EP1898704A1 - Melanges fongicides a base d'amides de biphenyle d'acide pyrazolcarboxylique disubstitues en 2,5 - Google Patents
Melanges fongicides a base d'amides de biphenyle d'acide pyrazolcarboxylique disubstitues en 2,5Info
- Publication number
- EP1898704A1 EP1898704A1 EP06763920A EP06763920A EP1898704A1 EP 1898704 A1 EP1898704 A1 EP 1898704A1 EP 06763920 A EP06763920 A EP 06763920A EP 06763920 A EP06763920 A EP 06763920A EP 1898704 A1 EP1898704 A1 EP 1898704A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- methyl
- carboxylic acid
- amide
- chloro
- compounds
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 101
- -1 2,5-disubstituted pyrazol carboxylic acid biphenylamides Chemical class 0.000 title claims abstract description 99
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 241000233866 Fungi Species 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000011593 sulfur Chemical group 0.000 claims abstract description 10
- 229910052717 sulfur Chemical group 0.000 claims abstract description 10
- 239000000417 fungicide Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 150000003851 azoles Chemical class 0.000 claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 7
- 229930182692 Strobilurin Natural products 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims abstract description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 48
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- RLOHOBNEYHBZID-UHFFFAOYSA-N 3-(difluoromethyl)-1-methylpyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(C(F)F)=N1 RLOHOBNEYHBZID-UHFFFAOYSA-N 0.000 claims description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims description 8
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 claims description 8
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 8
- 239000005767 Epoxiconazole Substances 0.000 claims description 8
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 claims description 8
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 claims description 8
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 claims description 7
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 claims description 7
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 7
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 claims description 7
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 claims description 7
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 claims description 7
- 239000005785 Fluquinconazole Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000005868 Metconazole Substances 0.000 claims description 7
- 239000005859 Triticonazole Substances 0.000 claims description 7
- JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 claims description 7
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 claims description 7
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 claims description 7
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 claims description 7
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims description 6
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 claims description 6
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 claims description 6
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims description 6
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 claims description 6
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 6
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 claims description 6
- ASMNSUBMNZQTTG-UHFFFAOYSA-N 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC(F)=CC=2F)F)C(Cl)=NC2=NC=NN12 ASMNSUBMNZQTTG-UHFFFAOYSA-N 0.000 claims description 6
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims description 6
- 239000005765 Dodemorph Substances 0.000 claims description 6
- 239000005778 Fenpropimorph Substances 0.000 claims description 6
- 239000005787 Flutriafol Substances 0.000 claims description 6
- 239000005795 Imazalil Substances 0.000 claims description 6
- 239000005867 Iprodione Substances 0.000 claims description 6
- IUOKJNROJISWRO-UHFFFAOYSA-N N-(2-cyano-3-methylbutan-2-yl)-2-(2,4-dichlorophenoxy)propanamide Chemical compound CC(C)C(C)(C#N)NC(=O)C(C)OC1=CC=C(Cl)C=C1Cl IUOKJNROJISWRO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005869 Pyraclostrobin Substances 0.000 claims description 6
- 239000005828 Pyrimethanil Substances 0.000 claims description 6
- 239000005831 Quinoxyfen Substances 0.000 claims description 6
- 239000005839 Tebuconazole Substances 0.000 claims description 6
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 6
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 6
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 229960002125 enilconazole Drugs 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims description 6
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 claims description 6
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 claims description 6
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 claims description 6
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 claims description 6
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 claims description 6
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 6
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 claims description 5
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 claims description 5
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 claims description 5
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 claims description 5
- YABFPHSQTSFWQB-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(1,2,4-triazol-1-yl)-3-(trimethylsilyl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(O)(C[Si](C)(C)C)CN1C=NC=N1 YABFPHSQTSFWQB-UHFFFAOYSA-N 0.000 claims description 5
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 claims description 5
- NRTLIYOWLVMQBO-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-N-(1,1,3-trimethyl-1,3-dihydro-2-benzofuran-4-yl)pyrazole-4-carboxamide Chemical compound C=12C(C)OC(C)(C)C2=CC=CC=1NC(=O)C=1C(C)=NN(C)C=1Cl NRTLIYOWLVMQBO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 5
