WO2016079043A1 - Compositions pesticides comprenant un composé triazole - Google Patents
Compositions pesticides comprenant un composé triazole Download PDFInfo
- Publication number
- WO2016079043A1 WO2016079043A1 PCT/EP2015/076663 EP2015076663W WO2016079043A1 WO 2016079043 A1 WO2016079043 A1 WO 2016079043A1 EP 2015076663 W EP2015076663 W EP 2015076663W WO 2016079043 A1 WO2016079043 A1 WO 2016079043A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phenyl
- trifluoromethyl
- chloro
- compound
- component
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 168
- 230000000361 pesticidal effect Effects 0.000 title claims abstract description 16
- -1 triazole compound Chemical class 0.000 title claims description 57
- 238000000034 method Methods 0.000 claims abstract description 9
- 241000233866 Fungi Species 0.000 claims abstract description 7
- 241000238631 Hexapoda Species 0.000 claims abstract description 5
- 241000244206 Nematoda Species 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 265
- 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 127
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 117
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 claims description 116
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 claims description 94
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 claims description 92
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 claims description 90
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 81
- 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 claims description 72
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 claims description 62
- 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 description 62
- 230000000749 insecticidal effect Effects 0.000 claims description 46
- 230000000855 fungicidal effect Effects 0.000 claims description 42
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 41
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 claims description 39
- 150000001204 N-oxides Chemical class 0.000 claims description 39
- 239000004480 active ingredient Substances 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 37
- 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 33
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 claims description 23
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 23
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims description 18
- 239000005951 Methiocarb Substances 0.000 claims description 17
- 239000005934 Sulfoxaflor Substances 0.000 claims description 17
- 239000005939 Tefluthrin Substances 0.000 claims description 17
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 17
- YFBPRJGDJKVWAH-UHFFFAOYSA-N methiocarb Chemical compound CNC(=O)OC1=CC(C)=C(SC)C(C)=C1 YFBPRJGDJKVWAH-UHFFFAOYSA-N 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 claims description 16
- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 claims description 16
- 239000005746 Carboxin Substances 0.000 claims description 15
- 239000005842 Thiophanate-methyl Substances 0.000 claims description 15
- 239000005843 Thiram Substances 0.000 claims description 15
- 239000005870 Ziram Substances 0.000 claims description 15
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 claims description 15
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 claims description 15
- 229960002447 thiram Drugs 0.000 claims description 15
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 claims description 15
- 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 14
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 claims description 14
- 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 14
- 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 14
- LHZOTJOOBRODLL-UHFFFAOYSA-N 4-oxo-1-(pyrimidin-5-ylmethyl)-3-[3-(trifluoromethyl)phenyl]pyrido[1,2-a]pyrimidin-5-ium-2-olate Chemical compound O=C1[N+]2=CC=CC=C2N(CC=2C=NC=NC=2)C([O-])=C1C1=CC=CC(C(F)(F)F)=C1 LHZOTJOOBRODLL-UHFFFAOYSA-N 0.000 claims description 14
- 239000005875 Acetamiprid Substances 0.000 claims description 14
- 239000005787 Flutriafol Substances 0.000 claims description 14
- 239000006013 carbendazim Substances 0.000 claims description 14
- 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 14
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 claims description 14
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims description 14
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims description 13
- 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 13
- 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 13
- 239000005877 Alpha-Cypermethrin Substances 0.000 claims description 13
- 239000005757 Cyproconazole Substances 0.000 claims description 13
- 239000005760 Difenoconazole Substances 0.000 claims description 13
- 239000005902 Flupyradifurone Substances 0.000 claims description 13
- 239000005785 Fluquinconazole Substances 0.000 claims description 13
- 239000005796 Ipconazole Substances 0.000 claims description 13
- 239000005820 Prochloraz Substances 0.000 claims description 13
- 239000005825 Prothioconazole Substances 0.000 claims description 13
- 239000005839 Tebuconazole Substances 0.000 claims description 13
- 239000005940 Thiacloprid Substances 0.000 claims description 13
- 239000005846 Triadimenol Substances 0.000 claims description 13
- 239000005859 Triticonazole Substances 0.000 claims description 13
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 claims description 13
- QOIYTRGFOFZNKF-UHFFFAOYSA-N flupyradifurone Chemical compound C=1C(=O)OCC=1N(CC(F)F)CC1=CC=C(Cl)N=C1 QOIYTRGFOFZNKF-UHFFFAOYSA-N 0.000 claims description 13
- 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 13
