JP2015518024A5 - - Google Patents
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- Publication number
- JP2015518024A5 JP2015518024A5 JP2015514478A JP2015514478A JP2015518024A5 JP 2015518024 A5 JP2015518024 A5 JP 2015518024A5 JP 2015514478 A JP2015514478 A JP 2015514478A JP 2015514478 A JP2015514478 A JP 2015514478A JP 2015518024 A5 JP2015518024 A5 JP 2015518024A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- chloropyridin
- amino
- trifluoromethyl
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 bencrothiaz Chemical compound 0.000 claims 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 23
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 18
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 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 11
- 239000003112 inhibitor Substances 0.000 claims 11
- 239000002917 insecticide Substances 0.000 claims 10
- 244000063299 Bacillus subtilis Species 0.000 claims 9
- 235000014469 Bacillus subtilis Nutrition 0.000 claims 9
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
- 230000000853 biopesticidal effect Effects 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 239000005783 Fluopyram Substances 0.000 claims 6
- 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 6
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 6
- 239000000417 fungicide Substances 0.000 claims 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 claims 5
- KNDVJPKNBVIKML-UHFFFAOYSA-N tetraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(CN2N=C(N=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl KNDVJPKNBVIKML-UHFFFAOYSA-N 0.000 claims 5
- 125000003368 amide group Chemical group 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 230000000855 fungicidal effect Effects 0.000 claims 4
- 235000005152 nicotinamide Nutrition 0.000 claims 4
- 239000011570 nicotinamide Substances 0.000 claims 4
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims 4
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 3
- MEQLNUTUGWFNIB-UHFFFAOYSA-N 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoropropyl)propanedinitrile Chemical compound FC(F)C(F)(F)C(F)(F)C(F)(F)CC(C#N)(C#N)CCC(F)(F)F MEQLNUTUGWFNIB-UHFFFAOYSA-N 0.000 claims 3
- PIDORWGUVHFLRF-UHFFFAOYSA-N 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)propanedinitrile Chemical compound FC(F)C(F)(F)C(F)(F)C(F)(F)CC(C#N)(C#N)CCC(F)(F)C(F)(F)F PIDORWGUVHFLRF-UHFFFAOYSA-N 0.000 claims 3
- LMBOBAWFGUTZRU-UHFFFAOYSA-N 2-(5-fluoropyridin-3-yl)-5-(6-pyrimidin-2-ylpyridin-2-yl)-1,3-thiazole Chemical compound FC1=CN=CC(C=2SC(=CN=2)C=2N=C(C=CC=2)C=2N=CC=CN=2)=C1 LMBOBAWFGUTZRU-UHFFFAOYSA-N 0.000 claims 3
- RUUBFCPAVMVRMA-UHFFFAOYSA-N 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-5-(trifluoromethyl)-1,2,4-triazol-3-amine Chemical compound C1=C(S(=O)CC(F)(F)F)C(C)=CC(F)=C1N1C(N)=NC(C(F)(F)F)=N1 RUUBFCPAVMVRMA-UHFFFAOYSA-N 0.000 claims 3
- WVKDQESLHACCIT-UHFFFAOYSA-N 2-[3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl]ethyl hydrogen carbonate Chemical compound C1CN(OC)CCC21C(CCOC(O)=O)=C(C=1C(=CC=C(C)C=1)C)C(=O)N2 WVKDQESLHACCIT-UHFFFAOYSA-N 0.000 claims 3
