CN1104636A - 新的除草剂 - Google Patents

新的除草剂 Download PDF

Info

Publication number: CN1104636A
Authority: CN; China
Prior art keywords: methyl; trifluoromethylpyrazole; difluorophenyl; carbonylamino; optionally substituted
Prior art date: 1992-06-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

CN93108724A

Other languages

English (en)

Chinese (zh)

Inventor

米歇尔·琴奇尔

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Agriculture Ltd

Original Assignee

Rhone Poulenc Agriculture Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-06-11

Filing date

1993-06-11

Publication date

1995-07-05

1992-06-11 Priority claimed from GB929212383A external-priority patent/GB9212383D0/en

1992-11-19 Priority claimed from GB929224280A external-priority patent/GB9224280D0/en

1993-03-25 Priority claimed from GB939306180A external-priority patent/GB9306180D0/en

1993-06-11 Application filed by Rhone Poulenc Agriculture Ltd filed Critical Rhone Poulenc Agriculture Ltd

1995-07-05 Publication of CN1104636A publication Critical patent/CN1104636A/zh

Status Pending legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 36
239000004009 herbicide Substances 0.000 title description 6
-1 N-substituted pyrazole Chemical class 0.000 claims abstract description 69
150000001875 compounds Chemical class 0.000 claims description 174
125000004432 carbon atom Chemical group C* 0.000 claims description 72
239000000203 mixture Substances 0.000 claims description 70
241000196324 Embryophyta Species 0.000 claims description 63
229910052736 halogen Inorganic materials 0.000 claims description 54
150000002367 halogens Chemical class 0.000 claims description 54
125000000217 alkyl group Chemical group 0.000 claims description 52
125000005843 halogen group Chemical group 0.000 claims description 50
238000006243 chemical reaction Methods 0.000 claims description 41
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 33
125000004093 cyano group Chemical group *C#N 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 21
239000003085 diluting agent Substances 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000001301 oxygen Substances 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
239000004094 surface-active agent Substances 0.000 claims description 18
125000003342 alkenyl group Chemical group 0.000 claims description 17
125000004434 sulfur atom Chemical group 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 9
238000006193 diazotization reaction Methods 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
238000006467 substitution reaction Methods 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
230000002140 halogenating effect Effects 0.000 claims description 5
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
238000009395 breeding Methods 0.000 claims 2
230000001488 breeding effect Effects 0.000 claims 2
150000001266 acyl halides Chemical class 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
239000007787 solid Substances 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
238000010992 reflux Methods 0.000 description 32
239000002904 solvent Substances 0.000 description 32
239000000243 solution Substances 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000012442 inert solvent Substances 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
239000002585 base Substances 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
235000013339 cereals Nutrition 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 12
239000000706 filtrate Substances 0.000 description 11
239000011734 sodium Substances 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
239000002253 acid Substances 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000002689 soil Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
235000008504 concentrate Nutrition 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 8
229940125904 compound 1 Drugs 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000969 carrier Substances 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
238000011282 treatment Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
240000001592 Amaranthus caudatus Species 0.000 description 6
235000009328 Amaranthus caudatus Nutrition 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
230000006378 damage Effects 0.000 description 5
239000008187 granular material Substances 0.000 description 5
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
238000005507 spraying Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 5
IKGVBNQPAJOSFP-UHFFFAOYSA-N 5-chloro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CN1N=C(C(F)(F)F)C(C(O)=O)=C1Cl IKGVBNQPAJOSFP-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
244000075850 Avena orientalis Species 0.000 description 4
244000025254 Cannabis sativa Species 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
241000209504 Poaceae Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
