BG62809B1 - (4,4-дифлуоробут-3-енилтио)-заместени хетероциклени иликарбоциклени пръстенни съединения с пестицидна активност - Google Patents
(4,4-дифлуоробут-3-енилтио)-заместени хетероциклени иликарбоциклени пръстенни съединения с пестицидна активност Download PDFInfo
- Publication number
- BG62809B1 BG62809B1 BG100900A BG10090096A BG62809B1 BG 62809 B1 BG62809 B1 BG 62809B1 BG 100900 A BG100900 A BG 100900A BG 10090096 A BG10090096 A BG 10090096A BG 62809 B1 BG62809 B1 BG 62809B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- optionally substituted
- alkyl
- sch
- halogen
- vii
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 392
- -1 4,4-difluorobut-3-enylthio Chemical group 0.000 title claims description 156
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 8
- 230000000361 pesticidal effect Effects 0.000 title claims 5
- 125000002837 carbocyclic group Chemical group 0.000 title claims 2
- 125000001424 substituent group Chemical group 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 7
- 238000002360 preparation method Methods 0.000 claims description 149
- 239000000203 mixture Substances 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 97
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000005108 alkenylthio group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
- 125000006788 haloalkenyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- 241000244206 Nematoda Species 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 2
- 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 2
- 235000009508 confectionery Nutrition 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 239000000642 acaricide Substances 0.000 claims 1
- 125000005109 alkynylthio group Chemical group 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 336
- 238000005160 1H NMR spectroscopy Methods 0.000 description 291
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 262
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 244
- 239000003921 oil Substances 0.000 description 244
- 235000019198 oils Nutrition 0.000 description 244
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 168
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 153
- 239000000243 solution Substances 0.000 description 134
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 110
- 239000011541 reaction mixture Substances 0.000 description 110
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 102
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 97
- 239000000047 product Substances 0.000 description 83
- 239000007787 solid Substances 0.000 description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 62
- 239000012074 organic phase Substances 0.000 description 59
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 56
- 238000004587 chromatography analysis Methods 0.000 description 53
- 239000010410 layer Substances 0.000 description 52
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
- 238000005481 NMR spectroscopy Methods 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- 239000007800 oxidant agent Substances 0.000 description 44
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 42
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000003480 eluent Substances 0.000 description 41
- 239000000377 silicon dioxide Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 39
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
- 230000001590 oxidative effect Effects 0.000 description 34
- 239000011780 sodium chloride Substances 0.000 description 31
- 239000000706 filtrate Substances 0.000 description 28
- 229910000027 potassium carbonate Inorganic materials 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- 238000001704 evaporation Methods 0.000 description 26
- 230000008020 evaporation Effects 0.000 description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 26
- 229920006395 saturated elastomer Polymers 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
- 235000019341 magnesium sulphate Nutrition 0.000 description 24
- WSIDFIREQDHYPW-UHFFFAOYSA-N 4-bromo-1,1-difluorobut-1-ene Chemical compound FC(F)=CCCBr WSIDFIREQDHYPW-UHFFFAOYSA-N 0.000 description 23
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 238000001914 filtration Methods 0.000 description 21
- 239000007788 liquid Substances 0.000 description 21
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 238000000746 purification Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 238000004817 gas chromatography Methods 0.000 description 16
- 239000012299 nitrogen atmosphere Substances 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- HXQIFAAGEIMFHS-UHFFFAOYSA-N 4,4-difluorobut-3-enyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCC=C(F)F)C=C1 HXQIFAAGEIMFHS-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 14
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 235000014121 butter Nutrition 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 229920000728 polyester Polymers 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 13
- CYICOSUAVXTZOD-UHFFFAOYSA-N 1,1-difluorobut-1-ene Chemical compound CCC=C(F)F CYICOSUAVXTZOD-UHFFFAOYSA-N 0.000 description 12
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000012414 tert-butyl nitrite Substances 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 8
- UNPJUIZHZWFYLY-UHFFFAOYSA-N 1,4-dibromo-1,1,2-trifluorobutane Chemical compound FC(Br)(F)C(F)CCBr UNPJUIZHZWFYLY-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 6
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 6
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical class SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 5
- IRBARTHUMXZAJR-UHFFFAOYSA-N 4-(4,4-difluorobut-3-enyldisulfanyl)-1,1-difluorobut-1-ene Chemical compound FC(F)=CCCSSCCC=C(F)F IRBARTHUMXZAJR-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 229910006095 SO2F Inorganic materials 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 101000941448 Lasioglossum laticeps Lasioglossin-2 Proteins 0.000 description 4
- 229910006074 SO2NH2 Inorganic materials 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- 229910003480 inorganic solid Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OMYOTPPJTUENQI-UHFFFAOYSA-N (4-bromo-4,4-difluorobutyl) methanesulfonate Chemical compound CS(=O)(=O)OCCCC(F)(F)Br OMYOTPPJTUENQI-UHFFFAOYSA-N 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
- JHWSCOBZLASJKQ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4,5-dimethyl-1h-imidazole Chemical compound CC=1N=C(SCCC=C(F)F)NC=1C JHWSCOBZLASJKQ-UHFFFAOYSA-N 0.000 description 3
- BCHPFJXZQWWCCZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetohydrazide Chemical compound COC1=CC=C(CC(=O)NN)C=C1 BCHPFJXZQWWCCZ-UHFFFAOYSA-N 0.000 description 3
- PELIJVQFPYPWOG-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid;magnesium Chemical compound [Mg].OOC(=O)C1=CC=CC=C1C(O)=O PELIJVQFPYPWOG-UHFFFAOYSA-N 0.000 description 3
- SLXQRAMAAPBUQJ-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid;magnesium;hexahydrate Chemical compound O.O.O.O.O.O.[Mg].OOC(=O)C1=CC=CC=C1C(O)=O SLXQRAMAAPBUQJ-UHFFFAOYSA-N 0.000 description 3
- QPHZWABVAIGWHI-UHFFFAOYSA-N 3-methyl-2h-1,2,4-thiadiazole-5-thione Chemical compound CC1=NSC(S)=N1 QPHZWABVAIGWHI-UHFFFAOYSA-N 0.000 description 3
- KLUJJBZDBBYZEJ-UHFFFAOYSA-N 3-phenyl-2h-1,2,4-oxadiazole-5-thione Chemical compound N1OC(=S)N=C1C1=CC=CC=C1 KLUJJBZDBBYZEJ-UHFFFAOYSA-N 0.000 description 3
- 101100234822 Caenorhabditis elegans ltd-1 gene Proteins 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 241000400611 Eucalyptus deanei Species 0.000 description 3
- 239000012425 OXONE® Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 3
- FAMFBFJWKFYYLG-UHFFFAOYSA-M sodium;sulfanide;dihydrate Chemical compound O.O.[Na+].[SH-] FAMFBFJWKFYYLG-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- NUSVDASTCPBUIP-UHFFFAOYSA-N (5-bromo-1,3-thiazol-2-yl)azanium;bromide Chemical compound [Br-].BrC1=C[NH2+]C(=N)S1 NUSVDASTCPBUIP-UHFFFAOYSA-N 0.000 description 2
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 2
- XUNLTYLWCMUZFO-UHFFFAOYSA-N 1,4-dihydropyrazine-2,3-dithione Chemical compound S=C1NC=CNC1=S XUNLTYLWCMUZFO-UHFFFAOYSA-N 0.000 description 2
- LFDJCWRYXCAVSC-UHFFFAOYSA-N 1-(difluoromethyl)-4-phenylmethoxybenzene Chemical compound C1=CC(C(F)F)=CC=C1OCC1=CC=CC=C1 LFDJCWRYXCAVSC-UHFFFAOYSA-N 0.000 description 2
- GCTFDMFLLBCLPF-UHFFFAOYSA-N 2,5-dichloropyridine Chemical compound ClC1=CC=C(Cl)N=C1 GCTFDMFLLBCLPF-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- VSXFCGSZFMLOCV-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1-phenylimidazole Chemical compound FC(F)=CCCSC1=NC=CN1C1=CC=CC=C1 VSXFCGSZFMLOCV-UHFFFAOYSA-N 0.000 description 2
- BRWODPAZITZGHE-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-3-methyl-3h-1,2-oxazole Chemical compound CC1C=CON1SCCC=C(F)F BRWODPAZITZGHE-UHFFFAOYSA-N 0.000 description 2
- BTKAWPAUCMFMJA-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-phenyl-1,3,4-oxadiazole Chemical compound O1C(SCCC=C(F)F)=NN=C1C1=CC=CC=C1 BTKAWPAUCMFMJA-UHFFFAOYSA-N 0.000 description 2
- WQEQLOINEPESPW-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1h-imidazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NC=CN1 WQEQLOINEPESPW-UHFFFAOYSA-N 0.000 description 2
- GZCJODOFKJYPGE-UHFFFAOYSA-N 2-(4-bromo-3,4,4-trifluorobutyl)sulfanyl-1,3-thiazole Chemical compound FC(Br)(F)C(F)CCSC1=NC=CS1 GZCJODOFKJYPGE-UHFFFAOYSA-N 0.000 description 2
- DWJFRFBPUVKFIK-UHFFFAOYSA-N 2-(4-bromo-3,4,4-trifluorobutyl)sulfanyl-5-chloro-1,3-thiazole Chemical compound FC(Br)(F)C(F)CCSC1=NC=C(Cl)S1 DWJFRFBPUVKFIK-UHFFFAOYSA-N 0.000 description 2
- NIRIRNJHTXPNAE-UHFFFAOYSA-N 2-(4-bromo-4,4-difluorobutyl)sulfanylquinoxaline Chemical compound C1=CC=CC2=NC(SCCCC(F)(Br)F)=CN=C21 NIRIRNJHTXPNAE-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- LYQVWIGJCIZDLH-UHFFFAOYSA-N 2-amino-n,n-diethyl-4-methyl-1,3-thiazole-5-sulfonamide Chemical compound CCN(CC)S(=O)(=O)C=1SC(N)=NC=1C LYQVWIGJCIZDLH-UHFFFAOYSA-N 0.000 description 2
- UBIVTQXICGIZQL-UHFFFAOYSA-N 2-chloro-3-(4,4-difluorobut-3-enylsulfanyl)pyrazine Chemical compound FC(F)=CCCSC1=NC=CN=C1Cl UBIVTQXICGIZQL-UHFFFAOYSA-N 0.000 description 2
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 2
- GUPOZVHRTJYZCX-UHFFFAOYSA-N 2-chloroethanimidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])CCl GUPOZVHRTJYZCX-UHFFFAOYSA-N 0.000 description 2
- MTEZLAATISORQK-UHFFFAOYSA-N 2-methoxyacetamide Chemical compound COCC(N)=O MTEZLAATISORQK-UHFFFAOYSA-N 0.000 description 2
- BNBOUFHCTIFWHN-UHFFFAOYSA-N 3-bromobutan-2-one Chemical compound CC(Br)C(C)=O BNBOUFHCTIFWHN-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- FXQINRXVWWPGIQ-UHFFFAOYSA-N 3-methyl-1h-pyridazine-6-thione Chemical compound CC1=CC=C(S)N=N1 FXQINRXVWWPGIQ-UHFFFAOYSA-N 0.000 description 2
- CLEJZSNZYFJMKD-UHFFFAOYSA-N 3h-1,3-oxazole-2-thione Chemical class SC1=NC=CO1 CLEJZSNZYFJMKD-UHFFFAOYSA-N 0.000 description 2
