CA1075696A - 3-phenyl-5-substituted-4(1h)-pyridones-(thiones) - Google Patents
3-phenyl-5-substituted-4(1h)-pyridones-(thiones)Info
- Publication number
- CA1075696A CA1075696A CA233,945A CA233945A CA1075696A CA 1075696 A CA1075696 A CA 1075696A CA 233945 A CA233945 A CA 233945A CA 1075696 A CA1075696 A CA 1075696A
- Authority
- CA
- Canada
- Prior art keywords
- pyridone
- phenyl
- methyl
- halo
- alkyl
- 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 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 262
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 160
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- -1 cyano, carboxy Chemical group 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 61
- 125000001475 halogen functional group Chemical group 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
- 229910052717 sulfur Chemical group 0.000 claims description 11
- 239000011593 sulfur Chemical group 0.000 claims description 11
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
- 230000002152 alkylating effect Effects 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- LZQWXHXEBCOWNT-UHFFFAOYSA-N 1-methyl-3,5-diphenylpyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(C)C=C1C1=CC=CC=C1 LZQWXHXEBCOWNT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- JLPJUTBNKUKCTC-UHFFFAOYSA-N 1-methyl-3-phenylpyridin-4-one Chemical compound CN1C=CC(=O)C(C=2C=CC=CC=2)=C1 JLPJUTBNKUKCTC-UHFFFAOYSA-N 0.000 claims description 3
- FMKVJFMYKQKHRA-UHFFFAOYSA-N 3,5-bis(3-chlorophenyl)-1-methylpyridin-4-one Chemical compound O=C1C(C=2C=C(Cl)C=CC=2)=CN(C)C=C1C1=CC=CC(Cl)=C1 FMKVJFMYKQKHRA-UHFFFAOYSA-N 0.000 claims description 3
- YAFTYUDWIFJZJP-UHFFFAOYSA-N 3,5-bis(3-fluorophenyl)-1-methylpyridin-4-one Chemical compound O=C1C(C=2C=C(F)C=CC=2)=CN(C)C=C1C1=CC=CC(F)=C1 YAFTYUDWIFJZJP-UHFFFAOYSA-N 0.000 claims description 3
- FNQAFOVJGCHDEM-UHFFFAOYSA-N 3-(3-ethoxyphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound CCOC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 FNQAFOVJGCHDEM-UHFFFAOYSA-N 0.000 claims description 3
- MQBRCRADEZDHHH-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(O)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 MQBRCRADEZDHHH-UHFFFAOYSA-N 0.000 claims description 3
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 230000001473 noxious effect Effects 0.000 claims description 3
- VUCOOHFGXBBVGC-UHFFFAOYSA-N 1,3-dimethyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 VUCOOHFGXBBVGC-UHFFFAOYSA-N 0.000 claims description 2
- OUNWYVVLDFECCQ-UHFFFAOYSA-N 1,3-dimethyl-5-phenylpyridin-4-one Chemical compound O=C1C(C)=CN(C)C=C1C1=CC=CC=C1 OUNWYVVLDFECCQ-UHFFFAOYSA-N 0.000 claims description 2
- YHAXFLHORZBWCZ-UHFFFAOYSA-N 1-ethyl-3,5-diphenylpyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(CC)C=C1C1=CC=CC=C1 YHAXFLHORZBWCZ-UHFFFAOYSA-N 0.000 claims description 2
- BJSOXSBKLWIJHR-UHFFFAOYSA-N 1-methoxy-3,5-diphenylpyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(OC)C=C1C1=CC=CC=C1 BJSOXSBKLWIJHR-UHFFFAOYSA-N 0.000 claims description 2
- WCPKPTIZAQAYLU-UHFFFAOYSA-N 1-methyl-3,5-diphenylpyridine-4-thione Chemical compound S=C1C(C=2C=CC=CC=2)=CN(C)C=C1C1=CC=CC=C1 WCPKPTIZAQAYLU-UHFFFAOYSA-N 0.000 claims description 2