- 239000004308 thiabendazole Substances 0.000 claims description 13
- 235000010296 thiabendazole Nutrition 0.000 claims description 13
- 229960004546 thiabendazole Drugs 0.000 claims description 13
- 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 claims description 13
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 claims description 12
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 12
- 239000005874 Bifenthrin Substances 0.000 claims description 12
- 239000005740 Boscalid Substances 0.000 claims description 12
- 239000005888 Clothianidin Substances 0.000 claims description 12
- 239000005946 Cypermethrin Substances 0.000 claims description 12
- 239000005761 Dimethomorph Substances 0.000 claims description 12
- 239000005780 Fluazinam Substances 0.000 claims description 12
- 239000005906 Imidacloprid Substances 0.000 claims description 12
- 239000005807 Metalaxyl Substances 0.000 claims description 12
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 claims description 12
- 239000005941 Thiamethoxam Substances 0.000 claims description 12
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims description 12
- 229940118790 boscalid Drugs 0.000 claims description 12
- 229960005424 cypermethrin Drugs 0.000 claims description 12
- 229940056881 imidacloprid Drugs 0.000 claims description 12
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 claims description 12
- IAQLCKZJGNTRDO-UHFFFAOYSA-N 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-UHFFFAOYSA-N 0.000 claims description 11
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 claims description 11
- 239000005660 Abamectin Substances 0.000 claims description 11
- 239000005788 Fluxapyroxad Substances 0.000 claims description 11
- 239000005808 Metalaxyl-M Substances 0.000 claims description 11
- 239000005812 Oxathiapiprolin Substances 0.000 claims description 11
- 239000005816 Penthiopyrad Substances 0.000 claims description 11
- 239000005860 Valifenalate Substances 0.000 claims description 11
- 229950008167 abamectin Drugs 0.000 claims description 11
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 claims description 11
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 claims description 11
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims description 10
- GOFJDXZZHFNFLV-UHFFFAOYSA-N 5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C GOFJDXZZHFNFLV-UHFFFAOYSA-N 0.000 claims description 10
- 239000005730 Azoxystrobin Substances 0.000 claims description 10
- 239000005899 Fipronil Substances 0.000 claims description 10
- 239000005783 Fluopyram Substances 0.000 claims description 10
- XQJQCBDIXRIYRP-UHFFFAOYSA-N N-{2-[1,1'-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-1pyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1C(C2CC2)C1 XQJQCBDIXRIYRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000005815 Penflufen Substances 0.000 claims description 10
- 239000005818 Picoxystrobin Substances 0.000 claims description 10
- 239000005869 Pyraclostrobin Substances 0.000 claims description 10
- 239000005834 Sedaxane Substances 0.000 claims description 10
- 239000005857 Trifloxystrobin Substances 0.000 claims description 10
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 claims description 10
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 claims description 10
- 229940013764 fipronil Drugs 0.000 claims description 10
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 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 claims description 10
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims description 9
- 239000005930 Spinosad Substances 0.000 claims description 9
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- 230000009471 action Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
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- 230000007704 transition Effects 0.000 description 2
- JERZEQUMJNCPRJ-KRWDZBQOSA-N (R)-mefentrifluconazole Chemical compound C([C@@](O)(C)C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)C(F)(F)F)N1C=NC=N1 JERZEQUMJNCPRJ-KRWDZBQOSA-N 0.000 description 1
- JERZEQUMJNCPRJ-QGZVFWFLSA-N (S)-mefentrifluconazole Chemical compound C([C@](O)(C)C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)C(F)(F)F)N1C=NC=N1 JERZEQUMJNCPRJ-QGZVFWFLSA-N 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- 239000005835 Silthiofam Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 235000010233 benzoic acid Nutrition 0.000 description 1
- YXXPNGIZHZHBTQ-UHFFFAOYSA-N butan-2-ol Chemical compound CC[C](C)O YXXPNGIZHZHBTQ-UHFFFAOYSA-N 0.000 description 1
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- 238000003197 gene knockdown Methods 0.000 description 1
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- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- CLIDMUTWHLMPMN-UHFFFAOYSA-N imidazole-1-carboxamide Chemical compound NC(=O)N1C=CN=C1 CLIDMUTWHLMPMN-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- BQIMPDXPGLLFGZ-UHFFFAOYSA-N methyl 2-[2-[6-(4-cyanohepta-1,3,5-trien-3-yloxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1OC1=CC(OC(C=C)=C(C=CC)C#N)=NC=N1 BQIMPDXPGLLFGZ-UHFFFAOYSA-N 0.000 description 1
- IBSNKSODLGJUMQ-UHFFFAOYSA-N methyl 3-methoxy-2-[2-[[6-(trifluoromethyl)pyridin-2-yl]oxymethyl]phenyl]prop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Definitions
- Pesticidal compositions comprising a triazole compound
- the present invention relates to pesticidal compositions and uses and methods for combatting harmful pests using the inventive compositions, such as phythopathogenic fungi and/or for the control of insects, acarids or nematodes. Furthermore, the present invention provides methods for improving the health of a plant using the inventive compositions.
