WO2012004221A2 - Anthranilsäureamide in kombination mit fungiziden - Google Patents
Anthranilsäureamide in kombination mit fungiziden Download PDFInfo
- Publication number
- WO2012004221A2 WO2012004221A2 PCT/EP2011/061213 EP2011061213W WO2012004221A2 WO 2012004221 A2 WO2012004221 A2 WO 2012004221A2 EP 2011061213 W EP2011061213 W EP 2011061213W WO 2012004221 A2 WO2012004221 A2 WO 2012004221A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- alkyl
- carboxamide
- phenyl
- spp
- Prior art date
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- 239000000417 fungicide Substances 0.000 title claims description 13
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 233
- 239000013543 active substance Substances 0.000 claims abstract description 46
- 241000233866 Fungi Species 0.000 claims abstract description 29
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 22
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 21
- 241001465754 Metazoa Species 0.000 claims abstract description 20
- -1 nitro, hydroxy Chemical group 0.000 claims description 156
- 239000004480 active ingredient Substances 0.000 claims description 133
- 239000000203 mixture Substances 0.000 claims description 89
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 79
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 75
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 229920006395 saturated elastomer Polymers 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 239000003112 inhibitor Substances 0.000 claims description 39
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 27
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 claims description 23
- 239000005799 Isopyrazam Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 230000000694 effects Effects 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 12
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229960002125 enilconazole Drugs 0.000 claims description 10
- 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 10
- 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 9
- 239000005821 Propamocarb Substances 0.000 claims description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 9
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 claims description 9
- 230000035806 respiratory chain Effects 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003905 agrochemical Substances 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 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
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 239000005730 Azoxystrobin Substances 0.000 claims description 7
- 239000005738 Bixafen Substances 0.000 claims description 7
- 239000005740 Boscalid Substances 0.000 claims description 7
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 7
- 239000004606 Fillers/Extenders Substances 0.000 claims description 7
- 239000005781 Fludioxonil Substances 0.000 claims description 7
- 239000005782 Fluopicolide Substances 0.000 claims description 7
- 239000005783 Fluopyram Substances 0.000 claims description 7
- 239000005784 Fluoxastrobin Substances 0.000 claims description 7
- 239000005785 Fluquinconazole Substances 0.000 claims description 7
- 239000005786 Flutolanil Substances 0.000 claims description 7
- 239000005788 Fluxapyroxad Substances 0.000 claims description 7
- 239000005795 Imazalil Substances 0.000 claims description 7
- 239000005796 Ipconazole Substances 0.000 claims description 7
- 239000005802 Mancozeb Substances 0.000 claims description 7
- 239000005807 Metalaxyl Substances 0.000 claims description 7
- 239000005814 Pencycuron Substances 0.000 claims description 7
- 239000005820 Prochloraz Substances 0.000 claims description 7
- 239000005825 Prothioconazole Substances 0.000 claims description 7
- 239000005837 Spiroxamine Substances 0.000 claims description 7
- 239000005839 Tebuconazole Substances 0.000 claims description 7
- 239000005857 Trifloxystrobin Substances 0.000 claims description 7
- 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 7
- LDLMOOXUCMHBMZ-UHFFFAOYSA-N bixafen Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=C(F)C=C1C1=CC=C(Cl)C(Cl)=C1 LDLMOOXUCMHBMZ-UHFFFAOYSA-N 0.000 claims description 7
- 229940118790 boscalid Drugs 0.000 claims description 7
- 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 7
- 239000006013 carbendazim Substances 0.000 claims description 7
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 claims description 7
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 0.000 claims description 7
- 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 7
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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 7
- 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 7
- 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 7
- HIIRDDUVRXCDBN-OBGWFSINSA-N metominostrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1OC1=CC=CC=C1 HIIRDDUVRXCDBN-OBGWFSINSA-N 0.000 claims description 7
- JHIPUJPTQJYEQK-ZLHHXESBSA-N orysastrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1CO\N=C(/C)\C(=N\OC)\C(\C)=N\OC JHIPUJPTQJYEQK-ZLHHXESBSA-N 0.000 claims description 7
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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 6
- 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 6
- 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 6
- PQPYGYHIBMHXPC-UHFFFAOYSA-N 1,3-dichloro-1,3-bis(2,4,6-trichlorophenyl)urea Chemical compound ClC=1C=C(Cl)C=C(Cl)C=1N(Cl)C(=O)N(Cl)C1=C(Cl)C=C(Cl)C=C1Cl PQPYGYHIBMHXPC-UHFFFAOYSA-N 0.000 claims description 6
- 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 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
- 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 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
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
- 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 6
- 239000005736 Benthiavalicarb Substances 0.000 claims description 6
- 239000005747 Chlorothalonil Substances 0.000 claims description 6
- 239000005756 Cymoxanil Substances 0.000 claims description 6
- 239000005757 Cyproconazole Substances 0.000 claims description 6
- 239000005758 Cyprodinil Substances 0.000 claims description 6
- 239000005760 Difenoconazole Substances 0.000 claims description 6
- 239000005762 Dimoxystrobin Substances 0.000 claims description 6
- 239000005767 Epoxiconazole Substances 0.000 claims description 6
- 239000005774 Fenamidone Substances 0.000 claims description 6
- 239000005780 Fluazinam Substances 0.000 claims description 6
- 239000005787 Flutriafol Substances 0.000 claims description 6
- 239000005868 Metconazole Substances 0.000 claims description 6
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims description 6
- 239000005810 Metrafenone Substances 0.000 claims description 6
- 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 6
- 239000005815 Penflufen Substances 0.000 claims description 6
- 239000005816 Penthiopyrad Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 239000005818 Picoxystrobin Substances 0.000 claims description 6
- 239000005822 Propiconazole Substances 0.000 claims description 6
- 239000005823 Propineb Substances 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
- 239000005834 Sedaxane Substances 0.000 claims description 6
- 239000005840 Tetraconazole Substances 0.000 claims description 6
- 239000005842 Thiophanate-methyl Substances 0.000 claims description 6
- 239000005843 Thiram Substances 0.000 claims description 6
- 239000005845 Tolclofos-methyl Substances 0.000 claims description 6
- 239000005846 Triadimenol Substances 0.000 claims description 6
- 239000005847 Triazoxide Substances 0.000 claims description 6
- 239000005859 Triticonazole 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
- CJPQIRJHIZUAQP-MRXNPFEDSA-N benalaxyl-M Chemical compound CC=1C=CC=C(C)C=1N([C@H](C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-MRXNPFEDSA-N 0.000 claims description 6
- 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 6
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 6
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 claims description 6
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-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
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- 125000005505 thiomorpholino group Chemical group 0.000 description 1
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Classifications
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- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
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- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
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- 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
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- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N47/14—Di-thio analogues thereof
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- A—HUMAN NECESSITIES
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/32—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
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- A—HUMAN NECESSITIES
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- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
Definitions
- the present invention relates to new active compound combinations which consist of the insecticidally active compounds of the formula (I) in combination with fungicidal active compounds (II) and are very suitable for controlling undesired animal pests such as insects, acaricides and / or nematodes and undesired phytopathogenic fungi ,
- the anthranilic acid amides of the formula (I) are known in part from WO 2007/144100 and describe their insecticidal activity.
- the active ingredients mentioned in this specification with their "common name” are known, for example, from "The Pesticide Manual” 14th Ed., British Crop Protection Council 2006, and the website http://www.alanwood.net/pesticides.
