CA1075697A - 3-phenyl-5-substituted-4(1h)-pyridones(thiones) - Google Patents
3-phenyl-5-substituted-4(1h)-pyridones(thiones)Info
- Publication number
- CA1075697A CA1075697A CA305,980A CA305980A CA1075697A CA 1075697 A CA1075697 A CA 1075697A CA 305980 A CA305980 A CA 305980A CA 1075697 A CA1075697 A CA 1075697A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- pyridone
- phenyl
- trifluoromethylphenyl
- methylphenyl
- 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.)
- Expired
Links
- 241001061127 Thione Species 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- -1 propylthio-4(1H)-pyridone Chemical compound 0.000 claims description 20
- ADQXBMXRWFHZAZ-UHFFFAOYSA-N 1-methyl-3,5-bis(3-methylphenyl)pyridin-4-one Chemical compound CC1=CC=CC(C=2C(C(C=3C=C(C)C=CC=3)=CN(C)C=2)=O)=C1 ADQXBMXRWFHZAZ-UHFFFAOYSA-N 0.000 claims description 3
- CPSYCRJDDNLMEE-UHFFFAOYSA-N 3-(2-bromo-5-fluorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C(=CC=C(F)C=2)Br)=CN(C)C=C1C1=CC=CC=C1 CPSYCRJDDNLMEE-UHFFFAOYSA-N 0.000 claims description 3
- VUSUUQPVZIWVPB-UHFFFAOYSA-N 3-(2-bromophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C(=CC=CC=2)Br)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 VUSUUQPVZIWVPB-UHFFFAOYSA-N 0.000 claims description 3
- YDFNQQYEEUNQSN-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C(=CC(F)=CC=2)Cl)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 YDFNQQYEEUNQSN-UHFFFAOYSA-N 0.000 claims description 3
- RQLIJAVEEKLTKO-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C(=CC(F)=CC=2)Cl)=CN(C)C=C1C1=CC=CC=C1 RQLIJAVEEKLTKO-UHFFFAOYSA-N 0.000 claims description 3
- ZEPZQEHOYXDHQJ-UHFFFAOYSA-N 3-(2-methoxyphenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound COC1=CC=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 ZEPZQEHOYXDHQJ-UHFFFAOYSA-N 0.000 claims description 3
- UDECNRBAPYJGCP-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-methyl-5-(3-methylphenyl)pyridin-4-one Chemical compound CC1=CC=CC(C=2C(C(C=3C=C(Cl)C(Cl)=CC=3)=CN(C)C=2)=O)=C1 UDECNRBAPYJGCP-UHFFFAOYSA-N 0.000 claims description 3
- WJDOZPRFBWROLK-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-5-(3,4-dimethylphenyl)-1-methylpyridin-4-one Chemical compound C1=C(C)C(C)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=C(Cl)C(Cl)=C1 WJDOZPRFBWROLK-UHFFFAOYSA-N 0.000 claims description 3
- ANBYKRIWQYPJEJ-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound C1=C(C)C(C)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 ANBYKRIWQYPJEJ-UHFFFAOYSA-N 0.000 claims description 3
- JXVCBCIFPRUGJZ-UHFFFAOYSA-N 3-(3-bromo-4-methylphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound C1=C(Br)C(C)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 JXVCBCIFPRUGJZ-UHFFFAOYSA-N 0.000 claims description 3
- HHGMXGKKJIKKRL-UHFFFAOYSA-N 3-(3-bromophenyl)-1-methyl-5-(2-methylphenyl)pyridin-4-one Chemical compound CC1=CC=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC(Br)=C1 HHGMXGKKJIKKRL-UHFFFAOYSA-N 0.000 claims description 3
- LZQDBIYYJBQXBS-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-methyl-5-(2-methylphenyl)pyridin-4-one Chemical compound CC1=CC=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC(Cl)=C1 LZQDBIYYJBQXBS-UHFFFAOYSA-N 0.000 claims description 3
