1 H, d, J=7.8Hz), 8.28 (1H, t, J=1.9Hz), 9.95(1H, s), 9.99(1H, s). 1-396 lH-NMR (CDCI3) δ 7.44-7.6K5H, m), 7.73(1H, d, J = E.3Hz), 7.93(2H, d, J = 8.3Hz), 8.01 (2Hf d, J = 6.8Hz), 8.07-8.13(2Ht m), 8.29(1 H, si 9.97(1 H, s), 10.10(1 H, s). 1-397 'H-NMRCCDCls) d2.41(3H, s), ?.51~7.58(6H, m), 7.67(1H, d, J=6-.3HzX 7.86-7,9l(4H, m), 7.99(1H si 8.23(1H, d, J=8.3Hz), 8.30(1 H, t J=2.0HzX 117 200836629 4 5(8)Compound No. 物1 1-382 2 H-NMR (DIV1S〇-d6) δ 1.23-1.39 (5H, m), 1.57-1.71 (5H, m), ..45-2.5K1H, m), 7.4〇- 7.52(6Hs m), 7.66(1H, d, J = 7.8Hz)5 ?.85-7.97(3H, m), 8.23(1H, s), 10.17(1H, s), 10.37(TH s). 1 1-383 \ ( H-NyRCDMSO-c^) δ 1.20-1.40(5H, m), 1.67-1.79(5^m), L45-Z50(1H, m), 7.19(2H, d, J = 8.8Hz ), 7.47-7.6B(7H, m), ?.97-8.02(3H, m), B.29(1H, t J = ZOHz). 10.20(1H, s), 10.45 1H, s). 1- 384 H-NMR (CDCi3) δ 2·19(6Η, s), 7.00-7·09(2Η, m), 7.40-7.45 .3H, m), 7.53(1H, t, J=7.8HzX 7.63(1H , d, J=7.8Hz), 7,67(1H, s), ?.84(2HS d, J=7.8Hz), 7.95(1 H, dd, J=1.5, 7,8Hz), 8,18 (1 H, s), 5.46 (1 H, s). - 1-385 H-NMRCCDCb) 52.35 (6H? s), 7.44-7.530H, m), 7.59 (1 H, t J = 7.8 Hz), 7.72 (1H, d, J = 7.8 Hz), 7.79-?.89 (6H, m), 8.12 (1H, s), B.36 (1H, s). 1-386 H-NMR (CDCl3) d Z .33(6H, s), 4.11(1H, septet, J = 6.9Hz), 7.17C2H, s), 7.50-7.6K5H, m)f 7.7K1H, d, J = 7.8Hz), 7.87-7.90(3H , m), 8.03(1 H, s), 8.29( 1H, s). 1-387 1 H^NmRvGDClg) u 6.30 (1H, septet, J =6.8Hz), 7.01 (1H, d, J =8.8Hz )T 7.49-7.61 (4H, m), 7.68 (1H, dd, J = 1.0, 7.8 Hz), 7.88-7.91 (2H, m)t 7.96-8.01 (2Ht m), 8.26 (1Ht t, J = 1.9Hz) , 8.33 (1H, s), 8.81 (1H, d, J = 8.8 Hz). 1-389 'H-NMRCCDGls) ά 4.13 (2Η, dt, J=6.4, 14.6Hz), 7.41-7.57 (4H, m), 7.62 (1 H, d, J = 7.8 Hz), 7.99-8.01 (2H, m), 8.09 (2H, d, J = 7.3 Hz), , 8.Z2 (1Ht t J = 2.0 Hz), 9.79(1H? s). 1-390 SH-NMR (CDGi3) δ 7.50-7.6K4H, m), 7,7δ(1Η, d, J = 7.8Hz), l.miH, d, J = 7.8HzX 7 , 93(1 H, s), 7.95(1 Ht s), 8.07(1 H, s), 8.10(1H, s), 8.33(^, s). 1-391 lH~NMR (GDCI3) δ 7.44( 1H, dd, J = 4.9, 7.8Hz), ?.57(1H, t J = 7.8Hz), 7.79(1 H, d, J = 7.8Hz), 7.87-7.BK2H, m), 8.13 (1H , sX 8.23(1H, dd, J = 2.0, 7.8Hz), 8.3K1H, s), 8.42(1H, s)T 8.55(1 H, dd, J = 2.0, 4.9Hz). 1-392 'H- NMR (CDCi3) d 7.22 (1Hf dd, J = 7.8, 12.2 Hz), 7.35 (1H, t,. J = 7.8 Hz), 7.53-7.60 (2H, m), 7.77 (1H, d, J = 7.8 Hz) ), 7.90-7.92(2H, m), 8.13(1H, s)$ 8.19(1H?dt, J = 1-4, 7.8Hz), 8.34( 1H, s), 8.64(1H, d? J = 16.1 Hz). 1-393 W-NiVlR(DMSO-4) d ?·31 -7.38(2H m), 7·50-7.62(2Η,m), 7.66-7.72(4H, m) , 7.92-7.96(3Η, m), 8.Z7(1H, s), 10,61(1H, s), 10.63(1 H, s). 1-394 'H-NMRCDMSO-dg) δ 7.32-7.38 (2HT m)5 7.52-7.60C2H, m), 7.65-7.?3(2H m), 7.94(1H, d, J = 8.3Hz), 8.11(2H, d, J = 8.8Hz), 8.20- 8.23(2H(m), 8.29(1H, s), 10.67(1H, s), 11.0K1H s). 1-395 lH-NMR(CDOI3) d7.45-7.62(6H, m)T 7.69(1H, D5 J=7.8Hz), 7.B3 (2H, d, J=7.3Hz), 8.01 (2H d, J=7.3H2), 8.14(1 H, d, J=7.8Hz), 8.28 (1H, t , J=1.9Hz), 9.95(1H, s), 9.99(1H, s). 1-396 lH-NMR (CDCI3) δ 7.44-7.6K5H, m), 7.73(1H, d, J = E.3Hz ), 7.93(2H, d, J = 8.3Hz), 8.01 (2Hf d, J = 6.8Hz), 8.07-8.13(2Ht m), 8.29(1 H, si 9.97(1 H, s), 10.10(1 H, s). 1-397 'H-NMRCCDCls) d2.41(3H, s), ?.51~7.58(6H, m), 7.67(1H, d, J=6-.3HzX 7.86-7,9l (4H, m), 7.99 (1H si 8.23(1H, d, J=8.3Hz), 8.30(1 H, t J=2.0HzX 117 200836629 4 5(8)
化雜編號 物性値 T 1-398 { 1 H-NMR (CDCi3) δ 3.32 (3Η, s), 3.46 (3H, s), 6.65 (2H, d5 ϋ = ^.OHz), 6.94 (1H, d, J =2.8Hz), 7.07-7.12 (5H, m), 7.25 (2H, d, J =8·4Ηζ), 7_94 (2H, d. J 二8.8Hz), 9,50 (1H, s. OH). 1 1-399 H-NMR(CDC!3) (52.4K3H, s), 7.21(1H, dd, J=1.0, 8.3Hz), 7.35(1 H, t, J=7.3Hz), 7.52-7.59(4H, m), 7.69(1 H, ds J=8.3Hz), 7.86(1H, d, J=8.3Hz), 7.91(1H, s), 8.19(1H, dt, 8.3Hz), 3.23(1H, d, J=8.3Hz), 8.33(1H, t, J=2.0Hz), 8.63(1Ht d, J=15.6Hz). * 1-400 H-NMR(CDC!3) i 2,36 (3H, s), 6.63 (1H, septet, J =6.3Hz), 6.91 (1H, s)t 7.45-7.57 (4H, m), 7.74 (1H, d, J =7.8Hz), 8.03 (2H d, J =8.8Hz), 8.11 (1H, d, J =8.3Hz), 8.17 (1Ht s), 8.39 (1H, t J =1.9Hz), 9.75 (1H, brs), 10.2 (1H, brs). 1-401 'H-NMR(DMS〇-d6) (52.28 (3H, s), 7.12-7.19 (2H, m), 7.33-7.40 (2H, m), 7.52-7.63 (2H, m), 7.67-7.75 (2H, m), 7:94 (1HT d, J =6.8Hz), 8.17 (1H, s), 8.33 (1H, s), 10.1 (1H( brs), 10.6 (1H, s). 1-402 lH-NMR(GDGi3) 56.31 (1H, septet J =5.9Ης), 7.03 (1H, d, J =8.8Hz), 7.20-7.25 (2H, m), 7.34-7.37 (1H, m), 7.54-7.57 (2H, mX 7.68 (1H, dt J =7.8Hz), 8.18-8.23 (1H, m), 8.29-8.30 (2H, m), 8,60 (1/2H, brs), 8.64 (1/2H, brs), 8.83 (1H, d, J =B.8Hz). 1-403 'H-NMRCCDCb) §6.58 (1H, septet, J =6.3Hz), 6.95 (1H, d, J =8.8Hz), 7.45-7.58 (4Ht m), 7.70 (1H, d, J =7.8Hz), 8.00-8.02 (2H m), 8.12 (1H, d, J =7.8Hz), 8.24-8.28 (2H, m), 8.56 (1H5 d, J =2.5Ης), δ.72 (1H, brs), 9.86 (1H, s). 1-404 'H-NMRCCDCy ^6.60 (1H, septet, J =6.3Hz)} 6.96 (1H, d, J =9.2Hz), 7.19-7.23 (1H, m), 7.29-7.33 (1H, m), 7.46-7.54 (2H m)t 7.71 (1H, d, J =7.8H2), 7.87-7.91 (tH, m), 8.06 (1H, d, J =9.2Hz), 8.24-8.28 (2H, m), 8.60 (1H, d, J =2.5Hz), 9.72 (1H, d, J =5.3Hz)t 10.1 (1H, s). 1-405 lH-NMR(DMS〇-d6) d 7.52-7.65(4H, m), 7.74(1 H, d, J = 7.8Hz), 7.85(1 H, d, J = 1.5Hz), 7.98-8.01 (2H, m), 8.06(1 H, dd, J = 1.5, δ.3Ηζ), 8.13(1H, d, ϋ = 1.5Hz), 8.35(1Hf t, J = 1.5Hz), 10.34 (1H, s), 10.47(1H, s). 1-406 'H-NMRiDMSQ-dg) δ 7.32-7.39(2H, m), 7.52-7.63(2H, mX ?.67-7.74(2H, m), 7.84(1 H, s), 7.96(1 H, d, J = ?.8Hz), 8.13(1 H,. d, J = 2.0Hz), 8.30(1H, s), 10.36(1H, s), 10.64(1H, s). 1-407 'H-NMRiDMSO-dg) δ 7.58(1H, t J = 7.8Hz), 7.78(1H, d, J = 7.8Hz), 7.85(1H, d, J = 1.5Hz), 8.05-8.08(1H, m), 8.13 (1H, d, J = 1.5Hz), 8.Z1-8.24(2H} m), 8.34(1H, dt J = 1.5Hz), 8.37-8.40(2H? m), 10.37(1 H, s), 10.78(1 H, s). 118 200836629 表 5ί9)杂性性性値T 1-398 { 1 H-NMR (CDCi3) δ 3.32 (3Η, s), 3.46 (3H, s), 6.65 (2H, d5 ϋ = ^.OHz), 6.94 (1H, d, J = 2.8 Hz), 7.07-7.12 (5H, m), 7.25 (2H, d, J =8·4Ηζ), 7_94 (2H, d. J 8.8 Hz), 9,50 (1H, s. OH) 1 1-399 H-NMR (CDC! 3) (52.4K3H, s), 7.21 (1H, dd, J = 1.0, 8.3 Hz), 7.35 (1 H, t, J = 7.3 Hz), 7.52-7.59 (4H, m), 7.69(1 H, ds J=8.3Hz), 7.86(1H, d, J=8.3Hz), 7.91(1H, s), 8.19(1H, dt, 8.3Hz), 3.23(1H , d, J=8.3Hz), 8.33(1H, t, J=2.0Hz), 8.63(1Ht d, J=15.6Hz). * 1-400 H-NMR(CDC!3) i 2,36 (3H , s), 6.63 (1H, septet, J = 6.3Hz), 6.91 (1H, s)t 7.45-7.57 (4H, m), 7.74 (1H, d, J = 7.8Hz), 8.03 (2H d, J =8.8Hz), 8.11 (1H, d, J = 8.3Hz), 8.17 (1Ht s), 8.39 (1H, t J =1.9Hz), 9.75 (1H, brs), 10.2 (1H, brs). 1- 401 'H-NMR (DMS〇-d6) (52.28 (3H, s), 7.12-7.19 (2H, m), 7.33-7.40 (2H, m), 7.52-7.63 (2H, m), 7.67-7.75 ( 2H, m), 7:94 (1HT d, J = 6.8Hz), 8.17 (1H, s), 8.33 (1H, s), 10.1 (1H( brs), 10.6 (1H, s). 1-402 lH -NMR(GDGi3) 56.31 (1H, septet J = 5.9 Ης), 7.03 (1H, d, J = 8.8 Hz), 7.20-7.25 (2H, m), 7.34-7.37 (1H, m), 7.54-7.57 (2H, mX 7.68 (1H, dt J = 7.8Hz), 8.18-8.23 (1H, m), 8.29-8.30 (2H, m) , 8,60 (1/2H, brs), 8.64 (1/2H, brs), 8.83 (1H, d, J = B.8Hz). 1-403 'H-NMRCCDCb) §6.58 (1H, septet, J =6.3Hz), 6.95 (1H, d, J = 8.8Hz), 7.45-7.58 (4Ht m), 7.70 (1H, d, J = 7.8Hz), 8.00-8.02 (2H m), 8.12 (1H, d , J = 7.8 Hz), 8.24-8.28 (2H, m), 8.56 (1H5 d, J = 2.5Ης), δ.72 (1H, brs), 9.86 (1H, s). 1-404 'H-NMRCCDCy ^6.60 (1H, septet, J = 6.3Hz)} 6.96 (1H, d, J = 9.2Hz), 7.19-7.23 (1H, m), 7.29-7.33 (1H, m), 7.46-7.54 (2H m) t 7.71 (1H, d, J = 7.8H2), 7.87-7.91 (tH, m), 8.06 (1H, d, J = 9.2Hz), 8.24-8.28 (2H, m), 8.60 (1H, d, J =2.5 Hz), 9.72 (1H, d, J = 5.3 Hz) t 10.1 (1H, s). 1-405 lH-NMR(DMS〇-d6) d 7.52-7.65(4H, m), 7.74(1 H , d, J = 7.8Hz), 7.85(1 H, d, J = 1.5Hz), 7.98-8.01 (2H, m), 8.06(1 H, dd, J = 1.5, δ.3Ηζ), 8.13(1H , d, ϋ = 1.5Hz), 8.35(1Hf t, J = 1.5Hz), 10.34 (1H, s), 10.47(1H, s). 1-406 'H-NMRiDMSQ-dg) δ 7.32-7.39(2H , m), 7.52-7.63 (2H, mX ?.67-7.74(2H, m), 7.84(1 H, s), 7.96(1 H, d, J = ?.8Hz), 8.13(1 H,. d, J = 2.0Hz), 8.30(1H, s), 10.36(1H, s), 10.64(1H, s). 1 -407 'H-NMRiDMSO-dg) δ 7.58 (1H, t J = 7.8 Hz), 7.78 (1H, d, J = 7.8 Hz), 7.85 (1H, d, J = 1.5 Hz), 8.05-8.08 (1H , m), 8.13 (1H, d, J = 1.5Hz), 8.Z1-8.24(2H} m), 8.34(1H, dt J = 1.5Hz), 8.37-8.40(2H? m), 10.37(1 H, s), 10.78(1 H, s). 118 200836629 Table 5 ί9)
化合物編號. 物_ ‘ 1 1-408 Η—NMR(DMSO—d6) δ 7.50—7.69(7H,s),7.97— 3.04(3H, m), 8.34(1H, t, ϋ = ZOHz), 10.27(1H, s), 10.46(1H, s). 1-409 H-NMR (CDCl3, PPm) δ S.88-7,95 (11H, m). 1-411 H-NMR(CDCI3) ¢5 7.15-7.20(1H, m), 7.26-7.32(^^), 7.45-7.56(2H,m), 7.69(11^ d, d = 7.8hk), 7.89(1 H,d,J = 2·0Ηζ),7·92 ;1H, d, J = 2.0Hz), 7.99(1 H, dd, J = 2.0,7.8Hz), 8.10-8.15(1 H{ m), 8.1B(1H, s), 8.22(1 H, s), 8.64(1 H, d, ϋ = 15.1 Hz). 1-412 H-NMR(DMS〇-d6) δ 7.59(1H, t, J = 7.8Hz), 7.B2(1H, d, J = 7.8Hz), 8.07-8.10(2H, m), 8.23(2H, d5 J = 8.8Hz), 8.34-8.40 (4H, m), 10.69(1 K s), 10.78(1 H, s). 1-413 'H-NMRCCDCIs) δ 7.4〇-7.45(3H, m), 7.50-7.54(1 H, m), 7.64(1H, d, J = 7.8Hz), 7.75(1 H, d, J = 1.5Hz), 7.81-7.85(3H, m), 8.07(1 H, d, J = 7.8Hz), 8.19(1H, s), 8.Z5(1H, s), 8.54(1H, s). 1-414 'H-NMRCDMSO-ds) δ 7.31-7.3B(2H, m), 7.51-7.61 (2H, m), 7.66-7,72(2H, m), 7.94-7.97(2H, m), 8.28(1 H, d, J = 2.4Hz), 8,31 (1H d, J = 2.4Hz), 10.42(1 H, s), 10.63C1H, s). 1-415 /H-NMRfDMSO—cQ δ 7.51-7·泛(4H, m), 7·72(1Η, d, J = 7·8Ηζ), 7.96-8.00(3H5 m), 8.05(1 H( dd, J = 1.5,7.8Hz), 8.32(1 H, d, ϋ = 2.0Hz), 8.33(1H, d, J = 2.0Hz), 10.40(1H, s). 10.46(1H, s). 1-416 'H-NMRCDMSO-^) δ 7.33-7.40(2H, m), 7.54-7.63(2H, m), 7.67-7.72(1 H, m), 7.79(1H, d, J = ?.8Hz), 7.98(1H, d, J = 7.8Hz), 8.13 (1H, d, J = 1.5Hz)? 8.20(1K d, ϋ = 1.5Hz), 8.35(1H, s), 10.62 (1H, s), 10.67(IH, s). 1-417 ^-NMRCDMSO-dg) d 7.51-7.62(4H, m), 7.71(1H, d, J = 7.8Hz), 7.97-8.06(4H; m), 8.3〇-8.34(2H, m), 10.35(1H, s\ 10.46(tH s). 1-418 'H-NMR (CDC!3t ppm) (5 6.86-6.98 (3H, m), 7.18 (2H, t J=7.8 Hz), 7.33-7.45 (2H, m), 7.58 (1H, t, J=7.8 Hz), 7.B5-8.11 (3H, m). 1-419 lH NMR( DMSO-de )(5 7.52-7.85(7.99-8.06(3H,m),B.15-8.19(1 H,m),8.34(1 H,s),10.4(1 Hrs).10.5(1 KsX 1-420 l|H-NMR(DMSCHd5, ppm) δ7·518·05(11Η,Γπ),8·34(1Η,υ=1·5), 10.2(1H,s),10.5Cias). 1-421 ^-NMRiGDGls) δ1Λ4 (3H, s), 7.16-7.21 (1H, m), 7.44-7.57 (5H, m), 7.66-7.72 (2H, m), 7.83 (1HS d, J =B.3Hz), 7.92-7.95 (2H, m), 8.25 (1H d, J =8.8Hz), 8.31. (1H, s). 1-422 'H-NMRCDMSO-de) <5 0.75C3H, t J = 7.3Hz), 1.19(3H, d, ϋ = 6.8Hz)?l.51-l.59(ZH, m), 3.02-3.11(1H? m)( 7.5〇-7.63(7K m), 7.73 (1H, d, J = 7.8Hz), 7.99-8.07(3H, m), 8.36(1H s), 10.17(1H, s), 10.48(1 H, s). 1-423 ^H-NMRC CDC!3, ppm) a7.48-7.69(7HTm), 7.88-8.00(4H?m), 8.23(1 H.tJ=2.0HzX 8.61(1H,br.s), 8.76(1 H,drJ=8.8Hz). 119 200836629 表5.⑽Compound No.. _ ' 1 1-408 Η-NMR (DMSO-d6) δ 7.50—7.69 (7H, s), 7.97—3.04(3H, m), 8.34(1H, t, ϋ = ZOHz), 10.27( 1H, s), 10.46 (1H, s). 1-409 H-NMR (CDCl3, PPm) δ S.88-7,95 (11H, m). 1-411 H-NMR (CDCI3) ¢5 7.15- 7.20(1H, m), 7.26-7.32(^^), 7.45-7.56(2H,m), 7.69(11^d, d = 7.8hk), 7.89(1 H,d,J = 2·0Ηζ), 7·92 ;1H, d, J = 2.0Hz), 7.99(1 H, dd, J = 2.0, 7.8Hz), 8.10-8.15(1 H{ m), 8.1B(1H, s), 8.22(1 H, s), 8.64 (1 H, d, ϋ = 15.1 Hz). 1-412 H-NMR (DMS 〇-d6) δ 7.59 (1H, t, J = 7.8 Hz), 7.B2 (1H, d , J = 7.8Hz), 8.07-8.10(2H, m), 8.23(2H, d5 J = 8.8Hz), 8.34-8.40 (4H, m), 10.69(1 K s), 10.78(1 H, s) 1-413 'H-NMRCCDCIs) δ 7.4〇-7.45(3H, m), 7.50-7.54(1 H, m), 7.64(1H, d, J = 7.8Hz), 7.75(1 H, d, J = 1.5Hz), 7.81-7.85(3H, m), 8.07(1 H, d, J = 7.8Hz), 8.19(1H, s), 8.Z5(1H, s), 8.54(1H, s). 1-414 'H-NMRC DMSO-ds) δ 7.31-7.3B (2H, m), 7.51-7.61 (2H, m), 7.66-7,72 (2H, m), 7.94-7.97 (2H, m), 8.28(1 H, d, J = 2.4Hz), 8,31 (1H d, J = 2.4Hz), 10.42(1 H, s), 10.63C1H, s). 1-415 /H-NMRfDMSO-cQ δ 7.51-7·Pan (4H, m), 7·72 (1Η, d, J = 7.8 Ηζ), 7.96-8.00 (3H5 m), 8.05 (1 H( dd , J = 1.5, 7.8 Hz), 8.32 (1 H, d, ϋ = 2.0 Hz), 8.33 (1H, d, J = 2.0 Hz), 10.40 (1H, s). 10.46(1H, s). 1- 416 'H-NMRC DMSO-^) δ 7.33-7.40 (2H, m), 7.54-7.63 (2H, m), 7.67-7.72 (1H, m), 7.79 (1H, d, J = ?.8Hz), 7.98(1H, d, J = 7.8Hz), 8.13 (1H, d, J = 1.5Hz)? 8.20(1K d, ϋ = 1.5Hz), 8.35(1H, s), 10.62 (1H, s), 10.67 (IH, s). 1-417 ^-NMRC DMSO-dg) d 7.51-7.62 (4H, m), 7.71 (1H, d, J = 7.8 Hz), 7.97-8.06 (4H; m), 8.3〇-8.34 (2H, m), 10.35 (1H, s\ 10.46(tH s). 1-418 'H-NMR (CDC! 3t ppm) (5 6.86-6.98 (3H, m), 7.18 (2H, t J=7.8 Hz), 7.33-7.45 (2H, m), 7.58 (1H, t, J=7.8 Hz), 7.B5-8.11 (3H, m). 1-419 lH NMR (DMSO-de ) (5 7.52-7.85 (7.99-8.06(3H,m), B.15-8.19(1 H,m),8.34(1 H,s), 10.4(1 Hrs).10.5(1 KsX 1-420 l|H-NMR(DMSCHd5 , ppm) δ7·518·05(11Η,Γπ),8·34(1Η,υ=1·5), 10.2(1H,s),10.5Cias). 1-421^-NMRiGDGls) δ1Λ4 (3H, s ), 7.16-7.21 (1H, m), 7.44-7.57 (5H, m), 7.66-7.72 (2H, m), 7.83 (1HS d, J =B.3Hz), 7.92-7.95 (2H, m), 8.25 (1H d, J = 8.8Hz), 8.31. (1H, s). 1-422 'H-NMRCDMSO-de) <5 0.75C3H, t J = 7.3 Hz), 1.19 (3H, d, ϋ = 6.8 Hz)? l.51-l.59 (ZH, m), 3.02-3.11 (1H? m) (7.5〇-7.63 (7K m), 7.73 (1H, d, J = 7.8Hz), 7.99-8.07(3H, m), 8.36(1H s), 10.17(1H, s), 10.48(1 H, s). 1-423 ^H-NMRC CDC !3, ppm) a7.48-7.69(7HTm), 7.88-8.00(4H?m), 8.23(1 H.tJ=2.0HzX 8.61(1H,br.s), 8.76(1 H,drJ=8.8Hz ). 119 200836629 Table 5. (10)
—化合ΐ編號—- wr±M 1 1-424 H-NMR(DMS〇-d6) ¢5 7.33-7.40(2H, m), 7.52-7.63(2H, m), 7.66-L73(4H,m), 7·95(1Η,d,J 二 7.8Hz),8.05(2H, d,J = 8.8Hz),8.30 1H, s), 10.67(2H, s). 1-425 · H-NMR(CDCt3) (5 3.21(3K s)5 3.41(3H, s), 7.46-7.?5(6H, m), 7.86-7.93(4H, m), 8.D0(1H, s), 8ΌΚ1Η, s), 8.40(1H, s). 1-426 H-NMR(CDCI3) (5 3.2K3H, s)5 3.41(3H, s), 7.51-7.57(2H, m),-7.64(1 H, d, J = 8.8Hz)5 7.89(2H, d, J = 7.8Hz), 7.93(1 H, s), 8.02 ;2H, d, J = 7.8Hz), 8.08( 1K d, J = 8.3Hz), 8.33-8.40(3H, m). 1-427 H-NMR(DMS〇-d6) δ 7.53-7.63(4H, m), 7.79(1H5 d, J = 7.8Hz), 7.98-8ΌΚ2Η, m), 8.06-8.09(1H m), 8.23(2HS s), 8.39(1H, s), 10.50(1 a s)? 10.62(1 H, s). 1-428 lH-NlVlR(DlVlS〇-d6) δ 7.33-7.40(2H, m), 7.54~7.63(2H, m), 7.68-7.72(1 H, m), 7.79(1 H, d, J = 7.8Hz), 7.98(1^ d, J = 8.3Hz), 8.23(2H, s), 8.35(1 H, s), 10.64(1 H, s), 10.67(1 H, s). 1-429 ^-NM^DMSO-dg) d 7.25-7;30(2H, m)? 7.56-7.65(2H, m), 7.81(1 H, d, J = 7.8Hz), 7.94(1 H, d, J = 8.3Hz), 8.23(2H, s), 8.31 (1H, s), 10.67(1 H( s)5 11.06(1 H, s). 1-430 lH—NMR(CDC!3) (5 4.4Ί (2H, t5 d =11.7Hz),7·02 (2H, s),7.50-7.64 (5H, m), 7.73-7.74 (1H, m), 7.89-7.90 (2H, m), 7.95-7.97 (1H, m), 8.04 (1H, s), 8.26 (1H, s). 1-431 ]H-NMR(GDGI3) (54.43 (2H, t, J =1Z.0Hz), 7.05 (2H, s), 7.20-8.21 (8H, m), 8.30 (1H, s), 8.61-8.65 (1H, m). 1-432 ^-NMRCGDCls) ¢2.33 (3H, s)f 4.38 (2H, q, ϋ =8.3Hz), δ.ΒΖ (1H, dd,J 二2.9, 8.8Hz),7.44-7.57 (7H, m), 7.70 (1H, cU 二7.8Hz), 7.99 (1H, dd, J =7.8,1.5Hz), 8.10 (1H, d, J =7.8H2), 8.34 (1H, s), 8.73 (1H, brs), 9.86 (1H, brs). 1-433 lH-N!VIR(CDCI3) 54.43 (2H,t,J 二 11·7Ηζ), 7·04 (2H, s), 7.40—7.44 (1H m), 7.52-7.56 (1H, m)t 7.66 (1H, brs), 7.76-7.78 (1H, m), 7.91-7.93 (1H, m), 8.19-8.24 (2H, m), 8.45 (1H, s), δ.52-8.54 (1H, m). 1-434 'H-NMRCCDCy 52.34(6H, s), 7.47-?.57(〇H m), 7.68(1Hf s\ 7.74 (1H, d, J=7.8Hz), ?.98-B.00(2H, m), 8.12(1H, d, J=7.8Hz), 8.33 (1H, s), 8.64(1H, s), 9,63(1H, s). 1-435 'H-NMRCCDCis) ά 2.35(6H, s), 3.51 (3H, s), 7.32(2H, sX 7.50-7.62(4H, m), 7.66(1 H, s), 7.72(1 H, d, J = 7.8Hz), 7.86-7.90(3H, m), 8.04(1 H, s), 8.31 (1H, d, J = 2.0Hz). 1-436 ^-NMRiCDCls) δ 2.37(6H, s), 3.52(3H, s), 7.23(1H, dd, J = 7.8, 12.2Hz), 7.33(2H, s), 7.35(1 H, t, J = 7.8Hz), 7.52-7.60(2H, m), 7.63(1 H, s), 7.74(1 H, d, J = 7.8Hz), 7.87(1 H, d, J = 7.8Hz), 8.19 (1H dt J = 1.4, 7.8Hz)s 8.34(1H, s), 8.64(1H, d, J = 16.6Hz). 1-437 ^-NMRCDMSO^-dg) d 7.53-7.63(^^),7.75-7.78(1 HTm),7.83(2HTs), 7.99-8.08(3H,m)瓜 37(1 Ks),10.4(1 Kb「·), 10.5(1 H,brJ. 1-438 !H-NMR( GDCi3) ¢52.38(3^9), 7.09-7.12(2Hfm), 7.48-7.57(4H?m), 7.70(1H,cW=8.3Hz)5 7.76(1H,<W二8.3Hz),7.99-8.01(2H,m),8.10(1H,d, |ϋ=8.3ΗΣ), 8.35(1HdJ=2.0Hz), 8.67(1 Hrs), 9.74(1 Ks). 120 200836629表 5(11)—合ΐΐ号— wr±M 1 1-424 H-NMR(DMS〇-d6) ¢5 7.33-7.40(2H, m), 7.52-7.63(2H, m), 7.66-L73(4H,m) , 7·95 (1Η, d, J 2 7.8 Hz), 8.05 (2H, d, J = 8.8 Hz), 8.30 1H, s), 10.67 (2H, s). 1-425 · H-NMR (CDCt3) (5 3.21(3K s)5 3.41(3H, s), 7.46-7.?5(6H, m), 7.86-7.93(4H, m), 8.D0(1H, s), 8ΌΚ1Η, s), 8.40(1H, s). 1-426 H-NMR(CDCI3) (5 3.2K3H, s)5 3.41(3H, s), 7.51-7.57(2H, m), -7.64 (1 H, d, J = 8.8 Hz) 5 7.89 (2H, d, J = 7.8 Hz), 7.93 (1 H, s), 8.02; 2H, d, J = 7.8 Hz), 8.08 (1K d, J = 8.3 Hz), 8.33-8.40 (3H, m). 1-427 H-NMR (DMS〇-d6) δ 7.53-7.63 (4H, m), 7.79 (1H5 d, J = 7.8 Hz), 7.98-8ΌΚ2Η, m), 8.06-8.09 ( 1H m), 8.23(2HS s), 8.39(1H, s), 10.50(1 as)? 10.62(1 H, s). 1-428 lH-NlVlR(DlVlS〇-d6) δ 7.33-7.40(2H, m), 7.54~7.63(2H, m), 7.68-7.72(1 H, m), 7.79(1 H, d, J = 7.8Hz), 7.98(1^d, J = 8.3Hz), 8.23(2H , s), 8.35(1 H, s), 10.64(1 H, s), 10.67(1 H, s). 1-429 ^-NM^DMSO-dg) d 7.25-7;30(2H, m) 7.56-7.65(2H, m), 7.81(1 H, d, J = 7.8Hz), 7.94(1 H, d, J = 8.3Hz), 8.23(2H, s), 8 .31 (1H, s), 10.67 (1 H( s)5 11.06(1 H, s). 1-430 lH-NMR (CDC! 3) (5 4.4 Ί (2H, t5 d =11.7Hz), 7 ·02 (2H, s), 7.50-7.64 (5H, m), 7.73-7.74 (1H, m), 7.89-7.90 (2H, m), 7.95-7.97 (1H, m), 8.04 (1H, s) , 8.26 (1H, s). 1-431 ]H-NMR(GDGI3) (54.43 (2H, t, J =1Z.0Hz), 7.05 (2H, s), 7.20-8.21 (8H, m), 8.30 ( 1H, s), 8.61-8.65 (1H, m). 1-432 ^-NMRCGDCls) ¢ 2.33 (3H, s)f 4.38 (2H, q, ϋ =8.3Hz), δ.ΒΖ (1H, dd, J Two 2.9, 8.8 Hz), 7.44 - 7.57 (7H, m), 7.70 (1H, cU two 7.8 Hz), 7.99 (1H, dd, J = 7.8, 1.5 Hz), 8.10 (1H, d, J = 7.8H2 ), 8.34 (1H, s), 8.73 (1H, brs), 9.86 (1H, brs). 1-433 lH-N!VIR(CDCI3) 54.43 (2H,t,J 2:11), 7·04 (2H, s), 7.40—7.44 (1H m), 7.52-7.56 (1H, m)t 7.66 (1H, brs), 7.76-7.78 (1H, m), 7.91-7.93 (1H, m), 8.19- 8.24 (2H, m), 8.45 (1H, s), δ.52-8.54 (1H, m). 1-434 'H-NMRCCDCy 52.34(6H, s), 7.47-?.57(〇H m), 7.68(1Hf s\ 7.74 (1H, d, J=7.8Hz), ?.98-B.00(2H, m), 8.12(1H, d, J=7.8Hz), 8.33 (1H, s), 8.64 (1H, s), 9,63(1H, s). 1-435 'H-NMRCCDCis) ά 2.35(6H, s), 3.51 (3H , s), 7.32 (2H, sX 7.50-7.62(4H, m), 7.66(1 H, s), 7.72(1 H, d, J = 7.8Hz), 7.86-7.90(3H, m), 8.04( 1 H, s), 8.31 (1H, d, J = 2.0 Hz). 1-436 ^-NMRiCDCls) δ 2.37 (6H, s), 3.52 (3H, s), 7.23 (1H, dd, J = 7.8, 12.2Hz), 7.33(2H, s), 7.35(1 H, t, J = 7.8Hz), 7.52-7.60(2H, m), 7.63(1 H, s), 7.74(1 H, d, J = 7.8 Hz), 7.87 (1 H, d, J = 7.8 Hz), 8.19 (1H dt J = 1.4, 7.8 Hz) s 8.34 (1H, s), 8.64 (1H, d, J = 16.6Hz). 1- 437 ^-NMRCDMSO^-dg) d 7.53-7.63(^^), 7.75-7.78(1 HTm), 7.83(2HTs), 7.99-8.08(3H,m) melon 37 (1 Ks), 10.4 (1 Kb" ·), 10.5(1 H,brJ. 1-438 !H-NMR( GDCi3) ¢52.38(3^9), 7.09-7.12(2Hfm), 7.48-7.57(4H?m), 7.70(1H,cW= 8.3 Hz) 5 7.76 (1H, < W = 8.3 Hz), 7.99 - 8.01 (2H, m), 8.10 (1H, d, | ϋ = 8.3 ΗΣ), 8.35 (1HdJ = 2.0 Hz), 8.67 (1 Hrs ), 9.74 (1 Ks). 120 200836629 Table 5 (11)
一化合物編號 物性値 L 1-439- { H-NMR (GDG!3) δ 6.49(1 H, d, J = 9,3Hz), 7.5.1-7.62(6H, m)f L00(1Ht d, ϋ = 7.3Hz), 8.12(1K d, J = 7.3Hz), 8.45(1Hf d, J = 5.3Hz), 8.B4(1H, s), 9.24(1H, s), 10.49(1K s). 1L55(1H. s). 1-440 MS(APCI)=352(M+1) 1-441 H-NiVIRCCDCIs) δΖ.44 (3H, s), 7.31-7.59 (5H, m), 7.73 (1H, d, J =7.8Hz), 7.97 (2H, dd, J =1.5, 7.8Hz), 8.06 (1H, d? J =7.8Hz), 8.36 (1HS t J =1.9Hz), 8.94 (1H, s), 9.03 (1H, s), 9.32 (1H, s). 1-442 H-NMR(GDCi3) ¢7.46-7.68 (4H, m), 7.77 (1H, d, ϋ =7.9Hz), 8Ό0-B.02 (2HS m), 8.09 (1H, d, ϋ =2.0Hz), B.17 (1H, dd, J =8.3,1.5Hz), 8.38 (1H, t, J =1.5Hz), 8.67 (1K d, J =2.0Hz), 10.2 (1H, brs), 10.4 (1H, brs). 1-443 'H-NIVlR(DIVIS〇-d6) d 2.23(3H, d, J = 2.9Hz), 3.81 (3Ht s), 7.53-7.63(4H, m), 7J5(1H, d, J = 7.3Hz), Β.01-8.06(3Η( m), 8.37(1 H, s), 10.29(1 H, s), 10.49(1 H, s). 1-444 ^-NMRCDMSO-ds) d 2.23(3H, d, J = 2.0Hz), 3.81 (3H, s), 7.33-7.40(2H, m), 7.53-7.63(2H, m), 7.67-7.76(2H, m), 7.95(1 Hf d, J = 7.8Hz), 8.33(1 H, s)t 10.30(1 H, s), 10.66(1 H, s). 1-445 lH^MR(GD0!3) §2.36 (3H, s), 7.25 (1H, s)f, 7.47-7.57 (4H, m), 7.77 C1H, d, J =7.8ΗςΧ 7.99 (2H, dd, J =1.5, 8.7Hz), 8.14 (1H, dd, J =1.5, 7.8Hz), 8.38 (1H, t, J =1.5Hz), 9.28 (1H, brs), 9.82 (1H; brs). 1-446 lH-NMR(DMSO~d6) δ 2.29(6H, s), 7.51-7.63(6H, m)t 7.76(1 H, d, J = 7.8Hz), 7.98-8ΌΚ2Η m), 8.05(1H, dd, J = 2.0,7.8Hz), 8.37(1H, t J = 2.0Hz), 10.02(1 H, s), 10.47(1 Hs s). 1-447 lH-NMR(DMS〇-d6) δ Z28(6H, s), 7.33~7.40(2H, m)t 7.53(2H, s), 7.54-7.77(4H, m)f 7.95(1 H, d, J = 8.3Hz), 8.33(1 H, s), 10.03(1 H, s)t 10.64(1H, s). 1-448 ^-NMRCGDCls) δ4.67(2Η, d, J=5.9H2), 7.4〇-7.65(9H, m), 7.97-8.03(4H, m), 8.27(1 H, t J=2.0Hz), 9.73(1 H, s). 1-449 'H-NMRCGDCg 54.88(2H, d, J=5.8Hz), 7.43-7.65(9H m), 7.98-8.00(3H, m)t 8.04(1 H, d, J=8.2Hz), 8.24(1 H, d, J=1.9Hz)f 9.68 (1H, s). 1-450 'H-NMRCCDCIs) δ4.83(2Η, d, J=5.8Hz), 6.58(1 H, brs), 7.40-7.69 (9H, mX 7.86-7.88(ZH, m), 7.92(1H, d, J=8.3Hz), 7.97(1 H, s), 8.05 (1H, tf J=2.0Hz). 1-451 MS(APGI)=376(M+1) 1-452 lH-NMR(GDC!3) δ4.7δ(2Η5 d, ϋ=5.9Ηζ), 6.82(1H, brs), 7.45-7.63 (5H, m), 7.79(2H, s), 7.80(2H, s), 7.87(2H, d, J=7.4Hz), 8.00(1 H, s), 8.21 (1H, t J=2.0Hz). 1-453 'H-NIVlR(DIV!S〇-d6) d 2.19(6H, s), 7.24(2H, s), 7.49-?.63(4H, m), 7.73-7.7δ(1Η, m)t 7.98-B.05(3H, m\ 8.35(1H, t J = 1.5Hz), 9.83 (1H s), 10.46(1 H,s). 121 200836629 --物性値-- T 1-454 : t H-NMR(DMS〇-d6) <52.19(6H, s), 7.37(2H;s), 7.49-7.63(4H, m)( ?.74(1H( d, ϋ =7.8Hz)f 7.98- 8.05C3H, m), 8.35(1 H, t, J =2.0Hz), L82(1H, s), 10.44(1 HT s). • i 1-455 H-NMR(CDCi3) ^2.24 (6H, 4 7.43-7.57 (6H, m)5 7.74 (1H, d, J =7.3Hz), 8.01 (2H, d? J =8.3Ηζ)5 8.12 (1H, d, J =8.3Hz), 8.36 1H brs), 9.32 (1H, brs), 10.1 (1H, brs). 1-456 H-NMR(CDCl3) δ 2.19(6H, s)t 6.97-?.04(2H, m), 7.39-7.49 ;4H, m), 7.55(1 H, brs), 7.69(1 H d, J = 8.3Hz), 7.79(1 Hf dd, J = 8.3, 1.5Hz), 8.04(1 H, brs), 8.24(1 H, t J = 1.5Hz). 1-457 H-NMR(DMS〇-d6) <5 7.50-7.62(5H, m), 7.67-7.69(1 H, m), 7.83 :1H, dd,J = 2.4,8.3Hz), 7-88(1H,d,J 二 2.4Hz), 7.97-δ·04(3Η, m), δ.33(1 H, t, J = 2.0Hz), 10.20(1 H, s), 10.46(1 H, s). • • 1-458 H-NMR(DMS〇-d6) δ ?.51-7.64(5H, m), 7.72(1H, d, J = 7.8Hz), 7.82(1 H, d, J = 6.8HzX 7.94-8.00(3HT m), 8.03-8.06(1 H, m), 8.33 (1H, s), Ί0.33ΟΗ, s), 10.46(1K s). 1-459 lH-NMR(DMS〇-d6) ¢7.45-7.63 (6H, m), 7.91-8.01 (4H, m), 8.16 (1H, d, J =8.3Hz), 8.32 (1H, t J =1.5Hz), 8.65 (1H, brs), 10.0 (1H, brs). 1-460 'H-NIVIR(DMS〇-d6) d2.21 (3H, s), 7.51-7.63 (4H, m), 7.72-7.76 (2H, m), 7.80 (1H, d, J =1.9Ηζλ 7.99 (2H, d, J =8.8Hz), 8.05 (1H, d, J =8.8Hz), 8.36 (1H, brs), 10.0 (1H, brs), 10.5 (1H, brs). 1-461 lH-NMR(CDCi3) ^2.27 (6H, s), 7.08-7.15 (3H, m), 7.48-7.60 (5H m), 7.69 (1H, d, ϋ =7.8Hz), 7.B6-7.89 (2H, m), 7.95-7.97 (1H, m), 8.11 (1H, brs), 8.22 (IK s). 1-462 ^-NMRCCDCis) 53.87 (3H, s), 7.47-7.59 (3H, m), 7.72 (1H, d, J =2.9Hz), 7.78 (tH, d, J =7.8Hz), 7.99-8.03 (2H, m), 8.12 (1H, df J =7.8Hz), 8.46 (1H, s), 10.3 (1H, brs), 10.4 (1H, brs). 