- 239000005747 Chlorothalonil Substances 0.000 claims description 5
- 239000005757 Cyproconazole Substances 0.000 claims description 5
- 239000005758 Cyprodinil Substances 0.000 claims description 5
- 239000005760 Difenoconazole Substances 0.000 claims description 5
- 239000005774 Fenamidone Substances 0.000 claims description 5
- 239000005777 Fenpropidin Substances 0.000 claims description 5
- 239000005780 Fluazinam Substances 0.000 claims description 5
- 239000005789 Folpet Substances 0.000 claims description 5
- 239000005800 Kresoxim-methyl Substances 0.000 claims description 5
- 239000005802 Mancozeb Substances 0.000 claims description 5
- 239000005805 Mepanipyrim Substances 0.000 claims description 5
- 239000005807 Metalaxyl Substances 0.000 claims description 5
- 239000005809 Metiram Substances 0.000 claims description 5
- 239000005810 Metrafenone Substances 0.000 claims description 5
- 239000005811 Myclobutanil Substances 0.000 claims description 5
- 239000005820 Prochloraz Substances 0.000 claims description 5
- 239000005822 Propiconazole Substances 0.000 claims description 5
- 239000005825 Prothioconazole Substances 0.000 claims description 5
- 239000005840 Tetraconazole Substances 0.000 claims description 5
- 239000005863 Zoxamide Substances 0.000 claims description 5
- UELITFHSCLAHKR-UHFFFAOYSA-N acibenzolar-S-methyl Chemical group CSC(=O)C1=CC=CC2=C1SN=N2 UELITFHSCLAHKR-UHFFFAOYSA-N 0.000 claims description 5
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 claims description 5
- VVSLYIKSEBPRSN-PELKAZGASA-N benthiavalicarb Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@@H](NC(O)=O)C(C)C)=NC2=C1 VVSLYIKSEBPRSN-PELKAZGASA-N 0.000 claims description 5
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 claims description 5
- RXDMAYSSBPYBFW-PKFCDNJMSA-N carpropamide Chemical compound N([C@@H](C)C=1C=CC(Cl)=CC=1)C(=O)[C@@]1(CC)[C@H](C)C1(Cl)Cl RXDMAYSSBPYBFW-PKFCDNJMSA-N 0.000 claims description 5
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 5
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims description 5
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 5
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 5
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 claims description 5
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 claims description 5
- VDLGAVXLJYLFDH-UHFFFAOYSA-N fenhexamid Chemical compound C=1C=C(O)C(Cl)=C(Cl)C=1NC(=O)C1(C)CCCCC1 VDLGAVXLJYLFDH-UHFFFAOYSA-N 0.000 claims description 5
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 claims description 5
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000002538 fungal effect Effects 0.000 claims description 5
- WLPCAERCXQSYLQ-UHFFFAOYSA-N isotianil Chemical compound ClC1=NSC(C(=O)NC=2C(=CC=CC=2)C#N)=C1Cl WLPCAERCXQSYLQ-UHFFFAOYSA-N 0.000 claims description 5
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- QXJKBPAVAHBARF-UHFFFAOYSA-N procymidone Chemical compound O=C1C2(C)CC2(C)C(=O)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 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
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- CKPCAYZTYMHQEX-UHFFFAOYSA-N pyrifenox Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=NOC)CC1=CC=CN=C1 CKPCAYZTYMHQEX-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([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
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
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- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000005987 sulfurization reaction Methods 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
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- 238000009736 wetting Methods 0.000 description 1
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- 241000228158 x Triticosecale Species 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
Definitions
- the present invention relates to fungicidal mixtures containing as active components
- R 1 and R 2 independently of one another cyano, nitro, halogen, Ci-C ⁇ -alkyl, Ci-C ⁇ -
- Haloalkyl methoxy, difluoromethoxy or trifluoromethoxy
- R 3 is halogen, -C 4 -alkyl or Ci-C 4 haloalkyl
- R 4 is hydrogen or halogen
- Azoles selected from bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon , Triadimol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamide, benomyl, carbendazim, thiadanazole, fuberidazole, ethaboxam, etridiazole and hymexazole
- Carboxylic acid amides selected from carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro-N- (2) cyanopheny O-isothiazole- ⁇ -carboxamide, dimethomorph, flumorph, flumetover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet, mandipropamide, N- (2- [4- [3- (4-chloro-phenyl) -prop-2-] ynyloxy] -3-methoxyphenyl) ethyl) -2-methanesulfonylamino-3-methylbutyramide, N- (2- [4-
- R 5 is methyl or ethyl
- Heterocyclic compounds selected from fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforin, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, family oxadone, fenamidone, octhilinone, probenazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1 , 5-a] pyrimidine, anilazine, diclomethine, pyroquilone, proquinazide, tricyclazole, the compound of formula IV (2-butoxy-6-iodo-3
- Z is N or CH
- Guanidines dodin, iminoctadine, guazatine,
- Antibiotics Kasugamycin, Streptomycin, Polyoxin, Validamycin A,
- Nitrophenyl derivatives binapacryl, dinocap, dinobutone, sulfur-containing heterocyclyl compounds: dithianone, isoprothiolanes,
- Organometallic compounds fentin salts such as fentin acetate,
- Inorganic active ingredients Bordeaux broth, copper acetate, copper hydroxide,
- the invention relates to a method for controlling harmful fungi with the mixture of at least one compound I and at least one of the active compounds II, the use of the compounds I and II for the preparation of such mixtures and agents and seeds containing these mixtures.