- SLHPVQGXHAIIAB-UHFFFAOYSA-N 2-cyano-3-(difluoromethoxy)-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(OC(F)F)=C1C#N SLHPVQGXHAIIAB-UHFFFAOYSA-N 0.000 claims 3
- BZJMCXRJRICDPD-UHFFFAOYSA-N 2-cyano-3-(difluoromethoxy)-n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC(OC(F)F)=C1C#N BZJMCXRJRICDPD-UHFFFAOYSA-N 0.000 claims 3
- FTRBGJBAWNIOCJ-UHFFFAOYSA-N 2-cyano-3-(difluoromethoxy)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(OC(F)F)=C1C#N FTRBGJBAWNIOCJ-UHFFFAOYSA-N 0.000 claims 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
- KRYQDBFHAFVBSW-UHFFFAOYSA-N 2-pyridin-3-yl-5-(6-pyrimidin-2-ylpyridin-2-yl)-1,3-thiazole Chemical compound C=1N=C(C=2C=NC=CC=2)SC=1C(N=1)=CC=CC=1C1=NC=CC=N1 KRYQDBFHAFVBSW-UHFFFAOYSA-N 0.000 claims 3
- IDMIADZAXUGPDR-UHFFFAOYSA-N 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one Chemical compound C1CN(OC)CCC21C(O)=C(C=1C(=CC=C(C)C=1)C)C(=O)N2 IDMIADZAXUGPDR-UHFFFAOYSA-N 0.000 claims 3
- CJXVXIQIPJXTIC-UHFFFAOYSA-N 3-[(2-chloro-1,3-thiazol-5-yl)methyl-(2-fluoroethyl)amino]-2h-furan-5-one Chemical compound C=1C(=O)OCC=1N(CCF)CC1=CN=C(Cl)S1 CJXVXIQIPJXTIC-UHFFFAOYSA-N 0.000 claims 3
- STPZTYAWMGWIIB-UHFFFAOYSA-N 3-[(5,6-dichloropyridin-3-yl)methyl-(2-fluoroethyl)amino]-2h-furan-5-one Chemical compound C=1C(=O)OCC=1N(CCF)CC1=CN=C(Cl)C(Cl)=C1 STPZTYAWMGWIIB-UHFFFAOYSA-N 0.000 claims 3
- QRURGXUYUFRZJU-UHFFFAOYSA-N 3-[(6-chloro-5-fluoropyridin-3-yl)methyl-methylamino]-2h-furan-5-one Chemical compound C=1C(=O)OCC=1N(C)CC1=CN=C(Cl)C(F)=C1 QRURGXUYUFRZJU-UHFFFAOYSA-N 0.000 claims 3
- SNNQRPYPSAJQKV-UHFFFAOYSA-N 3-[(6-chloropyridin-3-yl)methyl-(2-fluoroethyl)amino]-2h-furan-5-one Chemical compound C=1C(=O)OCC=1N(CCF)CC1=CC=C(Cl)N=C1 SNNQRPYPSAJQKV-UHFFFAOYSA-N 0.000 claims 3
- VYYVIYOMJIBVTK-UHFFFAOYSA-N 3-[(6-chloropyridin-3-yl)methyl-cyclopropylamino]-2h-furan-5-one Chemical compound C1=NC(Cl)=CC=C1CN(C=1COC(=O)C=1)C1CC1 VYYVIYOMJIBVTK-UHFFFAOYSA-N 0.000 claims 3
- JPHQHJFHSAVFQJ-UHFFFAOYSA-N 3-[2,2-difluoroethyl-[(6-fluoropyridin-3-yl)methyl]amino]-2h-furan-5-one Chemical compound C=1C(=O)OCC=1N(CC(F)F)CC1=CC=C(F)N=C1 JPHQHJFHSAVFQJ-UHFFFAOYSA-N 0.000 claims 3
- UKPDFCZYKKAJTK-UHFFFAOYSA-N 3-[3-(4-fluorophenyl)-2,6-dimethylphenyl]-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one Chemical compound CC1=CC=C(C=2C=CC(F)=CC=2)C(C)=C1C(C(N1)=O)=C(O)C21CCOCC2 UKPDFCZYKKAJTK-UHFFFAOYSA-N 0.000 claims 3
- RAMUASXTSSXCMB-UHFFFAOYSA-N 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide Chemical compound C1CC1C(C)NC(=O)C1=CC(Cl)=CC(Br)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl RAMUASXTSSXCMB-UHFFFAOYSA-N 0.000 claims 3
- KJODWAHKHVUXEU-UHFFFAOYSA-N 4-(difluoromethoxy)-n-ethyl-n-methyl-1,1-dioxo-1,2-benzothiazol-3-amine Chemical compound C1=CC(OC(F)F)=C2C(N(C)CC)=NS(=O)(=O)C2=C1 KJODWAHKHVUXEU-UHFFFAOYSA-N 0.000 claims 3
- QAZKMKHFYSRSQW-UHFFFAOYSA-N 4-[(6-chloropyridin-3-yl)methyl-(2,2-difluoroethyl)amino]-5h-1,3-oxazol-2-one Chemical compound N=1C(=O)OCC=1N(CC(F)F)CC1=CC=C(Cl)N=C1 QAZKMKHFYSRSQW-UHFFFAOYSA-N 0.000 claims 3