- VTKPCJPWPLLANV-UHFFFAOYSA-N 4,4-difluorobut-3-enylthiourea Chemical compound NC(=S)NCCC=C(F)F VTKPCJPWPLLANV-UHFFFAOYSA-N 0.000 description 2
- XCKCJBYLJUVVFX-UHFFFAOYSA-N 4,4-difluorobut-3-enylthiourea hydrobromide Chemical compound Br.NC(=S)NCCC=C(F)F XCKCJBYLJUVVFX-UHFFFAOYSA-N 0.000 description 2
- GQCQMFYIFUDARF-UHFFFAOYSA-N 4-bromo-1,1,2-trifluorobut-1-ene Chemical compound FC(F)=C(F)CCBr GQCQMFYIFUDARF-UHFFFAOYSA-N 0.000 description 2
- YMVXWKFHZLGKAX-UHFFFAOYSA-N 4-bromo-4,4-difluorobutan-1-ol Chemical compound OCCCC(F)(F)Br YMVXWKFHZLGKAX-UHFFFAOYSA-N 0.000 description 2
- YAIWEWFNTHJMTH-UHFFFAOYSA-N 4-bromo-4,4-difluorobutanoic acid Chemical compound OC(=O)CCC(F)(F)Br YAIWEWFNTHJMTH-UHFFFAOYSA-N 0.000 description 2
- PDJNXKAXJVMDEA-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole Chemical compound FC(F)=CCCSC1=CN=CS1 PDJNXKAXJVMDEA-UHFFFAOYSA-N 0.000 description 2
- LZAFNGDEHZAJGE-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-(methoxymethyl)-1,2,4-oxadiazole Chemical compound COCC1=NOC(SCCC=C(F)F)=N1 LZAFNGDEHZAJGE-UHFFFAOYSA-N 0.000 description 2
- PMQIFKWGNDEIEI-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-methyl-1,2,4-thiadiazole Chemical compound CC1=NSC(SCCC=C(F)F)=N1 PMQIFKWGNDEIEI-UHFFFAOYSA-N 0.000 description 2
- ZWRRSXUUNSEESM-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfonyl)-3-(methoxymethyl)-1,2,4-thiadiazole Chemical compound COCC1=NSC(S(=O)(=O)CCC=C(F)F)=N1 ZWRRSXUUNSEESM-UHFFFAOYSA-N 0.000 description 2
- RZPRZUXOUCYTCD-UHFFFAOYSA-N 5-(methoxymethyl)-1,3,4-oxathiazol-2-one Chemical compound COCC1=NSC(=O)O1 RZPRZUXOUCYTCD-UHFFFAOYSA-N 0.000 description 2
- QDNSOIVVERSXFB-UHFFFAOYSA-N 5-bromo-2-(4,4-difluorobut-3-enylsulfonyl)-1,3-thiazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NC=C(Br)S1 QDNSOIVVERSXFB-UHFFFAOYSA-N 0.000 description 2
- TYAFGWLDDNPWAI-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole Chemical compound FC(F)=CCCSC1=NC=C(Cl)S1 TYAFGWLDDNPWAI-UHFFFAOYSA-N 0.000 description 2
- HIVXKHNQVYARIS-UHFFFAOYSA-N 5-chloro-3-(4,4-difluorobut-3-enylsulfanylmethyl)-1,2,4-thiadiazole Chemical compound FC(F)=CCCSCC1=NSC(Cl)=N1 HIVXKHNQVYARIS-UHFFFAOYSA-N 0.000 description 2
- IFRYKIFAMMXTOF-UHFFFAOYSA-N 5-chloro-3-methylsulfanyl-1,2,4-thiadiazole Chemical compound CSC1=NSC(Cl)=N1 IFRYKIFAMMXTOF-UHFFFAOYSA-N 0.000 description 2
- ZVGKPQCCKGLQPB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-oxadiazole-2-thione Chemical compound CC1=NN=C(S)O1 ZVGKPQCCKGLQPB-UHFFFAOYSA-N 0.000 description 2
- OKGRCDVKEPEXFQ-UHFFFAOYSA-N 5-phenyl-3h-1,3-oxazole-2-thione Chemical compound O1C(S)=NC=C1C1=CC=CC=C1 OKGRCDVKEPEXFQ-UHFFFAOYSA-N 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- 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 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000005137 alkenylsulfonyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 2
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 2
- UJOUQMYCAIUSCJ-UHFFFAOYSA-N methyl 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-oxazole-5-carboxylate Chemical compound COC(=O)C=1OC(SCCC=C(F)F)=NC=1C UJOUQMYCAIUSCJ-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- XQRCJUSSMXAESW-UHFFFAOYSA-N n-[5-(diethylsulfamoyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound CCN(CC)S(=O)(=O)C=1SC(NC(C)=O)=NC=1C XQRCJUSSMXAESW-UHFFFAOYSA-N 0.000 description 2
- GWHGRVBLUKDFIE-UHFFFAOYSA-N o-(4,4-difluorobut-3-enyl) ethanethioate Chemical compound CC(=S)OCCC=C(F)F GWHGRVBLUKDFIE-UHFFFAOYSA-N 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 239000004296 sodium metabisulphite Substances 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ULYWPHZTECAHIG-UHFFFAOYSA-N (4-bromo-3,4,4-trifluorobutyl) 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCC(F)C(F)(F)Br)C=C1 ULYWPHZTECAHIG-UHFFFAOYSA-N 0.000 description 1
- JONIMGVUGJVFQD-UHFFFAOYSA-N (4-methylphenyl)sulfonylformonitrile Chemical compound CC1=CC=C(S(=O)(=O)C#N)C=C1 JONIMGVUGJVFQD-UHFFFAOYSA-N 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- BXTWCHHUJLDSHV-XFFZJAGNSA-N (NZ)-N-[2-(4,4-difluorobut-3-enylsulfanyl)-2H-thiophen-5-ylidene]hydroxylamine Chemical compound O\N=C1/SC(SCCC=C(F)F)C=C1 BXTWCHHUJLDSHV-XFFZJAGNSA-N 0.000 description 1
- NTCBUXIQMLORSI-GIDUJCDVSA-N (e)-1-[4-(4-bromophenyl)phenyl]-3-phenylprop-2-en-1-one Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C(=O)\C=C\C=2C=CC=CC=2)C=C1 NTCBUXIQMLORSI-GIDUJCDVSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- ZWVQALKXCUIWLJ-UHFFFAOYSA-N 1,2,4-oxadiazole-3-thione Chemical class SC=1N=CON=1 ZWVQALKXCUIWLJ-UHFFFAOYSA-N 0.000 description 1
- ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical compound NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 description 1
- XYYRQKIKWGLQAA-UHFFFAOYSA-N 1,3-oxazole-2-carbonyl chloride Chemical class ClC(=O)C1=NC=CO1 XYYRQKIKWGLQAA-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 description 1
- WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical compound SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 description 1
- OXGALYRXXIDWTH-UHFFFAOYSA-N 1-(4,4-difluorobut-3-enyl)-2-(4,4-difluorobut-3-enylsulfonyl)imidazole Chemical compound FC(F)=CCCN1C=CN=C1S(=O)(=O)CCC=C(F)F OXGALYRXXIDWTH-UHFFFAOYSA-N 0.000 description 1
- GZPUTCJLTUJOKJ-UHFFFAOYSA-N 1-(4,4-difluorobut-3-enylsulfanyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(SCCC=C(F)F)C=C1 GZPUTCJLTUJOKJ-UHFFFAOYSA-N 0.000 description 1
- FTSBMMQXZOPOIC-UHFFFAOYSA-N 1-[5-(4,4-difluorobut-3-enylsulfanyl)thiophen-2-yl]ethanone Chemical compound CC(=O)C1=CC=C(SCCC=C(F)F)S1 FTSBMMQXZOPOIC-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 1
- UPPPWUOZCSMDTR-UHFFFAOYSA-N 1-methyl-pyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C=N1 UPPPWUOZCSMDTR-UHFFFAOYSA-N 0.000 description 1
- HKAVADYDPYUPRD-UHFFFAOYSA-N 1h-pyrazine-2-thione Chemical compound SC1=CN=CC=N1 HKAVADYDPYUPRD-UHFFFAOYSA-N 0.000 description 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 1
- INQXGZFDGDSRIF-UHFFFAOYSA-N 1h-quinoxaline-2-thione Chemical compound C1=CC=CC2=NC(S)=CN=C21 INQXGZFDGDSRIF-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- WIUNZPQSTKZSJM-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-1h-pyridine-4-thione Chemical compound FC1=NC(F)=C(F)C(S)=C1F WIUNZPQSTKZSJM-UHFFFAOYSA-N 0.000 description 1
- MPQSTJVISXIDTJ-UHFFFAOYSA-N 2,3-bis(4,4-difluorobut-3-enylsulfanyl)pyrazine Chemical compound FC(F)=CCCSC1=NC=CN=C1SCCC=C(F)F MPQSTJVISXIDTJ-UHFFFAOYSA-N 0.000 description 1
- MLCNOCRGSBCAGH-UHFFFAOYSA-N 2,3-dichloropyrazine Chemical compound ClC1=NC=CN=C1Cl MLCNOCRGSBCAGH-UHFFFAOYSA-N 0.000 description 1
- KVYCLQBUDQGRGX-UHFFFAOYSA-N 2,5-bis(4,4-difluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCSC1=NN=C(SCCC=C(F)F)S1 KVYCLQBUDQGRGX-UHFFFAOYSA-N 0.000 description 1
- ILLBANIAGOKCOE-UHFFFAOYSA-N 2,5-bis(4,4-difluorobut-3-enylsulfinyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCS(=O)C1=NN=C(S(=O)CCC=C(F)F)S1 ILLBANIAGOKCOE-UHFFFAOYSA-N 0.000 description 1
- OGTYZLBILXZIOI-UHFFFAOYSA-N 2,5-bis(4,4-difluorobut-3-enylsulfonyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NN=C(S(=O)(=O)CCC=C(F)F)S1 OGTYZLBILXZIOI-UHFFFAOYSA-N 0.000 description 1
- LSEAAPGIZCDEEH-UHFFFAOYSA-N 2,6-dichloropyrazine Chemical compound ClC1=CN=CC(Cl)=N1 LSEAAPGIZCDEEH-UHFFFAOYSA-N 0.000 description 1
- XXIXOULFNXEWSF-UHFFFAOYSA-N 2-(2,6-difluorophenyl)acetohydrazide Chemical compound NNC(=O)CC1=C(F)C=CC=C1F XXIXOULFNXEWSF-UHFFFAOYSA-N 0.000 description 1
- DLGVXTQKEKRZDO-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCSC1=NN=CS1 DLGVXTQKEKRZDO-UHFFFAOYSA-N 0.000 description 1
- KFKLLBSHXXDROL-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,3-oxazole Chemical compound FC(F)=CCCSC1=NC=CO1 KFKLLBSHXXDROL-UHFFFAOYSA-N 0.000 description 1
- XCOMNPVCMVLUFW-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole Chemical compound FC(F)=CCCSC1=NC=CS1 XCOMNPVCMVLUFW-UHFFFAOYSA-N 0.000 description 1
- NAGBZLJWHDXYMW-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole-4-carbonitrile Chemical compound FC(F)=CCCSC1=NC(C#N)=CS1 NAGBZLJWHDXYMW-UHFFFAOYSA-N 0.000 description 1
- IHBAQMKOXUOLGT-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(SCCC=C(F)F)=N1 IHBAQMKOXUOLGT-UHFFFAOYSA-N 0.000 description 1
- ARTRYDLTWZLVNK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,4,5-trimethylimidazole Chemical compound CC=1N=C(SCCC=C(F)F)N(C)C=1C ARTRYDLTWZLVNK-UHFFFAOYSA-N 0.000 description 1
- AHWTVRQLNBLMQA-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,5-dimethylimidazole Chemical compound CC1=CN=C(SCCC=C(F)F)N1C AHWTVRQLNBLMQA-UHFFFAOYSA-N 0.000 description 1
- DEZNNFRYMUAHNB-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1-benzothiophene Chemical compound C1=CC=C2SC(SCCC=C(F)F)=CC2=C1 DEZNNFRYMUAHNB-UHFFFAOYSA-N 0.000 description 1
- RFJYZWQSMXPTFO-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1-ethylimidazole Chemical compound CCN1C=CN=C1SCCC=C(F)F RFJYZWQSMXPTFO-UHFFFAOYSA-N 0.000 description 1
- WTJWKRDFQDIDHW-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1-methylimidazole Chemical compound CN1C=CN=C1SCCC=C(F)F WTJWKRDFQDIDHW-UHFFFAOYSA-N 0.000 description 1
- BXKZCMQEGVHUCH-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1-propan-2-ylimidazole Chemical compound CC(C)N1C=CN=C1SCCC=C(F)F BXKZCMQEGVHUCH-UHFFFAOYSA-N 0.000 description 1
- KYUYBGMUBHOYTQ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1-propylimidazole Chemical compound CCCN1C=CN=C1SCCC=C(F)F KYUYBGMUBHOYTQ-UHFFFAOYSA-N 0.000 description 1
- NEIHMJRQIUWUPV-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1h-imidazole Chemical compound FC(F)=CCCSC1=NC=CN1 NEIHMJRQIUWUPV-UHFFFAOYSA-N 0.000 description 1
- VTECCXLVNQAUFZ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1SCCC=C(F)F VTECCXLVNQAUFZ-UHFFFAOYSA-N 0.000 description 1
- PKVFCALYTRJCBZ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4,5-dihydro-1,3-thiazole Chemical compound FC(F)=CCCSC1=NCCS1 PKVFCALYTRJCBZ-UHFFFAOYSA-N 0.000 description 1
- RHLZRFUJUYRIHO-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-(trifluoromethyl)-1,3-thiazole Chemical compound FC(F)=CCCSC1=NC(C(F)(F)F)=CS1 RHLZRFUJUYRIHO-UHFFFAOYSA-N 0.000 description 1
- OINDZIPVTSEYCD-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-ethyl-5-methyl-1h-imidazole Chemical compound CCC=1N=C(SCCC=C(F)F)NC=1C OINDZIPVTSEYCD-UHFFFAOYSA-N 0.000 description 1
- OYJNXBGWNMXYTI-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-oxazole Chemical compound CC1=COC(SCCC=C(F)F)=N1 OYJNXBGWNMXYTI-UHFFFAOYSA-N 0.000 description 1
- ZZOWHUMZLNPOEP-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-oxazole-5-carbonitrile Chemical compound CC=1N=C(SCCC=C(F)F)OC=1C#N ZZOWHUMZLNPOEP-UHFFFAOYSA-N 0.000 description 1
- STULZYHQQNEXJG-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-oxazole-5-carboxamide Chemical compound CC=1N=C(SCCC=C(F)F)OC=1C(N)=O STULZYHQQNEXJG-UHFFFAOYSA-N 0.000 description 1