- EP-A 589 301 inter alia, some substituted Pyrazolcarbonklad-iphenyl- amides are known. However, the individual compounds disclosed are unsubstituted or merely monosubstituted in the biphenyl moiety.
- WO 01/42223 likewise discloses substituted biphenylamides which are only monosubstituted on the biphenyl radical.
- WO 2005/123689 and WO 2005/123690 disclose 2,4-disubstituted biphenylamides and 2,5-di-substituted biphenylamides are known from the earlier German application no. 102005007160.0.
- component 2 The active ingredients II mentioned above as component 2), their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hdrss.demon.co.uk/index.html); they are commercially available.
- alkyl also includes octyl, decyl, tetradecyl and hexadecyl having a cis / trans ratio of 1: 1 [CAS RN 91315-15-0];
- Spiroxamine (8-tert-butyl-1,4-dioxaspiro [4.5] dec-2-yl) diethylamine (EP-A 281 842);
- Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE-A 11 64 152);
- Mepanipyrim (4-methyl-6-prop-1-ynyl-pyrimidin-2-yl) -phenylamine (EP-A 224 339); Cyprodinil, (4-cyclopropyl-6-methylpyrimidin-2-yl) -phenylamine (EP-A 310550);
- Difenoconazole 1 - ⁇ 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl- [1,3-dioxolan-2-ylmethyl ⁇ -1 H- [1,2,4] triazole ( GB-A 2 098 607); Diniconazole, ( ⁇ E) - ⁇ - [(2,4-dichlorophenyl) methylene] - ⁇ - (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol (Noyaku Kagaku, 1983, Vol 8, p. 575);
- Ipconazole 2 - [(4-chlorophenyl) methyl] -5- (1-methylethyl) -1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (EP-A 267,778); Metconazole, 5- (4-chlorobenzyl) -2,2-dimethyl-1 - [1, 2,4] triazole-1-ylmethylcyclopentanol
- Penconazole 1- [2- (2,4-dichlorophenyl) pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12th Edition 2000, p. 712);
- Tetraconazole 1 - [2- (2,4-dichlorophenyl) -3- (1,1,2,2-tetrafluoroethoxy) propyl] -1H-1, 2,4-triazole (EP-A 234 242);
- Triflumizole (4-chloro-2-trifluoromethylphenyl) - (2-propoxy-1 - [1, 2,4] triazole-1-yl-ethylidene) -amine (JP-A 79/119 462);
- Metiram zinc ammonium ethylenebis (dithiocarbamate) (US 3,248,400); Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);
- Carbendazim (1 H-benzimidazol-2-yl) -carbamic acid methyl ester (US 3,657,443); Carboxin, 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide (US 3,249,499);
- Cyazofamido-chloro-cyano-N, N-dimethyl-S-methylphenyl-1H-imidazole-i-sulfonamide (CAS RN 120116-88-3); dazomet, 3,5-dimethyl-1,3,5; -thiadiazinane-2-thione (Bull Soc Soc. Chim. Fr. Vol. 15, p.
- Furametpyr 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88-3 ]; Isoprothiolane, diisopropyl 1, 3-dithiolan-2-ylidenemalonate (Proc. Insectic. Fungic. Conf.