- WVTDRCZFORVLMD-UHFFFAOYSA-N 4-[(6-chloropyridin-3-yl)methyl-cyclopropylamino]-5h-1,3-oxazol-2-one Chemical compound C1=NC(Cl)=CC=C1CN(C=1COC(=O)N=1)C1CC1 WVTDRCZFORVLMD-UHFFFAOYSA-N 0.000 claims 3
- OSNASGFBZNDZTG-UHFFFAOYSA-N 4-[(6-chloropyridin-3-yl)methyl-ethylamino]-5h-1,3-oxazol-2-one Chemical compound N=1C(=O)OCC=1N(CC)CC1=CC=C(Cl)N=C1 OSNASGFBZNDZTG-UHFFFAOYSA-N 0.000 claims 3
- YEAPNRDPPDWVPC-UHFFFAOYSA-N 4-[(6-chloropyridin-3-yl)methyl-methylamino]-5h-1,3-oxazol-2-one Chemical compound N=1C(=O)OCC=1N(C)CC1=CC=C(Cl)N=C1 YEAPNRDPPDWVPC-UHFFFAOYSA-N 0.000 claims 3
- XVSSMEWAXFOWCI-UHFFFAOYSA-N 4-but-2-ynoxy-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine Chemical compound CC#CCOC1=NC=NC(N2CC(C)CC(C)C2)=C1F XVSSMEWAXFOWCI-UHFFFAOYSA-N 0.000 claims 3
- WCDYJLBZIHIBLJ-UHFFFAOYSA-N 5-[5-(2-chloropyridin-4-yl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-(1,2,4-triazol-1-yl)benzonitrile Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)N=CC=2)CC=1C(C=C1C#N)=CC=C1N1C=NC=N1 WCDYJLBZIHIBLJ-UHFFFAOYSA-N 0.000 claims 3
- KIRTWJNAASMOKG-UHFFFAOYSA-N 5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-(1,2,4-triazol-1-yl)benzonitrile Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(C=C1C#N)=CC=C1N1C=NC=N1 KIRTWJNAASMOKG-UHFFFAOYSA-N 0.000 claims 3
- 239000005878 Azadirachtin Substances 0.000 claims 3
- 241000194103 Bacillus pumilus Species 0.000 claims 3
- RPQQDPWGFFHSOL-UHFFFAOYSA-N CCCCCCCCCC(C=CCC)=O Chemical compound CCCCCCCCCC(C=CCC)=O RPQQDPWGFFHSOL-UHFFFAOYSA-N 0.000 claims 3
- MQEIRDUPXBZEGB-UHFFFAOYSA-N CCN(C(O)=O)N(CC)C(=O)C1=CC(Br)=CC(Br)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl Chemical compound CCN(C(O)=O)N(CC)C(=O)C1=CC(Br)=CC(Br)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl MQEIRDUPXBZEGB-UHFFFAOYSA-N 0.000 claims 3
- 239000005867 Iprodione Substances 0.000 claims 3
- 241000635201 Pumilus Species 0.000 claims 3
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims 3
- BZMIHNKNQJJVRO-LVZFUZTISA-N [(e)-c-(3-chloro-2,6-dimethoxyphenyl)-n-ethoxycarbonimidoyl] benzoate Chemical compound COC=1C=CC(Cl)=C(OC)C=1C(=N/OCC)\OC(=O)C1=CC=CC=C1 BZMIHNKNQJJVRO-LVZFUZTISA-N 0.000 claims 3
- HTQSSESCIAFSNA-UHFFFAOYSA-N [[2-[[5-bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl]amino]-5-chloro-3-methylbenzoyl]-methylamino]carbamic acid Chemical compound OC(=O)NN(C)C(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl HTQSSESCIAFSNA-UHFFFAOYSA-N 0.000 claims 3
- XNARYMMPJCEKHP-UHFFFAOYSA-N [[2-[[5-bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl]amino]-5-cyano-3-methylbenzoyl]-ethylamino]carbamic acid Chemical compound CCN(NC(O)=O)C(=O)c1cc(cc(C)c1NC(=O)c1cc(Br)nn1-c1ncccc1Cl)C#N XNARYMMPJCEKHP-UHFFFAOYSA-N 0.000 claims 3
- UTKQRQNDGCEJAU-UHFFFAOYSA-N [[3,5-dibromo-2-[[5-bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl]amino]benzoyl]-ethylamino]carbamic acid Chemical compound OC(=O)NN(CC)C(=O)C1=CC(Br)=CC(Br)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl UTKQRQNDGCEJAU-UHFFFAOYSA-N 0.000 claims 3