- UJPQYTSIRKOARI-UHFFFAOYSA-N 3-(4-bromophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=C(Br)C=C1 UJPQYTSIRKOARI-UHFFFAOYSA-N 0.000 claims description 3
- MQHBHPDZECZJOQ-UHFFFAOYSA-N 3-[2-chloro-5-(trifluoromethyl)phenyl]-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 MQHBHPDZECZJOQ-UHFFFAOYSA-N 0.000 claims description 3
- OSPYOQPKGLKIEB-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(C(Cl)=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 OSPYOQPKGLKIEB-UHFFFAOYSA-N 0.000 claims description 3
- ZBLXIJIVIVBIEG-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-5-ethoxy-1-methylpyridin-4-one Chemical compound O=C1C(OCC)=CN(C)C=C1C1=CC=C(Cl)C(C(F)(F)F)=C1 ZBLXIJIVIVBIEG-UHFFFAOYSA-N 0.000 claims description 3
- VYODLZOOLCDJRT-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-5-ethyl-1-methylpyridin-4-one Chemical compound O=C1C(CC)=CN(C)C=C1C1=CC=C(Cl)C(C(F)(F)F)=C1 VYODLZOOLCDJRT-UHFFFAOYSA-N 0.000 claims description 3
- WWIJSZOWDRDBFG-UHFFFAOYSA-N 3-ethoxy-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridine-4-thione Chemical compound S=C1C(OCC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 WWIJSZOWDRDBFG-UHFFFAOYSA-N 0.000 claims description 3
- WUHDZMNDUKCIRF-UHFFFAOYSA-N 3-ethylsulfanyl-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(SCC)=CN(C)C=C1C1=CC=CC=C1 WUHDZMNDUKCIRF-UHFFFAOYSA-N 0.000 claims description 3
- RXGJTLBOHFPKIJ-UHFFFAOYSA-N 3-ethylsulfinyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(S(=O)CC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 RXGJTLBOHFPKIJ-UHFFFAOYSA-N 0.000 claims description 3
- FJXXEHJYKAQACI-UHFFFAOYSA-N 3-methoxy-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(OC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 FJXXEHJYKAQACI-UHFFFAOYSA-N 0.000 claims description 3
- KTXPHXSEKIXRHS-UHFFFAOYSA-N 3-tert-butylsulfanyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CN1C=C(SC(C)(C)C)C(=O)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 KTXPHXSEKIXRHS-UHFFFAOYSA-N 0.000 claims description 3
- LSCADUVZHBDNDQ-UHFFFAOYSA-N 1-methyl-3-(2-methyl-5-nitrophenyl)-5-phenylpyridin-4-one Chemical compound CC1=CC=C([N+]([O-])=O)C=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 LSCADUVZHBDNDQ-UHFFFAOYSA-N 0.000 claims description 2
- PVHYDAMTVRNMLN-UHFFFAOYSA-N 1-methyl-3-(2-methylprop-2-enylsulfanyl)-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CN1C=C(C(C(=C1)C1=CC(=CC=C1)C(F)(F)F)=O)SCC(=C)C PVHYDAMTVRNMLN-UHFFFAOYSA-N 0.000 claims description 2
- BVTWGIRMMJIIDA-UHFFFAOYSA-N 1-methyl-3-(2-methylpropylsulfanyl)-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(SCC(C)C)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 BVTWGIRMMJIIDA-UHFFFAOYSA-N 0.000 claims description 2
- YGXHMSGOWXBHJP-UHFFFAOYSA-N 1-methyl-3-methylsulfanyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(SC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 YGXHMSGOWXBHJP-UHFFFAOYSA-N 0.000 claims description 2
- YFRWLIMGZKMSLL-UHFFFAOYSA-N 1-methyl-3-propan-2-yloxy-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(OC(C)C)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 YFRWLIMGZKMSLL-UHFFFAOYSA-N 0.000 claims description 2
