CA2597022C - Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi - Google Patents
Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi Download PDFInfo
- Publication number
- CA2597022C CA2597022C CA2597022A CA2597022A CA2597022C CA 2597022 C CA2597022 C CA 2597022C CA 2597022 A CA2597022 A CA 2597022A CA 2597022 A CA2597022 A CA 2597022A CA 2597022 C CA2597022 C CA 2597022C
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- fluoro
- dichlorophenyl
- difluorophenyl
- methyl
- Prior art date
- 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.)
- Active
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- 238000000034 method Methods 0.000 title claims abstract description 13
- 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 10
- 239000003795 chemical substances by application Substances 0.000 title abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 244000053095 fungal pathogen Species 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 64
- 239000000460 chlorine Chemical group 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 229910052801 chlorine Chemical group 0.000 claims abstract description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 24
- 239000011737 fluorine Substances 0.000 claims abstract description 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 38
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- 239000000463 material Substances 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims description 9
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 9
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 8
- 230000000855 fungicidal effect Effects 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 230000002538 fungal effect Effects 0.000 claims description 2
- 230000003032 phytopathogenic effect Effects 0.000 claims description 2
- KYXNOBUGJXDOIO-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(2,3,4-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(F)=C1F KYXNOBUGJXDOIO-UHFFFAOYSA-N 0.000 claims 1
- SAEWEAKBGDVOPX-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(2,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C=C1F SAEWEAKBGDVOPX-UHFFFAOYSA-N 0.000 claims 1
- HDWGAKWQBOMENH-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 HDWGAKWQBOMENH-UHFFFAOYSA-N 0.000 claims 1
- OXBRSAWHLLAWFH-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-n-[2-(2,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C=C1F OXBRSAWHLLAWFH-UHFFFAOYSA-N 0.000 claims 1
- UIMRMZWPXAGXRL-UHFFFAOYSA-N 3-(fluoromethyl)-1-methyl-n-[2-(2,3,4-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(F)=C1F UIMRMZWPXAGXRL-UHFFFAOYSA-N 0.000 claims 1
- ACGQBCAWGUDTQW-UHFFFAOYSA-N 3-(fluoromethyl)-1-methyl-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 ACGQBCAWGUDTQW-UHFFFAOYSA-N 0.000 claims 1
- FDYQKQCEOKOFLX-UHFFFAOYSA-N 3-chloro-5-(difluoromethyl)-1-methyl-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(F)C(F)=C(F)C=2)=C1C(F)F FDYQKQCEOKOFLX-UHFFFAOYSA-N 0.000 claims 1
- QVEBGUHTZIXVCR-UHFFFAOYSA-N 3-chloro-5-(fluoromethyl)-1-methyl-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(F)C(F)=C(F)C=2)=C1CF QVEBGUHTZIXVCR-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 101
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052794 bromium Inorganic materials 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 abstract description 4
- -1 PYRAZOLE CARBOXYLIC ACID ANILIDES Chemical class 0.000 description 548
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- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 56
- 241000196324 Embryophyta Species 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
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- 238000009472 formulation Methods 0.000 description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