- KEEWEGOVOWRAPW-UHFFFAOYSA-N 1-methyl-3-(3-methylsulfanylphenyl)-5-phenylpyridin-4-one Chemical compound CSC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 KEEWEGOVOWRAPW-UHFFFAOYSA-N 0.000 claims description 2
- ASJJPJQACIYAOB-UHFFFAOYSA-N 1-methyl-3-phenoxy-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(C)C=C1OC1=CC=CC=C1 ASJJPJQACIYAOB-UHFFFAOYSA-N 0.000 claims description 2
- WNFQVYWKHPEKFJ-UHFFFAOYSA-N 1-methyl-3-phenyl-5-(3-phenylmethoxyphenyl)pyridin-4-one Chemical compound O=C1C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 WNFQVYWKHPEKFJ-UHFFFAOYSA-N 0.000 claims description 2
- KALGMRMJLBYJOT-UHFFFAOYSA-N 1-methyl-3-phenyl-5-(3-phenylphenyl)pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C=2C=CC=CC=2)=CN(C)C=C1C1=CC=CC=C1 KALGMRMJLBYJOT-UHFFFAOYSA-N 0.000 claims description 2
- BFVBEBPEOKKCOE-UHFFFAOYSA-N 1-methyl-3-phenyl-5-(3-propan-2-yloxyphenyl)pyridin-4-one Chemical compound CC(C)OC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 BFVBEBPEOKKCOE-UHFFFAOYSA-N 0.000 claims description 2
- DNVBKAXQOJQGDY-UHFFFAOYSA-N 1-methyl-3-phenyl-5-(3-propoxyphenyl)pyridin-4-one Chemical compound CCCOC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 DNVBKAXQOJQGDY-UHFFFAOYSA-N 0.000 claims description 2
- VZMJINAOKCEPAN-UHFFFAOYSA-N 1-methyl-3-propan-2-yl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C(C)C)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 VZMJINAOKCEPAN-UHFFFAOYSA-N 0.000 claims description 2
- NKYUFELENRTQSR-UHFFFAOYSA-N 1-methyl-4-oxo-5-[3-(trifluoromethyl)phenyl]pyridine-3-carbonitrile Chemical compound CN1C=C(C#N)C(=O)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 NKYUFELENRTQSR-UHFFFAOYSA-N 0.000 claims description 2
- XJBGZFXSEZOUGV-UHFFFAOYSA-N 1-methyl-4-oxo-5-phenylpyridine-3-carbonitrile Chemical compound CN1C=C(C#N)C(=O)C(C=2C=CC=CC=2)=C1 XJBGZFXSEZOUGV-UHFFFAOYSA-N 0.000 claims description 2
- XFCIAFOVJQVPLB-UHFFFAOYSA-N 2-[3-(1-methyl-4-oxo-5-phenylpyridin-3-yl)phenoxy]acetonitrile Chemical compound O=C1C(C=2C=C(OCC#N)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 XFCIAFOVJQVPLB-UHFFFAOYSA-N 0.000 claims description 2
- KRLZDKGJNOXHNY-UHFFFAOYSA-N 3,5-bis(3,4-dimethoxyphenyl)-1-methylpyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=C(OC)C(OC)=C1 KRLZDKGJNOXHNY-UHFFFAOYSA-N 0.000 claims description 2
- ZOALBZUDZKFEEC-UHFFFAOYSA-N 3,5-bis(3-bromophenyl)-1-methylpyridin-4-one Chemical compound O=C1C(C=2C=C(Br)C=CC=2)=CN(C)C=C1C1=CC=CC(Br)=C1 ZOALBZUDZKFEEC-UHFFFAOYSA-N 0.000 claims description 2
- GATKNVWDUBJPFQ-UHFFFAOYSA-N 3,5-bis(3-chlorophenyl)-1-methylpyridine-4-thione Chemical compound S=C1C(C=2C=C(Cl)C=CC=2)=CN(C)C=C1C1=CC=CC(Cl)=C1 GATKNVWDUBJPFQ-UHFFFAOYSA-N 0.000 claims description 2
- DWWFABVQLMOKDT-UHFFFAOYSA-N 3,5-diphenyl-1-propylpyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(CCC)C=C1C1=CC=CC=C1 DWWFABVQLMOKDT-UHFFFAOYSA-N 0.000 claims description 2
- DLELCFFLQFMLKG-UHFFFAOYSA-N 3-(1-methyl-4-oxo-5-phenylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C=C(C=CC=2)C#N)=CN(C)C=C1C1=CC=CC=C1 DLELCFFLQFMLKG-UHFFFAOYSA-N 0.000 claims description 2