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 claims 3
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 claims 3
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 229910001610 cryolite Inorganic materials 0.000 claims 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 3
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 3
- 235000013399 edible fruits Nutrition 0.000 claims 3
- GJEREQYJIQASAW-UHFFFAOYSA-N flufenerim Chemical compound CC(F)C1=NC=NC(NCCC=2C=CC(OC(F)(F)F)=CC=2)=C1Cl GJEREQYJIQASAW-UHFFFAOYSA-N 0.000 claims 3
- MLBZKOGAMRTSKP-UHFFFAOYSA-N fluralaner Chemical compound C1=C(C(=O)NCC(=O)NCC(F)(F)F)C(C)=CC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 MLBZKOGAMRTSKP-UHFFFAOYSA-N 0.000 claims 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 3
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 claims 3
- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 claims 3
- TUCSJFNYZJYLHE-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-2,7-dimethyl-2,3-dihydro-1-benzofuran-6-carbohydrazide Chemical compound CC1=C2OC(C)CC2=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 TUCSJFNYZJYLHE-UHFFFAOYSA-N 0.000 claims 3
- REAVUPQUTRQOII-UHFFFAOYSA-N n-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(CC(NC=2SCCN=2)C=2C(=C(C)C=CC=2)C)=C1 REAVUPQUTRQOII-UHFFFAOYSA-N 0.000 claims 3
- JIEAYFZXXGXYLF-UHFFFAOYSA-N n-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-2-(3-chloropyridin-2-yl)-5-[[5-(trifluoromethyl)tetrazol-2-yl]methyl]pyrazole-3-carboxamide Chemical compound CC1=CC(C#N)=CC(C(=O)NC(C)(C)C)=C1NC(=O)C1=CC(CN2N=C(N=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl JIEAYFZXXGXYLF-UHFFFAOYSA-N 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 235000013311 vegetables Nutrition 0.000 claims 3
- HVQHXBNMBZJPLK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methylprop-2-en-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound CC(=C)CNC1=C([S+]([O-])C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HVQHXBNMBZJPLK-UHFFFAOYSA-N 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- ISMGGJHYSVNEMP-UHFFFAOYSA-N 2-(3-chloropyridin-2-yl)-n-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-5-[[5-(trifluoromethyl)tetrazol-1-yl]methyl]pyrazole-3-carboxamide Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(CN2C(=NN=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl ISMGGJHYSVNEMP-UHFFFAOYSA-N 0.000 claims 2
- 241000238876 Acari Species 0.000 claims 2
- 239000005653 Bifenazate Substances 0.000 claims 2
- 241000238631 Hexapoda Species 0.000 claims 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims 2
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims 2
- 241000244206 Nematoda Species 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 239000005926 Pyridalyl Substances 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 claims 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 2
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- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims 1