- compositions which, at a reduced total amount of active compounds applied, show improved activity against important harmful fungi, in particular for certain indications. It was a further object to provide for compositions that are useful for the control of specific pathogens in specific important crops that are often susceptible to the attack of pathogens.
- the present invention relates to pesticidal compositions comprising,
- component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I- 22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31 , or the N-oxides or the agriculturally acceptable salts of each of the compounds; and 2) as component II a compound selected from the group consisting of the fungicidal compounds Azoxystrobin (F-1 ), Trifloxystrobin (F-2), Picoxystrobin (F-3), Pyraclostrobin (F- 4), Sedaxane (F-5), Penthiopyrad (F-6), Penflufen (F-7), Fluopyram (F-8), Fluxapyroxad (F- 9), Boscalid (F-1
- component III a compound selected from the group consisting of the fungicidal compounds Azoxystrobin (F-1 ), Trifloxystrobin (F-2), Picoxystrobin (F-3), Pyraclostrobin (F-
- the present invention relates, according to the second aspect, to compositions comprising, 1 ) as component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I- 22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31 , or the N-oxides or the agriculturally acceptable salts of each of the compounds; and
- component III a compound selected from the group consisting of the fungicidal compounds Azoxystrobin (F-1 ), Trifloxystrobin (F-2), Picoxystrobin (F-3), Pyraclostrobin (F- 4), Sedaxane (F-5), Penthiopyrad (F-6), Penflufen (F-7), Fluopyram (F-8), Fluxapyroxad (F- 9), Boscalid (F-10), Oxathiapiprolin (F-1 1 ), Metalaxyl (F-12), Metalaxyl-M (F-13), Ethaboxam (F-14), dimethomorph (F-15), Valifenalate(F-16), Cyproconazole (F-17), Difenoconazole (F- 18), Prothioconazole (F-19), Flutriafol (F-20), Thiabendazole (F-21 ), Ipconazole (F-22), Tebuconazole (F-23), Triadimenol (F-24), Tri
- compositions comprising, 1 ) as component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I- 22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31 , or the N-oxides orthe agriculturally acceptable salts of each of the compounds; and
- component III a compound selected from the group consisting of the insecticidal compounds Fipronil (ln-1 ), 3-[benzoyl(methyl)amino]-N-[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide (ln-2), 3-
- the present invention relates to to pesticidal compositions comprising,
- component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I- 22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31 , or the N-oxides or the agriculturally acceptable salts of each of the compounds; and
- the present invention relates to to pesticidal compositions comprising,
- component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I- 22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31 , or the N-oxides or the agriculturally acceptable salts of each of the compounds; and
- insecticidal compound selected from the group consisting of (ln-10), (ln-1 1 ), (ln-12), (ln-13) and (ln-14), or the N-oxides or the agriculturally acceptable salts thereof.
- the present invention relates to pesticidal compositions comprising,
- component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I- 22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31 , or the N-oxides or the agriculturally acceptable salts of each of the compounds; and
- component III a compound selected from the group consisting of the fungicidal compounds (F-1 ), (F-2), (F-3), (F-4), (F-5), (F-6), (F-7), (F-8), (F-9), (F-10), (F-1 1 ), (F-12), (F- 13), (F-14), (F-15), (F-16), (F-17), (F-18), (F-19), (F-20), (F-21 ), (F-22), (F-23), (F-24), (F-25), (F-26), (F-27), (F-28), (F-29), (F-30), (F-31 ), (F-32), (F-33) and (F-34).
- the present invention relates to pesticidal compositions comprising,
- component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I- 22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31 , or the N-oxides or the agriculturally acceptable salts of each of the compounds; and
- component III a compound selected from the group consisting of the insecticidal compounds (ln-1 ), (ln-10), (ln-1 1 ), (ln-12), (ln-13), (ln-14), (ln-15), (ln-16), (ln-17), (ln-18), (ln-19), (ln-20), (ln-21 ), (ln-22), (ln-23), (ln-24), (ln-25), (ln-26), (ln-27), (ln-28), (ln-29), (In- 30), (ln-31 ), (ln-32), (ln-33), (ln-34) and (ln-35).
