CH630356A5 - Process for the preparation of 3-phenyl-5-(substituted)-4(1H)-pyridones, and their use - Google Patents
Process for the preparation of 3-phenyl-5-(substituted)-4(1H)-pyridones, and their use Download PDFInfo
- Publication number
- CH630356A5 CH630356A5 CH1104875A CH1104875A CH630356A5 CH 630356 A5 CH630356 A5 CH 630356A5 CH 1104875 A CH1104875 A CH 1104875A CH 1104875 A CH1104875 A CH 1104875A CH 630356 A5 CH630356 A5 CH 630356A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- pyridone
- methyl
- methylamino
- buten
- Prior art date
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- -1 3-phenyl-5-(substituted)-4(1H)-pyridones Chemical class 0.000 title claims description 321
- 238000000034 method Methods 0.000 title claims description 139
- 238000002360 preparation method Methods 0.000 title claims description 85
- 239000007858 starting material Substances 0.000 claims description 256
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 178
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 178
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 129
- 125000004432 carbon atom Chemical group C* 0.000 claims description 102
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical group 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 48
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 39
- 239000007795 chemical reaction product Substances 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 239000000543 intermediate Substances 0.000 claims description 14
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 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
- 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 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- DWIRBYADUVOADH-UHFFFAOYSA-N 3-(4-chlorophenyl)-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(Cl)C=C1 DWIRBYADUVOADH-UHFFFAOYSA-N 0.000 claims description 4
- ZKCXCHOXRBFRJH-UHFFFAOYSA-N 3-(4-fluorophenyl)-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(F)C=C1 ZKCXCHOXRBFRJH-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 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 3
- 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 3
- ZLFSWRWFOMNGEH-UHFFFAOYSA-N 1-methyl-3-phenyl-5-(4-propan-2-ylphenyl)pyridin-4-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 ZLFSWRWFOMNGEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
- 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 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
- 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 3
- QSURMNTYIIOVHX-UHFFFAOYSA-N 3,5-diphenyl-1h-pyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CNC=C1C1=CC=CC=C1 QSURMNTYIIOVHX-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- LYPFCTNWIMCCOB-UHFFFAOYSA-N 3-(2,5-dichlorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C(=CC=C(Cl)C=2)Cl)=CN(C)C=C1C1=CC=CC=C1 LYPFCTNWIMCCOB-UHFFFAOYSA-N 0.000 claims description 3
- DCBFRIBIQKZOLF-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C(=CC=CC=2)F)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 DCBFRIBIQKZOLF-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- JUEYOYPSARKRTN-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 JUEYOYPSARKRTN-UHFFFAOYSA-N 0.000 claims description 3