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- IYYIUOWKEMQYNV-UHFFFAOYSA-N sodium;ethoxy-oxido-oxophosphanium Chemical compound [Na+].CCO[P+]([O-])=O IYYIUOWKEMQYNV-UHFFFAOYSA-N 0.000 claims 1
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| US10306889B2 (en) | 2012-05-30 | 2019-06-04 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| KR102095979B1 (ko) | 2012-05-30 | 2020-04-02 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 생물학적 방제제 및 살곤충제를 포함하는 조성물 |
| BR112014029224A2 (pt) | 2012-05-30 | 2017-06-27 | Bayer Cropscience Ag | composição que compreende um agente de controle biológico e um fungicida |
| MX373820B (es) | 2012-05-30 | 2020-03-24 | Bayer Cropscience Ag | Una composición que comprende un agente de control biológico y un fungicida seleccionado de inhibidores de la mitosis y la división celular y compuestos capaces de tener una acción en múltiples sitios. |
| NZ701495A (en) | 2012-05-30 | 2016-11-25 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| NZ742943A (en) | 2012-05-30 | 2019-04-26 | Bayer Cropscience Ag | Compositions comprising a biological control agent and a fungicide from the group consisting of inhibitors of the respiratory chain at complex i or ii |
| AU2013269723B2 (en) | 2012-05-30 | 2016-12-15 | Bayer Cropscience Ag | Composition comprising a biological control agent and a fungicide |
| KR102095974B1 (ko) | 2012-05-30 | 2020-04-02 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 생물학적 방제제 및 살곤충제를 포함하는 조성물 |
| KR20150023299A (ko) | 2012-05-30 | 2015-03-05 | 바이엘 크롭사이언스 아게 | 생물학적 방제제 및 에르고스테롤 생합성의 억제제로부터 선택된 살진균제를 포함하는 조성물 |
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| WO2015181008A1 (en) * | 2014-05-27 | 2015-12-03 | Basf Se | Ternary mixtures comprising biopesticides and chemical fungicides and chemical insecticides |
| ES2561908B2 (es) * | 2014-07-31 | 2016-12-01 | Universidad De Granada | Uso de Bacillus methylotrophicus como estimulante del crecimiento vegetal y medio de control biológico, y cepas aisladas de dicha especie |
| CN106035380A (zh) * | 2016-06-27 | 2016-10-26 | 中国烟草总公司郑州烟草研究院 | 含苯甲酰胺类、二硝基苯胺类杀菌剂和生防菌的菌药组合物、制剂及应用 |
| CN107771859A (zh) * | 2017-11-30 | 2018-03-09 | 广西南宁益土生物科技有限责任公司 | 一种含氟吡菌酰胺和枯草芽孢杆菌的杀线虫剂 |
| KR101889681B1 (ko) | 2018-02-13 | 2018-08-17 | 고려아연 주식회사 | 오토클레이브 및 오토클레이브의 염 제거방법 |
| AR116550A1 (es) | 2018-09-28 | 2021-05-19 | Bayer Ag | Combinación beneficiosa de agentes de control biológico bacteriano y ácidos grasos |
| CA3126761C (en) | 2019-01-15 | 2023-01-10 | Seminis Vegetable Seeds, Inc. | Green bean plants with improved disease resistance |
| US11807862B2 (en) * | 2019-01-15 | 2023-11-07 | Seminis Vegetable Seeds, Inc. | Green bean plants with improved disease resistance |
| CN111269862A (zh) * | 2020-03-17 | 2020-06-12 | 陈建军 | 用于荧光假单胞菌高产铁载体的发酵培养基及其发酵培养方法 |
| WO2022110093A1 (zh) * | 2020-11-29 | 2022-06-02 | 南京溧水高新创业投资管理有限公司 | 一种用于植物保护生长调节的微生物农药制剂 |
| CN113016452A (zh) * | 2021-03-02 | 2021-06-25 | 天津市农业科学院 | 一种利用捕食螨防治桃树害螨的方法及应用 |
| CN114793655B (zh) * | 2022-06-01 | 2024-05-17 | 江苏青好景观园艺有限公司 | 一种斯帝芬冬青的扦插方法 |