1-463 'H-NMmDIVISO—cg d 7.53—7·64(4Η, m), 7.77(1H, d,J = 8.3hk), 7.98-8.01 (2H, m), 8.07(1 H, dd, J = 1.5,8.3Hz), 8.43(1 H, 1; J = 1.5Hz), 10.5K1H s), 10.97(1H, s). 1-464 'H-NMRCDMSO-d^ δ 7.53-7.64(4Ht m), 7.75(1 H, d, J = 8.3Hz), ?.99-8.08(3H, m), 8.41(1H, s), 10.50(1H, s), 10.59(1H, s). 1-465 'H-NMRCDMSO-dg) δ ?.33-7.44(4H, m), 7.51-7.63(2Hf m), 7.67-7.74(2H, m), 7.95(1H, d, J = 7.8Hz), 8.32(1H, s), 10.40(1^ s\ 10.65 (1H, s). 1-466 ^H-!MMR(DMS〇-cl6) δ 7.33-7.40(2H, m), 7.52-7.63(2H, m), 7.68-7.7K2H, m), 7.74(2H, d, J = 8.8Hz), 7.96(1H, d, J = 7.8Hz), 8.02 (2H, d, J = 8.8Hz), 8.30(1H, s), 10.67(2H, s). 1-467 1H-NMR(DMS0-d6) 0' 7.33-7.40C2H, m), 7.53-7.63(2H, m), 7.68-7.72(1 H, m), 7.77(1 H, d,d = 7·8Ηζ), 7·83(1Η, dd, J = 2.0, 8.3HzX 7.89(1H, d, J = 8.3Hz), 7.97(1H, d, J = 7.8Hz), 8.13 (1H, s), 8.36(1H, s), 10.26(1H, s), 10.68(1H s). 1-468 'H-NMR(DMS〇-d6) 5 ?.53-7.63(4H, m)t 7.78(1H d, J = 7.8Hz), 7.98-8.0K2H, m), 8.06-8.07(1H, m), 8.13(1H, d, J = 2.0Hz), 8.20 (1H, d, J = 2.0Hz), 8.39(1H, d, J ^ 2.0Hz), 10.50(1H, s), 10.60(1H, s). 122 200836629表 5(13)A compound numbering property 値L 1-439- {H-NMR (GDG!3) δ 6.49 (1 H, d, J = 9,3 Hz), 7.5.1-7.62 (6H, m)f L00 (1Ht d, ϋ = 7.3 Hz), 8.12 (1K d, J = 7.3 Hz), 8.45 (1Hf d, J = 5.3 Hz), 8.B4 (1H, s), 9.24 (1H, s), 10.49 (1K s). 1L55(1H.s). 1-440 MS(APCI)=352(M+1) 1-441 H-NiVIRCCDCIs) δΖ.44 (3H, s), 7.31-7.59 (5H, m), 7.73 (1H, d, J = 7.8 Hz), 7.97 (2H, dd, J = 1.5, 7.8 Hz), 8.06 (1H, d? J = 7.8 Hz), 8.36 (1HS t J = 1.9 Hz), 8.94 (1H, s) , 9.03 (1H, s), 9.32 (1H, s). 1-442 H-NMR(GDCi3) ¢7.46-7.68 (4H, m), 7.77 (1H, d, ϋ =7.9Hz), 8Ό0-B. 02 (2HS m), 8.09 (1H, d, ϋ =2.0Hz), B.17 (1H, dd, J = 8.3, 1.5Hz), 8.38 (1H, t, J = 1.5Hz), 8.67 (1K d , J = 2.0Hz), 10.2 (1H, brs), 10.4 (1H, brs). 1-443 'H-NIVlR(DIVIS〇-d6) d 2.23(3H, d, J = 2.9Hz), 3.81 (3Ht s), 7.53-7.63(4H, m), 7J5(1H, d, J = 7.3Hz), Β.01-8.06(3Η( m), 8.37(1 H, s), 10.29(1 H, s) , 10.49(1 H, s). 1-444 ^-NMRCDMSO-ds) d 2.23(3H, d, J = 2.0Hz), 3.81 (3H, s), 7.33-7.40(2H, m), 7.53-7.63 (2H, m), 7.67-7.76(2H, m), 7.95(1 Hf d, J = 7.8Hz), 8.33(1 H, s)t 1 0.30(1 H, s), 10.66(1 H, s). 1-445 lH^MR(GD0!3) §2.36 (3H, s), 7.25 (1H, s)f, 7.47-7.57 (4H, m ), 7.77 C1H, d, J = 7.8ΗςΧ 7.99 (2H, dd, J = 1.5, 8.7Hz), 8.14 (1H, dd, J = 1.5, 7.8Hz), 8.38 (1H, t, J = 1.5Hz) , 9.28 (1H, brs), 9.82 (1H; brs). 1-446 lH-NMR (DMSO~d6) δ 2.29 (6H, s), 7.51-7.63 (6H, m)t 7.76 (1 H, d, J = 7.8 Hz), 7.98-8 ΌΚ 2 Η m), 8.05 (1H, dd, J = 2.0, 7.8 Hz), 8.37 (1H, t J = 2.0 Hz), 10.02 (1 H, s), 10.47 (1 Hs s 1-447 lH-NMR (DMS〇-d6) δ Z28(6H, s), 7.33~7.40(2H, m)t 7.53(2H, s), 7.54-7.77(4H, m)f 7.95(1 H, d, J = 8.3 Hz), 8.33(1 H, s), 10.03(1 H, s)t 10.64(1H, s). 1-448 ^-NMRCGDCls) δ4.67(2Η, d, J= 5.9H2), 7.4〇-7.65(9H, m), 7.97-8.03(4H, m), 8.27(1 H, t J=2.0Hz), 9.73(1 H, s). 1-449 'H-NMRCGDCg 54.88(2H, d, J=5.8Hz), 7.43-7.65(9H m), 7.98-8.00(3H, m)t 8.04(1 H, d, J=8.2Hz), 8.24(1 H, d, J =1.9Hz)f 9.68 (1H, s). 1-450 'H-NMRCCDCIs) δ4.83(2Η, d, J=5.8Hz), 6.58(1 H, brs), 7.40-7.69 (9H, mX 7.86 -7.88(ZH, m), 7.92(1H, d, J=8.3Hz), 7.97(1 H, s), 8.05 (1H, tf J=2.0Hz). 1-451 MS(APGI)=376(M+1) 1-452 lH-NMR(GDC!3) δ4.7δ(2Η5 d, ϋ=5.9Ηζ), 6.82(1H, brs), 7.45-7.63 (5H, m) , 7.79(2H, s), 7.80(2H, s), 7.87(2H, d, J=7.4Hz), 8.00(1 H, s), 8.21 (1H, t J=2.0Hz). 1-453 ' H-NIVlR(DIV!S〇-d6) d 2.19(6H, s), 7.24(2H, s), 7.49-?.63(4H, m), 7.73-7.7δ(1Η, m)t 7.98-B .05(3H, m\ 8.35(1H, t J = 1.5Hz), 9.83 (1H s), 10.46(1 H,s). 121 200836629 -- Physical properties -- T 1-454 : t H-NMR ( DMS〇-d6) <52.19(6H, s), 7.37(2H;s), 7.49-7.63(4H, m)( ?.74(1H( d, ϋ =7.8Hz)f 7.98- 8.05C3H, m ), 8.35 (1 H, t, J = 2.0 Hz), L82 (1H, s), 10.44 (1 HT s). • i 1-455 H-NMR (CDCi3) ^ 2.24 (6H, 4 7.43-7.57 ( 6H, m)5 7.74 (1H, d, J = 7.3 Hz), 8.01 (2H, d? J = 8.3 Ηζ) 5 8.12 (1H, d, J = 8.3 Hz), 8.36 1H brs), 9.32 (1H, Brs), 10.1 (1H, brs). 1-456 H-NMR (CDCl3) δ 2.19(6H, s)t 6.97-?.04(2H, m), 7.39-7.49; 4H, m), 7.55(1) H, brs), 7.69 (1 H d, J = 8.3 Hz), 7.79 (1 Hf dd, J = 8.3, 1.5 Hz), 8.04 (1 H, brs), 8.24 (1 H, t J = 1.5 Hz) 1-457 H-NMR (DMS〇-d6) <5 7.50-7.62 (5H, m), 7.67-7.69 (1 H, m), 7.83 :1H, dd,J = 2.4, 8.3 Hz), 7-88 (1H, d, J 2.4 Hz), 7.97-δ·04 (3Η, m), δ.33 (1 H, t, J = 2.0 Hz), 10.20 (1 H, s), 10.46(1 H, s). • • 1-458 H-NMR (DMS〇-d6) δ ?.51-7.64(5H, m), 7.72(1H, d, J = 7.8Hz) , 7.82(1 H, d, J = 6.8HzX 7.94-8.00(3HT m), 8.03-8.06(1 H, m), 8.33 (1H, s), Ί0.33ΟΗ, s), 10.46(1K s). 1-459 lH-NMR (DMS〇-d6) ¢ 7.45-7.63 (6H, m), 7.91-8.01 (4H, m), 8.16 (1H, d, J = 8.3 Hz), 8.32 (1H, t J = 1.5Hz), 8.65 (1H, brs), 10.0 (1H, brs). 1-460 'H-NIVIR(DMS〇-d6) d2.21 (3H, s), 7.51-7.63 (4H, m), 7.72 -7.76 (2H, m), 7.80 (1H, d, J = 1.9Ηζλ 7.99 (2H, d, J = 8.8Hz), 8.05 (1H, d, J = 8.8Hz), 8.36 (1H, brs), 10.0 (1H, brs), 10.5 (1H, brs). 1-461 lH-NMR(CDCi3) ^2.27 (6H, s), 7.08-7.15 (3H, m), 7.48-7.60 (5H m), 7.69 (1H , d, ϋ =7.8Hz), 7.B6-7.89 (2H, m), 7.95-7.97 (1H, m), 8.11 (1H, brs), 8.22 (IK s). 1-462 ^-NMRCCDCis) 53.87 (3H, s), 7.47-7.59 (3H, m), 7.72 (1H, d, J = 2.9Hz), 7.78 (tH, d, J = 7.8Hz), 7.99-8.03 (2H, m), 8.12 ( 1H, df J =7.8Hz), 8.46 (1H, s), 10.3 (1H, brs), 10.4 (1H, brs 1-463 'H-NMmDIVISO-cg d 7.53-7·64(4Η, m), 7.77(1H, d,J = 8.3hk), 7.98-8.01 (2H, m), 8.07(1 H, dd , J = 1.5, 8.3 Hz), 8.43 (1 H, 1; J = 1.5 Hz), 10.5 K1H s), 10.97 (1H, s). 1-464 'H-NMRC DMSO-d^ δ 7.53-7.64 (4Ht m), 7.75(1 H, d, J = 8.3Hz), ?.99-8.08(3H, m), 8.41(1H, s), 10.50(1H, s), 10.59(1H, s). 1- 465 'H-NMRC DMSO-dg) δ ?.33-7.44 (4H, m), 7.51-7.63 (2Hf m), 7.67-7.74 (2H, m), 7.95 (1H, d, J = 7.8 Hz), 8.32 (1H, s), 10.40(1^ s\ 10.65 (1H, s). 1-466 ^H-!MMR(DMS〇-cl6) δ 7.33-7.40(2H, m), 7.52-7.63(2H, m ), 7.68-7.7K2H, m), 7.74 (2H, d, J = 8.8Hz), 7.96 (1H, d, J = 7.8Hz), 8.02 (2H, d, J = 8.8Hz), 8.30(1H, s), 10.67(2H, s). 1-467 1H-NMR(DMS0-d6) 0' 7.33-7.40C2H, m), 7.53-7.63 (2H, m), 7.68-7.72 (1 H, m), 7.77(1 H, d,d = 7·8Ηζ), 7·83(1Η, dd, J = 2.0, 8.3HzX 7.89(1H, d, J = 8.3Hz), 7.97(1H, d, J = 7.8Hz ), 8.13 (1H, s), 8.36(1H, s), 10.26(1H, s), 10.68(1H s). 1-468 'H-NMR(DMS〇-d6) 5 ?.53-7.63(4H , m)t 7.78(1H d, J = 7.8Hz), 7.98-8.0K2H, m), 8.06-8.07(1H, m), 8.13(1H, d, J = 2.0Hz ), 8.20 (1H, d, J = 2.0Hz), 8.39(1H, d, J ^ 2.0Hz), 10.50(1H, s), 10.60(1H, s). 122 200836629Table 5(13)
化働驟——: —___________ 1-469 · H-NMR(DMS〇-d6) δ 7.2?-7.39(2H, m), ?.51~7.63(4Η, m), 7.68-L77(3H, m), 7.81(1H, d, J = 7.8Hz), 7.95-7.98(1H, m), 8.31(1H, s), 10.19OH, s), 10.66(1H, sX 1 Ί-470 H-NMR(DMS〇-d6) δ 7.51-7.62(^, m), 7.71〇H d, J = 7.8Hz), d, J = 2.4HzX 7.97-8,06(3H, m),8_20(1H d, J : 2.4Hz), B.33(1H, t J = 2.0Hz), 10.37(1 H, s), 10.46(1 H, s). 1-471 H-NMR(DMS〇-d6) $ 1.26(6H, d, J = 6.8Hz), 3.08(1 H, septet, J = 6.8Hz), 7.52-7.63(4H, m), 7.69-7.74C2H, m), 7.98-8.01 (3H, m), 8.06 [1H, dd, J = 1.5,7.8Hz), 8.32(1H, t J = 1.5Hz), 10.28(1H, s), 10.47 〔1H,s)· 1-472 lH-NMR(DMS〇-d6) δ 1.26(6Ht d, J = 6.8Hz), 3.08(1 H, septet, J = 6.8Hz), 7.32-7.39(2H, m), 7.51>7.63(2H, m), 7.67-7.73(3H, m), 7.96~7.98(2H, m), 8.27(1H, si 10.30(1H, s), 10.65(1H, s). 1-473 ]H-NMR(DMS〇-d6) δ 7.44-8.06(13H, m), 10.39(1H, s), 10.48 (1K s). 1-474 'H-NMR (DMS〇-d6) <5 2.42(3Ht s), 7.53-7.64(4H, m), 7.75(1H, d, J = 7.8Hz), 7.83(1 H, d, J = 7.8Hz), 8.00(2H, d, J = 6.8Hz), 8.06 (1H d, J = B.3Hz), 8.13(1 H, d, J = B.3Hz), 8.21(1 H, s), 8.40(1 H, s), 10.17(1 H, s), 10.50(1 H, s). 1-475 MS(APGI)=385(M+1) 1—4-76 MS(APCI)=488(M+1) 1-477 'H-NMR (CDCi3) 6 3.35(6H, s), 7.51-7.6K5H, m), 7.77(1H, t, J = 8.8Hz), 8.00(2H, d, J = 7.8Hz), 8.05-8.07(2H, m), 8.40(1 H, s), 10.14(1H. s), 10.48(1H, s). 1-478 'H-NMRCDMSO-de) δ 7.48-7.56(3K m), 7.63-7.67(2^ m), 7.94-7.99(4H, m), 8.22(1 H. s), 9.03(1 H s), 9.46(2H, s). 卜479 lH-NMR (CDCl3) δ 7.53-7.62C5K m), 7.76(1 H, d, J = 7.8Hz), 8.00 (2H, d, ϋ = 7.3Hz), 8.08(1 K d, J = 7.8Hz), 8.42(1 H, s), 8.95(1 H, sX 9.30(1H, s), 10.50C1H, s). 1-480 ]H-NMR( CDCi3, ppm) δ 1.36(9H!s)f2.34(3HTs)t6.92-*6.95(2Hfm), 7.49-8.22(12H,m). 1-481 iHHMMRCDMSOdP δ 2.50(3H,s),7.14(1H,dcW=2.5,8,8H2:), 7.21(1H,d,J=2.4HzX 7.41(1H,d,J=8.8HzX 7.50-7.75(8H,m)f 7.97-8.14(5H,m), 8.34(1H,s), 9.98(1HTs), 10.47(lH.s). 1-482 'H-NMRCDMSO-de) δ 2.28(3H,s), 7.31(1 Hts), 7.50-8.16(14H,mX 8.38(1Hts), 10.09(1KsX 10.48(1H,s). Ί —48^ sH-NMR(DMS〇-cl6) δ 2.15(3H,s), 6.69(1 H,dTJ=2.4HzX 6.78(1 H,d,J=2.4H2X 7.4B-7.63(4Hm), 7.74(1 H,d,J=8.8Hz)? 7.98-8.05(3H,mX 8.32(1 H,tJ=2.4Hz), 9.77(1H,s), 9.82(1Ks), 10.4(1H.s). 123 200836629 表 5(14) 化_編號— —物論—--- 1-484 H-NMR( DMS〇-d6) δ 2.16(3H,s), 6.72(1 H,d,J=2.4Hz), 3.94(1 HrdfJ=2.4Hz), 7.5〇-7.63(4H,m), 7.74(1 H,d,J=8.3Hz), 7.98-B.05(3H,m), 8_32(1H,s), 9,79(1Hs), 9.81(1H,s), 10.4(1H,s)· 1-485 H-NMR(CDCl3) (5 Z.29(3H,s), 2.48(3Ks), 6.94(1 ΗΛϋ=2.9Ηζ), 7.14(tH,d,J=2.9H2), 7.36(2HTd,J=8.3Hz), 7.51-7.61 (5H,m), 7.71-7.77(3H?m), 7.88-7.92(3Hm), 7.99(1 Rbr.s), 8.28(1 Hfs). 1-486 'H-NMR (CDCi3) δ 1.82-1.89 (4H, m), 3.30-3.60 (7H? m), 7.23-7.30 (5H, m), 7.44 (2H, s)T 7.76 (2H, d, J=4.9 Hz), 7.87 (2H, d, J=6.4 Hz), 10.4 (1H, s). 1-4B7 'H-NMR (CDCI3t ppm) δ 1.41 (3H, t, J=7.3 Hz), 3.57 (3H, s), 4.41 (2H q, J=7.3 Hz), 7.20-7.34 (6H, m), 7.40 (2H, t J=7.8 Hz), 7.61 (1H, d, J=2.0 Hz), 7.71 (1H, d, J=7.8 Hz)t 8.27 (2H, s). 1-488 'H-NIVIR (DMS〇-d6) δ 7.51-7.59 (3H, m), 7.62 (2H, s), 7.78 (1H, d, J=7.8 Hz), 7.86 (1H, d, J=7.8 Hz), 7.89-7.91 (2H, m), 8.05 (2H, d, J=7.3 Hz), 8.38 (1H, s), 9.47 (1H, s). 1-489 'H-NMRCCDCb,ppm) δ 2.92 (4H, s), 7.48 (2H, s), 7.48-7.59 (4H, m), 7.76 (1H, d, J=7.8 Hz), 7.85 (1H, s), 7.90 (2H, d, J=7.8 Hz), 7.96 (IK d, J=7.8 Hz), 8.03 (1H s), 8.24 (1H, s). 1-4B0 'H-NMR (CDGI3i ppm) (5 7.49-B.02 (15H, m), 8.10 (1H, d, J=7.3 Hz), 8.22 (1H, s). 1-491 MS(APCI)=374(M+1) .1-492 IVlS(APCI)=374(M+l) 1-493 MS(APCI)=408(M+1) 1-494 MS(APGI)=402(M-H) 1-495 MS(APCI)=404(M+1) 1-496 MS(APGI)=392(M+1) 1-497 'H-NMRCDlVlSO-de) δ 7.52-7.62 (5Ht m), 7.80 (1H, d, J =6.8Hz), 7.97-8.00 (2H, m)} 8.05 (1H, d} J =7-8Hz), 8.32 (1H, d, J =5.9Hz), 8.38 (1H, s), 8.92 (1H, t, J =3.9HzX 10.48-10.54 (2H, m). 1-498 'H-NMR(DMSO~d6) δ 7.51-7.59 (3H, m), 7.80-7.85 (1Hf m), 7.92-7.96 (1Ht m), 8.09 (1H, dd, J =7.3, 2.0Hz), 8.21 (1H, dd, J =7.3, 2.0Hz), 8.40 (1H, brs), 8.54 (2H, d, J ^.OHz), 10.38 (1H, s), 10.86 (1H, s).働 —— -————___________ 1-469 · H-NMR (DMS〇-d6) δ 7.2?-7.39(2H, m), ?.51~7.63(4Η, m), 7.68-L77(3H, m ), 7.81 (1H, d, J = 7.8 Hz), 7.95-7.98 (1H, m), 8.31 (1H, s), 10.19 OH, s), 10.66 (1H, sX 1 Ί-470 H-NMR (DMS) 〇-d6) δ 7.51-7.62(^, m), 7.71〇H d, J = 7.8Hz), d, J = 2.4HzX 7.97-8,06(3H, m), 8_20(1H d, J : 2.4 Hz), B.33(1H, t J = 2.0Hz), 10.37(1 H, s), 10.46(1 H, s). 1-471 H-NMR(DMS〇-d6) $ 1.26(6H, d , J = 6.8Hz), 3.08(1 H, septet, J = 6.8Hz), 7.52-7.63(4H, m), 7.69-7.74C2H, m), 7.98-8.01 (3H, m), 8.06 [1H, Dd, J = 1.5, 7.8 Hz), 8.32 (1H, t J = 1.5 Hz), 10.28 (1H, s), 10.47 [1H, s)· 1-472 lH-NMR (DMS〇-d6) δ 1.26 ( 6Ht d, J = 6.8Hz), 3.08(1 H, septet, J = 6.8Hz), 7.32-7.39(2H, m), 7.51>7.63(2H, m), 7.67-7.73(3H, m), 7.96~7.98(2H, m), 8.27(1H, si 10.30(1H, s), 10.65(1H, s). 1-473 ]H-NMR(DMS〇-d6) δ 7.44-8.06(13H, m) , 10.39(1H, s), 10.48 (1K s). 1-474 'H-NMR (DMS〇-d6) <5 2.42(3Ht s), 7.53-7.64(4H, m), 7.75(1H, d , J = 7.8Hz), 7.83(1 H, d, J = 7.8Hz), 8.00(2H, d, J = 6. 8Hz), 8.06 (1H d, J = B.3Hz), 8.13(1 H, d, J = B.3Hz), 8.21(1 H, s), 8.40(1 H, s), 10.17(1 H, s), 10.50(1 H, s). 1-475 MS(APGI)=385(M+1) 1-4-76 MS(APCI)=488(M+1) 1-477 'H-NMR (CDCi3 6 3.35(6H, s), 7.51-7.6K5H, m), 7.77(1H, t, J = 8.8Hz), 8.00(2H, d, J = 7.8Hz), 8.05-8.07(2H, m), 8.40(1 H, s), 10.14(1H.s), 10.48(1H, s). 1-478 'H-NMRCDMSO-de) δ 7.48-7.56(3K m), 7.63-7.67(2^ m), 7.94-7.99(4H, m), 8.22(1 H. s), 9.03(1 H s), 9.46(2H, s). 479 lH-NMR (CDCl3) δ 7.53-7.62C5K m), 7.76(1 H, d, J = 7.8 Hz), 8.00 (2H, d, ϋ = 7.3 Hz), 8.08 (1 K d, J = 7.8 Hz), 8.42 (1 H, s), 8.95 (1 H, sX 9.30 ( 1H, s), 10.50C1H, s). 1-480 ]H-NMR(CDCi3, ppm) δ 1.36(9H!s)f2.34(3HTs)t6.92-*6.95(2Hfm), 7.49-8.22( 12H,m). 1-481 iHHMMRCDMSOdP δ 2.50(3H,s), 7.14(1H,dcW=2.5,8,8H2:), 7.21(1H,d,J=2.4HzX 7.41(1H,d,J=8.8 HzX 7.50-7.75(8H,m)f 7.97-8.14(5H,m), 8.34(1H,s), 9.98(1HTs), 10.47(lH.s). 1-482 'H-NMRCDMSO-de) δ 2.28 (3H,s), 7.31(1 Hts), 7.50-8.16(14H,mX 8.38(1Hts), 10.09(1KsX 10.48(1H,s). Ί —48^ sH -NMR (DMS 〇-cl6) δ 2.15 (3H, s), 6.69 (1H, dTJ = 2.4 Hz X 6.78 (1 H, d, J = 2.4H2X 7.4B-7.63 (4Hm), 7.74 (1 H, d , J=8.8Hz)? 7.98-8.05(3H,mX 8.32(1 H,tJ=2.4Hz), 9.77(1H,s), 9.82(1Ks), 10.4(1H.s). 123 200836629 Table 5(14 ) _ number - object theory - 1-- 1-484 H-NMR ( DMS 〇 - d6) δ 2.16 (3H, s), 6.72 (1 H, d, J = 2.4 Hz), 3.94 (1 HrdfJ= 2.4 Hz), 7.5〇-7.63(4H,m), 7.74(1 H,d,J=8.3Hz), 7.98-B.05(3H,m), 8_32(1H,s), 9,79(1Hs ), 9.81(1H,s), 10.4(1H,s)· 1-485 H-NMR(CDCl3) (5 Z.29(3H,s), 2.48(3Ks), 6.94(1 ΗΛϋ=2.9Ηζ), 7.14(tH,d,J=2.9H2), 7.36(2HTd,J=8.3Hz), 7.51-7.61 (5H,m), 7.71-7.77(3H?m), 7.88-7.92(3Hm), 7.99(1 Rbr.s), 8.28(1 Hfs). 1-486 'H-NMR (CDCi3) δ 1.82-1.89 (4H, m), 3.30-3.60 (7H? m), 7.23-7.30 (5H, m), 7.44 (2H, s)T 7.76 (2H, d, J=4.9 Hz), 7.87 (2H, d, J=6.4 Hz), 10.4 (1H, s). 1-4B7 'H-NMR (CDCI3t ppm) δ 1.41 (3H, t, J=7.3 Hz), 3.57 (3H, s), 4.41 (2H q, J=7.3 Hz), 7.20-7.34 (6H, m), 7.40 (2H, t J=7.8 Hz), 7.61 (1H, d, J=2.0 Hz), 7.71 (1H, d, J=7.8 Hz)t 8.27 (2H, s). 1-488 'H-NIVIR (DMS〇-d6) δ 7.51-7.59 (3H, m), 7.62 (2H, s), 7.78 (1H, d, J=7.8 Hz), 7.86 (1H, d, J=7.8 Hz), 7.89-7.91 (2H, m), 8.05 (2H, d, J = 7.3 Hz), 8.38 (1H, s), 9.47 (1H, s). 1-489 'H-NMRCCDCb, ppm) δ 2.92 (4H, s), 7.48 (2H, s), 7.48-7.59 (4H, m), 7.76 (1H, d, J=7.8 Hz), 7.85 (1H, s), 7.90 (2H, d, J=7.8 Hz), 7.96 (IK d, J=7.8 Hz) , 8.03 (1H s), 8.24 (1H, s). 1-4B0 'H-NMR (CDGI3i ppm) (5 7.49-B.02 (15H, m), 8.10 (1H, d, J=7.3 Hz), 8.22 (1H, s). 1-491 MS(APCI)=374(M+1) .1-492 IVlS(APCI)=374(M+l) 1-493 MS(APCI)=408(M+1) 1-494 MS(APGI)=402(MH) 1-495 MS(APCI)=404(M+1) 1-496 MS(APGI)=392(M+1) 1-497 'H-NMRCDlVlSO-de) δ 7.52-7.62 (5Ht m), 7.80 (1H, d, J = 6.8Hz), 7.97-8.00 (2H, m)} 8.05 (1H, d} J =7-8Hz), 8.32 (1H, d, J = 5.9 Hz), 8.38 (1H, s), 8.92 (1H, t, J = 3.9 HzX 10.48-10.54 (2H, m). 1-498 'H-NMR (DMSO~d6) δ 7.51-7.59 (3H, m), 7.80-7.85 (1Hf m), 7.92-7.96 (1Ht m), 8.09 (1H, dd, J = 7.3, 2.0Hz), 8.21 (1H, dd, J = 7.3, 2.0Hz), 8.40 (1H , brs), 8.54 (2H, d, J ^.OHz), 10.38 (1H, s), 10.86 (1H, s).
表 5(15) 化合物編號 物性値 1-^:9 MS(APOI)=368(M+1) 1-500 MS(APCI)=36B(M+t) 1 一細 MS(APCi)=368(M+1) 1-502 MS(APCI)=42t(M+l) 1-503 MS(APC1)=400⑽+1) 1-504 MS(APCI)=338(M+1) 1-505 MS(APCI)=383(M+1) 1-506 MS(APGI)=405(M+i) 1-507 MS(APCI)=419(M+1) 1-508 MS(APCI)=375(M+1) 1-509 MS(APGI)=375 ⑽+1) 1-510 MS(APGI)=356(M-H) 1-511 MS(AP0I)=347(1V1+1) 1-512 MS(APGI)=367(M+1) 1 1-513 MS(APCI)=354(IVl+l) 124 200836629Table 5 (15) Compound number Physical properties ^ 1-^: 9 MS (APOI) = 368 (M + 1) 1-500 MS (APCI) = 36B (M + t) 1 A fine MS (APCi) = 368 (M +1) 1-502 MS(APCI)=42t(M+l) 1-503 MS(APC1)=400(10)+1) 1-504 MS(APCI)=338(M+1) 1-505 MS(APCI) =383(M+1) 1-506 MS(APGI)=405(M+i) 1-507 MS(APCI)=419(M+1) 1-508 MS(APCI)=375(M+1) 1 -509 MS(APGI)=375 (10)+1) 1-510 MS(APGI)=356(MH) 1-511 MS(AP0I)=347(1V1+1) 1-512 MS(APGI)=367(M+ 1) 1 1-513 MS(APCI)=354(IVl+l) 124 200836629
表 5ilQTable 5ilQ
-¾雜編號—— -物性値- 1-514 1 VIS(APCI)=402(M+1) 1-ST5 ^S(APOI)=338(M+1) 1-516 ^S(APCI)=335(M+1) 1-517 ( H-NMR (CDCi3, ppm) d 2.72 (3H, s), 7.48-8.01 (12H, m), 8.41 :1H, d, J=2.0 Hz). 1-518 H-NMRCCDCl3) δ 2.56 (6H, s), 7.13-7.18 (1H, m), 7.24-7.31 :2H, m), 7.50-7.57 (2K m), 7.94 (2Ht d, J =7.3Hz), 8.21 (1H, d, J =7.3Hz), 8.50 (1H, s), 9.43 (1H, d, J =8.8Hz). 1-519 H-NMR(CDGl3) $3.56 (3H, s), 4,05 (6H, s), 7.09 (1H, s), 7.14 (1H, t J =4.9Hz), 7.35 (1H, d, J =5.3Hz), 7.56 (1H, df J =1.5Hz), 7.58 (1H, d, J =1.5Hz), 7.65 (1H, d, J =5.9Hz), 7.73 (1H, s), 8.27 (1H, t J =1.5Hz). 1-520 ^H-NMRCCDCls) ¢3.53 (3H, s), 4.03 (6H, s), 7.16-7.27 (5H, m), 7.28-7.35 (4H, m), 7.66 (*1H, d, J =1.46Hz). 1-521 ^-NMRiCDCIs-DMSO-da) d 7.43-7.53 (5H, m), 7.70 (1H, d, ϋ =7.8Hz), 7.99 (1HT d, J =6.8Hz), 8.17 (1H, d, J =7.8Hz), 8.28 (1H, sX 9.21 (1H, br.s.X 9.70 (1H, br.s.). 1-522 ^H-NrvIRiCDOIg-DrvISO-dg) u 7.13~?.32 (2H, m), 7.45-7.55 (2H, rn), 7.75 (1H, t J =3.9Hz), 7.86-7.90 (1Ht m), 7.94-B.12 (1H, mX 8.25 (1H s), 9.73 (1H, d, J =6.3Hz), 9.86 (1H, br.s.). 1-523 lH-NMR(GDGl3) (52.56 (6H, s), 7.13-7.1B (1H, m), 7.24-7.31 (2H, m), 7.50-7.57 (2K m), 7.94 (2H, d, J =7.3Hz)t 8.21 (1H, d, J =7.3Hz), 8.50 (1H, s), 9.43 (1H, df J =δ.8Ηζλ 1-524 ' H-NMRiCDGls-DMSO-dg) δΖΜ (3H, d, J =4.4Hz), 3.51 (3H, s), 7.20-7.43 (8H, m), 7.74-7.79 (2H, m), 7.99-8.02 (2H, m), 8.75 (1H, d, J=44Hz), 11.9 (1H, s). 1-525 'H-NMR(CDCl3~DMS〇-d5) δ 1.25 (6H, d, J =6.8Hz), 3.53 (3H, s), 4.22 (1H, sep., J =7.8Hz), 6.19 (1H, d, J =7.8Hz), 7.13-7.27 (3H, m), 7.29-7.34 (5H, m), 7.72-7.75 (2H, m), 7.81 (1H, t, J =2.0Hz), 8.01 (1H d.d., J =1.5, 6.8Hz), 11.21 (1H, s). 1-526 lH-NMR(GDGl3-DMS〇-d6) ¢6.82 (1Ht q., J =2.0, 7.2, 6.3, ZOHzX 7.48-7.62 (5H, m), 7.85 (1H, d.d, J =1.5t 6.8, l.OHz), 8.00 (2H, m), 8.25-8.28 (ΊΗ, m), 8.34-8.52 (3H, m)t 8.64 (1H, br.s.), 10.28 (1HT br.s·)· 1-527 'H-NIVIRCCDCIs-DIVISO-dg) δ 3.53 (3H, s\ 7.20-7.27 (3H, m), 7.32 (3H, t, J =7.3Hz), 7.44 (1H, t, J =7.8Hz), 7.54 (1H, t, J =7.8Hz), 7.90-7.91 (tH, m), 7.95-7.98 (1H, m), 8.07-8.13 (3H, m). 1-528 'H-NMRCODCis-DMSO-dei ¢3.46 (3H, s), 7.22-7.31 (4H, m), 7.32-7.34 (2H, m), 7.47-7.53 (2H, t J =7.8Ης), 8.00-8.03 (2H, mX 8.21 (1H, d, ϋ =2.0Hz), 8.43 (1H, t J =1.5Hz). 125 200836629 表 5(17)-3⁄4 杂号号 - - Property 値 - 1-514 1 VIS(APCI)=402(M+1) 1-ST5 ^S(APOI)=338(M+1) 1-516 ^S(APCI)=335 (M+1) 1-517 (H-NMR (CDCi3, ppm) d 2.72 (3H, s), 7.48-8.01 (12H, m), 8.41 :1H, d, J=2.0 Hz). 1-518 H -NMRCCDCl3) δ 2.56 (6H, s), 7.13-7.18 (1H, m), 7.24-7.31 : 2H, m), 7.50-7.57 (2K m), 7.94 (2Ht d, J =7.3Hz), 8.21 ( 1H, d, J = 7.3 Hz), 8.50 (1H, s), 9.43 (1H, d, J = 8.8 Hz). 1-519 H-NMR (CDGl3) $3.56 (3H, s), 4,05 (6H , s), 7.09 (1H, s), 7.14 (1H, t J = 4.9Hz), 7.35 (1H, d, J = 5.3Hz), 7.56 (1H, df J =1.5Hz), 7.58 (1H, d , J = 1.5 Hz), 7.65 (1H, d, J = 5.9 Hz), 7.73 (1H, s), 8.27 (1H, t J = 1.5 Hz). 1-520 ^H-NMRCCDCls) ¢3.53 (3H, s), 4.03 (6H, s), 7.16-7.27 (5H, m), 7.28-7.35 (4H, m), 7.66 (*1H, d, J = 1.46Hz). 1-521 ^-NMRiCDCIs-DMSO- Da) d 7.43-7.53 (5H, m), 7.70 (1H, d, ϋ = 7.8Hz), 7.99 (1HT d, J = 6.8Hz), 8.17 (1H, d, J = 7.8Hz), 8.28 (1H , sX 9.21 (1H, br.sX 9.70 (1H, br.s.). 1-522 ^H-NrvIRiCDOIg-DrvISO-dg) u 7.13~?.32 (2H, m), 7.45-7.55 (2H, rn ), 7.75 (1H, t J = 3.9Hz), 7.86-7.90 (1Ht m), 7.94-B.12 (1H, mX 8.25 (1H s), 9.73 (1H, d, J = 6.3 Hz), 9.86 (1H, br.s.). 1-523 lH-NMR(GDGl3) (52.56 (6H , s), 7.13-7.1B (1H, m), 7.24-7.31 (2H, m), 7.50-7.57 (2K m), 7.94 (2H, d, J = 7.3 Hz) t 8.21 (1H, d, J = 7.3 Hz), 8.50 (1H, s), 9.43 (1H, df J = δ.8Ηζλ 1-524 'H-NMRiCDGls-DMSO-dg) δΖΜ (3H, d, J = 4.4 Hz), 3.51 (3H, s), 7.20-7.43 (8H, m), 7.74-7.79 (2H, m), 7.99-8.02 (2H, m), 8.75 (1H, d, J=44Hz), 11.9 (1H, s). 1- 525 'H-NMR (CDCl3~DMS〇-d5) δ 1.25 (6H, d, J = 6.8 Hz), 3.53 (3H, s), 4.22 (1H, sep., J = 7.8 Hz), 6.19 (1H, d, J = 7.8 Hz), 7.13-7.27 (3H, m), 7.29-7.34 (5H, m), 7.72-7.75 (2H, m), 7.81 (1H, t, J = 2.0Hz), 8.01 (1H Dd, J = 1.5, 6.8 Hz), 11.21 (1H, s). 1-526 lH-NMR(GDGl3-DMS〇-d6) ¢6.82 (1Ht q., J =2.0, 7.2, 6.3, ZOHzX 7.48-7.62 (5H, m), 7.85 (1H, dd, J = 1.5t 6.8, l.OHz), 8.00 (2H, m), 8.25-8.28 (ΊΗ, m), 8.34-8.52 (3H, m)t 8.64 ( 1H, br.s.), 10.28 (1HT br.s·)· 1-527 'H-NIVIRCCDCIs-DIVISO-dg) δ 3.53 (3H, s\ 7.20-7.27 (3H, m), 7.32 (3H, t , J = 7.3Hz), 7.44 (1H, t, J = 7.8Hz ), 7.54 (1H, t, J = 7.8 Hz), 7.90-7.91 (tH, m), 7.95-7.98 (1H, m), 8.07-8.13 (3H, m). 1-528 'H-NMRCODCis-DMSO -dei ¢ 3.46 (3H, s), 7.22-7.31 (4H, m), 7.32-7.34 (2H, m), 7.47-7.53 (2H, t J = 7.8Ης), 8.00-8.03 (2H, mX 8.21 ( 1H, d, ϋ =2.0Hz), 8.43 (1H, t J =1.5Hz). 125 200836629 Table 5(17)
_ 合物編號一- —物性値—. I 1-529 — H-NMR(CDCl3-DMS〇-d6) 53.43 (3H, s), 7.Z1-7.29 (4H, m), 7.30-7.32 (2H, m), 7.44-7.49 (2H, m), 7.98-8.00 (2H, m), 8.05 ΊΗ, d, ϋ =2.0Hz), 8.19 (1H, t J =2.4, 1.0Hz). 1-530 H-NMR (GDC!3, ppm) $ 3.11 (3H, s), 3.56 (3H, s), 7.21-7.34 :6H, m), 7.42 (1H, t J=8.3 Hz), 7.60 (1H, brs), 7.63 (1H, brs), 7.71 (1K dd, J=1.5 Hz, J=8.3 Hz), 7.96 (2K s). 1-531 H-NMR (GDCI3) δ 2.07 (3H, s), 2.18 (3H, s), 3.19-3.50 (3H, m), 6.09-7.84 (8H, m), 8.00 (2H, s). 1-532 'H-NMR (DMS〇-d6) δ 2.50 (3H, s), 3.39 (3H, s), 3.42 (3H, s), 6.30-7.30 (8H, m), 7.72 (2H s). 1-533 'H-NMR (DMS〇-d6) δ 3.17 (3H, s), 3.22 (3H, s), 3.72 (3H, s\ -6.52-7.76 (11H, m), 1-534 Ή-NMR (CDCi3) δ 1.02(3H, t, J = 7.3Hz), 1.65(2H, tq, J = 7.3, 7.3Hz), 2.87(2H, t, ϋ = 7.3Hz), 7.Z1(1H, dd, ϋ = 8.3, 11.7Hz), 7.31-7.34(3H, m), 7.49(1 H, t, J = 8.3Hz), 7.53-7.57(1 H, m), 7.69-7.74 (3H,m),8.04-8.08(2H, m), 8.14(1H,s),9.11(1H,d,J = 11.7Hz), 9.27(1 H, s). 1-535 Ή-NMR (CDCI3) δ 1.05(3H, %ό = 7~3Hz), 1.66-1.79(2H, m), 2·72-2·86(2Η, m), 7.22(1H, t J = 8.3Hz), 7.3卜7.340H, m), 7.50 (1H, t J = 8.3Hz), 7.55-7.56(1H, m), 7.61(2H, d, J = 8.8Hz), 7.75 (1H d, J = 8.3Hz)f 7.98(2H, df J = 8.8Hz), 8.06-8.08(2H, m)( 8.17 (IK s), 9.06(1H, d, J = 11.7Hz), 9.65(1 H, s)., 1-536 lH-N!VlR (CDGI3) δ 1.06(3H, t, J = 7.3Hz), 1.72(2H, tq, J = 7.3, 7.3Hz), 2.93(2H, t, J = 7.3Hz), 7.19-7.25(1H, m), 7.35(1H, t, J = 7.8Hz), 7.52C2H, s), 7.53-7.59(2H, m), 7.72(1H, s), 7.76(1H, d, J = 7.8Hz), 7.96(1 H d, J = 8.3Hz), 8.19(1 H, t, J = 6.3Hz), 8.27(1 H, s), 8.62(1H, d, J = 16.1Hz). 1-537 'H-NMR (GDCi3) δ 1.07(3H, t J = 7.3Hz), 1.8〇-1.86(2H, m), 3.12 (2H t J = 7.3Hz), 7.20-7.23(1H, m), 7.38(1H, t J = 7.3HzX 7.54-7.58(2H( m), 7.79(1H, d, J = 8.3Hz), 7.90(1H, dt J = 7.8Hz), 7.98 (1H, s), 8.16(2H? s), 8.18-B.20(1H, mX 8.38(1H, s)5 8.6(1H5 d). 1-538 'H-NMR (CDCi3) δ 1.11(3H, t, J = 7.3HzX 1.72-1.91 (2H, m), 2.64-2.86(2H, m), 7.20-7.23(1 H, m), 7.35(1 H, t, J = 7.3Hz), 7.53-7.57 (2H, mX 7.79(1H, d, ϋ = 7.5Hz), 7.85(2H, s), 7.95(1H, d, J = 7.8Hz)T 8.05(1H, s), 8.20(1Ht t J = 7.3Hz), 8.33(1H, s), 8.64(1H, d, J = 16.0Hz). 126 200836629表 5(18)_ Compound No. 1 - Physical Properties - I 1-529 - H-NMR (CDCl3-DMS〇-d6) 53.43 (3H, s), 7.Z1-7.29 (4H, m), 7.30-7.32 (2H , m), 7.44-7.49 (2H, m), 7.98-8.00 (2H, m), 8.05 ΊΗ, d, ϋ =2.0Hz), 8.19 (1H, t J =2.4, 1.0Hz). 1-530 H -NMR (GDC! 3, ppm) $ 3.11 (3H, s), 3.56 (3H, s), 7.21-7.34 :6H, m), 7.42 (1H, t J=8.3 Hz), 7.60 (1H, brs) , 7.63 (1H, brs), 7.71 (1K dd, J=1.5 Hz, J=8.3 Hz), 7.96 (2K s). 1-531 H-NMR (GDCI3) δ 2.07 (3H, s), 2.18 (3H , s), 3.19-3.50 (3H, m), 6.09-7.84 (8H, m), 8.00 (2H, s). 1-532 'H-NMR (DMS〇-d6) δ 2.50 (3H, s), 3.39 (3H, s), 3.42 (3H, s), 6.30-7.30 (8H, m), 7.72 (2H s). 1-533 'H-NMR (DMS〇-d6) δ 3.17 (3H, s), 3.22 (3H, s), 3.72 (3H, s\ -6.52-7.76 (11H, m), 1-534 Ή-NMR (CDCi3) δ 1.02(3H, t, J = 7.3Hz), 1.65(2H, tq , J = 7.3, 7.3Hz), 2.87(2H, t, ϋ = 7.3Hz), 7.Z1(1H, dd, ϋ = 8.3, 11.7Hz), 7.31-7.34(3H, m), 7.49(1 H , t, J = 8.3Hz), 7.53-7.57(1 H, m), 7.69-7.74 (3H,m), 8.04-8.08(2H, m), 8.14(1H,s),9.11(1H,d, J = 11.7Hz), 9.27(1 H, s). 1-535 Ή-N MR (CDCI3) δ 1.05 (3H, %ό = 7~3Hz), 1.66-1.79(2H, m), 2·72-2·86(2Η, m), 7.22(1H, t J = 8.3Hz), 7.3 7.340H, m), 7.50 (1H, t J = 8.3Hz), 7.55-7.56(1H, m), 7.61(2H, d, J = 8.8Hz), 7.75 (1H d, J = 8.3Hz) f 7.98(2H, df J = 8.8Hz), 8.06-8.08(2H, m)( 8.17 (IK s), 9.06(1H, d, J = 11.7Hz), 9.65(1 H, s)., 1- 536 lH-N!VlR (CDGI3) δ 1.06(3H, t, J = 7.3Hz), 1.72(2H, tq, J = 7.3, 7.3Hz), 2.93(2H, t, J = 7.3Hz), 7.19- 7.25(1H, m), 7.35(1H, t, J = 7.8Hz), 7.52C2H, s), 7.53-7.59(2H, m), 7.72(1H, s), 7.76(1H, d, J = 7.8 Hz), 7.96 (1 H d, J = 8.3 Hz), 8.19 (1 H, t, J = 6.3 Hz), 8.27 (1 H, s), 8.62 (1H, d, J = 16.1 Hz). 1- 537 'H-NMR (GDCi3) δ 1.07(3H, t J = 7.3Hz), 1.8〇-1.86(2H, m), 3.12 (2H t J = 7.3Hz), 7.20-7.23(1H, m), 7.38 (1H, t J = 7.3HzX 7.54-7.58(2H( m), 7.79(1H, d, J = 8.3Hz), 7.90(1H, dt J = 7.8Hz), 7.98 (1H, s), 8.16(2H s), 8.18-B.20(1H, mX 8.38(1H, s)5 8.6(1H5 d). 1-538 'H-NMR (CDCi3) δ 1.11(3H, t, J = 7.3HzX 1.72-1.91 (2H, m), 2.64-2.86(2H, m), 7.20-7.23(1 H, m), 7.35(1 H, t, J = 7.3Hz), 7.53-7.57 (2H, mX 7.79(1H, d, ϋ = 7.5Hz), 7.85(2H, s), 7.95(1H, d, J = 7.8Hz)T 8.05(1H, s), 8.20(1Ht t J = 7.3 Hz), 8.33 (1H, s), 8.64 (1H, d, J = 16.0 Hz). 126 200836629, Table 5 (18)