- KSDMXEBOVRTOBX-UHFFFAOYSA-N 3-(3-chlorophenyl)-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(Cl)=C1 KSDMXEBOVRTOBX-UHFFFAOYSA-N 0.000 claims description 3
- BKJNBZQCGWKLFF-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-(3-fluorophenyl)-1-methylpyridin-4-one Chemical compound O=C1C(C=2C=C(Cl)C=CC=2)=CN(C)C=C1C1=CC=CC(F)=C1 BKJNBZQCGWKLFF-UHFFFAOYSA-N 0.000 claims description 3
- VYDIPUUHVAQORM-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-(4-chlorophenyl)-1-methylpyridin-4-one Chemical compound O=C1C(C=2C=C(Cl)C=CC=2)=CN(C)C=C1C1=CC=C(Cl)C=C1 VYDIPUUHVAQORM-UHFFFAOYSA-N 0.000 claims description 3
- OTPHBINRHBKSTD-UHFFFAOYSA-N 3-(3-fluorophenyl)-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(F)=C1 OTPHBINRHBKSTD-UHFFFAOYSA-N 0.000 claims description 3
- SQTJIRYGFYBFIC-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound COC1=CC=CC(C=2C(C(C=3C=C(C=CC=3)C(F)(F)F)=CN(C)C=2)=O)=C1 SQTJIRYGFYBFIC-UHFFFAOYSA-N 0.000 claims description 3
- VKORWEFFLNLJNC-UHFFFAOYSA-N 3-(4-bromophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=CC(Br)=CC=2)=CN(C)C=C1C1=CC=CC=C1 VKORWEFFLNLJNC-UHFFFAOYSA-N 0.000 claims description 3
- GVMHHCUTYCEIOB-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=CC(Cl)=CC=2)=CN(C)C=C1C1=CC=CC=C1 GVMHHCUTYCEIOB-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- WVQHJTMQSOGRMR-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound C1=CC(OC)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 WVQHJTMQSOGRMR-UHFFFAOYSA-N 0.000 claims description 3
- YLHWVQMUXOPNGN-UHFFFAOYSA-N 3-benzyl-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=C1CC1=CC=CC=C1 YLHWVQMUXOPNGN-UHFFFAOYSA-N 0.000 claims description 3
- QNWVVDVQCMVWGS-UHFFFAOYSA-N 3-hexyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(CCCCCC)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 QNWVVDVQCMVWGS-UHFFFAOYSA-N 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 claims description 2
- 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
- LEFQOYVNQDOUCZ-UHFFFAOYSA-N 1,3-diphenyl-4-(propylamino)but-3-en-2-one Chemical compound C1(=CC=CC=C1)C(=CNCCC)C(CC1=CC=CC=C1)=O LEFQOYVNQDOUCZ-UHFFFAOYSA-N 0.000 claims description 2
- QYNFTMWLYQPTGM-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(3-chlorophenyl)-4-(methylamino)but-3-en-2-one Chemical compound ClC1=C(C=CC=C1)CC(C(=CNC)C1=CC(=CC=C1)Cl)=O QYNFTMWLYQPTGM-UHFFFAOYSA-N 0.000 claims description 2
- UUIFVZAPTMKLDU-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-(methylamino)-3-phenylbut-3-en-2-one Chemical compound CNC=C(C(=O)CC1=C(Cl)C=CC=C1)C1=CC=CC=C1 UUIFVZAPTMKLDU-UHFFFAOYSA-N 0.000 claims description 2
- OJPYYUIBZZFBEB-UHFFFAOYSA-N 1-(3-bromophenyl)-3-(3-chlorophenyl)-4-(methylamino)but-3-en-2-one Chemical compound CNC=C(C(=O)CC1=CC(Br)=CC=C1)C1=CC(Cl)=CC=C1 OJPYYUIBZZFBEB-UHFFFAOYSA-N 0.000 claims description 2
- BIPOXBBPKLKFPK-UHFFFAOYSA-N 1-(3-bromophenyl)-4-(methylamino)-3-phenylbut-3-en-2-one Chemical compound CNC=C(C(=O)CC1=CC(Br)=CC=C1)C1=CC=CC=C1 BIPOXBBPKLKFPK-UHFFFAOYSA-N 0.000 claims description 2
