HRP20000101A2 - Fungicidal combinations comprising phenylacrilic acid derivatives - Google Patents
Fungicidal combinations comprising phenylacrilic acid derivatives Download PDFInfo
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- HRP20000101A2 HRP20000101A2 HR20000101A HRP20000101A HRP20000101A2 HR P20000101 A2 HRP20000101 A2 HR P20000101A2 HR 20000101 A HR20000101 A HR 20000101A HR P20000101 A HRP20000101 A HR P20000101A HR P20000101 A2 HRP20000101 A2 HR P20000101A2
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- 230000000855 fungicidal effect Effects 0.000 title claims description 34
- 239000002253 acid Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 235
- 239000000460 chlorine Chemical group 0.000 claims description 45
- -1 4-chlorophenoxy Chemical group 0.000 claims description 43
- 229910052801 chlorine Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- 239000000417 fungicide Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 22
- 239000011737 fluorine Chemical group 0.000 claims description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 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 11
- 239000005757 Cyproconazole Substances 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000005758 Cyprodinil Substances 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 9
- 239000005822 Propiconazole Substances 0.000 claims description 9
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims description 9
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 239000005813 Penconazole Substances 0.000 claims description 8
- 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 8
- 230000003032 phytopathogenic effect Effects 0.000 claims description 8
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 7
- 239000005760 Difenoconazole Substances 0.000 claims description 7
- 239000005820 Prochloraz Substances 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- UELITFHSCLAHKR-UHFFFAOYSA-N acibenzolar-S-methyl Chemical group CSC(=O)C1=CC=CC2=C1SN=N2 UELITFHSCLAHKR-UHFFFAOYSA-N 0.000 claims description 7
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 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
- 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
- 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 6
- 239000005730 Azoxystrobin Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000005767 Epoxiconazole Substances 0.000 claims description 6
- 239000005839 Tebuconazole Substances 0.000 claims description 6
- 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 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 244000038559 crop plants Species 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 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 5
- 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 5
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims description 5
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 5
- 239000005772 Famoxadone Substances 0.000 claims description 5
- 239000005785 Fluquinconazole Substances 0.000 claims description 5
- 239000005787 Flutriafol Substances 0.000 claims description 5
- 239000005840 Tetraconazole Substances 0.000 claims description 5
- 239000005846 Triadimenol Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000006013 carbendazim Substances 0.000 claims description 5
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 claims description 5
- 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 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 claims description 5
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 claims description 4
- XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 claims description 4
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 4
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 4
- 239000005750 Copper hydroxide Substances 0.000 claims description 4
- 239000005775 Fenbuconazole Substances 0.000 claims description 4
- 239000005778 Fenpropimorph Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005802 Mancozeb Substances 0.000 claims description 4
- 239000005868 Metconazole Substances 0.000 claims description 4
- 239000011717 all-trans-retinol Substances 0.000 claims description 4
- 235000019169 all-trans-retinol Nutrition 0.000 claims description 4
- 150000001880 copper compounds Chemical class 0.000 claims description 4
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 4
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 4