- insecticidal or fungicidal activity and / or range of action and / or the plant tolerance of the known compounds, in particular to crops is not always sufficient.
- Ci-C 6 alkyl represents hydrogen, amino, hydroxy, or represents in each case optionally monosubstituted or polysubstituted by identical or different substituents, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 -cycloalkyl, where the substituents may be independently selected from halogen, cyano, nitro, hydroxy, CC 4 -alkoxy, CC 4 alkylthio, Ci-C 4 -Alkylsulfmyl, C r C 4 -Alkylsul- fonyl, (CC 4 -alkoxy) carbonyl, C -C 4 alkylamino, di- (Ci-C 4 alkyl) amino, C 3 -C 6 cycloalkyl, amino or (Ci-C 4 alkyl) C 3 -C 6 cycloalkylamino, hydrogen, CC 6 alkyl, C
- R 3 is C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylaminocarbonyl or di (C 1 -C 6) -alkylaminocarbonyl, or
- R 3 furthermore represents a singly or multiply, identically or differently substituted 5- or 6-membered aromatic or heteroaromatic ring, a 4, 5 or 6-membered partially saturated ring or saturated heterocyclic ring, or a saturated, partially saturated or aromatic heteroaromatic ring; bicyclic ring, which may optionally contain one to three heteroatoms from the series O, S or N, wherein the substituents are independently selected from SF 5; Halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, Ci-C 6 alkyl, C 3 -C 6 cycloalkyl, CC 4 -alkoxy, Coe-haloalkyl, Ci-C4-haloalkoxy, CC 4 - alkylthio, C 1 -C 4 -Alkylsulfmyl, CC 4 alkylsulfonyl, C 1 -C 4 -Alkylsulfimino, CC 4 - Alkyls
- R 2 and R 3 may be connected to each other via two to six carbon atoms and form a ring which optionally additionally contains a further nitrogen, sulfur or oxygen atom and optionally monosubstituted to fourfold with C 1 -C 2 -alkyl, C 1 -C 2 - Haloalkyl, halogen, cyano, amino Ci-C 2 alkoxy or dC 2 haloalkoxy may be substituted,
- R 4 is hydrogen, halogen, cyano, nitro CC 4 alkyl, CC 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, CC 4 alkoxy, CC 4 haloalkoxy, SF 5, CC 4 alkylthio, CC 4 - Alkylsulfmyl, CC 4 alkylsulfonyl, haloalkylthio CC 4, CC 4 -halo-alkyl-sulfmyl, CC 4 - haloalkylsulfonyl, Ci-C 4 alkylamino, di- (Ci-C 4 alkyl) amino, C 3 -C 6 cycloalkylamino, (C 1 -C4- alkoxy) imino, (Ci-C 4 alkyl) (Ci-C 4 alkoxy) imino, (CC 4
- n is 0 to 3
- QY is a 5- or 6-membered, partially saturated or saturated heterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, wherein the ring or the ring system, optionally mono- or polysubstituted, identical or different is substituted, said substituents may be independently selected from hydrogen, Ci-COE-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl , C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, cyano, carboxy, carbamoyl, nitro, hydroxy, CC 4 -alkoxy, CC 4 -
- R 9 independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkyl 4- alkylthio or C 1 -C 4 -haloalkylthio, p is 0 to 4,
- Z is N, CH, CF, CC1, CBr or Cl, the compounds of the general formula (I) furthermore comprise N-oxides and salts, and one or more fungicides of the group (II):
- Fungicides (1) inhibitors of ergosterol biosynthesis, such as Al dimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamide, fenpropidin, Fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazo
- inhibitors of respiration such as bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti- more highly enriched racemates 1RS, 4SR, 9SR, isopyrazam (anti-epimeric racemate), isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), isopyrazam (syn-epimeric racemate 1RS , 4SR, 9RS) Isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), isopyrazam (syn-epimeric enantiomer (syn-ep
- inhibitors of respiration at the complex III of the respiratory chain, such as ametoctradine, amisulbrom, azoxystrobin, cyazofamide, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, famoxadone, fenamidone, fenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin , Picoxystrobin, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, Pyribencarb, Triclopyricarb, Trifloxystrobin, (2E) -2- (2 - ⁇ [6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy ⁇ phenyl) -2- (methoxyimino) -N-methylethaneamide, (2E) -2- (methoxyimino) -N
- Mitosis and cell division inhibitors such as benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, thiophanate, zoxamide, 5-chloro-7- (4-methylpiperidine-1) yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-ajpyrimidine and 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4 - (2,4,6-trifluorophenyl) pyridazine.
- Compounds with multisite activity such as Bordeaux mixture, captafol, captan, chlorothalonil, copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dichlofluanid, dithianone, dodine, dodine free base, Ferbam, Fluorofolpet, Folpet, Guazatin, Guazatin acetate , Iminoctadine, iminoctadinal besylate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, zinc metiram, copper oxine, propamidine, propineb, sulfur and sulfur preparations such as calcium polysulfide, thiram, tolylfluanid, zineb and ziram.
- copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dichlofluanid,
- resistance inducers such as acibenzolar-S-methyl, isotianil, probenazole and tiadinil.
- inhibitors of amino acid and protein biosynthesis such as andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil and 3-
- Inhibitors of ATP production such as, for example, acetate acetate, fentin chloride, fentin hydroxide and silthiofam.
- inhibitors of cell wall synthesis such as benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamide, polyoxins, polyoxorim, validamycin A, and valifenalate.
- lipid and membrane synthesis inhibitors such as biphenyl, chloroneb, diclorane, edifenphos, etndiazole, iodocarb, ipamplesfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, quintozene, tecnazene and tolclofos-methyl.
- inhibitors of melanin biosynthesis such as carpropamide, diclocymet, fenoxanil, phthalide, pyroquilone, tricyclazole and 2,2,2-trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butane
- inhibitors of nucleic acid synthesis such as benalaxyl, benalaxyl-M (kiralaxyl), bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl and oxolic acid.
- Signal transduction inhibitors such as cholzolinate, fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen and vinclozoline.
- Decouplers such as binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap.
- the insecticidal, acaricidal, nematicidal and fungicidal activity of the active compound combinations according to the invention is substantially higher than the sum of the effects of the individual active compounds. There is an unpredictable true synergistic effect and not just an effect supplement.
- R 1 is preferably hydrogen, CC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, cyano (CC 6 -alkyl), CC 6 -alkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C r C 4 -alkoxy-Ci- C4-alkyl, Ci-C4-alkylthio-Ci-C 4 alkyl, CC 4 alkylsulfinyl-C 4- alkyl or CC 4 -alkylsulfonyl-CC 4 -alkyl,
- R 1 particularly preferably represents hydrogen, methyl, ethyl, cyclopropyl, cyanomethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl,
- R 1 very particularly preferably represents hydrogen
- R 2 is preferably hydrogen or C 1 -C 6 -alkyl.
- R 2 particularly preferably represents hydrogen or methyl.
- R 2 very particularly preferably represents hydrogen.