—北合物編號-- 物性値 i 1-539 1 H-NMR (CDCl3) δ 7.19(1H, d, J = 8.3Hz), 7.34(1H, t, J = 8.3Hz), .41-7.59(9H, m), 7.65(1 HT s), 7.74(1 H, d, J = 7.3HzX 7.96(1 H, d, =7.3Hz), 8.18(1H, dt, J = 8.3Hz), 8.60(tH? s), 8.62(1H, s). \ 1-540 c H-NMRCGDCIs) 5 ?.39-7.41(4H, m), 7.42-7,59(7H, mX 7.67(1H, s), 7.72(1H, if J = 7.3Hz), 7.8B-7.90(2H, m), 7.98(1 H, d, J = 8.3Hz), L04(1H, s), 8.22(1 H, s). 1-541 ( H-NMR (CDCl3) 5 4.18C2H, s), 7.44(2H, d, J = 7.8Hz), 7.50-7.61 8H, m), 7.74(1H, d, J = 7.8Hz), 7.78(1H, s), 7.88-7.94(3H, m), 5.03(1 H, s), 8.27(1 H, s). 1-542 H-NMR (CDC!3) d 4.18(2H, s), 7.19-7.25(1H, mX 7.35(1H, t, J = 7.3Hz), 7.44(2H, d, J = 7.5Hz), 7.52C2H, s), 7.54-?.5B(2H, m), 7.60 ;2H, d, J = 7.8Hz), 7.75-7.77C2H, m), 7.92(1H, d, J = 6.BHz), 8.19 :1H, t J = 7.8Hz), 8.30(1H, s), 8.65(1H s). 1-543 Ή-NMR (CDC[3) d 4.18(2H, s), 7.41-7.46(3H, m), 7.51 (2H, s), 7.55(1 H, t, ϋ = 7.8Hz), ?.60(2H, d, ϋ = 7.8Hz), 7.72(1 H, s), 7.77 (1H, d, J = 7.8Hz), 7.9K1H, d, J = 7.8Hz), 8.2K1H, d, J = 2.0Hz), 8.24(1H, d, J = 8.3Hz), 8.42(1H, s), 8.54(1H s). 1-544 1 H-NMR (CDGi3) δ 4.13(2H} s), 7.46-7.54(5K m), 7.80(2H, d, J = 8,3Hz),7.790H,d,J = 8.3Hz), 8·22—8.26(4H, m), 8·32(2Η, d, J = 9.3Hz)5 8.95C1H, s), l0.18(1Ht s). 1-545 Ή-NMR (CDCI3) δ 4.16(2^ s), 7.13-7.20(2H, m), 7.40-7.46 (4H, m), 7.52(1H, t, J = Ε.3Ηζ), 7.60(2H, d, J = 8.3Hz), 7.71(1H, d, J = 7.3Hz), 7.82(1H, s), 7.86-7.93(2H, m)( 7.98(1H, d, J = 7.8Hz)f 8.21 (2H, d, J = 9.3Hz). 1-546 'H-NMR (CDCi3) δ 3.48(2Hf qf J = 9.8Hz), 7.49-7.6〇(4H, m), 7.69 (2H, s), 7.73(1H, d, J = 7.8Hz), 7.87-7.90(3H, m), 7.95(1H} d, J = 7.8Hz), 8.14C1H, s), 8.27(1H, s). 1-547 Ή-NMR (CDCi3) δ 3.49(2K,q, J = 9.8Hz), 7.20-7.25(1 H, m), 7.35 (1H, t J = 7.8Hz)T 7.52-7.58(2H, m), 7.74(2H, s), 7.76(tH, d, J = 7.8Hz), T.BSdH, s)t ?.92(1H, d, J = 7.8Hz), 8.19(1H, t, J = 7.8Hz), 8.31 (1H, s), 8.64(1 H, d, J = 15.6Hz). 1-548 Ή-NMR (CDCI3) d 3.49(2H, q, J = 9.8Hz), 7.42-7.45(1 H, m), 7.54 (1H, t J = 7.3Hz),7.73(2H,s), 7.77-7.79(2H, m),7.92(1H,d,J = 7.8Hz), 8.21-8.23(1H, m), 8.26(1H, s), 8.43(1H, s), 8.53-8.55(1 H, m). 1-549 lH-NMR (CDCI3) δ 3.54(ZH, q, J = 9.3Hz)t 7.52(1H, t J = 7.8Hz), 7.73(2H, s), 7.82(1 H, d, J = 7.8Hz), 8.23-8.27(4H, m), 8.32(2H, d, J = 9.3Hz), 0.33C1H, s), 10.29(tH, s). 1-550 1 H-NMR (GDC13, ppm) δ 3.57 (3Hf s), 7.22-7.33 (6Ht m), 7.43 (1H, t ^=7.8 Hz), 7.67 (1H, s), 7J2-7.78 (2H, m), 8.30 (2H, s). 1-551 ' H-NMR (GDCI3i ppm) δ 3.56 (3H, s), 7.21-7.34 (6H, m), 7.41 (1H, t J=7.8 Hz), 7.46 (1H, brs)? 7.60 (1H, s), 7.69 (1H, d, J=1.5 Hz), 7.70 (2H, s). 1-552 Ή-NMR (CDGI3l ppm) δ 3.99 (2H, brs), 6.66 (2H, s), 6.95-7.02 (4H m), 7.72 (1H, d, J=7.3 Hz), 7.93-7.96 (3H, m), 8.08 (1H, d, J=8.3 Hz), 8.25 (1H, s), 8.85 (1H, s). 1-553 Ή-NMR (DMSO-de) δ 3.88(3H, s), 7.48~7.57(4H, m)t 7.71(2H, d, J = B.3Hz), 7.82(1 H, d, J = 7.8Hz), 8.02(2H dt J = 8.3Hz), B,10 (2Ht d, d = 8.3HzX 8.17(1H, d, J = 8.3Hz), B.4K1H, s), 10.06(1H, s), 10.9(1 H, si 127 200836629 表5(1釣— 北合编号-- Physical properties 値i 1-539 1 H-NMR (CDCl3) δ 7.19(1H, d, J = 8.3Hz), 7.34(1H, t, J = 8.3Hz), .41-7.59( 9H, m), 7.65(1 HT s), 7.74(1 H, d, J = 7.3HzX 7.96(1 H, d, =7.3Hz), 8.18(1H, dt, J = 8.3Hz), 8.60(tH s), 8.62(1H, s). \ 1-540 c H-NMRCGDCIs) 5 ?.39-7.41(4H, m), 7.42-7,59(7H, mX 7.67(1H, s), 7.72( 1H, if J = 7.3Hz), 7.8B-7.90(2H, m), 7.98(1 H, d, J = 8.3Hz), L04(1H, s), 8.22(1 H, s). 1-541 (H-NMR (CDCl3) 5 4.18C2H, s), 7.44 (2H, d, J = 7.8 Hz), 7.50-7.61 8H, m), 7.74 (1H, d, J = 7.8 Hz), 7.78 (1H, s), 7.88-7.94(3H, m), 5.03(1 H, s), 8.27(1 H, s). 1-542 H-NMR (CDC!3) d 4.18(2H, s), 7.19-7.25 (1H, mX 7.35(1H, t, J = 7.3Hz), 7.44(2H, d, J = 7.5Hz), 7.52C2H, s), 7.54-?.5B(2H, m), 7.60 ;2H, d , J = 7.8Hz), 7.75-7.77C2H, m), 7.92(1H, d, J = 6.BHz), 8.19 :1H, t J = 7.8Hz), 8.30(1H, s), 8.65(1H s 1-543 Ή-NMR (CDC[3) d 4.18(2H, s), 7.41-7.46(3H, m), 7.51 (2H, s), 7.55(1 H, t, ϋ = 7.8Hz), ?.60(2H, d, ϋ = 7.8Hz), 7.72(1 H, s), 7.77 (1H, d, J = 7.8Hz), 7.9K1H, d, J = 7.8Hz), 8 .2K1H, d, J = 2.0Hz), 8.24(1H, d, J = 8.3Hz), 8.42(1H, s), 8.54(1H s). 1-544 1 H-NMR (CDGi3) δ 4.13(2H } s), 7.46-7.54(5K m), 7.80(2H, d, J = 8,3Hz), 7.790H,d,J = 8.3Hz), 8.22—8.26(4H, m), 8·32 (2Η, d, J = 9.3Hz)5 8.95C1H, s), l0.18(1Ht s). 1-545 Ή-NMR (CDCI3) δ 4.16(2^ s), 7.13-7.20(2H, m) , 7.40-7.46 (4H, m), 7.52 (1H, t, J = Ε.3Ηζ), 7.60(2H, d, J = 8.3Hz), 7.71(1H, d, J = 7.3Hz), 7.82(1H , s), 7.86-7.93(2H, m)( 7.98(1H, d, J = 7.8Hz)f 8.21 (2H, d, J = 9.3Hz). 1-546 'H-NMR (CDCi3) δ 3.48( 2Hf qf J = 9.8Hz), 7.49-7.6〇(4H, m), 7.69 (2H, s), 7.73(1H, d, J = 7.8Hz), 7.87-7.90(3H, m), 7.95(1H} d, J = 7.8 Hz), 8.14C1H, s), 8.27(1H, s). 1-547 Ή-NMR (CDCi3) δ 3.49 (2K, q, J = 9.8 Hz), 7.20-7.25 (1 H, m), 7.35 (1H, t J = 7.8Hz)T 7.52-7.58(2H, m), 7.74(2H, s), 7.76(tH, d, J = 7.8Hz), T.BSdH, s)t ? .92(1H, d, J = 7.8Hz), 8.19(1H, t, J = 7.8Hz), 8.31 (1H, s), 8.64(1 H, d, J = 15.6Hz). 1-548 Ή- NMR (CDCI3) d 3.49 (2H, q, J = 9.8 Hz), 7.42-7.45 (1 H, m), 7.54 (1H, t J = 7.3 Hz), 7.73 ( 2H, s), 7.77-7.79 (2H, m), 7.92 (1H, d, J = 7.8 Hz), 8.21-8.23 (1H, m), 8.26 (1H, s), 8.43 (1H, s), 8.53 -8.55(1 H, m). 1-549 lH-NMR (CDCI3) δ 3.54 (ZH, q, J = 9.3 Hz) t 7.52 (1H, t J = 7.8 Hz), 7.73 (2H, s), 7.82 (1 H, d, J = 7.8 Hz), 8.23-8.27 (4H, m), 8.32 (2H, d, J = 9.3 Hz), 0.33C1H, s), 10.29(tH, s). 1-550 1 H-NMR (GDC13, ppm) δ 3.57 (3Hf s), 7.22-7.33 (6Ht m), 7.43 (1H, t ^=7.8 Hz), 7.67 (1H, s), 7J2-7.78 (2H, m), 8.30 (2H, s). 1-551 'H-NMR (GDCI3i ppm) δ 3.56 (3H, s), 7.21-7.34 (6H, m), 7.41 (1H, t J=7.8 Hz), 7.46 (1H, Brs) 7.60 (1H, s), 7.69 (1H, d, J=1.5 Hz), 7.70 (2H, s). 1-552 Ή-NMR (CDGI3l ppm) δ 3.99 (2H, brs), 6.66 (2H , s), 6.95-7.02 (4H m), 7.72 (1H, d, J=7.3 Hz), 7.93-7.96 (3H, m), 8.08 (1H, d, J=8.3 Hz), 8.25 (1H, s ), 8.85 (1H, s). 1-553 Ή-NMR (DMSO-de) δ 3.88(3H, s), 7.48~7.57(4H, m)t 7.71(2H, d, J = B.3Hz), 7.82(1 H, d, J = 7.8Hz), 8.02(2H dt J = 8.3Hz), B,10 (2Ht d, d = 8.3HzX 8.17(1H, d, J = 8.3Hz), B.4K1H, s), 10.06(1H, s), 10.9(1 H, si 127 200836629 Table 5 (1 fishing
—化雜編號—- -物_ j 1-554 c ( H-NMR (DMS〇-d6) δ 2.09 (3Η, s), 7.50-7.63 (4H, m), 7.75 (1H, l, J=7.8 Hz), 7.79 (2H, s), 7.99-8.06 (3H, m), 8.35 (1H, s), 10.2 1K s), 10.3 (1H, si 10.5 (1H, s). I 1-555 ( ( H-NMR (.CDGI3) δ .7.40(2Η,t J = 7.3Hz),7·47-7.52(5Η, m),7.57 1H,t J = 7.3Hz),7·64(2Η,s),7.74(1H,d,J = 8.3Hz),7.87-7.97 6H, m), 8.25(1 H, d, J = 8.3Hz), 8.86(^, brs). 1 1-556 H-NMR (CDGi3, ppm) d 3.01 (3H, d, J=4.8 Hz), 3.56 (3H. s), 6.27 1H, d, J=4.8 HzX 7.19-7.33 (6H, m), 7.38 (1H, t, J=7.8 Hz), 7.58 ΊΗ, br), 7.65 (1H, s), 7.72 (1H, d, J=7.8 Hz), 7.94 (2H, s). 1-558 H-NMR (DMS〇-d6) δ 3.80(3H, s), 7.40-7.43(1 H, m), 7.50(1 H, t J = 7.8Hz), 7.76(1H, s), 7.81(1H, d, J = 7.8Hz), 7.94(1K d, J = 7.8Hz), 8.1K1H, dt J = 8.3, 2.0Hz), 8.33(1 H, t J = 2.0Hz), 8.51 :1H, dd, J = 8.3, 2.0Hz), 10.48(1H, s), 10.78(1H, s). 1-559 H-NMR (DMS〇-d6) δ 3.80(3H, s), 7.2K1H, dd, J = 8.3, 10.2Hz), 7.30(1H, dd, J = 6.8, 7.8Hz), 7.51-7.55(2H, m), 7.76(1H, s), 7.81 (1H, ddT ϋ = 1.5, 7.8HzX 7.93(1H, d, J = 1.5Hz), 8.12(1Ht d, J = 8.3Hz), 8.33(1H s), 9.62(1H, d J = 7.8Hz), 10.78(1H, s). 1-560 lH-NiviRiCDCI3) δ t.68(SHf s), 7.48-7.54(3H, m), 7.58(1 H, d, J = 7.8Hz), 7.68(1 Ht d, J = 7.BHz), 7.78(1H, s), 7.86-7.92(3H, m), 7.97C1H, s), 8.1K1H, s), 8.25(1H, s). 1-562 'H-NMR (GDCi3, ppm) δ 3.44 (3H, s), 7.23-7.30 (5H, m), 7.41-7.45 (2H, m)f 7.71 (1H, brs)f 7.77 (1H, d, J=6.3 Hz), 7.80 (1H, s), 8.02 (2H s), 8.22 (1H, s), 10.4 (1H, s). 1-563 1 H-NMR (CDCI3i ppm) δ 3.57 (3H, s), 7.21-7.44 (8H, m), 7.61 (1H, s), 7.72 (1H, d, J=7.8 Hz), 8.01 (2H, s), 8.13 (1H, s), 8.58 (IK s). 1-564 1 H-NMR (CDCI3, ppm) <5 3.57 (3H, s), 7.21-7.30 (7H, m), 7.34 (1H, dt, J=7.3 Hz, J=1.5 Hz), 7.41 (1H, t J=7.3 Hz), 7.87 (1H, s), 7.96 (1H dt, J=t5 Hz, J=8.3 Hz), 8.17 (1H, d, J=1.5 Hz), 8.35 (1H s), 8.65 (1H d, J=7.8 Hz) 1-565 lH-NMR(CDCI3, ppm) δ 7.53-7.62 (4H, m), 7.81 (1H, d, J=7.8 Hz), 8.00-8.02 (2H, m), 8.07 (1H, d, J=7.3 Hz), 8.40 (1H, s), 8.5? (2H, s), 9.90 (1H, s), 10.49 (1H, s), 1Q.51 (1H, s). 1-566 'H-NMR (GDCi3) δ 2.48(3H, s), 7.05(1 H s), 7.23(1 Ht s), 7.50-7.62 (4H, m), 7.69(1 H, d, J = 7.8Hz), 7.84(1 H, dd, J = 2.0, 7.8Hz), 7.B9 (2H, d,vl = 6·8Ηζ),s), 8.18(1H, d, J = 6·8Ηζ1 8·39(1Η,t d = 1.9Hz), 8.89(1 H, s). 1-567 1 H-NMR (CDCI3) δ 2.33(3H, s), 3.56(3H, s), 7.03(1 H, s), 7.22-7.38 (6H, m), 7.45C1H, t J = 7.8Hz), 7.58(1H, s), 7.62(1H, s), 7.67C1H, d, J = 7.8Ης), 8,63(1 H, s). 1-568 ! H-NMR (CDC!3) δ 2.37(3H, s)t 3.21 (3H, s), 3.56(3H, s\ 7.20-7.29 (4H, m), 7.33-7.4K4H, m), 7.52(1H, s), 7.69(1H, d, ϋ = 7.8Hz), 7.72 (in s), a3〇oa s)_ 1-569 1 H-NMR (GDCI3) δ 2.38(3H, s)T 3.56(3H, s), 7.19-7.33(6H, m), 7.38-7.40(2H, m), 7.42(1H, s), 7.57(1H, s), 7.61(1H, s), 7.66(1H, d, J = 7.8Hz). 1-570 1 H-NMR (CDCIs) δ 2.03(3H, s), 2.37(3H, s), 3.55(3H, s), 6.75 (1K s), 7,20-7.44(9H, m), ?.92(1H, s), 7.99(1K d, J = 7.8Hz). 128 200836629 表 5(2Q)- Adding the number - - - _ j 1-554 c (H-NMR (DMS 〇-d6) δ 2.09 (3Η, s), 7.50-7.63 (4H, m), 7.75 (1H, l, J=7.8 Hz), 7.79 (2H, s), 7.99-8.06 (3H, m), 8.35 (1H, s), 10.2 1K s), 10.3 (1H, si 10.5 (1H, s). I 1-555 ( ( H -NMR (.CDGI3) δ .7.40 (2Η, t J = 7.3Hz), 7·47-7.52 (5Η, m), 7.57 1H, t J = 7.3Hz), 7·64(2Η, s), 7.74 (1H,d,J = 8.3Hz), 7.87-7.97 6H, m), 8.25(1 H, d, J = 8.3Hz), 8.86(^, brs). 1 1-556 H-NMR (CDGi3, ppm ) d 3.01 (3H, d, J=4.8 Hz), 3.56 (3H. s), 6.27 1H, d, J=4.8 HzX 7.19-7.33 (6H, m), 7.38 (1H, t, J=7.8 Hz) , 7.58 ΊΗ, br), 7.65 (1H, s), 7.72 (1H, d, J=7.8 Hz), 7.94 (2H, s). 1-558 H-NMR (DMS〇-d6) δ 3.80 (3H, s), 7.40-7.43(1 H, m), 7.50(1 H, t J = 7.8Hz), 7.76(1H, s), 7.81(1H, d, J = 7.8Hz), 7.94(1K d, J = 7.8Hz), 8.1K1H, dt J = 8.3, 2.0Hz), 8.33(1 H, t J = 2.0Hz), 8.51 :1H, dd, J = 8.3, 2.0Hz), 10.48(1H, s), 10.78(1H, s). 1-559 H-NMR (DMS〇-d6) δ 3.80(3H, s), 7.2K1H, dd, J = 8.3, 10.2Hz), 7.30(1H, dd, J = 6.8, 7.8Hz), 7.51-7.55(2H, m), 7.76(1H, s), 7 .81 (1H, ddT ϋ = 1.5, 7.8HzX 7.93(1H, d, J = 1.5Hz), 8.12(1Ht d, J = 8.3Hz), 8.33(1H s), 9.62(1H, d J = 7.8Hz ), 10.78(1H, s). 1-560 lH-NiviRiCDCI3) δ t.68(SHf s), 7.48-7.54(3H, m), 7.58(1 H, d, J = 7.8Hz), 7.68(1) Ht d, J = 7.BHz), 7.78(1H, s), 7.86-7.92(3H, m), 7.97C1H, s), 8.1K1H, s), 8.25(1H, s). 1-562 'H -NMR (GDCi3, ppm) δ 3.44 (3H, s), 7.23-7.30 (5H, m), 7.41-7.45 (2H, m)f 7.71 (1H, brs)f 7.77 (1H, d, J=6.3 Hz ), 7.80 (1H, s), 8.02 (2H s), 8.22 (1H, s), 10.4 (1H, s). 1-563 1 H-NMR (CDCI3i ppm) δ 3.57 (3H, s), 7.21- 7.44 (8H, m), 7.61 (1H, s), 7.72 (1H, d, J=7.8 Hz), 8.01 (2H, s), 8.13 (1H, s), 8.58 (IK s). 1-564 1 H-NMR (CDCI3, ppm) <5 3.57 (3H, s), 7.21-7.30 (7H, m), 7.34 (1H, dt, J = 7.3 Hz, J = 1.5 Hz), 7.41 (1H, t J =7.3 Hz), 7.87 (1H, s), 7.96 (1H dt, J=t5 Hz, J=8.3 Hz), 8.17 (1H, d, J=1.5 Hz), 8.35 (1H s), 8.65 (1H d , J=7.8 Hz) 1-565 lH-NMR (CDCI3, ppm) δ 7.53-7.62 (4H, m), 7.81 (1H, d, J=7.8 Hz), 8.00-8.02 (2H, m), 8.07 ( 1H, d, J=7.3 Hz), 8.40 (1H, s), 8.5? (2H, s), 9.9 0 (1H, s), 10.49 (1H, s), 1Q.51 (1H, s). 1-566 'H-NMR (GDCi3) δ 2.48(3H, s), 7.05(1 H s), 7.23( 1 Ht s), 7.50-7.62 (4H, m), 7.69 (1 H, d, J = 7.8 Hz), 7.84 (1 H, dd, J = 2.0, 7.8 Hz), 7.B9 (2H, d, Vl = 6·8Ηζ), s), 8.18(1H, d, J = 6·8Ηζ1 8·39(1Η, td = 1.9Hz), 8.89(1 H, s). 1-567 1 H-NMR (CDCI3 δ 2.33(3H, s), 3.56(3H, s), 7.03(1 H, s), 7.22-7.38 (6H, m), 7.45C1H, t J = 7.8Hz), 7.58(1H, s), 7.62(1H, s), 7.67C1H, d, J = 7.8Ης), 8,63(1 H, s). 1-568 ! H-NMR (CDC!3) δ 2.37(3H, s)t 3.21 ( 3H, s), 3.56(3H, s\ 7.20-7.29 (4H, m), 7.33-7.4K4H, m), 7.52(1H, s), 7.69(1H, d, ϋ = 7.8Hz), 7.72 (in s), a3〇oa s)_ 1-569 1 H-NMR (GDCI3) δ 2.38(3H, s)T 3.56(3H, s), 7.19-7.33(6H, m), 7.38-7.40(2H, m ), 7.42 (1H, s), 7.57 (1H, s), 7.61 (1H, s), 7.66 (1H, d, J = 7.8 Hz). 1-570 1 H-NMR (CDCIs) δ 2.03 (3H, s), 2.37(3H, s), 3.55(3H, s), 6.75 (1K s), 7,20-7.44(9H, m), ?.92(1H, s), 7.99(1K d, J = 7.8Hz). 128 200836629 Table 5 (2Q)
—化合ί編號— 物讎 i 1-571 ( H-NMR(DMS〇-d6) δ 2.30(3Η, sX 4.55(2HS d, J = Z.9Hz), 5.48 1H,broad), 7.5卜7.60(5H,m), 7.69-7.73(2H,m),7·98-8·00(2Η,m), 8.06(1 H, dd, J = 1.5,8.3Hz), 8.35(1 H, t, ϋ = 1.5Hz), 9.93(1 H, s), i 0.48(lH, s). 1-572 .( H-NMR(CDCi3) δ 2.31 (3H, s), 3.36(3H, s), 3.53(3H, s), 4.44 :2H, s), 7.17-7.40(8H, m), 7.49(1 H, s), 7.67-7.71(2H, m), 8.69 ΊΗ. si 1-573 H-NMR(DMS〇-d6) δ 1.96(3H, s), 3.84(2H5 broad), 7.53-7.63 C4H, m), 7.73(1 H, d, J = 7.8Hz), 7.89(1 H, s), 7.99-8.01 (2H, m), 8.07C1H, dd, J = 1.5,7.8Hz), 8.19(1H, s), 8.33(1H, t, J = 2.0Hz), 10.43(1 H, s), 10.49(1 H, s). 1-574 'H-NMRCCDCIs) δ 7.31(1H, d, J = 2.9Hz), 7.41(1H, d, J = Z.9Hz), 7.50-7.6K4H, m), 7.65(1H, broad-s), 7.74(1H, df J = 7.8Hz), 7.81 (1H, d5 J = 2.0Hz), 7.88-7.9K2H, m), 8.01-8.05(3H, m), 8.23(1H, broad - s). 1-575 'H-NMR(DMS〇-d6) δ 2.30(3H, s), 3.56(3H, s), 6.32(1 H, septet, J=5.9Hz), 6.85(1H, s), 7.19-7.43(8H, m), 7.58(1Ht broad-s), 7.70 (1H, d, J = 7.8Hz). 1-576 'H-NMRCDMSO-dg) δ 2.35(3H, s), 7.05(1 H, d, J = 2.4Hz), 7.33 (1H, d, J = 2.4Hz), 7.48-7.59(4H? m), 7.67(1H, broad-s), 7.72(1H, d, ϋ = 7.8HzX 7.88-7.90C2H, m), 7.99-8.03(2H, m), 8.17(1H, broad-s), 8.24(1 H, broad-s), 8.28(1 H, t, J = 1.0Hz). 1-577 lH-NMR(DMS〇-d6) δ 2.40(3H, s), 7.11(1H, d, ϋ = 2.5Hz), 7.20-7.25(1H, m)f 7.3〇-7.37(2H, m)5 7.53-7.5B(2H, m), 7.60(1H, s), 7.76 (1H, d, J = 7.8Hz), 7.97-8.00(2H, m), 8.17-8.Z2(1H, m), B.29(2H, d, J = 8.8HzX 8.61,8.65(1H, two broad-s). 1-578 ' H-NMRCDMSO-dg) δ 2.37(3H? s), 7.01 (2H, t, J = 8.3Hz), 7.09 (1H, d, J = 2.5Hz), 7.35(1H, d, J = 2.5Hz), 7.42-7.46(1H, m)? 7.53 (1Ή, t, J = 8.3Hz), 7.65(1H, s), 7.76(1H, d, J = 7.8Hz), 7.92-8.00 (3H, m), 8.23(1 H, s), 8.29(1 H, s). 1-579 lH-NMR(DMS〇-d6) δ 2.39(3H, s), 7.11(1 H, d, J = .2.4Hz), 7.36 (1H, d, ϋ = 2.4Hz), 7.42-7.44(1H, m), 7.57(1H? t J = 7.8Hz), 7.63 (1H, s), 7.78C1H, d, J = 7.8Hz), 7.95(1H, d, ϋ = 8.3Ης), 7.99(1Ht d, J = 2.0Hz),8.21-8.25(2H, m), 8.29(1H, s), 8.4K1H, s),8.54-8.55 (1H, m). 1-580 lH-NMR(CDCi3) δ 3.560H, s), 7.13(1 H, dd, J = 9.3, 2.4Hz), 7.19-7·23(2Η,m), ?JZ7-7.34(5H, m)t 7·39(1Η, d, J = 8·3Ηζ), 7.6K1H,t, J = 1.5Hz), 7.65(1 H, d, J = 8.3Hz), 7.78(1 H, d} J = 2.4Hz)f 7.98 (1H, d, J = ZAHzl 8.13(1H broad-s), 8.55(1 H d, J = 9.3Hz). 129 200836629 表 5(21)- ί 编号 number - 雠i 1-571 (H-NMR(DMS〇-d6) δ 2.30(3Η, sX 4.55(2HS d, J = Z.9Hz), 5.48 1H, broad), 7.5 7.60 (5H , m), 7.69-7.73 (2H, m), 7·98-8·00 (2Η, m), 8.06 (1 H, dd, J = 1.5, 8.3 Hz), 8.35 (1 H, t, ϋ = 1.5Hz), 9.93(1 H, s), i 0.48(lH, s). 1-572 . (H-NMR(CDCi3) δ 2.31 (3H, s), 3.36(3H, s), 3.53(3H, s), 4.44:2H, s), 7.17-7.40(8H, m), 7.49(1 H, s), 7.67-7.71(2H, m), 8.69 ΊΗ. si 1-573 H-NMR(DMS〇- D6) δ 1.96(3H, s), 3.84(2H5 broad), 7.53-7.63 C4H, m), 7.73(1 H, d, J = 7.8Hz), 7.89(1 H, s), 7.99-8.01 (2H , m), 8.07C1H, dd, J = 1.5, 7.8Hz), 8.19(1H, s), 8.33(1H, t, J = 2.0Hz), 10.43(1 H, s), 10.49(1 H, s 1-574 'H-NMRCCDCIs) δ 7.31(1H, d, J = 2.9Hz), 7.41(1H, d, J = Z.9Hz), 7.50-7.6K4H, m), 7.65(1H, broad- s), 7.74(1H, df J = 7.8Hz), 7.81 (1H, d5 J = 2.0Hz), 7.88-7.9K2H, m), 8.01-8.05(3H, m), 8.23(1H, broad - s) 1-575 'H-NMR(DMS〇-d6) δ 2.30(3H, s), 3.56(3H, s), 6.32(1 H, septet, J=5.9Hz), 6.85(1H, s), 7.19 -7.43(8H, m), 7.58(1Ht broad-s), 7.70 (1H, d, J = 7.8 Hz). 1-576 'H-NMRC DMSO-dg) δ 2.35 (3H, s), 7.05 (1 H, d, J = 2.4 Hz), 7.33 (1H, d, J = 2.4 Hz), 7.48-7.59 (4H?m), 7.67(1H, broad-s), 7.72(1H, d, ϋ = 7.8HzX 7.88-7.90C2H, m), 7.99-8.03(2H, m), 8.17(1H, broad-s) , 8.24(1 H, broad-s), 8.28(1 H, t, J = 1.0Hz). 1-577 lH-NMR(DMS〇-d6) δ 2.40(3H, s), 7.11(1H, d, ϋ = 2.5Hz), 7.20-7.25(1H, m)f 7.3〇-7.37(2H, m)5 7.53-7.5B(2H, m), 7.60(1H, s), 7.76 (1H, d, J = 7.8 Hz), 7.97-8.00(2H, m), 8.17-8.Z2(1H, m), B.29(2H, d, J = 8.8HzX 8.61, 8.65(1H, two broad-s). 1- 578 'H-NMRC DMSO-dg) δ 2.37(3H? s), 7.01 (2H, t, J = 8.3Hz), 7.09 (1H, d, J = 2.5Hz), 7.35(1H, d, J = 2.5Hz ), 7.42-7.46(1H, m)? 7.53 (1Ή, t, J = 8.3Hz), 7.65(1H, s), 7.76(1H, d, J = 7.8Hz), 7.92-8.00 (3H, m) , 8.23(1 H, s), 8.29(1 H, s). 1-579 lH-NMR(DMS〇-d6) δ 2.39(3H, s), 7.11(1 H, d, J = .2.4Hz) , 7.36 (1H, d, ϋ = 2.4Hz), 7.42-7.44(1H, m), 7.57(1H? t J = 7.8Hz), 7.63 (1H, s), 7.78C1H, d, J = 7.8Hz) , 7.95(1H, d, ϋ = 8.3Ης), 7.99(1Ht d, J = 2.0Hz), 8.21-8.25(2H, m), 8.29(1H, s ), 8.4K1H, s), 8.54-8.55 (1H, m). 1-580 lH-NMR (CDCi3) δ 3.560H, s), 7.13 (1 H, dd, J = 9.3, 2.4 Hz), 7.19- 7·23(2Η,m), ?JZ7-7.34(5H, m)t 7·39(1Η, d, J = 8·3Ηζ), 7.6K1H,t, J = 1.5Hz), 7.65(1 H, d, J = 8.3 Hz), 7.78 (1 H, d} J = 2.4 Hz) f 7.98 (1H, d, J = ZAHzl 8.13 (1H broad-s), 8.55 (1 H d, J = 9.3 Hz). 129 200836629 Table 5 (21)
ΊΙΜί編號—— 一物性値 5 1-581 1 H-NMR(CDCi3) δ 7.12~7.18(2H, m), 7.36-7.53(6H, m), 7.63(1Η, d, J = 2.0Hz), 7.68(1H, d, J = 7.8Hz), 7.75(1K, s), 7.82(2H, d, J = 7.8Hz), 8.02-8.05(1 H, m), 8.21 (1H, s), 8.31 (1H, s), 8.53(1 H, s). 1-582 H-NMR(CDCi3) δ 7.13-7.18(2Ht m), 7.31 (1H, dd, J = 4.9, ?.8Hz), 7.45-7.53(3H, m), 7.7〇-7.73(2H, m), 7.84(1H, d, J = 1.5HzX 7.90 :1H, dd, J = 1.5f7.8Hz), 8.04(1H, dd J = 2.0, 7.8Hz), 8.20(1H, s), 8.33(1 H, s), 8.42(1 H, dd, J = 2.0, 4.9Hz), 8.83(1 H, s). 1-583 lH-NMR(CDCi3) δ 7.49-7.60(4H, m), 7.76(1 H, d? J = 7.8Hz), 7.83 (1H, d, J = 2·4Ηζ), 7.88-8.03C7H, m), 8.08(1H, s), 8.18(1H,s), 8.29 (1H, t, J = 2.0Hz). 1-584 'H-NMRCDMSO-dg) $ 3.45(3H, s), 7.24-7.32(5H, m), 7.45-7.47 (2H, m)T 7.77-7.80(2H, m), 7.92(1H, s), 8.22(2H, s), 10.49(1 H, broad). 1-585 ''H-NMRCGDClg) <5 3.48(3H, broad-s), 6.80( 1H, broad), 7.01 (1H, broad), 7.1K1H, s), ?.14(1H, broad), 7.21-?.30(3H, broad-m), 7.78(4H, broad), 8.38(1H, 1-586 ;H-NMR(CDCi3) δ 3.52(3H, s), 7.09(1 H, dd, J = 4.9, 7.3Hz), 7.13 (1H, s), 7.34-7.36C2H, m), 7.53(1 HT dd, J = 1.5, 7.8Hz), 7.77^7.82 (4H, m), 8.21 (1H, dd, J = 2.0, 4.9Hz)? 8.41 (1H, s). 1-587 'H-NMRCDMSO-de) δ 7.53-7.64(4H, m), 7.80(1 H, d, J = 7.8Hz), 7.92(1 H, s)f 7.99-8.02(2H, m), 8.07-8.09(1 H( m), 8.23(2H, s), 8.40 (1H, s), 10.50(1H, s), 10.57C1H s). 1-588 lH"*NMR(DMS〇-d6) δ 7.33-7.40(2H, m), 7.54-7.63(2H, mX 7.68-7.72(1 H, m), 7.80(1 HT d, J = 7.8Hz), 7.92(1 H, s), 7.99(1 H, dt J = 7.8Hz), 8.23(2H, s), 8.35(1 H, s), 10.05(1 H, broad), 10.66 (1H s). ^ 1-589 'H-NMRCDMSO-da) δ 7.56-7.60(2H, m), 7.82(1H} d, J = 7.8Hz), 7.92-7.97(2H, m), 8.12(1 H, dd, J = 2.0, 7:8Hz), 8.23(2H, s), 8.33 (\H, d, J = 2.0Hz), 8.55(1H, dd, J = 2.Q, 4.9Hz), 10.55(1H, broad), 10.90(1 H, s). 1-590 ^H-NMRCDMSO-dg) δ 7.36-7.42(2H, m), 7.57(1H, t, J = 7.8Hz), 7.80(1 H, d, J = 7.8Hz), 7.92(1 H} s), 8.06-8.11(3H, m), B.23(2H, s), 8.38(1H? s), 10.50(1H, s), 10.56(1H, s).ΊΙΜί number - one physical property 値5 1-581 1 H-NMR (CDCi3) δ 7.12~7.18(2H, m), 7.36-7.53(6H, m), 7.63(1Η, d, J = 2.0Hz), 7.68 (1H, d, J = 7.8Hz), 7.75(1K, s), 7.82(2H, d, J = 7.8Hz), 8.02-8.05(1 H, m), 8.21 (1H, s), 8.31 (1H , s), 8.53 (1 H, s). 1-582 H-NMR (CDCi3) δ 7.13-7.18(2Ht m), 7.31 (1H, dd, J = 4.9, ?.8Hz), 7.45-7.53 (3H , m), 7.7〇-7.73(2H, m), 7.84(1H, d, J = 1.5HzX 7.90 :1H, dd, J = 1.5f7.8Hz), 8.04(1H, dd J = 2.0, 7.8Hz) , 8.20(1H, s), 8.33(1 H, s), 8.42(1 H, dd, J = 2.0, 4.9Hz), 8.83(1 H, s). 1-583 lH-NMR(CDCi3) δ 7.49 -7.60(4H, m), 7.76(1 H, d? J = 7.8Hz), 7.83 (1H, d, J = 2·4Ηζ), 7.88-8.03C7H, m), 8.08(1H, s), 8.18 (1H, s), 8.29 (1H, t, J = 2.0Hz). 1-584 'H-NMRCDMSO-dg) $ 3.45(3H, s), 7.24-7.32(5H, m), 7.45-7.47 (2H m)T 7.77-7.80(2H, m), 7.92(1H, s), 8.22(2H, s), 10.49(1 H, broad). 1-585 ''H-NMRCGDClg) <5 3.48(3H , broad-s), 6.80( 1H, broad), 7.01 (1H, broad), 7.1K1H, s), ?.14(1H, broad), 7.21-?.30(3H, broad-m), 7.78( 4H, broad), 8.38 (1H, 1-586; H-NMR (CDCi3) 3.52(3H, s), 7.09(1 H, dd, J = 4.9, 7.3Hz), 7.13 (1H, s), 7.34-7.36C2H, m), 7.53 (1 HT dd, J = 1.5, 7.8Hz) , 7.77^7.82 (4H, m), 8.21 (1H, dd, J = 2.0, 4.9Hz)? 8.41 (1H, s). 1-587 'H-NMRCDMSO-de) δ 7.53-7.64(4H, m) , 7.80(1 H, d, J = 7.8Hz), 7.92(1 H, s)f 7.99-8.02(2H, m), 8.07-8.09(1 H( m), 8.23(2H, s), 8.40 ( 1H, s), 10.50(1H, s), 10.57C1H s). 1-588 lH"*NMR(DMS〇-d6) δ 7.33-7.40(2H, m), 7.54-7.63(2H, mX 7.68-7.72 (1 H, m), 7.80 (1 HT d, J = 7.8 Hz), 7.92 (1 H, s), 7.99 (1 H, dt J = 7.8 Hz), 8.23 (2H, s), 8.35 (1 H , s), 10.05 (1 H, broad), 10.66 (1H s). ^ 1-589 'H-NMRC DMSO-da) δ 7.56-7.60(2H, m), 7.82(1H} d, J = 7.8Hz) , 7.92-7.97(2H, m), 8.12(1 H, dd, J = 2.0, 7:8Hz), 8.23(2H, s), 8.33 (\H, d, J = 2.0Hz), 8.55(1H, Dd, J = 2.Q, 4.9 Hz), 10.55 (1H, broad), 10.90 (1 H, s). 1-590 ^H-NMRCDMSO-dg) δ 7.36-7.42 (2H, m), 7.57 (1H , t, J = 7.8Hz), 7.80(1 H, d, J = 7.8Hz), 7.92(1 H} s), 8.06-8.11(3H, m), B.23(2H, s), 8.38( 1H? s), 10.50 (1H, s), 10.56 (1H, s).