- LVWMUEHLPPAIRJ-UHFFFAOYSA-N 3,5-bis(3,5-dichlorophenyl)-1-methylpyridin-4-one Chemical compound O=C1C(C=2C=C(Cl)C=C(Cl)C=2)=CN(C)C=C1C1=CC(Cl)=CC(Cl)=C1 LVWMUEHLPPAIRJ-UHFFFAOYSA-N 0.000 claims description 2
- XWDHZBMZZGGMKI-UHFFFAOYSA-N 3-(1-methyl-4-oxo-5-phenylpyridin-3-yl)benzoic acid Chemical compound O=C1C(C=2C=C(C=CC=2)C(O)=O)=CN(C)C=C1C1=CC=CC=C1 XWDHZBMZZGGMKI-UHFFFAOYSA-N 0.000 claims description 2
- QIYCFIVWINMHEB-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C(=CC=CC=2Cl)Cl)=CN(C)C=C1C1=CC=CC=C1 QIYCFIVWINMHEB-UHFFFAOYSA-N 0.000 claims description 2
- KFGRUVDEMASZSL-UHFFFAOYSA-N 3-(2-hydroxypropyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound OC(CC1=CN(C=C(C1=O)C1=CC(=CC=C1)C(F)(F)F)C)C KFGRUVDEMASZSL-UHFFFAOYSA-N 0.000 claims description 2
- UXMVRFNURBAMQM-UHFFFAOYSA-N 3-(3,5-dimethylphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound CC1=CC(C)=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 UXMVRFNURBAMQM-UHFFFAOYSA-N 0.000 claims description 2
- DLLHXQIRBHMLRZ-UHFFFAOYSA-N 3-(3-bromo-4-methylphenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound C1=C(Br)C(C)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 DLLHXQIRBHMLRZ-UHFFFAOYSA-N 0.000 claims description 2
- YIKCZGOLVIJOSE-UHFFFAOYSA-N 3-(3-butylphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound CCCCC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 YIKCZGOLVIJOSE-UHFFFAOYSA-N 0.000 claims description 2
- FCFDJFGLLZGCJU-UHFFFAOYSA-N 3-(3-iodophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC(I)=C1 FCFDJFGLLZGCJU-UHFFFAOYSA-N 0.000 claims description 2
- DKXGXYDYISDUJN-UHFFFAOYSA-N 3-(4-bromophenyl)-1-methyl-5-(3-methylphenyl)pyridin-4-one Chemical compound CC1=CC=CC(C=2C(C(C=3C=CC(Br)=CC=3)=CN(C)C=2)=O)=C1 DKXGXYDYISDUJN-UHFFFAOYSA-N 0.000 claims description 2
- PFHOINPYJMFSHA-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=C(O)C=C1 PFHOINPYJMFSHA-UHFFFAOYSA-N 0.000 claims description 2
- WKWTWJRJHAXOKS-UHFFFAOYSA-N 3-(5-bromo-2-fluorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C(=CC=C(Br)C=2)F)=CN(C)C=C1C1=CC=CC=C1 WKWTWJRJHAXOKS-UHFFFAOYSA-N 0.000 claims description 2
- PSESGFASJZSNPK-UHFFFAOYSA-N 3-(5-fluoro-2-iodophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C(=CC=C(F)C=2)I)=CN(C)C=C1C1=CC=CC=C1 PSESGFASJZSNPK-UHFFFAOYSA-N 0.000 claims description 2
- OKPZCDJLJVZSGD-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-1-methyl-5-thiophen-2-ylpyridin-4-one Chemical compound O=C1C(C=2C=C(C(Cl)=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CS1 OKPZCDJLJVZSGD-UHFFFAOYSA-N 0.000 claims description 2
- MEJIZPJXNFVKRN-UHFFFAOYSA-N 3-[5-(4-bromophenyl)-1-methyl-4-oxopyridin-3-yl]benzoic acid Chemical compound O=C1C(C=2C=C(C=CC=2)C(O)=O)=CN(C)C=C1C1=CC=C(Br)C=C1 MEJIZPJXNFVKRN-UHFFFAOYSA-N 0.000 claims description 2
- BHUVIGDARDZYBX-UHFFFAOYSA-N 3-butan-2-ylsulfanyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(SC(C)CC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 BHUVIGDARDZYBX-UHFFFAOYSA-N 0.000 claims description 2
- UTGZMOBPWKRIRD-UHFFFAOYSA-N 3-ethyl-1-hydroxy-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound C(C)C1=CN(C=C(C1=O)C1=CC(=CC=C1)C(F)(F)F)O UTGZMOBPWKRIRD-UHFFFAOYSA-N 0.000 claims description 2
- FJSVUDOFDZQJLK-UHFFFAOYSA-N 3-ethyl-5-(3-methoxyphenyl)-1-methylpyridin-4-one Chemical compound O=C1C(CC)=CN(C)C=C1C1=CC=CC(OC)=C1 FJSVUDOFDZQJLK-UHFFFAOYSA-N 0.000 claims description 2