- IYPDRCYWADJRHH-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-(methylamino)-3-phenylbut-3-en-2-one Chemical compound CNC=C(C(=O)CC1=CC(Cl)=CC=C1)C1=CC=CC=C1 IYPDRCYWADJRHH-UHFFFAOYSA-N 0.000 claims description 2
- XDBHDEKHALYNIS-UHFFFAOYSA-N 1-(3-fluorophenyl)-4-(methylamino)-3-phenylbut-3-en-2-one Chemical compound FC=1C=C(C=CC=1)CC(C(=CNC)C1=CC=CC=C1)=O XDBHDEKHALYNIS-UHFFFAOYSA-N 0.000 claims description 2
- FPNJLLRGXQHJND-UHFFFAOYSA-N 1-(3-hexylphenyl)-4-(methylamino)-3-phenylbut-3-en-2-one Chemical compound C(CCCCC)C=1C=C(C=CC=1)CC(C(=CNC)C1=CC=CC=C1)=O FPNJLLRGXQHJND-UHFFFAOYSA-N 0.000 claims description 2
- HUXDRHOAONZROC-UHFFFAOYSA-N 1-(3-methoxyphenyl)-4-(methylamino)-3-[3-(trifluoromethyl)phenyl]but-3-en-2-one Chemical compound CNC=C(C(=O)CC1=CC(OC)=CC=C1)C1=CC(=CC=C1)C(F)(F)F HUXDRHOAONZROC-UHFFFAOYSA-N 0.000 claims description 2
- QFYNJKKZVQXAFV-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-(methylamino)-3-phenylbut-3-en-2-one Chemical compound CNC=C(C(=O)CC1=CC=C(Cl)C=C1)C1=CC=CC=C1 QFYNJKKZVQXAFV-UHFFFAOYSA-N 0.000 claims description 2
- BOXJSEOYOUQZBN-UHFFFAOYSA-N 1-(4-ethylphenyl)-4-(methylamino)-3-phenylbut-3-en-2-one Chemical compound C(C)C1=CC=C(C=C1)CC(C(=CNC)C1=CC=CC=C1)=O BOXJSEOYOUQZBN-UHFFFAOYSA-N 0.000 claims description 2
- CBPDUEWNGOODCF-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(methylamino)-3-[3-(trifluoromethyl)phenyl]but-3-en-2-one Chemical compound CNC=C(C(=O)CC1=CC=C(F)C=C1)C1=CC(=CC=C1)C(F)(F)F CBPDUEWNGOODCF-UHFFFAOYSA-N 0.000 claims description 2
- LGQMCRNINKAXEV-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-(methylamino)-3-[3-(trifluoromethyl)phenyl]but-3-en-2-one Chemical compound CNC=C(C(=O)CC1=CC=C(OC)C=C1)C1=CC(=CC=C1)C(F)(F)F LGQMCRNINKAXEV-UHFFFAOYSA-N 0.000 claims description 2
- GIALCWDJGNHAKM-UHFFFAOYSA-N 1-methoxy-4-(methylamino)-3-phenylbut-3-en-2-one Chemical compound COCC(C(=CNC)C1=CC=CC=C1)=O GIALCWDJGNHAKM-UHFFFAOYSA-N 0.000 claims description 2
- FQDPEZAOBVOFTR-UHFFFAOYSA-N 1-methyl-3-phenyl-5-(3-prop-1-en-2-ylphenyl)pyridin-4-one Chemical compound CC(=C)C1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 FQDPEZAOBVOFTR-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
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
- RUYZMUCKLKBGFO-UHFFFAOYSA-N 3,5-diphenyl-1-propan-2-ylpyridin-4-one Chemical compound O=C1C(C=2C=CC=CC=2)=CN(C(C)C)C=C1C1=CC=CC=C1 RUYZMUCKLKBGFO-UHFFFAOYSA-N 0.000 claims description 2
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- YQWCGZHDWUJHCB-UHFFFAOYSA-N C(#N)C=1C=C(C=CC1)C(=CNC)C(CC1=CC(=CC=C1)C#N)=O Chemical compound C(#N)C=1C=C(C=CC1)C(=CNC)C(CC1=CC(=CC=C1)C#N)=O YQWCGZHDWUJHCB-UHFFFAOYSA-N 0.000 description 1
- XCIOHDAGFARHOB-UHFFFAOYSA-N C(C)OC(=O)C(=CNC)C(CC1=CC=CC=C1)=O Chemical compound C(C)OC(=O)C(=CNC)C(CC1=CC=CC=C1)=O XCIOHDAGFARHOB-UHFFFAOYSA-N 0.000 description 1
- GIUJWKHDWOKHRZ-UHFFFAOYSA-N C(C)OC1=C(C=CC(=C1)OCC)N1C=CC(C=C1)=S Chemical compound C(C)OC1=C(C=CC(=C1)OCC)N1C=CC(C=C1)=S GIUJWKHDWOKHRZ-UHFFFAOYSA-N 0.000 description 1