- Triforines N, N '- ⁇ piperazine-1, 4-diyl-bis [(trichloromethyl) nethylenes] ⁇ diformannanide (DE-A 19 01 421);
- Nitrothal isopropyl, diisopropyl 5-nitroisophthalate Proc. Br. Insectic. Fungic. Conf.
- Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
- Fosetyl Fosetyl aluminum, ethyl phosphonate (FR 22 54 276); Iprovalicarb, [(1S) -2-methyl-1- (1-p-tolyl-ethylcarbamoyl) -propyl] -carbamic acid isopropyl ester (EP-A 472 996);
- Penthiopyrad (RS) -N- [2- (1, 3-dimethylbutyl) -3-thienyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (JP 10/130268);
- Pyraclostrobin N- ⁇ 2- [1- (4-chlorophenyl) -1H-pyrazol-3-yloxymethyl] phenyl ⁇ (N-methoxy) carbamic acid, n-methyl ester (WO 96/01256); Trifloxystrobin, methyl (E) -methoxyimino ⁇ (E) - ⁇ - [1- ( ⁇ , ⁇ , ⁇ -trifluoro-m-tolyl) ethylideneaminooxy] -o-tolyl ⁇ acetate (EP-A 460 575);
- the present invention was based on mixtures which have an improved action against harmful fungi, in particular for certain indications, with a reduced total amount of active substances applied.
- the compounds I can be used as synergists for a variety of different fungicidal agents.
- the fungicidal activity is increased to a superadditive extent.
- halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.
- C 1 -C 4 -alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl, preferably methyl or ethyl.
- Ci-C ⁇ -alkyl is a Ci-C 4 -alkyl radical as mentioned above, or for n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2- Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, preferably a C 1 -C 4 -alky
- Ci-C 4 haloalkyl is a partially or completely halogenated Ci-C 4 - alkyl group, wherein the / the halogen atom (s) is especially fluorine, chlorine and / or bromine / are eg chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, Fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2 fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl
- d-Ce-haloalkyl is a partially or completely halogenated C 1 -C 6 -alkyl radical, where the halogen atom (s) is / are in particular fluorine, chlorine and / or bromine, ie for a C 1 -C 4 -haloalkyl radical as mentioned above, or for 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, 5,5,5-trichloropentyl, undeca-fluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, 6,6,6 Trichlorohexyl or dodecafluorohexyl; preferably a C 1 -C 4 -haloalkyl radical.
- Those compounds I in which X is sulfur can be prepared, for example, by sulfurization of the corresponding compounds I in which X is oxygen (cf., for example, D. Petrova & K. Jakobcic, Croat. Chem. Acta 48, 49 (1976 ) and WO 01/42223).
- X oxygen
- those in which X is oxygen are preferred.
- R 1 and R 2 are independently cyano, fluorine, chlorine, methyl, methoxy or trifluoromethyl
- R 3 is fluorine, chlorine, methyl or Ci-haloalkyl
- R 4 is hydrogen or halogen.
- R 1 and R 2 independently of one another are cyano, fluorine, chlorine or methoxy and R 3 is fluorine, chlorine, methyl, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl and R 3 4 represent hydrogen, fluorine or chlorine.
- R 1 and R 2 independently of one another, are fluorine or chlorine
- R 3 is methyl, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl
- R 4 is hydrogen
- Table 7 Compound 7.1 - 7.20 Compounds of the formula I in which R 1 is trifluoromethyl and R 2 and R 3 are each the meanings in a row of Table A.
- Very particularly preferred compounds of the formula I are 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (2 ', 5'-difluorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl 1-H-pyrazole-4-carboxylic acid N- (2 1 , 5'-dichlorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (2 ' -fluoro-5 1 -chlorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (2'-chloro-5'-fluorobiphenyl-2-yl ) -amide, 1-methyl-3-di-fluoromethyl-1H-pyrazole-4-carboxylic acid N- (2 1 , 5 1 -difluorobiphenyl-2-yl) -amide
- mixtures of a compound of formula I with at least one active ingredient selected from the group of D) heterocyclic compounds are also preferred.
- mixtures of a compound of formula I with at least one active ingredient selected from the group of F) other fungicides are also preferred.
- active compound selected from the group of A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazo
- A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadimenol, tebu
- active substance selected from the group of A) azoles selected from epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim.
- B) strobilurins selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclobutin and trifloxystrobin.
- active compound selected from the group consisting of d) heterocyclic compounds selected from pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozoline, 5-chloro-7- (4-methylpiperidine 1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine and quinoxyfen.