- insecticidal compounds (ln-1 ), (ln-10), (ln-1 1 ), (ln-12), (ln-13), (ln-14), (ln-15), (ln-16), (ln-17), (ln-18), (ln-19), (ln-20), (ln-21 ), (ln-22), (ln-23
- the components I, II and III used in the inventive compositions are further detailed and preferences and embodiments are outlined. Any of the embodiments and preferences given for a particular component can also be combined with any of the embdiments and preferences given for one or more further component/s of the inventive compositions.
- the components I can be obtained by various routes in analogy to prior art processes known (cf. J.Agric. Food Chem. (2009) 57, 4854-4860; EP 0 275 955 A1 ; DE 40 03 180 A1 ; EP 0 1 13 640 A2; EP 0 126 430 A2).
- Compounds 1-1 to 1-31 used as component I in the inventive compositions are the following fungicidal compounds:
- compound 1-1 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1 ,2,4-triazol-1 -yl)pent-3-yn-2-ol; compound I-2 1-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-cyclopropyl-2-(1 ,2,4-triazol-1- yl)ethanol;
- compound I-4 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1 ,2,4- triazol-1 -yl)ethanol; compound 1-5 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-
- compound I-8 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-cyclopropyl-2-methoxy-ethyl]- 1 ,2,4-triazole;
- compound 1-1 1 1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-cyclopropyl-2- methoxy-ethyl]-1 ,2,4-triazole;
- compound 1-13 1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-butyl]1 ,2,4- triazole;
- compound 1-17 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1 ,2,4-triazol-1 -yl)propan-2-ol; compound 1-18 2-[2-chloro-4-(4-fluorophenoxy)phenyl]-1-(1 ,2,4-triazol-1 -yl)propan-2-ol; compound 1-19 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1 -(1 ,2,4-triazol-1-yl)butan-
- compound I-20 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-propyl]-1 ,2,4-triazole; compound 1-21 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-butyl]-1 ,2,4-triazole; compound I-22 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-pentyl]-1 ,2,4-triazole; compound I-23 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 ,1 ,1 -trifluoro-3-(1 ,2,4-triazol-1 - yl)propan-2-ol;
- compound I-25 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1 ,2,4-triazol-1 -yl)pent-4-yn-2-ol; compound I-26 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 -methoxy-3-(1 ,2,4-triazol-1 - yl)propan-2-ol;
- compound I-28 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1- yl)pentan-2-ol; compound 1-29 2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1- yl)propan-2-ol;
- Compounds 1-1 to 1-31 comprise chiral centers and they are generally obtained in the form of racemates.
- the R- and S- enantiomers of the compounds contained as component I in the compositions according to the invention can be separated and isolated in pure form with methods known by the skilled person, e.g. by using chiral HPLC. Suitable for use in the compositions are both the enantiomers and compositions thereof.
- said components I can be present in different crystal modifications, which may differ in biological activity.
- a racemic composition of the respective components I namely of compound 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 or 1-31 , respectively, is present.
- the (R)-enantiomer of compound I-3 is (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1- yl)propan-2-ol;
- the S-enantiomer of I-3 is (S)-2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol. This applies to the other compounds accordingly.
- the respective compound 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I-22, I-23, I-24, I-25, I- 26, I-27, I-28, I-29, I-30 or 1-31 , respectively, is provided and used as (R)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- an enantiomeric excess e.e.
- the respective compound 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 or 1-31 , respectively, is provided and used as (S)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
- an enantiomeric excess e.e.
- component I is compound 1-1 .
- component I is compound I-2.
- component I is compound I-3.
- component I is compound I-4.
- component I is compound I-5.
- o he nvention componen I is compound 1-6.
- o he nvention componen I is compound 1-7.
- o he nvention componen I is compound 1-8.
- o he nvention componen I is compound 1-9.
- o he nvention componen I is compound 1-10.
- o he nvention componen I is compound 1-1 1.
- o he nvention componen I is compound 1-12.
- o he nvention componen I is compound 1-13.
- o he nvention componen I is compound 1-14.
- o he nvention componen I is compound 1-15.
- o he nvention componen I is compound 1-16.
- component is compound I- 17.
- o he nvention componen I is compound 1-18.
- o he nvention componen I is compound 1-19.