- GDCAIRWUPXXDIU-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C(=CC=CC=2)F)=CN(C)C=C1C1=CC=CC=C1 GDCAIRWUPXXDIU-UHFFFAOYSA-N 0.000 claims description 2
- GEHCOIVJDFDXCA-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(Cl)C(Cl)=CC=2)=CN(C)C=C1C1=CC=CC=C1 GEHCOIVJDFDXCA-UHFFFAOYSA-N 0.000 claims description 2
- BAWASURVNVQPNT-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(Cl)C=C(Cl)C=2)=CN(C)C=C1C1=CC=CC=C1 BAWASURVNVQPNT-UHFFFAOYSA-N 0.000 claims description 2
- XDMRNCUFUOAHJN-UHFFFAOYSA-N 3-(3-bromophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(Br)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 XDMRNCUFUOAHJN-UHFFFAOYSA-N 0.000 claims description 2
- BJYNRIBROOCBAX-UHFFFAOYSA-N 3-(3-chlorophenyl)-1,5-dimethylpyridin-4-one Chemical compound O=C1C(C)=CN(C)C=C1C1=CC=CC(Cl)=C1 BJYNRIBROOCBAX-UHFFFAOYSA-N 0.000 claims description 2
- VGSSXFWMRBTFGW-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(Cl)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 VGSSXFWMRBTFGW-UHFFFAOYSA-N 0.000 claims description 2
- AIILUKTUHGOXHZ-UHFFFAOYSA-N 3-(3-decoxyphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound CCCCCCCCCCOC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 AIILUKTUHGOXHZ-UHFFFAOYSA-N 0.000 claims description 2
- LUWXLAOSPYKDPD-UHFFFAOYSA-N 3-(3-ethylphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound CCC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 LUWXLAOSPYKDPD-UHFFFAOYSA-N 0.000 claims description 2
- PBCKBDGKCVYFID-UHFFFAOYSA-N 3-(3-fluorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(F)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 PBCKBDGKCVYFID-UHFFFAOYSA-N 0.000 claims description 2
- YEARPEVMUDEHHJ-UHFFFAOYSA-N 3-(3-hexoxyphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound CCCCCCOC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 YEARPEVMUDEHHJ-UHFFFAOYSA-N 0.000 claims description 2
- VRHTXALAVNMBQS-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound COC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 VRHTXALAVNMBQS-UHFFFAOYSA-N 0.000 claims description 2
- GJYOKNJWSIARGN-UHFFFAOYSA-N 3-(4-ethylphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound C1=CC(CC)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 GJYOKNJWSIARGN-UHFFFAOYSA-N 0.000 claims description 2
- DCLVJYXYVHIEOX-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=CC(F)=CC=2)=CN(C)C=C1C1=CC=CC=C1 DCLVJYXYVHIEOX-UHFFFAOYSA-N 0.000 claims description 2
- IISFJGVSBQHFMY-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound C1=CC(OC)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 IISFJGVSBQHFMY-UHFFFAOYSA-N 0.000 claims description 2
- DBPYIEYLVWVKQU-UHFFFAOYSA-N 3-(furan-2-yl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(C)C=C1C1=CC=CO1 DBPYIEYLVWVKQU-UHFFFAOYSA-N 0.000 claims description 2
- GKTYNDMWRHSQRS-UHFFFAOYSA-N 3-[3-(cyclohexylmethoxy)phenyl]-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(OCC3CCCCC3)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 GKTYNDMWRHSQRS-UHFFFAOYSA-N 0.000 claims description 2
- RWHPEPHIFSBMSU-UHFFFAOYSA-N 3-[3-(cyclohexylmethyl)phenyl]-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(CC3CCCCC3)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 RWHPEPHIFSBMSU-UHFFFAOYSA-N 0.000 claims description 2