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 claims description 4
- 229920000940 maneb Polymers 0.000 claims description 4
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 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 3
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 3
- 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 3
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 claims description 3
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 239000005734 Benalaxyl Substances 0.000 claims description 3
- 239000005741 Bromuconazole Substances 0.000 claims description 3
- 239000005745 Captan Substances 0.000 claims description 3
- 239000005752 Copper oxychloride Substances 0.000 claims description 3
- 239000005756 Cymoxanil Substances 0.000 claims description 3
- 239000005765 Dodemorph Substances 0.000 claims description 3
- 239000005780 Fluazinam Substances 0.000 claims description 3
- 239000005789 Folpet Substances 0.000 claims description 3
- 239000005797 Iprovalicarb Substances 0.000 claims description 3
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 claims description 3
- 239000005807 Metalaxyl Substances 0.000 claims description 3
- 239000005809 Metiram Substances 0.000 claims description 3
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 claims description 3
- 239000005828 Pyrimethanil Substances 0.000 claims description 3
- 239000005837 Spiroxamine Substances 0.000 claims description 3
- 229930182692 Strobilurin Natural products 0.000 claims description 3
- 239000005858 Triflumizole Substances 0.000 claims description 3
- 239000005859 Triticonazole Substances 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 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 3
- HJJVPARKXDDIQD-UHFFFAOYSA-N bromuconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCC(Br)C1 HJJVPARKXDDIQD-UHFFFAOYSA-N 0.000 claims description 3
- 229940117949 captan Drugs 0.000 claims description 3
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 claims description 3
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 claims description 3
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 claims description 3
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims description 3
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical group COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 claims description 3
- 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 3
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 claims description 3
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000257 metiram Polymers 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 claims description 3
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 claims description 3
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 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 2
- YNNUSGIPVFPVBX-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC(C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-UHFFFAOYSA-N 0.000 claims description 2
- CLGXIZQHFSCMTK-UHFFFAOYSA-N 2-chloro-n-[2-(4-fluorophenyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl CLGXIZQHFSCMTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- FSTUHOYKPMRFLZ-UHFFFAOYSA-N C=1C=CC=CC=1C(=NOC)C=NOCC1=CC=CC=C1C(=C)C(N)=O Chemical compound C=1C=CC=CC=1C(=NOC)C=NOCC1=CC=CC=C1C(=C)C(N)=O FSTUHOYKPMRFLZ-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—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
- 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
- A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9718366.9A GB9718366D0 (en) | 1997-08-29 | 1997-08-29 | Novel combinations |
| PCT/EP1998/005453 WO1999011125A1 (en) | 1997-08-29 | 1998-08-27 | Fungicidal combinations comprising phenylacrylic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20000101A2 true HRP20000101A2 (en) | 2001-04-30 |
Family
ID=10818251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20000101A HRP20000101A2 (en) | 1997-08-29 | 2000-02-25 | Fungicidal combinations comprising phenylacrilic acid derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6235684B1 (es) |
| EP (1) | EP1006795B1 (es) |
| JP (1) | JP2001514193A (es) |
| KR (1) | KR20010023321A (es) |
| CN (1) | CN1268025A (es) |
| AR (1) | AR015424A1 (es) |
| AT (1) | ATE234556T1 (es) |
| AU (1) | AU734458B2 (es) |
| BR (1) | BR9812022A (es) |
| CA (1) | CA2293253A1 (es) |
| CR (1) | CR5837A (es) |
| DE (1) | DE69812371T2 (es) |