- R 3 preferably represents hydrogen or represents in each case optionally monosubstituted or polysubstituted by identical or different substituents, Ci-C 4 alkyl, Ci-C 4 alkoxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 - C 6 - is cycloalkyl, where the substituents can be independently selected from halogen, cyano, carboxy, carbamoyl, nitro, hydroxy, CC 4 alkyl, CC 4 haloalkyl, C 3 -C 6 cycloalkyl, CC 4 alkoxy , CC 4 haloalkoxy, CC 4 alkylthio, Ci-C 4 -Alkylsulfmyl, CC 4 - membered 6-alkylsulfonyl, Ci-C 4 alkoxycarbonyl, Ci-C4-alkylcarbonyl or a phenyl or a 4, 5 or, aromatic partially saturated or
- R 3 is preferably C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkylaminocarbonyl or C 2 - C 4 .Dialkylaminocarbonyl; or
- R 3 preferably represents a phenyl ring, a 5- or 6-membered aromatic heterocyclic ring or a 4-, 5- or 6-membered partially saturated or saturated heterocyclic ring which may contain 1-3 heteroatoms from the series N, S, O.
- the phenyl ring or heterocyclic ring is optionally mono- or polysubstituted by identical or different substituents, and where the substituents can be selected independently of one another from hydrogen, CC 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 - Alkynyl, C 3 -C 6 cycloalkyl, CC 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 halocycloalkyl, halo, cyano, carboxy, carbamoyl, NO 2 , hydroxy , CC 4 -alkoxy, CC 4 haloalkoxy, CC 4 alkylthio, Ci-C 4 -Alkylsulfmyl, CC 4 - alkylsulfonyl, CC 4 haloalkylthio, Ci-C 4 -
- R 3 particularly preferably represents hydrogen or represents in each case optionally mono- or polysubstituted, identically or differently substituted C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl, where the substituents can be selected independently of one another from halogen, cyano, carboxy, hydroxy, CC 4 alkyl, CC 4 haloalkyl, C 3 -C 6 cycloalkyl, CC 4 alkoxy, CC 4 haloalkoxy, CC 4 alkylthio, CC 4 alkylsulfmyl, CC 4 alkylsulfonyl, C 2 -C 4 alkoxycarbonyl , C 2 -C 6 - alkylcarbonyl or a phenyl ring or a 4-, 5- or 6-membered aromatic, partially saturated or saturated heterocyclic ring, wherein the phenyl ring or heterocyclic ring optionally monosubstituted or polysubstituted
- R 3 particularly preferably represents a phenyl ring, a 5- or 6-membered aromatic heterocyclic ring or a 4-, 5- or 6-membered, partially saturated or saturated heterocyclic ring which contains 1 -3 heteroatoms from the series N, S, O where the phenyl ring or heterocyclic ring is optionally mono- or polysubstituted by identical or different substituents, and where the substituents can be selected independently of one another from hydrogen, CC 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 - cycloalkyl, C r C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, cyano, carbamoyl, N0 2, Hydroxy, CC 4 alkoxy, Ci-C 4
- R 3 particularly preferably represents hydrogen, methyl, isopropyl, cyclopropyl or tert-butyl.
- R 4 particularly preferably represents chlorine, fluorine or bromine
- R 4 furthermore particularly preferably represents iodine or cyano.
- R 5 is preferably CC 4 alkyl, C 3 -C 6 cycloalkyl, CC 4 haloalkyl, dC 6 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl , C 2 -C 4 haloalkynyl, C r C 4 alkoxy, Ci-C4 haloalkoxy, alkylthio CC 4, CC 4 -Alkylsulfmyl, CC 4 alkylsulfonyl, haloalkylthio CC 4, CC -Halo- 4 alkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halogen, cyano, nitro or C 3 -C 6 -trialkylsilyl,
- R 5 particularly preferred for CC 4 alkyl, C 3 -C 6 cycloalkyl, Ci-C 4 haloalkyl, Ci-C 6 -Halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 4 haloalkenyl, C 2 C 4 alkynyl, C 2 -C 4 haloalkynyl, CC 4 alkoxy, CC 4 haloalkoxy, fluoro, chloro, bromo, iodo, cyano, nitro or C 3 -C 6 trialkylsilyl,
- R 5 very particularly preferably represents methyl, fluorine, chlorine, bromine or iodine
- R 5 particularly preferably represents methyl or chlorine
- Qx preferably represents an optionally mono- or polysubstituted by identical or different substituent R 7 substituted 5-6 membered heteroaromatic ring, which may contain 1-3 heteroatoms from the series N, O, S, or represents phenyl,
- Qx particularly preferably represents an optionally mono- or polysubstituted by identical or different substituents represented by R 7, 5- or 6-membered ring selected from the group consisting of furan, thiophene, triazole, imidazole, thiazole, oxazole, isoxazole, isothiazole, thiadiazole , Oxadiazole, pyrrole, pyridine, pyrimidine, pyridazine, pyrazine, phenyl or pyrazole,
- Qx very particularly preferably represents thiazole, oxazole, pyrrole, imidazole, triazole, pyrimidine, phenyl or pyrazole, which is represented by the group R 7
- a particularly preferably represents CH 2 , CH (CH 3 ), -CH 2 O- or -C ( O) -CH 2 -,
- Qz preferably represents a 3- to 4-membered, partially saturated or saturated, or for a 5- to 6-membered, partially saturated, saturated or aromatic ring, wherein the ring is optionally 1 -3 heteroatoms from the series N, S, 0 may contain, where the ring is optionally mono- or polysubstituted by identical or different substituents, and wherein the substituents may be independently selected from hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 - Alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, cyano, hydroxy, CC 4 - alkoxy, Ci-C4-haloalkoxy, CC 4 - alkylthio,
- Q.sup.2 is particularly preferably a 3- to 4-membered, partially saturated or saturated, or a 5-membered, partially saturated, saturated or aromatic ring, the ring optionally containing 1 -2 heteroatoms from the series N, S, O. where the ring is optionally mono- or polysubstituted by identical or different substituents, and where the substituents can be selected independently of one another from hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 - haloalkynyl, C 3 - C 6 halocycloalkyl, halogen, cyano, hydroxy, CC 4 -alkoxy, CC 4 haloalkoxy, CC 4 - alkylthio, Ci-C 4
- R 9 independently of one another are preferably hydrogen, halogen, cyano, CC 4 alkyl, CC 4 -alkoxy, C 1 -C 4 -haloalkyl, CC 4 -haloalkoxy, CC 4 -haloalkylsulfonyl or (C 1 -C 4 -alkyl) C 1 -C 4 -alkyl 4- alkoxyimino stands,
- R 9 independently of one another particularly preferably represents hydrogen, halogen, cyano or CC 4 -haloalkyl
- R 9 independently of one another very particularly preferably represents fluorine, chlorine or bromine, R 9 particularly preferably represents chlorine, p is preferably 1, 2 or 3, p is more preferably 1 or 2, p is very particularly preferably 1,
- Z is preferably N, CH, CF, CC1, CBr or CI
- Z particularly preferably represents N, CH, CF, CC1 or CBr,
- Z very particularly preferably represents N, CC1 or CH
- R 8 preferably represents linear or branched - (C 1 -C 4 -alkylene) or represents a direct bond
- R 8 particularly preferably represents methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl or iso-butyl or a direct bond
- R 8 very particularly preferably represents methyl or ethyl or a direct bond
- Q Y preferably represents a 5- or 6-membered, partially saturated or saturated heterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, where the heteroatoms can be selected from the series N, S, O, wherein the ring or the ring system is optionally mono- or polysubstituted by identical or different substituents, and wherein the substituents may be independently selected from hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - cycloalkyl, Ci-C6-haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, cyano, carboxy, carbamoyl, nitro, hydroxy, Ci-C 4 alkoxy, dC 4 hal