- SHQGRYNRHBVIBZ-UHFFFAOYSA-N 3-chloro-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CN1C=C(Cl)C(=O)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 SHQGRYNRHBVIBZ-UHFFFAOYSA-N 0.000 claims description 2
- UORXULCUDVCPID-UHFFFAOYSA-N 3-cyclohexyl-5-(3-hydroxyphenyl)-1-methylpyridin-4-one Chemical compound O=C1C(C=2C=C(O)C=CC=2)=CN(C)C=C1C1CCCCC1 UORXULCUDVCPID-UHFFFAOYSA-N 0.000 claims description 2
- FYKWBGLIFZIRGF-UHFFFAOYSA-N 3-ethyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(CC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 FYKWBGLIFZIRGF-UHFFFAOYSA-N 0.000 claims description 2
- CWSFNHNDGDHJSH-UHFFFAOYSA-N 3-methoxy-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(OC)=CN(C)C=C1C1=CC=CC=C1 CWSFNHNDGDHJSH-UHFFFAOYSA-N 0.000 claims description 2
- VQLBXEGLWJBKNP-UHFFFAOYSA-N 3-phenyl-1-propyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(CCC)C=C1C1=CC=CC=C1 VQLBXEGLWJBKNP-UHFFFAOYSA-N 0.000 claims description 2
- YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 16
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- PIMZJOMHOCTTIH-UHFFFAOYSA-N (4-oxo-3,5-diphenylpyridin-1-yl) acetate Chemical compound O=C1C(C=2C=CC=CC=2)=CN(OC(=O)C)C=C1C1=CC=CC=C1 PIMZJOMHOCTTIH-UHFFFAOYSA-N 0.000 claims 1
- RLCAUJHSDBSXLB-UHFFFAOYSA-N 1-(dimethylamino)-3,5-diphenylpyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(N(C)C)C=C1C1=CC=CC=C1 RLCAUJHSDBSXLB-UHFFFAOYSA-N 0.000 claims 1
- WBUMGFVLCKFELD-UHFFFAOYSA-N 1-ethyl-3-phenyl-5-[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=C1 WBUMGFVLCKFELD-UHFFFAOYSA-N 0.000 claims 1
- UYQYJQGFVUSHQS-UHFFFAOYSA-N 1-methoxy-3-phenyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(OC)C=C1C1=CC=CC=C1 UYQYJQGFVUSHQS-UHFFFAOYSA-N 0.000 claims 1
- PZBXEGSLTCUVJO-UHFFFAOYSA-N 1-methyl-3,5-bis[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(C(F)(F)F)=C1 PZBXEGSLTCUVJO-UHFFFAOYSA-N 0.000 claims 1
- VAQXEKOOZVVGDQ-UHFFFAOYSA-N 1-methyl-3-(2-methylphenyl)-5-phenylpyridin-4-one Chemical compound CC1=CC=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 VAQXEKOOZVVGDQ-UHFFFAOYSA-N 0.000 claims 1
- NVWXNJCQVUGHGO-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)-5-phenylpyridin-4-one Chemical compound CC1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 NVWXNJCQVUGHGO-UHFFFAOYSA-N 0.000 claims 1
- XJXZWVLPPDGJLX-UHFFFAOYSA-N 1-methyl-3-(3-methylsulfinylphenyl)-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)S(C)=O)=CN(C)C=C1C1=CC=CC=C1 XJXZWVLPPDGJLX-UHFFFAOYSA-N 0.000 claims 1
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- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
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- 230000005494 condensation Effects 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 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
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- LSGHIKKUGSTMPE-UHFFFAOYSA-N methyl 2-[3-(3-acetyloxyphenyl)-5-[2-(7-cyanoheptylsulfinyl)phenyl]-4-oxopyridin-1-yl]acetate Chemical compound O=C1C(C=2C(=CC=CC=2)S(=O)CCCCCCCC#N)=CN(CC(=O)OC)C=C1C1=CC=CC(OC(C)=O)=C1 LSGHIKKUGSTMPE-UHFFFAOYSA-N 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000005416 organic matter Substances 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