130 200836629 表 5(22)130 200836629 Table 5 (22)
—化合物編號:: 物性偃 1 1-591 · H-NMR(CDCI3) δ 3.560Η, s), 7.12(1Hf s), 7.20~7.33(6H, m), ?.40(1H, t J = 7.8Hz), 7.55(1H, s), 7.62(2H, s), 7.64(1H, d, J = l.OHz), 7.72(1H d, J = 7.8Hz). ϊ 1-592 H-iSiMR(DMS〇-d6) 5 2.Z3(3H, s), 5.64(2H, s), 7.15(1H, s), 7.42 ;1Ht d, J = 1.5Hz), 7.50-7.63(4H, m), 7.68(1H, s), 7.75(1H, d, J = 7.8Hz), 7.98-8.01 (2Hf m), 8.03-8.06(1 H, m), 8.35(1 H, s), 10.08 :1H, s), 10.46(1H, s). 1-593 H-NMR(GDCl3) d 2.30(3H, s), 5.33(2H, s), 6.94(1 H, s), 7.12 (1H, s), 7.15-7.2K1H, m), 7.28-7.33(1H, mX 7.36(1H, d, J = 2.0Hz), 7.44-7.54(2H, m), 7.72(1H, d, J = 7.8Hz), ?.86(1H, s), 7.90(1H, dd, J = 1.5, 7.8Hz), 8.1〇-8.15(lH, m), 8.25(1H, s)f 8.64(1H, d? J = 15.6Hz). 1-594 'H~NiVlR(CDCi3) (5 2.24C3H, s), 5.39(2H, s), 6.94(1 H, s), 7.09 (IH, s), 7.28(1 K dd, J = 4.9, 7.3Hz), 7.33(1 H, d, J = 1.5Hz)t 7.42 (1K t J = 7.8Hz), 7.67(1H, d,J = 7.8Hz),7·83(1Η, d J = 7·8Ηζ), 7.92(1H, s), 7.99(1H, dd, J = 2.0, 7.3Hz), δ.ίδ(1Η, s), 8.40(1H, dd, J = 2.0, 4.9Hz), 8.85(1 H, s). 1-595 'H-NMRiGDOis) δ 2.21 (3H, sX 3.5QOH, s), 5.39(2H, s), 6.94(1^., s), 7.10(1H? s), 7.13-7.19(2H, m), 7.21-7.27(4^ m), 7.32(1H, t, J = 7.8Hz), 7.35(1H, d, J = 1.5Hz), 7.63(1H, s), 7.70(1H, d, J = 7.8Hz), 7.76(1H, s). 1-596 ^-NMRCDMSO-da) δ 2.06(2H, quint, J = 7.3Hz)t 2.87(2HS t, ϋ = 7.3Hz), 3.12-3.14(2H, m), 7.52-7.63(5H, m), 7.75(1 H, d, J = 7.8Hz), 7.99-8.01 (2H? m), 8.07(1 H, d, J = 7.8Hz), 8.37(1 H, s), 10.33(1 H, s), 10.49C1K s). 1-597 lH-NMR(DMS〇-d6) δ 2.06(2Ht quint, ϋ = 7.3Hz), 2.87(2H, % ύ = 7.3Hz), 3·13(2Η dd, J = 7.3, 12.2Hz), 7·33-7.40(2Η, m),7-52-7.63 (3Ht m), 7.67-7.72(1 H, m), 7.75(1 H, d, J = 7.8Hz)? 7.97(1 H, d, ϋ = 7.8Hz), 8.33(1H, s), 10.35(1H, s), 10.66(1H, s). 1-5B8 i H-NMR(DMS〇-ci6) d 2.07(2H, quint J = 7.3Hz), 2.87(2H} = 7.3Hz), 3.15(2H, dd, J = 7.3, 1Z.2Hz), 7.45(1 HT s), 7.52-7.64(4H, m), 7.75(1H, d, J = B.3Hz), 7.98-δ.01(2Η, m), 8.06(1H, dd, J = 1.5, 7.8Hz), 8.37(1H, t J = 1.5Hz), 10.34(1H, s), 10.49(1H, s). 1-599 lH-NMR(DMS〇-d6) δ 2.07(2H, quint, ϋ = 7.3Hz), Z.87(2H, t vi = 7.3Hz), 3.15(2H dd, J = 7.3, 12.2Hz), 7.33-7.40(2H, m), 7.45(1 H, s), 7.52-7.63(2H, mX 7.67-7.76(2HT m), 7.98(1 H, d, J = 7.8Hz), 8.33 (1K s), 10.37(1H, s), 10.66(1H? s). 1-600 lH-NMR(CDCi3) ¢2.35 (3H, s), 7.12-7.16 (2H, m), 7.50-7.65 (5H, m), 7.72 (1Hf dd, J =1.5, 7.8Hz), 8.01 (2H, d, J =8,3Hz), 8.24 (1H, s), |10.2(1H, brs), 10.3 C1H, brs). 131 200836629 表 5(23)- Compound No.:: Physical Properties 1-1 1-591 · H-NMR (CDCI3) δ 3.560Η, s), 7.12(1Hf s), 7.20~7.33(6H, m), ?.40(1H, t J = 7.8 Hz), 7.55(1H, s), 7.62(2H, s), 7.64(1H, d, J = l.OHz), 7.72(1H d, J = 7.8Hz). ϊ 1-592 H-iSiMR(DMS 〇-d6) 5 2.Z3(3H, s), 5.64(2H, s), 7.15(1H, s), 7.42;1Ht d, J = 1.5Hz), 7.50-7.63(4H, m), 7.68( 1H, s), 7.75(1H, d, J = 7.8Hz), 7.98-8.01 (2Hf m), 8.03-8.06(1 H, m), 8.35(1 H, s), 10.08 :1H, s), 10.46(1H, s). 1-593 H-NMR(GDCl3) d 2.30(3H, s), 5.33(2H, s), 6.94(1 H, s), 7.12 (1H, s), 7.15-7.2K1H , m), 7.28-7.33 (1H, mX 7.36 (1H, d, J = 2.0Hz), 7.44-7.54(2H, m), 7.72(1H, d, J = 7.8Hz), ?.86(1H, s), 7.90(1H, dd, J = 1.5, 7.8Hz), 8.1〇-8.15(lH, m), 8.25(1H, s)f 8.64(1H, d? J = 15.6Hz). 1-594 ' H~NiVlR(CDCi3) (5 2.24C3H, s), 5.39(2H, s), 6.94(1 H, s), 7.09 (IH, s), 7.28 (1 K dd, J = 4.9, 7.3 Hz), 7.33 (1 H, d, J = 1.5 Hz) t 7.42 (1K t J = 7.8 Hz), 7.67 (1H, d, J = 7.8 Hz), 7·83 (1Η, d J = 7.8 Ηζ), 7.92 (1H, s), 7.99(1H, dd, J = 2.0, 7.3Hz), δ.ίδ(1Η, s), 8.40(1H, dd, J = 2.0, 4.9 Hz), 8.85 (1 H, s). 1-595 'H-NMRiGDOis) δ 2.21 (3H, sX 3.5QOH, s), 5.39(2H, s), 6.94(1^., s), 7.10(1H? s), 7.13-7.19(2H, m), 7.21-7.27(4^m), 7.32(1H, t, J = 7.8Hz), 7.35(1H, d, J = 1.5Hz), 7.63 (1H, s), 7.70(1H, d, J = 7.8Hz), 7.76(1H, s). 1-596^-NMRCDMSO-da) δ 2.06(2H, quint, J = 7.3Hz)t 2.87(2HS t, ϋ = 7.3Hz), 3.12-3.14(2H, m), 7.52-7.63(5H, m), 7.75(1 H, d, J = 7.8Hz), 7.99-8.01 (2H? m), 8.07( 1 H, d, J = 7.8 Hz), 8.37 (1 H, s), 10.33 (1 H, s), 10.49C1K s). 1-597 lH-NMR (DMS〇-d6) δ 2.06 (2Ht quint, ϋ = 7.3Hz), 2.87(2H, % ύ = 7.3Hz), 3·13(2Η dd, J = 7.3, 12.2Hz), 7·33-7.40(2Η, m), 7-52-7.63 (3Ht m), 7.67-7.72(1 H, m), 7.75(1 H, d, J = 7.8Hz)? 7.97(1 H, d, ϋ = 7.8Hz), 8.33(1H, s), 10.35(1H, s), 10.66(1H, s). 1-5B8 i H-NMR(DMS〇-ci6) d 2.07(2H, quint J = 7.3Hz), 2.87(2H} = 7.3Hz), 3.15(2H, dd, J = 7.3, 1Z.2Hz), 7.45(1 HT s), 7.52-7.64(4H, m), 7.75(1H, d, J = B.3Hz), 7.98-δ.01(2Η, m), 8.06 (1H, dd, J = 1.5, 7.8 Hz), 8.37 (1H, t J = 1.5 Hz), 10.34 (1H, s), 10.49 (1H, s). 1-599 lH-NMR (DMS〇-d6) δ 2.07 (2H, quint, ϋ = 7.3 Hz), Z.87 (2H, t vi = 7.3 Hz), 3.15 (2H dd, J = 7.3, 12.2 Hz) , 7.33-7.40(2H, m), 7.45(1 H, s), 7.52-7.63(2H, mX 7.67-7.76(2HT m), 7.98(1 H, d, J = 7.8Hz), 8.33 (1K s ), 10.37(1H, s), 10.66(1H?s). 1-600 lH-NMR(CDCi3) ¢2.35 (3H, s), 7.12-7.16 (2H, m), 7.50-7.65 (5H, m) , 7.72 (1Hf dd, J = 1.5, 7.8Hz), 8.01 (2H, d, J = 8, 3Hz), 8.24 (1H, s), |10.2(1H, brs), 10.3 C1H, brs). 131 200836629 Table 5 (23)
:化合物Μ號― 物麵 1 1-601 1 H-NMR( DMSO-d6) δ 2.37(3H,s),7.29-8.01 (10H,m)f 、 0.3(1 H,s)T10.6(1 H,s). 1 1-602 1 ( H-NMR(DMSO-d6) ά 7.47-7.65(5H, m), 7.75(1 H, dd, J = 1.5, .BHz), 7.93(1 H, d, J = 7.8Hz), 8.01-δ.04(2Η, m), 8.12(1 H, s), 8.17 1H, d, J = 8.8Hz), 10.17C1H s), 10.7K1K s). i 1-603 ^ ( H-NMR(CDCl3) d 3.22(3H, s), 3.42(3H, s), 7.17-7.23(1H, m), 7.29-^.35(2H, m), ?.49-7.57(2H, m)t 7.64(1H, d, J = B.SHz), 7.B1-7.83 1H, m), 8.0〇-8.10(2H, m), 8.14-8.18(1H, m), 8.41(1H, s), 8.62(1H, i, J = 15.1 Hz). ] 1-604 H-NMR(CDCt3) δ 1.09(3Ht t, J = 7.3Hz), 1.5K9H, s), 1.84-1.93 2H, m), 4.38(2H, t, J = 6.8HzX 6.34(1 H, d, J = 8.3Hz), 6.95(1 H, d, J = 8.3HzX 7.09ClH, d, J = 7.8Hz), 7.18(1H, d, J = 8.3Hz), 7.48-7.72(7H, m), 7.79-7.81 (2H, m). 1-605 H-NMR(DMS〇-d6) δ 7.51-7.63(5H, m), 7.79(1H, d, J = 7.8Hz), 7.83-7.86(2Ht m), 7.99-8.02(2H, m), 8.07(1 H, dd, J = 1.0, 8.3Hz), 8.38(1H, s), 10.48C1H, sX 10.63(1H, s). 1-96 ]H-NMR(DMS〇-d6) δ 7.54-7.59(2H, m), 7.80(1H, d, J = 7.8Hz), 7.S3(1HT dd, J = 1.0, 7.8Hz), 8.06-8.11(2H, m), 8.29-8.3K2H, m), 8.54(1 H, dd, J = 2.0, 4.9Hz), 10.68(1 H, s), 10.88(1 H, s). 2-1 'H-NMR (DMS〇-d6) δ 6.15 (1H, dddd, J =42.0, 11.6, 11.6, 5.6Hz), 7.47-7.59 (4H, m), 7.62 (2H, s), 7.78 (1H, d, J =7.2Hz), 8.01 (2H, d, J =7.2Hz)i 8.11 (1H, s), 8.38 (1H, s), 10.35 (1H, sX 10.40 (1H, s). 2-159 'H-NMR (DMSO~d6) δ 3.53 (3H, s), 5.80 (1H, brdd, J =42.4, 5.6Hz), 7.21-7.49 (7H, m), 7.55 (2H, s), 7.84 (2H, brs), 10.18 (1H s)· 2-160 'H-NMR (CDCi3) δ 3.53 (3H, brs), 5.02 (1H, dddd, J =44.0, 10.8, 10.8, 5.2Hz), 6.83 (1H, brs)t 7.07 (1H, brs), 7.16-7.38 (5H, m), 7.52 (2H s), 7.61 (1Ht brs), 7.73 (1H, brs). 2-163 'H-NMR (GDCIg) δ 3.57 (3H, s), 5.02 (ΊΗ, brdd, J =44.0, 5.6Hz), 7.11-7.14 (1H, m), 7.39 (2H, brs), 7.49-7.59 (4Hf m), 7.73 (2H, brs), 8.26 (1H, brs). 2-166 iH-NMR (0DG13) δ 3.31 (3H, s),4.97 (1Ht dddd, J =440, 112, 11.2, 5.2Hz), 7.15-7.18 (2H, m), 7.40 (2H, s), 7.45-7.57 (3H, m)T 7.70 (1H, sX 7.76 (1H, ddd, J =7.2, 2.0, 2.0Hz), 7.82-7.92 (3H, m). 2-167 ^-NMR (CDCI3) δ 3.33 (3Ht s), 4.96 (1H, dddd, J =44.0, 11.2, 11.2, 6.0Hz), 7.18-7.21 (3H, m), 7.31-7.33 (1H, m), 7.40 (2H, s), 7.52-7.56 (1H, m), 7.71 (1H, brs), 7.74-7.76 (1H, m), 8,11-8.16 (1H, m), 8.40 (1H, brs). 2-170 lH-NMR(CDCI3) δ 3.31 (3H, s), 4.96 (1H, dddd, J =44.0, 11.2, 11.2, 6.0Hz), 7.21-7.28 (2H, m), 7.38-7.41 (3H, m), 7.69 (2H, brs)T 8.14 (1H dd, J =8.0, 2.0Hz), 8.26 (1H, s), 8.52 (1H, t J =2OHz). 2-173 'H-NMRCGDCls) δ 3.19 (3H, s), 4.97 (1H, dddd, J =43.9, 10.7, 10:7, 5.7Hz), 7.16-7.20 (2H, m), 7.39 (2H, s), 7.47-7.51 ClHt m), 7.67 (1K s),7.72-7.75 (2H, m), 7.85 (1H, ddt J =7.8, 1,5Hz), 8.49 (1H s). 2-174 •H-NMR (CDCI3) 6 3.30 (3H, s), 3.35 (3Hf s), 5.00 (1H, brdd, J =44.0, 5.2Hz), 6.81 (1H, d, J =7.2Hz), 6.97 (1H, t, J =8.0Hz)t 7.09-7.24 (6H, m), 7.36-7.39 (3H, m). 132 200836629 表5(2磡: Compound No. - No. 1 1-601 1 H-NMR (DMSO-d6) δ 2.37 (3H, s), 7.29-8.01 (10H, m)f, 0.3 (1 H, s) T10.6 (1 H, s). 1 1-602 1 (H-NMR (DMSO-d6) ά 7.47-7.65 (5H, m), 7.75 (1 H, dd, J = 1.5, .BHz), 7.93 (1 H, d , J = 7.8Hz), 8.01-δ.04(2Η, m), 8.12(1 H, s), 8.17 1H, d, J = 8.8Hz), 10.17C1H s), 10.7K1K s). i 1- 603 ^ (H-NMR(CDCl3) d 3.22(3H, s), 3.42(3H, s), 7.17-7.23(1H, m), 7.29-^.35(2H, m), ?.49-7.57 ( 2H, m)t 7.64(1H, d, J = B.SHz), 7.B1-7.83 1H, m), 8.0〇-8.10(2H, m), 8.14-8.18(1H, m), 8.41(1H , s), 8.62 (1H, i, J = 15.1 Hz). ] 1-604 H-NMR (CDCt3) δ 1.09 (3Ht t, J = 7.3 Hz), 1.5K9H, s), 1.84-1.93 2H, m ), 4.38(2H, t, J = 6.8HzX 6.34(1 H, d, J = 8.3Hz), 6.95(1 H, d, J = 8.3HzX 7.09ClH, d, J = 7.8Hz), 7.18(1H , d, J = 8.3 Hz), 7.48-7.72 (7H, m), 7.79-7.81 (2H, m). 1-605 H-NMR (DMS 〇-d6) δ 7.51-7.63 (5H, m), 7.79 (1H, d, J = 7.8Hz), 7.83-7.86(2Ht m), 7.99-8.02(2H, m), 8.07(1 H, dd, J = 1.0, 8.3Hz), 8.38(1H, s), 10.48C1H, sX 10.63(1H, s). 1-96 ]H-NMR(DMS〇-d6) δ 7.54-7.59(2H, m), 7.80(1H, d, J = 7.8Hz), 7.S3(1HT dd, J = 1.0, 7.8Hz), 8.06-8.11(2H, m), 8.29-8.3K2H, m), 8.54(1 H, dd, J = 2.0, 4.9Hz ), 10.68(1 H, s), 10.88(1 H, s). 2-1 'H-NMR (DMS〇-d6) δ 6.15 (1H, dddd, J = 42.0, 11.6, 11.6, 5.6Hz), 7.47-7.59 (4H, m), 7.62 (2H, s), 7.78 (1H, d, J = 7.2Hz), 8.01 (2H, d, J = 7.2Hz)i 8.11 (1H, s), 8.38 (1H , s), 10.35 (1H, sX 10.40 (1H, s). 2-159 'H-NMR (DMSO~d6) δ 3.53 (3H, s), 5.80 (1H, brdd, J = 42.4, 5.6 Hz), 7.21-7.49 (7H, m), 7.55 (2H, s), 7.84 (2H, brs), 10.18 (1H s)· 2-160 'H-NMR (CDCi3) δ 3.53 (3H, brs), 5.02 (1H , dddd, J = 44.0, 10.8, 10.8, 5.2Hz), 6.83 (1H, brs)t 7.07 (1H, brs), 7.16-7.38 (5H, m), 7.52 (2H s), 7.61 (1Ht brs), 7.73 (1H, brs). 2-163 'H-NMR (GDCIg) δ 3.57 (3H, s), 5.02 (ΊΗ, brdd, J = 44.0, 5.6 Hz), 7.11-7.14 (1H, m), 7.39 ( 2H, brs), 7.49-7.59 (4Hf m), 7.73 (2H, brs), 8.26 (1H, brs). 2-166 iH-NMR (0DG13) δ 3.31 (3H, s), 4.97 (1Ht dddd, J =440, 112, 11.2, 5.2 Hz), 7.15-7.18 (2H, m), 7.40 (2H, s), 7.45-7.57 (3H, m)T 7.70 (1H, sX 7.76 (1H, ddd, J = 7.2 , 2. 0, 2.0 Hz), 7.82-7.92 (3H, m). 2-167 ^-NMR (CDCI3) δ 3.33 (3Ht s), 4.96 (1H, dddd, J = 44.0, 11.2, 11.2, 6.0Hz), 7.18 -7.21 (3H, m), 7.31-7.33 (1H, m), 7.40 (2H, s), 7.52-7.56 (1H, m), 7.71 (1H, brs), 7.74-7.76 (1H, m), 8 ,11-8.16 (1H, m), 8.40 (1H, brs). 2-170 lH-NMR (CDCI3) δ 3.31 (3H, s), 4.96 (1H, dddd, J = 44.0, 11.2, 11.2, 6.0Hz ), 7.21-7.28 (2H, m), 7.38-7.41 (3H, m), 7.69 (2H, brs)T 8.14 (1H dd, J = 8.0, 2.0Hz), 8.26 (1H, s), 8.52 (1H , t J = 2OHz). 2-173 'H-NMRCGDCls) δ 3.19 (3H, s), 4.97 (1H, dddd, J = 43.9, 10.7, 10:7, 5.7Hz), 7.16-7.20 (2H, m ), 7.39 (2H, s), 7.47-7.51 ClHt m), 7.67 (1K s), 7.72-7.75 (2H, m), 7.85 (1H, ddt J = 7.8, 1,5Hz), 8.49 (1H s) 2-174 •H-NMR (CDCI3) 6 3.30 (3H, s), 3.35 (3Hf s), 5.00 (1H, brdd, J = 44.0, 5.2Hz), 6.81 (1H, d, J = 7.2Hz) , 6.97 (1H, t, J = 8.0Hz)t 7.09-7.24 (6H, m), 7.36-7.39 (3H, m). 132 200836629 Table 5 (2磡
一化合物編號 .性値 I 2-175 , H-UMR (CDCI3) δ 3.30 (3Η, s), 3.34 (3H, s), 5.00 (1H, dddd, J =44.0, 10.8, 10.8, 5.2Hz), 6.73-7.00 (4H, m), 7.15-7.26 (3H, m), ?.34 (1H, s), 7.38 (2H s). . 2-178 H-NMR (CDCl3) 5 3.29 (3H, s)r 3.37 (3H, s), 5.00 (1H, dddd, J =44.0, 10.8, 10.8, 5.2Hz), 7.02 (3H, brd, J =4.8Hz), 7.22 (1H, brd, J =4.8Hz), 7.33-7.40 (4H, m), 8.22 (1H, brs). 2-181 H-NMR (GDCI3) i 3.29 (3H, s), 3.37 (3H, s), 4.99 (1H, brdd, J =43.9, 5.4Hz),·6.99-7,07 (2Hf m), 7.23-7.26 (1H m)f 7.37-7.41 (1H, m), 7.38 (2H, s), 8.18 (1H, dt ϋ =2.4Hz), 8.26 (1H, d, J = . 2.4Hz). 2-182 Ή-NMR (CDCl3) δ 3.30 (3H, s), 3.41 (3H, s), 5.00 (1H, brdd, J =43.9, 17.9Hz), 6.89-6.91 (1H, m)( 7.08 (1H, ΐ, ϋ =7.8Hz)? 7.26-7.29 (1H, m), 7.43 (2H, s), 7.44 (1H, t, J =2.0Hz), 8.48 (2H, s), 9.02 (1H, s). . 2-183 'H-NMR (DlVlSO-de) 5 2.30 (3H, s), 6.47 (1H, brdd, J =41.0, 5.9Hz), 7.34 (1H, d, J =2.4Hz), 7.50-7.63 (5H, m), 7.77 (1H, d, J =7.8Hz), 7.94-8.01 (2H, m), 8.06 (1Ht dd, J =8.3, 1.5Hz), 8.37 t J =1.5Hz), 1G.14 (IK, s), 10.4B (1H, s). 2-184 'H-NMR (GDCi3) δ 3.55 (3H, s), 5.43 (1H, brdd, J =43.2, 5.6Hz), 7.18-7.37 (6H, m), 7.54-7.55 (2H, m), 7.78-7.82 (3H, m), 9.91 (1H, s). , 2-185 Ή-NMR (DMS〇-d6: CDCi3=1:1) δ 5.51 (1Ht brdd, J =43.0, 5.4Hz), 7.44-7.57 (5H, m), 7.76 (1K d, J =7.8Hz)t 7.80 (1H, d, J =2.4HzX 8.01-8.03 (2H, mX 8.20 (1H, d, J =8.3Hz), 8.30 (1H, s)t 9.97 (1H, s), 10.15 (1H,s). 2-186 Ή-NMR (CDC!3) δ 5.06 (1H, brdd, J =44.0, 5.9Hz), 7.44 (1H, dd, J =7.3, 4.9Hz), 7.55-7.59 (2H, m), 7.74-7.80 (3H, m), 7.94 (1H, d, J =7.8Hz), 8.22-8.24 (2H, m), 8.40 (1H, s), 8.54-8.57 (1H, m). 2-187 lH-NMR(CDGl3) 53.54 (3H, s), 5.47 (1H, brddd, J =5.9, 11.7, 42.9 Hz), 7.19-7.30 (4H, m), 7.31-7.36 (3Hf m), 7.82-7.84 (4H, m), 10.15 (1Hs). 2-188 'H-NMRCCDGls) (53.56 (3H, s), 5.01 (1H, brddd, J =5.4, 11.Z, 49.3Hz)T 7.13 (1H, d.d., J =4.9,7.3Hz), 7.41 (2H, s), 7.58 (1H, m), 7.72 (2H, (1H, d, J =2.5Hz)t 7.86 (ΊΗ, d, J =2.5Hz), 8.25 (1H d, J =2.9Hz), B.34 (1H, s).A compound number. 値I 2-175 , H-UMR (CDCI3) δ 3.30 (3Η, s), 3.34 (3H, s), 5.00 (1H, dddd, J = 44.0, 10.8, 10.8, 5.2Hz), 6.73-7.00 (4H, m), 7.15-7.26 (3H, m), ?.34 (1H, s), 7.38 (2H s). . 2-178 H-NMR (CDCl3) 5 3.29 (3H, s) r 3.37 (3H, s), 5.00 (1H, dddd, J = 44.0, 10.8, 10.8, 5.2Hz), 7.02 (3H, brd, J = 4.8Hz), 7.22 (1H, brd, J = 4.8Hz), 7.33-7.40 (4H, m), 8.22 (1H, brs). 2-181 H-NMR (GDCI3) i 3.29 (3H, s), 3.37 (3H, s), 4.99 (1H, brdd, J = 43.9, 5.4Hz),·6.99-7,07 (2Hf m), 7.23-7.26 (1H m)f 7.37-7.41 (1H, m), 7.38 (2H, s), 8.18 (1H, dt ϋ =2.4Hz), 8.26 (1H, d, J = . 2.4Hz). 2-182 Ή-NMR (CDCl3) δ 3.30 (3H, s), 3.41 (3H, s), 5.00 (1H, brdd, J = 43.9, 17.9Hz) , 6.89-6.91 (1H, m)( 7.08 (1H, ΐ, ϋ = 7.8Hz)? 7.26-7.29 (1H, m), 7.43 (2H, s), 7.44 (1H, t, J =2.0Hz), 8.48 (2H, s), 9.02 (1H, s). . 2-183 'H-NMR (DlVlSO-de) 5 2.30 (3H, s), 6.47 (1H, brdd, J = 41.0, 5.9Hz), 7.34 (1H, d, J = 2.4 Hz), 7.50-7.63 (5H, m), 7.77 (1H, d, J = 7.8 Hz), 7.94-8.01 (2H, m), 8.06 (1Ht dd, J = 8.3, 1.5Hz), 8.37 t J = 1.5 Hz), 1G.14 (IK, s), 10.4B (1H, s). 2-184 'H-NMR (GDCi3) δ 3.55 (3H, s), 5.43 (1H, brdd, J = 43.2, 5.6 Hz), 7.18-7.37 (6H, m), 7.54-7.55 (2H, m), 7.78-7.82 (3H, m), 9.91 (1H, s)., 2-185 Ή-NMR (DMS〇 -d6: CDCi3=1:1) δ 5.51 (1Ht brdd, J = 43.0, 5.4Hz), 7.44-7.57 (5H, m), 7.76 (1K d, J = 7.8Hz) t 7.80 (1H, d, J =2.4HzX 8.01-8.03 (2H, mX 8.20 (1H, d, J = 8.3Hz), 8.30 (1H, s)t 9.97 (1H, s), 10.15 (1H, s). 2-186 Ή-NMR ( CDC!3) δ 5.06 (1H, brdd, J = 44.0, 5.9Hz), 7.44 (1H, dd, J = 7.3, 4.9Hz), 7.55-7.59 (2H, m), 7.74-7.80 (3H, m) , 7.94 (1H, d, J = 7.8 Hz), 8.22-8.24 (2H, m), 8.40 (1H, s), 8.54-8.57 (1H, m). 2-187 lH-NMR(CDGl3) 53.54 (3H , s), 5.47 (1H, brddd, J = 5.9, 11.7, 42.9 Hz), 7.19-7.30 (4H, m), 7.31-7.36 (3Hf m), 7.82-7.84 (4H, m), 10.15 (1Hs) 2-188 'H-NMRCCDGls) (53.56 (3H, s), 5.01 (1H, brddd, J = 5.4, 11.Z, 49.3 Hz) T 7.13 (1H, dd, J = 4.9, 7.3 Hz), 7.41 (2H, s), 7.58 (1H, m), 7.72 (2H, (1H, d, J = 2.5Hz)t 7.86 (ΊΗ, d, J =2.5Hz), 8.25 (1H d, J =2.9Hz) , B.34 (1H, s).
133 200836629 表 5(25) — —化雜編號-- 物性値 T 2-189 ( Γ ( H-NMR (CDCI3> § 2.29 (6H, s), 4.95 (1H, brd, ϋ =44.0Hz), 6.86 1H, d, J =6.3HzX 6.96 (1H, s), 7.44-7.53 (3H, m), 7.57-7.61 (1K n), 7.63 (1H, brs), 7.71 (1H, d, J =8.3Hz), 7.86-7.90 (2H, m), 8.06 1H, dd, J =8.3, 1.5Hz), 8.12 (1H, brs), 8.32 (1H, t, J =1.5Hz) * I « 2-190 H-NMR CCDCI3) δ 2.20 (6H, s), 3.55 (3H, s), 5.00 (1H, brdd, J =43.9, 5.9Hz), 6.95 (2H, s), 7.10 (1H, dd, J =7.8, 4.9Hz), 7.35 2H, brd, J =4.4Hz)f 7.44 (1H, s), 7.55 (1H, dd, J =7.8, 1.5Hz), ?.68 (1H, brd, J =3.4Hz), 7.73 (1H, s)t 8.23 (1H, dd, J =4.9, LOHz). • 2-192 H-NMR (CDCi3) δ 2.31 (6H, s), 5.00 (1H, brddt J =43.9, 5.9Hz)f 6.99 (2H, s), 7.35 (1H, t, ϋ =8.3Hz), 7.47-7.63 (3H, m), 7.71 (1H, d, J =11.2Hz), 7.82 (1H, t, J =2.0Ηζ), 7.92 (2H, d, J =7.3Hz)t 8.08-8.14 (1K m), 8.58-8.63 (1H, m). 2-1.93 Ή-NMR (CDCi3) δ 2.32 (6H, s), 4.98-5.02 (1Ht m), 7Ό0 (2H, brs), 7.23-7.24 (1Ht m), 7.34-7.39 (2H, m), 7.56-7.60 (1H, m), 7.74 (1H, d, J =11.7HzX 7.85 (1H, ddd, J =9.3, 1.5, 1.5Hz), 8.22 (1H, ddd, J =7.8, 7.8, 2.0Hz), 8.67 (1H, ddd, J =8.3, 8.3, 2.0Hz), 8.80-8.90 (1K m). 2-194 Ή-NMR (CDCi3) δ Z31 (6H, s), 4.99 (1H, brdd, J =44.4, 5.9Hz), 6.99 (2H, brs)f 7.38 (1H, t ϋ =8.3Hz), 7.4δ (1H, ddf J =7.8, 4.9HzX 7.71 (1H, d? J =11.2Ηζλ 7.88 (1H, ddd, J =7.3, 7.3, 1.5Hz), 8.32 (1H, dd, J =7.8, 2.0Hz), 8.57 (1H, dd, J =4.9, 2.0Hz), 8.61 (1H, ddd, J =8.3, 8.3, 1.5Hz), 8.74 (1H, brs). 2-195 'H-NMRCDMSO-ds) δ 2.30(6H, s), 4.92-5.07(1H, m), 6.98(2H, s), 7.29-7.32(1 H, m), 7.53-7.57(3H, m), 7.60-7.64(1 H, mX 7.80-7.84 (1H, m), 7.89-7.9K2H, m), 8.20(!H, broad-s), 9.1〇-9.13(1H, m). 2-196 'H-NMRCDMSO-dB) δ 2.3K6H, s), 5.80-6.10(1H, m), 6.99(2H, s), 7.29-7.34(1 Hf m), 7.44-7.50(2H, m), 7.82-7.86(1 H, m), 8.27(1 H, dd, J = 7.3, 1.5Hz), B.57(1H ddT J = 4.9, 2.0Hz), 8.75C1H, broad-s), 9.68 (tH, dd, J = 6.8, 2.0Hz). 2-197 'H-NMR (DMSOd6) δ 6.59 (1H,brd, J =41·5Ηζ),7·53—7·63 (4H, m), 7.72-7.76 (1Ht m), 7.90 (1H, d, J =7.8Hz), 8.01-8.05 (3H, m), 8.10-8.13 (1H, m), 8.38 (1Ht d, J =8.8Hz), 8.45 (1Ht s), 9.08 (1H, t J =2.0HzX 10.50 (1H, s), 10.66 (tH, s). 2-198 'H-NMR(DMS〇-d6) δ 6.63 (1H, fardd, J =41.0, 6.3Hz), 7.34-7.40 (2H, m), 7.58-7.62 (2H, m), 7.70-7.76 (2H, m), 7.90 (1Ht d, J = 7.8Hz), 8.01 (1Ht d, J =7.BHz), B.08 (1Ht s), 8.37-8.40 (2H, m), 9.09 (IK dd, J =4.4, 1.5Hz), 10.69 (2H, s). 2-199 Ή-NMR (DMSO-d6) δ 6.63 (1H, brdd, J =41.0, 5.9Hz), 7.57-7.64 (2H, m), 7.75 (1H, dd, J =8.8, 3.9Hz), 7.93 (1H, d, J =7.8Hz), 7.98 (1H, dd, J =7.8, 1.5Hz), B.OB-8.13 (2Hf m), B.38-8.40 (2H, m), 8.56 (1H, dd, J =4.9, ZOHz), 9.08 (1H, dd, J =3.9, 1.5Hz), 10.71 (1H, s\ 10.91 (1H, s). 134 200836629 表5(爾133 200836629 Table 5(25) - Noisy number - Physical properties T 2-189 ( Γ ( H-NMR (CDCI3 > § 2.29 (6H, s), 4.95 (1H, brd, ϋ = 44.0Hz), 6.86 1H, d, J = 6.3HzX 6.96 (1H, s), 7.44-7.53 (3H, m), 7.57-7.61 (1K n), 7.63 (1H, brs), 7.71 (1H, d, J = 8.3Hz) , 7.86-7.90 (2H, m), 8.06 1H, dd, J = 8.3, 1.5Hz), 8.12 (1H, brs), 8.32 (1H, t, J = 1.5Hz) * I « 2-190 H-NMR CCDCI3) δ 2.20 (6H, s), 3.55 (3H, s), 5.00 (1H, brdd, J = 43.9, 5.9Hz), 6.95 (2H, s), 7.10 (1H, dd, J = 7.8, 4.9Hz ), 7.35 2H, brd, J = 4.4 Hz) f 7.44 (1H, s), 7.55 (1H, dd, J = 7.8, 1.5 Hz), ?.68 (1H, brd, J = 3.4 Hz), 7.73 ( 1H, s)t 8.23 (1H, dd, J = 4.9, LOHz). • 2-192 H-NMR (CDCi3) δ 2.31 (6H, s), 5.00 (1H, brddt J = 43.9, 5.9Hz)f 6.99 (2H, s), 7.35 (1H, t, ϋ = 8.3Hz), 7.47-7.63 (3H, m), 7.71 (1H, d, J = 11.2Hz), 7.82 (1H, t, J =2.0Ηζ) , 7.92 (2H, d, J = 7.3 Hz) t 8.08-8.14 (1K m), 8.58-8.63 (1H, m). 2-1.93 Ή-NMR (CDCi3) δ 2.32 (6H, s), 4.98-5.02 (1Ht m), 7Ό0 (2H, brs), 7.23-7.24 (1Ht m), 7.34-7.39 (2H, m), 7.56-7.60 (1H, m), 7.74 (1H, d, J =11.7HzX 7.85 (1H, ddd, J = 9.3, 1.5, 1.5Hz), 8.22 (1H, ddd, J = 7.8, 7.8, 2.0Hz), 8.67 (1H, ddd, J = 8.3, 8.3, 2.0Hz) , 8.80-8.90 (1K m). 2-194 Ή-NMR (CDCi3) δ Z31 (6H, s), 4.99 (1H, brdd, J = 44.4, 5.9Hz), 6.99 (2H, brs)f 7.38 (1H , t ϋ =8.3Hz), 7.4δ (1H, ddf J = 7.8, 4.9HzX 7.71 (1H, d? J = 11.2Ηζλ 7.88 (1H, ddd, J = 7.3, 7.3, 1.5Hz), 8.32 (1H, Dd, J = 7.8, 2.0 Hz), 8.57 (1H, dd, J = 4.9, 2.0 Hz), 8.61 (1H, ddd, J = 8.3, 8.3, 1.5 Hz), 8.74 (1H, brs). 2-195 'H-NMRC DMSO-ds) δ 2.30 (6H, s), 4.92-5.07 (1H, m), 6.98 (2H, s), 7.29-7.32 (1 H, m), 7.53-7.57 (3H, m), 7.60-7.64 (1 H, mX 7.80-7.84 (1H, m), 7.89-7.9K2H, m), 8.20 (!H, broad-s), 9.1〇-9.13(1H, m). 2-196 'H -NMRCDMSO-dB) δ 2.3K6H, s), 5.80-6.10(1H, m), 6.99(2H, s), 7.29-7.34(1 Hf m), 7.44-7.50(2H, m), 7.82-7.86 ( 1 H, m), 8.27 (1 H, dd, J = 7.3, 1.5 Hz), B.57 (1H ddT J = 4.9, 2.0 Hz), 8.75C1H, broad-s), 9.68 (tH, dd, J = 6.8, 2.0 Hz). 2-197 'H-NMR (DMSOd6) δ 6.59 (1H, brd, J = 41·5Ηζ), 7·53—7·63 (4H, m), 7.72-7.76 (1Ht m ), 7.90 (1H, d, J = 7.8 Hz), 8.01-8.05 (3H, m), 8.10-8.13 (1H, m), 8.38 (1Ht d, J = 8.8Hz), 8.45 (1Ht s), 9.08 (1H, t J =2.0HzX 10.50 (1H, s), 10.66 (tH, s). 2-198 'H-NMR (DMS〇-d6) δ 6.63 (1H, fardd, J = 41.0, 6.3 Hz), 7.34-7.40 (2H, m) , 7.58-7.62 (2H, m), 7.70-7.76 (2H, m), 7.90 (1Ht d, J = 7.8Hz), 8.01 (1Ht d, J =7.BHz), B.08 (1Ht s), 8.37-8.40 (2H, m), 9.09 (IK dd, J = 4.4, 1.5 Hz), 10.69 (2H, s). 2-199 Ή-NMR (DMSO-d6) δ 6.63 (1H, brdd, J = 41.0 , 5.9 Hz), 7.57-7.64 (2H, m), 7.75 (1H, dd, J = 8.8, 3.9 Hz), 7.93 (1H, d, J = 7.8 Hz), 7.98 (1H, dd, J = 7.8, 1.5Hz), B.OB-8.13 (2Hf m), B.38-8.40 (2H, m), 8.56 (1H, dd, J = 4.9, ZOHz), 9.08 (1H, dd, J = 3.9, 1.5Hz ), 10.71 (1H, s\ 10.91 (1H, s). 134 200836629 Table 5 (
物性値 l 2-200 ί ( W-NMR (DMS〇-d6) δ 3.46 (3H, s), 6.61 (1H, brdd, J =41.0, LlHz)t 7.25-7.48 (7H, m), 7.73 (1H, brdd, J =8.8, 3.9Hz), 7.83-^.88 (2H, m), 8.05 (1H, brs), 8.25 (1H, dd, J =8.8, 1.5Hz), 9.06 1H, dd, J =3.9, I.SHzl 10.58 (l.H, s). . 2-201 H-NMR (CDCl3) δ 6.07 (1H, dddd( J =53.2, 53.2, 2.9, 2.9Hz), 7.43-7.58 (6H, m), 7.79 (1H, d, J =7.8Hz), 8.00-8.02 (2H, m), 8.18 (1H, d;J =8.3Hz), 8.34 (1H, s), 9.61 (1H. s), 9.95 (1H, s). 2-202 H-NMR (CDCi3) δ 5.93 (1H, dddd, ϋ =53.2, 53.2, 2.9, 2.9Hz), 7.18-7.36 (3H, m), 7.50-7.57 (3H, m), 7.77 (1H, d, J =7.3Hz), 7.82 (1H, sX 7.92-7.94 (1H, m), 8.17 (1H, brd, J =1.5Hz), 8.31 (1H, s), 8.65 (1Hf brd, J=1.5Hz). 2-203 'H-NIVIR (CDCI3) $ 5.93 (1H, dddd, J =53.2, 53.2, 2.9, 2.9Hz), 7.38 (1H, dd, J =7.8, 4.9Hz), 7.49-7.53 (3H, m), 7.76 (1H, brd, J =7.8Hz), 7.89 (1H, s), 7.91 (1H, d, J =1.5Hz), 8.14 (1H, dd, J =7.8, 2.0Hz), 8.24 (1H s), 8-50 (1H, dcU =4.9, ZOHz), 8.61 (1H, s). 2-204 Ή-NMR (CDCi3) δ 5.06-5.20 (2H, m), 7.25 (1H, d, J =2.0Hz), 7.46-7.57 (5H, m), 7.71 (1H, d, J =7.8Hz), 7.96 (2H, dd, J =7.3, Ι.δΗζ), δ.1δ (1H, dd, J =7.8, 1.0Hz), 8.28 (1H, t J =2.0Hz), 8.72 (1H, s), 9.51 (1H, s). 2-205 lHHSIMR(CDGi3) δ 5.12-5.25 (2HT m), 7.21 (1H, ddd, J =11.7, 8.3, 1.0Hz), 7.27 (1H, s), 7.32 (1H, ddd, J =7.3, 7.3, 1.0Hz), 7.48-7.55 (3H, m), 7.76 (1H, d, J =7.8Hz), 8.03 (1H, ddd, J =7.8, 7.8, 2.0Hz), 8.11 (1H, d, J =8.3Hz), 8.20 (1H, brs)t 9.07 (1H, s), 9.19 (1H, d, J =1Q.7Hz). 2-206 ' H-NMR (GDGI3) δ 4.97-5.12 (2H, m)T 7.40 (1H, dd, J =7.8, 4.9Hz), 7·50-7.54 (2H,m),7:67-7.70 (2H,m),7.91 (1HT dd,J =8.3, 1.5Hz)t 8.15-8.20 (2H, m), 8.50-8.52 (2H, m). 2-207 'H-NMR (CDCi3: DMS0-d6=1:1) δ 5.51-5.67 (3H, m), 7.24 (2H, s)f 7.42-7.57 (3H, m), 7.66-7.69 (2Hf m), 8.00-8.02 (2H, m), 8.08 (1H, dd, J =8.3, 1.5Hz), 8.36 (1H, s), 8.61 (1H, brd, J =1l.2Hz), 10.19 (1H brs). 2-208 1 H-NMR (CDGi3:DMS〇-d6=1:1) δ 5.99-6.25 (3H, m), 7.23-7.33 (4H, m), 7.46 (1H, t, J =7.8Hz), 7.54-7.56 (1H, m), 7.68-7.72 (2H, m), 7.98-8.00 (1H, m), 8.29 (1H, s), 10.00 (1H, s), 10.46 (1H, s). 2-209 ' H—NMR (CD€!3: DMSO-d5=1:1) δ 6.00-6·25 (3H, m),7·29 (2H,s), 7.45-7.52 (2Ht m), 7.72 (IH, d, ϋ =?.8Ης), 7.96-8.02 (2H, m), 8.24 (1H, d, J =2.0Hz), 8.50 (1H} dd, J =4.9, 2.0Hz), 10.03 (1H, s), 10.75 (1H, s). 135 200836629 表 5{27) - … - …化雜編號 物性値 1 2-210 ( ( 4-NMR (CDCb) d 5.15-5.31 (1H, m), 7.41-7.57 (4H, m)5 7.79 1H, d, 7.92 (2H, s), 8.0U.04 (2H, brd, J 二7.3Hz), 8·18 1H, d, J =8.3Hz), 8.35 (1HT sX 9.85 (1H, s), 10.04 (1H, s). :\ 2-211 1 C H-NMR (CDCi3) ά 4.89-4.97 (1H, m), 7.1-8-7.26 (1H, m), 7.32-.3β (1H, m), 7.50-7.57 (2H? m), 7.76 (1H, d, J =7.8Hz), 7.89 (IH, i, J =1.5HzX 7.91 (2H, s), 8.02 (1H, s), 8.16 (1H, ddd, J =7.8, 7.8, LOHz), 8.32 (tH, t J =1-5Hz), 8.65 (1H, brd, J =16.1 Hz). 1 2-212 ^ i H-NMR (CDCI3) δ 4.96 (1H, brd, J =44.0Hz), 7.37 (1H., dd, J = A 4.9Hz), 7·52 (1H, brd, J 二 7.8Hz), 7.75 (1H, d,J 二 7·8Ηζ), 7·89 1H, d, J =8.3Ης), 7.90 (2H, s), δ.02 (1H, s), 8.12 (1H, dd, J =7.8, LOHz), 8·25 (1H, s), 8.佔(1H, dd, J =4.9,2.0H2:), 8·64 (1H, s). 2-213 H-NMR (CDCi3: DMSO-de (5:1)) δ 5.7δ (1H, brd, J =44.0Hz), 7.46-7.59 (5H, m), 7.79 (1H, t? J =2.0Hz), 7.90 (1H, t, J =2.0Hz), S-00 (1H, d, J =K5Hz), 8.03 (1H, s), 8.12 (1H, dd, J 二7.8, 1.5Hz), δ.39 (1H, t J =2.0Hz), 10.29 (1H, s)T 10.32 (1H, s). 馨 • 2-214 H-NMR (CDCb) <5 5.30-5.95 (1H, m), 7.19-7.24 (tH, m), 7.32-7.36 m), 7.51-7-59 (2H, m),7J6 (2H, d, J =2OHz), 7.88 UH, d, J =2.0Hz), 7.90-7.92 (2H, m), 8.18 (1H, ddd, J =7.¾ 7.8, 2.0Hz), 8.34 t J =2.〇Ηζλ 8.64 (1H, d, J =16.1 Hz). 2-215 1 H-NMR (CDCI3) δ 5.80-5.10 (1H, m)T 7.40 (t H, dd, J =7.8, 4.9Hz), 7.53 (1H, t, J =7.8Hz), 7.75-7.78 (2H, m), 7.87 (1H? d, J =2.0Hz), 7.88-7.91 (1H, m), 7.97 (1H, s), 8.16 (1H, dd, J =7.8, 2.0Hz)} 8.26 (1H, d, J =2.0Hz), 8.51 (IH, dd, J =4.4, 2.0Hz), 8.56 (1H, s). 2-216 !H-NMR (CDCI3) δ 3.55 (3HT s), 4.81-4.97 (1H, m), 7.19-7.33 (6H, m), 7.39 (1H? t, J =7.8HzX 7.50 (1H, s), 7.58-7.61 (1H, m), 7·70-7.74 (1H, m)T 7.74 (1H, d, J 二L5H£),7.85 (1H, d, J =1.5Hz). 2-217 'H-NMR (CDCi3) δ 3.53 (3H, brsX 4.74-4.98 (2HT m)T 6.84 (1H, brs), 7.08 (1H, brs), 7.17 (tH, dd, J =10r7T 8.3Hz), 7.39-7.47 (3H, m), 7.55-7.60 (2H, m), 7.74 (1H, d, J =2.0Hz), 7.86 (1H, d, J = 2.0Hz). 2-218 lH-NMR (CDCb)占 3.57 (3H,s),4-91 (1H,brd, J 二43.9Hz),7.13 (tH, dd, J -7.8, 4.9Hz), 7.39 (2H, d, J =4.4HzX 7.58 (2H, brs), 7.71-7.75 (3H, m), 7.88 (1H, brs), B.25 (1H, d, J =3.4Hz). 2-219 'H-NMR (CDCI3) 6 220 (6H, s)T 3.55 (3H, s)T 5.93 (1H, ddd, J =54.2, 2.9, 2.9HzX 6.96 (2HT s), 7.10 (1H, dd, J =7.3, 4.9Hz)T 7.35 (2H, d, J =4.4Hz), 7.46 (tHT s), 7.54 (1H, dd, J =7.8, 2.0Hz), 7.68 (1H, brd, J =3.9Hz), 7.73 (1H, s), 8.23 (1H, dd, J =4.4, 1.5Hz). 2-220 'H-NMR (CDCi3) 6 2.2B (6H, s), 5.00 (1H, brdd, J =43.9, 5.4Ης), 6.87 (1H, d, J =6.8Hz), 6.97 (1H, s), 7.41 (1H, dd, J =7.8T 4.9Hz)T 7.52 (tH, t, J =8.3Hz), 7.58 (tH, brs), 7.72-7.74 (1H, m), 7.83-7.86 (1HT mX 8.17 (1H, dd, J -7.8, 2.0Hz), 8.27 (1H, brs), 8.52 (2H, brs). 2-8 ^-NMR (DMSO-d6) δ 6.18 (1H? brdd, J =42.0, 5.2Hz)T 7.23-7.32 (2H, m), 7Λ7-7.55 (2H, m),7:62 (2H, s), 7J0 C1H,t J 二6.4Hz), 7.78 (1H, d, J =6.8HzX 8.03 (1H, d, J =7.6H2), 8.34 (tH, s), 10.38 (1H, s), 10.50 (1H, s). 4-1 'H-NIVIRCCDCis) 6 2.28(6H, s), T.30-TM(5H, m), 7.34(2H, s), 7.51-7.64(4H, m)T 7.75-7J8(2H, m).. 4-2 lH-NMR(CDCI3) δ 2.29(6H, s), 2.64(3H, s), 7.22-7.36(4H, ml 7.34C2H, s), 7.43-7.47(2H? m), 7.57-7.680H, m), 7.99(1 H, d, J = 7.3HzX 4-6 'H-NMRCCDCis) δ 2.29(6H, s), 7.32-7.39(6«, m), 7.58-7.66 (6H, m). 136 200836629 表 S(2S)Physical properties 値l 2-200 ί (W-NMR (DMS〇-d6) δ 3.46 (3H, s), 6.61 (1H, brdd, J = 41.0, LlHz)t 7.25-7.48 (7H, m), 7.73 (1H , brdd, J = 8.8, 3.9Hz), 7.83-^.88 (2H, m), 8.05 (1H, brs), 8.25 (1H, dd, J = 8.8, 1.5Hz), 9.06 1H, dd, J = 3.9, I.SHzl 10.58 (lH, s). 2-201 H-NMR (CDCl3) δ 6.07 (1H, dddd ( J = 53.2, 53.2, 2.9, 2.9 Hz), 7.43-7.58 (6H, m), 7.79 (1H, d, J = 7.8 Hz), 8.00-8.02 (2H, m), 8.18 (1H, d; J = 8.3 Hz), 8.34 (1H, s), 9.61 (1H. s), 9.95 (1H , s). 2-202 H-NMR (CDCi3) δ 5.93 (1H, dddd, ϋ = 53.2, 53.2, 2.9, 2.9 Hz), 7.18-7.36 (3H, m), 7.50-7.57 (3H, m), 7.77 (1H, d, J = 7.3 Hz), 7.82 (1H, sX 7.92-7.94 (1H, m), 8.17 (1H, brd, J = 1.5Hz), 8.31 (1H, s), 8.65 (1Hf brd, J=1.5Hz). 2-203 'H-NIVIR (CDCI3) $ 5.93 (1H, dddd, J = 53.2, 53.2, 2.9, 2.9Hz), 7.38 (1H, dd, J = 7.8, 4.9Hz), 7.49 -7.53 (3H, m), 7.76 (1H, brd, J = 7.8Hz), 7.89 (1H, s), 7.91 (1H, d, J = 1.5Hz), 8.14 (1H, dd, J =7.8, 2.0 Hz), 8.24 (1H s), 8-50 (1H, dcU = 4.9, ZOHz), 8.61 (1H, s). 