| DK (1) | DK1006795T3 (es) |
| ES (1) | ES2195394T3 (es) |
| GB (1) | GB9718366D0 (es) |
| GT (1) | GT199800119A (es) |
| HR (1) | HRP20000101A2 (es) |
| HU (1) | HUP0003308A3 (es) |
| IL (1) | IL134299A0 (es) |
| PL (1) | PL337992A1 (es) |
| PT (1) | PT1006795E (es) |
| RU (1) | RU2193847C2 (es) |
| SK (1) | SK2492000A3 (es) |
| TW (1) | TW418071B (es) |
| WO (1) | WO1999011125A1 (es) |
| ZA (1) | ZA987840B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA61064C2 (uk) * | 1997-12-02 | 2003-11-17 | Рон-Пуленк Агро | Синергічна фунгіцидна композиція, що містить 2-інідазолін-5-он та спосіб боротьби з фітопатогенними грибками культур |
| WO1999056551A1 (de) * | 1998-05-04 | 1999-11-11 | Basf Aktiengesellschaft | Fungizide mischungen |
| FR2789551B1 (fr) * | 1999-02-12 | 2002-06-21 | Aventis Cropscience Sa | Compositions fongicides pour la protection des fruits |
| JP4351789B2 (ja) | 1999-07-16 | 2009-10-28 | 石原産業株式会社 | 有害生物防除用組成物および有害生物の防除方法 |
| US6428654B1 (en) * | 2000-04-05 | 2002-08-06 | Hercules Incorporated | Fungicidal method |
| MXPA03011494A (es) * | 2001-06-14 | 2004-03-19 | Syngenta Participations Ag | Composicion y metodo para mejorar el crecimiento de plantas. |
| DE10228102A1 (de) * | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| CN102165961B (zh) * | 2003-10-31 | 2013-10-23 | 石原产业株式会社 | 杀菌剂组合物和植物病害的防除方法 |
| CA2590244A1 (en) * | 2004-12-23 | 2006-07-06 | Basf Aktiengesellschaft | Fungicidal mixtures containing enestroburin and at least one active substance from the group of azoles |
| EP3047731A1 (en) * | 2015-01-21 | 2016-07-27 | Basf Se | Method for combating soybean rust comprising treating soybean with (2E)-2-[3-substituted-2 [[(E)-[(2E)-2-alkoxyimino-1-methyl-2-phenyl-ethylidene]amino]oxymethyl]phenyl]-2-methoxy-imino-N-methyl-acetamides |
| UA107869U (uk) * | 2015-12-21 | 2016-06-24 | Товариство З Обмеженою Відповідальністю "Альфа Хімгруп" | Фунгіцидна композиція для передпосівної обробки насіння пшениці |
| CN105831140B (zh) * | 2016-04-26 | 2018-07-17 | 南京华洲药业有限公司 | 一种含氟唑菌酰胺和福美双的杀菌组合物及其应用 |
| CN105794792B (zh) * | 2016-04-26 | 2018-05-22 | 南京华洲药业有限公司 | 一种含氟唑菌酰胺和恶霜灵的杀菌组合物及其应用 |
| CN105941407B (zh) * | 2016-05-26 | 2018-04-20 | 南京华洲药业有限公司 | 一种含氟醚菌酰胺和咯菌腈的杀菌组合物及其应用 |
| CN107853325A (zh) * | 2017-11-14 | 2018-03-30 | 潍坊友容实业有限公司 | 盐碱地作物高效施肥杀菌剂 |
| RU2681739C1 (ru) * | 2018-06-21 | 2019-03-12 | Акционерное общество "Щелково Агрохим" | Фунгицидная композиция, обладающая синергетической активностью |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4304172A1 (de) | 1993-02-12 | 1994-08-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE4318285A1 (de) | 1993-06-02 | 1994-12-08 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| US6518304B1 (en) * | 1993-12-02 | 2003-02-11 | Sumitomo Chemical Company, Limited | Fungicidal composition |
| HU219157B (hu) * | 1994-01-05 | 2001-02-28 | Novartis Ag. | Peszticid hatású [dioxa-diaza/vagy oxa-triaza/-heptadienil-fenil]-akrilsav- és glioxilsav-származékok, előállításuk és alkalmazásuk |
| MX9603143A (es) | 1994-02-04 | 1997-05-31 | Basf Ag | Derivados del acido fenilacetico, procedimientos y productos intermedios para su obtencion y productos que los contienen. |
| FR2722652B1 (fr) * | 1994-07-22 | 1997-12-19 | Rhone Poulenc Agrochimie | Composition fongicide comprenant une 2-imidazoline-5-one |
| DE4444911A1 (de) | 1994-12-16 | 1996-06-27 | Basf Ag | Fungizide Mischung |
| UA54395C2 (uk) | 1995-06-16 | 2003-03-17 | Баєр Акціенгезельшафт | Фітобактерициднa композиція, спосіб контролю та запобігання хворобам рослин, матеріал для розмноження рослин |
| MY115814A (en) | 1995-06-16 | 2003-09-30 | Bayer Ip Gmbh | Crop protection compositions |
| TW318777B (es) * | 1995-06-29 | 1997-11-01 | Novartis Ag | |
| FR2737086B1 (fr) * | 1995-07-24 | 1997-08-22 | Rhone Poulenc Agrochimie | Composition fongicide comprenant un compose analogue de la strobilurine |
| WO1997006677A1 (de) * | 1995-08-17 | 1997-02-27 | Basf Aktiengesellschaft | Fungizide mischungen eines oximethercarbonsäureamids mit anilinopyrimidinen |
| ATE184751T1 (de) * | 1995-08-17 | 1999-10-15 | Basf Ag | Fungizide mischungen eines oximethercarbonsäureamids mit azolderivaten |
| BR9610002A (pt) * | 1995-08-17 | 1999-07-06 | Basf Ag | Mistura fungicida processo para controlar fungos danosos e uso de um composto |
| ATE185679T1 (de) * | 1995-08-17 | 1999-11-15 | Basf Ag | Fungizide mischungen eines oximethercarbonsäureamids mit einem n- trichlormethylthiophthalimid |