208000014674 injury Diseases 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000004033 plastic Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000004550 soluble concentrate Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
239000012414 tert-butyl nitrite Substances 0.000 description 4
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
241001290610 Abildgaardia Species 0.000 description 3
235000007320 Avena fatua Nutrition 0.000 description 3
235000006463 Brassica alba Nutrition 0.000 description 3
235000011371 Brassica hirta Nutrition 0.000 description 3
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 3
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
241000234646 Cyperaceae Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
244000098338 Triticum aestivum Species 0.000 description 3
235000005373 Uvularia sessilifolia Nutrition 0.000 description 3
241001506766 Xanthium Species 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
235000009120 camo Nutrition 0.000 description 3
235000005607 chanvre indien Nutrition 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000011487 hemp Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
239000002562 thickening agent Substances 0.000 description 3
XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 2
DXOCFMLDHNZWFC-UHFFFAOYSA-N 1-ethyl-5-ethylsulfanyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CCSC1=C(C(O)=O)C(C(F)(F)F)=NN1CC DXOCFMLDHNZWFC-UHFFFAOYSA-N 0.000 description 2
LVCVIYROIVOGBN-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbaldehyde Chemical compound CN1N=C(C(F)(F)F)C(C=O)=C1OC1=CC=CC(C(F)(F)F)=C1 LVCVIYROIVOGBN-UHFFFAOYSA-N 0.000 description 2
CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 2
JXPVQFCUIAKFLT-UHFFFAOYSA-N 2,5-dimethyl-1h-pyrazol-3-one Chemical compound CC1=CC(=O)N(C)N1 JXPVQFCUIAKFLT-UHFFFAOYSA-N 0.000 description 2
BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
OGPGQZOLRRPBEN-UHFFFAOYSA-N 5-(4-fluorophenyl)sulfanyl-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CN1N=C(C(F)(F)F)C(C(O)=O)=C1SC1=CC=C(F)C=C1 OGPGQZOLRRPBEN-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
244000237956 Amaranthus retroflexus Species 0.000 description 2
235000003276 Apios tuberosa Nutrition 0.000 description 2
244000178993 Brassica juncea Species 0.000 description 2
240000007124 Brassica oleracea Species 0.000 description 2
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
244000025670 Eleusine indica Species 0.000 description 2
235000014716 Eleusine indica Nutrition 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
240000007377 Petunia x hybrida Species 0.000 description 2
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ISXSFOPKZQZDAO-UHFFFAOYSA-N formaldehyde;sodium Chemical compound [Na].O=C ISXSFOPKZQZDAO-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000000227 grinding Methods 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
BAZZERBWEWNHPP-UHFFFAOYSA-N methyl n-(1-butyl-4-carbamoylbenzimidazol-2-yl)carbamate Chemical compound C1=CC=C2N(CCCC)C(NC(=O)OC)=NC2=C1C(N)=O BAZZERBWEWNHPP-UHFFFAOYSA-N 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
UHBMFGPURFTEIV-UHFFFAOYSA-N o-methyl 2-cyano-3-methylbut-2-enethioate Chemical compound COC(=S)C(C#N)=C(C)C UHBMFGPURFTEIV-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229960000490 permethrin Drugs 0.000 description 1
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
239000001294 propane Substances 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
229940070846 pyrethrins Drugs 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical class CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
239000004552 water soluble powder Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- C07D231/20—One oxygen atom attached in position 3 or 5
- 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
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen 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
- C07D231/32—Oxygen atoms
- C07D231/36—Oxygen atoms with hydrocarbon radicals, substituted by hetero atoms, attached in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Surgical Instruments (AREA)

CN93108724A 1992-06-11 1993-06-11 新的除草剂 Pending CN1104636A (zh)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GB9212383.5		1992-06-11
GB929212383A GB9212383D0 (en)	1992-06-11	1992-06-11	New compositions of matter
GB929224280A GB9224280D0 (en)	1992-11-19	1992-11-19	New compositions of matter
GB9224280.9		1992-11-19
GB939306180A GB9306180D0 (en)	1993-03-25	1993-03-25	Compositions of new matter
GB936180.2		1993-03-25

Publications (1)

Publication Number	Publication Date
CN1104636A true CN1104636A (zh)	1995-07-05

Family

ID=27266241

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN93108724A Pending CN1104636A (zh)	1992-06-11	1993-06-11	新的除草剂

Country Status (19)

