JP2014516064A5 - - Google Patents

Info

Publication number

JP2014516064A5

JP2014516064A5 JP2014514021A JP2014514021A JP2014516064A5 JP 2014516064 A5 JP2014516064 A5 JP 2014516064A5 JP 2014514021 A JP2014514021 A JP 2014514021A JP 2014514021 A JP2014514021 A JP 2014514021A JP 2014516064 A5 JP2014516064 A5 JP 2014516064A5

Authority

JP

Japan

Prior art keywords

oxazol

ethanone

thiazol

dihydro

difluoromethyl

Prior art date

2012-06-04

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.)

Pending

Links

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• 150000001875 compounds Chemical class 0.000 claims 12
• 239000003112 inhibitor Substances 0.000 claims 11
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
• 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 7
• 239000005799 Isopyrazam Substances 0.000 claims 7
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 7
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 7
• 239000000203 mixture Substances 0.000 claims 6
• 238000000034 method Methods 0.000 claims 3
• OWKGYDDMQXIMES-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)-4,5-dihydro-1,2-oxazole Chemical compound O1CCC(C=2SC=CN=2)=N1 OWKGYDDMQXIMES-UHFFFAOYSA-N 0.000 claims 2
• -1 4- {4-[(5S) -5- ( 2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl Chemical group 0.000 claims 2
• 241000233866 Fungi Species 0.000 claims 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
• 239000011575 calcium Substances 0.000 claims 2
• 229910052791 calcium Inorganic materials 0.000 claims 2
• 235000013399 edible fruits Nutrition 0.000 claims 2
• 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 2
• 230000003032 phytopathogenic effect Effects 0.000 claims 2
• 230000035806 respiratory chain Effects 0.000 claims 2
• 150000003839 salts Chemical class 0.000 claims 2
• 239000002689 soil Substances 0.000 claims 2
• 239000011593 sulfur Substances 0.000 claims 2
• 229910052717 sulfur Inorganic materials 0.000 claims 2
• 230000009261 transgenic effect Effects 0.000 claims 2
• IAQLCKZJGNTRDO-LJQANCHMSA-N (R)-oxathiapiprolin Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-LJQANCHMSA-N 0.000 claims 1
• QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 claims 1
• IAQLCKZJGNTRDO-UHFFFAOYSA-N 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• VMEVRFWCULSSOJ-UHFFFAOYSA-N 2-[3,5-bis(difluoromethyl)pyrazol-1-yl]-1-[4-[4-[5-(2-prop-2-ynoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound N1=C(C(F)F)C=C(C(F)F)N1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2)OCC#C)CC1 VMEVRFWCULSSOJ-UHFFFAOYSA-N 0.000 claims 1
• PSGBKXSWXBIJBX-UHFFFAOYSA-N 2-[3,5-bis(difluoromethyl)pyrazol-1-yl]-1-[4-[4-[5-(3-prop-2-ynoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound N1=C(C(F)F)C=C(C(F)F)N1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C=C(OCC#C)C=CC=2)CC1 PSGBKXSWXBIJBX-UHFFFAOYSA-N 0.000 claims 1
• ICYIHUZDDUIWIT-UHFFFAOYSA-N 2-[3,5-bis(difluoromethyl)pyrazol-1-yl]-1-[4-[4-[5-(4-prop-2-ynoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound N1=C(C(F)F)C=C(C(F)F)N1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C=CC(OCC#C)=CC=2)CC1 ICYIHUZDDUIWIT-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 230000002407 ATP formation Effects 0.000 claims 1
• 239000005727 Amisulbrom Substances 0.000 claims 1
• 239000005730 Azoxystrobin Substances 0.000 claims 1
• 239000005738 Bixafen Substances 0.000 claims 1
• 239000005740 Boscalid Substances 0.000 claims 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
• 239000005747 Chlorothalonil Substances 0.000 claims 1
• JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims 1
• 239000005750 Copper hydroxide Substances 0.000 claims 1
• QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims 1
• 239000005751 Copper oxide Substances 0.000 claims 1
• 239000005752 Copper oxychloride Substances 0.000 claims 1
• 239000005761 Dimethomorph Substances 0.000 claims 1
• 102000015782 Electron Transport Complex III Human genes 0.000 claims 1
• 108010024882 Electron Transport Complex III Proteins 0.000 claims 1
• 241001522296 Erithacus rubecula Species 0.000 claims 1
• 239000005772 Famoxadone Substances 0.000 claims 1
• 239000004606 Fillers/Extenders Substances 0.000 claims 1
• 239000005780 Fluazinam Substances 0.000 claims 1
• 239000005783 Fluopyram Substances 0.000 claims 1