- BVSVGDRVVVFWSV-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-oxazole-5-carboxylic acid Chemical compound CC=1N=C(SCCC=C(F)F)OC=1C(O)=O BVSVGDRVVVFWSV-UHFFFAOYSA-N 0.000 description 1
- YUVGDORNSDFUOV-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(SCCC=C(F)F)SC=1C(N)=O YUVGDORNSDFUOV-UHFFFAOYSA-N 0.000 description 1
- BVXYHQAJODKGHA-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=C(SCCC=C(F)F)SC=1C(O)=O BVXYHQAJODKGHA-UHFFFAOYSA-N 0.000 description 1
- AQKBJBXEBPMADI-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-thiazole-5-sulfonyl fluoride Chemical compound CC=1N=C(SCCC=C(F)F)SC=1S(F)(=O)=O AQKBJBXEBPMADI-UHFFFAOYSA-N 0.000 description 1
- ACGQMMUORZICCG-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1-propan-2-ylimidazole Chemical compound CC(C)N1C=C(C)N=C1SCCC=C(F)F ACGQMMUORZICCG-UHFFFAOYSA-N 0.000 description 1
- GQFANOLAVROKBT-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-(2-methoxyphenyl)-1,3,4-oxadiazole Chemical compound COC1=CC=CC=C1C1=NN=C(SCCC=C(F)F)O1 GQFANOLAVROKBT-UHFFFAOYSA-N 0.000 description 1
- VQHOZFMZFXEIKE-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-(2-methylpropyl)-1,3,4-oxadiazole Chemical compound CC(C)CC1=NN=C(SCCC=C(F)F)O1 VQHOZFMZFXEIKE-UHFFFAOYSA-N 0.000 description 1
- XPOPKDABROGGGK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C1=NN=C(SCCC=C(F)F)O1 XPOPKDABROGGGK-UHFFFAOYSA-N 0.000 description 1
- BEOYDAAKJQBVNA-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-(furan-2-yl)-1,3,4-oxadiazole Chemical compound O1C(SCCC=C(F)F)=NN=C1C1=CC=CO1 BEOYDAAKJQBVNA-UHFFFAOYSA-N 0.000 description 1
- ISDPPMVBONQCIK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-(furan-3-yl)-1,3,4-oxadiazole Chemical compound O1C(SCCC=C(F)F)=NN=C1C1=COC=C1 ISDPPMVBONQCIK-UHFFFAOYSA-N 0.000 description 1
- NRGPZPSVWMSRKD-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-(trifluoromethyl)pyridine Chemical compound FC(F)=CCCSC1=CC=C(C(F)(F)F)C=N1 NRGPZPSVWMSRKD-UHFFFAOYSA-N 0.000 description 1
- CWTHGTMHKUEREL-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-[(2,6-difluorophenyl)methyl]-1,3,4-oxadiazole Chemical compound O1C(SCCC=C(F)F)=NN=C1CC1=C(F)C=CC=C1F CWTHGTMHKUEREL-UHFFFAOYSA-N 0.000 description 1
- XVWNYZWVTMBPTD-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-[[3-(trifluoromethyl)phenyl]methylsulfanyl]-1,3,4-thiadiazole Chemical compound S1C(SCCC=C(F)F)=NN=C1SCC1=CC=CC(C(F)(F)F)=C1 XVWNYZWVTMBPTD-UHFFFAOYSA-N 0.000 description 1
- CHRJKLKKRWTFOJ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-ethyl-1,3,4-oxadiazole Chemical compound CCC1=NN=C(SCCC=C(F)F)O1 CHRJKLKKRWTFOJ-UHFFFAOYSA-N 0.000 description 1
- UFKIFPMAZSGDMD-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(SCCC=C(F)F)S1 UFKIFPMAZSGDMD-UHFFFAOYSA-N 0.000 description 1
- DVJCAVDLDOUTTJ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-methoxy-1,3,4-thiadiazole Chemical compound COC1=NN=C(SCCC=C(F)F)S1 DVJCAVDLDOUTTJ-UHFFFAOYSA-N 0.000 description 1
- INVBHEVOWTZZOA-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-methyl-1,3,4-oxadiazole Chemical compound CC1=NN=C(SCCC=C(F)F)O1 INVBHEVOWTZZOA-UHFFFAOYSA-N 0.000 description 1
- VEYIYGMXPTVOMQ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=C(SCCC=C(F)F)S1 VEYIYGMXPTVOMQ-UHFFFAOYSA-N 0.000 description 1
- OIUXROMBSOBBSY-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-methyl-1,3-thiazole Chemical compound CC1=CN=C(SCCC=C(F)F)S1 OIUXROMBSOBBSY-UHFFFAOYSA-N 0.000 description 1
- DSPUQJLPORLXHK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-methyl-1-propan-2-ylimidazole Chemical compound CC(C)N1C(C)=CN=C1SCCC=C(F)F DSPUQJLPORLXHK-UHFFFAOYSA-N 0.000 description 1
- KAGKIIKTJFYUDK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-methyl-1h-imidazole Chemical compound CC1=CNC(SCCC=C(F)F)=N1 KAGKIIKTJFYUDK-UHFFFAOYSA-N 0.000 description 1
- FUVIIWIUATUHMO-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-methylfuran Chemical compound CC1=CC=C(SCCC=C(F)F)O1 FUVIIWIUATUHMO-UHFFFAOYSA-N 0.000 description 1
- WGRFYDKEVWHSBM-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-methylsulfanyl-1,3,4-thiadiazole Chemical compound CSC1=NN=C(SCCC=C(F)F)S1 WGRFYDKEVWHSBM-UHFFFAOYSA-N 0.000 description 1
- KVELDVMPBPDURF-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(SCCC=C(F)F)N=C1 KVELDVMPBPDURF-UHFFFAOYSA-N 0.000 description 1
- JPMKCHRBIRUEFH-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-phenyl-1,3,4-thiadiazole Chemical compound S1C(SCCC=C(F)F)=NN=C1C1=CC=CC=C1 JPMKCHRBIRUEFH-UHFFFAOYSA-N 0.000 description 1
- WEAYWEPVWQNSMB-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-phenyl-1,3-oxazole Chemical compound O1C(SCCC=C(F)F)=NC=C1C1=CC=CC=C1 WEAYWEPVWQNSMB-UHFFFAOYSA-N 0.000 description 1
- LONHWVIWJISYCC-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-phenyl-1,3-thiazole Chemical compound S1C(SCCC=C(F)F)=NC=C1C1=CC=CC=C1 LONHWVIWJISYCC-UHFFFAOYSA-N 0.000 description 1
- BUPMDULILVNZIZ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-phenyl-1h-imidazole Chemical compound N1C(SCCC=C(F)F)=NC(C=2C=CC=CC=2)=C1 BUPMDULILVNZIZ-UHFFFAOYSA-N 0.000 description 1
- SRZIDCOYSUOVJL-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-propan-2-yl-1,3,4-oxadiazole Chemical compound CC(C)C1=NN=C(SCCC=C(F)F)O1 SRZIDCOYSUOVJL-UHFFFAOYSA-N 0.000 description 1
- GFGAFLOBAKYWGW-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-propan-2-yl-1,3,4-thiadiazole Chemical compound CC(C)C1=NN=C(SCCC=C(F)F)S1 GFGAFLOBAKYWGW-UHFFFAOYSA-N 0.000 description 1
- PYMAAAZMHUMWCK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-propyl-1,3,4-oxadiazole Chemical compound CCCC1=NN=C(SCCC=C(F)F)O1 PYMAAAZMHUMWCK-UHFFFAOYSA-N 0.000 description 1
- FCYYPYCTJXGPMK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-pyridin-4-yl-1,3,4-oxadiazole Chemical compound O1C(SCCC=C(F)F)=NN=C1C1=CC=NC=C1 FCYYPYCTJXGPMK-UHFFFAOYSA-N 0.000 description 1
- NWEFHGJLOQOXQV-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-5-thiophen-2-yl-1,3,4-oxadiazole Chemical compound O1C(SCCC=C(F)F)=NN=C1C1=CC=CS1 NWEFHGJLOQOXQV-UHFFFAOYSA-N 0.000 description 1
- BSXQNBVMZWTUPZ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-n,n-diethyl-4-methyl-1,3-thiazole-5-sulfonamide Chemical compound CCN(CC)S(=O)(=O)C=1SC(SCCC=C(F)F)=NC=1C BSXQNBVMZWTUPZ-UHFFFAOYSA-N 0.000 description 1
- PONXWJWVXNRPGL-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)furan Chemical compound FC(F)=CCCSC1=CC=CO1 PONXWJWVXNRPGL-UHFFFAOYSA-N 0.000 description 1
- VUQGMUBWLSVJAE-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)pyrazine Chemical compound FC(F)=CCCSC1=CN=CC=N1 VUQGMUBWLSVJAE-UHFFFAOYSA-N 0.000 description 1
- ZYQGLUWRLPZZJF-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)pyridine Chemical compound FC(F)=CCCSC1=CC=CC=N1 ZYQGLUWRLPZZJF-UHFFFAOYSA-N 0.000 description 1
- IXNQENCYCKCCGY-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)pyridine-3-carbonitrile Chemical compound FC(F)=CCCSC1=NC=CC=C1C#N IXNQENCYCKCCGY-UHFFFAOYSA-N 0.000 description 1
- QJRWWOQLIKRIOF-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)quinoxaline Chemical compound C1=CC=CC2=NC(SCCC=C(F)F)=CN=C21 QJRWWOQLIKRIOF-UHFFFAOYSA-N 0.000 description 1
- UGFRRWCIAVQDIK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)thiophene Chemical compound FC(F)=CCCSC1=CC=CS1 UGFRRWCIAVQDIK-UHFFFAOYSA-N 0.000 description 1
- NTOHTELINPABMH-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCS(=O)C1=NN=CS1 NTOHTELINPABMH-UHFFFAOYSA-N 0.000 description 1
- GAANIBQFUQZLMX-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-1,3-thiazole Chemical compound FC(F)=CCCS(=O)C1=NC=CS1 GAANIBQFUQZLMX-UHFFFAOYSA-N 0.000 description 1
- AYGCYXWTHWYEKX-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-1-benzothiophene Chemical compound C1=CC=C2SC(S(=O)CCC=C(F)F)=CC2=C1 AYGCYXWTHWYEKX-UHFFFAOYSA-N 0.000 description 1
- PWKVMCUXIJRFOS-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-1-methyl-4-phenylimidazole Chemical compound N1=C(S(=O)CCC=C(F)F)N(C)C=C1C1=CC=CC=C1 PWKVMCUXIJRFOS-UHFFFAOYSA-N 0.000 description 1
- SVWYZTZIQJHANU-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-(2-methylphenyl)-1,3,4-oxadiazole Chemical compound CC1=CC=CC=C1C1=NN=C(S(=O)CCC=C(F)F)O1 SVWYZTZIQJHANU-UHFFFAOYSA-N 0.000 description 1
- FQVRPPZSSTWVAY-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-(4,4-difluorobut-3-enylsulfonyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCS(=O)C1=NN=C(S(=O)(=O)CCC=C(F)F)S1 FQVRPPZSSTWVAY-UHFFFAOYSA-N 0.000 description 1
- YXWWWGOCAKKKKT-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C1=NN=C(S(=O)CCC=C(F)F)O1 YXWWWGOCAKKKKT-UHFFFAOYSA-N 0.000 description 1
- PUHQCOCVBKFOCT-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NN=C(S(=O)CCC=C(F)F)O1 PUHQCOCVBKFOCT-UHFFFAOYSA-N 0.000 description 1
- VTUJASRHUQASOK-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-[(4-methoxyphenyl)methyl]-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1CC1=NN=C(S(=O)CCC=C(F)F)O1 VTUJASRHUQASOK-UHFFFAOYSA-N 0.000 description 1
- WJXNGUGUDCSVIN-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(S(=O)CCC=C(F)F)S1 WJXNGUGUDCSVIN-UHFFFAOYSA-N 0.000 description 1
- HMBBVZFLXCLYLH-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=C(S(=O)CCC=C(F)F)S1 HMBBVZFLXCLYLH-UHFFFAOYSA-N 0.000 description 1
- YMNNCWNGKOEFJG-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-methyl-1,3-thiazole Chemical compound CC1=CN=C(S(=O)CCC=C(F)F)S1 YMNNCWNGKOEFJG-UHFFFAOYSA-N 0.000 description 1
- RMTBUJQIDYPBMQ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-phenyl-1,3-oxazole Chemical compound O1C(S(=O)CCC=C(F)F)=NC=C1C1=CC=CC=C1 RMTBUJQIDYPBMQ-UHFFFAOYSA-N 0.000 description 1
- FECPOZHMAGKVIG-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)-5-phenyl-1h-imidazole Chemical compound N1C(S(=O)CCC=C(F)F)=NC(C=2C=CC=CC=2)=C1 FECPOZHMAGKVIG-UHFFFAOYSA-N 0.000 description 1
- FJUZPJFQCRXNLJ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)furan Chemical compound FC(F)=CCCS(=O)C1=CC=CO1 FJUZPJFQCRXNLJ-UHFFFAOYSA-N 0.000 description 1
- JMYATHJPGQGIRF-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfinyl)thiophene Chemical compound FC(F)=CCCS(=O)C1=CC=CS1 JMYATHJPGQGIRF-UHFFFAOYSA-N 0.000 description 1
- VZDJJKVSCQSNNJ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NN=CS1 VZDJJKVSCQSNNJ-UHFFFAOYSA-N 0.000 description 1
- JWCGQJHNSQIZED-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1,3-thiazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NC=CS1 JWCGQJHNSQIZED-UHFFFAOYSA-N 0.000 description 1
- YYNRFRNWUHMPSF-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1,4,5-trimethylimidazole Chemical compound CC=1N=C(S(=O)(=O)CCC=C(F)F)N(C)C=1C YYNRFRNWUHMPSF-UHFFFAOYSA-N 0.000 description 1
- JOYXJOZRTPPOTG-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1,5-dimethylimidazole Chemical compound CC1=CN=C(S(=O)(=O)CCC=C(F)F)N1C JOYXJOZRTPPOTG-UHFFFAOYSA-N 0.000 description 1
- RNOKVTAWIWORLT-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1-benzothiophene Chemical compound C1=CC=C2SC(S(=O)(=O)CCC=C(F)F)=CC2=C1 RNOKVTAWIWORLT-UHFFFAOYSA-N 0.000 description 1