2-204 Ή-NMR (CDCi3) δ 5.06-5.20 (2H, m), 7.25 ( 1H, d, J = 2.0 Hz), 7.46-7.57 (5H, m), 7.71 (1H, d, J = 7.8 Hz), 7.96 (2H, dd, J = 7.3, Ι.δΗζ), δ.1δ (1H, Dd, J = 7.8, 1.0 Hz), 8.28 (1H, t J = 2.0 Hz), 8.72 (1H, s), 9.51 (1H, s). 2-205 lHHSIMR(CDGi3) δ 5.12-5.25 (2HT m) , 7.21 (1H, ddd, J =11.7, 8.3, 1.0 Hz), 7.27 (1H, s), 7.32 (1H, ddd, J = 7.3, 7.3, 1.0 Hz), 7.48-7.55 (3H, m), 7.76 (1H, d, J = 7.8 Hz), 8.03 (1H, ddd, J = 7.8, 7.8, 2.0 Hz), 8.11 (1H, d, J = 8.3 Hz), 8.20 (1H, brs)t 9.07 (1H, s), 9.19 (1H, d, J = 1Q.7Hz). 2-206 'H-NMR (GDGI3) δ 4.97-5.12 (2H, m)T 7.40 (1H, dd, J = 7.8, 4.9Hz), 7·50-7.54 (2H, m), 7:67-7.70 (2H, m), 7.91 (1HT dd, J = 8.3, 1.5 Hz) t 8.15-8.20 (2H, m), 8.50-8.52 (2H, m). 2-207 'H-NMR (CDCi3: DMS0-d6=1:1) δ 5.51-5.67 (3H, m), 7.24 (2H, s)f 7.42-7.57 (3H, m), 7.66-7.69 (2Hf m), 8.00-8.02 (2H, m), 8.08 (1H, dd, J = 8.3, 1.5Hz), 8.36 (1H, s), 8.61 (1H, brd, J = 11.2Hz), 10.19 ( 1H brs). 2-208 1 H-NMR (CDGi3: DMS〇-d6=1:1) δ 5.99-6.25 (3H, m), 7.23-7.33 (4H, m), 7.46 (1H, t, J = 7.8Hz), 7.54-7.56 (1H, m), 7.68-7.72 (2H, m), 7.98-8.00 (1H, m), 8.29 (1H, s), 10.00 (1H, s), 10.46 (1H, s). 2-209 'H-NMR (CD€!3: DMSO-d5= 1:1) δ 6.00-6·25 (3H, m), 7·29 (2H, s), 7.45-7.52 (2Ht m), 7.72 (IH, d, ϋ =?.8Ης), 7.96-8.02 ( 2H, m), 8.24 (1H, d, J = 2.0Hz), 8.50 (1H} dd, J = 4.9, 2.0Hz), 10.03 (1H, s), 10.75 (1H, s). 135 200836629 Table 5 { 27) - ... - ...Chemical number 値1 2-210 ( ( 4-NMR (CDCb) d 5.15-5.31 (1H, m), 7.41-7.57 (4H, m)5 7.79 1H, d, 7.92 (2H , s), 8.0U.04 (2H, brd, J 2.7.3Hz), 8·18 1H, d, J =8.3Hz), 8.35 (1HT sX 9.85 (1H, s), 10.04 (1H, s). :\ 2-211 1 C H-NMR (CDCi3) ά 4.89-4.97 (1H, m), 7.1-8-7.26 (1H, m), 7.32-.3β (1H, m), 7.50-7.57 (2H? m), 7.76 (1H, d, J = 7.8 Hz), 7.89 (IH, i, J = 1.5 HzX 7.91 (2H, s), 8.02 (1H, s), 8.16 (1H, ddd, J = 7.8, 7.8 , LOHz), 8.32 (tH, t J =1-5Hz), 8.65 (1H, brd, J = 16.1 Hz). 1 2-212 ^ i H-NMR (CDCI3) δ 4.96 (1H, brd, J = 44.0 Hz), 7.37 (1H., dd, J = A 4.9Hz), 7·52 (1H, brd, J 7.8Hz), 7.75 (1H, d, J 2·7Ηζ), 7·89 1H, d , J = 8.3Ης), 7.90 (2 H, s), δ.02 (1H, s), 8.12 (1H, dd, J = 7.8, LOHz), 8·25 (1H, s), 8. (1H, dd, J = 4.9, 2.0H2 :), 8·64 (1H, s). 2-213 H-NMR (CDCi3: DMSO-de (5:1)) δ 5.7δ (1H, brd, J = 44.0 Hz), 7.46-7.59 (5H, m), 7.79 (1H, t? J = 2.0Hz), 7.90 (1H, t, J = 2.0Hz), S-00 (1H, d, J = K5Hz), 8.03 (1H, s), 8.12 (1H , dd, J 7.8, 1.5 Hz), δ.39 (1H, t J =2.0 Hz), 10.29 (1H, s)T 10.32 (1H, s). Xin• 2-214 H-NMR (CDCb) < ;5 5.30-5.95 (1H, m), 7.19-7.24 (tH, m), 7.32-7.36 m), 7.51-7-59 (2H, m), 7J6 (2H, d, J = 2OHz), 7.88 UH , d, J = 2.0Hz), 7.90-7.92 (2H, m), 8.18 (1H, ddd, J =7.3⁄4 7.8, 2.0Hz), 8.34 t J =2.〇Ηζλ 8.64 (1H, d, J =16.1 Hz). 2-215 1 H-NMR (CDCI3) δ 5.80-5.10 (1H, m)T 7.40 (t H, dd, J = 7.8, 4.9 Hz), 7.53 (1H, t, J = 7.8 Hz ), 7.75-7.78 (2H, m), 7.87 (1H? d, J = 2.0Hz), 7.88-7.91 (1H, m), 7.97 (1H, s), 8.16 (1H, dd, J = 7.8, 2.0 Hz)} 8.26 (1H, d, J = 2.0Hz), 8.51 (IH, dd, J = 4.4, 2.0Hz), 8.56 (1H, s). 2-216 !H-NMR (CDCI3) δ 3.55 (3HT s), 4.81-4.97 (1H, m), 7.19-7.33 (6H, m), 7.39 (1H? t, J = 7.8H zX 7.50 (1H, s), 7.58-7.61 (1H, m), 7·70-7.74 (1H, m)T 7.74 (1H, d, J II L5H£), 7.85 (1H, d, J =1.5Hz 2-217 'H-NMR (CDCi3) δ 3.53 (3H, brsX 4.74-4.98 (2HT m)T 6.84 (1H, brs), 7.08 (1H, brs), 7.17 (tH, dd, J =10r7T 8.3 Hz), 7.39-7.47 (3H, m), 7.55-7.60 (2H, m), 7.74 (1H, d, J = 2.0Hz), 7.86 (1H, d, J = 2.0Hz). 2-218 lH- NMR (CDCb) occupies 3.57 (3H, s), 4-91 (1H, brd, J 2 43.9 Hz), 7.13 (tH, dd, J - 7.8, 4.9 Hz), 7.39 (2H, d, J = 4.4 HzX) 7.58 (2H, brs), 7.71-7.75 (3H, m), 7.88 (1H, brs), B.25 (1H, d, J = 3.4Hz). 2-219 'H-NMR (CDCI3) 6 220 ( 6H, s)T 3.55 (3H, s)T 5.93 (1H, ddd, J = 54.2, 2.9, 2.9HzX 6.96 (2HT s), 7.10 (1H, dd, J = 7.3, 4.9Hz) T 7.35 (2H, d, J = 4.4 Hz), 7.46 (tHT s), 7.54 (1H, dd, J = 7.8, 2.0 Hz), 7.68 (1H, brd, J = 3.9 Hz), 7.73 (1H, s), 8.23 (1H , dd, J = 4.4, 1.5 Hz). 2-220 'H-NMR (CDCi3) 6 2.2B (6H, s), 5.00 (1H, brdd, J = 43.9, 5.4Ης), 6.87 (1H, d, J = 6.8 Hz), 6.97 (1H, s), 7.41 (1H, dd, J = 7.8T 4.9 Hz) T 7.52 (tH, t, J = 8.3 Hz), 7.58 (tH, brs), 7.72-7.74 ( 1H, m), 7.83-7.86 (1HT m X 8.17 (1H, dd, J - 7.8, 2.0 Hz), 8.27 (1H, brs), 8.52 (2H, brs). 2-8 ^-NMR (DMSO-d6) δ 6.18 (1H? brdd, J = 42.0 , 5.2Hz)T 7.23-7.32 (2H, m), 7Λ7-7.55 (2H, m), 7:62 (2H, s), 7J0 C1H, t J two 6.4Hz), 7.78 (1H, d, J = 6.8HzX 8.03 (1H, d, J = 7.6H2), 8.34 (tH, s), 10.38 (1H, s), 10.50 (1H, s). 4-1 'H-NIVIRCCDCis) 6 2.28(6H, s) , T.30-TM(5H, m), 7.34(2H, s), 7.51-7.64(4H, m)T 7.75-7J8(2H, m).. 4-2 lH-NMR(CDCI3) δ 2.29( 6H, s), 2.64(3H, s), 7.22-7.36(4H, ml 7.34C2H, s), 7.43-7.47(2H?m), 7.57-7.680H, m), 7.99(1 H, d, J = 7.3HzX 4-6 'H-NMRCCDCis) δ 2.29(6H, s), 7.32-7.39(6«, m), 7.58-7.66 (6H, m). 136 200836629 Table S(2S)
—fc合物編號」 物性値 命 i 4-10 ( ( H-NMR(CDGl3) δ 2.31 (6Η, s), 7.35(2H, s)f 7.43-7.47(2H, m)5 7.49 1H, s), 7.53(1H, s), 7.61-7.65(1H, m), 7J1-7.77(3H, m), 7.87-7.91 2H, m). 1 4-16 ( H-NMRCCDCI3) δ 2.33(6H, sX 7„36(2Ht s), 7.42-7.490H, mX 1J\ 1H, d, J = 6.8Hz), 7.BK1H, s), 7.89(1H, s). 1 4-24 H-NMR(CDCl3) δ 2.29(6H, s), 2.85(3H, s)f 3.35(3H, s), 7.34(2H, s), 7.49(1H, t, ϋ = 7.8Hz), 7.58(1H, dd, J = 1.0,7.8Hz), 7.8〇-7.83(2H, r〇, 7.96(1 H, s). 4-25 H-NMR(CDCI3) a 1.35(3R t, J = 7.3Hz), Z.32(6H, s), 3.14(2H, q, J = 7.3Hz), 7.2B(1H, s), 7.35(2H, s), 7.42-7.48(2H, m), 7.66-7.71 :2H, m), 7.80(1 H, s). 4-26 H-NMR(CDCi3) δ 1.33(3H, t( ϋ = ?.3Hz)f Z.27(6Ht s), 3.03(2H, q, J = 7.3Hz), 3.35(3H, s), 7.33(2H, s), 7.44(1 H, t, ϋ = 7.8Hz), 7.57( 1H, d, J = 7.8Hz), 7.79(1H, d, J = 7.8Hz), 7.97(1H, s), 8.05(tH, s). 4-27 lH-NMR(GDCl3) δ 2.27(6H, s), 3.73(2H, q, J = 8.8Hz), 7.33(2H, s), 7.39-7.45(2H, m), 7.6B-7.7K1H, m)t 7.83-7.85(2H, m), 8.09(1H, s). 4-28 lH-NMR(CDGl3) δ Z.27(6H, s), 3.40(3H, s), 3.75(2H, q, J = 8.8Hz), 7.34(2H, s), 7.51 (1H, t, J = 7.8Hz)? 7.58(1 H, d, J = 7.8Hz), 7.86(1 H, d, J = 7.8Hz), 7.B0(1H, s), 7.97(1H, s). 4-29 'H-NIVIRCCDGis) δ 2.25(6H, s), 5.87(1H, d, J = δ.δΗζ), 6.19(1H, d, J = 16.1Hz), 6.46(1H, dd, ϋ = 9.8,16.1Hz), 7.23-7.35(5H, m), 7.61 (IH, s), 7.75(1H, s), 7.94(1H, s). 4-30 lH-NMR(CDCl3) δ 2.28(6H, s), 3.25(3H, s), 6.03(1 H, d, J = 9.8HzX 6.18(1HT d, J = 16.6Hz)? 6.42(1H, dd, J = 9.8,16.6Hz), 7.33(2H, s), 7.44(1H, t J = 7.8Hz), 7.51(1HT d, J = 7.8Hz), 7.80(1H, d, J = 7.8Hz), 7.9K1H, s), 7.94(1H, s). 4-31 lH-NlVlR(DiVIS〇-d6) δ 1.02(3H t, J = 7.3Hz), 1.80-1.90(2H, m), 2.35(6H, s), 3.05-3.09(2H, m), 7.32(2H, s), 7.42(1 H, t? J = 7.8Hz), 7.50-7.53(1H, m), 7.71(1H, d, J = 7.8Hz), 7.86(1^ d, ϋ = 2.0Hz), 8.54(1 H, s), 9.24(1 H s). 4-32 'H-NMRCCDCIs) 6 1.01(3H, t, vi = 7.8Hz), 1.77-l.87(2Hf m), 2.28 (6H, s), 2.97(2H, t, J = 7.8Hz), 3.35(3H, s), 7.34(2H, s), 7.45( 1H, t, J = 7.8Hz)( 7.57(1 H, d, J = 7.8Hz), 7.80(1 H, d, J = 7.8Hz), 7.9? (2H, s). 4-33 'H-NMRiCDCIs) δ 1.37(6H, d, J = 6.8Hz)t 2.32(6H, s), 3.31(1H, septet, J = 6.8Hz), 7.24(1H, s), 7.35(2H, s), 7.41-7.49(2H, m), 7.66 (1H, d, J = 7.3Hz), 7.7K1H, s), 7.81 (ΊΗ, s). 4-34 'H-NlVlRCCDCis) δ 2.35(BH, s), 4.37(2H, s), 6.72(1 H, s), 121-1.31 (8Hf m\ 7.43-7.47C2H, m), 7.62(1 H, d, J = 2.0Hz), 7.68(1 H, d, J = 7.8Hz). 5-1 'H NMR(CDOi3) dZ.35 (6Ht s), 5.89 (1Hf brs), 7.01 (1H, t, J = 7.3Hz), 7.14 (2H, dt J =7.3Hz), 7.28-7.40 (8H, m), 7.80 (1H, brs). 5-2 NMR(GDCI3) ί Z.28 (3H, s), 2.35 (6H, s), 5.58 (1H, brs), 7.00 (1H t,J =7.3Hz), 7.09 (1H cU =7.3Hz), 7.18 (1ΗΛ J =7.3Hz), 7.24-7.35 (7H, m), 7.53 (1H, brs). 137 200836629 表糊-fc compound number" physical property i 4 4 ( ( H-NMR(CDGl3) δ 2.31 (6Η, s), 7.35(2H, s)f 7.43-7.47(2H, m)5 7.49 1H, s) , 7.53(1H, s), 7.61-7.65(1H, m), 7J1-7.77(3H, m), 7.87-7.91 2H, m). 1 4-16 (H-NMRCCDCI3) δ 2.33(6H, sX 7 „36(2Ht s), 7.42-7.490H, mX 1J\ 1H, d, J = 6.8Hz), 7.BK1H, s), 7.89(1H, s). 1 4-24 H-NMR(CDCl3) δ 2.29(6H, s), 2.85(3H, s)f 3.35(3H, s), 7.34(2H, s), 7.49(1H, t, ϋ = 7.8Hz), 7.58(1H, dd, J = 1.0, 7.8 Hz), 7.8〇-7.83(2H, r〇, 7.96(1 H, s). 4-25 H-NMR(CDCI3) a 1.35(3R t, J = 7.3Hz), Z.32(6H, s ), 3.14(2H, q, J = 7.3Hz), 7.2B(1H, s), 7.35(2H, s), 7.42-7.48(2H, m), 7.66-7.71 :2H, m), 7.80(1 H, s). 4-26 H-NMR (CDCi3) δ 1.33 (3H, t( ϋ = ?.3Hz)f Z.27(6Ht s), 3.03(2H, q, J = 7.3Hz), 3.35( 3H, s), 7.33(2H, s), 7.44(1 H, t, ϋ = 7.8Hz), 7.57( 1H, d, J = 7.8Hz), 7.79(1H, d, J = 7.8Hz), 7.97 (1H, s), 8.05(tH, s). 4-27 lH-NMR(GDCl3) δ 2.27(6H, s), 3.73(2H, q, J = 8.8Hz), 7.33(2H, s), 7.39 -7.45(2H, m), 7.6B-7.7K1H, m)t 7.83-7.85(2H, m), 8.09(1H, s). 4-28 lH-NMR(CDGl3) δ Z.27(6H, s), 3.40(3H, s), 3.75(2H, q, J = 8.8Hz), 7.34(2H, s), 7.51 (1H, t, J = 7.8Hz)? 7.58( 1 H, d, J = 7.8 Hz), 7.86 (1 H, d, J = 7.8 Hz), 7. B0 (1H, s), 7.97 (1H, s). 4-29 'H-NIVIRCCDGis) δ 2.25 (6H, s), 5.87(1H, d, J = δ.δΗζ), 6.19(1H, d, J = 16.1Hz), 6.46(1H, dd, ϋ = 9.8,16.1Hz), 7.23-7.35(5H , m), 7.61 (IH, s), 7.75(1H, s), 7.94(1H, s). 4-30 lH-NMR(CDCl3) δ 2.28(6H, s), 3.25(3H, s), 6.03 (1 H, d, J = 9.8HzX 6.18(1HT d, J = 16.6Hz)? 6.42(1H, dd, J = 9.8,16.6Hz), 7.33(2H, s), 7.44(1H, t J = 7.8 Hz), 7.51 (1HT d, J = 7.8Hz), 7.80(1H, d, J = 7.8Hz), 7.9K1H, s), 7.94(1H, s). 4-31 lH-NlVlR(DiVIS〇-d6 δ 1.02(3H t, J = 7.3Hz), 1.80-1.90(2H, m), 2.35(6H, s), 3.05-3.09(2H, m), 7.32(2H, s), 7.42(1 H, t? J = 7.8 Hz), 7.50-7.53 (1H, m), 7.71 (1H, d, J = 7.8 Hz), 7.86 (1^d, ϋ = 2.0 Hz), 8.54 (1 H, s), 9.24 (1 H s). 4-32 'H-NMRCCDCIs) 6 1.01 (3H, t, vi = 7.8 Hz), 1.77-l.87 (2Hf m), 2.28 (6H, s), 2.97 (2H, t, J = 7.8 Hz), 3.35 (3H, s), 7.34 (2H, s), 7.45 (1H, t, J = 7.8 Hz) ( 7.57 (1 H, d, J = 7.8 Hz), 7. 80(1 H, d, J = 7.8Hz), 7.9? (2H, s). 4-33 'H-NMRiCDCIs) δ 1.37(6H, d, J = 6.8Hz)t 2.32(6H, s), 3.31 (1H, septet, J = 6.8Hz), 7.24(1H, s), 7.35(2H, s), 7.41-7.49(2H, m), 7.66 (1H, d, J = 7.3Hz), 7.7K1H, s ), 7.81 (ΊΗ, s). 4-34 'H-NlVlRCCDCis) δ 2.35(BH, s), 4.37(2H, s), 6.72(1 H, s), 121-1.31 (8Hf m\ 7.43-7.47 C2H, m), 7.62 (1 H, d, J = 2.0 Hz), 7.68 (1 H, d, J = 7.8 Hz). 5-1 'H NMR (CDOi3) dZ.35 (6Ht s), 5.89 ( 1Hf brs), 7.01 (1H, t, J = 7.3Hz), 7.14 (2H, dt J =7.3Hz), 7.28-7.40 (8H, m), 7.80 (1H, brs). 5-2 NMR(GDCI3) ί Z.28 (3H, s), 2.35 (6H, s), 5.58 (1H, brs), 7.00 (1H t, J = 7.3Hz), 7.09 (1H cU = 7.3Hz), 7.18 (1ΗΛ J = 7.3 Hz), 7.24-7.35 (7H, m), 7.53 (1H, brs). 137 200836629
一重合物編號 物te値 I 5-4 i 1: H NMR(CDCl3) (52.35 (6H, s), 5.98 (1H, brs), 6.64-6.69 (1H, m), 180-6.85 (2H, mX 7.20-7.24 (1H, m)T 7.31-7.43 (6H, m), 7.63 (1H, 3rs). 1 5-5 H-NMR(CDCI3) 52,34 (6H, s), 5.88 (1H, brs), 7.00 (2Ht d, J =8.8Hz), 7.36 (2H; s), 7.38-7.41 (6H, m), 7.59 (1H, brs). , • 5-8 H-NMR(GDGi3) δ 2.37 (6H, s), 6.85-6.89 (1H, m), 7.32 (1H, d, J =8.8Hz), 7.37-7.46 (4H, m), 7.51-7.59 (2H, m), 7.71 (1H, d, J = 7.3Hz), 7.87 (1H, brs), 8.23 (1H, dd, J =8.8t1.5Hz), 9.54 (1H, brs). 5-9 H-NMR(GDCi3) § 2.36 (6H, s), 6.50 (1H, brs), 7.02 (ZHt d, ϋ = δ.7Ηζ), 7.38 (2H, s), 7.42 (1H, s), 7.46 (1H, d, J =7.8Hz)t 7.53 ΠΗ, t, J =7.8Hz), 7.60 (1H, d, J =7.8Hz), 7.91 (1H, brs), 8.19 (2H, d, J =8.7Hz). 5-10 'H-NMRCCDCy (5Z.32 (6H, s), 3.81 (2H, brs), 5.42 (1H, brs), 6.76-6.83 (2H, m), 6.87-6.89 (1H, m), 7.05-7.09 (1H, m), 7.12 (1H, d, J =7.8Hz)? 7.27-7.37 (6H, m). 5-11 'H-NMRCCDCls) δ Ζ33 (6H, s), 5.60 (1H, brs), 6.64 (2H, brs), 6.69 (2H d, J =8.8Hz)i 7.00-7.02 (3H, m), 7.23-7.37 (6H, m). 5-12 ^-NMRiCDCig) 6'2.34 (6H, s), 6.04 (1H, brs), 7.20-7.52 (10H, m), 7.64 (1Ht brs). 5-13 'H-NMRiCDCls) ^2.08 (3H, s), Z3Z (6H, s), 5.98 (1H, brs), 6.98 (1H, d, J =7.3Hz), 7.16-7.22 (2H, mX 7.29-7.40 (7H, m), 7.59 (1H, brs), 7.68 (1H, d J =7.3Hz). 5H4 'H-NIVIRCCDCIs) 52.13 (3H, s), 2.33 (6H, s), 5.87 (1H, brs), 7.06 (2H, d, J =8.8Hz), 7.19 (1H, brs), 7.30-7.41 (7H, m), 7.50 (1H, brs), 7.53 (1H, brs). 5-15 ^ 'H-NMRCGDCis) δ 2.34(6H, s)t 5.74(1 H, broad-s), 6.83-6.95(2H, m), 7.15-7.18(1H, m),7.18-7.39(6H, m), 7.54(1H, broad-s). 5-21 'H-NMRCCDCIs) 52.36 (6H, s)5 6.73-6.77 (2H, m), 6.96 (1H, d, J =7.3Hz),7.33-7.38 (3H,m), 143-149 (2H, m),7.56-7·58 (2H,m), 8.12 (1H, s). 5-23 'H-NMRCCDGis) §2.31 (6H, s), 6.08 (2Ht brs), 7.35 (2H, s), 7.43-7.59 (2H, m), 7.70-7.82 (3H, m), 8.29 (1H, brs). 5-24 'H-NMRiCDCis) ^2.33 (6H, s), 5.93 (2H, brs), 7.36 (2H, s), 7.45-7.49 (2H, m), 7.63 (1H, s), 7.85 (1H, d, J =7.3Hz), 7.92 (1H, s), 8.04 (1H, s). 5-25 Ή-ΝΜΗίΟΜΒΟ^ρ) δ2.ΖΒ (6Ht s), 5.90 (2H, brs), 7.30-7.36 (2H, m), 7.43 (2H, s), 7.75 (1H, d, J =7.8Hz), 8.04 (1H, brs), 8.85 (1H, brs), 9.80 (1H, brs), 11.2 (1H, brs). 5-26 ^H-NMRlDMSO-dg) d2.33 (6H, sX Z.83 (6H, s)t 7.10-7.21 (3H, m), 7.43 (?H. sCi. 9_96 f1H. si 138 200836629 表 5(3_ 二二-.二 一二―.....-— ir編號…- 物性値 · —— 5 - 27 'H-NMRCCDGla) δ 0.92(3Ht t, ϋ = 7.3Hz), 1.59-1.69(2H, m), 2.72 (2H, t ϋ = 7.8Hz), 3.03(6H, s), 6.93(1 H, dd, J = 2.4,8.3Hz), 7.23(1H, d, J = 8.3HzX 7.32-7.39C2H, m), ?.50(1Hf s), 7.55(1H, s), 7.95(1H, dv J = 1.5Hz). —— 5-28 lH-NMR(CDCl3) δ 1.23(6H, d, J = 6.8Hz), 3.04(6H, s), 3.25(1H, septet, J = 6.8Hz), 6.93(1 H, dd, J = 2.0f?.8Hz), 7.23(1 H, t, J = 7.8Hz), 7.33-7.39(2H, m), 7.51(1H, s), 7.57(1H, s), 7.95(1H, d, J = 2.0Hz). 5-29 'H-NMRCGDCig) δ 3.05(6H, s), 3.07(3H, s), 6.97(1 H, dd, J = ZQ, 7.8Hz), 7.25-7.27(1 H, m), 7.32-7.33(1 H, m), 7.39(1 H, t, J = 7.8Hz), 8.20(1 H, d, J = ZOHz), 8.26(1 H d, J = 2.0Hz), 8.89(1 H, s). 5-30 ]H-NMR (CDCi3) δ 3.04(6H, s), 6.95(1H, dt J = 7.8Hz), 7.21-7.23 (1K m), 7.33-7.39C2H, m), 7.66(1 K s), 7.93(2H, s). 5-31 lH-NMR(DMS〇-d6) δ 2.97 (6H, s), 6.38-6.52 (1H, m), 6.96 (1H, brdd, J =8.8, 2.0Hz), 7.28-7.36 (3H, m), 8.06 (2H, s), 10.34 (1H, s). 5~32 Ή NMR (CDCI3) δ 2.84 (6H, s), 3.35 (3H, s), 6.63-6.65 (1H, m), 6.73 (1H, d, J =3.9Hz), 6.75 (1H, s), 7.03 (1H, t, ϋ =8.3Hz), 8.09 (2K s). 5 - 33 Ή-ΝΜΗ(0Ρ0ί3) δ 1.57(3H, d, J = 6.8Hz), 2.28(6H, s), 2.74(3H, s), 5.18C1H, q, J = 6.8Hz), 6.99(1H, dd, J = 2.4,8.3Hz)t 7.15(1H/d, J = 7.3Hz), 7.22-7.35(8H, m), 7.4K1H, s), 7.55(1H, s). 表 5(31) 化额編號i 物性値 6-1 I 1HtIMMR(CDCI3) δ 2.36(6Ht s), 7.34(2HT s), 7.46-7.57C4H, m)t 7.76(1 H, d, J 7.3Hz),8.00(2Ht d, J = 7.3Hz), 8.13(1 H,cU 二 7.3Hz), 8·35(1Η,s), 9-10(1 H, broad-s),9.88(1 H,broad-s). 6-2 1H-NMR(CDG13) 6' 2.33(6H, s)T 7.35(2H, s), 7.39-7.46(1 HT m), 7.52(1 H, t, J 7.8Hz), 7.73-7.75(2K m), 7.83(1 K d, J = 8.3Hz), 8.16(1 K ddf J = 7.8T2.0Hz), 8.30(1 H, broad-sX 8.52(2H, ddf J = 4.9r2.0Hz). 6-3 1H-NMR(CDC!3) δ 2.34(6H, si 3.55(3H, s), 7.13(1 HT broad-s), 7.19-7.42(9H, m)T 7.55(1 H,broad-s),7.89(1 H,d J = 6.8Hz)· 6-4 1H-NMR(CDCI3) δ 2.28(6HT s), 3.57(3HT sX 7.11-7.14(1 H, mX 7.30-7.37(4H, m),7.57(1 H,d,J = 6.8Hz)T 7-68-7.72(3H,m),8·24(1 H,d J 二 3.4Hz). 傷 6- 5 1H-NMR(CDCI3) δ 2.34(3H, s)¥ 3.55(3H, s), 7.19-7.72(12K m). 6-δ 1H-NMR(CDCi3) 2^8(3/2HT s), 2.37(3/2HT s\ 3.58(3H, s), 7.11-7.15(1 Hr m),7.37-7.41 (3H,m)· 7.48-7.64(3H,m),7·82(2Η,broad—s),8.25(1 H,broad-s). 6-7 1H-NMR(CDCI3) <5 7.5〇-7.59(4H, m), 7.75(1 H, dd, J = 6.8r1.5Hz), 7.88-7.92(2H,m). 7·99-8-05(4K m), 8.29(1H,broad-s), 8.30(1H乂 J 二 1·5Ηζ)· 6-8 1H_NMR(CDGI3) <5 7Λ3—7-4S(1H,m),7·57(1Η,t J = 7·8Ηζι),7.76—7.80(1!4, m), 7.93-8.03(3^ m), 8.21-8.27(2H, m), 8.32(1 H, s), 8.40(1 H, broad-s), 8.56(1 H, t J =1.5Hz:). 6-9 1H-NMR(CDGI3) δ 7.49-7.59(5H, m), 7.73-7.75(1 H, mX 7.88-7.92C3H, mX 8.12-8.13(1 H, mX 8.20(1 H, broad-s)T 8.30(1 H, d, J = 7.4Hz), 8.36(1 H, broad-s). *6-10 1{-Ην1ΜΚ^ΟΟ!3)δΙ43-7.46(1Η,Γη),7·56(1ΗΛϋ = ;?·6ΗζΧ7·75-7.80(1Η,Γη), 7.90(1 H,d,J = 7·3Ηζ),8.12-8.15(1 H,m),8.21-8.24(1 H,m), 8.30(1 H,broad-s), 8.33(1 H, broad~s), 8.46-8.48(2H, m), 8.54-8.58(1 H, m). 6_11 1H-NMR(CDCI3) 6' 3;56T3.57(3H, two s), 7.23-7.330H, m), 7.38-7.48(3H, m), 7.53-7.57(1 H, m), 7.67-7.72(2H, m)( 8.03-8.04(1 H, mX 8.10-8.11 (1H, mX 8.26(1 H,broad—s)· 6-12 1H-NMR(CDCI3) 6 3.58(3H, sX 7.14-7.16(1 H, mX 7.45(2K broad-s), 7.52-7.80(3H. ml 8.10(1 H. broad-si 9.21-8.30(3K m). 139 200836629 化合物編號 1-187 之物性値 1H—NMR(CDC13) (5 3·54(3Η,s), 7 i g-7】2(ffi,m),7·27·7·30( 3H,m),7·33-7·36(1Η,m),7·42(1Η,t5 J =7·8Ηζ),7.57(1¾ s),7·67_7·70(1Η,m),7.88(1¾ s), 8.02(1¾ d,J = 2·0Ηζ),8· 10(1H,d,卜 2·0Ηζ)。 本發明之殺蟲組成物能防治之害蟲具體例,例如,鱗翅目 (LEPIDOPTERA)之蝙蝎蛾(Endoclyta excrescens)、黃斑蝙虫畐蛾 (Endoclyta sinensis)、Palpifer sexnotata(白點编虫畐蛾、Dasheen tree-borer)、Acleris comariana(薔薇捲葉蛾、Strawberry tortrix)、茶 姬捲葉蛾(Adoxophyes oranafasciata)、姬捲葉蛾(Adoxophyes sp.)、 捲葉蛾(Archips breviplicanus)、亂紋蘋果捲葉蛾(Archips foscocupreanus)、Archips xylosteanus(角紋捲葉蛾、Apple leaf roller)、Bactra forfurana(藺草虫主心蛾、Mat rush worm)、Cnephasia cinereipalpana(灰色細捲葉蛾)、Cydia kurokoi(栗實蛾、Nut fruit tortrix)、Eucoenogenes aestuosa(栗綠虫主心蟲)、蘋果小食心蟲 (Grapholita inopinata)、桃折心蟲(Grapholita molesta)、茶捲葉蛾 (Homona magnanima)、Hoshinoa adumbratana(蘋果大捲葉蛾)、大 豆食心蟲(Leguminivora glycinivorella) 、Matsumuraeses azukivora(紅豆英蟲)、Matsumuraeses Mcana(大豆莢蟲)、 Matsumuraeses phaseoli(小豆笑蟲、Azuki pod worm)、Olethreutes 11101:汉桑姬捲葉蛾)、蘋果白捲葉蛾(8卩丨1〇11(^以111如3卩丨5)、8卩丨1〇11(^ ocellana(蘋果姬白捲葉蛾、Eye_spotted bud moth)、Eupoecillia ambiguella(葡萄細捲葉蛾)、Phalonidia mesotypa(慈姑細捲葉蛾)、 艾草大細捲葉蛾(Phtheochroides clandestine)、顏果蠹蛾(Cydia pomonella)、葡萄果實虫主蟲(Endopiza viteana)、Bambalina sp·(避債 蛾類)、大避債蛾(Eumetajaponica)、茶避債蛾(Eumetaminuscula)、 穀蛾(Nemapogon granellus)、衣蛾(Tinea translucens)、Bucculatrix pyrivorella(梨倭小蛾、Pear leaf miner)、桃潛葉蛾(1^〇11^11& clerkella)、Lyonetiapmnifoliella(銀紋潛葉蛾)、Caloptilia soyella(豆 細蛾}、茶細蛾(Caloptilia theivora)、Calopyilia zachrysa(蘋果細蛾)、 140 200836629One heavy compound number te値I 5-4 i 1: H NMR (CDCl3) (52.35 (6H, s), 5.98 (1H, brs), 6.64-6.69 (1H, m), 180-6.85 (2H, mX 7.20-7.24 (1H, m)T 7.31-7.43 (6H, m), 7.63 (1H, 3rs). 1 5-5 H-NMR (CDCI3) 52,34 (6H, s), 5.88 (1H, brs) , 7.00 (2Ht d, J = 8.8Hz), 7.36 (2H; s), 7.38-7.41 (6H, m), 7.59 (1H, brs). , • 5-8 H-NMR(GDGi3) δ 2.37 (6H , s), 6.85-6.89 (1H, m), 7.32 (1H, d, J = 8.8Hz), 7.37-7.46 (4H, m), 7.51-7.59 (2H, m), 7.71 (1H, d, J = 7.3 Hz), 7.87 (1H, brs), 8.23 (1H, dd, J = 8.8t1.5Hz), 9.54 (1H, brs). 5-9 H-NMR(GDCi3) § 2.36 (6H, s), 6.50 (1H, brs), 7.02 (ZHt d, ϋ = δ.7Ηζ), 7.38 (2H, s), 7.42 (1H, s), 7.46 (1H, d, J = 7.8Hz)t 7.53 ΠΗ, t, J = 7.8 Hz), 7.60 (1H, d, J = 7.8 Hz), 7.91 (1H, brs), 8.19 (2H, d, J = 8.7 Hz). 5-10 'H-NMRCCDCy (5Z.32 (6H) , s), 3.81 (2H, brs), 5.42 (1H, brs), 6.76-6.83 (2H, m), 6.87-6.89 (1H, m), 7.05-7.09 (1H, m), 7.12 (1H, d , J = 7.8 Hz)? 7.27-7.37 (6H, m). 5-11 'H-NMRCCDCls) δ Ζ33 (6H, s), 5.60 (1H, brs), 6.64 (2H, brs), 6.69 (2H d , J = 8.8Hz) i 7.00-7.02 (3H, m), 7.23-7.37 (6H, m). 5-12 ^-NMRiCDCig) 6'2.34 (6H, s), 6.04 (1H, brs), 7.20-7.52 (10H, m), 7.64 (1Ht Brs). 5-13 'H-NMRiCDCls) ^2.08 (3H, s), Z3Z (6H, s), 5.98 (1H, brs), 6.98 (1H, d, J =7.3Hz), 7.16-7.22 (2H , mX 7.29-7.40 (7H, m), 7.59 (1H, brs), 7.68 (1H, d J =7.3Hz). 5H4 'H-NIVIRCCDCIs) 52.13 (3H, s), 2.33 (6H, s), 5.87 (1H, brs), 7.06 (2H, d, J = 8.8 Hz), 7.19 (1H, brs), 7.30-7.41 (7H, m), 7.50 (1H, brs), 7.53 (1H, brs). 5- 15 ^ 'H-NMRCGDCis) δ 2.34(6H, s)t 5.74(1 H, broad-s), 6.83-6.95(2H, m), 7.15-7.18(1H, m), 7.18-7.39(6H, m ), 7.54(1H, broad-s). 5-21 'H-NMRCCDCIs) 52.36 (6H, s)5 6.73-6.77 (2H, m), 6.96 (1H, d, J =7.3Hz), 7.33-7.38 (3H,m), 143-149 (2H, m), 7.56-7.58 (2H,m), 8.12 (1H, s). 5-23 'H-NMRCCDGis) §2.31 (6H, s), 6.08 (2Ht brs), 7.35 (2H, s), 7.43-7.59 (2H, m), 7.70-7.82 (3H, m), 8.29 (1H, brs). 5-24 'H-NMRiCDCis) ^2.33 (6H, s), 5.93 (2H, brs), 7.36 (2H, s), 7.45-7.49 (2H, m), 7.63 (1H, s), 7.85 (1H, d, J = 7.3Hz), 7.92 (1H, s ), 8.04 (1H, s). 5-25 Ή -ΝΜΗίΟΜΒΟ^ρ) δ2.ΖΒ (6Ht s), 5.90 (2H, brs), 7.30-7.36 (2H, m), 7.43 (2H, s), 7.75 (1H, d, J = 7.8Hz), 8.04 ( 1H, brs), 8.85 (1H, brs), 9.80 (1H, brs), 11.2 (1H, brs). 5-26 ^H-NMRlDMSO-dg) d2.33 (6H, sX Z.83 (6H, s )t 7.10-7.21 (3H, m), 7.43 (?H. sCi. 9_96 f1H. si 138 200836629 Table 5 (3_二二-.二二二-.....-- ir number...- physical properties値· —— 5 - 27 'H-NMRCCDGla) δ 0.92(3Ht t, ϋ = 7.3Hz), 1.59-1.69(2H, m), 2.72 (2H, t ϋ = 7.8Hz), 3.03(6H, s), 6.93 (1 H, dd, J = 2.4, 8.3 Hz), 7.23 (1H, d, J = 8.3HzX 7.32-7.39C2H, m), ?.50(1Hf s), 7.55(1H, s), 7.95(1H , dv J = 1.5Hz). —— 5-28 lH-NMR(CDCl3) δ 1.23(6H, d, J = 6.8Hz), 3.04(6H, s), 3.25(1H, septet, J = 6.8Hz) , 6.93(1 H, dd, J = 2.0f?.8Hz), 7.23(1 H, t, J = 7.8Hz), 7.33-7.39(2H, m), 7.51(1H, s), 7.57(1H, s), 7.95 (1H, d, J = 2.0 Hz). 5-29 'H-NMRCGDCig) δ 3.05(6H, s), 3.07(3H, s), 6.97(1 H, dd, J = ZQ, 7.8 Hz), 7.25-7.27(1 H, m), 7.32-7.33(1 H, m), 7.39(1 H, t, J = 7.8Hz), 8.20(1 H, d, J = ZOHz), 8.26( 1 H d, J = 2.0Hz ), 8.89(1 H, s). 5-30 ]H-NMR (CDCi3) δ 3.04(6H, s), 6.95(1H, dt J = 7.8Hz), 7.21-7.23 (1K m), 7.33-7.39 C.sub.2, m. 1H, brdd, J = 8.8, 2.0 Hz), 7.28-7.36 (3H, m), 8.06 (2H, s), 10.34 (1H, s). 5~32 Ή NMR (CDCI3) δ 2.84 (6H, s) , 3.35 (3H, s), 6.63-6.65 (1H, m), 6.73 (1H, d, J = 3.9Hz), 6.75 (1H, s), 7.03 (1H, t, ϋ =8.3Hz), 8.09 ( 2K s). 5 - 33 Ή-ΝΜΗ(0Ρ0ί3) δ 1.57(3H, d, J = 6.8Hz), 2.28(6H, s), 2.74(3H, s), 5.18C1H, q, J = 6.8Hz) , 6.99(1H, dd, J = 2.4, 8.3Hz)t 7.15(1H/d, J = 7.3Hz), 7.22-7.35(8H, m), 7.4K1H, s), 7.55(1H, s). Table 5(31) Chemical number i Physical properties 値6-1 I 1HtIMMR(CDCI3) δ 2.36(6Ht s), 7.34(2HT s), 7.46-7.57C4H, m)t 7.76(1 H, d, J 7.3Hz) , 8.00 (2Ht d, J = 7.3Hz), 8.13 (1 H, cU two 7.3 Hz), 8·35 (1Η, s), 9-10 (1 H, broad-s), 9.88 (1 H, broad -s). 6-2 1H-NMR(CDG13) 6' 2.33(6H, s)T 7.35(2H, s), 7.39-7.46(1 HT m), 7.52(1 H, t, J 7.8Hz), 7.73-7.75 (2K m), 7.83 (1 K d, J = 8.3 Hz), 8.16 (1 K ddf J = 7.8 T2.0 Hz), 8.30 (1 H, broad-sX 8.52 (2H, ddf J = 4.9r2.0 Hz). 6-3 1H-NMR (CDC!3 δ 2.34(6H, si 3.55(3H, s), 7.13(1 HT broad-s), 7.19-7.42(9H, m)T 7.55(1 H, broad-s), 7.89 (1 H, d J = 6.8 Hz)·6-4 1H-NMR (CDCI3) δ 2.28(6HT s), 3.57(3HT sX 7.11-7.14(1 H, mX 7.30-7.37(4H, m), 7.57(1 H,d,J = 6.8 Hz) T 7-68-7.72 (3H, m), 8·24 (1 H, d J 3.4 Hz). Injury 6- 5 1H-NMR (CDCI3) δ 2.34 (3H, s) ¥ 3.55 (3H , s), 7.19-7.72 (12K m). 6-δ 1H-NMR (CDCi3) 2^8(3/2HT s), 2.37(3/2HT s\ 3.58(3H, s), 7.11-7.15(1 Hr m), 7.37-7.41 (3H, m)· 7.48-7.64 (3H, m), 7.82 (2Η, broad-s), 8.25 (1 H, broad-s). 6-7 1H-NMR( CDCI3) <5 7.5〇-7.59(4H, m), 7.75(1 H, dd, J = 6.8r1.5Hz), 7.88-7.92(2H,m). 7·99-8-05(4K m) , 8.29 (1H, broad-s), 8.30 (1H乂J 2·5Ηζ)·6-8 1H_NMR(CDGI3) <5 7Λ3—7-4S(1H,m),7·57(1Η,t J = 7·8Ηζι), 7.76-7.80(1!4, m), 7.93-8.03(3^m), 8.21-8.27(2H, m), 8.32(1 H, s), 8.40(1 H, broad- s), 8.56 (1 H, t J = 1.5 Hz:). 6-9 1H-NMR (CDGI 3) δ 7.49-7.59(5H, m), 7.73-7.75 (1 H, mX 7.88-7.92C3H, mX 8.12-8.13 (1 H, mX 8.20(1 H, broad-s)T 8.30(1 H, d , J = 7.4Hz), 8.36(1 H, broad-s). *6-10 1{-Ην1ΜΚ^ΟΟ!3)δΙ43-7.46(1Η,Γη),7·56(1ΗΛϋ = ;?·6ΗζΧ7· 75-7.80(1Η,Γη), 7.90(1 H,d,J=7.3·3Ηζ),8.12-8.15(1 H,m),8.21-8.24(1 H,m), 8.30(1 H,broad- s), 8.33 (1 H, broad~s), 8.46-8.48 (2H, m), 8.54-8.58 (1 H, m). 6_11 1H-NMR (CDCI3) 6' 3; 56T3.57 (3H, two s), 7.23-7.330H, m), 7.38-7.48(3H, m), 7.53-7.57(1 H, m), 7.67-7.72(2H, m)( 8.03-8.04(1 H, mX 8.10-8.11 (1H, mX 8.26(1 H, broad-s)· 6-12 1H-NMR(CDCI3) 6 3.58(3H, sX 7.14-7.16(1 H, mX 7.45(2K broad-s), 7.52-7.80(3H . ml 8.10(1 H. broad-si 9.21-8.30(3K m). 139 200836629 Compound No. 1-187 Physical Properties 値1H-NMR(CDC13) (5 3·54(3Η,s), 7 i g-7 】 2 (ffi, m), 7·27·7·30 ( 3H, m), 7·33-7·36 (1Η, m), 7·42 (1Η, t5 J =7·8Ηζ), 7.57 ( 13⁄4 s), 7·67_7·70 (1Η, m), 7.88 (13⁄4 s), 8.02 (13⁄4 d, J = 2·0Ηζ), 8·10 (1H, d, Bu 2·0Ηζ ). Specific examples of pests which can be controlled by the insecticidal composition of the present invention, for example, Endoclyta excrescens, Endoclyta sinensis, and Palpifer sexnotata (Lepidoptera moth, LEPIDOPTERA) Dasheen tree-borer), Acleris comariana (Avixophyes oranafasciata), Adoxophyes sp., Archips breviplicanus, Archips foscocupreanus, Archips xylosteanus Cleaved leaf moth, Apple leaf roller, Bactra forfurana, Cnephasia cinereipalpana, Cydia kurokoi (Nut fruit tortrix), Eucoenogenes aestuosa (Chestnut worm) Heartworm), Grapholita inopinata, Grapholita molesta, Homona magnanima, Hoshinoa adumbratana, Leguminivora glycinivorella, Matsumuraeses azukivora , Matsumuraeses Mcana (soybean worm), Mats Umuraeses phaseoli (Azuki pod worm), Olethreutes 11101: Hansui leaf moth, apple white leaf moth (8卩丨1〇11 (^ with 111 such as 3卩丨5), 8卩丨1〇11 (^ Ocellana (Eye_spotted bud moth), Eupocelilla ambiguella, Phalonidia mesotypa, Phtheochroides clandestine, Cydia pomonella, grape fruit worm Endopiza viteana, Bambarina sp. (Ethopean moth), Eumetajaponica, Eumetaminuscula, Nemapogon granellus, Tinea translucens, Bucculatrix pyrivorella Pear leaf miner, Peach leaf moth (1^〇11^11& clerkella), Lyonediamnifoliella (Silver leaf miner), Caloptilia soyella (Cole moth), Caloptilia theivora, Calopyilia zachrysa (apple moth), 140 200836629
Cuphodes diospyrosella(柿、細蛾)、Phyllonorycter ringoniella(金、纹細 蛾、Apple leaf miner)、Spulerrina astaurota(梨細蛾)、蜜柑潛葉蛾 (Phyllocnistis citrella)、Phyllocnistis toparcha(葡萄潛葉蛾)、 Acrolepiopsis sapporensis (蔥小蛾)、Acrolepiopsis suzukiella(山芋小 蛾)、小菜蛾(Plutella xylostella)、Argyresthia conjugella(蘋果姬食心 蟲、Apple fruit moth)、Paranthrene regalis(葡萄透翅蛾、Grape clearwing moth)、Synanthedon hector(小透翅蛾、Cherry tree borer)、 Stathmopodamasinissa(柿蒂蛾)、Brachmiatriannulella(甘藷牙蛾)、 棉鈴蟲(Pectinophora gossypiella)、馬鈴薯塊莖蛾(Phthorimaea operculella)、Carposina niponensis(杉匕食心蛾、Peach fruit moth)、 Illiberis prnni(蘋果捲葉黑翅蛾)、Latoia sinica(黑下青刺蛾)、黃刺 蛾(]\^01^11^£1^^306113)、梨剌蛾(7^1*08(^(161^他¥丨(1(似&也)、青剌蛾 (Parasa consocia)、Scopelodes contracus(姬黑剌蛾)、二化填(Chilo suppressalis)、瘤野填(Cnaphalocrosis medinalis)、桃黃蛾(Conogethes punctiferalis)、瓜絹野模蛾(Diaphania indica)、Ectomyelois pyrivorella(梨斑螟)、褐斑螟(Ephestia elutella)、Ephestia kuehniella(條粉斑填蛾)、白緣模蛾(Etiella zinckenella)、Euzophera batangensis(黑雙紋斑螟)、桑螟(Glyphodes pyloalis)、菜心螟(Hellulla midalis)、Marasmia exigua(稻縱捲葉蛾、Rice leaf roller)、豆莢螟 (Marnca testulalis)、棉捲葉野螟蛾(Notarcha derogata)、玉米螟 (Ostrinia fumacalis)、褐翅桿野填蛾(〇3103血5〇&卩111&也)、〇313±^ zaguliaevi(蕗野螟蛾、japanese butter bur borer)、草坪苞蛾 (Parapediasia teterrella)、Pleuroptya mralis(鬱金野模蛾、Bean webworm)、印度穀蛾(Plodia interpuctella)、水稻一點大螟 (Scirpophaga incertulas)、單帶弄蝶(Parnara guttata)、白紋鳳蝶 (Papilio helenus)、Papilio machaon hippocrates(黃鳳蝶、 Swallowtail)、柑桔鳳蝶(Papilio xuthus)、Colias erate poliographus(紋 黃蝶、Oriental clouded yellow)、曰本紋白蝶(Pieris rapae cmcivora)、波紋小灰蝶(Lampides boeticus)、Angerona pranaria(李 141 200836629Cuphodes diospyrosella (persimmon, moth), Phyllonorycter ringoniella (gold, moth, apple leaf miner), Spulerrina astaurota (Pear moth), Phylocnistis citrella, Phyllocnistis toparcha (Acerola moth), Acrolepiopsis Sapporensis (Scallion moth), Acrolepiopsis suzukiella (P. sylvestris), Plutella xylostella, Argyresthia conjugella (Apple fruit moth), Paranthrene regalis (Grape clearwing moth), Synanthedon hector ( Small tree borer, Cherry tree borer, Stathmopodamasinissa, Brachmiatriannulella, Pectinophora gossypiella, Phthorimaea operculella, Carposina niponensis, Peach fruit Moth), Illiberis prnni (apple leaf black-winged moth), Latoia sinica (black-spotted moth), yellow-spotted moth (]\^01^11^£1^^306113), pear moth (7^1* 08(^(161^他¥丨(1(like & also), sa 剌 (Parasa consocia), Scopelodes contracus (姬黑剌), 二化填(Chilo Suppressalis), Cnaphalocrosis medinalis, Conogethes punctiferalis, Diaphania indica, Ectomyelois pyrivorella, Ephestia elutella, Ephestia kuehniella Spotted moth), Etiella zinckenella, Euzophera batangensis, Glyphodes pyloalis, Hellulla midalis, Marasmia exigua (rice leaf roller) , Marnca testulalis, Notarcha derogata, Ostrinia fumacalis, brown-winged wild moth (〇3103血5〇&卩111& also), 〇313±^ Zaguliaevi (japanese butter bur borer), turf moth (Parapediasia teterrella), Pleuroptya mralis (Tujin wild moth, Bean webworm), Plodia interpuctella, Scirpophaga incertulas, Parnara guttata, Papilio helenus, Papilio machaon hippocrates, Swallowtail, Papilio xuthus, Colias erat e poliographus (Oriental clouded yellow), Pieris rapae cmcivora, Lampides boeticus, Angerona pranaria (Li 141 200836629