- o he nvention componen I is compound I-20.
- o he nvention componen I is compound 1-21.
- o he nvention componen I is compound I-22.
- o he nvention componen I is compound I-23.
- o he nvention componen I is compound I-24.
- o he nvention componen I is compound I-25.
- o he nvention componen I is compound I-26.
- o he nvention componen I is compound I-27.
- o he nvention componen I is compound I-28.
- o he nvention componen I is compound I-29.
- o he nvention componen I is compound I-30.
- o he nvention componen I is compound 1-31.
- component I is selected from compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-1 1 , 1-13, 1-14, 1-15 and 1-16. According to a more particular embodiment of the present invention, component I is selected from compounds 1-1 , I-2, I-6 and I-8. According to another more particular embodiment of the present invention, component I is selected from compounds I-3, I-4, I-5, I-7, I-9, 1-1 1 , 1-13, I- 14, 1-15 and 1-16. According to still a further embodiment of the present invention, component I is selected from compounds 1-1 , I-2, I-3, I-4, I-5 and 1-13. According to still a further embodiment of the present invention, component I is selected from compounds 1-1 , I-4 and I- 13. According to still a further embodiment of the present invention, component I is selected from compounds I-3 and I-5.
- component I is selected from compounds 1-17, 1-18, 1-19, I-20, 1-21 , I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31.
- pesticides II and III of chemical nature described by their common names, their preparation and their biological activity e. g. against harmful fungi, pests or weed is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available and known, for example, from the references below:
- azoxystrobin methyl 2- ⁇ 2-[6-(2-cyano-1 -vinylpenta-1 ,3-dienyloxy)pyrimidin-4-yloxy]phenyl ⁇ -3- methoxyacrylate (EP 382 375); trifloxystrobin, methyl (E)-methoxyimino- ⁇ (E)-a-[1-(a,a,a- trifluoro-m-tolyl)ethylideneaminooxy]-o-tolyl ⁇ acetate (EP 460 575); picoxystrobin, methyl 3- methoxy-2-[2-(6-trifluoromethylpyridin-2-yloxymethyl)phenyl]acrylate (EP 278 595); pyraclo- strobin, methyl /V-[2-[1-(4-chlorophenyl)-1 H-pyrazol-3-yloxymethyl]phenyl ⁇ (/V-methoxy)carba- mate (WO 96/01256);
- the compounds used in the compositions of the present invention may be capable of forming salts or adducts with inorganic or organic acids or with metal ions, in particular salts with inorganic acids or N-oxides. Also the use of said compounds as salt and/or N-oxide in the inventive compositions is encompassed by the present invention.
- inorganic acids examples include hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
- Suitable organic acids are, for example, formic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid and other arylcarboxylic acids, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals with 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naph
- Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, and also of the elements of transition groups one to eight, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc, and others.
- N-oxide includes any compound used in the compositions of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N- oxide moiety.
- N-oxides of compounds of the present invention can in particular be prepared by oxidizing a ring nitrogen atom(s) of a heterocyclic ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides. The person skilled in the art knows if and in which positions N-oxides may be formed.
- each row corresponds to one embodiment of the compositions according to the invention, i.e. one specifically individualized composition with the name of the respective composition given in the first column of the respective row in the table (e.g. T1 -3).
- said compositions are ternary compositions, containing onle these three components given in the respective row of the table as active compounds.
- every combination of the compositions individualized in the tables represent embodiments of the present invention.
- compositions comprising,
- component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I- 22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and 1-31 ; and
- components II and III compounds independently selected from the group consisting of the fungicidal compounds (F-1 ), (F-2), (F-3), (F-4), (F-5), (F-6), (F-7), (F-8), (F- 9), (F-10), (F-1 1 ), (F-12), (F-13), (F-14), (F-15), (F-16), (F-17), (F-18), (F-19), Flutriafol (F- 20), (F-21 ), (F-22), (F-23), (F-24), (F-25), (F-26), (F-27), (F-28), (F-29), (F-30), (F-31 ), (F-32), (F-33) and (F-34), (wherein components II and III are different active ingredients.