- KEVLOTVNRMHUGA-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1-ethyl-4,5-dimethylimidazole Chemical compound CCN1C(C)=C(C)N=C1S(=O)(=O)CCC=C(F)F KEVLOTVNRMHUGA-UHFFFAOYSA-N 0.000 description 1
- SYWRVJUUBSMFMO-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1-ethylimidazole Chemical compound CCN1C=CN=C1S(=O)(=O)CCC=C(F)F SYWRVJUUBSMFMO-UHFFFAOYSA-N 0.000 description 1
- DSWLSCMJRAFTQG-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1-methyl-4-phenylimidazole Chemical compound N1=C(S(=O)(=O)CCC=C(F)F)N(C)C=C1C1=CC=CC=C1 DSWLSCMJRAFTQG-UHFFFAOYSA-N 0.000 description 1
- AAWIGZNMDHIJHT-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1-phenylimidazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NC=CN1C1=CC=CC=C1 AAWIGZNMDHIJHT-UHFFFAOYSA-N 0.000 description 1
- NNYSKNZEKMHHNC-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-1-propan-2-ylimidazole Chemical compound CC(C)N1C=CN=C1S(=O)(=O)CCC=C(F)F NNYSKNZEKMHHNC-UHFFFAOYSA-N 0.000 description 1
- VJFKMFRQLHGZAG-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-4,5-dimethyl-1h-imidazole Chemical compound CC=1N=C(S(=O)(=O)CCC=C(F)F)NC=1C VJFKMFRQLHGZAG-UHFFFAOYSA-N 0.000 description 1
- TUOBCRVPJWGHLX-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-4-ethyl-5-methyl-1h-imidazole Chemical compound CCC=1N=C(S(=O)(=O)CCC=C(F)F)NC=1C TUOBCRVPJWGHLX-UHFFFAOYSA-N 0.000 description 1
- GSUNTOFGQYCPCU-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-4-methyl-1-propan-2-ylimidazole Chemical compound CC(C)N1C=C(C)N=C1S(=O)(=O)CCC=C(F)F GSUNTOFGQYCPCU-UHFFFAOYSA-N 0.000 description 1
- LXOCLYFDFATRPI-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NN=C(C(F)(F)F)S1 LXOCLYFDFATRPI-UHFFFAOYSA-N 0.000 description 1
- LHTAADVHXJCCET-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-(trifluoromethyl)pyridine Chemical compound FC(F)=CCCS(=O)(=O)C1=CC=C(C(F)(F)F)C=N1 LHTAADVHXJCCET-UHFFFAOYSA-N 0.000 description 1
- HFHPVTURBVVYNZ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-[(4-methoxyphenyl)methyl]-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1CC1=NN=C(S(=O)(=O)CCC=C(F)F)O1 HFHPVTURBVVYNZ-UHFFFAOYSA-N 0.000 description 1
- PPGQAUPUTWEWMD-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-[(4-nitrophenyl)methyl]-1,3,4-oxadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=NN=C(S(=O)(=O)CCC=C(F)F)O1 PPGQAUPUTWEWMD-UHFFFAOYSA-N 0.000 description 1
- PAFAJCFRYKJNLV-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(S(=O)(=O)CCC=C(F)F)S1 PAFAJCFRYKJNLV-UHFFFAOYSA-N 0.000 description 1
- AFQIZGFQEARWIF-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-methyl-1-propan-2-ylimidazole Chemical compound CC(C)N1C(C)=CN=C1S(=O)(=O)CCC=C(F)F AFQIZGFQEARWIF-UHFFFAOYSA-N 0.000 description 1
- WZUQFIFWQBXKFQ-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-methyl-1h-imidazole Chemical compound CC1=CNC(S(=O)(=O)CCC=C(F)F)=N1 WZUQFIFWQBXKFQ-UHFFFAOYSA-N 0.000 description 1
- NCJSREUJYCJAON-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-methylfuran Chemical compound CC1=CC=C(S(=O)(=O)CCC=C(F)F)O1 NCJSREUJYCJAON-UHFFFAOYSA-N 0.000 description 1
- RHWBMGMUODPCJE-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-phenyl-1,3,4-thiadiazole Chemical compound S1C(S(=O)(=O)CCC=C(F)F)=NN=C1C1=CC=CC=C1 RHWBMGMUODPCJE-UHFFFAOYSA-N 0.000 description 1
- IFRVMROXUAUNDB-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)-5-phenyl-1,3-oxazole Chemical compound O1C(S(=O)(=O)CCC=C(F)F)=NC=C1C1=CC=CC=C1 IFRVMROXUAUNDB-UHFFFAOYSA-N 0.000 description 1
- PWVRUFDAKPLDFI-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)pyridine Chemical compound FC(F)=CCCS(=O)(=O)C1=CC=CC=N1 PWVRUFDAKPLDFI-UHFFFAOYSA-N 0.000 description 1
- MIVBPEJLMPRFRY-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfonyl)thiophene Chemical compound FC(F)=CCCS(=O)(=O)C1=CC=CS1 MIVBPEJLMPRFRY-UHFFFAOYSA-N 0.000 description 1
- JFONGQRKKZPXLX-UHFFFAOYSA-N 2-(4-nitrophenyl)acetohydrazide Chemical compound NNC(=O)CC1=CC=C([N+]([O-])=O)C=C1 JFONGQRKKZPXLX-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- RUYNUXHHUVUINQ-UHFFFAOYSA-N 2-Methyl-3-furanthiol Chemical compound CC=1OC=CC=1S RUYNUXHHUVUINQ-UHFFFAOYSA-N 0.000 description 1
- NXGKPRKPUCSEIL-UHFFFAOYSA-N 2-acetamido-4-methyl-1,3-thiazole-5-sulfonyl chloride Chemical compound CC(=O)NC1=NC(C)=C(S(Cl)(=O)=O)S1 NXGKPRKPUCSEIL-UHFFFAOYSA-N 0.000 description 1
- QXTRPGAMVIONMK-UHFFFAOYSA-N 2-amino-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(N)S1 QXTRPGAMVIONMK-UHFFFAOYSA-N 0.000 description 1
- RVRSDRDFORBZDM-UHFFFAOYSA-N 2-benzyl-5-(4,4-difluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound S1C(SCCC=C(F)F)=NN=C1CC1=CC=CC=C1 RVRSDRDFORBZDM-UHFFFAOYSA-N 0.000 description 1
- CORSRKUJUSRRFX-UHFFFAOYSA-N 2-bromo-5-(4,4-difluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound FC(F)=CCCSC1=NN=C(Br)S1 CORSRKUJUSRRFX-UHFFFAOYSA-N 0.000 description 1
- ANIJFZVZXZQFDH-UHFFFAOYSA-N 2-bromo-5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=CN=C(Br)S1 ANIJFZVZXZQFDH-UHFFFAOYSA-N 0.000 description 1
- KJWNZEAIJMQAAP-UHFFFAOYSA-N 2-butyl-5-(4,4-difluorobut-3-enylsulfanyl)-1,3,4-oxadiazole Chemical compound CCCCC1=NN=C(SCCC=C(F)F)O1 KJWNZEAIJMQAAP-UHFFFAOYSA-N 0.000 description 1
- ZKSNGTOYIDASGP-UHFFFAOYSA-N 2-butyl-5-(4,4-difluorobut-3-enylsulfonyl)-1,3,4-oxadiazole Chemical compound CCCCC1=NN=C(S(=O)(=O)CCC=C(F)F)O1 ZKSNGTOYIDASGP-UHFFFAOYSA-N 0.000 description 1
- HQLNXNULSFAGPR-UHFFFAOYSA-N 2-chloro-4-(4,4-difluorobut-3-enylsulfanyl)pyridine Chemical compound FC(F)=CCCSC1=CC=NC(Cl)=C1 HQLNXNULSFAGPR-UHFFFAOYSA-N 0.000 description 1
- BTHKGNOSBGTLFD-UHFFFAOYSA-N 2-chloro-5-(4,4-difluorobut-3-enylsulfinyl)-1,3-thiazole Chemical compound FC(F)=CCCS(=O)C1=CN=C(Cl)S1 BTHKGNOSBGTLFD-UHFFFAOYSA-N 0.000 description 1
- NZIAYCGKHLWXQD-UHFFFAOYSA-N 2-chloro-5-(4,4-difluorobut-3-enylsulfonyl)-1,3-thiazole Chemical compound FC(F)=CCCS(=O)(=O)C1=CN=C(Cl)S1 NZIAYCGKHLWXQD-UHFFFAOYSA-N 0.000 description 1
- WFPIZBVKJGHELN-UHFFFAOYSA-N 2-chloro-6-(4,4-difluorobut-3-enylsulfanyl)pyrazine Chemical compound FC(F)=CCCSC1=CN=CC(Cl)=N1 WFPIZBVKJGHELN-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- PCWJAJJRWTVGKK-UHFFFAOYSA-N 2-cyclopropyl-1,3,4-thiadiazole Chemical compound C1CC1C1=NN=CS1 PCWJAJJRWTVGKK-UHFFFAOYSA-N 0.000 description 1
- ZOTJPKFTRQEUGX-UHFFFAOYSA-N 2-cyclopropyl-5-(4,4-difluorobut-3-enylsulfonyl)-1,3,4-thiadiazole Chemical compound S1C(S(=O)(=O)CCC=C(F)F)=NN=C1C1CC1 ZOTJPKFTRQEUGX-UHFFFAOYSA-N 0.000 description 1
- GVPVKNZZLIICEQ-UHFFFAOYSA-N 2-cyclopropylacetohydrazide Chemical compound NNC(=O)CC1CC1 GVPVKNZZLIICEQ-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- QKPVEISEHYYHRH-UHFFFAOYSA-N 2-methoxyacetonitrile Chemical compound COCC#N QKPVEISEHYYHRH-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- PLNNJQXIITYYTN-UHFFFAOYSA-N 2-methylpropanehydrazide Chemical compound CC(C)C(=O)NN PLNNJQXIITYYTN-UHFFFAOYSA-N 0.000 description 1
- YNKRJGZPPAUPLQ-UHFFFAOYSA-N 2-methylsulfonyl-1h-imidazole Chemical compound CS(=O)(=O)C1=NC=CN1 YNKRJGZPPAUPLQ-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- WYKHFQKONWMWQM-UHFFFAOYSA-N 2-sulfanylidene-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1S WYKHFQKONWMWQM-UHFFFAOYSA-N 0.000 description 1
- VEYZDINYYFEYCZ-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3,4-thiadiazole-5-carboxamide Chemical compound NC(=O)C1=NN=C(S)S1 VEYZDINYYFEYCZ-UHFFFAOYSA-N 0.000 description 1
- MENOLVSGCYSOAF-UHFFFAOYSA-N 2-tert-butyl-5-(4,4-difluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound CC(C)(C)C1=NN=C(SCCC=C(F)F)S1 MENOLVSGCYSOAF-UHFFFAOYSA-N 0.000 description 1
- LYGLYFUBLZCHCT-UHFFFAOYSA-N 2h-1,2,4-oxadiazole-5-thione Chemical class SC1=NC=NO1 LYGLYFUBLZCHCT-UHFFFAOYSA-N 0.000 description 1
- CZLFQZFHKUHTMS-UHFFFAOYSA-N 2h-1,2,4-thiadiazole-5-thione Chemical compound SC1=NC=NS1 CZLFQZFHKUHTMS-UHFFFAOYSA-N 0.000 description 1
- GPGXJKMZTOSTHX-UHFFFAOYSA-N 3,5-bis(4,4-difluorobut-3-enylsulfanyl)-1,2,4-thiadiazole Chemical compound FC(F)=CCCSC1=NSC(SCCC=C(F)F)=N1 GPGXJKMZTOSTHX-UHFFFAOYSA-N 0.000 description 1
- PGGDFGKHBZHIBJ-UHFFFAOYSA-N 3,5-bis(4,4-difluorobut-3-enylsulfanyl)-1,2-thiazole-4-carbonitrile Chemical compound FC(F)=CCCSC1=NSC(SCCC=C(F)F)=C1C#N PGGDFGKHBZHIBJ-UHFFFAOYSA-N 0.000 description 1
- FPCJRRKJUDUYGD-UHFFFAOYSA-N 3,5-bis(4,4-difluorobut-3-enylsulfonyl)-1,2-thiazole-4-carbonitrile Chemical compound FC(F)=CCCS(=O)(=O)C1=NSC(S(=O)(=O)CCC=C(F)F)=C1C#N FPCJRRKJUDUYGD-UHFFFAOYSA-N 0.000 description 1
- RUNARDFVMLWILC-UHFFFAOYSA-N 3,5-dichloro-1,2-thiazole-4-carbonitrile Chemical compound ClC1=NSC(Cl)=C1C#N RUNARDFVMLWILC-UHFFFAOYSA-N 0.000 description 1
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 1
- VJGLWBPWRLDQQW-UHFFFAOYSA-N 3-(3-nitrophenyl)-2h-1,2,4-thiadiazole-5-thione Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(S)SN=2)=C1 VJGLWBPWRLDQQW-UHFFFAOYSA-N 0.000 description 1
- TTYCKASBVLGCEA-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfanyl)-2-methylfuran Chemical compound CC=1OC=CC=1SCCC=C(F)F TTYCKASBVLGCEA-UHFFFAOYSA-N 0.000 description 1
- DZZLASRAWDGRDZ-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfanyl)-5-methoxy-1,2,4-thiadiazole Chemical compound COC1=NC(SCCC=C(F)F)=NS1 DZZLASRAWDGRDZ-UHFFFAOYSA-N 0.000 description 1
- OQXHHQWWLUBOMD-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfanyl)-6-methoxypyridazine Chemical compound COC1=CC=C(SCCC=C(F)F)N=N1 OQXHHQWWLUBOMD-UHFFFAOYSA-N 0.000 description 1
- AHHJANFCBOYLME-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfanyl)-6-methylpyridazine Chemical compound CC1=CC=C(SCCC=C(F)F)N=N1 AHHJANFCBOYLME-UHFFFAOYSA-N 0.000 description 1
- YBFNPFCEUQDWCY-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfanyl)-6-phenylpyridazine Chemical compound N1=NC(SCCC=C(F)F)=CC=C1C1=CC=CC=C1 YBFNPFCEUQDWCY-UHFFFAOYSA-N 0.000 description 1
- XOIJXUQHWZOQAU-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfanyl)butan-2-one Chemical compound CC(=O)C(C)SCCC=C(F)F XOIJXUQHWZOQAU-UHFFFAOYSA-N 0.000 description 1
- DOWYCTVBXAFVCH-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfinyl)-2-methylfuran Chemical compound CC=1OC=CC=1S(=O)CCC=C(F)F DOWYCTVBXAFVCH-UHFFFAOYSA-N 0.000 description 1
- WBLZOBOZVVMHHH-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfonyl)-2-methylfuran Chemical compound CC=1OC=CC=1S(=O)(=O)CCC=C(F)F WBLZOBOZVVMHHH-UHFFFAOYSA-N 0.000 description 1
- NDAHACLTRWDPDH-UHFFFAOYSA-N 3-(4,4-difluorobut-3-enylsulfonyl)-6-phenylpyridazine Chemical compound N1=NC(S(=O)(=O)CCC=C(F)F)=CC=C1C1=CC=CC=C1 NDAHACLTRWDPDH-UHFFFAOYSA-N 0.000 description 1
- YONOPDGTJGMPDI-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyl-1,2,4-thiadiazole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=NSC=N1 YONOPDGTJGMPDI-UHFFFAOYSA-N 0.000 description 1
- FUVCCEJWTUFVMF-UHFFFAOYSA-N 3-(5-chlorofuran-2-yl)-5-(4,4-difluorobut-3-enylsulfanyl)-1,2-oxazole Chemical compound O1C(SCCC=C(F)F)=CC(C=2OC(Cl)=CC=2)=N1 FUVCCEJWTUFVMF-UHFFFAOYSA-N 0.000 description 1
