EA012667B1 - Анилиды пиразолкарбоновой кислоты и содержащее их средство для борьбы с патогенными грибами - Google Patents

Info

Publication number

EA012667B1

EA012667B1 EA200701624A EA200701624A EA012667B1 EA 012667 B1 EA012667 B1 EA 012667B1 EA 200701624 A EA200701624 A EA 200701624A EA 200701624 A EA200701624 A EA 200701624A EA 012667 B1 EA012667 B1 EA 012667B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

carboxylic acid

chloro

amide

pyrazole

Prior art date

2005-02-16

Links

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• Global Dossier
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• 244000053095 fungal pathogen Species 0.000 title claims abstract description 9
• WMZYZYFPPQOFKY-UHFFFAOYSA-N n-phenyl-1h-pyrazole-3-carboxamide Chemical class C1=CNN=C1C(=O)NC1=CC=CC=C1 WMZYZYFPPQOFKY-UHFFFAOYSA-N 0.000 title claims abstract description 7
• 239000003795 chemical substances by application Substances 0.000 title abstract description 14
• 150000001875 compounds Chemical class 0.000 claims abstract description 66
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
• 239000001257 hydrogen Substances 0.000 claims abstract description 38
• 239000000460 chlorine Substances 0.000 claims abstract description 27
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 27
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
• 239000011737 fluorine Substances 0.000 claims abstract description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 18
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 17
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
• 150000002367 halogens Chemical class 0.000 claims abstract description 7
• 238000000034 method Methods 0.000 claims abstract description 7
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 3
• -1 chloro, methyl Chemical group 0.000 claims description 592
• 239000013543 active substance Substances 0.000 claims description 46
• 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims description 11
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 11
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 10
• 239000000463 material Substances 0.000 claims description 10
• 241000233866 Fungi Species 0.000 claims description 9
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
• 229940051881 anilide analgesics and antipyretics Drugs 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 230000000855 fungicidal effect Effects 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 150000001408 amides Chemical class 0.000 claims description 7
• 239000000654 additive Substances 0.000 claims description 5
• QBVDQOUVCUSMQZ-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)aniline Chemical compound NC1=CC=CC=C1C1=CC=C(F)C(Cl)=C1 QBVDQOUVCUSMQZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 230000003032 phytopathogenic effect Effects 0.000 claims description 3
• 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• 239000002689 soil Substances 0.000 claims description 2
• KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 claims 12
• QRSKMQFPQWFKEJ-UHFFFAOYSA-N 3-(fluoromethyl)-1-methylpyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(CF)=N1 QRSKMQFPQWFKEJ-UHFFFAOYSA-N 0.000 claims 6
• 150000003931 anilides Chemical class 0.000 claims 6
• YCXSHQOLURVJBU-UHFFFAOYSA-N 3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1C=C(C(N)=O)C(CF)=N1 YCXSHQOLURVJBU-UHFFFAOYSA-N 0.000 claims 3
• RCMMYBDLXJUUNH-UHFFFAOYSA-N 3-chloro-5-(fluoromethyl)-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=C(Cl)C(C(O)=O)=C1CF RCMMYBDLXJUUNH-UHFFFAOYSA-N 0.000 claims 3
• FZNKJQNEJGXCJH-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(C(F)(F)F)=N1 FZNKJQNEJGXCJH-UHFFFAOYSA-N 0.000 claims 2
• RIHYIZHMUVNRQG-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-5-[2-(2,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC1=C(C=C(C(=C1)F)F)C1=C(C=CC=C1)C1=C(C(=NN1C)C(F)(F)F)C(=O)N RIHYIZHMUVNRQG-UHFFFAOYSA-N 0.000 claims 1
• FIGHASAJPPRLLR-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-5-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC=1C=C(C=C(C=1F)F)C1=C(C=CC=C1)C1=C(C(=NN1C)C(F)(F)F)C(=O)N FIGHASAJPPRLLR-UHFFFAOYSA-N 0.000 claims 1
• FAUNUHHYLCHKQZ-UHFFFAOYSA-N 3-chloro-5-(difluoromethyl)-n-[2-(3,4-difluorophenyl)phenyl]-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(F)C(F)=CC=2)=C1C(F)F FAUNUHHYLCHKQZ-UHFFFAOYSA-N 0.000 claims 1
• QLEFMAWTHPHXHJ-UHFFFAOYSA-N 3-chloro-5-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(N)=O)=C1CF QLEFMAWTHPHXHJ-UHFFFAOYSA-N 0.000 claims 1
• VGHWDCNCTJOJIF-UHFFFAOYSA-N 3-chloro-n-[2-(2,4-dichlorophenyl)phenyl]-5-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1C(F)F VGHWDCNCTJOJIF-UHFFFAOYSA-N 0.000 claims 1
• FAHMVDDDNZUPQO-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-dichlorophenyl)phenyl]-5-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)=C1C(F)F FAHMVDDDNZUPQO-UHFFFAOYSA-N 0.000 claims 1
• ZSKYXFNHIIXGMQ-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-dichlorophenyl)phenyl]-5-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)=C1CF ZSKYXFNHIIXGMQ-UHFFFAOYSA-N 0.000 claims 1
• IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 claims 1
• LZJOUHXBVDDXMJ-UHFFFAOYSA-N 5-chloro-n-[2-(3-chloro-4-fluorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(Cl)=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(Cl)=C1 LZJOUHXBVDDXMJ-UHFFFAOYSA-N 0.000 claims 1
• CAODACFCGIYNTJ-UHFFFAOYSA-N CN1C(=C(C(=N1)C(F)(F)F)C(=O)N)C2=CC=CC=C2C3=CC(=C(C=C3F)Cl)OC Chemical compound CN1C(=C(C(=N1)C(F)(F)F)C(=O)N)C2=CC=CC=C2C3=CC(=C(C=C3F)Cl)OC CAODACFCGIYNTJ-UHFFFAOYSA-N 0.000 claims 1
• XKMDWNXNVSQKQF-UHFFFAOYSA-N CN1C(=C(C(=N1)C(F)F)C(=O)N)C2=CC=CC=C2C3=CC(=C(C=C3F)Cl)OC Chemical compound CN1C(=C(C(=N1)C(F)F)C(=O)N)C2=CC=CC=C2C3=CC(=C(C=C3F)Cl)OC XKMDWNXNVSQKQF-UHFFFAOYSA-N 0.000 claims 1
• 230000000996 additive effect Effects 0.000 claims 1
• HYPQOPSPZIIVQA-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical class CN1N=C(C(F)(F)F)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)=C1F HYPQOPSPZIIVQA-UHFFFAOYSA-N 0.000 claims 1
• YSPYDPLBYANXHG-UHFFFAOYSA-N n-[2-(3,5-dichlorophenyl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CN1N=C(C(F)(F)F)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C=C(Cl)C=2)=C1F YSPYDPLBYANXHG-UHFFFAOYSA-N 0.000 claims 1
• HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 claims 1
• 230000001717 pathogenic effect Effects 0.000 claims 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 3
• 229910052794 bromium Inorganic materials 0.000 abstract description 3
• 229910052717 sulfur Inorganic materials 0.000 abstract description 3
• 150000004820 halides Chemical class 0.000 abstract 2
• 238000004519 manufacturing process Methods 0.000 abstract 1
• 239000000203 mixture Substances 0.000 description 34
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• 241000196324 Embryophyta Species 0.000 description 27
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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