- component II is selected from the fungicidal compounds Azoxystrobin (F-1 ), Trifloxystrobin (F-2), Picoxystrobin (F-3) and Pyraclostrobin (F-4), and component III is selected from from the fungicidal compounds Sedaxane (F-5), Penthiopyrad (F-6), Penflufen (F-7), Fluopyram (F-8), Fluxapyroxad (F-9), Boscalid (F-10), Oxathiapiprolin (F-1 1 ), Metalaxyl (F-12), Metalaxyl-M (F-13), Ethaboxam (F-14), dimethomorph (F-15), Valifenalate(F-16), Cyproconazole (F-17), Difenoconazole (F-18), Prothioconazole (F-19), Flutriafol (F-20), Thiabendazole (F-21 ), Ipconazole (F-22), Tebuconazole (F-23), Triadadax
- component II is (F-1) and component III is selected from from the fungicidal compounds (F-5), (F-11), (F-12), (F-13), (F-15) and (F- 21).
- component II is (F-4), and
- component III is selected from from the fungicidal compounds (F-5), (F-7), (F-8), (F-11), (F- 12), (F-13), (F-14), (F-15), (F-22), (F-27), (F-28), (F-32) and (F-34), more specifically component III is selected from (F-5), (F-7), (F-8), (F-11), (F-12), (F-13), (F-14), (F-15), (F-22), (F-32) and (F-34).
- any of said compositions are ternary compositions that contain components I, II and III as only active ingredients.
- compositions according to the invention are individualized.
- Table T1 Three-component compositions comprising one component I ("I"), one component II (“II”) and one component III ("III"), in particular ternary compositions containing the respective components I, II and III as only active ingredients.
- component II is selected from the fungicidal compounds Sedaxane (F-5), Penthiopyrad (F-6), Penflufen (F-7), Fluopyram (F-8), Fluxapyroxad (F-9) and Boscalid (F-10), and component III is selected from the fungicidal compounds
- Triticonazole F-27
- Fludioxinil F-28
- Carboxin F-29
- Silthiofarm F-30
- Ziram F-31
- Thiram F-32
- Carbendazim F-33
- Thiophanate-methyl F-34
- component II is (F-8), and component III is selected from the fungicidal compounds (F-12), (F-13), (F-15), (F-19), (F-22), (F-27) and (F-34).
- component II is Fluxapyroxad (F-9) and
- component III is selected from the fungicidal compounds (F-1 1 ), (F-12), (F-13), (F-14), (F- 15), (F-21 ), (F-22), (F-26), (F-27), (F-28), (F-30), (F-32) and (F-34), in particular, component III is selected from (F-1 1 ), (F-12), (F-13), (F-14), (F-15), (F-21 ), (F-22), (F-26), (F-30), (F-32) and (F-34).
- component II is Boscalid (F-10) and component III is selected from the fungicidal compounds (F-1 1 ), (F-12), (F-13), (F-14), (F-15), (F-21 ), (F- 22), (F-26), (F-27), (F-28), (F-30), (F-32) and (F-34).
- Table T2 Three-component compositions comprising one component I ("I"), one component II (“II”) and one component III ("III"), in particular ternary compositions containing the respective components I, II and III as only active ingredients.
- component II is selected from the fungicidal compounds Oxathiapiprolin (F-1 1 ), Metalaxyl (F-12), Metalaxyl-M (F-13), Ethaboxam (F-14), dimethomorph (F-15) and Valifenalate(F-16), and component III is selected from the fungicidal compounds Cyproconazole (F-17), Difenoconazole (F-18), Prothioconazole (F-19), Flutriafol (F-20), Thiabendazole (F-21 ), Ipconazole (F-22), Tebuconazole (F-23), Triadimenol (F-24), Prochloraz (F-25), Fluquinconazole (F-26), Triticonazole (F-27), Fludioxinil (F-28), Carboxin (F-29), Silthiofarm (F-30), Ziram (F-31 ), Thiram (F-32), Carbendazim (F-33) and Thio
- component II is selected from the fungicidal compounds (F-12), -M (F-13), (F-14) and (F-15), and component III is selected from the fungicidal compounds (F-19), (F-22), (F-25), (F-27), (F-28), (F-32) and (F-34).
- Table T3 Three-component compositions comprising one component I ("I"), one component II (“II”) and one component III ("III"), in particular ternary compositions containing the respective components I, II and III as only active ingredients.
- T3-83 1-1 F-15 F-27 T3-122 I-3 F-1 1 F-30 T3-161 I-3 F-13 F-33
- T3-31 1 I-5 F-16 F-21 T3-317 I-5 F-16 F-27 T3-323 I-5 F-16 F-33
- component II is selected from the fungicidal compounds Cyproconazole (F-17), Difenoconazole (F-18), Prothioconazole (F-19), Flutriafol (F-20), Thiabendazole (F-21 ), Ipconazole (F-22), Tebuconazole (F-23), Triadimenol (F-24), Prochloraz (F-25), Fluquinconazole (F-26) and Triticonazole (F-27), and component III is selected from the fungicidal compounds Fludioxinil (F-28), Carboxin (F-29), Silthiofarm (F- 30), Ziram (F-31 ), Thiram (F-32), Carbendazim (F-33) and Thiophanate-methyl (F-34).