- F active compound selected from the group consisting of F
- other fungicides selected from dithianon, fentin salts such as fentin acetate, fosetyl, fosetyl aluminum, phosphorous acid and salts thereof, chlorothalonil, Dichlofluanid, thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate,
- Other fungicides selected from phosphorous acid and its salts, chlorothalonil and metrafenone.
- the mixtures of compound (s) I with at least one of the active compounds II, or the simultaneous joint or separate use of at least one compound I with at least one of the active compounds II, are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. They can also be used for seed treatment.
- Alternaria species on vegetables, rapeseed, sugar beets and fruits and rice e.g. A. solani or A. alternata on potatoes and tomatoes,
- Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines, - Bremia lactucae on salad,
- Fusarium and Verticillium species on various plants e.g. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, e.g. Tomatoes,
- Gaeumanomyces graminis on cereals - Gibberella species on cereals and rice (e.g., Gibberella fujikuroi on rice),
- Mycosphaerella species on cereals, bananas and peanuts e.g. M. graminicola on wheat or M. fijiesis on bananas,
- Peronospora species on cabbage and bulbous plants e.g. P. brassicae on cabbage or P. destructor on onion,
- Phytophthora species on various plants e.g. P. capsici on paprika
- Puccinia species on various plants for example P. triticina, P. striformins, P. hordei or P. graminis on cereals or P. asparagi on asparagus, Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S. attenuatum, Entlyoma oryzae on rice , - Pyricularia grisea on grass and cereals,
- Rhynchosporium secalis on barley, rye and triticale Sclerotinia species on rape and sunflower, Septoria tritici and Stagonospora nodorum on wheat, - Erysiphe (syn. Uncinula) necator on grapevine, Setospaeria species on maize and turf, Sphacelotheca reilinia on maize, Thievaliopsis species Soybeans and cotton, Tilletia species on cereals, - Ustilago species on cereals, corn and sugar cane, eg U. maydis on corn, Venturia species (scab) on apples and pears, e.g. V. inaequalis to apple.
- the mixtures according to the invention are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
- harmful fungi Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriela spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophlum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
- Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderm spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
- the compound (s) I with at least one of the active ingredients II can be applied simultaneously, namely jointly or separately, or in succession, the sequence in the case of separate application generally having no effect on the control result.
- the pure active ingredients I to II which are further active against harmful fungi or against other pests such as insects, spiders or nematodes or herbicidal or growth-regulating agents or fertilizers can mix.
- Such mixtures of three active ingredients consist, for example, of a compound of the formula I, in particular 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (2 l , 5 1 -difluorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid-N- (2 ', 5 1 - dichlorobiphenyl-2-yl) -amide, 1-methyl-3-difluoromethyl-1 H-pyrazol-4- carboxylic acid-N- (2 ', 5 1 - difluorobiphenyl-2-yl) amide or 1-methyl-3-difluoromethyl-1 H-pyrazole-4-carboxylic acid-N- (2 1, 5'-dichlorobiphenyl-2 yl) amide, an azole from group A), in particular epoxiconazole, metconazole, triticonazole or fluquinconazole, and an insect
- mixtures of at least one compound I and at least one active ingredient II are used.
- mixtures of at least one compound I with two or, if desired, several active components can also offer particular advantages.
- Suitable further active components in the above sense are, in particular, the aforementioned active compounds II and in particular the above-mentioned preferred active compounds II.
- Compound (s) I and active compound (II) II are usually used in a weight ratio of from 100: 1 to 1: 100, preferably from 20: 1 to 1:20, in particular from 10: 1 to 1:10.
- the further active components are mixed in a ratio of from 20: 1 to 1:20 to give compound I.
- the application rates of the mixtures according to the invention at 5 g / ha to 2000 g / ha, preferably 20 to 1500 g / ha, in particular 50 to 1000 g /Ha.
- the application rates for the compound (s) I are accordingly generally 1 to 1000 g / ha, preferably 10 to 900 g / ha, in particular 20 to 750 g / ha.
- the application rates for the active compounds II are correspondingly generally 1 to 2000 g / ha, preferably 10 to 1500 g / ha, in particular 40 to 1000 g / ha.
- application rates of mixture of 1 to 1000 g per 100 kg of seed, preferably 1 to 750 g per 100 kg, in particular 5 to 500 g per 100 kg of seed are generally used.