| DE59603362D1 (de) * | 1995-08-17 | 1999-11-18 | Basf Ag | Fungizide mischungen eines oximethercarbonsäureamids mit fenarimol |
| WO1997006679A1 (de) * | 1995-08-17 | 1997-02-27 | Basf Aktiengesellschaft | Fungizide mischungen |
| ATE185472T1 (de) * | 1995-08-17 | 1999-10-15 | Basf Ag | Fungizide mischungen eines oximethercarbonsäureamids mit einem morpholin- oder piperidinderivat |
| ATE185240T1 (de) * | 1995-08-17 | 1999-10-15 | Basf Ag | Fungizide mischungen eines oximethercarbonsäureamids mit einem dithiocarbamat |
| TW384208B (en) | 1995-09-22 | 2000-03-11 | Basf Ag | Compositions and methods for controlling harmful fungi |
| FR2740005A1 (fr) * | 1995-10-19 | 1997-04-25 | Rhone Poulenc Agrochimie | Composition fongicide synergique comprenant un compose analogue de la strobilurine |
| WO1997015189A1 (de) * | 1995-10-25 | 1997-05-01 | Basf Aktiengesellschaft | Fungizide mischungen von oximethercarbonsäureestern mit kupferhaltigen fungiziden |
| DE19543746A1 (de) * | 1995-11-24 | 1997-05-28 | Basf Ag | Fungizide Mittel |
| IL124523A (en) * | 1995-12-07 | 2003-09-17 | Bayer Ag | Methoxyacrylic acid derivatives, a process for their production and use thereof in controlling insects, acarinas and phytopathogenic microorganisms |
| FR2742633A1 (fr) * | 1995-12-22 | 1997-06-27 | Rhone Poulenc Agrochimie | Composition fongicide synergique comprenant un compose analogue de la strobilurine |
-
1997
- 1997-08-29 GB GBGB9718366.9A patent/GB9718366D0/en active Pending
-
1998
- 1998-07-20 TW TW087111837A patent/TW418071B/zh not_active IP Right Cessation
- 1998-07-29 GT GT199800119A patent/GT199800119A/es unknown
- 1998-08-11 CR CR5837A patent/CR5837A/es unknown
- 1998-08-27 BR BR9812022-0A patent/BR9812022A/pt not_active IP Right Cessation
- 1998-08-27 RU RU2000107120/04A patent/RU2193847C2/ru not_active IP Right Cessation
- 1998-08-27 US US09/486,519 patent/US6235684B1/en not_active Expired - Fee Related
- 1998-08-27 CA CA002293253A patent/CA2293253A1/en not_active Abandoned
- 1998-08-27 CN CN98808486A patent/CN1268025A/zh active Pending
- 1998-08-27 WO PCT/EP1998/005453 patent/WO1999011125A1/en not_active Application Discontinuation
- 1998-08-27 DE DE69812371T patent/DE69812371T2/de not_active Expired - Fee Related
- 1998-08-27 HU HU0003308A patent/HUP0003308A3/hu unknown
- 1998-08-27 PL PL98337992A patent/PL337992A1/xx unknown
- 1998-08-27 ES ES98947466T patent/ES2195394T3/es not_active Expired - Lifetime
- 1998-08-27 EP EP98947466A patent/EP1006795B1/en not_active Expired - Lifetime
- 1998-08-27 DK DK98947466T patent/DK1006795T3/da active
- 1998-08-27 SK SK249-2000A patent/SK2492000A3/sk unknown
- 1998-08-27 KR KR1020007001956A patent/KR20010023321A/ko not_active Application Discontinuation
- 1998-08-27 AU AU94373/98A patent/AU734458B2/en not_active Ceased
- 1998-08-27 AR ARP980104290A patent/AR015424A1/es unknown
- 1998-08-27 JP JP2000508242A patent/JP2001514193A/ja active Pending
- 1998-08-27 PT PT98947466T patent/PT1006795E/pt unknown
- 1998-08-27 IL IL13429998A patent/IL134299A0/xx unknown
- 1998-08-27 AT AT98947466T patent/ATE234556T1/de not_active IP Right Cessation
- 1998-08-28 ZA ZA987840A patent/ZA987840B/xx unknown
-
2000
- 2000-02-25 HR HR20000101A patent/HRP20000101A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL337992A1 (en) | 2000-09-25 |
| CA2293253A1 (en) | 1999-03-11 |
| AU9437398A (en) | 1999-03-22 |
| EP1006795B1 (en) | 2003-03-19 |
| AR015424A1 (es) | 2001-05-02 |
| DE69812371T2 (de) | 2003-10-23 |
| PT1006795E (pt) | 2003-06-30 |
| ES2195394T3 (es) | 2003-12-01 |
| RU2193847C2 (ru) | 2002-12-10 |
| WO1999011125A1 (en) | 1999-03-11 |
| AU734458B2 (en) | 2001-06-14 |
| CN1268025A (zh) | 2000-09-27 |
| BR9812022A (pt) | 2000-09-26 |
| EP1006795A1 (en) | 2000-06-14 |
| GB9718366D0 (en) | 1997-11-05 |
| DE69812371D1 (de) | 2003-04-24 |
| JP2001514193A (ja) | 2001-09-11 |
| GT199800119A (es) | 2000-01-20 |
| ATE234556T1 (de) | 2003-04-15 |
| IL134299A0 (en) | 2001-04-30 |
| SK2492000A3 (en) | 2000-07-11 |
| ZA987840B (en) | 1999-03-01 |
| CR5837A (es) | 1999-04-05 |
| HUP0003308A2 (hu) | 2001-01-29 |
| US6235684B1 (en) | 2001-05-22 |
| TW418071B (en) | 2001-01-11 |
| HUP0003308A3 (en) | 2001-03-28 |
| DK1006795T3 (da) | 2003-07-14 |
| KR20010023321A (ko) | 2001-03-26 |
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Owner name: SYNGENTA PARTICIPATIONS AG, CH Owner name: BAYER AKTIENGESELLSCHAFT, DE |
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