尺蠖蛾)、瘤尺蠖蛾(Ascotis selenaria)、Biston robustum(褐紋大尺護 蛾)、Cystidia couaggaria(梅尺蠖蛾)、Dendrolimus spectabilis(松枯 葉蛾)、帶紋洸蛾(Malacosoma neustria testacea)、Odonestis prnni japonensis(蘋果枯葉蛾)、大透翅天蛾(Cephonodes hylas)、缺角天 蛾(Acosmeryx castanea)、揚扇舟蛾(Clostera anachoreta)、分月扇舟 蛾(Clostera anastomosis)、蘋掌舟蛾(Phalera flavescens)、曼蠶舟蛾 (Phalerodonata manleyi)、Stauropus fagi persimilis(天社蛾、又#虎 蛾)、茶毒蛾(Euproctis pseudoconspersa)、白紋毒蛾(Euproctis similis)、毒蛾(Euproctis subflava)、舞毒蛾(Lymantria dispar)、旋古 毒蛾(Orgyia thyellina)、美國白燈蛾(Hyphantria cunea)、Spilosoma 111^^11115(桑胡麻斑燈蛾)、大豆擬尺墁(入0&111;110卩11^&&职3{&)、白斑 煩夜蛾(Aedia leucomelas)、切根蟲(Agrotis ipsilon)、蒸菁夜蛾 (Agrotis segetum)、小橋夜蛾(Anomis flava)、橋夜蛾(Anomis mesogona)、豆類黑點銀紋夜蛾(Autographa nigrisigna) '擬尺蠖 (Trichoplusia ni)、番祐夜蛾(Helicoverpa armigera)、亞麻夜蛾 (Helicoverpa assulta) ' Heliothis maritima(詰草蛾、Flux bud worm)、 甘藍夜蛾(Mamestra brassicae)、稻填蛉(Naranga aenescens)、粟夜 蛾(Pseudaletia separata)、稻紫填(Sesamia inferens)、草坪夜盗蟲 (Spodoptera depravata)、甜菜夜蛾(Spodoptera exigua)、斜紋夜蛾 (Spodoptera litura)、Triaena intermedia(蘋果劍紋蛾)、梨劍紋蛾 (Viminia mmicis)、Xestia o nigrum(白紋夜蛾、spotted cutworm)等; 半翅目(HEMIPTERA)、異翅亞目(Heteroptera)之 Megacopta punctatissium(圓樁象、Globular stink bug) 、Carpocoris purpureipennis(紫樁象)、Dolycoris baccarum(斑鬚樁象)、青樁象 (Eurydema pulchrum)、Eurydema rngosum(菜樁象、Cabbage bug)、 圓白星樁象(Eysarcoris guttiger)、Eysarcoris lewisi(大刺白星樁象、 Lewis spined bug)、Eysaxcoris parvus(小刺白星樁象)、白星樁象 (Eysarcoris ventralis)、Glaucias subpunctatus(f^青樁象)、黑條紅樁 象(Graphosoma rubrolineatum)、Halyomorpha mista(臭木樁象、 142 200836629蠖), Ascotis selenaria, Biston robustum, Cystidia couaggaria, Dendrolimus spectabilis, Malacosoma neustria testacea, Odonestis Prnni japonensis (Apple dead leaf moth), Cephonodes hylas, Acosmeryx castanea, Clostera anachoreta, Clostera anastomosis, Phalera Flavescens), Phalerodonata manleyi, Stauropus fagi persimilis, Euproctis pseudoconspersa, Euproctis similis, Euproctis subflava, gypsy moth Lymantria dispar), Orgyia thyellina, Hyphantria cunea, Spilosoma 111^^11115 (Sanghu moth), Soybean stalk (Ins; 111; 110卩11^&& job 3{&), Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Anomis flava, Anomis meso Gona), Autographa nigrisigna, Trichoplusia ni, Helicoverpa armigera, Helicoverpa assulta, Heliothis maritima, Fux bud worm , Maamestra brassicae, Naranga aenescens, Pseudaletia separata, Sesamia inferens, Spodoptera depravata, Spodoptera exigua, twill Spodoptera litura, Triaena intermedia, Viminia mmicis, Xestia o nigrum, spotted cutworm, etc.; Hemiptera (HEMIPTERA), Heteroptera (Heteroptera) Megacopta punctatissium (round pile elephant, Globular stink bug), Carpocoris purpureipennis (purple pile elephant), Dolycoris baccarum (beauty pile elephant), blue pile elephant (Eurydema pulchrum), Eurydema rngosum (vegetable pile image, Cabbage bug ), Eysarcoris guttiger, Eysarcoris lewisi, Lewis spined bug, Eysaxcoris parvus, white star statue Eysarcoris ventralis), Glaucias subpunctatus (f^青青象), Black-streaked red-grass (Graphosoma rubrolineatum), Halyomorpha mista (Smelly Pile, 142 200836629
Brown-marmorated stink bug)、Lagynotomus elongatus(稻樁象、Rice ifiSk bug)、綠樁象(Nezara antennata)、南方綠樁象(Nezara viridula)、Piezodoms hybneri(—字樁象)、小珀樁象(Plautia stali)、 稻黑樁象(Scotinophara lurida)、Starioides iwasakii(岩崎氏樁象)、瘤 緣樁象(Acanthocoris sordidus)、Anacanthocoris striicomis(大虫知蛛緣 樁象)、稻棘緣樁象(Cletus punctiger)、長肩棘緣樁象(Cletus trigonus)、大緣捲象(Molipteryx fiilginosa)、禾蛛緣橋象(Leptocorisa acuta)、Leptocorisa chinensis(蛛虫知緣樁象、Corbett rice bug)、 Leptocorisa oratorius(臺灣檢蛛緣樁象)、點蜂緣樁象(Riptortus clavatus)、Aeschynteles maculatus(姬紅緣樁象)、Liorhyssus hyalinus(透翅姬緣捲象)、小翅長捲象(Cavelerius saccharivorus)、 Macropes obnubilus(細小翅長樁象)、Pachybrachius luridus(葫蘆小 扁長樁象)、Paromius exiguus(黑腳細長樁象)、Togo hemiptems(葫 蘆小翅長樁象)、赤星樁象(Dysdercus cingulatus)、姬赤星樁象 (Dysdercus poecilus)、菊軍配蟲(Galeatus spinifrons)、臺高冠網樁 象(Metasalispopuli)、Stephanitis fasciicarina(樟軍配蟲)、梨冠軍配 蟲(Stephanitis nashi)、杜鵑軍配蟲(Stephanitis pyrioides)、Uhlerites debile (姬軍配蟲)、Uhlerites latius(胡桃軍配蟲)、Adelphocoris lineolatus(鬚長盲樁象、AlMfe plant bug)、黑斑鬚盲樁象 (Adelphocoris triannulatus)、綠麗盲樁象(Apolygus lucomm)、 Apolygus spinolai(黑尾綠盲樁象)、赤星盲樁象(Creontiades pallidifer)、Cyrtopeltis ternmis(煙草盲樁象)、Ectometopterus micantulus(大黑褐盲樁象)、Halticiellus insularis(黑褐盲樁象)、 Heterocordylus flavipes(蘋果黑盲樁象)、Lygus disponsi(捲葉盲樁 象)、Lygus saundersi(斑點盲樁象)、Orthotylus flavosparsus(甜菜盲 樁象)、Stenodema calcaratum(麥盲樁象)、Stenotus binotatus(雙條盲 樁象)、Stenotus mbrovittatus(赤條盲捲象)、Taylorilygus pallidulus(淺紋綠盲樁象)、Trigonotylus coelestialium(赤鬚細綠盲樁 象)等,同翅亞目(Homoptera)之 Graptopsaltria nigrofUscata(油蟬、 143 200836629Brown-marmorated stink bug), Lagynotomus elongatus (Rice ifiSk bug), Nezara antennata, Nezara viridula, Piezodoms hybneri, and small piles Plautia stali), Scotinophara lurida, Starioides iwasakii (Iwasaki pile), Acanthocoris sordidus, Anacanthocoris striicomis, and rice thorns (Cletus punctiger) ), Cletus trigonus, Molipteryx fiilginosa, Leptocorisa acuta, Leptocorisa chinensis, Corbett rice bug, Leptocorisa oratorius Taiwan's checkpoints, Riptortus clavatus, Aeschynteles maculatus, Liorhyssus hyalinus, Cavelerius saccharivorus, Macropes obnubilus Winged long pile elephant), Pachybrachius luridus (Gourd small flat long pile elephant), Paromius exiguus (black foot slender pile image), Togo hemiptems (Gourd small winged long pile elephant), red star Piles (Dysdercus cingulatus), Dysdercus poecilus, Galeatus spinifrons, Metasalispopuli, Stephanitis fasciicarina, Stephanitis nashi , Stephanitis pyrioides, Uhlerites debile, Uhlerites latius, Adelphocoris lineolatus, AlMfe plant bug, Adelphocoris triannulatus, Apolygus lucomm, Apolygus spinolai, Creontiades pallidifer, Cyrtopeltis ternmis (tobacco blind pile), Ectometopterus micantulus (large black-brown pile) Halticiellus insularis (black-brown blind elephant), Heterocordylus flavipes (apple black blind pile), Lygus disponsi (blind blind image), Lygus saundersi (spotted blind elephant), Orthotylus flavosparsus (beet blind pile), Stenodema calcaratum (Silk blind pile elephant), Stenotus binotatus (double blind pile elephant), Stenotus mbrovittatus (red striped blind elephant), Ta Ylorilygus pallidulus (light green blind pile), Trigonotylus coelestialium (red whisker), Ghoptopsaltria nigrofUscata (Homoptera) (oil 蝉, 143 200836629)
Large brown cicada)、Aphxophora costalis(前黃沫蟬)、Aphrophora flaVipes(松沫蟬)、葡萄沫蟬(Aphrophora vitis)、Clovia punctata(雙 點姬長洙蟬)、細沫蟬(Philaenus spumarius)、Bothrogonia japonica(黑 尾大浮塵子)、大浮塵子(Cicadella viridis)、大白葉蜂(Cofana spectra)、Aguriahana quercus(櫟姬浮塵子)、Alnetoidia alneti(赤楊 姬浮塵子)、Apheliona fermginea(掛桔姬浮塵子)、Arboridia apicalis(雙點姬浮塵子)、綠姬浮塵子(Edwardsiana flavescens)、玫 瑰姬浮塵子(Edwardsiana rosae)、Empoasca abietis(松姬浮塵子)、 Empoasca onukii(茶綠姬浮塵子、Tea green leafhopper)、Thaia submfa(稻黃姬浮塵子)、Zyginella citri(蜜柑姬浮塵子)、雙點浮塵 子(Macrosteles fascifrons)、黑尾浮塵子(Nephotettix cincticeps)、 Nephotettix nigropictus(黑條黑尾浮塵子)、Nephotettix virescens(臺 灣黑尾浮塵子)、Orientus ishidai(蘋果斑紋浮塵子)、電光浮塵子 (Recilia dorsalis)、Sorhoanus tritici(麥浮塵子)、Speusotettix subfUsculus(赤揚長浮塵子)、稻斑飛蝨(Laodelphax striatellus)、稻 褐飛蝨(Nilaparvata lugens)、Numata muiri(甘蔗淡色飛蝨、Pale sugarcane planthopper)、玉米飛蝨(Peregrinus maides)、Perkinsiella saccharicida(黑斑角飛蝨、Sugarcane planthopper)、稻白背飛蝨 (Sogatella fUrcifera)、Sogatella panicicola(稗飛蝨)、Anomoneura mori(桑木蝨、Mulberry sucker)、Calophya nigridorsalis(黑背姬木 蟲)、柑桔木蟲(Diaphorina citri)、黃檀木盘(Mesohomotoma camphorae)、Psylla abieti(椴松木蝨)、psylla aM(赤揚木蝨)、Psylla jamatonica(大和木兹)、Psylla mali (蘋果木兹)、Psylla malivorella(蘋 果黑木蝨)、Psyllapyrisuga(梨木蝨、Pear sucker)、Psylla tobirae(海 桐木蝨、Tobera sucker)、Trioza camphorae(樟尖木蝨、Camphor sucker)、Trioza quercicola(栗尖木蝨)、柑桔刺粉蝨(Aleurocanthus spinifcms)、Aleurolobiis taonabae(葡萄粉蝨、Grape whitefly)、菸草 粉蝨(Bemisia tabaci)、柑桔雙孔粉蝨(Dialeurodes citri)、溫室粉蝨 (Trialeurodes vapomriomm)、銀葉粉蝨田61]^1&&租61^&出)、葡萄 144 200836629Large brown cicada), Aphxophora costalis (pre-yellow), Aphrophora flaVipes, Aphrophora vitis, Clovia punctata, Philaenus spumarius, Bothrogonia japonica ( Black-tailed scorpion), Cicadella viridis, Cofana spectra, Aguriahana quercus, Alnetoidia alneti, Apheliona fermginea, Arboridia apicalis Double-pointed Jifu dust), Edwardsiana flavescens, Edwardsiana rosae, Empoasca abietis, Empoasca onukii (Tea green leafhopper), Thaia submfa (rice magnolia) ), Zyginella citri, Honeysteles fascifrons, Nephotettix cincticeps, Nephotettix nigropictus (Neurotettix virescens), Orientus ishidai (Apple striated) Floating dust), electro-optical dust (Recilia dorsa Lis), Sorhoanus tritici, Speusotettix subfUsculus, Laodelphax striatellus, Nilaparvata lugens, Numata muiri, Pale sugarcane planthopper, Corn planthopper (Peregrinus maides), Perkinsiella saccharicida (Sweet cane planthopper), Sogatella fUrcifera, Sogatella panicicola, Anomoneura mori, Mulberry sucker, Calophya nigridorsalis Diaphora citri, Diaphorina citri, Mesohomotoma camphorae, Psylla abieti, psylla aM, Psylla jamatonica, Psylla mali Apple Woods, Psylla malivorella, Psyllapyrisuga, Pear sucker, Psylla tobirae, Tobera sucker, Trioza camphorae, Trioza quercicola Sharpwood), Aleurocanthus spinifcms, Aleurolobiis taonabae (Grape meal, Gr Ape whitefly), Bemisia tabaci, Dialeurodes citri, Trialeurodes vapomriomm, Silver leaf powder 61]^1&&rent 61^&out) Grape 144 200836629
根瘤呀(Viteus vitifolii)、Aphidounguis mali(蘋果根財)、Eriosoma ianigerum(蘋果綿財、Wooly apple aphid)、甘嚴根綿虫牙(Geoica lucifuga)、鬚長財蟲(Acyrthosiphon pisum)、柑桔捲葉辑(Aphis citricola)、黑豆虫牙(Aphis craccivora)、Aphis farinose yaxiagicola(杉p 虫牙)、棉騎(Aphis gossypii)、馬鈴薯財(Aulacorthum solani)、舌尾虫牙 (Brachycaudus helichrysi)、菜虫牙(Brevicoryne brassicae)、鬱金香根 虫牙(Dysaphis tulipae)、Euceraphis punctipeimis(禅吹棉孩王虫牙)、才兆粉虫牙 (Hyaloptems prnni)、偽菜財(Lipaphis erysimi)、光褐菊虫牙 (Macrosiphoniella sanbomi)、大戟長管財(Macrosiphum euphorbiae)、Megoura crassicauda(蠶豆長鬚財、Vetch aphid)、 Melanaphis siphonella(梨小吹棉財)、蘋果瘤財(Myzus malisuctus)、 梅瘤虫牙(Myzus mumecola)、桃虫牙(Myzus persicae)、蔥並虫牙 (Neotoxoptera formosana)、Ovatus malicolens(蘋果綠財)、蓮薇虫牙 (处(^&1〇8丨01111111113^[^1^6&6)、稻麥財(仙(^&1〇81口1皿11卩&出)、紅腹稻 根財(又長毛角虫牙、Rhopalosiphum mfiabdominalis)、Sappaphis piri(梨圓虫牙)、梨二叉虫牙(Schizaphis piricola)、小麥長角騎牌(如〇11 akebiae)、月季虫牙(Sitobion ibarae)、小桔虫牙(Toxoptera aurantii)、大 拮虫牙(Toxoptera citricidus)、Tuberocephalus momonis(桃瘤虫牙)、白尾 紅虫牙(Uloleucon formosanum)、麥二叉財(Schizaphis graminum)、 Dosichacorpulenta(大草鞋介殼蟲)、吹棉介殼蟲(Icerryapurchasi)、 Crisicoccus matsumotoi(松本粉介殼蟲)、Crisicoccus pini(松粉介殼 蟲、Japanese pine mealybug)、Dysmicoccus wistariae(梨粉介殼蟲)、 掛桔粉介殼蟲(Planococcus citri)、臀紋粉介殼蟲(Planococcus kraunhiae)、桔臀粉介殼蟲(又橘小粉介殼蟲、Pseudococcus citriculus)、康氏粉介殼蟲(Pseudococcus comstocki)、角躐介殼蟲 (Ceroplastesceriferus)、紅犧介殼蟲(Ceroplastesmbens)、柑桔介殼 蟲(Coccus discrepans)、柑桔扁堅介殼蟲(Coccus hesperidum)、 Coccus pseudomagnoliamm(柑桔堅介殼蟲)、Ericerus pela(斑葉女貞 蠟介殼蟲)、Lecanium comi(挾木堅介殼蟲)、黑光堅介殼蟲 145 200836629 (Lecaniumpersicae)、Pulvinariaaurantii(蜜柑綿介殼蟲)、Pulvinaria citricola(蜜柑姬綿介殼轰)、Pulvinariakuwacola(桑姬介殼蟲)、工背 硬介殼蟲(Saissetia oleae)、Andaspis kashicola(柑桔介殼蟲)、柑紅 臀圓盾介殼蟲(Aonidiella aurantii)、柑黃臀圓盾介殼蟲(Aonidiella citrina)、淡薄圓盾介殼蟲(Aspidiotus destructor)、白圓盾介殼蟲 (Aspidiotus hederae)、褐圓介殼蟲(Chrysomphalus ficus)、梨齒盾介 殼蟲(Comstockaspis periniciosa)、Duplaspidiotus clviger(黑堅圓介殼 蟲)、掛紫螺介殼蟲(Lepidosaphes beckii)、榆螺介殼蟲(1^>丨(1〇8&卩1^ ulπli)、日本長片盾介殼蟲(Lopholeucaspisjaponica)、ParlatoΓeopsis pyri(梨黑星介殼蟲)、山茶片盾介殼蟲(Parlatoria camelliae)、茶黑 星介殼蟲(Parlatoriatheae)、黑片盾介殼蟲(Parlatoriaziziphi)、柑桔 並盾介殼蟲(Pinnaspis aspidistrae)、網背盾介殼蟲(Pseudaonidia duplex)、茶圓介殼蟲(Pseudaonidia paeoniae)、桑擬白輪盾介殼蟲 (Pseudaulacaspis pentagona)、桑擬輪盾介殼蟲(Pseudaulacaspis prunicola)、箭頭介殼蟲(Unaspis yanonensis)等;曱蟲;目 (COLEOPTERA)之 Adoretus tenuimaculatus(茶色金龜)、金銅金龜 (Anomala cuprea)、姬金龜(Anomala mfocuprea)、花金龜(Eucetonia pilifera)、綠花金龜(Eucetonia roelofsi)、茶色長金龜(Heptophyla picea)、Melolontha japonica(粉吹金龜)、盤金龜(Mimela splendens)、 小綠花金龜(Oxycetonia jucunda)、曰本豆金龜(Popillia japonica)、 Anthrenus verbasci(姬圓鰹節蟲)、Attage 皿 s unicolor japonicus (姬鰹 節蟲)、於曱蟲(Lasioderma serricome)、Lyctus bmnneus(扁食薪蟲)、 米露尾蟲(Carpophilus dimidiatus)、Carpophilus hemiptems(乾果金 龜、Dried fruit beetle)、Epilachna vigintioctomaculata(大二十八星瓢 蟲)、二十八星瓢蟲(Epilachna vigintioctopunctata)、菜豆瓢蟲 (Epilachna varivestis)、Alphitobms laevigatus(姬擬粉蟲)、Neatus picipes(大點擬粉蟲)、Palorns ratzeburgii(姬擬穀盜)、小姬擬穀盜 (Palorns subdepressus)、茶色偽步行蟲(Tenebrio molitor)、(赤)擬榖 盜(Tribolium castaneum)、扁擬穀盜(Tribolium confusum)、豆宪菁 146 200836629Roots vitifolii, Aphidounguis mali, Eriosoma ianigerum, Geoica lucifuga, Acyrthosiphon pisum, citrus roll leaf Aphis citricola), Aphis craccivora, Aphis farinose yaxiagicola, Aphis gossypii, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, tulip Dysaphis tulipae, Euceraphis punctipeimis, Hyaloptems prnni, Lipaphis erysimi, Macrosiphoniella sanbomi, Macrosiphum Euphorbiae), Megoura crassicauda (Vecchio long hair, Vetch aphid), Melanaphis siphonella (Pear Blowing cotton), Apple (Myzus malisuctus), Myzus mumecola, Myzus persicae, onion Neotoxoptera formosana, Ovatus malicolens, and lotus root teeth (^&1〇8丨011111 11113^[^1^6&6), Rice Maicai (Xian (^&1〇81 口一皿11卩&出), Red-bellied rice roots (also Longhorn hornworm teeth, Rhopalosipum mfiabdominalis), Sappaphis piri (Pear roundworm teeth), Schizaphis piricola, wheat longhorn riding cards (such as 〇11 akebiae), Sitobion ibarae, Toxoptera aurantii, Toxoptera citricidus, Tuberocephalus momonis, Ulodeux formosanum, Schizaphis graminum, Dosichacorpulenta, Icerryapurchasi, Crisicoccus matsumotoi, Crisicoccus pini (Japanese pine mealybug), Dysmicoccus wistariae (Pear powder scale insect), Planococcus citri, Planococcus kraunhiae, Orange hip powder scale insect (also orange) Pseudococcus citriculus, Pseudococcus comstocki, Ceroplastes ceriferus, Ceroplastesmbens, citrus crust Coccus discrepans, Coccus hesperidum, Coccus pseudomagnoliamm, Ericerus pela, Lecanium comi, black light Scale insect 145 200836629 (Lecaniumpersicae), Pulvinariaaurantii (Prunus persicae), Pulvinaria citricola (Prunus sylvestris), Pulvinariakuwacola (Sangji scale), Saissetia oleae, Andaspis kashicola (citrus) Scale insects, Aonidiella aurantii, Aonidiella citrina, Aspidiotus destructor, Aspidiotus hederae, brown round Chrysomphalus ficus, Comstockaspis periniciosa, Duplaspidiotus clviger, Lepidosaphes beckii, snail scales (1^>丨(1〇) 8&卩1^ ulπli), Japanese long-stem worm (Lopholeucaspisjaponica), ParlatoΓeopsis pyri (Pear black star scale insect), Camellia Shield scale insect (Parlato Ria camelliae), Parlatoriatheae, Parlatoriaziziphi, Pinnaspis aspidistrae, Pseudaonidia duplex, Pseudaonidia paeoniae ), Pseudaulacaspis pentagona, Pseudaulacaspis prunicola, Unaspis yanonensis, etc.; aphids; COLEOPTERA Adoretus tenuimaculatus (brown tortoise), gold and copper Anomala cuprea, Anomala mfocuprea, Eucetonia pilifera, Eucetonia roelofsi, Heptophyla picea, Melolontha japonica, Mimela splendens , Oxycetonia jucunda, Popillia japonica, Anthrenus verbasci, Attage s unicolor japonicus, Lasioderma serricome, Lyctus bmnneus Flat food worm), Carpophilus dimidiatus, Carpophilus hemiptems (dry fruit golden tortoise, Dried fru It beetle), Epilachna vigintioctomaculata (Big 28), Epilachna vigintioctopunctata, Epilachna varivestis, Alphitobms laevigatus, Neatus picipes Mealworms, Palorns ratzeburgii, Palorns subdepressus, Tenebrio molitor, Tribolium castaneum, Tribolium confusum ), Bean Xianjing 146 200836629
(Epicauta gorhami)、黃斑天牛(Aeolesthes chrysothrix)、白斑星天牛 (Anoplophoramalasiaca)、松斑天牛(Monochamus altematus)、黃星 天牛(Psacothea hilaris)、Xylotrechus pyrrhodems(葡萄虎斑天牛)、 青帶天牛(Xystrocera globosa)、Acanthoscelides obtectus(菜豆象、 Bean weevil)、綠豆象(Callosobmchus chinensis)、Callosobmchus maculatus(四紋豆象)、黃守瓜(Aulacoptiora femoralis)、Basilepta balyi(茶色猿葉蟲)、Cassida nebulosa (小龜金花蟲)、Chaetocnema concinna(甜菜跳金花蟲)、Colasposoma dauricum(甘藷猿金花蟲、 Sweetpotato leaf beetle)、Crioceris quatuordecimpunctata(十四星長頸 金花蟲)、Donaciaprovosti(稻食根金花蟲)、Linaeidea aenea(琉璃金 花蟲)、Luperomorpha tunebrosa(黃腳蚤金花蟲)、]\^(1;>11也 nigrobilineata(雙條姬金花轰)、稻負泥蟲(Oulema oryzae)、Pagria signata(姬黃翅猿葉轰)、(小)猿葉蟲(Phaedon brassicae)、黃條葉蚤 (Phyllotreta striolata)、Leptinotarsa decemlineata(科羅拉多金花蟲)、 Diabrotica sp·(玉米根金花蟲類)、Involvulus cupreus(梅短截象轰、 Plum borer)、Rhynchites heros(桃短截象蟲、Peach curculio)、甘薯 蟻象(Cylas formicarius)、Anthonomus pomomm(蘋果花象蟲、Apple blossom weevil)、Ceuthorhyncliidius albosuturalis(蘿蔔猿象蟲)、 Curculio sikkimensis(栗 i| 象鼻蟲、Chestnut curculio)、稻象鼻蟲 (Echinocnemus squameus)、Euscepes postfasciatus(甘藷象鼻蟲)、 Hypera nigrirostris(詰草硝象鼻蟲、Lesser clover leaf weevil)、苜蓿 象鼻蟲(Hyperapostica)、水稻水象鼻蟲(Lissorhoptms orizophilus)、 蔬菜象鼻蟲(Listroderes costirostris)、Phyllobius armatus(蘋果粉吹象 蟲)、Sitona japonicus(小粉吹象蟲)、棉鈴象鼻蟲(Anthonomus grandis)、米象(Sitophilus oryzae)、玉米象(§itophilus zeamais)、草 皮步行象鼻蟲(Sphenophrus venatus vestitus)、松食蟲(Tomicus piniperda)等;纓趨目(THYSANOPTERA)之黃呆薊馬(Anaphothrips obscums)、芒薊馬(Chirothrips manicatus)、三輪薊馬(Dendrothrips minowai)、臺灣花薊馬(Frankliniella intonsa)、百合黃薊馬 147 200836629 (Frai止liniella lilivora)、變葉木薊馬(Heliothrips haemorrhoidalis)、菊 花薊馬(Microcephalothrips abdominalis)、Mycterothrips glycines(大 豆薊馬)、桑薊馬(Pseudodendrothrips mori)、小黃薊馬(Scirtothrips dorsalis)、赤帶薊馬(Selenothrips mbrocinctus)、稻薊馬 (Stenchaetothrips biformis)、青蔥薊馬(Thrips alliomm)、花色箣馬 (Thrips coloratus)、淡色薊馬(Thrips flavus)、花薊馬(Thrips hawaiiensis)、Thrips nigropilosus(黑毛花薊馬)、南黃薊馬(Thrips palmi)、西方花薊馬(Franklinella occidentalis)、日本煙草薊馬(Thrips setosus)、唐 g 蒲薊馬(Thrips simplex)、蔥薊馬(Thrips tabaci)、尖毛 薊馬(Haplothrips aculeatus)、中國薊馬(Haplothrips chinensis)、 Haplothrips kurdjumovi(花管薊馬)、Haplothrips niger(詰草管薊 馬)、Leeuwenia pasanii(椎木長尾管薊馬)、Liothrips floridensis(樟 管薊馬)、百合管莉馬(Liothrips vaneeckei)、Litotetothrips pasaniae(椎木圓管薊馬)、Ponticulothrips diospyrosi(柿管薊馬)等; 直翅目(ORTHOPTERA)之美洲蜚蠊(Periplaneta americana)、黑蜚蠊 (Periplaneta fuliginosa)、大和蜚蠊(Periplaneta japonica)、德國姬蠊 (Blattella germanica)、叉紋姬蠊(Blattella lituricollis)、 Homorocoryphus jezoensis(姬草螽蜇)、Homorocoryphus lineosus(草 螽暂)、螻蛄(Gryllotalpa sp·)、小稻竣(Oxya hyla intricata)、Oxya yezoensis(小翅稻蝗)、Locusta migratoria(東亞飛蝗)等;雙翅目 (DIPTERA)之 Tipula aino(切蛆大蚊)、Bradysia agrestis(小黑翅茸 繩)、Asphondylia sp·(大豆英瘤繩)、瓜實繩(Dacus cucurbitae)、東 方果實繩(Dacus dorsalis)、Dacus tsmieonis(蜜柑實繩)、Rhacochlaena japonica(櫻桃實蠅、Japanese cherry fruit fly)、Hydrellia griseola(稻 姬潛葉繩、Smaller rice leaf miner)、稻心繩(Hydrellia sasakii)、 Drosophila stizukii(櫻桃果蠅、Cherry drosophila)、Chlorops oryzae(稻桿潛繩)、Meromyza nigriventris(麥桿潛繩)、Agromyza oryzae(稻葉潛繩、Rice leaf miner)、韭潛繩(Chromatomyia horticola)、讀篇斑潛繩(Liriomyza bryoniae)、蔥潛蠅(Liriomyza 148 200836629 chinensis)、非洲雨斑潛繩(Liriomyza trifolii)、蔬菜斑潛繩(Liriomyza sativae)、南美斑潛蠅(Liriomyza huidobrensis)、Delia antiqua(洋蔥 潛繩)、種繩(Delia platura)、Pegomya cunicularia(甜菜潛繩)、Phormia regina(黑麗_绳)、家繩(Musca domestica)、Culex pipiens pallens(赤家 蚊)、Anopheles sinensis(中國翅斑蚊)、Aedes albopictus(白線斑 蚊)、地下家蚊(Culex pipiens molestus)等;膜翅目 (HYMENOPTERA)之蕪菁葉蜂(Athalia japonica)、Athalia rosae mficomis(蕪菁葉蜂、Cabbage sawfly)、Arge mali (蘋果葉蜂)、玫 瑰三節葉蜂(Arge pagana)、Dryocosmus kuriphilus(栗瘤蜂、Chestnut gall wasp)、曰本山蟻(Formica japonica)等;蜱蜗目(ACARINA)之 Polyphagotarsonemus latus(茶細蜗)、仙客來細蜗(Steneotarsonemus pallidus )、Tarsonemus waitei(細腳細蜗)、Pyemotes ventricosus(兹 狀蒲蟎)、Penthaleus major (麥蜗)、利未氏偽葉蝠(Brevipalpus lewisi)、錫蘭偽葉蜗(Brevipalpus obovatus)、鳳梨姬葉瞒 (Dolichotetranyclms floridanus)、Tenuipalpus zhizliilashviliae(柿姬葉 蜗)、紫紅偽葉蜗(Brevipalpus phoenicis)、Tuckerella pavoniformis(長 鬚葉蜗)、Bryobiapraetiosa(三葉草葉蜗)、Bryobiarubrioculiis(偽三 葉草葉蜗)、Eotetranychus boreus(杏葉蟎)、Eotetranychus geniculatus(陸奥葉蜗)、Eotetranychus pmni(栗葉瞒)、Eotetranychus sexmanaculatus(河野氏白葉瞒)、Eotetranyclius smithi(史密斯葉 蜗)、Eotetranychus 皿catus(胡桃葉蜗)、Oligonyclms hodoensis(杉葉 蜗)、Oligonychus ilicis(小瘤葉蟎)、Oligonychus karamatus(落葉松 葉蜗)、柑桔葉编(Panonychus citri)、Panonychus ulmi(蘋果葉蜗)、 赤葉蜗(Tetranychus cinnabarinus)、神澤葉蜗(Tetranychus kanzawai)、二點葉虫高(Tetranyclms urticae)、Tetranyclms viennensis(櫻 桃葉蜗)、Acaphylla theae(茶長錄蜱)、Aceria tulipae(鬱金香銹蜱)、(Epicauta gorhami), Aeolesthes chrysothrix, Anoplophoramalasiaca, Monochamus altematus, Psacothea hilaris, Xylotrechus pyrrhodems, and green-eared beetles (Xystrocera globosa), Acanthoscelides obtectus (Bean weevil), Callobemchus chinensis, Callosobmchus maculatus, Aulacoptiora femoralis, Basilepta balyi, Cassida nebulosa (Small Turtle), Chaetocnema concinna, Colasposoma dauricum (Sweet potato, Sweetpotato leaf beetle), Crioceris quatuordecimpunctata (Fourteen-star long-necked golden flower worm), Donaciaprovosti (rice root) Golden flower worm), Linaeidea aenea (Glass glabrata), Luperomorpha tunebrosa (Yellowfoot golden flower worm),]\^(1;>11 also nigrobilineata (Double Jellyfish), rice worm (Oulema oryzae) ), Pagria signata, Phaedon brassicae, Phyllotreta striolata Leptinotarsa decemlineata (Colorado flower bud), Diabrotica sp. (corn root genus), Involvulus cupreus (Plum chill, Plum borer), Rhynchites heros (Peach curculio), sweet potato ant (Cylas formicarius), Anthonomus pomomm (Apple flower weevil, Ceuthorhyncliidius albosuturalis), Curculio sikkimensis (chestnut i, weevil, Chestnut curculio), rice weevil (Echinocnemus squameus), Euscepes postfasciatus, Hypera nigrirostris (Lesser clover leaf weevil), Hyperapostica, Lisorhoptms orizophilus, Vegetable Weevil (Listroderes costirostris) ), Phyllobius armatus, Sitona japonicus, Anthonomus grandis, Sitophilus oryzae, §itophilus zeamais, turf walking trunk Sphenophrus venatus vestitus, Tomicus piniperda, etc.; yellow stagnation of THYSANOPTERA (Anaphothrips obscums), Chirothrips manicatus, Dendrothrips minowai, Frankliniella intonsa, Lily yellow horse 147 200836629 (Frai linliella lilivora), Heliothrips haemorrhoidalis ), Microcephalothrips abdominalis, Mycterothrips glycines, Pseudodendrothrips mori, Scirthothrips dorsalis, Selenothrips mbrocinctus, Stendchaetothrips biformis ), Thrips alliomm, Thrips coloratus, Thrips flavus, Thrips hawaiiensis, Thrips nigropilosus, Southern yellow horse (Thrips) Palmi), Franklinella occidentalis, Thrips setosus, Thrips simplex, Thrips tabaci, Haplothrips aculeatus, Chinese cockroach Horse (Haplothrips chinensis), Haplothrips kurdjumovi (flower tube hummer), Haplothrips niger (诘草管蓟马), Leeuw Enia pasanii (Vertebra long-tailed hummer), Liothrips floridensis (Lithrips vaneeckei), Lithrips vaneeckei, Litotetothrips pasaniae (Vertebrate round hummer), Ponticulothrips diospyrosi (Persimmon tube hummer), etc.; ORTHOPTERA American Periplaneta americana, Periplaneta fuliginosa, Periplaneta japonica, Blattella germanica, Blattella lituricollis, Homorocoryphus jezoensis Grasshopper), Homorocoryphus lineosus, grasshopper (Gryllotalpa sp.), Oxya hyla intricata, Oxya yezoensis (small-winged rice blast), Locusta migratoria (East Asian locust), etc.; DIPTERA) Tipula aino, Bradysia agrestis, Asphondylia sp., Dacus cucurbitae, Dacus dorsalis, Dacus tsmieonis (Sweet mandarin rope), Rhacochlaena japonica (Cherry fruit fly, Japanese cherry fruit fly), Hydrellia griseola (rice stalk leaf, Smaller rice leaf Miner), Hydrellia sasakii, Drosophila stizukii, Cherryops oryzae, Meromyza nigriventris, Agromyza oryzae, rice leaf miner ), Chromatomyia horticola, Liriomyza bryoniae, Liriomyza 148 200836629 chinensis, Liriomyza trifolii, Liriomyza sativae, South America Liriomyza huidobrensis, Delia antiqua, onion rope, Delia platura, Pegomya cunicularia, Phormia regina, Musca domestica, Culex pipiens pallens (Ajiao sinensis), Anopheles sinensis (Chinese winged mosquito), Aedes albopictus (white-spotted mosquito), underground mosquito (Culex pipiens molestus), etc.; Hymenoptera (HYMENOPTERA), Athalia japonica, Athalia rosae Mficomis (Chamboto sawfly, Arge mali), Arge pagana, Dryocosmus kuriphilus (Chestnut bee, Chestnut gall was p), Formica japonica, etc.; Polyphagotarsonemus latus (tea snail) of ACARINA, Steneotarsonemus pallidus, Tarsonemus waitei, Pyemotes ventricosus P. sylvestris, Penthaleus major, Brevipalpus lewisi, Brevipalpus obovatus, Dolichotetranyclms floridanus, Tenuipalus zhizliilashviliae , Bluvipalpus phoenicis, Tuckerella pavoniformis, Bryobia praetiosa, Bryobiarubrioculiis, Eotetranychus boreus, Eotetranychus geniculatus, Eotetranychus pmni, Eotetranychus sexmanaculatus, Eotetranyclius smithi, Eotetranychus catus, Oligonyclms hodoensis, Oligonychus ilicis , Oligonychus karamatus (larch leaf worm), citrus leaf (Panonychus citr i), Panonychus ulmi (Apple leaf worm), Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranyclms urticae, Tetranyclms viennensis (cherry leaf worm), Acaphylla theae (tea long) Recorded), Aceria tulipae (Tulip rust),
Aculops pelekassi(蜜柑錄蜱)、Aculus fockeui(桃銹蜱)、Aculus schleclitendali(顏果錢蜱)、紫銹蜱(Calacarus carinatus)、 Calepitrimems vitis(葡萄銹蜱)、Epitrimems pyri(梨錄蜱)、Eriophyes 149 200836629Aculops pelekassi, Aculus fockeui, Aculus schleclitendali, Calacarus carinatus, Calepitrimems vitis, Epitrimems pyri, Eriophyes 149 200836629