- Q Y particularly preferably represents an optionally mono- or polysubstituted 5- or 6-membered heteroaromatic ring of the series Q1 to Q-53 and Q-58 to Q-59, Q62 to Q63, a 9-membered aromatic heterobicyclic ring system Q-54 to Q-56 and to a 5-membered heterocyclic ring Q-60 to Q-61, wherein the substituents can be independently selected from C r C 3 alkyl, dC 3 haloalkyl, Ci-C 2 - alkoxy, halogen, cyano, hydroxy, nitro or CC 2 haloalkoxy, or wherein the substituents can be independently selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring is optionally mono- or polysubstituted, identically or differently, with Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl
- Q Y most preferably represents an optionally mono- or polysubstituted 5- or 6-membered heteroaromatic ring of the series Q-36 to Q-40, Q43, Q-58 to Q-59, Q62, Q63, an aromatic 9-membered fused heterobicyclic ring system Q-54 to Q-56 and also a 5-membered heterocyclic ring Q-60 to Q-61, where the substituents can be selected independently of one another from CC 3 -alkyl, C 1 -C 3 -haloalkyl, CC 2 - Alkoxy, halogen, cyano, hydroxy, nitro or Ci-C 2 haloalkoxy, or wherein the substituents can be independently selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring optionally mono- or polysubstituted, identical or differently, with Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -
- Q Y particularly preferred for an optionally mono- or polysubstituted or differently substituted heteroaromatic ring of the series Q-37, Q-38, Q-39, Q-40, Q43, Q-58, Q-59, Q62 and Q63, as well as for a 5-membered heterocyclic ring Q-60, where the substituents can be selected independently of one another from methyl, ethyl, cyclopropyl, tert-butyl, chlorine, fluorine, iodine, bromine, cyano, nitro, difluoromethyl, trifluoromethyl, pentafluoroethyl, n-heptafluoropropyl and isoheptafluoropropyl or where the substituents can be selected independently of one another from phenyl or a 5- or 6-membered heteroaromatic ring, where the substituents can be selected independently of one another from methyl, ethyl, cyclopropyl, tert-
- the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
- lactones and lactams are preferably also included.
- the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example at N and S, and then form, for example, the divalent groups -N (O) -, -S (O) - (also short SO) and -S (0) 2 - (also short S0 2 ) in the heterocyclic ring.
- - N (O) and -S (0) groups both enantiomers are included.
- Substituents other than the oxo group may also be bonded to a heteroatom on a heterocyclic ring, for example a nitrogen atom, if a hydrogen atom on the nitrogen atom of the main body is replaced. In the case of the nitrogen atom and other heteroatoms such.
- the sulfur atom is also a further substitution to form quaternary ammonium compounds or sulfonium compounds in question.
- the compounds of formulas (I) may be in the form of various regioisomers. For example in the form of mixtures of compounds with the definition Q62 or Q63 or in the form of mixtures of Q58 and Q59.
- the invention also includes active compound combinations comprising mixtures of compounds of the formulas (I), where Q Y has the meanings Q62 and Q63, and Q58 and Q59 and the compounds can be present in different mixing ratios, and one or more active compounds from the group (II) , While mixing ratios of from compounds of formula (I) wherein the radical Q Y is Q62 or Q58 are preferred to compounds of formula (I) wherein the radical Qy represents Q63 or Q59, from 60:40 to 99: 1, more preferably from 70:30 to 97: 3, most preferably from 80:20 to 95: 5.
- R 3 is hydrogen or each optionally mono- or polysubstituted by identical or different substituents CC 6 alkyl, CC 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 2 cycloalkyl, C 3 - Ci 2 cycloalkyl-Ci-C6-alkyl, wherein the substituents may be independently selected from halogen, amino, cyano, nitro, hydroxy, Ci-C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C4- alkoxy, Ci-C4-haloalkoxy, CC 4 -alkylthio, C 2 -C 6 alkoxycarbonyl, Ci-C6-alkylcarbonyl, C3 -C6- cycloalkylamino or a 5- or 6-membered heteroaromatic ring,
- R 4 is halogen, cyano or methyl
- R 5 is methyl or chlorine
- Z is N, CC1 or CH
- Qy represents an optionally mono- or polysubstituted 5- or 6-membered heteroaromatic ring of the series Q-36 to Q-40, Q43, Q-58 to Q-59, Q62, Q63, a 9-membered aromatic heterobicyclic ring system Q- 54 to Q-56 and also a 5-membered heterocyclic ring Q-60 to Q-61, where the substituents can be selected independently of one another from C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 2 -alkoxy, Halogen, cyano, hydroxy, nitro or CC 2 -haloalkoxy, where the compounds of the formula (1-1) may be present in the form of salts, and one or more active substances selected from the group (II),
- the compounds of formula (1 1) preferably represents hydrogen or represents in each case optionally monosubstituted or polysubstituted by identical or different substituents, Ci-C 6 alkyl, CC 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 - cycloalkyl, C 3 -C cycloalkyl-Ci-C stands 6 6 alkyl, wherein the substituents may be independently selected from halogen, cyano, amino, hydroxy, Ci-C 6 alkyl , C 1 -C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4 alkylthio, Cj-C b cycloalkyl, a 5 or 6-membered heteroaromatic ring containing 1 -2 heteroatoms from the series N, 0, S in which two oxygen atoms are not adjacent in the ring, more preferably one
- R 4 is preferably halogen, cyano or methyl
- R 4 particularly preferably represents chlorine and cyano
- R 4 is also particularly preferably bromine, fluorine, iodine or methyl
- R 5 is preferably and more preferably methyl, Z is preferably N or CH,
- QY is preferably an optionally mono- or polysubstituted or differently substituted heteroaromatic ring of the series Q-37, Q-38, Q-39, Q-40, Q43, Q-58, Q-59, Q62 and Q63, as well as a 5 -member heterocyclic ring Q-60, wherein the substituents can be independently selected from methyl, ethyl, cyclo-propyl, tert-butyl, chlorine, fluorine, iodine, bromine, cyano, nitro, difluoromethyl, trifluoromethyl, pentafluoroethyl, n Heptafuoropropyl and isoheptafluoropropyl.
- QY particularly preferably represents an optionally mono- or polysubstituted or different substituted heteroaromatic ring of the series Q-58 and Q-59, wherein the substituents can be independently selected from methyl, ethyl, cyclo-propyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, n-heptafluoropropyl and iso-heptafluoropropyl.
- the compounds of formulas (1-1) may be in the form of various regioisomers.
- the compounds of formulas (1-1) may be in the form of various regioisomers.
- the compounds of formulas (1-1) may be in the form of mixtures of compounds with the definition Q62 or Q63 or in the form of mixtures of Q58 and Q59. Therefore, according to the invention also includes combinations of active substances containing mixtures of compounds of formulas (1-1), wherein Q Y has the meanings Q62 and Q63, and Q58 and Q59 and the compounds may be present in different mixing ratios, and one or more active compounds from the group ( II).
- active ingredients containing at least one active substance of the general formula (I) or (1-1) and an active compound of the group (II) selected from
- active ingredient combinations comprising the mixtures of active compounds of the formula (I-I-1) to (I-1-60) given below and one or more active compounds of the group (II).