- QYPIXOUNZMGSPN-UHFFFAOYSA-N 3-ethylsulfanyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridine-4-thione Chemical compound S=C1C(SCC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 QYPIXOUNZMGSPN-UHFFFAOYSA-N 0.000 claims description 2
- JFACACRTOHUIJN-UHFFFAOYSA-N 5-(2,5-dimethoxyphenyl)-1-methyl-4-oxopyridine-3-carbonitrile Chemical compound COC1=CC=C(OC)C(C=2C(C(C#N)=CN(C)C=2)=O)=C1 JFACACRTOHUIJN-UHFFFAOYSA-N 0.000 claims description 2
- LREAIMREKYLQHA-UHFFFAOYSA-N ethyl 1-methyl-4-oxo-5-[3-(trifluoromethyl)phenyl]pyridine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 LREAIMREKYLQHA-UHFFFAOYSA-N 0.000 claims description 2
- JYRCAWKOBDYVHA-UHFFFAOYSA-N ethyl 1-methyl-4-oxo-5-phenylpyridine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)=CN(C)C=C1C1=CC=CC=C1 JYRCAWKOBDYVHA-UHFFFAOYSA-N 0.000 claims description 2
- IILVJUUUQGCNHC-UHFFFAOYSA-N methyl 3-[1-methyl-5-(4-methylphenyl)-4-oxopyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C(C(C=3C=CC(C)=CC=3)=CN(C)C=2)=O)=C1 IILVJUUUQGCNHC-UHFFFAOYSA-N 0.000 claims description 2
- HBHMIWZJYDCYAX-UHFFFAOYSA-N 1,3-diethyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(CC)=CN(CC)C=C1C1=CC=CC(C(F)(F)F)=C1 HBHMIWZJYDCYAX-UHFFFAOYSA-N 0.000 claims 2
- GUTSDNKJOBEZPP-UHFFFAOYSA-N 1-ethyl-3,5-bis[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(CC)C=C1C1=CC=CC(C(F)(F)F)=C1 GUTSDNKJOBEZPP-UHFFFAOYSA-N 0.000 claims 2
- QOYMDVZODDSWDA-UHFFFAOYSA-N 1-methyl-3-(2-methylphenyl)-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CC1=CC=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 QOYMDVZODDSWDA-UHFFFAOYSA-N 0.000 claims 2
- HNASGVMMKOVJEJ-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CC1=CC=CC(C=2C(C(C=3C=C(C=CC=3)C(F)(F)F)=CN(C)C=2)=O)=C1 HNASGVMMKOVJEJ-UHFFFAOYSA-N 0.000 claims 2
- SBDOCCCTNKSHTC-UHFFFAOYSA-N 1-methyl-3-[2-(trifluoromethyl)phenyl]-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C(=CC=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 SBDOCCCTNKSHTC-UHFFFAOYSA-N 0.000 claims 2
- VJRIXDIYCWJUSG-UHFFFAOYSA-N 1-methyl-3-[3-(trifluoromethyl)phenyl]-5-(trifluoromethylsulfanyl)pyridin-4-one Chemical compound CN1C=C(SC(F)(F)F)C(=O)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 VJRIXDIYCWJUSG-UHFFFAOYSA-N 0.000 claims 2
- DJZUELVYQFBCQV-UHFFFAOYSA-N 1-methyl-3-[3-(trifluoromethyl)phenyl]-5-[3-(trifluoromethylsulfanyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC(SC(F)(F)F)=C1 DJZUELVYQFBCQV-UHFFFAOYSA-N 0.000 claims 2
- IFKAIWRSFKDBLQ-UHFFFAOYSA-N 1-methyl-3-phenoxy-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1OC1=CC=CC=C1 IFKAIWRSFKDBLQ-UHFFFAOYSA-N 0.000 claims 2
- UJGIVLUARJLMDC-UHFFFAOYSA-N 1-methyl-3-propan-2-ylsulfanyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(SC(C)C)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 UJGIVLUARJLMDC-UHFFFAOYSA-N 0.000 claims 2
- QXIPCVZWIYWEEP-UHFFFAOYSA-N 1-methyl-3-propylsulfanyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(SCCC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 QXIPCVZWIYWEEP-UHFFFAOYSA-N 0.000 claims 2
- PIGVXHSMBYPWHH-UHFFFAOYSA-N 3-(1-hydroxyethyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound OC(C)C1=CN(C=C(C1=O)C1=CC(=CC=C1)C(F)(F)F)C PIGVXHSMBYPWHH-UHFFFAOYSA-N 0.000 claims 2