chibaensis(梨偽錄蜱)、Acarns siro(粗足粉蜗)、Aleuroglyphus ovatus(麥粉蜗)、羅賓根蜗(Rhizoglyphus robini)、長毛根瞒 (Tyrophagus putrescentiae)、熱帶鼠恙蟲(Omithonyssus bacoti)、紅 恙蟲(Leptotrombidium akamushi)、盾恙蟲(Leptotrombidiiim scutellaris)、粗毛恙蟲(Leptotrombidium pallidum)等;墊刃線蟲目 (TYLENCHIDA)之腫瘿線蟲(Anguina agrostis)、小麥腫癭線蟲 (Anguinatritici)、馬鈴薯腐敗線蟲(Ditylenchus destructor)、於草矮 化線蟲(Tylenchorhynchus claytoni)、水稻矮化線蟲 (Tylencliorhynchus martini)、矮化線蟲屬(Tylenchorhynchus sp·)、 Hirschmanniella imamuri(今村穿根線蟲)、水稻穿根線蟲 (Hirschmanniella oryzae)、南方根腐線蟲(Pratylenclms coffeae)、 Pratylenchus convallariae(鈐蘭根腐線蟲)、Pratylenchus fallax(菊根 腐線蟲)、茶根腐線蟲(Pratylenchus loosi)、Pratylenchus neglectus(麥 根腐線蟲)、北方根腐線蟲(Pratylenchus penetrans)、根腐線蟲屬 (Pratylenchus sp·)、螺旋線蟲(Helicotylenclms dihystera)、 Helicotylenchus erythrinae(茶螺旋線蟲)、螺旋線蟲屬 (Helicotylenchus sp.)、矛線蟲屬(Hoplolaimus sp·)、腎形線轰 (Rotylenchulus reniformis)、卡羅萊納螺旋線蟲(Scutellonema brachyumm)、Bidera avenae(麥包囊線蟲)、仙人掌包囊線蟲 (Cactodera cacti)、Cryphodera sp.(偽包囊線蟲屬)、Globodera rostochiensis(馬鈴薯包囊線蟲)、曰本包囊線蟲(Heterodera elachista)、大豆包囊線蟲(Heterodera glycines)、三葉草包囊線轰 (Heterodera trifolii)、花生根瘤線蟲(Meloidogyne arenaria)、山茶根 瘤線蟲(Meloidogyne camelliae)、草皮根瘤線蟲(Meloidogyne graminis)、北方根瘤線蟲(Meloidogyne hapla)、南方根瘤線蟲 (Meloidogyne incognita)、根瘤線蟲屬(Meloidogyne sp·)、柑桔線蟲 (Tylenchulus semipenetrans)、Aphelenchus avenae(偽根腐線蟲)等; 矛線蟲目(DORYLAIMIDA)之水稻矮化線蟲(Longidoms martini)、 針線蟲屬(Longidoms sp.)、Xiphinema americanum(美國大劍線 150 200836629 蟲)、劍線蟲屬(Xiphinema sp·)、殘根線蟲屬(Trichodoms sp.)等;總 尾目(THYSANURA)之毛衣魚(Ctenolepisma villosa)、衣魚(Lepisma saccharina)、銀魚(Thermobiadomestica)等;等翅目(ISOPTERA)之 截頭堆沙白議(Cryptotermes domesticus)、家白蟻(Coptotermes formosanus)、大和白蟻(Reticulitermes speratus)、臺灣白蟻 (Odontotermes formosanus)等;喷蟲目(PSOCOPTERA)之書兹(又穀 粉茶姓蟲、Liposcelis bostrychophilus)等;蚤目(SIPHONAPTERA) 之狗蚤(Ctenocephalids canis)等;蝨目(ANOPLURA)之體兹Chibaensis (Pear Pseudomonas), Acarns siro (African worm), Aleuroglyphus ovatus (Rizoglyphus robini), Rhizoglyphus robini, Tyrophagus putrescentiae, Omithonyssus bacoti , Leptotrombidium akamushi, Leptotrombidiiim scutellaris, Leptotrombidium pallidum, etc.; Anguina agrostis, Anguinatritici, TYLENCHIDA Ditylenchus destructor, Tylenchorhynchus claytoni, Tylencliorhynchus martini, Tylenchorhynchus sp., Hirschmanniella imamuri, root-rooted nematode (Hirschmanniella oryzae), Pratylenclms coffeae, Pratylenchus convallariae, Pratylenchus fallax , Northern root rot nematode (Pratylenchus penetrans), root rot line Genus (Pratylenchus sp.), Helicotyllenclms dihystera, Helicotylenchus erythrinae, Helicotyllenchus sp., Hoplolaimus sp., Rotylenchulus reniformis, card Scutellonema brachyumm, Bidera avenae, Cactodera cacti, Cryphodera sp., Globodera rostochiensis, scorpion Heterodera elachista, Heterodera glycines, Heterodera trifolii, Meloidogyne arenaria, Meloidogyne camelliae, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne sp., Tylenchulus semipenetrans, Aphelenchus avenae, etc.; DORYLAIMIDA Rice dwarf nematode (Longidoms martini), needle Longidoms sp., Xiphinema americanum (American Great Sword line 150 200836629 insect), Xiphinema sp., Trichodoms sp., etc.; THYSANURA sweater fish (Ctenolepisma) Villosa), Lepisma saccharina, silverfish (Ermobiadomestica), etc.; Cryptotermes domesticus, Coptotermes formosanus, Reticulitermes speratus, Taiwan Termites (Odontotermes formosanus), etc.; PSOCOPTERA's book (also known as the powdered tea, Liposcelis bostrychophilus), etc.; SIPHONAPTERA's dog (Ctenocephalids canis), etc.; ANOPLURA
(Pediculus humanus humanus)等;節足動物門唇足綱(CHILOPODA) 之蚰挺(Thereuronema tuberculata)等;節足動物門倍足綱 (DIPLOPODA)之雅酸帶馬陸(Oxidus gracilis)等;軟體動物門 (MOLLUSCA)之雙線链蝓(Incilaria bilineata)等。 本發明之殺蟲組成物中對防治害蟲有效之化合物含量,通常 於粉劑為0.5〜20重量%,乳劑為5〜50重量%,可濕性粉劑為 〜90重量%,粒劑為〇·ΐ〜2〇重量%,水懸劑為1〇〜9〇重量0/〇。 另一方面,各劑型之擔體1,通常粉劑為〜99重量%,乳劑為 =〜95重量%,可濕性粉劑為10〜90重量%,粒劑為8〇〜99重 量^,水懸劑為10〜90重量%。又,輔助劑量通常粉劑為〇1〜2〇 重量%,乳劑為1〜20重量%,可濕性粉劑為〇1〜2〇重量%, 劑為0·1〜20重量%,水懸劑為〇丨〜沈重量%。 ’ 藉由將本發明之殺蟲組成物施用於農業植物之收獲物 穫物保射所發生之害蟲。亦即,將本發明之 ^或用水稀釋或懸浮狀態,以防治害蟲有效量對 = 穫物或農業植物收穫物之保存場所進行喷佈、塗沫、Ά收 粉衣H醜或加壓注入等收穫後___)處理即^ 辰業植物收穫物可舉例如水稻、大麥麥 燕麥、婉豆、菜豆、奴、較麵ibem、m bean^ pequxa bean > white bean ^ #-] .^(Lima bean) ^ . ^ ^ ^ $ . „^nectarine) ^ ^ ^ ^ s^; 151 200836629 夏撥(Natsudaidai)、溫州橘、錯橘(Sudachi)、酸撥、Cabos 橘(CWms 、莱姆(Lime)、檸檬、枇杷、榲棹(Quince、 Μ/⑽职)、蘋果、梨、洋梨、酪梨、奇異果、番石榴、椰棗、鳳梨、 百香果、香蕉、木瓜、棣果、草每、蔓越莓、卵越橘、 ^zcdm·麵ovfl加m)、黑莓、藍莓、柿、西瓜、葡萄、香瓜、洋香瓜、 無青、花椰菜、甘藍、蘿蔔、白菜、小松菜(油菜的1變種、食用 油菜)、水芥或西洋水芹(cresson、又waterCress)、羽衣甘藍或芥藍 (kak)、辣根(又西洋山葵)、紅皮蘿蔔(radish)、綠花椰菜作^沉⑺抝、 甘藷、萄篛根、芋頭、馬铃薯、南瓜、胡瓜、越瓜(Cmc_舰/〇慨 ⑽麵⑽)、朝鮮薊(artich〇ke)、苦苣/菊萵苣(Endive)、牛蒡、. 21lTfy) f TtT ^1' ^ ^ ^«'' ^風卓(P_P)、香序、番霖、祐子、甜椒、蘆筒、洋苗、大 士、分,历·窗細、曰本慧的一變種)、毛豆、秋▲、甘藉、 I、、,二絲:未成,豆、未成熟碗豆、油種子(胡麻、油菜 定可可豆、咖难豆、茶、啤酒花㈣等,但本發 種子奸,能社在植物 物以原形態或以水等適當稀釋或‘之'/離將本^明,蟲組成 效之量在植物種子或植物種子之保存於害蟲防治有 布、,泡、粉衣或燻煙燻蒸等處理即|。’貝施噴佈、塗抹、塗 藉由將本發明之殺蟲組成物適用於处 播種後於植物產生之害蟲造成室、物種子,此預防由於在 有效之量在祕種’輯於害蟲防治 塗布、浸泡、粉衣等處理,以二:琢所,實施噴佈、塗抹、 植物種子接觸即可。 、;告轰防治有效量之化合物與 所謂植物種子意指貯蓄站f 畜則、_料所轉養分而在農業上 152 200836629 使用於繁殖者。可舉例如玉米、大 — 小麥、大麥、向日葵、番兹、胡瓜、蘇子%,、_f稻、甜菜、 甘蘼、終草、甜椒及食用油菜等之種子 木=、南瓜、 药篛等之種芋,食用百合、較之甘藷、 賦予生產殺蟲物質能力之王参= 至職作物、蟲害而適當選擇,通常從! ^於植物種子進行粉衣、嘴佈、塗抹處用旦 ^,植物種子重量之〇.()5〜5%程度 = 專1 :視製劑形態或成為處理對象之植物種限該 本务明之殺蟲組成物,一般依黨園龜 制、、殳 成使用方便形狀之製劑來使用。亦即;此ns常法’製 依需要與輔助劑以適當比例配合後使溶適2性載體或 浸潰、吸著或附著,製成如懸浮劑 $、芯汙、混合、 粒劑、粉劑、錠劑等適當劑型使用即可小H可濕性粉劑、 料可舉例二Ϊ5 成载體之材 核,穀粉、麵粉、纖維素粉、植物精油d;杳於2粉、 成樹脂等合成聚合物、黏土類(如高嶺土、土 ^二^碎^合 滑石粉類(如滑石粉、葉蠟石等)、矽石白土等)、 母、白炭黑[含水微粒矽,又稱含水人j澡土、石英砂、雲 1因製品而含微辦域分。^活^ 性矽酸’亦 藻土、紅磚粉碎物、飛灰、砂、石山 ,’丨、輕石、燒成矽 疏安、碟酸銨、硝酸銨、尿+等無機礦物性粉、 等可單獨或以2 _上之混化學肥料、堆肥等,此 至於可成為液體惰性载體之材i,除其本身具有溶劑能力者 153 200836629 :合但在輔助:協助下能夠分散於殺 ΛίΓ;ί *2 環己酮等)丙酮、f乙酮、f異丁_、二異丁酮、 丙酸乙醋、、ί本4) ’醋類(如醋酸乙醋、酷酸丁醋、 =酉曰專)’醯胺類(如二甲基甲、υ 醯胺等)’腈類(如乙腈等)。 Τ崎一曱基乙 的而表性輔助劑,此等輔助劑因應目 輔助劑。獨使或種以上合用,有時亦可能完全不使用 的而面it;溶液化及/或濕潤有效防治害蟲之化合物之目 =使=面活性劑,可舉例如聚氧乙烯烧基鍵、聚氧乙烯燒芳 二糖醇級脂肪酸醋、聚氧乙烯樹脂_、聚氧乙烯山 Γ、- = Λ月才土酉夂醋、聚氧乙烯山梨糖醇酐一油酸醋、烧芳石黃酸 孤、奈〜!^鹽、木質確酸鹽、高級醇硫酸酯等。 、 =為分散安定化、黏著及/或結合有效防治害蟲化合 =2:示辅助劑,如路蛋白、明膠、殺粉、甲基纖維素 li i阿拉轉、聚乙稀醇、松根油、米糠油、膨潤土、 二仙膠、木質磺酸鹽等。 良固體製品之流動性可使用下示輔賴,如壤、硬脂 二2^基自旨等辅助劑。祕性產品之散凝劑可使用如萘石黃酸 物、縮合碟酸鹽等辅助劑。又,消泡劑可使用如糊油ί補 ,本發明之殺蟲組成物雖對光、熱、氧化等為安定,但可 因應須要適量添加防氧化劑或紫外線吸收劑,如ΒΗΤ(2,6 —二第三 154 200836629 丁基-4 -甲紛)、BHA(丁基經基笨甲鱗)等苯紛衍生物,雙盼街生 物,或安定劑如苯基_ 〇:-萘胺、苯基_沒_萘胺、對胺基 醚與丙酮之縮合物等芳基胺類或二苯甲合物類,而獲& 更安定之組成物。 [實施例] 以下用實施列說明製造本發明之一般式(1)或一般式(5)表示之 化合物之代表性實施例,但本發明不受此等實施例之限制。 [實施例1 一 1] 、(Pediculus humanus humanus), etc.; Thereuronema tuberculata of the CHILOPODA; Oxidus gracilis of the DIPLOPODA; the mollusk gate (MOLLUSCA) double-chain chain (Incilaria bilineata) and the like. The content of the compound effective for controlling pests in the insecticidal composition of the present invention is usually 0.5 to 20% by weight in the powder, 5 to 50% by weight in the emulsion, ~90% by weight in the wettable powder, and 粒·ΐ in the granules. ~ 2 〇 wt%, water suspension is 1 〇 ~ 9 〇 weight 0 / 〇. On the other hand, the carrier 1 of each dosage form usually has a powder of ~99% by weight, an emulsion of ~95% by weight, a wettable powder of 10 to 90% by weight, a granule of 8〇 to 99% by weight, and a water suspension. The agent is 10 to 90% by weight. Further, the auxiliary dose is usually 1 to 2% by weight of the powder, 1 to 20% by weight of the emulsion, 1 to 2% by weight of the wettable powder, and 0.1 to 20% by weight of the agent, and the aqueous suspension is 〇丨 ~ sink weight%. A pest which occurs by the application of the insecticidal composition of the present invention to a harvest of an agricultural plant. That is, the invention is diluted or suspended with water to control the effective amount of pests, and the storage place of the obtained or agricultural plant harvest is sprayed, coated, smeared, ugly, or pressurized. After harvesting ___) processing ie ^ Chenye plant harvest can be, for example, rice, barley wheat oats, cowpea, kidney beans, slaves, ibem, m bean^ pequxa bean > white bean ^ #-] .^(Lima Bean) ^ . ^ ^ ^ $ . „^nectarine) ^ ^ ^ ^ s^; 151 200836629 Natsudaidai, Wenzhou Orange, Sudachi, Acid Dial, Cabos Orange (CWms, Lime) , lemon, alfalfa, alfalfa (Quince, Μ / (10)), apple, pear, pear, avocado, kiwi, guava, date palm, pineapple, passion fruit, banana, papaya, hazelnut, grass, vine Bilberry, egg bilberry, ^zcdm face ovfl plus m), blackberry, blueberry, persimmon, watermelon, grape, cantaloupe, cantaloupe, no green, broccoli, kale, radish, cabbage, small pineapple (1 variety of rape, edible Rape), water mustard or western cress (cresson, waterCress), kale or kale, horseradish (also Western Mountain) Kwai), red radish (radish), broccoli, simmer (7) 拗, sweet potato, radix radix, taro, potato, pumpkin, courgette, yucca (Cmc_ship/generous (10) face (10)), artichoke (artich〇ke), Endive, Burdock, 21lTfy) f TtT ^1' ^ ^ ^«'' ^ Feng Zhuo (P_P), Xiangxu, Fan Lin, Youzi, Bell Pepper, Lu Tube, Yangmiao, Tuas, points, calendar, window, and a variety of 曰本慧), edamame, autumn ▲, Gan borrow, I,,, two silk: unfinished, beans, immature beans, oil seeds ( Flax, rapeseed, cocoa beans, coffee beans, tea, hops (four), etc., but the seed of the seed, can be in the original form of plants or water or other appropriate dilution or 'the' / away from the Ming, the insect group The amount of the effect is stored in the plant seed or plant seed in the pest control, such as cloth, foam, powder or fumigation fumigation, etc., which is sprayed, smeared, coated by the insecticidal composition of the present invention. It is suitable for the plant and seed produced by the pests produced in the plant after sowing. This prevention is due to the treatment of coating, soaking, powder coating, etc. in the effective amount in the secret species. 2: 琢,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, For the breeder, for example, corn, large-wheat, barley, sunflower, pupa, courgette, sage, _f rice, beet, kansui, terminal grass, sweet pepper and edible rapeseed, etc. , such as medicinal sputum, edible lily, compared to sweet potato, the ability to give the production of insecticidal substances, Wangshen = suitable crops, pests and appropriate choice, usually from! ^Use the plant seeds for powder coating, mouth cloth, smear, and the weight of the plant seeds. () 5~5% degree = Special 1: The form of the preparation or the plant species to be treated The insect composition is generally used according to the formula of the party garden turtle, and the preparation is convenient to use. That is, the ns conventional method is prepared by mixing the auxiliary agent with an auxiliary agent in an appropriate ratio, or by immersing, absorbing or adhering to a suspension agent, a core, a mixture, a granule, and a powder. And appropriate dosage forms such as tablets can be used to make small H wettable powders, materials can be exemplified by 2 Ϊ 5 into the core of the carrier, grain flour, flour, cellulose powder, plant essential oil d; 杳 2 powder, resin synthesis, etc. Objects, clays (such as kaolin, soil ^ two ^ broken ^ talc powder (such as talcum powder, pyrophyllite, etc.), chert white clay, etc.), mother, white carbon black [aqueous particles 矽, also known as water-containing people j Bath soil, quartz sand, and cloud 1 contain micro-domains for products. ^活^性矽酸' also algae soil, red brick pulverized material, fly ash, sand, stone mountain, '丨, pumice, burnt 矽 安 安, ammonium silicate, ammonium nitrate, urine + and other inorganic mineral powder, It can be used alone or in combination with chemical fertilizers, composts, etc., which can be used as a liquid inert carrier, except for its own solvent ability. 153 200836629: but with assistance: can be dispersed in the killing ; ί *2 cyclohexanone, etc.) acetone, f ethyl ketone, f isobutyl _, diisobutyl ketone, ethyl vinegar propionate, ί 4 4) 'vinegar (such as ethyl acetate, diced vinegar, =酉曰Special) 'Amidoxime (such as dimethylformamide, decylamine, etc.) 'nitrile (such as acetonitrile, etc.). The auxiliaries of the Τ 曱 曱 曱 曱 , , , , , 。 。 。 。 。 。 。 。 。 。 。 If it is used alone or in combination, it may or may not be used at all; solubilization and/or wetting of the compound which is effective for controlling pests = the surface active agent, for example, polyoxyethylene alkyl bond, poly Oxyethylene burning aryl disaccharide fatty acid vinegar, polyoxyethylene resin _, polyoxyethylene hawthorn, - = Λ月才土酉夂 vinegar, polyoxyethylene sorbitan oleic acid vinegar, burning arsenic acid Lonely, Nai ~! ^ Salt, woody acid salt, higher alcohol sulfate, and the like. , = for dispersion stability, adhesion and / or combination of effective control of pests = 2: auxiliary agents, such as road protein, gelatin, powder, methyl cellulose li i Ala, polyethylene glycol, pine root oil, rice bran Oil, bentonite, dioxin, lignosulfonate, etc. For the fluidity of good solid products, the following auxiliary agents such as soil and hard fat can be used. As the decoagulant for the secret product, an auxiliary agent such as naphthalene sulphate or condensate disc acid salt can be used. Further, the antifoaming agent may be used, for example, as a paste oil, and the insecticidal composition of the present invention is stable to light, heat, oxidation, etc., but may be added with an appropriate amount of an antioxidant or an ultraviolet absorber, such as bismuth (2, 6). - two third 154 200836629 butyl-4 - A), BHA (butyl ketone albino scales) and other benzene derivatives, double hope street creatures, or stabilizers such as phenyl _ 〇: - naphthylamine, benzene An arylamine or a diphenylmethane compound such as a condensed product of an amino group and a non-naphthylamine, and a more stable composition. [Examples] Representative examples of the compounds represented by the general formula (1) or the general formula (5) of the present invention are described below by the following examples, but the present invention is not limited by the examples. [Embodiment 1 - 1],
5 —胺基一6—溴一8—七氟異丙基喹琳之製造 將5 —胺基一8 —七氟異丙基喹啉i.2ig之N,N_二曱基甲醯胺5ml 溶液於冰水浴下攪拌,接著滴加溶於N,N-二甲基甲醯胺1〇ml2N 一溴琥珀酸醯亞胺0.69g。於冰水浴下攪拌1小時、於室溫攪拌4 小時後’將乙酸乙酯與水加入於反應溶液,並分取有機相。以水 清洗2次,以無水硫酸鎂乾燥並將溶劑於減壓下餾去。藉由將得 到之&>查以砍膠管柱層析(正己烧:乙酸乙酯=8 : ·· 1)精製, 得到標題化合物1.09g(產率72%)淡褐色固體。 Η — NMR(CDC13) δ 4.98(2H,broad — s)?7.43(lH dd Τ = 3·9,8·3Ηζ),8·08(1Η,(Μ = l.〇HZ),8.13(lH,d(i,/ ’ = 1.558.3HZ),8.91(m,dd,J=L5,3.9Hz)。 ,, [貝把例1—2] N—(6~溴一8—七氟異丙基啥琳一5 —基)3 — 硝基笨曱醯胺之製造 將3 —硝基苯曱醯氯〇.47g、5 —胺基一6—溴一8 —七氟異丙基喹 琳1.5g加入於吡啶5ml,並於室溫攪拌。5小時後,於反應溶液中 加入乙酸乙酯及1N鹽酸,分取有機相,以水清洗2次、以飽和重 碳酸納水溶液清洗3次。於減壓下將溶劑餾去,並將得到之殘渣 >谷解於四氫吱嚼8ml、曱醇2ml之混合溶劑,於冰水浴下攪拌之 狀態,加入氫氧化鈉0.10g並攪拌1小時,再於室溫攪拌4小時。 於反應溶液中加入乙酸乙酯與水,分取有機相,以無水硫酸鎂乾 燥。於減壓下將溶劑餾去,將得到之殘渣以矽膠管柱層析(正己烷: 155 200836629 乙酸乙酯=4 : 1)精製’得到標題化合物〇 72g (產率52%)白色非晶 物。 iH-NmCCDClO 们·4ΐ(ΐΗ4υ=3·9,8·3Ηζ),7·61(1Η,1^= 7.8Hz) ^ 8J5(lH4dJ=l.5?83Hz)5825(1811H5sX828(lH^ 7.8HzX S.39(lH4J=7.8Hz)58.84(lH9s)58.87(lH?s)?8.92(lH4dJ= 1·5,3·9Ηζ)。 [實施例1 一3] Ν-(6 —溴一8—七氟異丙基喹啉一5 —基)3 — 胺基苯曱醯胺之製造 於N — (6—溴一8—七氟異丙基喹啉一5一基)3_硝基苯甲醯胺 〇.70g、^化鍚(I)(無水)a98g之EtOH10m]溶液中,加入濃鹽酸lml 並於60 C攪拌1小時。將反應溶液倒入冰水中,以碳酸_中和後, =析出之不溶物以矽藻土濾去。以乙酸乙酯清洗不溶物,與濾液 合併,分取有機相後,以無水硫酸鎂乾燥。將溶劑於減壓下餾去, 將析出之固體以己烷清洗,得到標題化合物〇 56g(產率85%)淡橙 色固體。 Η - NMR(DMSO - d6)占 5.41(2H細ad - s),6.83(lH,dd,J = l.5,9.3Hz),7.2〇-7.27(3H,m),7.76(lH,d(U = 4.4,8.8Hz),8.4〇 — 8.43(2H,m),9.06(l H,dd,J=1.5,4.4Hz),10.58(lH,s)。 [,施例1—4] N—(6—溴一8—七氟異丙基喹啉—5 —基)3_ [(2 —氟苯甲基)胺基]苯曱酿胺(化合物編號1 一 3〇4)之製造 於將N—(6—溴一8—七氟異丙基喹啉—5 —基)3 —胺基苯甲醯胺 〇.15g、吡啶〇.〇3g加入於四氫呋喃5ml並於室溫攪拌之溶液中, j加溶於四氫呋喃之2~氟苯甲醯氯〇.〇5g。於室溫攪拌1小 後’加入乙酸乙酯與1N鹽酸,分取有機相。將有機相以飽和重 灰酸鈉水溶液清洗1次後,以無水硫酸鎂乾燥。將此溶液過濾, 收集其濾液,將溶劑於減壓下德去,將析出之固體以二異丙醚清 j先,得到標題化合物〇·17 g(產率88%)白色固體。 H ~ NMR(DMSO - dg) δ 7.33 ~ 7.40(2H?m)57.57 -5 -Amino-6-bromo-8-heptafluoroisopropylquinine 5-Amino-8-heptafluoroisopropylquinoline i.2ig N,N-dimercaptocarboxamide 5ml The solution was stirred in an ice water bath, followed by dropwise addition of 0.69 g of N,N-dimethylformamide 1 〇 ml 2N bromosuccinate. After stirring for 1 hour in an ice water bath and 4 hours at room temperature, ethyl acetate and water were added to the reaction solution, and the organic phase was separated. It was washed twice with water, dried over anhydrous magnesium sulfate and evaporated. The title compound (1.09 g (yield: 72%) of pale brown solid was obtained from the product of <>> Η — NMR (CDC13) δ 4.98(2H, broad — s)? 7.43 (lH dd Τ = 3·9,8·3Ηζ), 8·08 (1Η, (Μ = l.〇HZ), 8.13 (lH, d(i, / ' = 1.558.3HZ), 8.91 (m, dd, J = L5, 3.9 Hz). ,, [Beizhang Example 1-2] N—(6~Bromo-8-heptafluoroisopropyl)啥琳-5-基) 3 - nitro alumine production of 3-nitrophenyl hydrazine. 47g, 5-amino-6-bromo-8-heptafluoroisopropylquinine 1.5g Add 5 ml of pyridine and stir at room temperature. After 5 hours, ethyl acetate and 1N hydrochloric acid were added to the reaction solution, and the organic phase was separated, washed twice with water, and washed with saturated aqueous sodium bicarbonate three times. The solvent was distilled off, and the obtained residue was dissolved in a mixed solvent of 8 ml of tetrahydrofuran and 2 ml of decyl alcohol, and stirred under ice-water bath, 0.10 g of sodium hydroxide was added and stirred for 1 hour, and then stirred. After stirring for 4 hours at room temperature, ethyl acetate and water were added to the reaction solution, and the organic phase was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue obtained was chromatographed by column chromatography. Alkane: 155 200836629 Ethyl acetate = 4 : 1) Refined 'Get the mark Compound 〇72g (yield 52%) white amorphous. iH-NmCCDClO ·4ΐ(ΐΗ4υ=3·9,8·3Ηζ), 7·61(1Η,1^= 7.8Hz) ^ 8J5(lH4dJ=l .5? 83 Hz) 5825 (1811H5sX828 (lH^ 7.8HzX S.39 (lH4J=7.8Hz) 58.84 (lH9s) 58.87 (lH?s)? 8.92 (lH4dJ=1·5,3·9Ηζ). [Example 1 a 3] Ν-(6-bromo-8-heptafluoroisopropylquinoline-5-yl)-3-aminobenzoaniline produced in N-(6-bromo-8-heptafluoroisopropylquin啉 一 5 5 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 70 After being added to the ice water, the insoluble matter which was precipitated after the carbonation was neutralized with celite, and the insoluble material was washed with ethyl acetate, and the filtrate was combined, and the organic phase was separated and dried over anhydrous magnesium sulfate. The residue was evaporated under reduced pressure. EtOAc (EtOAc md. lH, dd, J = l.5, 9.3 Hz), 7.2 〇 - 7.27 (3H, m), 7.76 (lH, d (U = 4.4, 8.8 Hz), 8.4 〇 - 8.43 (2H, m), 9.06 ( l H, dd, J = 1.5, 4.4 Hz), 10.58 (lH, s). [Example 1-4] N-(6-bromo-8-heptafluoroisopropylquinolin-5-yl)3_[(2-fluorobenzyl)amino]benzoquinone (Compound No. 1) A 3〇4) is produced by adding N-(6-bromo-8-heptafluoroisopropylquinolin-5-yl)3-aminobenzimidamide 〇.15g, pyridinium 〇3g to tetrahydrofuran 5 ml and stirred at room temperature, j was added with 2~ fluorobenzhydryl chloride 〇 5 g dissolved in tetrahydrofuran. After stirring at room temperature for 1 hour, ethyl acetate and 1N hydrochloric acid were added, and the organic phase was separated. The organic phase was washed once with a saturated aqueous solution of sodium succinate and dried over anhydrous magnesium sulfate. The solution was filtered, and the filtrate was evaporated. EtOAcjjjjjjjjjj H ~ NMR (DMSO - dg) δ 7.33 ~ 7.40 (2H?m) 57.57 -
7-63(2H5m)57.68-7.73(lH5m)57J7(lH5dd?J=:3.958.8HzX 7.90(lH5dJ 156 200836629 =7.8Hz),8.03(m,d,J = 7·8Ηζ),8·41 - 8.49(3H,m),9.08(lH,dd,J = 1·5,3·9Ηζ),10.70(m,s),10.84(lH,s)。 ’ ’ [實施例2 — 1] N—(4一七氟異丙基一2—曱基石黃醯基苯基)一n 一甲基3—石肖基苯甲醯胺之製造 於使60%氫化鈉〇.15g懸浮於四氫呋喃5ml之溶液中,於室溫滴 加溶於四氳呋喃5ml之N—(4—七氟異丙基一2—甲基磺醯基苯基) 3—石肖基本曱蕴胺1.5g。於室溫攪拌30分鐘後,滴加溶於四氳π夫 喃5ml之碘甲烷〇.94g。接著,升溫至70°C,攪拌12小時後,返 回室溫,將乙酸乙酯及水加入於反應溶液中。分取有機相,以水 清洗1次後,以無水硫酸鎂乾燥,將溶劑於減壓下餾去。將得到 之殘渣以矽膠管柱層析(正己烷:乙酸乙酯=6:丨)精製,得到標題 化合物0.98g(產率64%)淡黃色固體。 lR _ NMR(CDC13) 5 3.21(3H,s),3.39(3H,s),7,64(m,d,J = 8.3Hz),7.73(lH,t,J = 7.8Hz),8.03(lH,d,J = 8.3Hz),8.07(lH,d,J = 7·8Ηζ),8.38-8.41(2H,m),8.55(lH,s)。 [實施例2 — 2] N—(4 —七氟異丙基一2—甲基石黃苯基)一N—曱 基3 —胺基苯甲醯胺之製造 ,N—(4—七氟異丙基—2—甲基磺醢基苯基—甲基3一硝基 本曱S&fec 0.93g、氣化錫(1)(無水)i 4〇g加入於乙醇20ml,接著, 滴加濃鹽酸2ml。裝入後,升溫至60°c,攪拌15小時,將反應溶 液倒入於冰水中。以碳酸鉀進行中和操作,加入乙酸乙酯後,將 ϋ之不溶物使用矽藻土濾去。將矽藻土之濾集物以乙酸乙酯充 分清洗。分取濾液之有機相,以無水硫酸鎂乾燥,將溶劑於減壓 下餾去,將得到之殘渣以矽膠管柱層析(正己烷··乙酸乙酯=1: D ,製,得到標題化合物〇·8 2g(產率94%)無色油狀物。 Η - NMR(CDC13) 5 3J9(3H5s)339(3as)93.88(2H5broad -7-63(2H5m)57.68-7.73(lH5m)57J7(lH5dd?J=:3.958.8HzX 7.90(lH5dJ 156 200836629=7.8Hz),8.03(m,d,J=7·8Ηζ),8·41 - 8.49 (3H, m), 9.08 (lH, dd, J = 1. 5, 3. 9 Ηζ), 10.70 (m, s), 10.84 (lH, s). ' ' [Example 2 - 1] N - (4 1. Heptafluoroisopropyl-2-oxanyl xanthyl phenyl)-n-methyl 3-succinyl benzamide is prepared by suspending 60% sodium hydride 〇.15g in 4ml of tetrahydrofuran and dropping at room temperature. Add N-(4-heptafluoroisopropyl-2-methylsulfonylphenyl) 3 - Shisha basic amine 1.5g dissolved in tetrahydrofuran. Stir at room temperature for 30 minutes, add dropwise Dissolve in 94 ml of iodomethane oxime of 4 ml of π 夫 喃 。. Next, the temperature is raised to 70 ° C, stirred for 12 hours, and then returned to room temperature, ethyl acetate and water are added to the reaction solution, and the organic phase is separated. After the water was washed once, the residue was dried over anhydrous magnesium sulfate (MgSO4). (yield 64%) light yellow solid. lR _ NMR (CDC13) 5 3.21 (3H, s), 3.39 (3H s), 7, 64 (m, d, J = 8.3 Hz), 7.73 (lH, t, J = 7.8 Hz), 8.03 (lH, d, J = 8.3 Hz), 8.07 (lH, d, J = 7) · 8Ηζ), 8.38-8.41 (2H, m), 8.55 (lH, s) [Example 2 - 2] N-(4-heptafluoroisopropyl-2-methyl-stone phenyl)-N- Manufacture of fluorenyl 3-aminobenzamide, N-(4-pentafluoroisopropyl-2-methylsulfonylphenyl-methyl 3-nitrobenzidine S&fec 0.93g, gasified tin (1) (anhydrous) i 4 g was added to 20 ml of ethanol, followed by dropwise addition of 2 ml of concentrated hydrochloric acid. After the addition, the temperature was raised to 60 ° C, stirred for 15 hours, and the reaction solution was poured into ice water. After the neutralization operation, ethyl acetate was added, and the insoluble matter of the mash was filtered off with diatomaceous earth. The filtrate of the diatomaceous earth was washed thoroughly with ethyl acetate. The organic phase of the filtrate was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified mjjjjjjjjjjjjjjj Η - NMR (CDC13) 5 3J9 (3H5s) 339 (3as) 93.88 (2H5broad -
sX6.80(lH?d9J = 7.8Hz)?6.96(1H,s)?7.〇4( lH?dJ = 7-8Hz)?7.26(1H5U = 7.8I^z),7.60(m,d,J=7.8Hz),7.99(m,d,J=7.8^)5M^ [貫施例2 —3] N-(4-七氟異丙基—2_甲基磺醯基苯基)—n 200836629 1)精製’得到標題化合物〇.38g(產率14%)。 [貫施例=-2]2,4,6-三漠-3-(七1一正丙硫基)苯胺之製造 於將七氟一正丙硫基)苯胺〇38g加入於N,N_二曱基曱醯胺 10ml之溶液中,添加溴琥珀酸醯亞胺〇J2g。於6〇。〇攪拌2 小日守後,加入醚及水,分取有機相。將有機相以水清洗2次後, =播水硫酸鎂乾煉,將溶劑於減壓下餾去,將得到之殘渣以矽膠 官柱層析(正己烷:乙酸乙酯=8:1)精製,得到標題化合物〇. 6產 率89%)紅色油狀物。sX6.80(lH?d9J = 7.8Hz)?6.96(1H,s)?7.〇4( lH?dJ = 7-8Hz)?7.26(1H5U = 7.8I^z), 7.60(m,d,J = 7.8 Hz), 7.99 (m, d, J = 7.8^) 5 M^ [Examples 2 to 3] N-(4-heptafluoroisopropyl-2-methylsulfonylphenyl)-n 200836629 1) Purification 'The title compound 〇. 38 g (yield 14%) was obtained. [Comprehensive Example = -2] 2,4,6-Sanmo-3-(seven-l-n-propylthio)aniline was produced by adding heptafluoro-n-propylthio)aniline oxime 38g to N,N_ To a solution of dimercaptoamine in 10 ml, ruthenium bromide succinimide J2g was added. At 6 〇. After stirring for 2 days, add ether and water and separate the organic phase. After the organic phase was washed twice with water, the mixture was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 8:1). The title compound 〇. 6 yield 89%)
iH-NMRfDC^) d 4.87(2H,s),7.83(lH,s)。 [貫施例5-3] N- {2,4,6-三漠-3-(七敦一正丙硫基苯 基3—石肖基苯曱醯胺之製造 將2,4,6—三溴一3 —(七氟一正丙硫基)苯胺〇 61g、3 —硝基苯曱醯 氯〇.43g添加於吡啶20ml,於7〇t:攪拌2小時後,將乙酸乙酯及 水添加於反應溶液。分取有機相,以無水硫酸鎂乾燥。將此溶液 過濾,收集濾液,將溶劑於減壓下餾去,將得到之殘渣以矽膠管 柱層析(正己烷:乙酸乙酯=4 : 1)精製,得到標題化合物〇.69 (產 率89%)白色固體。 !H-NMR (CDC13) (5 7.76(1H^J=7.8Hz)JJ8(1H5s)?8.15(1H9s)583 2(lH,d,J=7.8Hz),8,47-8e50(lH,m)58J9(m,s)。 [貫施例5-4] N- {2,4,6-三溴-3-(七氟一正丙硫基笨 基3 —胺基苯曱醯胺之製造 於將1{2,4,6-三漠-3一(七氟一正丙硫基)}苯基3 —硝基笨 曱,醯胺0.69g、氯化錫(I)無水物(X6〇g加入於乙醇2〇ml並於室溫攪 拌之/谷液中,加入?辰鹽酸1 ml,於60°C加熱攪拌2小時。返回室 溫後,將反應溶液注入水中,使用碳酸鉀進行中和操作。加入乙 k乙酯’濾去不溶物後,分取有機相,以無水硫酸鎂乾燥。將此 溶液過濾,收集濾液,將溶劑於減壓下餾去,將得 烧清洗,制獅化合物0.62g(鲜94%)自色e (CDC13) 5 3.89(2H9s)56.89(lH4t?J = 6.4?2.4Hz)?7.27 ^ 160 200836629 實施例2 —2記載之條件,製造標題化合物(產率97%)。 ^NMR^DC^) δ 3.53 (2H9brs)56.40 (lH5septet?J = 6.4Hz)56.77 (lH,d,J=8.8Hz),7.09 (m,dd,J=2.9,8·8Ηζ),7·60 (lH,d,J=2.9Hz)。 [實施例6 — 3] 6—溴一5 —胺基一2 — (2,2,2 —三氟一 i一三氟 曱基乙氧基)ϋ比唆之製造 將5 —胺基一2 — (2,2,2 —三氟一 1 一三I甲基乙氧基比咬2.0g加入 於N,N-二甲基甲醯胺15ml,並於室溫添加N—溴號ί白酸i.36g。 於室溫攪拌2小時後,加入乙酸乙醋,以水清洗。以無水硫酸|美 乾燥後’以石夕膠管柱層析(正己烧:乙酸乙酯=1〇 : 1)精製,得到 標題化合物2.35g油狀物(產率:90%)。 H-NMR(CDC13) 5 3.92 (2H,brs),6.23 (lH,septet,J = 7.4Ηζ),6·77 (lH,d,J=8.3Hz),7.12 (lH4,J=8.3Hz)。 ^ [實施例6一4] N — [2—溴一4一(2,2,2—三氟一1 —三氟曱基乙 氧基)一吼咬一3 —基]3〜硝基苯曱醯胺之製造 ^用6—,一5—胺基一2 —(2,2,2—三氟一1 一三氟曱基乙氧基)吡 咬,依照實施例1 一2記載之條件,製造標題化合物(產率·· 92%)。 'H-NMRCCDCls) (5 631 (IH.septeU = 5.8Hz)97.06(1H5cU = 8.8Ηζ),7·77 (lH,t,J = 8·3Ηζ),8·25 - 8·29 (2 H,m),8.47 - 8·50 (lH,m),8.77—8·8 2 (2H,m)。 [實施例6-5] NH — 4_(2,2,2一三氣—三氟曱基乙 氧基)—*定_3-基]基苯甲醯胺之製造 N - [2-溴-4-(2,2,2 —三氟η 一三氟曱基乙氧基)一比唆—3 一 基]使用3-硝基苯甲酸胺,依照實施例卜3記載之條件,製造 標題化合物(產率·· 81%)。 、 ^-NMRCCDCls) (5 3.90 (2H5brs)?6.29 (lH5septetJ = 5.9Hz)56.88-6·91 (1Η,πι),7·00 (lH,d,J > 8 8Hz),7 21 一 7 32 (3Η,πι),8·23 (lH,brs),8.85 (lH,d,J=8.3Hz) 0 产[實施=6-6] N-[2〜填一6—(2,2,2 —三u一三氣曱基乙 氧基)一咖定-3-基]L(笨甲基胺基)苯甲醯胺(化合物編號i 162 200836629 一 387)之製造 … 使用N—[2—溴一6 —(2,2,2 —三氟一1 —三氟甲基乙氧基)一吡啶 一3—基]3—胺基苯甲醯胺及氣化苯曱醯基,依照實施例1 一4記載 之條件,製造標題化合物(產率:76%)。 . 4-NMR(CDC13) (5 630 (lH,septet,J = 6.8Hz),7.01(lH,d,J = 8.8Hz)J.49 - 7.61(4H?m)97.68(lH5dd5J = L0J.8Hz)57.88 - 7.91 (2H,m),7.96 — 8.01(2H,mX8.26(lH,t,J = 1.9Hz),8.33(lH,s),8、81 (lH,d,J=8.8Hz)。 [實施例7—1] N—(2—溴一6—曱基一4一三曱基乙醯氧基苯 _ 基)3 —硝基苯曱醯胺之製造 依照Tetrahedronl2263-12276頁(1995年)記載之方法,使用合成 之2—曱基一4-(三曱基乙醯氧基)苯胺,依照實施例1 —i記載之 條件製備2 —溴一6 —曱基一4 —(三曱基乙醢氧基)苯胺,並依照1 —2記載之條件,製造標題化合物(產率:52%)。 々·NMRCCDab) 5 1.36(9H,s),2.36(3H,s),7.00(lH,d,J= 2.0Hz);7.27(m,d,J=2.0Hz),7.65(m,bL),7.74(m,U= 8.3Hz),8.31(lH,dd,J= 1·5,6.3Ηζ),8·44 —8.47(lH,mX8.79(lH5t,J= 2·0Ηζ) 〇 % [實施例7 — 2] Ν—(2 —溴一6 —曱基一4一羥基苯基)3—胺基 苯曱醯胺之製造 將N—(2—溴一6 —甲基一4一三甲基乙醯氧基苯基)3 —硝基苯甲 醯胺及氫氧化鈉水溶液加入於曱醇,於7〇°c攪拌3小時。於減壓 下將溶劑顧去,將得到之殘渣以乙酸乙酯溶解,以2N鹽酸水溶液 清洗後’以無水硫酸鎂乾燥,並於減壓下將溶劑餾去。將得到之 殘渣以矽膠管柱層析(正己烷:乙酸乙酯=1 ··丨)精製,得到(2 二溴一6一甲基一4一羥基苯基)3 —硝基苯甲醯胺,之後,依照實 施例1 一3記載之條件,製造標題化合物(產率97%)。 、 ^ [,施例7~3] N—(2—溴一4一羥基一6—甲基一苯基)3一 (苯曱醯基胺基)苯曱醯胺之製造(化合物編號1—484) 163 200836629 使用N—(2—漠一6 —甲基一4一經基苯基)3 —胺基苯甲酿胺,依 照實施例1 一4記載之條件,製造標題化合物(產率95%)。 ^-NMRf DMSO-d6) δ 2.16(3H,s),6.72( lH,d,J = 2.4Hz),6.94(lH,d,J = 2·4Ηζ),7·50 — 7.63(4H,m),7.74(lH,d,J = . 8·3Ηζ),7·98 — 8.05(3H,m),8.32(m,s),9.79(m,s),9.81(lH,s),10.4(m,s)。 [實施例7 — 4] N—(2—溴一6—甲基一4一三氟甲烧磺醯氧基 苯基)3 — (苯曱醯基胺基)苯曱醯胺之製造(化合物編號! _369) 將N—(2—溴一6—曱基一4一羥基苯基)3 — (苯曱醯基胺基)苯曱 瞻 醯胺0.2g及三氟曱烧續醯基無水物〇j4g加入於η比咬,於攪 拌7小時。將溶劑於減壓下餾去,將得到之殘渣以矽膠管柱層析(正 己烷:乙酸乙酯=1 : 1)精製,得到標題化合物〇.〇8g (產率31%)。 !H-NMR( DMSO-d6) 5 2.32(3H?S)?7.52 - 7.63(5H5m)?7.76(lH5(U =7.8Hz)57.87(lH?d?J = 2.7Hz)58.00(2H?dd?J= l-557.8Hz)?8.06(lH5d?J = 7·8Ηζ),8·37( 1H,s),10.18(1H,s),10.47(1H,s) o [實施例7 — 5] N — [2—溴一0一甲基一4 —(對曱苯石黃醯氧基) 苯基]3-(苯甲醯基胺基)苯曱醯胺之製造(化合物編號!一485) 將N-(2-溴一6—曱基一4 —羥基苯基)3 — (苯曱醯基胺基)苯曱 &&胺0.30g、1,1,1,3,3,3 —六氣異丙基對甲苯石黃酸輯〇.23g、碳酸卸 瞻 0.19g、18—冠一6醚0.03g加入於N,N-二曱基甲醯胺5ml,於70 C攪:摔6小時。加入乙酸乙I旨100ml ’以水(5〇mlx2)清洗。將有機 相以無水硫酸鎂乾燥’於減壓下德去溶劑,將得到之殘渣以砍膠 管柱層析(正己烷··乙酸乙酯=3:1)精製,得到標題化合物〇〇5g(產 率 13%) 〇 'H NMR( CDC13) δ 2.29(3H,s),2.48(3H,S),6.94(lH,d,J = 2·9Ηζ),7·14 (lH,d,J = 2.9Hz),7.36(2H,d,J = 8·3Ηζ),7’·51 — 7·61(5Η,ιη),7·71 - 7.77( 3H,m),7.88 一 7.92(3H,m),7.99(lH,br.s)58.28(m,s)。 [實施例8—l]N—(2,6—二甲基一4—七氟異丙基)苯基3一硝 164 200836629 基苯甲醯胺之製造 於將2,6—二曱基一4—七氟異丙基苯胺2〇.〇g、η比咬n 〇g加入於 四氳呋喃100ml並於室溫攪拌之溶液中,緩慢滴加溶於四氫呋喃 20ml之3 —硝基苯甲醢氯13X)g。於室溫擾拌小時後,將乙酸 乙酯及水加入於反應溶液。進行分液操作後,分取有機相,以無 水硫酸鎂乾燥。將此溶液過濾,收集濾液,將溶劑於減壓下餾去, 將得到之殘渣以己烷一二異丙醚混合溶劑清洗,得到標題化合物 26.0g(產率85%)白色固體。 ^NMRCCDCls) 5 2.33(6H5s)97.37(2H?s)57.68(lH?s)?7.72(lH?t?J = 8.1Hz)58.28(lH?d?J=8.1Hz)?8.44(lH5dd?J=L2?8.1Hz)58.75 (lH5t5J= 1.2Hz) ’ ’ ’ [實施例8 — 2] N—(2,6 —二甲基一4—七氟異丙基)苯基3 —胺基苯甲醯胺之製造 於將N — (2,6—二曱基一4一七氟異丙基)苯基3一硝基苯曱醯胺 〇.90g、氯化錫(I)無水物1.56g·加入於乙醇25ml並於室溫攪拌之溶 液,加入濃鹽酸2ml,於60°C攪拌1小時。返回室溫後,將反應 溶液注入於水中,使用碳酸鉀進行中和操作。加入乙酸乙酯,濾 去不溶物後,分取有機相,以無水硫酸鎂乾燥。將此溶液過濾, 收集濾液,將溶劑於減壓下餾去,將得到之殘渣以己烷清洗Γ得 到標題化合物0.44g(產率53%)白色固體。 ^-NMRCCDCls) δ 2.34(6H?S)3.87(2H ?broad)?6.86 - 6.89(lH5m)57.20-7 35(6H5m) [實施例8 — 3] N—[2,6—二甲基一4一(七氟異丙基)苯基]3一(4一硝基笨基胺基) 笨曱醯胺(化合物編號5 — 9)之製造 將N — (2,6—二曱基一4一七氟異丙基)苯基3_胺基苯甲醯胺 〇.3g、4—溴硝基苯〇.18g、9,9一二甲基一4,5 —二(二苯基膦山嗟 21mg、碳酸铯0.29g放入於反應容器,於氮氣流下、室溫攪拌15 分鐘。放入乙酸鈀6mg後,於9〇°C於氮氣氛反應6小時。冷卻至 165 200836629 室溫後,加入乙酸乙酯,以水清洗。以無水硫酸鎂乾燥後,於減 … 壓下將溶劑餾去,將得到之殘渣以矽膠管柱層析(正己烷··乙酸乙 酯=1 0 : 1—8 ·· 2-2 ·· 1)精製,得到標題化合物〇16g(產率74%) * 黃色結晶。iH-NMRfDC^) d 4.87 (2H, s), 7.83 (1H, s). [Culture Example 5-3] N-{2,4,6-Tri-Methyl-3-(Seven-D-Pro-propylthiophenyl 3-s-succinylbenzamide) 2,4,6-tribromo 33-(heptafluoro-n-propylthio)aniline oxime 61g, 3-nitrophenylhydrazine chlorohydrazine. 43g was added to pyridine 20ml, stirred at 7〇t: for 2 hours, then added ethyl acetate and water The reaction solution was separated, and the organic phase was separated and dried over anhydrous magnesium sulfate. The filtrate was filtered, the filtrate was collected, and the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (hexane: ethyl acetate = 4) : 1) To give the title compound 〇. 69 (yield: 89%) as a white solid. ???H-NMR (CDC13) (5 7.76 (1H^J=7.8Hz)JJ8(1H5s)?8.15(1H9s)583 2 lH, d, J = 7.8 Hz), 8, 47-8e50 (lH, m) 58 J9 (m, s) [Scheme 5-4] N-{2,4,6-tribromo-3-( Heptafluoro-n-propylthiophenyl-phenyl-3-aminobenzamine is produced by using 1{2,4,6-tri-di-3-(heptafluoro-n-propylthio)}phenyl 3-nitro Awkward, 0.69g of decylamine, anhydrous of tin (I) chloride (X6〇g is added to 2〇ml of ethanol and stirred at room temperature / gluten, 1 ml of hydrochloric acid is added, heated and stirred at 60 ° C 2 hours. After returning to room temperature, it will be reversed The solution was poured into water and neutralized with potassium carbonate. After adding ethyl acetate to remove the insoluble matter, the organic phase was separated and dried over anhydrous magnesium sulfate. The solution was filtered, and the filtrate was collected under reduced pressure. Distilled, it will be burned and cleaned, lion compound 0.62g (fresh 94%) self-color e (CDC13) 5 3.89 (2H9s) 56.89 (lH4t? J = 6.4? 2.4Hz)? 7.27 ^ 160 200836629 Example 2 - 2 The title compound was prepared (yield: 97%). NMR^DC^) δ 3.53 (2H9brs) 56.40 (lH5septet?J = 6.4 Hz) 56.77 (lH, d, J = 8.8 Hz), 7.09 (m, Dd, J = 2.9, 8 · 8 Ηζ), 7 · 60 (lH, d, J = 2.9 Hz) [Example 6 - 3] 6 - bromo-5-amino 2 - (2, 2, 2 - Preparation of trifluoro-i-trifluorodecyl ethoxy) ruthenium iridium 5 5-amino-2 - 2,2,2-trifluoro-1,3-trimethylol ethoxylate than 2.0g 15 ml of N,N-dimethylformamide, and adding 1.36 g of N-bromine acid at room temperature. After stirring at room temperature for 2 hours, ethyl acetate was added and washed with water. After drying in the US, it was refined by Shixi rubber column chromatography (positive hexane: ethyl acetate = 1 〇: 1) to obtain the title. Oil compound 2.35g (yield: 90%). H-NMR (CDC13) 5 3.92 (2H, brs), 6.23 (lH, septet, J = 7.4 Ηζ), 6.77 (lH, d, J = 8.3 Hz), 7.12 (lH4, J = 8.3 Hz). ^ [Example 6 - 4] N - [2-bromo-4-iso(2,2,2-trifluoro-1,3-trifluorodecylethoxy)-anthracene 3-amino]3~nitrobenzene Preparation of guanamine using 6-, 5- 5-amino-2-(2,2,2-trifluoro-l-trifluorodecylethoxy) pyridine, according to the conditions described in Example 1-2 The title compound was produced (yield · 92%). 'H-NMRCCDCls) (5 631 (IH.septeU = 5.8Hz) 97.06 (1H5cU = 8.8Ηζ), 7·77 (lH, t, J = 8·3Ηζ), 8·25 - 8·29 (2 H, m), 8.47 - 8·50 (lH, m), 8.77 - 8·8 2 (2H, m) [Example 6-5] NH-4_(2,2,2,3-tris-trifluoromethane Manufacture of ethoxy)-formyl-3-yl]benzamide amide N-[2-bromo-4-(2,2,2-trifluoroη-trifluorodecylethoxy)-pyrene The title compound (yield · 81%) was obtained according to the conditions described in Example 3 using the 3-nitrobenzoic acid amine. (M-NMR NMRCls) (5 3.90 (2H5brs)? 6.29 (lH5septetJ = 5.9 Hz) 56.88-6·91 (1Η, πι), 7·00 (lH, d, J > 8 8Hz), 7 21 - 7 32 (3Η, πι), 8·23 (lH, brs), 8.85 (lH,d,J=8.3Hz) 0 Production [Implementation=6-6] N-[2~Fill a 6-(2,2,2-tri-u-three-trimethylthio)ethoxylate Manufacture of -3-yl]L (stupylmethylamino)benzamide (Compound No. i 162 200836629-387) Using N-[2-bromo-6-(2,2,2-trifluoro-1) -trifluoromethylethoxy)pyridin-3-yl]3-aminobenzamide and gasified benzoquinone, according to the article of Example 1 The title compound was obtained (yield: 76%). 4-NMR (CDC13) (5 630 (lH, septet, J = 6.8 Hz), 7.01 (lH, d, J = 8.8 Hz) J.49 - 7.61 (4H?m) 97.68 (lH5dd5J = L0J.8Hz) 57.88 - 7.91 (2H, m), 7.96 - 8.01 (2H, mX8.26 (lH, t, J = 1.9Hz), 8.33 (lH, s), 8 , 81 (lH, d, J = 8.8 Hz) [Example 7-1] N-(2-bromo-6-fluorenyl- 4,3-trimethylsulfonyloxybenzene-yl)3-nitrobenzene Preparation of guanamine The preparation of guanamine according to the method described in Example 1-i is carried out according to the method described in Tetrahedronl 2263-12276 (1995) using the synthesized 2-indolyl-4-(trimethylethenyloxy)aniline. -Bromo-6-fluorenyl-4-(trimethylethenyloxy)aniline, and the title compound was obtained (yield: 52%) according to the conditions described in 1-2. 々·NMRCCDab) 5 1.36 (9H, s), 2.36 (3H, s), 7.00 (lH, d, J = 2.0 Hz); 7.27 (m, d, J = 2.0 Hz), 7.65 (m, bL), 7.74 (m, U = 8.3 Hz), 8.31 (lH, dd, J = 1. 5, 6.3 Ηζ), 8.44 - 8.47 (lH, mX8.79 (lH5t, J = 2·0Ηζ) 〇% [implementation Example 7 - 2] Ν-(2 - bromo-6-fluorenyl-4-tetrahydroxyphenyl) 3-aminophenyl phthalamide is produced by N-(2-bromo-6-methyl-1,4-31 Ethyl ethoxy phenyl) 3-nitrobenzamide and aqueous sodium hydroxide solution were added to decyl alcohol and stirred at 7 ° C for 3 hours. The solvent was removed under reduced pressure to give the residue as acetic acid. The ethyl ester was dissolved, washed with a 2N aqueous solution of hydrochloric acid, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue obtained was purified by column chromatography (n-hexane: ethyl acetate = 1 · 丨) The title compound (yield: 97%) was obtained from the title compound (yield: 97%). , ^ [, Example 7~3] N-(2-bromo-4-hydroxy-6-methyl-phenyl)-3-monophenylphosphonylbenzamide Manufacture (Compound No. 1-484) 163 200836629 Using N-(2-Nyphos-6-methyl-4-tetrapyridylphenyl)3-aminobenzamide, the title was produced according to the conditions described in Examples 1 to 4. Compound (yield 95%). ^-NMRf DMSO-d6) δ 2.16 (3H, s), 6.72 (1H, d, J = 2.4 Hz), 6.94 (lH, d, J = 2·4 Ηζ), 7· 50 — 7.63(4H,m), 7.74(lH,d,J = . 8·3Ηζ), 7.98 — 8.05(3H,m), 8.32(m,s),9.79(m,s),9.81( lH, s), 10.4 (m, s). [Example 7-4] Manufacture of N-(2-bromo-6-methyl-4-tetrafluoromethanesulfonyloxyphenyl)3-(phenylhydrazino)phenylamine (Compound) No. _369) N-(2-bromo-6-fluorenyl-4-hydroxyphenyl)3-(phenylhydrazinoamino)benzoquinone 0.2g and trifluorosulfonium ruthenium anion 〇j4g was added to η to bite and stirred for 7 hours. The solvent was evaporated under reduced pressure. EtOAc m. !H-NMR( DMSO-d6) 5 2.32(3H?S)?7.52 - 7.63(5H5m)?7.76(lH5(U=7.8Hz)57.87(lH?d?J=2.7Hz)58.00(2H?dd? J=l-557.8 Hz)?8.06 (lH5d?J=7·8Ηζ), 8.37 (1H, s), 10.18 (1H, s), 10.47 (1H, s) o [Example 7-5] N — [2-Bromo-O-methyl- 4-(p-pfite xantheneoxy) phenyl]3-(benzhydrylamino)benzamide (manufacturing number! 485) N-(2-bromo-6-fluorenyl-4-hydroxyphenyl) 3 -(phenylhydrazinoamino)phenylhydrazine &&&>amine 0.30g, 1,1,1,3,3,3 — Six gas isopropyl p-toluene yellow acid series 23.23g, carbonic acid decanting 0.19g, 18-crown one 6 ether 0.03g added to N, N-dimercaptocarhamamine 5ml, stirred at 70 C: fell 6 Adding acetic acid to the 100 ml of water to wash with water (5 〇mlx2). The organic phase is dried over anhydrous magnesium sulfate. The solvent is removed under reduced pressure, and the residue obtained is chromatographed on a chopping column (n-hexane·· Ethyl acetate = 3:1) to give the title compound (5 g) (yield: 13%) 〇'H NMR (CDC13) δ 2.29 (3H, s), 2.48 (3H, S), 6.94 (1H, d, J = 2·9Ηζ), 7·14 (lH, d, J = 2.9Hz), 7.36 (2H, d, J = 8·3Η) ), 7'·51 — 7·61(5Η,ιη),7·71 - 7.77( 3H,m), 7.88 a 7.92(3H,m),7.99(lH,br.s)58.28(m,s) [Example 8.1] N-(2,6-dimethyl-1,4-pentafluoroisopropyl)phenyl 3-nitrate 164 200836629 Benzobenzamide is produced by using 2,6-didecyl 4-4-Hexafluoroisopropylaniline 2〇.〇g, η than bite n 〇g was added to tetrahydrofuran 100ml and stirred at room temperature, slowly adding 3ml of nitrobenzene dissolved in tetrahydrofuran 20ml醢Chlorine 13X)g. After stirring at room temperature for an hour, ethyl acetate and water were added to the reaction solution. After the liquid separation operation, the organic phase was separated and dried over anhydrous magnesium sulfate. The solution was filtered, and the filtrate was evaporated. EtOAcjjjjjjjjjjjj ^NMRCCDCls) 5 2.33(6H5s)97.37(2H?s)57.68(lH?s)?7.72(lH?t?J=8.1Hz)58.28(lH?d?J=8.1Hz)?8.44(lH5dd?J= L2? 8.1 Hz) 58.75 (lH5t5J = 1.2 Hz) ' ' ' [Example 8 - 2] N-(2,6-dimethyl-1,4-heptafluoroisopropyl)phenyl 3-aminobenzamide The amine is produced by adding N-(2,6-dimercapto-tetrakisylfluoroisopropyl)phenyl 3-nitrophenylamine 〇.90g, tin chloride (I) anhydrate 1.56g· A solution of 25 ml of ethanol and stirring at room temperature was added to 2 ml of concentrated hydrochloric acid, and stirred at 60 ° C for 1 hour. After returning to room temperature, the reaction solution was poured into water, and neutralization was carried out using potassium carbonate. After adding ethyl acetate and filtering off the insoluble material, the organic phase was separated and dried over anhydrous magnesium sulfate. The solution was filtered, and the filtrate was evaporated. EtOAcjjjjjjjjjj ^-NMRCCDCls) δ 2.34(6H?S)3.87(2H?broad)?6.86 - 6.89(lH5m)57.20-7 35(6H5m) [Example 8-3] N-[2,6-dimethyl-4 Production of mono(heptafluoroisopropyl)phenyl]3-mono(4-nitrophenylamino)benzamide (Compound No. 5-9) will be N — (2,6-dimercapto-4-one Heptafluoroisopropyl)phenyl 3 -aminobenzimidamide 〇.3g, 4-bromonitrophenylhydrazine. 18g, 9,9-dimethyl- 4,5-di(diphenylphosphine) 21 mg and 0.29 g of cesium carbonate were placed in a reaction vessel, and stirred under a nitrogen stream at room temperature for 15 minutes. After 6 mg of palladium acetate was added, the mixture was reacted at 9 ° C for 6 hours in a nitrogen atmosphere. After cooling to 165 200836629, the temperature was added. Ethyl acetate was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, and the residue obtained was purified by column chromatography (n-hexane·ethyl acetate = 1 0 : 1-8) ·· 2-2 ·· 1) Purification, the title compound 〇16g (yield 74%) * yellow crystals.
^-NMRCCDCls)占 2.36 (6H,s),6.50 (lH,brs),7.02 (2H,d,J = 8.7Hz)J.38 (2H5s)?7.42 (1H?s)57.46 (1 196H?(U=7.8Hz)?7.53 (1H5U = 7·8Ηζ),7·60 (lH,d,J=:7.8Hz),7.91 (lH,brs),8.19 (2H,d,J=8.7Hz)。 —,[實施^列9—1] [3 — [(2,6 —二曱基—4一七氟異丙基苯基) 胺基.基]本基]4—氯笨;ε風醯胺之製造(化合物編號之製造 φ 於實施j 8 —2所製造Ν—(2,6一二曱基一4一七氟異丙基)苯基3 —胺基苯甲醯胺〇.30g加入於吡啶5m 1之溶液中,放入4一氯苯磺 基氯〇.16g,於室溫擾拌2小時。接著,加入乙酸乙酯後,注入 於冰水。使用 >辰鹽酸使水相成酸性,分取有機相,以飽和碳酸氫 鈉水溶液清洗2次後,以無水硫酸鎂乾燥。將溶劑於減壓下餾去, 將得到之殘渣以矽膠管柱層析(正己烷:乙酸乙酯=2 : 1)精製,得 到標題化合物0.30g(產率70%)台色非晶物。 'H.NMRCCDCls) 5 2.29(6H5s)?7.32 - Ί. 39(6H?m)?7.58 - 7.66(6H,m)。 [實施例10 — 1] 4一(1,1,2,3,3,3 —六氟丙氧基)一硝基苯之製 攀 造 於將對硝基酚4.63g及氫氧化鉀0 56g加入於N,N_二曱基曱醯胺 lOjril之溶液中,於室溫吹入六氟丙烷後,於5(rc攪拌1小時。 接著’加入乙酸乙酯及水後,分取有機相。將有機相以無水硫酸 鈉乾燥’並將溶劑於減壓下餾去,以矽膠管柱層析(正己烷:乙酸 1 乙醋=2〇: 1;)精製,得到標題化合物3.81g(產率42%)黃色油狀物。 H-NMR (CDCls) δ 5.06 (lH5ddtJ=44.05lL255.2Hz)57.39 (2H?d5J = 8·8Ηζ),8·30 (2H,d,J=8.8Hz)。 [實施例10—2]4〜(U,2,3,3,3—六氟丙氧基)一苯胺之製造 使甩4一(1,1,2,353,3~六氟丙氧基)—硝基苯,依照實施例1一3記 166 200836629 載之條件,得到標題化合物油狀物。 (CDCI3) δ 3·69 (2H,brs),4·% (lH,dddcU = 44·0,11·2,11.2,5·6Ηζ),6.64(2H,d,J=&8Hz),6.98(2H5d,J=8.8Hz)。 [實施例 10—3] 2,6—二溴一4一(1,1,2,3,3,3 — 六氟丙氧基)_ 苯胺之製造 使用N—溴號酸酿亞胺2當量,依照實施例1 — 1記載之條件, 製造標題化合物油狀物。 'H-NMR (CDCI3) δ 4.51 (2H,brS),4.96 (lH,dddd,J = 44·0,11·2,11·2,6·0Ηζ),7.30(2H,s) 0^-NMRCCDCls) 2.36 (6H, s), 6.50 (lH, brs), 7.02 (2H, d, J = 8.7 Hz) J.38 (2H5s)? 7.42 (1H?s) 57.46 (1 196H? (U = 7.8 Hz)? 7.53 (1H5U = 7·8 Ηζ), 7·60 (lH, d, J =: 7.8 Hz), 7.91 (lH, brs), 8.19 (2H, d, J = 8.7 Hz). [Implementation ^9-9] [3 - [(2,6-dimercapto-4-tetrafluoroisopropylphenyl)amino]yl]benzyl]4-chlorophenyl; (Production of Compound No. φ produced by the implementation of j 8-2 Ν-(2,6-didecyl- 4-7 fluoroisopropyl)phenyl 3-aminobenzamide oxime. 30 g added to pyridine 5 m 4 g of 4-chlorobenzenesulfonyl chloride was placed in a solution of 1 and stirred at room temperature for 2 hours. Then, ethyl acetate was added, and then poured into ice water. The aqueous phase was made acidic using > The organic phase was separated, washed twice with saturated aqueous sodium hydrogen sulfate solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (hexane: ethyl acetate = 2) : 1) Refining to give the title compound 0.30 g (yield: 70%) of a color of amorphous material. 'H. NMR CCDCls) 5 2.29 (6H5s) ? 7.32 - Ί. 39 (6H?m)? 7.58 - 7.66 (6H, m) [Example 10-1] 4-(1,1,2,3,3,3-hexafluoropropoxy)-nitrobenzene was prepared by p-nitrophenol 4.63 g and potassium hydroxide 0 56 g After adding hexafluoropropane to a solution of N,N-didecylguanamine lOjril, it was stirred at 5 (rc for 1 hour). Then, after adding ethyl acetate and water, the organic phase was separated. The organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated, evaporated, mjjjjjjjjj 42%) yellow oil. H-NMR (CDCls) δ 5.06 (lH5ddtJ=44.05lL255.2Hz) 57.39 (2H?d5J = 8·8Ηζ), 8·30 (2H, d, J = 8.8 Hz). Example 10-2] Preparation of 4~(U,2,3,3,3-hexafluoropropoxy)monoaniline 甩4(1,1,2,353,3~hexafluoropropoxy)-nitrogen The title compound was obtained as an oil of the title compound (CDCI3) δ 3·69 (2H, brs), 4·% (lH, dddcU = 44·0, 11·········· 2, 11.2, 5. 6 Ηζ), 6.64 (2H, d, J = & 8 Hz), 6.98 (2H5d, J = 8.8 Hz). [Example 10-3] Preparation of 2,6-dibromo-4-iso(1,1,2,3,3,3-hexafluoropropoxy)-aniline using N-bromo acid to make imine 2 equivalents The title compound oil was obtained according to the conditions described in Example 1-1. 'H-NMR (CDCI3) δ 4.51 (2H, brS), 4.96 (lH, dddd, J = 44·0, 11·2, 11·2, 6·0Ηζ), 7.30 (2H, s) 0
[實施例 10 — 4] N—(2,6 — 二溴一4 —(1,1,2,3,3,3 —六氟丙氧 基)苯基)3 —硝基苯曱酿胺之製造 依照實施例1一2記載之條件,製造標題化合物固體。 Ή-NMR (CDCI3) δ 5.01 (lH?brd9J = 44.0Ht;)57.52 (lH s)7 57 - 7/78 (2198Η,πι),8·13 (lH,d,J = 7·6Ηζ),8·32 — 8·38 (2Hm)8 65 (lH,s) 〇 ,,.[Example 10 - 4] N-(2,6-dibromo- 4 -(1,1,2,3,3,3-hexafluoropropoxy)phenyl)-3-nitrophenyl hydrazone The title compound solid was produced according to the conditions described in Example 1 and 2. Ή-NMR (CDCI3) δ 5.01 (lH?brd9J = 44.0Ht;) 57.52 (lH s)7 57 - 7/78 (2198 Η, πι), 8·13 (lH, d, J = 7.6 Ηζ), 8 ·32 — 8·38 (2Hm)8 65 (lH,s) 〇,,.
[實施例 10 —5] Ν—(2,6—二溴一4一(1,1,2,3,3,3 —六氟丙氧 基)苯基)3 —胺基苯曱醢胺之製造 依照實施例1一3記載之條件,得到標題化合物固體。 'H-NMR (DMSO - d6) (5 5.18 (2H?brs)?626 (lH?brdJ = 44,0HzX6.80(lH9dJ=6.4Hz)57.14 (2H5tJ=7e 6Hz)57 20 ΠΗς^7 6λ (2H,s),KU4(lH,s)。 V 9 Λ [實施例 1()-6] N-(2,6—二溴—4 —(151,2,3,3,3 —六氣 基)3-[(2-氟笨甲醯基)胺基]苯曱醯胺(化合物編號2一幻之 製造 依照實施例I-4記載之條件,得到標題化合 ^H-NMR (CDCI3) 5 5.01 (1H,brd,J==4 4.0Hz),7 HdJ_ 8.0卿.42 _,卜7夠,7·52_7‘55 ( =: 7.6Ηζ),7.δ2一(4H,d,J==8,0Hz),8,02 (2H,S),8 25 (2H j),。八邱 其次,顯示本發明之代表性製劃,但本發明稀於該等。又, 167 200836629 製劑例中,「份」表示「重量份」。 製劑例1 (粉劑) 將5份化合物2—167及黏土 94.5份、Driless B(三共(股)公司)〇 5 份均勻地混合粉碎,得到含有效成分5%之粉劑。 製劑例2 (可濕性粉劑) 將50份化合物1 一306、木質素石黃酸納1份、白煙5份及石夕藻土 44份混合粉碎,得到含有效成分50%之可濕性粉劑。 製劑例3 (水懸劑) 將20份化合物1 一 187、丙二醇5份、聚氧乙烯油酸酯5份、聚氧 乙烯二烯丙基醚硫酸酯5份、矽系消泡劑0.2份及水64·8份,以 砂磨機濕式粉碎,得到有效成分20%之水懸劑。 製劑例4 (乳劑) 將10份化合物2 —167、環己烷10份、二曱苯60份、及Sorpol(東 邦化學製界面活性劑)2〇份均勻地溶解混合,得到含有效成分1〇0/。 之乳劑。 製劑例5 (顆粒可濕性粉劑) 將20份化合物1一3〇6、CMc鈉3份、烷基硫酸酯5份、黏土 72 份均勻混合後,加水混練、造粒、乾燥、整粒,得到含有效成分 20%之顆粒可濕性粉劑。以下顯示本發明之生物試驗例,但本發明 不限於該等。又,以下試驗例中,除使用表中記載之化合物以外, 並與製劑例2同樣地製備可濕性粉劑,再與製劑例3同樣地製備 水懸劑。 [試驗例1 ]對甜菜之葉蚤之防治效果 將選$藥量之可濕性粉劑以種子包衣(dressing)機(於旋轉鼓内喷身^ 化學藥品溶液)處理。處理45日後,檢查葉蚤導致之食害程度才曰 數二並計算防治率。又,亦可肉眼調查藥害之有無。結果如表6 所示。食害程度與指數如下所述: 指數0 :無食害、 指數1:食害程度少、 200836629 指數2:食害程度中、 指數3:食害程度多 防治率= 100—((lx指數1之食害數+ 2x指數2食害數+ 3χ指數3 食害數)/3χ總調査數xlOO) 表6 供試藥劑 處理藥量 (g ai/100000 種子) 防治率(%) 藥害 化合物6-12 50 99 益 #、、、 達特南 (dinotefuran) 50 99 益 無處理區 --—--- 0_— Ml --------[Example 10-5] Ν-(2,6-dibromo-4-iso(1,1,2,3,3,3-hexafluoropropoxy)phenyl)3-aminophenylamine The title compound solid was obtained according to the conditions described in Example 1 to 3. 'H-NMR (DMSO - d6) (5 5.18 (2H?brs)?626 (lH?brdJ = 44,0HzX6.80 (lH9dJ=6.4Hz) 57.14 (2H5tJ=7e 6Hz) 57 20 ΠΗς^7 6λ (2H , s), KU4 (lH, s). V 9 Λ [Example 1 ()-6] N-(2,6-dibromo-4-(-, 151, 2, 3, 3, 3 - hexa) 3-[(2-Fluorobenzoyl)amino]benzamide (Compound No. 2, phantom was produced according to the conditions described in Example I-4 to give the title compound H-NMR (CDCI3) 5 5.01 ( 1H, brd, J==4 4.0Hz), 7 HdJ_ 8.0 Qing.42 _, Bu 7 is enough, 7·52_7'55 ( =: 7.6Ηζ), 7.δ2 one (4H, d, J==8, 0 Hz), 8, 02 (2H, S), 8 25 (2H j), 八邱, followed by a representative scheme of the present invention, but the present invention is sparsely used. Further, 167 200836629 In the preparation example, "Parts" means "parts by weight." Formulation Example 1 (Powder) 5 parts of compound 2-167 and 94.5 parts of clay and Driless B (Sankyo Co., Ltd.) 5 parts were uniformly mixed and pulverized to obtain 5% of active ingredient. Formulation Example 2 (Wettable powder) 50 parts of Compound 1 - 306, 1 part of lignin, 1 part of white smoke, and 44 parts of Shixia Earth are mixed and pulverized to obtain 50% of active ingredient. Wet powder Formulation Example 3 (aqueous suspension) 20 parts of Compound 1 - 187, 5 parts of propylene glycol, 5 parts of polyoxyethylene oleate, 5 parts of polyoxyethylene diallyl ether sulfate, 0.2 parts of an antifoaming agent, and 64 parts of water, wet-grinding with a sand mill to obtain an aqueous suspension of 20% of the active ingredient. Formulation Example 4 (emulsion) 10 parts of compound 2-167, 10 parts of cyclohexane, 60 parts of diphenylbenzene, And 2 parts of Sorpol (manufactured by Toho Chemical Co., Ltd.) were uniformly dissolved and mixed to obtain an emulsion containing the active ingredient of 1 〇 0 /. Formulation Example 5 (Particle wettable powder) 20 parts of Compound 1 - 3 〇 6, 3 parts of CMc sodium, 5 parts of alkyl sulfate, and 72 parts of clay are uniformly mixed, and then mixed with water, granulated, dried, and granulated to obtain a granule wettable powder containing 20% of the active ingredient. The biological test of the present invention is shown below. In the following test examples, a wettable powder was prepared in the same manner as in Formulation Example 2 except that the compound described in the Table was used, and an aqueous suspension was prepared in the same manner as in Preparation Example 3. [Test Example 1] The control effect on the leaf beet of the beet will be selected as the dose of the wettable powder as a seed. Clothing (dressing) machine (in the rotating drum body ^ chemical spray solution) processing for 45 days, check the cause of the food leaves flea extent of damage was calculated and Prevention said two's rate. In addition, the presence or absence of phytotoxicity can also be investigated with the naked eye. The results are shown in Table 6. The degree of eclipse and index are as follows: Index 0: no food, index 1: less taint, 200836629 index 2: degree of eclipse, index 3: degree of eclipse prevention = 100-((lx index 1 of the number of food + 2x) Index 2 number of foods + 3χ index 3 number of foods) / 3χ total number of surveys xlOO) Table 6 dose of test agent (g ai/100000 seeds) control rate (%) phytotoxic compounds 6-12 50 99 benefits #,, , dinotefuran 50 99 benefit no treatment area ----- 0-- Ml --------
h式3對於紅豆象鼻蟲之防治效果 ^ ΐΐϊϊΐ水,對於紅豆1kg進行20ml塗抹處理。風乾後, 3 ^月刀Γ,南腰培養皿,並放置於坑怪溫室。處理2、及 複)。放詞2日ΐ象t早成蟲於各高腰培養皿放飼1〇隻(5重 結果如所‘周查死触數及在紅豆之齡數,計算死蟲率。 死蟲率=(處理區之死亡蟲數/50隻)χι〇〇 169 200836629 表7 供試藥劑 處理藥量 (g ai/kg 種子) 處理2個月後 處理3個月後 死蟲率 (%) 產下卵 數/竿 隻 死蟲率 (%) 產下卵 數/竿 隻 化合物1-306 5 100 0 100 0 化合物2-163 5 100 0 100 0 化合物6-8 5 100 0 100 0 化合物6-12 5 100 0 100 0 達特南 5 100 0 100 0 無處理區 0 12.0 0 11.5 [試驗例3]玉米之蕪菁夜蛾防治試驗 將選定藥量之可濕性粉劑對於玉米種子5g進行粉衣處理。於 l/10000a缽播種經藥劑處理之種子5粒,於播種9日後放入蕪菁 夜蛾3齡幼蟲10隻,並且掛網(2重複)。放蟲5日後檢查生死, 並計算死蟲率。結果如表8所示。h type 3 for the control effect of red bean weevil ^ ΐΐϊϊΐ水, for the red bean 1kg 20ml smear treatment. After air drying, 3 ^ knives, south of the petri dish, and placed in the pit strange greenhouse. Process 2, and complex). On the 2nd day, the early adult worms were fed 1 〇 in each high-waist petri dish (5 results were calculated as the number of dead touches and the number of red beans in the week, and the mortality rate was calculated. Number of dead insects in the area / 50) χι〇〇169 200836629 Table 7 Dosing amount of test agent (g ai / kg seed) Dead insect rate after 3 months of treatment after 2 months of treatment (%) Number of eggs laid /竿 only dead insect rate (%) number of eggs laid / 竿 compound only 1-306 5 100 0 100 0 compound 2-163 5 100 0 100 0 compound 6-8 5 100 0 100 0 compound 6-12 5 100 0 100 0 Datnam 5 100 0 100 0 No treatment area 0 12.0 0 11.5 [Test Example 3] Corn phthalocyanine control experiment The selected amount of wettable powder was subjected to powder coating treatment for 5 g of corn seeds.钵 Seeding 5 seeds treated with the drug, 10 seeds of the 3rd instar larvae of the genus Spodoptera were placed after 9 days of sowing, and the net was hanged (2 repeats). After 5 days of larvae, the life and death were checked, and the mortality rate was calculated. Shown.
170 200836629 表8 供試藥劑 處理藥量 (mg ai/種子) 死蟲率(%) 藥害 化合物1-159 20 100 益 化合物1-306 20 100 無 化合物2_159 20 100 無 化合物2-163 20 100 無 化合物4-1 20 100 無 化合物5-9 20 100 無 化合物6-8 20 100 無 化合物6-9 20 100 無 化合物6-12 20 100 無 益達胺(imidacloprid) 20 100 無 無處理區 10 無 【圖式簡單說明】 無0170 200836629 Table 8 Dosing amount of test agent (mg ai/seed) Dead insect rate (%) Phytotoxicity compound 1-159 20 100 Benefit compound 1-306 20 100 No compound 2_159 20 100 No compound 2-163 20 100 None Compound 4-1 20 100 No compound 5-9 20 100 No compound 6-8 20 100 No compound 6-9 20 100 No compound 6-12 20 100 Unidacloprid 20 100 No treatment zone 10 No [Figure Simple description] no 0
【主要元件符號說明】 無。 171[Main component symbol description] None. 171
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006340923A JP2010047480A (en) | 2006-12-19 | 2006-12-19 | Method for preventing insect damage |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200836629A true TW200836629A (en) | 2008-09-16 |
Family
ID=39536105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW96148242A TW200836629A (en) | 2006-12-19 | 2007-12-17 | Insecticidal composition for seeds or harvested crops and method for using the same |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2010047480A (en) |
| AR (1) | AR064401A1 (en) |
| CL (1) | CL2007003717A1 (en) |
| TW (1) | TW200836629A (en) |
| WO (1) | WO2008075465A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115868499A (en) * | 2022-12-12 | 2023-03-31 | 中农立华生物科技股份有限公司 | A kind of compound agricultural insecticide containing bromflubendiamide and its application |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2072501A1 (en) * | 2007-12-21 | 2009-06-24 | Bayer CropScience AG | Aminobenzamide derivatives as useful agents for controlling animal parasites |
| AU2009280679B2 (en) * | 2008-08-13 | 2012-07-26 | Mitsui Chemicals Crop & Life Solutions, Inc. | Amide derivative, pest control agent containing the amide derivative and use of the pest control agent |
| EP2322502B1 (en) | 2008-08-13 | 2019-09-18 | Mitsui Chemicals Agro, Inc. | Method for producing amide derivative |
| EP2394986B1 (en) | 2009-02-06 | 2013-12-04 | Agro-Kanesho Co., Ltd. | 3-aminoxalylaminobenzamide derivatives, and insecticidal and miticidal agents containing same as active ingredient |
| CN104245665B (en) * | 2012-04-03 | 2017-08-25 | 三井化学Agro株式会社 | The manufacture method of alkylated aromatic amide derivatives |
| CN102993054B (en) * | 2012-10-24 | 2015-02-18 | 中化蓝天集团有限公司 | Benzamide derivative and preparation method and application thereof |
| EP3556744B1 (en) | 2013-12-23 | 2022-06-01 | Syngenta Participations AG | Insecticidal compounds |
| BR112022004495A8 (en) * | 2019-09-12 | 2023-04-18 | Jiangxi Jemincare Group Co Ltd | PYRIDINE OXINITIDE COMPOUNDS, PHARMACEUTICAL COMPOSITION INCLUDING THE SAME AND USES THEREOF |
| TW202523302A (en) | 2023-11-02 | 2025-06-16 | 美商阿克思生物科學有限公司 | Thiazole compounds and methods of use thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR122015015718B1 (en) * | 2004-01-28 | 2016-05-10 | Mitsui Chemicals Inc | amide derivatives |
| JP2006306771A (en) * | 2005-04-28 | 2006-11-09 | Mitsui Chemicals Inc | Agricultural/horticultural insecticide |
| MX295245B (en) * | 2005-06-21 | 2012-01-26 | Mitsui Chemicals Inc | Amide derivative and pesticide containing such compound. |
| WO2006137395A1 (en) * | 2005-06-23 | 2006-12-28 | Mitsui Chemicals, Inc. | Amide derivative, pesticide containing such compound and use thereof |
| JP4580836B2 (en) * | 2005-07-25 | 2010-11-17 | 三井化学アグロ株式会社 | Insecticidal composition |
| CA2616749C (en) * | 2005-07-27 | 2012-01-03 | Mitsui Chemicals, Inc. | Composition for preventing harmful organisms |
| JP2007031395A (en) * | 2005-07-29 | 2007-02-08 | Bayer Cropscience Ag | Insecticidal 3-acylaminobenzanilide |
| JP2007099761A (en) * | 2005-09-08 | 2007-04-19 | Mitsui Chemicals Inc | Amide derivative and application method thereof as insecticide |
| WO2007083394A1 (en) * | 2006-01-19 | 2007-07-26 | Mitsui Chemicals, Inc. | Pest control composition containing diamine derivative |
-
2006
- 2006-12-19 JP JP2006340923A patent/JP2010047480A/en active Pending
-
2007
- 2007-12-17 TW TW96148242A patent/TW200836629A/en unknown
- 2007-12-18 AR ARP070105677 patent/AR064401A1/en not_active Application Discontinuation
- 2007-12-19 WO PCT/JP2007/001424 patent/WO2008075465A1/en not_active Ceased
- 2007-12-19 CL CL2007003717A patent/CL2007003717A1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115868499A (en) * | 2022-12-12 | 2023-03-31 | 中农立华生物科技股份有限公司 | A kind of compound agricultural insecticide containing bromflubendiamide and its application |
Also Published As
| Publication number | Publication date |
|---|---|
| AR064401A1 (en) | 2009-04-01 |
| CL2007003717A1 (en) | 2008-04-18 |
| JP2010047480A (en) | 2010-03-04 |
| WO2008075465A1 (en) | 2008-06-26 |
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