- IZUHSTQPMVOLFB-UHFFFAOYSA-N C1(C=CC=CC1)C1=C(C=C(C=C1)C1=CN(C=C(C1=S)C1=CC(=CC(=C1)S(=O)C1=C(C=CC=C1)[N+](=O)[O-])O)CC)F Chemical compound C1(C=CC=CC1)C1=C(C=C(C=C1)C1=CN(C=C(C1=S)C1=CC(=CC(=C1)S(=O)C1=C(C=CC=C1)[N+](=O)[O-])O)CC)F IZUHSTQPMVOLFB-UHFFFAOYSA-N 0.000 description 1
- XAOLVNQEGZSSRM-UHFFFAOYSA-N CCCCCCCCC(C=C(C=C1)C2=CN(C(F)(F)F)C=C(C(C=CC=C3)=C3OC3=CC(CC)=CC=C3)C2=O)=C1F Chemical compound CCCCCCCCC(C=C(C=C1)C2=CN(C(F)(F)F)C=C(C(C=CC=C3)=C3OC3=CC(CC)=CC=C3)C2=O)=C1F XAOLVNQEGZSSRM-UHFFFAOYSA-N 0.000 description 1
- ROGOUBAKOCRVPX-UHFFFAOYSA-N CCOC(=O)C1=CC=CC(=C1)CC(=O)C(=CNC)C2=CC=CC=C2 Chemical compound CCOC(=O)C1=CC=CC(=C1)CC(=O)C(=CNC)C2=CC=CC=C2 ROGOUBAKOCRVPX-UHFFFAOYSA-N 0.000 description 1
- DNVZLQPCRCPTLA-UHFFFAOYSA-N CNC=C(C(=O)CC1=CC(Br)=CC=C1)C1=CC(Br)=CC=C1 Chemical compound CNC=C(C(=O)CC1=CC(Br)=CC=C1)C1=CC(Br)=CC=C1 DNVZLQPCRCPTLA-UHFFFAOYSA-N 0.000 description 1
- QFMMGTWHQFHKPA-UHFFFAOYSA-N CNC=C(C(=O)CC1=CC(F)=CC=C1)C1=CC(F)=CC=C1 Chemical compound CNC=C(C(=O)CC1=CC(F)=CC=C1)C1=CC(F)=CC=C1 QFMMGTWHQFHKPA-UHFFFAOYSA-N 0.000 description 1
- YDHLNJASCQRBBM-UHFFFAOYSA-N COC=1C=C(C=CC1OC)C(=CNC)C(CC1=CC(=C(C=C1)OC)OC)=O Chemical compound COC=1C=C(C=CC1OC)C(=CNC)C(CC1=CC(=C(C=C1)OC)OC)=O YDHLNJASCQRBBM-UHFFFAOYSA-N 0.000 description 1
- FMRHITJMHTUHIQ-UHFFFAOYSA-N CS(=O)(=O)O.C1(CCCCC1)OC1=CC=C(C=C1)C1=CN(C=C(C1=O)C1=CC=CC=C1)C Chemical compound CS(=O)(=O)O.C1(CCCCC1)OC1=CC=C(C=C1)C1=CN(C=C(C1=O)C1=CC=CC=C1)C FMRHITJMHTUHIQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- USEAXFKVKXBPSI-UHFFFAOYSA-N Cl.C(C)OCCCC=CCC1=CN(C=C(C1=S)C1=CC=CC=C1)C Chemical compound Cl.C(C)OCCCC=CCC1=CN(C=C(C1=S)C1=CC=CC=C1)C USEAXFKVKXBPSI-UHFFFAOYSA-N 0.000 description 1
- CASAPAVJRYDCOW-UHFFFAOYSA-N ClC(CC)SC1=C(C=CC=C1)C1=CN(C=C(C1=O)C1=CC(=CC(=C1)C(=O)OC)CCCC=C)N(C)C Chemical compound ClC(CC)SC1=C(C=CC=C1)C1=CN(C=C(C1=O)C1=CC(=CC(=C1)C(=O)OC)CCCC=C)N(C)C CASAPAVJRYDCOW-UHFFFAOYSA-N 0.000 description 1
- GHXCDTJZOSMGCC-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1=CN(C=C(C1=O)C1=C(C=C(C=C1)OC)OC)CCC.BrC=1C=C(C=CC1)C1=CN(C=C(C1=O)C1=CC=CC=C1)C Chemical compound ClC1=CC=C(C=C1)C1=CN(C=C(C1=O)C1=C(C=C(C=C1)OC)OC)CCC.BrC=1C=C(C=CC1)C1=CN(C=C(C1=O)C1=CC=CC=C1)C GHXCDTJZOSMGCC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DUKKDIUMOYKQQS-UHFFFAOYSA-N IC(CCCC=1C=C(C=CC1)C1=CN(C=C(C1=O)C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)F)C(F)(F)F)I Chemical compound IC(CCCC=1C=C(C=CC1)C1=CN(C=C(C1=O)C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)F)C(F)(F)F)I DUKKDIUMOYKQQS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019201 POBr3 Inorganic materials 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 235000006545 Ziziphus mauritiana Nutrition 0.000 description 1
- 240000000038 Ziziphus mauritiana Species 0.000 description 1
- FZDGDURVHJUIRQ-UHFFFAOYSA-N [2-[5-(chloromethoxy)-1-(cyanomethyl)-4-sulfanylidenepyridin-3-yl]phenyl] formate Chemical compound S=C1C(OCCl)=CN(CC#N)C=C1C1=CC=CC=C1OC=O FZDGDURVHJUIRQ-UHFFFAOYSA-N 0.000 description 1