- XBJJWYUSXDGTLA-UHFFFAOYSA-N 3-(5-chlorofuran-2-yl)-5-(4,4-difluorobut-3-enylsulfonyl)-1,2-oxazole Chemical compound O1C(S(=O)(=O)CCC=C(F)F)=CC(C=2OC(Cl)=CC=2)=N1 XBJJWYUSXDGTLA-UHFFFAOYSA-N 0.000 description 1
- IISUXACIIMWRDF-UHFFFAOYSA-N 3-(butoxymethyl)-5-(4,4-difluorobut-3-enylsulfanyl)-1,2,4-thiadiazole Chemical compound CCCCOCC1=NSC(SCCC=C(F)F)=N1 IISUXACIIMWRDF-UHFFFAOYSA-N 0.000 description 1
- OMAQJNZLYPYTSC-UHFFFAOYSA-N 3-(chloromethyl)-5-(4,4-difluorobut-3-enylsulfanyl)-1,2,4-thiadiazole Chemical compound FC(F)=CCCSC1=NC(CCl)=NS1 OMAQJNZLYPYTSC-UHFFFAOYSA-N 0.000 description 1
- VPMPSDXBMHISFD-UHFFFAOYSA-N 3-(methoxymethyl)-2h-1,2,4-oxadiazole-5-thione Chemical compound COCC1=NOC(S)=N1 VPMPSDXBMHISFD-UHFFFAOYSA-N 0.000 description 1
- YXVRCDCHBJJZKI-UHFFFAOYSA-N 3-(methoxymethyl)-5-(4-methylphenyl)sulfonyl-1,2,4-thiadiazole Chemical compound COCC1=NSC(S(=O)(=O)C=2C=CC(C)=CC=2)=N1 YXVRCDCHBJJZKI-UHFFFAOYSA-N 0.000 description 1
- ONZQYZKCUHFORE-UHFFFAOYSA-N 3-bromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)CBr ONZQYZKCUHFORE-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- ABQYSTWSLKDOGY-UHFFFAOYSA-N 3-chloro-1h-pyrazine-2-thione Chemical compound SC1=NC=CN=C1Cl ABQYSTWSLKDOGY-UHFFFAOYSA-N 0.000 description 1
- YZDRPYATZZGECN-UHFFFAOYSA-N 3-chloro-6-(4,4-difluorobut-3-enylsulfanyl)pyridazine Chemical compound FC(F)=CCCSC1=CC=C(Cl)N=N1 YZDRPYATZZGECN-UHFFFAOYSA-N 0.000 description 1
- XBJLKXOOHLLTPG-UHFFFAOYSA-N 3-chloro-6-methoxypyridazine Chemical compound COC1=CC=C(Cl)N=N1 XBJLKXOOHLLTPG-UHFFFAOYSA-N 0.000 description 1
- PRORLQAJNJMGAR-UHFFFAOYSA-N 3-chloro-6-methylpyridazine Chemical compound CC1=CC=C(Cl)N=N1 PRORLQAJNJMGAR-UHFFFAOYSA-N 0.000 description 1
- BUBRFWDEAVIFMV-UHFFFAOYSA-N 3-chloro-6-phenylpyridazine Chemical compound N1=NC(Cl)=CC=C1C1=CC=CC=C1 BUBRFWDEAVIFMV-UHFFFAOYSA-N 0.000 description 1
- FGIDGUKHKIBZKM-UHFFFAOYSA-N 3-chloropyrazine Chemical compound ClC1=CN=C=C[N]1 FGIDGUKHKIBZKM-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 1
- RUBRCWOFANAOTP-UHFFFAOYSA-N 3h-1,3,4-oxadiazole-2-thione Chemical class S=C1NN=CO1 RUBRCWOFANAOTP-UHFFFAOYSA-N 0.000 description 1
- HHSVUXGWUCYGPR-UHFFFAOYSA-N 4-(4,4-difluorobut-3-enylsulfanyl)-2,3,5,6-tetrafluoropyridine Chemical compound FC(F)=CCCSC1=C(F)C(F)=NC(F)=C1F HHSVUXGWUCYGPR-UHFFFAOYSA-N 0.000 description 1
- FZMKSWDSUYQZET-UHFFFAOYSA-N 4-(4,4-difluorobut-3-enylsulfanyl)pyridine Chemical compound FC(F)=CCCSC1=CC=NC=C1 FZMKSWDSUYQZET-UHFFFAOYSA-N 0.000 description 1
- IGQKKMDDNDKCEC-UHFFFAOYSA-N 4-(4,4-difluorobut-3-enylsulfinyl)-2,3,5,6-tetrafluoropyridine Chemical compound FC(F)=CCCS(=O)C1=C(F)C(F)=NC(F)=C1F IGQKKMDDNDKCEC-UHFFFAOYSA-N 0.000 description 1
- FXBPHXYPBSVCCW-UHFFFAOYSA-N 4-(4,4-difluorobut-3-enylsulfonyl)pyridine Chemical compound FC(F)=CCCS(=O)(=O)C1=CC=NC=C1 FXBPHXYPBSVCCW-UHFFFAOYSA-N 0.000 description 1
- YVJNSJXQUKIQGE-UHFFFAOYSA-N 4-(trifluoromethyl)-3h-1,3-thiazole-2-thione Chemical compound FC(F)(F)C1=CSC(S)=N1 YVJNSJXQUKIQGE-UHFFFAOYSA-N 0.000 description 1
- BLBDTBCGPHPIJK-UHFFFAOYSA-N 4-Amino-2-chloropyridine Chemical compound NC1=CC=NC(Cl)=C1 BLBDTBCGPHPIJK-UHFFFAOYSA-N 0.000 description 1
- LUVKAZYNIFYEJW-UHFFFAOYSA-N 4-[[5-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazol-2-yl]oxy]benzonitrile Chemical compound S1C(SCCC=C(F)F)=CN=C1OC1=CC=C(C#N)C=C1 LUVKAZYNIFYEJW-UHFFFAOYSA-N 0.000 description 1
- IOOKZIHANKCPNE-UHFFFAOYSA-N 4-bromo-5-(4,4-difluorobut-3-enylsulfanyl)-1-methylpyrazole Chemical compound CN1N=CC(Br)=C1SCCC=C(F)F IOOKZIHANKCPNE-UHFFFAOYSA-N 0.000 description 1
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 1
- LLHMNSNECXJBQY-UHFFFAOYSA-N 4-chloro-2,3,5,6-tetrafluoropyridine Chemical compound FC1=NC(F)=C(F)C(Cl)=C1F LLHMNSNECXJBQY-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- APJVCBWXRMBAET-UHFFFAOYSA-N 4-methyl-1,3-thiazol-2-amine;sulfuryl difluoride Chemical compound FS(F)(=O)=O.CC1=CSC(N)=N1 APJVCBWXRMBAET-UHFFFAOYSA-N 0.000 description 1
- PIDBMNPCPAEPCX-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;thiourea Chemical compound NC(S)=[NH2+].CC1=CC=C(S([O-])(=O)=O)C=C1 PIDBMNPCPAEPCX-UHFFFAOYSA-N 0.000 description 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- DVGHKLUHJSFLIT-UHFFFAOYSA-N 5-(2-methoxyphenyl)-3h-1,3,4-oxadiazole-2-thione Chemical compound COC1=CC=CC=C1C1=NNC(=S)O1 DVGHKLUHJSFLIT-UHFFFAOYSA-N 0.000 description 1
- HNFIJWNVPWXSOL-UHFFFAOYSA-N 5-(2-methylphenyl)-3h-1,3,4-oxadiazole-2-thione Chemical compound CC1=CC=CC=C1C1=NNC(=S)O1 HNFIJWNVPWXSOL-UHFFFAOYSA-N 0.000 description 1
- GOYONEZXQVVSMH-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3,4-oxadiazole-2-carboxamide Chemical compound NC(=O)C1=NN=C(SCCC=C(F)F)O1 GOYONEZXQVVSMH-UHFFFAOYSA-N 0.000 description 1
- ZTUPWNZQKAFUHC-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(SCCC=C(F)F)S1 ZTUPWNZQKAFUHC-UHFFFAOYSA-N 0.000 description 1
- IUQJEJHYZATNFJ-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3,4-thiadiazole-2-carboxamide Chemical compound NC(=O)C1=NN=C(SCCC=C(F)F)S1 IUQJEJHYZATNFJ-UHFFFAOYSA-N 0.000 description 1
- BEGAVTJCTJTQHX-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3-dimethyl-4-nitropyrazole Chemical compound CC1=NN(C)C(SCCC=C(F)F)=C1[N+]([O-])=O BEGAVTJCTJTQHX-UHFFFAOYSA-N 0.000 description 1
- JSSASFBFOIIUAP-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3-dimethylpyrazole Chemical compound CC=1C=C(SCCC=C(F)F)N(C)N=1 JSSASFBFOIIUAP-UHFFFAOYSA-N 0.000 description 1
- MCNVVYCEEZWUMS-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3-dimethylpyrazole-4-carbonitrile Chemical compound CC1=NN(C)C(SCCC=C(F)F)=C1C#N MCNVVYCEEZWUMS-UHFFFAOYSA-N 0.000 description 1
- FQQOSCRJHHZMAG-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole-4-carbonitrile Chemical compound FC(F)=CCCSC=1SC=NC=1C#N FQQOSCRJHHZMAG-UHFFFAOYSA-N 0.000 description 1
- CVOCDLSCQAIMAU-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1N=CSC=1SCCC=C(F)F CVOCDLSCQAIMAU-UHFFFAOYSA-N 0.000 description 1
- ONVKUYWEUWEXSI-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=CC(C(O)=O)=C1SCCC=C(F)F ONVKUYWEUWEXSI-UHFFFAOYSA-N 0.000 description 1
- JAIKXKZKWSEDSF-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-1-methyltetrazole Chemical compound CN1N=NN=C1SCCC=C(F)F JAIKXKZKWSEDSF-UHFFFAOYSA-N 0.000 description 1
- HPTILSRFLYZBEQ-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-(3-nitrophenyl)-1,2,4-thiadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(SCCC=C(F)F)SN=2)=C1 HPTILSRFLYZBEQ-UHFFFAOYSA-N 0.000 description 1
- LPOVQPUAOBWRMJ-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-(methoxymethyl)-1,2,4-thiadiazole Chemical compound COCC1=NSC(SCCC=C(F)F)=N1 LPOVQPUAOBWRMJ-UHFFFAOYSA-N 0.000 description 1
- VTCJCKNBYWZSPB-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-ethyl-1,2,4-thiadiazole Chemical compound CCC1=NSC(SCCC=C(F)F)=N1 VTCJCKNBYWZSPB-UHFFFAOYSA-N 0.000 description 1
- DCVWTYHNZSKSNO-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-methoxy-1,2,4-thiadiazole Chemical compound COC1=NSC(SCCC=C(F)F)=N1 DCVWTYHNZSKSNO-UHFFFAOYSA-N 0.000 description 1
- PJTGIRLZCHYGQT-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(SCCC=C(F)F)=N1 PJTGIRLZCHYGQT-UHFFFAOYSA-N 0.000 description 1
- SRSVRQQFXHZBBH-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(SCCC=C(F)F)=C1C(N)=O SRSVRQQFXHZBBH-UHFFFAOYSA-N 0.000 description 1
- PYEXTWHACNCNSN-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(SCCC=C(F)F)=C1C(O)=O PYEXTWHACNCNSN-UHFFFAOYSA-N 0.000 description 1
- VXZGWWTWWUUXKF-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-methylsulfanyl-1,2,4-thiadiazole Chemical compound CSC1=NSC(SCCC=C(F)F)=N1 VXZGWWTWWUUXKF-UHFFFAOYSA-N 0.000 description 1
- ZYNCKGBWHJKMCU-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-phenyl-1,2,4-oxadiazole Chemical compound O1C(SCCC=C(F)F)=NC(C=2C=CC=CC=2)=N1 ZYNCKGBWHJKMCU-UHFFFAOYSA-N 0.000 description 1
- MSKGCPXRHWYHLF-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-phenyl-1,2,4-thiadiazole Chemical compound S1C(SCCC=C(F)F)=NC(C=2C=CC=CC=2)=N1 MSKGCPXRHWYHLF-UHFFFAOYSA-N 0.000 description 1
- UXEIWOVFNAEYBD-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-phenyl-1,2-oxazole Chemical compound O1C(SCCC=C(F)F)=CC(C=2C=CC=CC=2)=N1 UXEIWOVFNAEYBD-UHFFFAOYSA-N 0.000 description 1
- MBMRJCFQGKCPLR-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-3-thiophen-2-yl-1,2-oxazole Chemical compound O1C(SCCC=C(F)F)=CC(C=2SC=CC=2)=N1 MBMRJCFQGKCPLR-UHFFFAOYSA-N 0.000 description 1
- NVVVUNGHYOZDIE-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-4-iodo-1,3-dimethylpyrazole Chemical compound CC1=NN(C)C(SCCC=C(F)F)=C1I NVVVUNGHYOZDIE-UHFFFAOYSA-N 0.000 description 1
- QYTQQGGDJIZVKB-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)-n-methyl-1,3,4-thiadiazol-2-amine Chemical compound CNC1=NN=C(SCCC=C(F)F)S1 QYTQQGGDJIZVKB-UHFFFAOYSA-N 0.000 description 1
- VPCQBODPDGKRRK-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)thiophene-2-carbaldehyde Chemical compound FC(F)=CCCSC1=CC=C(C=O)S1 VPCQBODPDGKRRK-UHFFFAOYSA-N 0.000 description 1
- FGRYPWWWBDVQNE-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfanyl)thiophene-2-carbonitrile Chemical compound FC(F)=CCCSC1=CC=C(C#N)S1 FGRYPWWWBDVQNE-UHFFFAOYSA-N 0.000 description 1
- NFWIPIWTNPAYFN-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfinyl)-1,3-thiazole Chemical compound FC(F)=CCCS(=O)C1=CN=CS1 NFWIPIWTNPAYFN-UHFFFAOYSA-N 0.000 description 1
- LXYXPQAHZCDEIS-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfinyl)-3-phenyl-1,2-oxazole Chemical compound O1C(S(=O)CCC=C(F)F)=CC(C=2C=CC=CC=2)=N1 LXYXPQAHZCDEIS-UHFFFAOYSA-N 0.000 description 1
- RXFCXDVYJLJFSB-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfonyl)-1,2-thiazole-4-carbonitrile Chemical compound FC(F)=CCCS(=O)(=O)C=1SN=CC=1C#N RXFCXDVYJLJFSB-UHFFFAOYSA-N 0.000 description 1
- RMVDYAYKVLCBLF-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfonyl)-1,3-dimethyl-4-nitropyrazole Chemical compound CC1=NN(C)C(S(=O)(=O)CCC=C(F)F)=C1[N+]([O-])=O RMVDYAYKVLCBLF-UHFFFAOYSA-N 0.000 description 1
- XXSHMTUQWNVBIW-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfonyl)-1,3-dimethylpyrazole-4-carbonitrile Chemical compound CC1=NN(C)C(S(=O)(=O)CCC=C(F)F)=C1C#N XXSHMTUQWNVBIW-UHFFFAOYSA-N 0.000 description 1
- JIZXUWZYVULXSN-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfonyl)-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=CC(C(O)=O)=C1S(=O)(=O)CCC=C(F)F JIZXUWZYVULXSN-UHFFFAOYSA-N 0.000 description 1
- SAUMAKZXOVZODB-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfonyl)-3-phenyl-1,2-oxazole Chemical compound O1C(S(=O)(=O)CCC=C(F)F)=CC(C=2C=CC=CC=2)=N1 SAUMAKZXOVZODB-UHFFFAOYSA-N 0.000 description 1
- PSUROBSKVMHYHH-UHFFFAOYSA-N 5-(4,4-difluorobut-3-enylsulfonyl)-3-thiophen-2-yl-1,2-oxazole Chemical compound O1C(S(=O)(=O)CCC=C(F)F)=CC(C=2SC=CC=2)=N1 PSUROBSKVMHYHH-UHFFFAOYSA-N 0.000 description 1