- component II is (F-19) and component III is selected from the fungicidal compounds (F-28) and (F-34), in particular component III is (F- 34).
- component II is (F-22) and component III is (F-34).
- component II is (F-23) and component III is selected from the fungicidal compounds (F-28) and (F-29), in particular (F-29).
- component II is (F-27) and component III is (F-29).
- Table T4 Three-component compositions comprising one component I ("I"), one component II (“II”) and one component III ("III"), in particular ternary compositions containing the respective components I, II and III as only active ingredients.
- T4-61 1-1 F-25 F-32 T4-100 I-3 F-20 F-29 T4-139 I-3 F-25 F-33
- T4-62 1-1 F-25 F-33 T4-101 I-3 F-20 F-30 T4-140 I-3 F-25 F-34
- component II is the fungicidal compound Fludioxinil (F-28) and component III is selected from the fungicidal compounds Carboxin (F-29),
- component II is compound (F-30) and
- component III is selected from the fungicidal compounds (F-29), (F-31 ), (F-32), (F-33) and (F-34).
- component II is (F-29)
- component III is selected from the fungicidal compounds (F-31 ), (F-32), (F-33) and (F-34).
- Table T5 Three-component compositions comprising one component I ("I"), one component II (“II”) and one component III ("III"), in particular ternary compositions containing the respective components I, II and III as only active ingredients.
- compositions comprising,
- component I a compound selected from the group consisting of the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I-
- component III a compound selected from the group consisting of the fungicidal compounds Azoxystrobin (F-1 ), Trifloxystrobin (F-2), Picoxystrobin (F-3), Pyraclostrobin (F- 4), Sedaxane (F-5), Penthiopyrad (F-6), Penflufen (F-7), Fluopyram (F-8), Fluxapyroxad (F- 9), Boscalid (F-10), Oxathiapiprolin (F-1 1 ), Metalaxyl (F-12), Metalaxyl-M (F-13), Ethaboxam (F-14), dimethomorph (F-15), Valifenalate(F-16), Cyproconazole (F-17), Difenoconazole (F- 18), Prothioconazole (F-19), Flutriafol (F-20), Thiabendazole (F-21 ), Ipconazole (F-22), Tebuconazole (F-23), Triadimenol (F-24), Tri
- Triticonazole F-27
- Fludioxinil F-28
- Carboxin F-29
- Silthiofarm F-30
- Ziram F-31
- Thiram F-32
- Carbendazim F-33
- Thiophanate-methyl F-34
- component II is selected from the insecticidal compounds (ln-1 ), (ln-15), (ln-16), (ln-17), (ln-18), (ln-19), (ln-20), (ln-21 ), (ln-22), (ln-23), (ln-24), (ln-25), (ln-26), (ln-27), (ln-28), (ln-29), (ln-30), (ln-31 ), (ln-32), (ln-33) and (ln-34); and component III is selected from the fungicidal compounds (F-1 ), (F-2), (F-3), (F-4), (F-5), (F-6), (F-7), (F-8), (F-9), (F-10), (F-1 1 ), (F-12), (F-13), (F-14), (F-15), (F-16), (F-17), (F-18), (F-19), (F-20), (F-21 ), (F-22), (F-23), (F-24), (F-25), (F-F-34); and
- component II is (ln-1 ), and component III is selected from the fungicidal compounds (F-8), (F-12), (F-13), (F-15), (F-22), (F-27), (F-28), (F-30) and (F-34).
- component II is selected from the insecticidal compounds (ln-15), (ln-16) and (ln-19); and component III is selected from the fungicidal compounds (F-8), (F-12), (F-13), (F-15), (F-22), (F-27), (F-28), (F-30) and (F- 34).
- component II is (ln-20); and component III is selected from the fungicidal compounds (F-1 ), (F-2), (F-4), (F-6), (F-8), (F- 9), (F-10), (F-12), (F-13), (F-15), (F-18), (F-19), (F-22), (F-23), (F-27), (F-28), (F-30) and (F- 34).
- component II is (ln-21 ), and component III is selected from the fungicidal compounds (F-4), (F-9), (F-10), (F-12), (F-15), (F-27) and (F-34).