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- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- WBTYBAGIHOISOQ-UHFFFAOYSA-N pent-4-en-1-yl 2-[(2-furylmethyl)(imidazol-1-ylcarbonyl)amino]butanoate Chemical compound C1=CN=CN1C(=O)N(C(CC)C(=O)OCCCC=C)CC1=CC=CO1 WBTYBAGIHOISOQ-UHFFFAOYSA-N 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl chloride Substances ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
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- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- LBKJNHPKYFYCLL-UHFFFAOYSA-N potassium;trimethyl(oxido)silane Chemical compound [K+].C[Si](C)(C)[O-] LBKJNHPKYFYCLL-UHFFFAOYSA-N 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- WHMZYGMQWIBNOC-UHFFFAOYSA-N propan-2-yl n-(3,4-dimethoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)C)C=C1OC WHMZYGMQWIBNOC-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- KOPFEFZSAMLEHK-UHFFFAOYSA-N pyrazolecarboxylic acid Natural products OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 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
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- YWGZBLRRLREJIR-UHFFFAOYSA-N triazole-1-sulfonamide Chemical compound NS(=O)(=O)N1C=CN=N1 YWGZBLRRLREJIR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catching Or Destruction (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Insulated Conductors (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005007160A DE102005007160A1 (de) | 2005-02-16 | 2005-02-16 | Pyrazolcarbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| DE102005007160.0 | 2005-02-16 | ||
| PCT/EP2006/050962 WO2006087343A1 (de) | 2005-02-16 | 2006-02-15 | Pyrazolcarbonsäureanilide, verfahren zu ihrer herstellung und sie enthaltende mittel zur bekämpfung von schadpilzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2597022A1 CA2597022A1 (en) | 2006-08-24 |
| CA2597022C true CA2597022C (en) | 2013-05-07 |
Family
ID=36204373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2597022A Active CA2597022C (en) | 2005-02-16 | 2006-02-15 | Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi |
Country Status (33)
Families Citing this family (679)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008540605A (ja) * | 2005-05-18 | 2008-11-20 | ビーエーエスエフ ソシエタス・ヨーロピア | チアゾールカルボキサニリド |
| EP1901609A2 (de) * | 2005-07-05 | 2008-03-26 | Basf Se | Fungizide mischungen auf der basis von 3-monosubstituierten pyrazolcarbonsäurebiphenylamiden |
| HRP20141028T1 (hr) | 2005-08-05 | 2014-12-19 | Basf Se | Fungicidne smjese koje sadrže supstituirane anilide 1-metil-pirazol-4-ilkarboksilne kiseline |
| JP5227950B2 (ja) * | 2006-05-03 | 2013-07-03 | ビーエーエスエフ ソシエタス・ヨーロピア | 種子処理のためのアリールカルボン酸ビフェニルアミドの使用 |
| EP2489268A3 (en) | 2006-09-18 | 2012-10-24 | Basf Se | Pesticidal mixtures comprising an anthranilamide insecticide and a fungicide |
| US8063092B2 (en) | 2006-11-10 | 2011-11-22 | Basf Se | Crystalline modification of fipronil |
| KR101540122B1 (ko) | 2006-11-10 | 2015-07-28 | 바스프 에스이 | 피프로닐의 결정질 변형물 |
| UA110598C2 (uk) | 2006-11-10 | 2016-01-25 | Басф Се | Спосіб одержання кристалічної модифікації фіпронілу |
| UA95819C2 (ru) | 2006-11-10 | 2011-09-12 | Басф Се | Кристаллическая модификация iv фипронила, способ ее получения, применения, способы получения кристаллических модификаций v и i, пестицидная или паразитицидная композиция, способ контроля вредителей, способ защиты растения от заражения или нападения вредителей, способ защиты семян и способ лечения, контроля, предотвращения или защиты животных от заражения или инфекции паразитами |
| BRPI0806347A2 (pt) * | 2007-01-19 | 2011-09-06 | Basf Se | misturas fungicidas, agente fungicida, método para combater fungos nocivos fitopagênicos, semente, e, processo para preparar um agente |