- LNVKBMUPSYJYPF-UHFFFAOYSA-N 5-(4-methoxyphenyl)-3h-1,3,4-thiadiazole-2-thione Chemical compound C1=CC(OC)=CC=C1C1=NNC(=S)S1 LNVKBMUPSYJYPF-UHFFFAOYSA-N 0.000 description 1
- YEAUYAAOEJVUTK-UHFFFAOYSA-N 5-(4-methylphenyl)sulfonyl-1,2,4-thiadiazole Chemical class C1=CC(C)=CC=C1S(=O)(=O)C1=NC=NS1 YEAUYAAOEJVUTK-UHFFFAOYSA-N 0.000 description 1
- ABSVCMBOXHMZPV-UHFFFAOYSA-N 5-(4-nitrophenyl)-3h-1,3,4-oxadiazole-2-thione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NN=C(S)O1 ABSVCMBOXHMZPV-UHFFFAOYSA-N 0.000 description 1
- JMRAYTPNXKJWAX-UHFFFAOYSA-N 5-(methylamino)-3H-1,3,4-thiadiazole-2-thione Chemical compound CNC1=NN=C(S)S1 JMRAYTPNXKJWAX-UHFFFAOYSA-N 0.000 description 1
- YFSCXLSUZZXNHW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyridine-2-thione Chemical compound FC(F)(F)C1=CC=C(S)N=C1 YFSCXLSUZZXNHW-UHFFFAOYSA-N 0.000 description 1
- HDNGCYKGWGMLMD-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-3h-1,3,4-thiadiazole-2-thione Chemical compound FC1=CC=CC(F)=C1CC1=NNC(=S)S1 HDNGCYKGWGMLMD-UHFFFAOYSA-N 0.000 description 1
- ICAZBRUDKZCQHF-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-3h-1,3,4-oxadiazole-2-thione Chemical compound C1=CC(OC)=CC=C1CC1=NNC(=S)O1 ICAZBRUDKZCQHF-UHFFFAOYSA-N 0.000 description 1
- SMDJZLNECVKAAL-UHFFFAOYSA-N 5-[(4-nitrophenyl)methyl]-3h-1,3,4-thiadiazole-2-thione Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=NNC(=S)S1 SMDJZLNECVKAAL-UHFFFAOYSA-N 0.000 description 1
- ARGIBMBTIISQNH-UHFFFAOYSA-N 5-benzyl-3h-1,3,4-oxadiazole-2-thione Chemical compound O1C(=S)NN=C1CC1=CC=CC=C1 ARGIBMBTIISQNH-UHFFFAOYSA-N 0.000 description 1
- HJHBEIHCZKXOJI-UHFFFAOYSA-N 5-bromo-2-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole Chemical compound FC(F)=CCCSC1=NC=C(Br)S1 HJHBEIHCZKXOJI-UHFFFAOYSA-N 0.000 description 1
- TVTPJIQZRSJPLP-UHFFFAOYSA-N 5-bromo-2-(4,4-difluorobut-3-enylsulfanyl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1N=C(SCCC=C(F)F)SC=1Br TVTPJIQZRSJPLP-UHFFFAOYSA-N 0.000 description 1
- SFLOIOBTLLNAJH-UHFFFAOYSA-N 5-bromo-4-ethyl-1,3-thiazol-2-amine Chemical compound CCC=1N=C(N)SC=1Br SFLOIOBTLLNAJH-UHFFFAOYSA-N 0.000 description 1
- YCSKCFNAZMHYAL-UHFFFAOYSA-N 5-butyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CCCCC1=NNC(=S)S1 YCSKCFNAZMHYAL-UHFFFAOYSA-N 0.000 description 1
- WBMBDRIOUHCVAS-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-4-nitropyrazole Chemical compound CC1=NN(C)C(Cl)=C1[N+]([O-])=O WBMBDRIOUHCVAS-UHFFFAOYSA-N 0.000 description 1
- SWQWTDAWUSBMGA-UHFFFAOYSA-N 5-chloro-1,3-thiazol-2-amine Chemical compound NC1=NC=C(Cl)S1 SWQWTDAWUSBMGA-UHFFFAOYSA-N 0.000 description 1
- UJDRRPVBUDFHDG-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfanyl)-1,3-oxazole Chemical compound FC(F)=CCCSC1=NC=C(Cl)O1 UJDRRPVBUDFHDG-UHFFFAOYSA-N 0.000 description 1
- WTXBRGUYKBYMPY-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-oxazole Chemical compound CC=1N=C(SCCC=C(F)F)OC=1Cl WTXBRGUYKBYMPY-UHFFFAOYSA-N 0.000 description 1
- OAFRDTRNDVWHSW-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfanyl)-4-methyl-1,3-thiazole Chemical compound CC=1N=C(SCCC=C(F)F)SC=1Cl OAFRDTRNDVWHSW-UHFFFAOYSA-N 0.000 description 1
- WXTSCVPDYNYOCQ-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfanyl)pyridine Chemical compound FC(F)=CCCSC1=CC=C(Cl)C=N1 WXTSCVPDYNYOCQ-UHFFFAOYSA-N 0.000 description 1
- APTHUWZSCHTYMS-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfinyl)-1,3-thiazole Chemical compound FC(F)=CCCS(=O)C1=NC=C(Cl)S1 APTHUWZSCHTYMS-UHFFFAOYSA-N 0.000 description 1
- DYOUGXXKOKQDFJ-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfonyl)-1,3-oxazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NC=C(Cl)O1 DYOUGXXKOKQDFJ-UHFFFAOYSA-N 0.000 description 1
- TXJZMTKOQLDXMU-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfonyl)-1,3-thiazole Chemical compound FC(F)=CCCS(=O)(=O)C1=NC=C(Cl)S1 TXJZMTKOQLDXMU-UHFFFAOYSA-N 0.000 description 1
- UMPHWIZIXFHXCZ-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfonyl)-4-methyl-1,3-oxazole Chemical compound CC=1N=C(S(=O)(=O)CCC=C(F)F)OC=1Cl UMPHWIZIXFHXCZ-UHFFFAOYSA-N 0.000 description 1
- NSWJKICAUHFJOK-UHFFFAOYSA-N 5-chloro-2-(4,4-difluorobut-3-enylsulfonyl)-4-methyl-1,3-thiazole Chemical compound CC=1N=C(S(=O)(=O)CCC=C(F)F)SC=1Cl NSWJKICAUHFJOK-UHFFFAOYSA-N 0.000 description 1
- RYKPJHUVEKGEJQ-UHFFFAOYSA-N 5-chloro-3-(4,4-difluorobut-3-enylsulfanyl)-1,2,4-thiadiazole Chemical compound FC(F)=CCCSC1=NSC(Cl)=N1 RYKPJHUVEKGEJQ-UHFFFAOYSA-N 0.000 description 1
- ATFXELIUGPSCOB-UHFFFAOYSA-N 5-chloro-3-(5-chlorofuran-2-yl)-1,2-oxazole Chemical compound O1C(Cl)=CC=C1C1=NOC(Cl)=C1 ATFXELIUGPSCOB-UHFFFAOYSA-N 0.000 description 1
- FFFMIFUBJZBTCG-UHFFFAOYSA-N 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole Chemical compound ClCC1=NSC(Cl)=N1 FFFMIFUBJZBTCG-UHFFFAOYSA-N 0.000 description 1
- MCZJFFUPCJJZSD-UHFFFAOYSA-N 5-chloro-3-(trifluoromethyl)-1,2,4-thiadiazole Chemical compound FC(F)(F)C1=NSC(Cl)=N1 MCZJFFUPCJJZSD-UHFFFAOYSA-N 0.000 description 1
- XSOLUMIPOFCILY-UHFFFAOYSA-N 5-chloro-3-ethyl-4-methyl-1,2-oxazole Chemical compound CCC1=NOC(Cl)=C1C XSOLUMIPOFCILY-UHFFFAOYSA-N 0.000 description 1
- GYGNJEASCVSRLC-UHFFFAOYSA-N 5-chloro-3-methoxy-1,2,4-thiadiazole Chemical compound COC1=NSC(Cl)=N1 GYGNJEASCVSRLC-UHFFFAOYSA-N 0.000 description 1
- KWVZAEKGUQQYMK-UHFFFAOYSA-N 5-chloro-3-phenyl-1,2-oxazole Chemical compound O1C(Cl)=CC(C=2C=CC=CC=2)=N1 KWVZAEKGUQQYMK-UHFFFAOYSA-N 0.000 description 1
- YRNZHGGLFXSEGE-UHFFFAOYSA-N 5-chloro-3-pyrazin-2-yl-1,2,4-thiadiazole Chemical compound S1C(Cl)=NC(C=2N=CC=NC=2)=N1 YRNZHGGLFXSEGE-UHFFFAOYSA-N 0.000 description 1
- CSEOGLHLODHHRZ-UHFFFAOYSA-N 5-chloro-3-thiophen-2-yl-1,2-oxazole Chemical compound O1C(Cl)=CC(C=2SC=CC=2)=N1 CSEOGLHLODHHRZ-UHFFFAOYSA-N 0.000 description 1
- WUTUCTHNAXSTGJ-UHFFFAOYSA-N 5-chloro-4-methyl-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1Cl WUTUCTHNAXSTGJ-UHFFFAOYSA-N 0.000 description 1
- UFSCJPPXRHCNLK-UHFFFAOYSA-N 5-ethyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CCC1=NN=C(S)S1 UFSCJPPXRHCNLK-UHFFFAOYSA-N 0.000 description 1
- GUABFMPMKJGSBQ-UHFFFAOYSA-N 5-methyl-1,3-thiazol-2-amine Chemical compound CC1=CN=C(N)S1 GUABFMPMKJGSBQ-UHFFFAOYSA-N 0.000 description 1
- BHQUBONFIYNJDA-UHFFFAOYSA-N 5-nitro-1h-pyridine-2-thione Chemical compound [O-][N+](=O)C1=CC=C(S)N=C1 BHQUBONFIYNJDA-UHFFFAOYSA-N 0.000 description 1
- MQEVJIWAXUSJNI-UHFFFAOYSA-N 5-nitro-3h-1,3-thiazole-2-thione Chemical compound [O-][N+](=O)C1=CN=C(S)S1 MQEVJIWAXUSJNI-UHFFFAOYSA-N 0.000 description 1
- DXTALFJKXBHPNL-UHFFFAOYSA-N 5-pentyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CCCCCC1=NN=C(S)S1 DXTALFJKXBHPNL-UHFFFAOYSA-N 0.000 description 1
- FOHWXVBZGSVUGO-UHFFFAOYSA-N 5-phenyl-3h-1,3,4-oxadiazole-2-thione Chemical compound O1C(S)=NN=C1C1=CC=CC=C1 FOHWXVBZGSVUGO-UHFFFAOYSA-N 0.000 description 1
- MWLSEYMWXVXBOW-UHFFFAOYSA-N 5-phenyl-3h-1,3-thiazole-2-thione Chemical compound S1C(S)=NC=C1C1=CC=CC=C1 MWLSEYMWXVXBOW-UHFFFAOYSA-N 0.000 description 1
- CJMUOXLDOLNLKB-UHFFFAOYSA-N 5-propan-2-yl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC(C)C1=NNC(=S)S1 CJMUOXLDOLNLKB-UHFFFAOYSA-N 0.000 description 1
- PYVUFGZVZNBZRY-UHFFFAOYSA-N 5-propyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CCCC1=NNC(=S)S1 PYVUFGZVZNBZRY-UHFFFAOYSA-N 0.000 description 1
- BSPHQWQMWIUIPM-UHFFFAOYSA-N 5-pyridin-4-yl-3h-1,3,4-thiadiazole-2-thione Chemical compound S1C(=S)NN=C1C1=CC=NC=C1 BSPHQWQMWIUIPM-UHFFFAOYSA-N 0.000 description 1
- OPZYRKWLFVOZTN-UHFFFAOYSA-N 5-thiophen-2-yl-3h-1,3,4-thiadiazole-2-thione Chemical compound S1C(=S)NN=C1C1=CC=CS1 OPZYRKWLFVOZTN-UHFFFAOYSA-N 0.000 description 1
- DRYOAYDKCAVTJF-UHFFFAOYSA-N 6-(4,4-difluorobut-3-enylsulfanyl)pyridine-3-carbonitrile Chemical compound FC(F)=CCCSC1=CC=C(C#N)C=N1 DRYOAYDKCAVTJF-UHFFFAOYSA-N 0.000 description 1
- YYLIVDUWJDABPG-UHFFFAOYSA-N 6-(4,4-difluorobut-3-enylsulfonyl)pyridine-3-carbonitrile Chemical compound FC(F)=CCCS(=O)(=O)C1=CC=C(C#N)C=N1 YYLIVDUWJDABPG-UHFFFAOYSA-N 0.000 description 1
- XPBWNZBVHZWVFZ-UHFFFAOYSA-N 6-chloro-1h-quinoxaline-2-thione Chemical compound N1C(=S)C=NC2=CC(Cl)=CC=C21 XPBWNZBVHZWVFZ-UHFFFAOYSA-N 0.000 description 1
- IBJINEACPHKZOF-UHFFFAOYSA-N 6-chloro-2-(4,4-difluorobut-3-enylsulfanyl)quinoxaline Chemical compound C1=C(Cl)C=CC2=NC(SCCC=C(F)F)=CN=C21 IBJINEACPHKZOF-UHFFFAOYSA-N 0.000 description 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- 101100109978 Arabidopsis thaliana ARP3 gene Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
- 125000006416 CBr Chemical group BrC* 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 101000941450 Lasioglossum laticeps Lasioglossin-1 Proteins 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 101100427547 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) ULS1 gene Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- SWEDAZLCYJDAGW-UHFFFAOYSA-N Thiophene-2-thiol Chemical compound SC1=CC=CS1 SWEDAZLCYJDAGW-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- SFUDTUHSDOLYKT-UHFFFAOYSA-N [5-(4,4-difluorobut-3-enylsulfanyl)thiophen-2-yl]methanol Chemical compound OCC1=CC=C(SCCC=C(F)F)S1 SFUDTUHSDOLYKT-UHFFFAOYSA-N 0.000 description 1
- WYGCUSHOHRVKKS-UHFFFAOYSA-N [5-amino-1-(2-methylphenyl)pyrazol-4-yl]-phenylmethanone Chemical compound CC1=CC=CC=C1N1C(N)=C(C(=O)C=2C=CC=CC=2)C=N1 WYGCUSHOHRVKKS-UHFFFAOYSA-N 0.000 description 1
- KWWFZQQWGBLRPL-UHFFFAOYSA-N [Na].FC1=NC(=C(C(=C1F)S)F)F Chemical compound [Na].FC1=NC(=C(C(=C1F)S)F)F KWWFZQQWGBLRPL-UHFFFAOYSA-N 0.000 description 1
- QVTMGLKIERGFFS-UHFFFAOYSA-N acetic acid;isocyanatoethane Chemical compound CC(O)=O.CCN=C=O QVTMGLKIERGFFS-UHFFFAOYSA-N 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 125000005134 alkynylsulfinyl group Chemical group 0.000 description 1
- 125000005139 alkynylsulfonyl group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000006380 bromofluorination reaction Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- AZSZCFSOHXEJQE-UHFFFAOYSA-N dibromodifluoromethane Chemical compound FC(F)(Br)Br AZSZCFSOHXEJQE-UHFFFAOYSA-N 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 101150117607 dis1 gene Proteins 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- HFWHUWPIIOSFTJ-UHFFFAOYSA-N ethyl 2-(4,4-difluorobut-3-enylsulfanyl)-1h-imidazole-5-carboxylate Chemical compound CCOC(=O)C1=CNC(SCCC=C(F)F)=N1 HFWHUWPIIOSFTJ-UHFFFAOYSA-N 0.000 description 1
- AMJGEDHUMDPVSV-UHFFFAOYSA-N ethyl 2-(4,4-difluorobut-3-enylsulfanyl)-3-methylimidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=C(SCCC=C(F)F)N1C AMJGEDHUMDPVSV-UHFFFAOYSA-N 0.000 description 1
- GCTMVTIQJRCILX-UHFFFAOYSA-N ethyl 2-(4,4-difluorobut-3-enylsulfinyl)-1-methylimidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN(C)C(S(=O)CCC=C(F)F)=N1 GCTMVTIQJRCILX-UHFFFAOYSA-N 0.000 description 1
- UTFVBBVZPGHFBF-UHFFFAOYSA-N ethyl 2-(4,4-difluorobut-3-enylsulfonyl)-1-methylimidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN(C)C(S(=O)(=O)CCC=C(F)F)=N1 UTFVBBVZPGHFBF-UHFFFAOYSA-N 0.000 description 1