- BSIUASOCHPGPFN-UHFFFAOYSA-N [3-[1-chloro-5-[2-(8-cyanoundecylsulfanyl)phenyl]-2-(difluoromethyl)-4-oxopyridin-3-yl]-5-ethylphenyl] acetate Chemical compound CCCC(C#N)CCCCCCCSC1=CC=CC=C1C(C1=O)=CN(Cl)C(C(F)F)=C1C1=CC(CC)=CC(OC(C)=O)=C1 BSIUASOCHPGPFN-UHFFFAOYSA-N 0.000 description 1
- RZOCCAZPZKOTTG-UHFFFAOYSA-N [3-[1-ethenyl-4-oxo-5-[3-(5-phenylpentylsulfinyl)phenyl]pyridin-3-yl]-5-methylsulfonyloxyphenyl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC(OS(C)(=O)=O)=CC(C=2C(C(C=3C=C(C=CC=3)S(=O)CCCCCC=3C=CC=CC=3)=CN(C=C)C=2)=O)=C1 RZOCCAZPZKOTTG-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical group [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 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
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 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
- KOFGDZXGFOTMDE-UHFFFAOYSA-N ethyl 3-(1-methyl-4-oxo-5-phenylpyridin-3-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 KOFGDZXGFOTMDE-UHFFFAOYSA-N 0.000 description 1
- CNIQCHSDNOMGLU-UHFFFAOYSA-N ethyl 3-[1-(methylamino)-3-oxo-4-phenylbut-1-en-2-yl]benzoate Chemical compound C(C)OC(=O)C=1C=C(C=CC=1)C(=CNC)C(CC1=CC=CC=C1)=O CNIQCHSDNOMGLU-UHFFFAOYSA-N 0.000 description 1
- KKIGZVKZKMRSQO-UHFFFAOYSA-N ethyl 5-(methylamino)-3-oxo-4-phenylpent-4-enoate Chemical compound C(C)OC(=O)CC(C(=CNC)C1=CC=CC=C1)=O KKIGZVKZKMRSQO-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000006038 hexenyl group 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
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 150000002465 imidoyl halides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- HOWQANUZANLJFA-UHFFFAOYSA-N methyl 2-[3-(2-iodophenoxy)-4-oxo-5-[3-(4-propan-2-yloxyphenyl)phenyl]pyridin-1-yl]acetate Chemical compound O=C1C(C=2C=C(C=CC=2)C=2C=CC(OC(C)C)=CC=2)=CN(CC(=O)OC)C=C1OC1=CC=CC=C1I HOWQANUZANLJFA-UHFFFAOYSA-N 0.000 description 1
- WMJVQTSBLJTQSY-UHFFFAOYSA-N methyl 2-[3-[2-(3-cyanopropylsulfinyl)phenyl]-5-phenyl-4-sulfanylidenepyridin-1-yl]acetate Chemical compound S=C1C(C=2C(=CC=CC=2)S(=O)CCCC#N)=CN(CC(=O)OC)C=C1C1=CC=CC=C1 WMJVQTSBLJTQSY-UHFFFAOYSA-N 0.000 description 1
- DIUIEXAIFMKIGI-UHFFFAOYSA-N methyl 2-[3-[2-(chloromethyl)phenyl]-4-oxopyridin-1-yl]acetate Chemical compound COC(=O)CN1C=CC(=O)C(C=2C(=CC=CC=2)CCl)=C1 DIUIEXAIFMKIGI-UHFFFAOYSA-N 0.000 description 1
- VCVHCTSAVFDRSB-UHFFFAOYSA-N methyl 2-[3-[3-(3-cyanopropylsulfonyl)phenyl]-4-oxo-5-phenylpyridin-1-yl]acetate Chemical compound O=C1C(C=2C=C(C=CC=2)S(=O)(=O)CCCC#N)=CN(CC(=O)OC)C=C1C1=CC=CC=C1 VCVHCTSAVFDRSB-UHFFFAOYSA-N 0.000 description 1
- IZZHKCNXKMNOQI-UHFFFAOYSA-N methyl 5-(2,4-dimethylphenyl)-1-methyl-4-oxopyridine-3-carboxylate Chemical compound O=C1C(C(=O)OC)=CN(C)C=C1C1=CC=C(C)C=C1C IZZHKCNXKMNOQI-UHFFFAOYSA-N 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 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
- 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 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
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-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
- 239000008096 xylene Substances 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
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- 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