• 239000005784 Fluoxastrobin Substances 0.000 claims 1
• 239000005788 Fluxapyroxad Substances 0.000 claims 1
• 239000005802 Mancozeb Substances 0.000 claims 1
• 239000005807 Metalaxyl Substances 0.000 claims 1
• 239000005808 Metalaxyl-M Substances 0.000 claims 1
• 241001676573 Minium Species 0.000 claims 1
• CCCGEKHKTPTUHJ-UHFFFAOYSA-N N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC2=C1C1CCC2C1=C(Cl)Cl CCCGEKHKTPTUHJ-UHFFFAOYSA-N 0.000 claims 1
• 239000005818 Picoxystrobin Substances 0.000 claims 1
• 239000005821 Propamocarb Substances 0.000 claims 1
• MKIMSXGUTQTKJU-UHFFFAOYSA-N Propamocarb hydrochloride Chemical compound [Cl-].CCCOC(=O)NCCC[NH+](C)C MKIMSXGUTQTKJU-UHFFFAOYSA-N 0.000 claims 1
• 239000005823 Propineb Substances 0.000 claims 1
• 239000005869 Pyraclostrobin Substances 0.000 claims 1
• 239000005828 Pyrimethanil Substances 0.000 claims 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
• GRLFINVXTNXVIP-UHFFFAOYSA-N [6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl] carbamate Chemical compound Cn1nnnc1C(=NOCc1cccc(OC(N)=O)n1)c1ccccc1 GRLFINVXTNXVIP-UHFFFAOYSA-N 0.000 claims 1
• 239000002671 adjuvant Substances 0.000 claims 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
• 150000001413 amino acids Chemical class 0.000 claims 1
• BREATYVWRHIPIY-UHFFFAOYSA-N amisulbrom Chemical compound CN(C)S(=O)(=O)N1C=NC(S(=O)(=O)N2C3=CC(F)=CC=C3C(Br)=C2C)=N1 BREATYVWRHIPIY-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 230000015572 biosynthetic process Effects 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 229940118790 boscalid Drugs 0.000 claims 1
• 230000032823 cell division Effects 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 claims 1
• CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims 1
• 229910001956 copper hydroxide Inorganic materials 0.000 claims 1
• 229910000431 copper oxide Inorganic materials 0.000 claims 1
• 229910000365 copper sulfate Inorganic materials 0.000 claims 1
• ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims 1
• 230000007123 defense Effects 0.000 claims 1
• 230000008686 ergosterol biosynthesis Effects 0.000 claims 1
• 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 1
• 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 1
• 125000001153 fluoro group Chemical group F* 0.000 claims 1
• 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 1
• 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 1
• 239000000417 fungicide Substances 0.000 claims 1
• 230000001939 inductive effect Effects 0.000 claims 1
• 150000002632 lipids Chemical class 0.000 claims 1
• 230000008099 melanin synthesis Effects 0.000 claims 1
• 239000012528 membrane Substances 0.000 claims 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• 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 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• 230000011278 mitosis Effects 0.000 claims 1
• CAGKXPHIFFSYLL-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(OC)C(C)NC(=O)C1=CN(C)N=C1C(F)F CAGKXPHIFFSYLL-UHFFFAOYSA-N 0.000 claims 1
• 238000001668 nucleic acid synthesis Methods 0.000 claims 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
• IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 claims 1
• 230000004260 plant-type cell wall biogenesis Effects 0.000 claims 1
• 229920001021 polysulfide Polymers 0.000 claims 1
• 239000005077 polysulfide Substances 0.000 claims 1
• 150000008117 polysulfides Polymers 0.000 claims 1
• WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 claims 1
• KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 claims 1
• HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 claims 1
• ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 claims 1
• 230000019491 signal transduction Effects 0.000 claims 1
• IYYIUOWKEMQYNV-UHFFFAOYSA-N sodium;ethoxy-oxido-oxophosphanium Chemical compound [Na+].CCO[P+]([O-])=O IYYIUOWKEMQYNV-UHFFFAOYSA-N 0.000 claims 1
• 239000002904 solvent Substances 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 claims 1
• 239000004094 surface-active agent Substances 0.000 claims 1
• 238000003786 synthesis reaction Methods 0.000 claims 1
• 230000014616 translation Effects 0.000 claims 1
• 239000011701 zinc Substances 0.000 claims 1
• 229910052725 zinc Inorganic materials 0.000 claims 1