- FQJBQMHVMSOABI-UHFFFAOYSA-N ethyl 2-(4,4-difluorobut-3-enylsulfonyl)-3-methylimidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=C(S(=O)(=O)CCC=C(F)F)N1C FQJBQMHVMSOABI-UHFFFAOYSA-N 0.000 description 1
- DOCCDOCIYYDLGJ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C=C1 DOCCDOCIYYDLGJ-UHFFFAOYSA-N 0.000 description 1
- MWTKTJSKHCDMOW-UHFFFAOYSA-N ethyl 2-amino-4-(trifluoromethyl)-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)C=1OC(N)=NC=1C(F)(F)F MWTKTJSKHCDMOW-UHFFFAOYSA-N 0.000 description 1
- TWGNDRMYYDZGFI-UHFFFAOYSA-N ethyl 2-amino-5-bromo-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C=1N=C(N)SC=1Br TWGNDRMYYDZGFI-UHFFFAOYSA-N 0.000 description 1
- WTGNEFWADGCDBI-UHFFFAOYSA-N ethyl 2-sulfanylidene-3h-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(=S)N1 WTGNEFWADGCDBI-UHFFFAOYSA-N 0.000 description 1
- ZVZQVIATHWHRFP-UHFFFAOYSA-N ethyl 5-(4,4-difluorobut-3-enylsulfanyl)-1-phenylpyrazole-4-carboxylate Chemical compound FC(F)=CCCSC1=C(C(=O)OCC)C=NN1C1=CC=CC=C1 ZVZQVIATHWHRFP-UHFFFAOYSA-N 0.000 description 1
- OBWMABLVPSCXAS-UHFFFAOYSA-N ethyl 5-(4,4-difluorobut-3-enylsulfonyl)-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1S(=O)(=O)CCC=C(F)F OBWMABLVPSCXAS-UHFFFAOYSA-N 0.000 description 1
- MEUSJJFWVKBUFP-UHFFFAOYSA-N ethyl 5-amino-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1N MEUSJJFWVKBUFP-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- QKWRNBNHSRYCOE-UHFFFAOYSA-N hexanehydrazide Chemical compound CCCCCC(=O)NN QKWRNBNHSRYCOE-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- MLXWMEFKFOSOCP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical compound C1=CC=CC2=C=N[CH]N21 MLXWMEFKFOSOCP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 1
- MFKWKFKGUSAPCD-UHFFFAOYSA-N methyl 2-(4,4-difluorobut-3-enylsulfanyl)-5-ethyl-1-methylimidazole-4-carboxylate Chemical compound CCC1=C(C(=O)OC)N=C(SCCC=C(F)F)N1C MFKWKFKGUSAPCD-UHFFFAOYSA-N 0.000 description 1
- WLMIXLXCTUACQB-UHFFFAOYSA-N methyl 2-amino-4-methyl-1,3-oxazole-5-carboxylate Chemical compound COC(=O)C=1OC(N)=NC=1C WLMIXLXCTUACQB-UHFFFAOYSA-N 0.000 description 1
- BSOZQBHLQIMXEL-UHFFFAOYSA-N methyl 2-bromo-3-oxopentanoate Chemical compound CCC(=O)C(Br)C(=O)OC BSOZQBHLQIMXEL-UHFFFAOYSA-N 0.000 description 1
- KRTBUBWQNTZPBI-UHFFFAOYSA-N methyl 2-chloro-4-methyl-1,3-oxazole-5-carboxylate Chemical compound COC(=O)C=1OC(Cl)=NC=1C KRTBUBWQNTZPBI-UHFFFAOYSA-N 0.000 description 1
- DVBOFIBBCJQFBE-UHFFFAOYSA-N methyl 4-methyl-2-sulfanylidene-3h-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(S)=NC=1C DVBOFIBBCJQFBE-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002916 oxazoles Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- MNOALXGAYUJNKX-UHFFFAOYSA-N s-chloro chloromethanethioate Chemical compound ClSC(Cl)=O MNOALXGAYUJNKX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- JJJPTTANZGDADF-UHFFFAOYSA-N thiadiazole-4-thiol Chemical class SC1=CSN=N1 JJJPTTANZGDADF-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003564 thiocarbonyl compounds Chemical class 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- DSTCFVLLZSQKGQ-UHFFFAOYSA-N trifluoromethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(F)(F)F DSTCFVLLZSQKGQ-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen 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
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
-
- 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
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/18—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/18—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/04—1,2,3-Triazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
- C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/46—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/58—Nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/64—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9404716A GB9404716D0 (en) | 1994-03-10 | 1994-03-10 | Heterocyclic compounds |
| GB9404719A GB9404719D0 (en) | 1994-03-10 | 1994-03-10 | Heterocyclic compounds |
| GB9404721A GB9404721D0 (en) | 1994-03-10 | 1994-03-10 | Heterocyclic compounds |
| GB9404720A GB9404720D0 (en) | 1994-03-10 | 1994-03-10 | Heterocyclic compounds |
| GB9404718A GB9404718D0 (en) | 1994-03-10 | 1994-03-10 | Aromatic and heterocyclic compounds |
| GB9404717A GB9404717D0 (en) | 1994-03-10 | 1994-03-10 | Heterocyclic compounds |
| GBGB9500521.1A GB9500521D0 (en) | 1995-01-11 | 1995-01-11 | Heterocyclic compounds |
| PCT/GB1995/000400 WO1995024403A1 (en) | 1994-03-10 | 1995-02-27 | (4,4-difluorobut-3-enylthio)-substituted heterocyclic or carbocyclic ring compounds having pesticidal activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG100900A BG100900A (en) | 1997-07-31 |
| BG62809B1 true BG62809B1 (bg) | 2000-08-31 |
Family
ID=27562903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG100900A BG62809B1 (bg) | 1994-03-10 | 1996-10-10 | (4,4-дифлуоробут-3-енилтио)-заместени хетероциклени иликарбоциклени пръстенни съединения с пестицидна активност |
Country Status (31)
| Country | Link |
|---|---|
| US (3) | US5912243A (de) |
| EP (1) | EP0749433B1 (de) |
| JP (1) | JP3857722B2 (de) |
| KR (1) | KR100245904B1 (de) |
| CN (1) | CN1143958A (de) |
| AP (1) | AP649A (de) |
| AT (1) | ATE239714T1 (de) |
| AU (1) | AU685242B2 (de) |
| BG (1) | BG62809B1 (de) |
| BR (1) | BR9507042A (de) |
| CA (1) | CA2182520A1 (de) |
| CZ (1) | CZ285605B6 (de) |
| DE (1) | DE69530681T2 (de) |
| DK (1) | DK0749433T3 (de) |
| EE (1) | EE9600123A (de) |
| ES (1) | ES2199240T3 (de) |
| FI (1) | FI963539A0 (de) |
| HU (1) | HU215211B (de) |
| IL (1) | IL112721A0 (de) |
| LV (1) | LV11686B (de) |
| MX (1) | MX9603956A (de) |
| NO (1) | NO963776L (de) |
| NZ (1) | NZ281267A (de) |
| OA (1) | OA10374A (de) |
| PL (1) | PL316175A1 (de) |
| PT (1) | PT749433E (de) |
| RO (1) | RO116399B1 (de) |
| RU (1) | RU2151147C1 (de) |
| SK (1) | SK281491B6 (de) |
| UA (1) | UA44732C2 (de) |
| WO (1) | WO1995024403A1 (de) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19542520A1 (de) * | 1995-11-15 | 1997-05-22 | Basf Ag | Substituierte 1-Methyl-3-phenylpyrazole |
| WO1997024340A1 (en) * | 1995-12-27 | 1997-07-10 | Takeda Chemical Industries, Ltd. | Oxazole derivatives, their production and use |
| US6297198B1 (en) | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
| GB9708280D0 (en) * | 1997-04-24 | 1997-06-18 | Zeneca Ltd | Novel process |
| US6262096B1 (en) | 1997-11-12 | 2001-07-17 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| WO1999052874A1 (en) * | 1998-04-10 | 1999-10-21 | Ube Industries, Ltd. | Difluoroalkene derivatives, process for producing the same, and agricultural or horticultural pest control agent |
| JP2000001481A (ja) * | 1998-04-13 | 2000-01-07 | Nippon Nohyaku Co Ltd | 1,2,3―チアジアゾ―ル誘導体又はその塩類及び有害生物防除剤並びにその使用方法 |
| UA60365C2 (uk) | 1998-06-04 | 2003-10-15 | Пфайзер Продактс Інк. | Похідні ізотіазолу, спосіб їх одержання, фармацевтична композиція та спосіб лікування гіперпроліферативного захворювання у ссавця |
| US6214852B1 (en) | 1998-10-21 | 2001-04-10 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| US6414156B2 (en) | 1998-10-21 | 2002-07-02 | Bristol-Myers Squibb Company | Process for preparing azacycloalkanoylaminothiazoles |
| CO5221041A1 (es) * | 1998-10-23 | 2002-11-28 | Dow Agrosciences Llc | Compuestos de 3-(fenil sustituido)-5-tienil-1.2.4- triazolo con actividad contra la mosca blanca y composiciones insecticidas que lo contienen |
| US6927214B1 (en) | 1999-01-15 | 2005-08-09 | Novo Nordisk A/S | Non-peptide GLP-1 agonists |
| JP2002534512A (ja) * | 1999-01-15 | 2002-10-15 | ノボ ノルディスク アクティーゼルスカブ | 非ペプチドglp−1アゴニスト |
| JP2001019685A (ja) * | 1999-07-06 | 2001-01-23 | Nippon Bayer Agrochem Co Ltd | 殺センチュウ性トリフルオロブテン類 |
| EP1204413A2 (de) * | 1999-07-23 | 2002-05-15 | Bioparken AS | Kontrolle von krustentierbefall von wassertieren |
| US6392053B2 (en) | 1999-12-15 | 2002-05-21 | Bristol-Myers Squibb Company | Process for preparing arylacetylaminothiazoles |
| US6515004B1 (en) | 1999-12-15 | 2003-02-04 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| JP2001322988A (ja) | 2000-03-09 | 2001-11-20 | Nippon Bayer Agrochem Co Ltd | 殺センチュウ性トリフルオロブテン類 |
| WO2001087863A1 (de) * | 2000-05-15 | 2001-11-22 | Basf Aktiengesellschaft | 3-arylisothiazole und ihre verwendung als herbizide |
| DE10034133A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (l) |
| DE10034132A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (lll) |
| DE10034131A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (II) |
| DE10034130A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (lV) |
| JP2003192675A (ja) | 2001-12-13 | 2003-07-09 | Bayer Ag | 殺センチュウ性トリフルオロブテニルイミダゾールチオエーテル誘導体 |
| DE10201238A1 (de) * | 2002-01-15 | 2003-07-24 | Bayer Cropscience Ag | Verfahren zur Herstellung von halogenierten 2-(3-Butenylsulfanyl)-1,3-thiazolen |
| US7560592B2 (en) * | 2002-02-19 | 2009-07-14 | Sat, Inc. | Active aromatic sulfonamide organic compounds and biocidal uses thereof |
| EP1475092A1 (de) * | 2003-05-06 | 2004-11-10 | 4Sc Ag | Hemmer des "quorum sensing" Mechanismus von Gramnegativen Bakterien |
| US7335779B2 (en) | 2002-03-08 | 2008-02-26 | Quonova, Llc | Modulation of pathogenicity |
| US7338969B2 (en) | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
| CA2489355A1 (en) * | 2002-06-13 | 2003-12-24 | Qlt Inc. | Methods of using isothiazole derivatives to treat cancer or inflammation |
| JP2004018430A (ja) * | 2002-06-14 | 2004-01-22 | Bayer Ag | 殺センチュウ性テトラゾール含有トリフルオロブテン誘導体 |
| DE10229776A1 (de) | 2002-07-03 | 2004-01-22 | Bayer Cropscience Ag | Verfahren zum Herstellen von heterocyclischen Fluoralkenylsulfonen |
| WO2004004454A2 (en) * | 2002-07-08 | 2004-01-15 | Isca Technologies | Method of producing vertebrate host mimic with modified lipid based media |
| AU2003281664A1 (en) * | 2002-07-25 | 2004-02-16 | Pfizer Products Inc. | Isothiazole derivatives useful as anticancer agents |
| DE10238725A1 (de) * | 2002-08-23 | 2004-03-04 | Bayer Cropscience Ag | Substituierte Heterocyclypyrimidine |
| DE10319591A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden, insektiziden und fungiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
| DE10319590A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden und insektiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
| JP2005008567A (ja) * | 2003-06-19 | 2005-01-13 | Bayer Cropscience Ag | 殺センチュウ性チアゾリン含有フルオロブテン類 |
| JP2005089383A (ja) * | 2003-09-18 | 2005-04-07 | Bayer Cropscience Ag | 新規チアジアゾール含有ジフルオロアルケン類及び有害生物防除剤としての利用 |
| EP1694128A4 (de) * | 2003-12-18 | 2007-04-18 | Huntsman Spec Chem Corp | Pestizidgranulat mit verbesserter oberfläche mit rascher wirkstofffreigabe |
| FR2889192A1 (fr) * | 2005-07-27 | 2007-02-02 | Cytomics Systems Sa | Composes antifongiques, compositions contenant ces composes et leurs utilisations |
| WO2007022453A2 (en) * | 2005-08-19 | 2007-02-22 | Sat, Inc. | Active aromatic sulfonamide organic compounds and biocidal uses thereof |