- mixtures are preferably present in a mixing ratio of 80:20 to 99: 1.
- Be ⁇ playfully mentioned is the mixture Il -1 / 1-1-7, wherein the compound of formula III to the compound of formula 1-1-7 in a mixing ratio of 80:20 to 99: 1 is present.
- mixture 1-1-2 / 1-1-8 mentions the mixture 1-1-2 / 1-1-8 wherein the compound of the formula 1-1-2 to the compound of the formula 1-1-8 in a mixing ratio of 80:20 to 99: 1 is present.
- -1-1- / 1-1-7
- the active ingredient combinations may also contain other fungicidal, acaricidal or insecticidal Zumischkomponenten beyond.
- the combinations according to the invention contain active compounds of the formula (I) to the mixing partner of the group (II) in the ratio of 625: 1 to 1: 625; preferably in the preferred and particularly preferred mixing ratios given in Table 1 below: • the mixing ratios are based on weight ratios.
- the ratio is to be understood as the active ingredient of the formula (I): Mixture partner to formula (I): Mischpartner
- the application rates can be varied within a relatively wide range, depending on the mode of administration.
- the application rate of the active compound combinations according to the invention is in the treatment of parts of plants, e.g.
- Leaves from 0.1 to 1000 g / ha preferably from 10 to 500 g / ha, more preferably from 50 to 300 g / ha (when applied by pouring or drop, the application rate can even be reduced, especially if inert substrates such as rock wool or perlite are used); in the seed treatment from 1 to 2000 g per 100 kg of seed, preferably from 2 to 1000 g per 100 kg of seed, more preferably from 3 to 750 g per 100 kg of seed, most preferably from 5 to 500 g per 100 kg of seed; in the soil treatment from 0.1 to 5000 g / ha, preferably from 1 to 1000 g / ha.
- the active compound combinations according to the invention can be used to protect plants within a certain period of time after the treatment against attack by phytopathogenic fungi and / or animal pests.
- the period of time within which protection is afforded generally ranges from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, most preferably from 1 to 7 days after treatment of the plants with the active - up to 200 days after seed treatment.
- the active compound combinations according to the invention are suitable for plant tolerance, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling phytopathogenic fungi such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc. and of animal pests, in particular insects, arachnids, helminths, nematodes and mollusks, used in agriculture, horticulture, livestock, forestry, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector occurrence. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
- the active compound combinations according to the invention have very good fungicidal properties and can be used for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
- the active compound combinations according to the invention are particularly suitable for controlling Phytophthora infestans, Plasmopara viticola and Botrytis cinerea.
- Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
- Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
- pathogens of fungal and bacterial diseases which fall under the generic names enumerated above, are named: Diseases caused by powdery mildews such as e.g.
- Blumeria species such as Blumeria graminis
- Podosphaera species such as Podosphaera leucotricha
- Sphaerotheca species such as Sphaerotheca fuliginea
- Uncinula species such as Uncinula necator
- Gymnosporangium species such as Gymnosporangium sabinae Hemileia species, such as Hemileia vastatrix;
- Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
- Puccinia species such as Puccinia recondita
- Uromyces species such as Uromyces appendiculatus
- Bremia species such as Bremia lactucae
- Peronospora species such as Peronospora pisi or P. brassicae;
- Phytophthora species such as Phytophthora infestans
- Plasmopara species such as Plasmopara viticola
- Pseudoperonospora species such as Pseudoperonospora humuli or
- Pythium species such as Pythium ultimum
- Alternaria species such as Alternaria solani;
- Cercospora species such as Cercospora beticola
- Cladiosporum species such as Cladiosporium cucumerinum
- Cochliobolus species such as Cochliobolus sativus
- Colletotrichum species such as Colletotrichum lindemuthanium
- Cycloconium species such as cycloconium oleaginum
- Diaporthe types such as Diaporthe citri;
- Elsinoe species such as Elsinoe fawcettii
- Gloeosporium species such as, for example, Gloeosporium laeticolor
- Glomerella species such as Glomerella cingulata
- Guignardia species such as Guignardia bidwelli;
- Leptosphaeria species such as Leptosphaeria maculans
- Magnaporthe species such as Magnaporthe grisea
- Mycosphaerella species such as Mycosphaerelle graminicola
- Phaeosphaeria species such as Phaeosphaeria nodorum
- Pyrenophora species such as, for example, Pyrenophora teres
- Ramularia species such as Ramularia collo-cygni
- Rhynchosporium species such as Rhynchosporium secalis
- Septoria species such as Septoria apii
- Typhula species such as Typhula incarnata
- Venturia species such as Venturia inaequalis
- Root and stem diseases caused by eg Corticium species, such as Corticium graminearum;
- Fusarium species such as Fusarium oxysporum
- Gaeumannomyces species such as Gaeumannomyces graminis
- Rhizoctonia species such as Rhizoctonia solani
- Tapesia species such as Tapesia acuformis
- Thielaviopsis species such as Thielaviopsis basicola
- Ear and panicle diseases caused by e.g.
- Alternaria species such as Alternaria spp .
- Aspergillus species such as Aspergillus flavus
- Cladosporium species such as Cladosporium spp .
- Claviceps species such as Claviceps purpurea
- Fusarium species such as Fusarium culmorum
- Gibberella species such as Gibberella zeae
- Monographella species such as Monographella nivalis
- Sphacelotheca species such as Sphacelotheca reiliana
- Tilletia species such as Tilletia caries
- Urocystis species such as Urocystis occulta
- Ustilago species such as Ustilago nuda
- Aspergillus species such as Aspergillus flavus
- Botrytis species such as Botrytis cinerea
- Penicillium species such as Penicillium expansum
- Sclerotinia species such as Sclerotinia sclerotiorum
- Verticilium species such as Verticilium alboatrum
- Fusarium species such as Fusarium culmorum
- Phytophthora species such as Phytophthora cactorum
- Pythium species such as Pythium ultimum
- Rhizoctonia species such as Rhizoctonia solani
- Sclerotium species such as Sclerotium rolfsii
- Nectria species such as Nectria galligena
- Monilinia species such as Monilinia laxa
- Esca species such as Phaemoniella clamydospora
- Botrytis species such as Botrytis cinerea
- Rhizoctonia species such as Rhizoctonia solani
- Xanthomonas species such as Xanthomonas campestris pv. Oryzae;
- Pseudomonas species such as Pseudomonas syringae pv. Lachrymans;
- Erwinia species such as Erwinia amylovora
- the following diseases of soybean beans can be controlled: fungal diseases on leaves, stems, pods and seeds caused by e.g.
- Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)) , Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), Powdery Mildew (Phyllosticta sojaecola) Micros
- Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wilt, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stem Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var.
- Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, Pythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
- the active compound combinations according to the invention can be used with particular success for the purpose of combating cereal diseases, such as against Puccinia species and diseases in wine, fruit and vegetable crops, such as against Botrytis, Venturia or Alternaria species use.
- the active compound combinations according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi is by no means a limitation of the detectable mycotic spectrum, but has only an explanatory character.
- the active compound combinations according to the invention also have very good insecticidal effects. They have a very broad insecticidal activity spectrum, in particular against the following animal pests:
- Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp .. From the class of the arachnids e.g.
- Acarus spp. Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri , Eutetranychus spp., Eriophyes spp., Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phylloc
- Anthrenus spp. Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., Chaetocnema spp., Cleonus mendicus, Conoderus spp.