- the method for controlling harmful fungi is carried out by the separate or combined application of compound (s) I and at least one of the active compounds II, or a mixture of compound (s) I and at least one of the active ingredients II, by spraying or dusting the seeds, the Plants or soils before or after sowing the plants or before or after emergence of the plants.
- the fungicidal synergistic mixtures according to the invention can be converted into the customary formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
- the application form depends on the respective intended use; It should in any case ensure the finest possible and uniform distribution of the mixture according to the invention.
- the formulations are prepared in a manner known per se, e.g. by stretching the active compounds with solvents and / or carriers, if desired using emulsifiers and dispersants.
- Suitable solvents / auxiliaries are essentially:
- solvents for example Solvesso ® products, xylene
- paraffins for example mineral oil fractions
- alcohols for example methanol, butanol, pentanol, benzyl alcohol
- ketones for example cyclohexanone, gamma-Butryolacton
- pyrrolidones N-methylpyrrolidone, N Octylpyrrolidone
- acetates glycols
- dimethyl fatty acid amides for fatty acids and fatty acid esters.
- solvent mixtures can also be used.
- Carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
- ground natural minerals e.g., kaolins, clays, talc, chalk
- ground synthetic minerals e.g., fumed silica, silicates
- Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
- the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene glycol octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphen
- emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water, into consideration.
- mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydrona
- Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with at least one solid carrier.
- Granules e.g. Coated, impregnated or homogeneous granules may be prepared by binding the active ingredients to at least one solid carrier.
- Solid carriers are, for example, mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
- mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertiliz
- the formulations generally contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compound (s) I and at least one of the active compounds II or of the mixture of compound (I) I with at least one of the active ingredients II.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR or HPLC spectrum).
- formulations are: 1. Products for dilution in water
- DC Dispersible Concentrates 20 parts by weight of a mixture according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidine. don, solved. Dilution in water gives a dispersion.
- the active ingredient content is 20% by weight.
- Emulsifiable Concentrates 15 parts by weight of a mixture according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
- the formulation has an active ingredient content of 15% by weight.
- a mixture according to the invention 25 parts by weight of a mixture according to the invention are dissolved in 35 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight).
- This mixture is added to 30 parts by weight of water by means of an emulsifying machine (e.g., Ultraturrax) and made into a homogeneous emulsion. Dilution in water results in an emulsion.
- the formulation has an active ingredient content of 25% by weight.
- a mixture according to the invention 20 parts by weight of a mixture according to the invention are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
- the active ingredient content in the formulation is 20% by weight.
- 50 parts by weight of a mixture according to the invention are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
- the formulation has an active ingredient content of 50% by weight.
- WP, SP Water-Dispersible and Water-Soluble Powders
- 75 parts by weight of a mixture according to the invention are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
- the active ingredient content of the formulation is 75% by weight.
- 0.5 parts by weight of a mixture according to the invention are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
- the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring.
- the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active substances.
- Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
- the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
- the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
- oils of various types wetting agents, adjuvants, herbicides, other pesticides, bactericides, if desired, also just immediately before use (tank mix), can be added. These agents are usually admixed to the mixtures according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
- adjuvants in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ® ; Alcohol alkoxylates, eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®; EO-PO block polymers, eg. B. Pluro- never RPE 2035 and Genapol ® B ®; Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
- organically modified polysiloxanes eg Break Thru S 240 ®
- Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
- EO-PO block polymers eg. B. Pluro-
- the compound (s) I and II, or the mixtures or the corresponding formulations are used by the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free of them with a fungicidally effective amount Mixture, or the compounds I and II with separate application, treated.
- the application can be made before or after the attack by the harmful fungi.
- the active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or dimethyl sulfoxide and the emulsifier Uniperol ® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent- Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. These Stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
- Uniperol ® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
- the active ingredients epoxiconazole and pyraclostrobin were used as a commercially available ready-made formulation and diluted with water to the stated active substance concentrations.
- the efficiency (W) is calculated according to the formula of Abbot as follows:
- ⁇ corresponds to the fungal infestation of the treated plants in% and ⁇ corresponds to the fungal infestation of the untreated (control) plants in%
- the infestation of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants had no infestation.
- Paprika seedlings of the cultivar "Neusiedler Ideal Elite” were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below, after 2-3 leaves had developed well.