- JRWOQCCEZSXGEL-UHFFFAOYSA-N 3-(2-ethylphenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CCC1=CC=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 JRWOQCCEZSXGEL-UHFFFAOYSA-N 0.000 claims 2
- WDVRXTMUHHKVKF-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-1-methyl-5-propan-2-ylpyridin-4-one Chemical compound O=C1C(C(C)C)=CN(C)C=C1C1=CC=C(Cl)C(C(F)(F)F)=C1 WDVRXTMUHHKVKF-UHFFFAOYSA-N 0.000 claims 2
- RSUUQCLUXRFJPU-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-1-methyl-5-propylpyridin-4-one Chemical compound O=C1C(CCC)=CN(C)C=C1C1=CC=C(Cl)C(C(F)(F)F)=C1 RSUUQCLUXRFJPU-UHFFFAOYSA-N 0.000 claims 2
- ZUOBJEZINDUQCJ-UHFFFAOYSA-N 3-ethoxy-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(OCC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 ZUOBJEZINDUQCJ-UHFFFAOYSA-N 0.000 claims 2
- NPPHIEHTKJAYSL-UHFFFAOYSA-N 1-hydroxy-3-phenyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound ON1C=C(C(C(=C1)C1=CC(=CC=C1)C(F)(F)F)=O)C1=CC=CC=C1 NPPHIEHTKJAYSL-UHFFFAOYSA-N 0.000 claims 1
- LKKJQHHZMHXZQZ-UHFFFAOYSA-N 1-methyl-3,5-bis(4-methylphenyl)pyridin-4-one Chemical compound C1=CC(C)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=C(C)C=C1 LKKJQHHZMHXZQZ-UHFFFAOYSA-N 0.000 claims 1
- DOWJIZDWBUSYHL-UHFFFAOYSA-N 1-methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CN1C=C(OCC(F)(F)F)C(=O)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 DOWJIZDWBUSYHL-UHFFFAOYSA-N 0.000 claims 1
- KFJJVZWHNWJYLJ-UHFFFAOYSA-N 1-methyl-3-(2-methylphenyl)-5-(4-methylphenyl)pyridin-4-one Chemical compound C1=CC(C)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1C KFJJVZWHNWJYLJ-UHFFFAOYSA-N 0.000 claims 1
- DLJVPHFTTVREKE-UHFFFAOYSA-N 1-methyl-3-(2-methylphenyl)-5-[3-(trifluoromethyl)phenyl]pyridine-4-thione Chemical compound CC1=CC=CC=C1C(C1=S)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 DLJVPHFTTVREKE-UHFFFAOYSA-N 0.000 claims 1
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- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HHTOWVWIVBSOKC-UHFFFAOYSA-N cis,trans-5'-hydroxythalidomide Chemical compound O=C1NC(=O)C(O)CC1N1C(=O)C2=CC=CC=C2C1=O HHTOWVWIVBSOKC-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 101150075361 cps3 gene Proteins 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- HNPCDFJZADHNHD-UHFFFAOYSA-N n-(diformamidomethyl)formamide Chemical class O=CNC(NC=O)NC=O HNPCDFJZADHNHD-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/810,219 US4152136A (en) | 1974-08-28 | 1977-06-27 | 3-Phenyl-5-substituted-4(1H)-pyridones(thiones) |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1075697A true CA1075697A (en) | 1980-04-15 |
Family
ID=25203294
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA305,980A Expired CA1075697A (en) | 1977-06-27 | 1978-06-22 | 3-phenyl-5-substituted-4(1h)-pyridones(thiones) |
Country Status (16)
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4714492A (en) * | 1980-05-12 | 1987-12-22 | Rohm And Haas Company | Certain 2-phenyl-4-oxo-nicotinates and their use for inducing male sterility in a cereal grain plant |
ZA813029B (en) * | 1980-05-12 | 1982-05-26 | Rohm & Haas | Novel substituted oxonicotinates,their use as plant growth regulators and plant growth regulating compositions containing them |