- JUKHVNMXKSHNQY-UHFFFAOYSA-N penta-3,4-dien-2-one Chemical compound CC(=O)C=C=C JUKHVNMXKSHNQY-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
- ZONDRDMYXWIZJA-UHFFFAOYSA-N propyl 1-(2-cyanoethyl)-5-(4-methyl-3-octylphenyl)-4-oxopyridine-3-carboxylate Chemical compound C1=C(C)C(CCCCCCCC)=CC(C=2C(C(C(=O)OCCC)=CN(CCC#N)C=2)=O)=C1 ZONDRDMYXWIZJA-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/233—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C49/235—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the aromatic 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
- C07D213/61—Halogen atoms or nitro radicals
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US50142474A | 1974-08-28 | 1974-08-28 | |
US59166175A | 1975-07-03 | 1975-07-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1075696A true CA1075696A (en) | 1980-04-15 |
Family
ID=27053808
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA233,945A Expired CA1075696A (en) | 1974-08-28 | 1975-08-22 | 3-phenyl-5-substituted-4(1h)-pyridones-(thiones) |
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US20160286802A1 (en) * | 2013-04-17 | 2016-10-06 | Sepro Corporation | Herbicidal compositions and methods |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT362613B (de) * | 1975-08-27 | 1981-06-10 | Lilly Co Eli | Herbizides mittel |
US4051142A (en) * | 1976-05-24 | 1977-09-27 | Rohm And Haas Company | 1-Aryl-4-pyridones |
US4174209A (en) * | 1978-06-19 | 1979-11-13 | Eli Lilly And Company | Herbicidal 1-alkyl-3-phenylpyridinium salts |
ATE17482T1 (de) * | 1981-09-05 | 1986-02-15 | Bayer Ag | Hetero-substituierte 4-pyridon-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide. |
AU570466B2 (en) * | 1983-06-17 | 1988-03-17 | Rhone-Poulenc Agro | 3-oxo-2,3-dihydrofuran derivatives |
US4537623A (en) * | 1984-03-29 | 1985-08-27 | Chevron Research Company | Herbicidal 2-(oxa or thia heterocycle)5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofurans |
US4568376A (en) * | 1984-05-09 | 1986-02-04 | Chevron Research Company | Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran and derivatives thereof |
US4596595A (en) * | 1984-06-22 | 1986-06-24 | Chevron Research Company | Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrothiophene and derivatives thereof |
DE3430232A1 (de) * | 1984-08-17 | 1986-02-27 | Bayer Ag, 5090 Leverkusen | N-methyl-4-pyridone |
US4606756A (en) * | 1984-10-26 | 1986-08-19 | Chevron Research Company | Herbicidal 2-(nitrogen heterocycle)5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofurans |
US4568375A (en) * | 1984-10-26 | 1986-02-04 | Chevron Research Company | 2-Substituted 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran herbicides |
US4568378A (en) * | 1984-12-21 | 1986-02-04 | Chevron Research Company | Herbicidal 5-cycloalkylamino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran and derivatives thereof |
US4568377A (en) * | 1985-04-26 | 1986-02-04 | Chevron Research Company | Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran |
US4978386A (en) * | 1985-06-11 | 1990-12-18 | Chevron Research Company | Herbicidal 2-(substituted-phenyl)-3-amino-2-cyclopentenone derivatives |
DE3531773A1 (de) * | 1985-09-06 | 1987-03-19 | Bayer Ag | 3,5 disubstituierte 4-pyridone |
JPH07121911B2 (ja) | 1986-03-26 | 1995-12-25 | クミアイ化学工業株式会社 | 4(1h)−ピリジノン誘導体および農園芸用殺菌剤 |
DE19518739A1 (de) * | 1995-05-22 | 1996-11-28 | Basf Ag | N-Aminopyridonderivate |
WO1997028127A1 (fr) * | 1996-02-02 | 1997-08-07 | Kumiai Chemical Industry Co., Ltd. | Derives de pyridone et herbicides |
EP2052612A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
DE102008037629A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
JP2017206440A (ja) * | 2014-09-10 | 2017-11-24 | 日本曹達株式会社 | ピリジン化合物およびその用途 |
CN110785266B (zh) * | 2017-06-23 | 2022-10-04 | 日东工器株式会社 | 气动工具 |
-
1975
- 1975-08-19 IL IL47938A patent/IL47938A/xx unknown
- 1975-08-19 NZ NZ178426A patent/NZ178426A/xx unknown
- 1975-08-20 IE IE1833/75A patent/IE42444B1/en unknown
- 1975-08-22 NL NLAANVRAGE7509935,A patent/NL181272C/xx not_active IP Right Cessation
- 1975-08-22 CA CA233,945A patent/CA1075696A/en not_active Expired
- 1975-08-22 GB GB34876/75A patent/GB1521092A/en not_active Expired
- 1975-08-23 EG EG508/75A patent/EG12953A/xx active
- 1975-08-25 DE DE2537753A patent/DE2537753C2/de not_active Expired
- 1975-08-25 YU YU02163/75A patent/YU39076B/xx unknown
- 1975-08-26 CH CH1104875A patent/CH630356A5/de not_active IP Right Cessation
- 1975-08-26 FR FR7526320A patent/FR2283130A1/fr active Granted
- 1975-08-27 HU HUEI642A patent/HU169687B/hu unknown
- 1975-08-27 PL PL1975182943A patent/PL109320B1/pl unknown
- 1975-08-27 TR TR19047A patent/TR19047A/xx unknown
- 1975-08-27 NO NO752942A patent/NO145617C/no unknown
- 1975-08-27 DK DK385075A patent/DK385075A/da not_active Application Discontinuation
- 1975-08-27 IT IT26660/75A patent/IT1042113B/it active
- 1975-08-27 AT AT0660375A patent/AT365577B/de not_active IP Right Cessation
- 1975-08-27 OA OA55594A patent/OA05093A/xx unknown
- 1975-08-27 BR BR7505487D patent/BR7505487A/pt unknown
- 1975-08-27 BE BE159503A patent/BE832702A/xx not_active IP Right Cessation
- 1975-08-27 PL PL1975208052A patent/PL111873B1/pl unknown
- 1975-08-27 MX MX756565U patent/MX5136E/es unknown
- 1975-08-27 LU LU73264A patent/LU73264A1/xx unknown
- 1975-08-27 AR AR260155A patent/AR218211A1/es active
- 1975-08-28 JP JP50104853A patent/JPS611401B2/ja not_active Expired
- 1975-08-28 SU SU752170502A patent/SU1074403A3/ru active
- 1975-08-28 DD DD195338A patent/DD127452A5/xx unknown
- 1975-08-28 JP JP50104852A patent/JPS60350B2/ja not_active Expired
- 1975-08-28 DD DD188073A patent/DD123461A5/xx unknown
-
1977
- 1977-01-26 SU SU772446155A patent/SU716522A3/ru active
-
1979
- 1979-10-22 CH CH947279A patent/CH632248A5/de not_active IP Right Cessation
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20160286802A1 (en) * | 2013-04-17 | 2016-10-06 | Sepro Corporation | Herbicidal compositions and methods |
US11026423B2 (en) * | 2013-04-17 | 2021-06-08 | Sepro Corporation | Herbicidal compositions and methods |
US20220125048A1 (en) * | 2013-04-17 | 2022-04-28 | Sepro Corporation | Herbicidal compositions and methods |
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