- Lucilla spp. Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia spp., Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp., Stomoxys spp , Tabanus spp., Tannia spp., Tetanops spp., Tipula spp.
- Gastropoda From the class of Gastropoda, for example Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.
- helminths e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum , Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Ne
- protozoa such as Eimeria
- Lepidoptera From the order of Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius , Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnephasia spp., Conopomorph
- Copitarsia spp. Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp.
- Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
- siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
- Thysanoptera e.g. Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips hevens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp. From the order of Thysanura e.g. Lepisma saccharina.
- the plant parasitic nematodes include, for example, Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp ..
- the active compound combinations according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
- engineering materials to be protected from microbial alteration or destruction by the active compounds of the present invention may be adhesives, glues, paper and board, textiles, leather, wood, paints and plastics, coolants, and other materials that infiltrate or decompose microorganisms can be.
- materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms.
- technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
- microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
- the active compound combinations according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
- microorganisms of the following genera There may be mentioned, for example, microorganisms of the following genera:
- Alternaria such as Alternaria tenuis
- Aspergillus such as Aspergillus niger
- Chaetomium such as Chaetomium globosum
- Coniophora like Coniophora puetana,
- Lentinus like Lentinus tigrinus
- Penicillium such as Penicillium glaucum
- Polyporus such as Polyporus versicolor
- Aureobasidium such as Aureobasidium pullulans
- Sclerophoma such as Sclerophoma pityophila
- Trichoderma like Trichoderma viride
- Escherichia like Escherichia coli
- Pseudomonas such as Pseudomonas aeruginosa
- Staphylococcus such as Staphylococcus aureus.
- insects By way of example and preferably without limiting however, the following insects are mentioned: Beetles such as Hylotrupes b Camillus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.
- Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
- Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
- Bristle tails like Lepisma saccharina.
- Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
- the material to be protected from insect attack is wood and woodworking products.
- wood and wood products which can be protected by the active compound combinations according to the invention, is to be understood by way of example: timber, wooden beams, railway sleepers, bridge parts, boat jetties, wooden vehicles, crates, pallets, containers, telephone poles, wood cladding, wooden windows and doors, plywood, chipboard, Carpentry or wood products commonly used in home construction or joinery.
- the active compound combinations can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
- the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, and further processing aids.
- the insecticidal active ingredient combinations or concentrates used for the protection of wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.
- the amount of active ingredient combinations or concentrates used depends on the nature and occurrence of the insects and on the medium. The optimal amount used can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.
- insects in particular insects, arachnids and mites, which are used in enclosed spaces such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. They can be used to control these pests in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
- Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
- Araneae e.g. Aviculariidae, Araneidae.
- Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
- Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
- Anthrenus spp. From the order of Coleptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
- Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
- Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
- Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
- Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
- Anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
- Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
- Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprayers, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations.
- Pump and atomizer sprayers fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations.
- the active compound combinations of the invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as ticks, leather ticks, mange mites, mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces, Featherlings and fleas.
- animal parasites ectoparasites
- ticks leather ticks, mange mites, mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces, Featherlings and fleas.
- Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
- Nematocerina and Brachycerina eg Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.
- Atylotus spp. Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
- siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
- heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
- Actinedida Prostigmata
- Acaridida Acaridida
- Acarapis spp. Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
- the active compound combinations according to the invention are also suitable for controlling arthropods, the livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs , Cats, caged birds, aquarium fish and so-called experimental animals, such as hamsters, guinea pigs, rats and mice infested.
- livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs , Cats, caged birds, aquarium fish and so-called experimental animals, such as hamsters, guinea pigs, rats and mice infested.
- the application of the active compound combinations according to the invention takes place in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boluses, the feed-through process, suppositories, by parenteral Administration, for example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, dipping or bathing (dipping), spraying, pouring (pour-on and spot -on), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.
- enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boluses, the feed-through process, suppositories
- parenteral Administration for example by injection
- the active ingredient combinations When used for livestock, poultry, pets, etc., the active ingredient combinations may be used as formulations (for example, powders, emulsions, flowables) containing the active ingredients in an amount of 1 to 80% by weight, directly or after 100 to 10,000 dilution or use as a chemical bath.
- the active compound combinations according to the invention may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents ( Mycoplasma-like-organism) and RLO (Rickettsia-like-organism).
- the present invention further relates to formulations and application forms prepared therefrom as crop protection agents and / or pesticides such.
- B. drench, drip and spray comprising at least one of the active compound combinations according to the invention.
- the use forms contain other crop protection agents and / or pesticides and / or the effect of improving adjuvants such as penetration enhancers, eg.
- vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g.
- organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
- Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
- SL water-soluble liquids
- EC emulsion concentrates
- EW emulsions in water
- SC suspension concentrates
- SC SE, SE, FS, OD
- WG water-dispersible granules
- GR granules
- capsule concentrates CS
- the formulations contain in addition to one or more active substances according to the invention further agrochemical active substances.
- auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants.
- An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
- Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
- formulations are prepared in a known manner, e.g. by mixing the active ingredients with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
- excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
- the preparation of the formulations is carried out either in suitable systems or before or during use.
- excipients there may be used those substances which are suitable for conferring special properties, such as certain physical, technical and / or biological properties, to the formulation of the active substance or to the forms of use prepared from these formulations (for example usable plant protection agents such as spray or seed dressing).
- polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
- aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
- alcohols and polyols which may also be substituted, etherified and / or esterified
- ketones such as
- Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
- Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
- alcohols such as butanol or glycol and their ethers and esters
- ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
- strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
- Suitable solvents are, for example, aromatic hydrocarbons, such as, for example, xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols, such as methanol, ethanol, iso-propanol, butanol or glycol and their ethers and Esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide, and water.
- aromatic hydrocarbons such as, for example, xylene, toluene or alkylnaphthalenes
- chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene,
- Suitable carriers are, in particular: Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
- Suitable carriers for granules are: e.g.
- liquefied gaseous diluents or solvents can be used.
- Particularly suitable are those diluents or carriers which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
- Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkyl- sulfonates, alkyl sulfates, arylsulfonates, protein
- a surfactant is advantageous when one of the active ingredients and / or one of the inert carriers is not soluble in water and when applied in water.
- dyes such as inorganic pigments, eg iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients, such as salts of iron, manganese, boron, in the formulations and the applications derived therefrom, can be used. Copper, cobalt, molybdenum and zinc may be present.
- Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
- formulations and applications derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
- additional auxiliaries may be mineral and vegetable oils.
- auxiliaries may be present in the formulations and in the use forms derived therefrom.
- additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
- the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
- retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
- Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
- Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
- the method described in the literature can be used to determine this property.
- Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or Isotridecylethoxylat (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
- alcohol alkoxylates such as coconut oil ethoxylate (10) or Isotridecylethoxylat (12)
- fatty acid esters such as rapeseed oil or soybean oil
- fatty amine alkoxylates such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
- the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
- the active ingredient concentration of the use forms is in the range of 0.00000001 to 97 wt .-% of active ingredient, preferably in the range of 0.0000001 to 97 wt .-%, particularly preferably in the range of 0.000001 to 83 wt .-% or 0, 000001 to 5 wt .-% and most preferably in the range of 0.0001 to 1 wt .-%.
- the active compound combinations according to the invention can be present in their commercially available formulations and in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
- active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
- a mixture with other known active ingredients, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving the plant properties is possible.