Country	Link
EP (1)	EP0644879A1 (2)
JP (1)	JPH07507781A (2)
KR (1)	KR950701913A (2)
CN (1)	CN1104636A (2)
AU (1)	AU4324793A (2)
BR (1)	BR9306676A (2)
CA (1)	CA2137689A1 (2)
CZ (1)	CZ311894A3 (2)
FI (1)	FI945791A7 (2)
HU (1)	HU9403545D0 (2)
IL (1)	IL105939A0 (2)
MA (1)	MA22906A1 (2)
MX (1)	MX9303473A (2)
SI (1)	SI9300317A (2)
SK (1)	SK152894A3 (2)
TR (1)	TR27271A (2)
TW (1)	TW242619B (2)
WO (1)	WO1993025535A1 (2)
ZW (1)	ZW7593A1 (2)

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CN103524419A (zh) *	2013-10-18	2014-01-22	孙家隆	一组3-三氟甲基吡唑化合物
CN105418505A (zh) *	2015-12-21	2016-03-23	浙江树人大学	吡唑酰胺类化合物及其制备法与用途
CN108059614A (zh) *	2016-11-09	2018-05-22	沈阳中化农药化工研发有限公司	吡唑酰胺类化合物及其应用
CN108719301A (zh) *	2018-08-29	2018-11-02	浙江工业大学	一种1-甲基-3-三氟甲基-1h-吡唑-4-酰胺衍生物在制备除草剂中的应用
CN108863934A (zh) *	2018-08-29	2018-11-23	浙江工业大学	一种1-甲基-3-二氟甲基-1h-吡唑-4-酰胺衍生物在制备除草剂中的应用
CN108991003A (zh) *	2018-08-29	2018-12-14	浙江工业大学	一种含吡唑环的酰胺衍生物在制备除草剂中的应用
CN109156471A (zh) *	2018-08-29	2019-01-08	浙江工业大学	一种1，3-二甲基-1h-吡唑-4-酰胺衍生物在制备除草剂中的应用
CN109169693A (zh) *	2018-08-29	2019-01-11	浙江工业大学	一种新型含吡唑环的酰胺类化合物在制备除草剂中的应用
CN114105876A (zh) *	2021-12-08	2022-03-01	沈阳科创化学品有限公司	一种制备乙唑螨腈中间体的方法
CN119707818A (zh) *	2024-12-11	2025-03-28	河北农业大学	一类新型甲基吡唑丙酰胺衍生物及其制备方法和用途

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2692575B1 (fr) *	1992-06-23	1995-06-30	Sanofi Elf	Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant.
DE4417837A1 (de)	1994-05-20	1995-11-23	Basf Ag	Substituierte 3-Phenylpyrazole
JPH11509202A (ja) *	1995-07-10	1999-08-17	イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー	除草性スルホンアミド
CA2278307A1 (en) *	1997-01-21	1998-07-23	Siegfried Benjamin Christensen Iv	Novel cannabinoid receptor modulators
DE19854081A1 (de) *	1998-11-24	2000-05-25	Bayer Ag	Substituierte N-Pyrazolyl-phenoxynicotinsäure-(thio)amide
US7125875B2 (en)	1999-04-15	2006-10-24	Bristol-Myers Squibb Company	Cyclic protein tyrosine kinase inhibitors
CA2366932C (en)	1999-04-15	2009-08-25	Bristol-Myers Squibb Company	Cyclic protein tyrosine kinase inhibitors
AU2001277761A1 (en) *	2000-08-16	2002-02-25	Nippon Soda Co., Ltd.	Processes for the preparation of pyrazole compounds
AU2003218758A1 (en) *	2002-03-14	2003-09-22	Syngenta Participations Ag	Derivatives of 1-phenyl-3-phenylpyrazole as herbicides
WO2005040152A1 (en) *	2003-10-20	2005-05-06	E.I. Dupont De Nemours And Company	Heteroyclylphenyl-and heterocyclylpyridyl-substituted azolecarboxamides as herbicides
CN102659659B (zh)	2005-11-21	2014-07-23	盐野义制药株式会社	具有I型11β羟基类固醇脱氢酶抑制活性的杂环化合物
AU2008252185B2 (en)	2007-05-18	2012-02-16	Shionogi & Co., Ltd.	Nitrogen-containing heterocyclic derivative having 11 beta-hydroxysteroid dehydrogenase type I inhibitory activity
CN103140477B (zh) *	2010-04-23	2015-07-15	拜耳知识产权股份有限公司	制备5-氟-1-烷基-3-氟烷基-1h-吡唑-4-酰氯和酰氟的方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH03109302A (ja) *	1989-09-22	1991-05-09	Mitsubishi Kasei Corp	４―ピラゾールアミド類およびこれを有効成分とする除草剤