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| CN100334201C (zh) * | 2005-09-23 | 2007-08-29 | 中国农业大学 | 一株枯草芽孢杆菌及其应用 |
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| NZ600929A (en) * | 2007-09-20 | 2014-02-28 | Basf Se | Combinations comprising a fungicidal strain and an active compound |
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| DE102008047466A1 (de) | 2008-09-17 | 2010-04-15 | Valeo Schalter Und Sensoren Gmbh | Magnetbaugruppe für eine Drehmoment- und/oder Drehwinkelsensoranordnung mit einem Magnetring und Herstellungsverfahren |
| EP2201838A1 (de) * | 2008-12-05 | 2010-06-30 | Bayer CropScience AG | Wirkstoff-Nützlings-Kombinationen mit insektiziden und akariziden Eigenschaften |
| CA2747035C (en) | 2008-12-18 | 2017-01-24 | Bayer Cropscience Ag | Tetrazole substituted anthranilic acid amides as pesticides |
| MX354266B (es) | 2009-05-06 | 2018-02-21 | Bayer Cropscience Lp | Un metodo para aumentar el vigor y/o el rendimiento de plantas agricolas bajo presion de patogeno esencialmente no existente. |
| BRPI1008143A2 (pt) * | 2009-06-05 | 2015-08-25 | Basf Se | Mistura composição agroquimica metodo para o combatre de fungos novicios fitopatogenicos e material de propagação de planta |
| WO2011100424A1 (en) | 2010-02-12 | 2011-08-18 | Bayer Croscience Lp | Methods for reducing nematode damage to plants |
| PH12012502061A1 (en) * | 2010-04-14 | 2017-08-09 | Bayer Ip Gmbh | Active compound combinations |
| EP2557927A4 (en) | 2010-04-15 | 2013-12-18 | Basf Se | FUNGICIDAL MIXTURES I WITH CHINAZOLINES |
| BR112012031277A2 (pt) * | 2010-06-09 | 2016-09-27 | Syngenta Participations Ag | "misturas pesticidas compreendendo derivados de isoxazolina" |
| CN103298341B (zh) | 2010-09-22 | 2016-06-08 | 拜耳知识产权有限责任公司 | 活性成分在抗线虫作物中用于防治线虫的用途 |
| EP2460407A1 (de) | 2010-12-01 | 2012-06-06 | Bayer CropScience AG | Wirkstoffkombinationen umfassend Pyridylethylbenzamide und weitere Wirkstoffe |
| PE20141468A1 (es) | 2010-12-21 | 2014-11-05 | Bayer Cropscience Lp | Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas |
| CN102047915B (zh) | 2011-01-11 | 2013-03-13 | 海利尔药业集团股份有限公司 | 一种含有噻虫酰胺的杀虫组合物 |
| US9241493B2 (en) | 2011-06-14 | 2016-01-26 | Bayer Intellectual Property Gmbh | Use of an enaminocarbonyl compound in combination with a biological control agent |
| EP2604118A1 (en) * | 2011-12-15 | 2013-06-19 | Bayer CropScience AG | Active ingredient combinations having insecticidal and acaricidal properties |
| EP2606732A1 (en) | 2011-12-19 | 2013-06-26 | Bayer CropScience AG | Use of an anthranilic diamide derivatives with heteroaromatic and heterocyclic substituents in combination with a biological control agent |
| BR112014029224A2 (pt) | 2012-05-30 | 2017-06-27 | Bayer Cropscience Ag | composição que compreende um agente de controle biológico e um fungicida |
| AU2013269723B2 (en) | 2012-05-30 | 2016-12-15 | Bayer Cropscience Ag | Composition comprising a biological control agent and a fungicide |