- the active compound combinations according to the invention can furthermore be present in mixtures with synergists when used as fungicides and / or insecticides in their commercial formulations and in the forms of use prepared from these formulations.
- synergists are compounds that increase the effect of the active ingredients without the added synergist itself having to be active.
- the active compound combinations according to the invention can also be present in their commercial formulations and in the forms of use prepared from these formulations in mixtures with inhibitors which inhibit degradation of the active substance after application in the environment of the plant, on the surface of plant parts or in plant tissues.
- the application is done in a custom forms adapted to the application forms.
- plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
- Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including plant varieties that can be protected or not protected by plant variety protection rights.
- Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
- the plant parts also include crops and vegetative and generative propagation material, for example fruits, seeds, cuttings, tubers, rhizomes, offshoots, seeds, bulbs, sinkers and shoots.
- the treatment according to the invention of the plants and plant parts with the active compound combinations takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg by dipping, spraying, evaporating, atomizing, spreading, spreading painting, injecting and propagating material, in particular seed, by single or multi-layer coating.
- the active substance combinations can be prepared before the treatment by mixing the individual active ingredients. Or the treatment is carried out successively by using first a compound of formula (I) or (1-1) followed by treatment with a group II active ingredient. However, it is also possible to first treat the plants or plant parts with a group II active ingredient and to join the treatment with a compound of formula I or (1-1).
- plants which can be treated according to the invention mention may be made of the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp. (for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp.
- Rosaceae sp. for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries
- Rosaceae sp. for example, pome fruits such as apple and pear
- Rubiaceae sp. for example, coffee
- Theaceae sp. Sterculiceae sp.
- Rutaceae sp. for example, lemons, organs and grapefruit
- Solanaceae sp. for example tomatoes
- Liliaceae sp. Asteraceae sp.
- Umbelliferae sp. for example, Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. leek, onion), Papilionaceae sp.
- Main crops such as Gramineae sp. (for example corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes and rapeseed, mustard, horseradish and cress), Fabacae sp. (for example, bean, peanuts), Papilionaceae sp. (for example, soybean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example, sugar beet, fodder beet, Swiss chard, beet); Crops and ornamental plants in the garden and forest.
- Gramineae sp. for example corn, turf, cereals such as wheat, rye, rice, barley, oats, mille
- the treatment according to the invention can also lead to superadditive (“synergistic”) effects.
- the following effects are possible, which go beyond the expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active ingredients and compositions that can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to drought or water or soil salinity, increased flowering, harvest relief, ripening, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher sugar concentration in the fruits, better storage and / or processability of the harvested products.
- the active compound combinations according to the invention can also exert a strengthening effect on plants. They are therefore suitable for mobilizing the plant defense system against attack by undesirable phytopathogenic fungi and / or microorganisms and / or viruses. This may optionally be one of the reasons for the increased effectiveness of the combinations according to the invention, for example against fungi.
- Plant-strengthening (resistance-inducing) substances in the present context should also mean those substances or combinations of substances which are able to stimulate the plant defense system so that the treated plants, when subsequently inocculated with undesirable phytopathogenic fungi and / or microorganisms and / or viruses a considerable degree of resistance to these unwanted phytopathogenic fungi and / or microorganisms and / or viruses.
- phytopathogenic fungi, bacteria and viruses are understood to be undesirable phytopathogenic fungi and / or microorganisms and / or viruses.
- the substances according to the invention can therefore be employed for the protection of plants against attack by the mentioned pathogens within a certain period of time after the treatment.
- the period of time over which a protective effect is achieved generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active substances.
- Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology). Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stressors, i. H. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.
- Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties.
- An increased yield can in these plants z. B. based on improved plant physiology, improved plant growth and improved plant development, such as water efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife.
- Yield can be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, internode count and spacing, root growth, seed size, fruit size, Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping and stability.
- Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
- Plants which can be treated according to the invention are hybrid plants which already express the properties of heterosis or hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors.
- Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
- the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
- Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
- cytoplasmic male sterility have been described, for example, for Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072).
- pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
- a particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 1991/002069).
- Plants or plant varieties which can be treated according to the invention are herbicidally tolerant plants, ie plants made tolerant to one or more given herbicides. Such plants can be obtained by selection of plants containing a mutation conferring such herbicide tolerance.
- the active compound combinations according to the invention are suitable for the treatment of seed. Preference is given to mention the combinations according to the invention mentioned above as being preferred or particularly preferred.
- a large part of the damage to crops caused by phytopathogenic fungi and / or animal pests already occurs through the infestation of the seed during storage and after introduction of the seed into the soil and during and immediately after germination of the plants.
- This phase is particularly critical, as the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the entire plant.
- the control of phytopathogenic fungi and / or animal pests by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods of protecting the seed and the germinating plant, which eliminate the need for additional crop protection after sowing or after emergence of the plants.
- methods for treating seed should also include the intrinsic fungicidal and / or insecticidal properties of transgenic plants in order to achieve optimum protection of the seed and also the germinating plant with a minimum of pesticides.
- the present invention therefore also relates, in particular, to a method for protecting seed and germinating plants from infestation by phytopathogenic fungi and / or animal pests by treating the seed with a combination of active substances according to the invention.
- the method according to the invention for protecting seed and germinating plants from infestation by phytopathogenic fungi and / or animal pests comprises a method in which the seed is at the same time treated with a compound of the formula (I) and an active compound from the above-mentioned group (II ) is treated. It also comprises a process in which the seed is treated at different times with a compound of formula (I) and an active ingredient from the group (II) listed above.
- the invention also relates to the use of the active compound combinations according to the invention for the treatment of seed for the protection of the seed and the germinating plant from phytopathogenic fungi and / or by phytopathogenic fungi and / or animal pests. Furthermore, the invention relates to seed which has been treated with a combination of active substances according to the invention for protection against phytopathogenic fungi and / or animal pests. The invention also relates to seed treated at the same time with a compound of formula (I) and a group II active ingredient. The invention further relates to seed which has been treated at different times with a compound of formula (I) and a group II active ingredient.
- the individual active compounds of the active ingredient combination according to the invention may be present in different layers on the seed.
- the layers which comprise a compound of the formula (I) and an active compound from group II may optionally be separated by an intermediate layer.
- the invention also relates to seed in which a compound of formula (I) and an active compound from group II are applied as part of a coating or as a further layer or further layers in addition to a coating.
- An advantage of the present invention is the synergistic increase in the insecticidal activity of the active compound combinations according to the invention over the insecticidal single active substance, which goes beyond the expected efficacy of the two individually applied active ingredients. Also advantageous is the synergistic increase in the fungicidal activity of the active compound combinations according to the invention compared with the fungicidal single active substance, which goes beyond the expected effectiveness of the individually applied active ingredient. This allows optimization of the amount of active ingredients used. Likewise, it is considered to be advantageous that the active compound combinations according to the invention can be used in particular also in transgenic seed.
- the active compound combinations according to the invention are suitable for the protection of seed of any plant variety as already mentioned above, which is used in agriculture, in the greenhouse, in forests or in horticulture.
- these are corn, peanut, canola, rapeseed, poppy, soybean, cotton, turnip (eg sugarbeet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables ( eg tomatoes, cabbages, Salad, etc.).
- the active compound combinations according to the invention are likewise suitable for the treatment of the seed of fruit plants and vegetables as already mentioned above.
- the active ingredient combination according to the invention is applied to the seed alone or in a suitable formulation.