- the treated plants were treated with a spore suspension of Botrytis cinerea containing 1.7 x 10 6 spores / ml in containing 2% aqueous biomalt solution, inoculated.
- the test plants were placed in a climatic chamber with 22 to 24 0 C, darkness and high humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.
- the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in dimethylsulfoxide.
- the stock solution was mixed according to the ratio, pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungal nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Septoria tritici.
- MTP microtiter plate
- the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. Using an absorbance photometer, the MTP's were measured at 405 nm on the 7th day after inoculation.
- the measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
Abstract
La présente invention concerne des mélanges fongicides contenant comme composés actifs 1) au moins un amide de biphényle d'acide pyrazolcarboxilique disubstitué en 2,5 de la formule (I) où X représente un oxygène ou soufre; R<SUP>1</SUP> et R<SUP>2</SUP> représentent cyano, nitro, halogène, C<SUB>1</SUB>-C<SUB>6</SUB>-alkyle, C<SUB>1</SUB>-C<SUB>6</SUB>-halogenalkyle, méthoxy, difluorométhoxy ou trifluorométhoxy; R<SUP>3</SUP> représente un halogène, C<SUB>1</SUB>-C<SUB>4</SUB>-alkyle ou C<SUB>1</SUB>-C<SUB>4</SUB>-halogenalkyle; R<SUP>4</SUP> représente un hydrogène ou halogène et 2) au moins un principe actif Il sélectionné dans les groupes A) à F): A) azole; B) strobilurine; C) amide d'acide carboxylique; D) composés hétérocycliques; E) carbamates; F) fongicides divers dans une quantité synergiquement active. L'invention concerne également un procédé de lutte contre les champignons nuisibles par des mélanges contenant au moins un composé I et au moins un principe actif II, l'utilisation des composés I avec des principes actifs Il pour produire de tels mélanges ainsi que les produits et semences contenant ces mélanges.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06763920A EP1898704A1 (fr) | 2005-06-30 | 2006-06-28 | Melanges fongicides a base d'amides de biphenyle d'acide pyrazolcarboxylique disubstitues en 2,5 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005030951 | 2005-06-30 | ||
EP06101597 | 2006-02-13 | ||
PCT/EP2006/063624 WO2007003540A1 (fr) | 2005-06-30 | 2006-06-28 | Melanges fongicides a base d'amides de biphenyle d'acide pyrazolcarboxylique disubstitues en 2,5 |
EP06763920A EP1898704A1 (fr) | 2005-06-30 | 2006-06-28 | Melanges fongicides a base d'amides de biphenyle d'acide pyrazolcarboxylique disubstitues en 2,5 |
Publications (1)
Publication Number | Publication Date |
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EP1898704A1 true EP1898704A1 (fr) | 2008-03-19 |
Family
ID=37006113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06763920A Withdrawn EP1898704A1 (fr) | 2005-06-30 | 2006-06-28 | Melanges fongicides a base d'amides de biphenyle d'acide pyrazolcarboxylique disubstitues en 2,5 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20090239748A1 (fr) |
EP (1) | EP1898704A1 (fr) |
JP (1) | JP2009500308A (fr) |
AR (1) | AR056668A1 (fr) |
BR (1) | BRPI0613576A2 (fr) |
WO (1) | WO2007003540A1 (fr) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10333373A1 (de) * | 2003-07-23 | 2005-02-10 | Bayer Ag | Fungizide Wirkstoffkombinationen |
PT1912503E (pt) * | 2005-08-05 | 2014-10-02 | Basf Se | Misturas fungicidas contendo anilidas do ácido 1-metilpirazol-4-ilcarboxílico substituídas |
WO2007110173A2 (fr) * | 2006-03-24 | 2007-10-04 | Bayer Cropscience Ag | Combinaisons de substances actives fongicides |