- component II is selected from the insecticidal compounds (ln-29) and (ln-30); and component I II is selected from the fungicidal compounds (F-4), (F-9), (F-10), (F-15), (F-18), (F-27) and (F-34).
- Table T6 Three-component compositions comprising one component I ("I"), one component II (“II”) and one component III ("III"), in particular ternary compositions containing the respective components I, II and III as only active ingredients. compocompocompo ⁇
- T6-250 1-1 ln-21 F-12
- T6-290 1-1 ln-22 F-18
- T6-330 1-1 ln-23 F-24
- T6-280 1-1 ln-22 F-8
- T6-320 1-1 ln-23 F-14
- T6-360 1-1 ln-24 F-20
- T6-370 1-1 ln-24 F-30
- T6-410 1-1 ln-26 F-2
- T6-450 1-1 ln-27 F-8
- T6-380 1-1 ln-25 F-6
- T6-420 1-1 ln-26 F-12
- T6-460 1-1 ln-27 F-18
- T6-394 1-1 ln-25 F-20
- T6-434 1-1 ln-26 F-26
- T6-474 1-1 ln-27 F-32
- T6-404 1-1 ln-25 F-30
- T6-444 1-1 ln-27 F-2
- T6-484 1-1 ln-28 F-8
- T6-500 1-1 ln-28 F-24
- T6-540 1-1 ln-29 F-30
- T6-580 1-1 ln-31 F-2
- T6-503 1-1 ln-28 F-27
- T6-543 1-1 ln-29 F-33
- T6-583 1-1 ln-31 F-5
- T6-642 1-1 ln-32 F-30
- T6-682 1-1 ln-34 F-2
- T6-722 I-3 ln-1 F-8
- T6-880 I-3 ln-18 F-30
- T6-920 I-3 ln-20 F-2
- T6-960 I-3 ln-21 F-8
Abstract
La présente invention concerne des compositions pesticides et des utilisations et des procédés de lutte contre des animaux nuisibles à l'aide des compositions de l'invention, tels que des champignons phythopathogènes et/ou pour la lutte contre les insectes, les acariens ou les nématodes. En outre, la présente invention concerne des procédés pour améliorer la santé d'une plante à l'aide des compositions de l'invention.
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EP14193733.4 | 2014-11-18 | ||
EP14193733 | 2014-11-18 |
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WO2016079043A1 true WO2016079043A1 (fr) | 2016-05-26 |
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PCT/EP2015/076663 WO2016079043A1 (fr) | 2014-11-18 | 2015-11-16 | Compositions pesticides comprenant un composé triazole |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106035380A (zh) * | 2016-06-27 | 2016-10-26 | 中国烟草总公司郑州烟草研究院 | 含苯甲酰胺类、二硝基苯胺类杀菌剂和生防菌的菌药组合物、制剂及应用 |
US10512267B2 (en) | 2013-07-08 | 2019-12-24 | BASF Agro, B.V. | Compositions comprising a triazole compound and a biopesticide |
US10519122B2 (en) | 2013-01-09 | 2019-12-31 | BASF Agro B.V. | Process for the preparation of substituted oxiranes and triazoles |
WO2020120206A3 (fr) * | 2018-12-11 | 2020-07-23 | BASF Agro B.V. | Procédé de lutte contre un champignon phytopathogène choisi parmi des espèces de phakopsora. du soja par des compositions comprenant du méfentrifluconazole |
US11185078B2 (en) | 2016-02-09 | 2021-11-30 | Basf Se | Mixtures and compositions comprising Paenibacillus strains or metabolites thereof and other biopesticides |
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Publication number | Priority date | Publication date | Assignee | Title |
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US10519122B2 (en) | 2013-01-09 | 2019-12-31 | BASF Agro B.V. | Process for the preparation of substituted oxiranes and triazoles |
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US11185078B2 (en) | 2016-02-09 | 2021-11-30 | Basf Se | Mixtures and compositions comprising Paenibacillus strains or metabolites thereof and other biopesticides |
CN106035380A (zh) * | 2016-06-27 | 2016-10-26 | 中国烟草总公司郑州烟草研究院 | 含苯甲酰胺类、二硝基苯胺类杀菌剂和生防菌的菌药组合物、制剂及应用 |
WO2020120206A3 (fr) * | 2018-12-11 | 2020-07-23 | BASF Agro B.V. | Procédé de lutte contre un champignon phytopathogène choisi parmi des espèces de phakopsora. du soja par des compositions comprenant du méfentrifluconazole |
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