- the seed is treated in a state where it is so stable that no damage occurs during the treatment.
- the treatment of the seed can be done at any time between harvesting and sowing.
- seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
- seed may be used which has been harvested, cleaned and dried to a moisture content below 15% by weight.
- seed can also be used, which after drying, for example, treated with water and then dried again.
- the amount of the active ingredient combination and / or other additives applied to the seed is chosen so that germination of the seed is not impaired or the resulting plant is not damaged. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.
- the agents according to the invention can be applied directly, ie without containing further components and without being diluted. In general, it is preferable to apply the agents to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 AI, WO 2002/080675 AI, WO 2002/028186 A2.
- the active compounds which can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
- formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
- conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
- Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. There are both in Water sparingly soluble pigments as well as water-soluble dyes usable. Examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1.
- Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preference is given to using alkylnaphthalene sulfonates, such as diisopropyl or diisobutylnaphthalene sulfonates.
- Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
- Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
- Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
- Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
- Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
- Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
- Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
- Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
- polyvinylpyrrolidone polyvinyl acetate, polyvinyl alcohol and Tylose.
- the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, p. 401-412).
- the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds, including seed of transgenic plants. In this case, additional synergistic effects may occur in interaction with the substances formed by expression.
- the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water
- all mixing devices customarily usable for the dressing can be considered.
- the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed.
- a drying process follows.
- the active compound combinations according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
- the active compound combinations according to the invention also have a strong tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against attack by unwanted microorganisms.
- plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.
- Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
- the substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens.
- the period within which protection is provided generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
- the listed plants can be treated particularly advantageously according to the invention with the active substance mixtures according to the invention.
- the preferred ranges given above for the active substance combinations also apply to the treatment of these plants.
- Particularly emphasized is the plant treatment with the active ingredient combinations specifically mentioned in the present text.
- the good insecticidal and fungicidal action of the active compound combinations according to the invention is evident from the examples below. While the individual active ingredients have weaknesses in their effect, the combinations show an effect that goes beyond a simple sum of effects. A synergistic effect is always present in the case of insecticides and fungicides whenever the insecticidal or fungicidal action of the active substance combinations is greater than the sum of the effects of the individually applied active substances.
- X means the degree of killing or efficiency, expressed in% of the untreated control, when using the active substance A in an application rate of m ppm or g / ha,
- Y means the degree of killing or efficiency, expressed in% of the untreated control, when using the active ingredient B at an application rate of n ppm or g / ha, and
- E means the degree of killing or efficiency, expressed in% of the untreated control, when using the active compounds A and B at application rates of m and nppm or g / ha,
- the degree of kill or efficiency is determined in%. It means 0% a degree of kill or efficiency equal to that of the control, while a kill rate of 100% means that all animals are dead and an efficiency of 100% means that no infestation is observed.
- Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
- Cabbage leaves (Brassica oleracea) which are heavily infested with the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration.
- the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
- the determined kill values are calculated according to the Colby formula.
- Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
- Cabbage leaves (Brassica oleracea) are treated by spraying with the preparation of active compound in the desired concentration and with larvae of the horseradish beetle (Phaedon cochleariae) as long as the leaves are still moist.
- the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
- the determined kill values are calculated according to the Colby formula.
- Table B 1 Phaedon cochleariae larval test
- Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
- Cabbage leaves (Brassica oleracea) are treated by spraying with the preparation of active compound in the desired concentration and are populated with larvae of the armyworm (Spodoptera frugiperda) while the leaves are still moist.
- the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
- the determined kill values are calculated according to the Colby formula.
- Emulsifier 2 parts by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
- Cotton leaves which are heavily infested with the cotton aphid (Aphis gossypii) are treated by spraying with the preparation of active compound in the desired concentration.
- the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
- the determined kill values are calculated according to the Colby formula.
- Emulsifier 2 parts by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
- Cabbage leaves (Brassica oleracea) which are heavily infested with the green peach aphid (Myzus persicae) are treated by dripping wet spray with the preparation of active compound in the desired concentration.
- the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
- the determined kill values are calculated according to the Colby formula.
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Abstract
Description
Claims
Priority Applications (10)
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UAA201301421A UA111593C2 (uk) | 2010-07-07 | 2011-04-07 | Аміди антранілової кислоти у комбінації з фунгіцидами |
MX2013000195A MX347344B (es) | 2010-07-07 | 2011-07-04 | Amidas de acido antranilico en combinacion con fungicidas. |
JP2013517332A JP6088426B2 (ja) | 2010-07-07 | 2011-07-04 | 殺菌剤と組み合わせたアントラニルアミド |
BR112013000362A BR112013000362A2 (pt) | 2010-07-07 | 2011-07-04 | antranilamidas em combinação com fungicidas |
CA2804482A CA2804482C (en) | 2010-07-07 | 2011-07-04 | Anthranilamides in combination with fungicides |
KR1020137003065A KR101849561B1 (ko) | 2010-07-07 | 2011-07-04 | 살진균제와의 배합물로서의 안트라닐아미드 |
CN201180043077.1A CN103153065B (zh) | 2010-07-07 | 2011-07-04 | 与杀真菌剂相结合的邻氨基苯甲酰胺 |
AU2011275871A AU2011275871B2 (en) | 2010-07-07 | 2011-07-04 | Anthranilamides in combination with fungicides |
RU2013104939/13A RU2578801C2 (ru) | 2010-07-07 | 2011-07-04 | Амиды антраниловой кислоты в комбинации с фунгицидами |
EP11731306.4A EP2590511A2 (de) | 2010-07-07 | 2011-07-04 | Anthranilsäureamide in kombination mit fungiziden |
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US61/361,991 | 2010-07-07 |
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EP (1) | EP2590511A2 (de) |
JP (2) | JP6088426B2 (de) |
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CN (4) | CN103153065B (de) |
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AU (1) | AU2011275871B2 (de) |
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CN104222118A (zh) * | 2012-07-11 | 2014-12-24 | 陕西美邦农药有限公司 | 一种杀菌组合物 |
CN106212474A (zh) * | 2016-04-26 | 2016-12-14 | 南京华洲药业有限公司 | 一种含氟唑菌酰胺和噁唑菌酮的杀菌组合物及其应用 |
WO2019123195A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same. |
WO2019123194A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Anthranilamides, their use as insecticide and processes for preparing the same. |
WO2019150220A1 (en) | 2018-01-30 | 2019-08-08 | Pi Industries Ltd. | Novel anthranilamides, their use as insecticide and processes for preparing the same. |
WO2021023735A1 (en) * | 2019-08-08 | 2021-02-11 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal properties |
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CN104222118B (zh) * | 2012-07-11 | 2015-12-30 | 陕西美邦农药有限公司 | 一种杀菌组合物 |
CN106212474A (zh) * | 2016-04-26 | 2016-12-14 | 南京华洲药业有限公司 | 一种含氟唑菌酰胺和噁唑菌酮的杀菌组合物及其应用 |
WO2019123195A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same. |
WO2019123194A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Anthranilamides, their use as insecticide and processes for preparing the same. |
US12024510B2 (en) | 2017-12-20 | 2024-07-02 | Pi Industries Ltd. | Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same |
WO2019150220A1 (en) | 2018-01-30 | 2019-08-08 | Pi Industries Ltd. | Novel anthranilamides, their use as insecticide and processes for preparing the same. |
WO2021023735A1 (en) * | 2019-08-08 | 2021-02-11 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal properties |
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