| BRPI0806766A2 (pt) * | 2007-01-30 | 2011-09-13 | Basf Se | misturas pesticidas, métodos para melhorar a saúde de plantas, para controlar ou prevenir infestação fúngica em plantas, partes de planta, sementes, ou seu local de crescimento, para controlar ou prevenir nematódeos ou insetos nocivos em plantas, partes de planta, sementes, ou seu local de crescimento, e para proteger sementes, material de propagação de planta, semente, e, composição pesticida |
| EP2061320A2 (en) * | 2007-02-05 | 2009-05-27 | Basf Se | Fungicidal mixtures comprising substituted 1-methylpyrazol-4-ylcarboxanilides |
| EP2679095A1 (en) | 2007-02-06 | 2014-01-01 | Basf Se | Pesticidal mixtures |
| RS53057B (sr) * | 2007-07-12 | 2014-04-30 | Basf Se | Novi kristalni oblik 3-(difluorometil)-1-metil-n-(3`,4`,5`-trifluoro[1,1`-bifenil]-2-il)-1h-pirazol-4-karboksamida |
| EA019915B1 (ru) | 2007-09-20 | 2014-07-30 | Басф Се | Фунгицидная композиция для борьбы с фитопатогенными вредными грибами |
| CA2712488A1 (en) * | 2008-02-05 | 2009-08-13 | Basf Se | Plant health composition |
| KR20100113157A (ko) * | 2008-02-05 | 2010-10-20 | 바스프 에스이 | 살충성 혼합물 |
| EA018967B1 (ru) | 2008-02-05 | 2013-12-30 | Басф Се | Способ повышения выхода и/или повышения жизнеспособности и/или увеличения устойчивости или сопротивления к факторам абиотического стресса и фунгицидные смеси |
| UA103323C2 (ru) * | 2008-05-08 | 2013-10-10 | Басф Се | Способ получения арилкарбоксамидов |
| JP5481476B2 (ja) | 2008-06-25 | 2014-04-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 置換ビフェニル類の製造方法 |
| BRPI0914924A2 (pt) * | 2008-07-03 | 2015-10-20 | Basf Se | processo para preparar aminobifenilas, e, composto. |
| KR20110026018A (ko) * | 2008-07-04 | 2011-03-14 | 바스프 에스이 | 치환된 1-메틸피라졸-4-일카르복스아닐리드를 포함하는 살진균 혼합물 |
| EP2361015A2 (en) * | 2008-10-21 | 2011-08-31 | Basf Se | Use of carboxamides on cultivated plants |
| CA2750963A1 (en) | 2009-01-30 | 2010-08-05 | Bayer Cropscience Ag | Active compound combinations |
| ES2576122T3 (es) | 2009-01-30 | 2016-07-05 | Bayer Intellectual Property Gmbh | Uso de inhibidores de la succinato deshidrogenasa para controlar infecciones primarias por oidio |
| ES2530882T3 (es) | 2009-02-13 | 2015-03-06 | Bayer Ip Gmbh | Uso de fluopiram para ampliar la duración de frutas y hortalizas |
| US8492558B2 (en) | 2009-02-19 | 2013-07-23 | Basf Se | Method for producing 2-aminobiphenylene |
| WO2010103065A1 (en) | 2009-03-11 | 2010-09-16 | Basf Se | Fungicidal compositions and their use |
| BRPI1006773A2 (pt) | 2009-04-02 | 2020-12-01 | Basf Se | uso de pelo menos um filtro uv, método para reduzir danos por queimadura solar em uma planta de colheita e composição |
| GB0908435D0 (en) | 2009-05-15 | 2009-06-24 | Syngenta Ltd | Processes |
| CN102803230A (zh) | 2009-06-12 | 2012-11-28 | 巴斯夫欧洲公司 | 杀真菌的具有5-硫取代基的1，2，4-三唑衍生物 |
| WO2010146032A2 (de) | 2009-06-16 | 2010-12-23 | Basf Se | Fungizide mischungen |
| BRPI1010096A2 (pt) | 2009-06-18 | 2016-03-15 | Basf Se | compostos de formulas i e ii, composição agrícola, uso de um composto, método de controle de fungos nocivos, semente, composição farmacêutica, uso de um composto e método de tratamento contra o câncer ou infecções por vírus ou para combater a fungos zoopatogênicos ou humanopatogênicos |
| CN102803231A (zh) | 2009-06-18 | 2012-11-28 | 巴斯夫欧洲公司 | 杀真菌的1，2，4-三唑衍生物 |
| WO2010146116A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
| WO2010146115A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
| CN102459201A (zh) | 2009-06-18 | 2012-05-16 | 巴斯夫欧洲公司 | 杀真菌的1，2，4-三唑衍生物 |
| MX2011012903A (es) | 2009-06-18 | 2012-02-01 | Basf Se | Mezclas fungicidas. |
| CA2762512A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
| WO2010149758A1 (en) | 2009-06-25 | 2010-12-29 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
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| WO2006120219A1 (de) * | 2005-05-11 | 2006-11-16 | Basf Aktiengesellschaft | Pyrazolcarbonsäureamide als fungizide |
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