| AU2013269661B2 (en) | 2012-05-30 | 2016-10-27 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| US20150104417A1 (en) | 2012-05-30 | 2015-04-16 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| KR102095974B1 (ko) | 2012-05-30 | 2020-04-02 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 생물학적 방제제 및 살곤충제를 포함하는 조성물 |
| US9968097B2 (en) | 2012-05-30 | 2018-05-15 | Bayer Cropscience Ag | Composition comprising a biological control agent and a fungicide selected from inhibitors of the lipid membrane synthesis, the melanine biosynthesis, the nucleic acid synthesis or the signal transduction |
| US10306889B2 (en) | 2012-05-30 | 2019-06-04 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| NZ701495A (en) | 2012-05-30 | 2016-11-25 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| KR20150023299A (ko) | 2012-05-30 | 2015-03-05 | 바이엘 크롭사이언스 아게 | 생물학적 방제제 및 에르고스테롤 생합성의 억제제로부터 선택된 살진균제를 포함하는 조성물 |
| EP3292764A3 (en) | 2012-05-30 | 2018-04-25 | Bayer CropScience Aktiengesellschaft | Composition comprising a biological control agent and a fungicide selected from inhibitors of the respiratory chain at complex iii |
| KR102095979B1 (ko) | 2012-05-30 | 2020-04-02 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 생물학적 방제제 및 살곤충제를 포함하는 조성물 |
| MX373820B (es) | 2012-05-30 | 2020-03-24 | Bayer Cropscience Ag | Una composición que comprende un agente de control biológico y un fungicida seleccionado de inhibidores de la mitosis y la división celular y compuestos capaces de tener una acción en múltiples sitios. |
| NZ742943A (en) | 2012-05-30 | 2019-04-26 | Bayer Cropscience Ag | Compositions comprising a biological control agent and a fungicide from the group consisting of inhibitors of the respiratory chain at complex i or ii |
-
2013
- 2013-05-29 KR KR1020147035510A patent/KR102023962B1/ko active Active
- 2013-05-29 AU AU2013269665A patent/AU2013269665B2/en active Active
- 2013-05-29 MX MX2014014195A patent/MX355540B/es active IP Right Grant
- 2013-05-29 CN CN201710846552.8A patent/CN107568247A/zh active Pending
- 2013-05-29 EP EP13725679.8A patent/EP2854536A1/en not_active Withdrawn
- 2013-05-29 BR BR112014029118A patent/BR112014029118A2/pt not_active Application Discontinuation
- 2013-05-29 CN CN201380028131.4A patent/CN104902753A/zh active Pending
- 2013-05-29 JP JP2015514478A patent/JP6181163B2/ja active Active
- 2013-05-29 WO PCT/EP2013/061039 patent/WO2013178666A1/en not_active Ceased
- 2013-05-29 NZ NZ701664A patent/NZ701664A/en unknown
- 2013-05-29 US US14/404,025 patent/US9370188B2/en active Active
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2014
- 2014-10-22 IL IL235264A patent/IL235264A/en active IP Right Grant
- 2014-12-19 ZA ZA2014/09421A patent/ZA201409421B/en unknown
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2016
- 2016-05-19 US US15/159,134 patent/US9801387B2/en not_active Expired - Fee Related
- 2016-11-15 AU AU2016259314A patent/AU2016259314B2/en not_active Ceased
-
2017
- 2017-06-29 IL IL253232A patent/IL253232A0/en unknown
-
2018
- 2018-07-10 HK HK18108914.6A patent/HK1249363A1/zh unknown
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