| JP5101508B2 (ja) * | 2005-08-29 | 2012-12-19 | ノバルティス アーゲー | 魚寄生虫制御のためのオキサゾール誘導体の使用 |
| RU2293720C1 (ru) * | 2005-12-06 | 2007-02-20 | Ооо "Эстеркем" | Способ восстановления ненасыщенных кетонов в насыщенные кетоны |
| HUE036519T2 (hu) * | 2007-08-13 | 2018-07-30 | Monsanto Technology Llc | Készítmények és eljárások nematódák irtására |
| JP5287033B2 (ja) * | 2007-08-23 | 2013-09-11 | 住友化学株式会社 | 含フッ素有機硫黄化合物およびその有害節足動物防除剤 |
| EP2112143A1 (de) | 2008-04-22 | 2009-10-28 | Bayer CropScience AG | 2-(Benzylsulfonyl)-Oxazol-Derivate, chirale 2-(Benzylsulfinyl)-Oxazol-Derivate 2-(Benzylsulfanyl-Oxazol Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| EP2112149A1 (de) | 2008-04-22 | 2009-10-28 | Bayer CropScience Aktiengesellschaft | 2-[(1h-Pyrazol-4-ylmethyl)-sulfonyl]-Oxazol-Derivate, 2-[(1H-Pyrazol-4-ylmethyl)-sulfanyl]-Oxazol-Derivate und chirale 2-[(1H-Pyrazol-4-ylmethyl)-sulfinyl]-Oxazol-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| HUE025314T2 (en) | 2009-02-10 | 2016-02-29 | Monsanto Technology Llc | Preparations and procedures for controlling nematodes |
| BR112012011808B1 (pt) * | 2009-11-17 | 2020-02-04 | Merial Ltd | derivados heteroarilalquilsulfeto oxa tio fluorados para combater pragas invertebradas. |
| EP2545964A1 (de) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Neuartige FXR- (NR1H4)-Binde- und -Aktivitätsmodulationsverbindungen |
| CN102696609B (zh) * | 2012-01-10 | 2013-09-11 | 山东中农联合生物科技有限公司 | 一种含吡啶的三氟丁烯类杀虫剂 |
| CN102757400B (zh) * | 2012-07-18 | 2014-08-06 | 贵州大学 | 2,5-取代基噁唑类衍生物及其应用 |
| UA118254C2 (uk) | 2012-12-04 | 2018-12-26 | Монсанто Текнолоджи Ллс | Нематоцидні водні композиції концентрату суспензії |
| ITUB20153829A1 (it) * | 2015-09-23 | 2017-03-23 | Isagro Spa | Composti eterociclici trifluoroalchenilici ad attivita nematocida, loro composizioni agronomiche e relativo uso |
| CN106554335B (zh) * | 2015-09-30 | 2017-09-19 | 山东省联合农药工业有限公司 | 一种反式结构的含内酯环的杀线虫剂及其制备方法和用途 |
| CN105646393A (zh) * | 2016-03-31 | 2016-06-08 | 贵州大学 | 含三氟丁烯的1,3,4-噁(噻)二唑硫醚(砜)类衍生物、其制备方法及应用 |
| BR112018075734A2 (pt) | 2016-06-13 | 2019-04-02 | Gilead Sciences, Inc. | composto, composição farmacêutica, método para tratar um paciente com uma doença ou condição mediada pelo menos em parte por fxr, e, uso de um composto. |
| CA3252823A1 (en) | 2016-06-13 | 2025-02-25 | Gilead Sciences, Inc. | Substituted tert-butyl-3-(2-chloro-phenyl)-3-hydroxyazetidine-1-carboxylate compounds |
| WO2018137128A1 (zh) * | 2017-01-24 | 2018-08-02 | 郭庆春 | 预防和/或治疗姜瘟的组合物、方法和噁二唑类化合物用于预防和/或治疗姜瘟的用途 |
| CN110461328A (zh) | 2017-03-28 | 2019-11-15 | 吉利德科学公司 | 治疗肝疾病的治疗组合 |
| BR112020012614A2 (pt) | 2017-12-20 | 2020-11-24 | Pi Industries Ltd | compostos de fluoralquenil, processo de preparação e utilização |
| IT201800006066A1 (it) * | 2018-06-06 | 2019-12-06 | Processo per la preparazione di derivati tiadiazolici | |
| PY1980072A (es) * | 2018-09-26 | 2020-06-05 | Adama Makhteshim Ltd | Proceso e intermedios para la preparación de fluensulfona |
| WO2020095161A1 (en) | 2018-11-05 | 2020-05-14 | Pi Industries Ltd. | Nitrone compounds and use thereof |
| EP4360632B1 (de) | 2019-01-15 | 2025-10-29 | Gilead Sciences, Inc. | Fxr (nr1h4) modulierende verbindungen |
| US11524005B2 (en) | 2019-02-19 | 2022-12-13 | Gilead Sciences, Inc. | Solid forms of FXR agonists |
| US11725080B2 (en) | 2020-03-05 | 2023-08-15 | The Boeing Company | Schiff base oligomers |
| US12497489B2 (en) | 2020-03-05 | 2025-12-16 | The Boeing Company | Schiff base oligomers |
| US11713374B2 (en) | 2020-03-05 | 2023-08-01 | The Boeing Company | Schiff base oligomers |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US378050A (en) * | 1888-02-14 | Automatic gas-light governor | ||
| US3223707A (en) * | 1963-12-23 | 1965-12-14 | Stauffer Chemical Co | 2-(trifluorobutenylmercapto)-pyrimidines |
| US4059635A (en) * | 1969-02-13 | 1977-11-22 | Hironari Sugiyama | Substituted derivatives of 1,1-dichloroalkene-1 and their preparation and uses |
| US4089964A (en) * | 1969-02-13 | 1978-05-16 | Kumiai Chemical Industry Co., Ltd. | Method of controlling fungal diseases in plants and compositions effective therefor |
| US3780050A (en) * | 1969-11-20 | 1973-12-18 | Stauffer Chemical Co | 2-thiobenzoxazolyl and 2-thiobenzothiazolyl trifluoro butenyl compounds |
| CA962281A (en) * | 1971-08-21 | 1975-02-04 | Sameeh S. Toukan | Fluorinated alkyl sulfides and process for their preparation |
| DE2533604A1 (de) * | 1975-07-26 | 1977-02-10 | Bayer Ag | 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide |
| DE3602728A1 (de) * | 1985-05-17 | 1986-11-20 | Bayer Ag, 51373 Leverkusen | Schaedlingsbekaempfungsmittel auf basis von pyrazolderivaten |
| US4952580A (en) * | 1985-06-20 | 1990-08-28 | Fmc Corporation | Pesticidal polyhaloalkene derivatives |
| WO1986007590A1 (en) * | 1985-06-20 | 1986-12-31 | Fmc Corporation | Pesticidal polyhaloalkene derivatives |
| DE3529829A1 (de) * | 1985-08-21 | 1987-02-26 | Bayer Ag | 1-arylpyrazole |
| EP0217747B1 (de) * | 1985-09-30 | 1991-11-21 | Ciba-Geigy Ag | Nematizide Mittel |
| DE3600287A1 (de) * | 1986-01-08 | 1987-07-16 | Bayer Ag | 1-arylpyrazole |
| DE3606476A1 (de) * | 1986-02-28 | 1987-09-03 | Bayer Ag | 1-arylpyrazole |
| DE3617554A1 (de) * | 1986-05-24 | 1987-11-26 | Bayer Ag | 5-oxy(thio)-pyrazol-derivate |
| DE3625686A1 (de) * | 1986-07-30 | 1988-02-04 | Bayer Ag | 4-cyano(nitro)-5-oxy(thio)-pyrazol-derivate |
| DE3711928A1 (de) * | 1987-04-09 | 1988-10-20 | Bayer Ag | Substituierte 1-arylpyrazole |
| ATE80878T1 (de) * | 1987-12-18 | 1992-10-15 | Ciba Geigy Ag | 2-thio-5-difluoromethylthio-1,3,4-thiadiazole und diese enthaltende nematizide mittel. |
| JPH01261381A (ja) * | 1988-04-12 | 1989-10-18 | Nippon Soda Co Ltd | オキサ(チア)ジアゾール誘導体、その製造方法及び殺ダニ剤 |
| IL90192A0 (en) * | 1988-05-13 | 1989-12-15 | Schering Ag | Azole ether derivatives and pesticidal compositions containing the same |
| DE3821953A1 (de) * | 1988-06-27 | 1989-12-28 | Schering Ag | 1,3,4-thiadiazole, verfahren zu ihrer herstellung und verwendung als schaedlingsbekaempfungsmittel |
| DE3842970A1 (de) * | 1988-07-20 | 1990-01-25 | Bayer Ag, 51373 Leverkusen | 4-halogen-5-nitrothiazol-derivate, verfahren zu ihrer herstellung, ihre verwendung als schaedlingsbekaempfungsmittel und neue zwischenprodukte |
| FR2645536B1 (fr) * | 1989-04-10 | 1991-05-31 | Rhone Poulenc Agrochimie | Composes herbicides et les compositions les contenant |
| DD295522A5 (de) * | 1989-07-26 | 1991-11-07 | �����@������������������k�� | 5-Alkyl-1,3,4-Thiadiazole, Verfahren zu ihrer Herstellung und Verwendung als Schädlingsbekämpfungsmittel |
| DE3933092A1 (de) * | 1989-10-04 | 1991-04-11 | Bayer Ag | Substituierte 1,3,4-thiadiazolinone verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von endoparasiten |
| GB9205484D0 (en) * | 1991-03-28 | 1992-04-29 | Ici Plc | Heterocyclic compounds |
| EP0507464A1 (de) * | 1991-03-28 | 1992-10-07 | Zeneca Limited | Benzoxazole Derivate |
| GB9106609D0 (en) * | 1991-03-28 | 1991-05-15 | Ici Plc | Heterocyclic compounds |
| GB9205487D0 (en) * | 1991-03-28 | 1992-04-29 | Ici Plc | Heterocyclic compounds |
| GB9219635D0 (en) * | 1992-09-16 | 1992-10-28 | Ici Plc | Heterocyclic compounds |
| GB9219634D0 (en) * | 1992-09-16 | 1992-10-28 | Ici Plc | Heterocyclic compounds |
| GB9219632D0 (en) * | 1992-09-16 | 1992-10-28 | Ici Plc | Heterocyclic compounds |
| EP0712395B1 (de) * | 1993-08-05 | 2002-05-22 | Syngenta Limited | Verfahren zur herstellung von fluoralkenylthio heterozyclische derivate |
| US5502054A (en) * | 1994-08-11 | 1996-03-26 | Fmc Corporation | 6-substituted-3,5-diamino-1,2,4-triazines as insecticides |
-
1995
- 1995-02-21 IL IL11272195A patent/IL112721A0/xx unknown
- 1995-02-27 AU AU18164/95A patent/AU685242B2/en not_active Ceased
- 1995-02-27 DK DK95909854T patent/DK0749433T3/da active
- 1995-02-27 WO PCT/GB1995/000400 patent/WO1995024403A1/en not_active Ceased
- 1995-02-27 EE EE9600123A patent/EE9600123A/xx unknown
- 1995-02-27 US US08/702,623 patent/US5912243A/en not_active Expired - Lifetime
- 1995-02-27 JP JP52328695A patent/JP3857722B2/ja not_active Expired - Fee Related
- 1995-02-27 MX MX9603956A patent/MX9603956A/es unknown
- 1995-02-27 BR BR9507042A patent/BR9507042A/pt not_active Application Discontinuation
- 1995-02-27 CZ CZ962632A patent/CZ285605B6/cs not_active IP Right Cessation
- 1995-02-27 ES ES95909854T patent/ES2199240T3/es not_active Expired - Lifetime
- 1995-02-27 CA CA002182520A patent/CA2182520A1/en not_active Abandoned
- 1995-02-27 NZ NZ281267A patent/NZ281267A/en unknown
- 1995-02-27 AT AT95909854T patent/ATE239714T1/de active
- 1995-02-27 KR KR1019960705000A patent/KR100245904B1/ko not_active Expired - Fee Related
- 1995-02-27 EP EP95909854A patent/EP0749433B1/de not_active Expired - Lifetime
- 1995-02-27 RO RO96-01788A patent/RO116399B1/ro unknown
- 1995-02-27 CN CN95192029A patent/CN1143958A/zh active Pending
- 1995-02-27 DE DE69530681T patent/DE69530681T2/de not_active Expired - Lifetime
- 1995-02-27 PT PT95909854T patent/PT749433E/pt unknown
- 1995-02-27 SK SK1148-96A patent/SK281491B6/sk unknown
- 1995-02-27 UA UA96103847A patent/UA44732C2/uk unknown
- 1995-02-27 PL PL95316175A patent/PL316175A1/xx unknown
- 1995-02-27 AP APAP/P/1996/000862A patent/AP649A/en active
- 1995-02-27 RU RU96120148/04A patent/RU2151147C1/ru active
- 1995-02-27 HU HU9602417A patent/HU215211B/hu not_active IP Right Cessation
- 1995-03-08 US US08/400,912 patent/US5705516A/en not_active Expired - Fee Related
-
1996
- 1996-09-09 NO NO963776A patent/NO963776L/no unknown
- 1996-09-09 FI FI963539A patent/FI963539A0/fi unknown
- 1996-09-10 OA OA60887A patent/OA10374A/en unknown
- 1996-09-10 LV LVP-96-363A patent/LV11686B/en unknown
- 1996-10-10 BG BG100900A patent/BG62809B1/bg unknown
-
1997
- 1997-07-03 US US08/887,858 patent/US5952359A/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5705516A (en) | Oxazoles and their agricultural compositions | |
| CN101747276B (zh) | 具有含氮五元杂环的醚类化合物及其应用 | |
| KR101278609B1 (ko) | 이속사졸린 유도체 및 제초제로서의 그들의 용도 | |
| CN102947296B (zh) | 用于防治害虫的5-芳基异噁唑啉 | |
| US5451594A (en) | Heterocyclic compounds | |
| JPH08503932A (ja) | 駆虫活性を有する複素環式化合物 | |
| NZ521227A (en) | Trifluorobutenes their preparation and use as a nematicidal agent | |
| GB2293380A (en) | Pesticidal heterocyclic and phenyl compounds | |
| JP4409944B2 (ja) | ジフルオロアルケン誘導体、それを含有する有害生物防除剤及びその製造中間体 | |
| EP1129083A1 (de) | Isothiazolecarbonsäure derivate | |
| US5891897A (en) | Oxopropionitrile derivative and vermin controlling agent | |
| WO1994006783A1 (en) | Benzoxazole and benzothiazole derivatives | |
| JP2005089383A (ja) | 新規チアジアゾール含有ジフルオロアルケン類及び有害生物防除剤としての利用 | |
| JP2002241358A (ja) | オキシム基を有する化合物及び殺虫・殺ダニ剤 | |
| Youssef et al. | Recent Trends in the Chemistry of Heterocyclic Sulfides, 1990–2000 | |
| JPH1029975A (ja) | セミカルバゾン誘導体及び有害生物防除剤 | |
| CN119059984A (zh) | 取代的环己烯类化合物、制备方法及应用 | |
| JPWO1996033995A1 (ja) | オキソプロピオニトリル誘導体および害虫防除剤 | |
| JP2002226463A (ja) | ヘテロ環イミノ化合物の製造法 |