1993
- 1993-06-07 IL IL105939A patent/IL105939A0/xx unknown
- 1993-06-09 JP JP6501120A patent/JPH07507781A/ja active Pending
- 1993-06-09 CA CA002137689A patent/CA2137689A1/en not_active Abandoned
- 1993-06-09 AU AU43247/93A patent/AU4324793A/en not_active Abandoned
- 1993-06-09 HU HU9403545A patent/HU9403545D0/hu unknown
- 1993-06-09 SK SK1528-94A patent/SK152894A3/sk unknown
- 1993-06-09 BR BR9306676A patent/BR9306676A/pt not_active Application Discontinuation
- 1993-06-09 KR KR1019940704511A patent/KR950701913A/ko not_active Withdrawn
- 1993-06-09 TR TR00554/93A patent/TR27271A/xx unknown
- 1993-06-09 EP EP93912937A patent/EP0644879A1/en not_active Withdrawn
- 1993-06-09 CZ CZ943118A patent/CZ311894A3/cs unknown
- 1993-06-09 WO PCT/EP1993/001466 patent/WO1993025535A1/en not_active Ceased
- 1993-06-09 MA MA23205A patent/MA22906A1/fr unknown
- 1993-06-10 MX MX9303473A patent/MX9303473A/es unknown
- 1993-06-10 ZW ZW7593A patent/ZW7593A1/xx unknown
- 1993-06-11 CN CN93108724A patent/CN1104636A/zh active Pending
- 1993-06-11 TW TW082104643A patent/TW242619B/zh active
- 1993-06-11 SI SI9300317A patent/SI9300317A/sl unknown
1994
- 1994-12-09 FI FI945791A patent/FI945791A7/fi not_active Application Discontinuation

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CN103524419A (zh) *	2013-10-18	2014-01-22	孙家隆	一组3-三氟甲基吡唑化合物
CN103524419B (zh) *	2013-10-18	2016-03-23	孙家隆	一组3-三氟甲基吡唑化合物
CN105418505A (zh) *	2015-12-21	2016-03-23	浙江树人大学	吡唑酰胺类化合物及其制备法与用途
CN105418505B (zh) *	2015-12-21	2018-02-02	浙江树人大学	吡唑酰胺类化合物及其制备法与用途
CN108059614A (zh) *	2016-11-09	2018-05-22	沈阳中化农药化工研发有限公司	吡唑酰胺类化合物及其应用
CN108059614B (zh) *	2016-11-09	2020-09-01	沈阳中化农药化工研发有限公司	吡唑酰胺类化合物及其应用
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HU9403545D0 (en)	1995-02-28
FI945791A0 (fi)	1994-12-09
MX9303473A (es)	1994-02-28
CZ311894A3 (en)	1995-07-12
KR950701913A (ko)	1995-05-17
IL105939A0 (en)	1993-10-20
BR9306676A (pt)	1998-12-08
ZW7593A1 (en)	1994-03-30
TR27271A (tr)	1994-12-22
JPH07507781A (ja)	1995-08-31
MA22906A1 (fr)	1993-12-31
WO1993025535A1 (en)	1993-12-23
CA2137689A1 (en)	1993-12-23
SK152894A3 (en)	1995-06-07
EP0644879A1 (en)	1995-03-29
AU4324793A (en)	1994-01-04
SI9300317A (sl)	1993-12-31
TW242619B (2)	1995-03-11
FI945791A7 (fi)	1995-02-09

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