US4936904A (en) * | 1980-05-12 | 1990-06-26 | Carlson Glenn R | Aryl-4-oxonicotinates useful for inducing male sterility in cereal grain plants |
EP0067511A3 (en) * | 1981-05-19 | 1983-04-06 | Imperial Chemical Industries Plc | Method of inducing tillering using pyridine derivatives, and some of the pyridines themselves, process for preparing them and agricultural compositions containing them |
DE3531773A1 (de) * | 1985-09-06 | 1987-03-19 | Bayer Ag | 3,5 disubstituierte 4-pyridone |
US5403934A (en) * | 1990-03-12 | 1995-04-04 | Burroughs Wellcome Co. | Heterocyclic compounds |
GB9005518D0 (en) * | 1990-03-12 | 1990-05-09 | Wellcome Found | Heterocyclic compounds |
US5567698A (en) * | 1995-02-15 | 1996-10-22 | Bristol-Myers Squibb Company | Pyridinium thiomethyl substituted chepholosporin derivatives |
WO2023232673A1 (en) * | 2022-06-01 | 2023-12-07 | Syngenta Crop Protection Ag | Herbicidal derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ178426A (en) * | 1974-08-28 | 1978-06-20 | Lilly Co Eli | 3-phenyl-1-substituted-4(1h)-pyridones or-pyridine-thionesand herbicidal compositions |
-
1975
- 1975-08-27 AT AT563277A patent/AT362613B/de not_active IP Right Cessation
-
1978
- 1978-03-31 MW MW17/78A patent/MW1778A1/xx unknown
- 1978-05-25 IN IN567/CAL/78A patent/IN149651B/en unknown
- 1978-06-21 RO RO7894426A patent/RO75145A/ro unknown
- 1978-06-21 RO RO78102053A patent/RO80037A/ro unknown
- 1978-06-21 RO RO78102054A patent/RO80699A/ro unknown
- 1978-06-22 ZM ZM58/78A patent/ZM5878A1/xx unknown
- 1978-06-22 FR FR7818746A patent/FR2395996A2/fr active Granted
- 1978-06-22 CA CA305,980A patent/CA1075697A/en not_active Expired
- 1978-06-23 BE BE1008944A patent/BE868393A/xx not_active IP Right Cessation
- 1978-06-24 GR GR56592A patent/GR70237B/el unknown
- 1978-06-26 GT GT197852905A patent/GT197852905A/es unknown
- 1978-06-26 IE IE1265/78A patent/IE47202B1/en unknown
- 1978-06-26 ZA ZA783650A patent/ZA783650B/xx unknown
- 1978-06-26 LU LU79873A patent/LU79873A1/xx unknown
- 1978-06-26 IT IT24972/78A patent/IT1113145B/it active
- 1978-06-27 BG BG040220A patent/BG29870A3/xx unknown
- 1978-06-27 BG BG041632A patent/BG30176A4/xx unknown
- 1978-06-27 BG BG041633A patent/BG30168A4/xx unknown
- 1978-06-27 BG BG041631A patent/BG30175A4/xx unknown
- 1978-09-01 GB GB7835305A patent/GB2029403B/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BG30168A4 (en) | 1981-04-15 |
IT1113145B (it) | 1986-01-20 |
GT197852905A (es) | 1979-12-18 |
RO75145A (ro) | 1981-01-30 |
GB2029403A (en) | 1980-03-19 |
GB2029403B (en) | 1982-10-27 |
ZA783650B (en) | 1980-02-27 |
ZM5878A1 (en) | 1979-04-23 |
RO80037A (ro) | 1982-10-26 |
BG30176A4 (en) | 1981-04-15 |
MW1778A1 (en) | 1979-05-09 |
FR2395996B2 (enrdf_load_stackoverflow) | 1983-08-05 |
ATA563277A (de) | 1980-10-15 |
BG29870A3 (en) | 1981-02-16 |
GR70237B (enrdf_load_stackoverflow) | 1982-09-01 |
LU79873A1 (enrdf_load_stackoverflow) | 1978-12-07 |
BG30175A4 (en) | 1981-04-15 |
IE781265L (en) | 1978-12-27 |
RO80699A (ro) | 1982-12-06 |
AT362613B (de) | 1981-06-10 |
IT7824972A0 (it) | 1978-06-26 |
IN149651B (enrdf_load_stackoverflow) | 1982-03-06 |
FR2395996A2 (fr) | 1979-01-26 |
IE47202B1 (en) | 1984-01-11 |
BE868393A (fr) | 1978-12-27 |
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