US8211828B2 (en) * | 2007-01-19 | 2012-07-03 | Basf Se | Fungicidal mixtures of 1-methylpyrazol-4-ylcarboxanilides and azolopyrimidinylamines |
US20100035753A1 (en) * | 2007-02-05 | 2010-02-11 | Basf Se | Fungicidal Mixtures Comprising Substituted 1-methylpyrazol-4-ylcarboxanilides |
WO2008135480A2 (fr) * | 2007-05-02 | 2008-11-13 | Basf Se | Lutte contre un pathogène fongique spécifique au soja avec du bénodanile |
EP3510869A1 (fr) | 2007-09-20 | 2019-07-17 | Bayer Cropscience LP | Combinaisons comportant une souche fongicide et un composant actif |
WO2009135860A1 (fr) | 2008-05-08 | 2009-11-12 | Basf Se | Procédé de production de carboxamides d’aryle |
CN101779656B (zh) * | 2009-12-18 | 2013-04-10 | 陕西美邦农资贸易有限公司 | 一种含氟硅唑与苯醚菌酯的杀菌组合物 |
JP5724211B2 (ja) * | 2010-04-28 | 2015-05-27 | 住友化学株式会社 | 植物病害防除組成物およびその用途 |
JP5724210B2 (ja) * | 2010-04-28 | 2015-05-27 | 住友化学株式会社 | 植物病害防除組成物およびその用途 |
JP5789918B2 (ja) * | 2010-04-28 | 2015-10-07 | 住友化学株式会社 | 植物病害防除組成物およびその用途 |
JP5724212B2 (ja) * | 2010-04-28 | 2015-05-27 | 住友化学株式会社 | 植物病害防除組成物およびその用途 |
TWI561515B (en) * | 2012-03-16 | 2016-12-11 | Viamet Pharmaceuticals Inc | Metalloenzyme inhibitor compounds |
LT3297998T (lt) | 2015-05-18 | 2020-06-10 | Viamet Pharmaceuticals (NC), Inc. | Priešgrybeliniai junginiai |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
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DE4231517A1 (de) * | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
TW384208B (en) * | 1995-09-22 | 2000-03-11 | Basf Ag | Compositions and methods for controlling harmful fungi |
ZA9811491B (en) * | 1997-12-18 | 2000-06-15 | Basf Ag | Fungicidal mixtures based on amide compounds and morpholine or piperidine derivatives. |
TW491686B (en) * | 1997-12-18 | 2002-06-21 | Basf Ag | Fungicidal mixtures based on amide compounds and tetrachloroisophthalonitrile |
TW431861B (en) * | 1997-12-18 | 2001-05-01 | Basf Ag | Fungicidal mixtures based on amide compounds and azoles |
DE19840322A1 (de) * | 1998-09-04 | 2000-03-09 | Bayer Ag | Pyrazol-carboxanilide |
EP1235811B1 (fr) * | 1999-12-09 | 2005-06-01 | Syngenta Participations AG | Pyrazolecarboxamide and pyrazolethioamide en tant que fongicide |
DE10347090A1 (de) * | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
MXPA06012071A (es) * | 2004-05-13 | 2007-01-25 | Basf Ag | Mezclas fungicidas. |
CN1968935A (zh) * | 2004-06-18 | 2007-05-23 | 巴斯福股份公司 | N-(邻苯基)-1-甲基-3-三氟甲基吡唑-4-甲酰苯胺及其作为杀真菌剂的用途 |
JP2008502636A (ja) * | 2004-06-18 | 2008-01-31 | ビーエーエスエフ アクチェンゲゼルシャフト | N−(オルト−フェニル)−1−メチル−3−ジフルオロメチルピラゾール−4−カルボキシアニリドおよびそれらの殺菌剤としての使用 |
DE102004045242A1 (de) * | 2004-09-17 | 2006-03-23 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
-
2006
- 2006-06-28 WO PCT/EP2006/063624 patent/WO2007003540A1/fr not_active Application Discontinuation
- 2006-06-28 JP JP2008518822A patent/JP2009500308A/ja not_active Withdrawn
- 2006-06-28 BR BRPI0613576A patent/BRPI0613576A2/pt not_active IP Right Cessation
- 2006-06-28 EP EP06763920A patent/EP1898704A1/fr not_active Withdrawn
- 2006-06-28 US US11/922,567 patent/US20090239748A1/en not_active Abandoned
- 2006-06-29 AR ARP060102813A patent/AR056668A1/es not_active Application Discontinuation
Non-Patent Citations (1)
Title |
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See references of WO2007003540A1 * |
Also Published As
Publication number | Publication date |
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BRPI0613576A2 (pt) | 2016-11-16 |
JP2009500308A (ja) | 2009-01-08 |
US20090239748A1 (en) | 2009-09-24 |
AR056668A1 (es) | 2007-10-17 |
WO2007003540A1 (fr) | 2007-01-11 |
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