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- 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
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- 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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- 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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- 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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- 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
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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
- C07D213/84—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
-
- 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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- 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 |
---|---|
CH630356A5 true CH630356A5 (en) | 1982-06-15 |
Family
ID=27053808
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1104875A CH630356A5 (en) | 1974-08-28 | 1975-08-26 | Process for the preparation of 3-phenyl-5-(substituted)-4(1H)-pyridones, and their use |
CH947279A CH632248A5 (en) | 1974-08-28 | 1979-10-22 | Process for the preparation of 3-phenyl-5-substituted-4(1H)pyridones, and their use |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH947279A CH632248A5 (en) | 1974-08-28 | 1979-10-22 | Process for the preparation of 3-phenyl-5-substituted-4(1H)pyridones, and their use |
Country Status (27)
Country | Link |
---|---|
JP (2) | JPS611401B2 (nl) |
AR (1) | AR218211A1 (nl) |
AT (1) | AT365577B (nl) |
BE (1) | BE832702A (nl) |
BR (1) | BR7505487A (nl) |
CA (1) | CA1075696A (nl) |
CH (2) | CH630356A5 (nl) |
DD (2) | DD123461A5 (nl) |
DE (1) | DE2537753C2 (nl) |
DK (1) | DK385075A (nl) |
EG (1) | EG12953A (nl) |
FR (1) | FR2283130A1 (nl) |
GB (1) | GB1521092A (nl) |
HU (1) | HU169687B (nl) |
IE (1) | IE42444B1 (nl) |
IL (1) | IL47938A (nl) |
IT (1) | IT1042113B (nl) |
LU (1) | LU73264A1 (nl) |
MX (1) | MX5136E (nl) |
NL (1) | NL181272C (nl) |
NO (1) | NO145617C (nl) |
NZ (1) | NZ178426A (nl) |
OA (1) | OA05093A (nl) |
PL (2) | PL109320B1 (nl) |
SU (2) | SU1074403A3 (nl) |
TR (1) | TR19047A (nl) |
YU (1) | YU39076B (nl) |
Families Citing this family (23)
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 |
EP0073999B1 (de) * | 1981-09-05 | 1986-01-15 | 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 |
US6048823A (en) | 1996-02-02 | 2000-04-11 | Kumiai Chemical Industry Co., Ltd. | Pyridone derivatives and 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 |
US11026423B2 (en) * | 2013-04-17 | 2021-06-08 | Sepro Corporation | Herbicidal compositions and methods |
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 |
KR102338966B1 (ko) * | 2017-06-23 | 2021-12-13 | 니토 코키 가부시키가이샤 | 에어 공구 |
-
1975
- 1975-08-19 NZ NZ178426A patent/NZ178426A/xx unknown
- 1975-08-19 IL IL47938A patent/IL47938A/xx unknown
- 1975-08-20 IE IE1833/75A patent/IE42444B1/en unknown
- 1975-08-22 GB GB34876/75A patent/GB1521092A/en not_active Expired
- 1975-08-22 CA CA233,945A patent/CA1075696A/en not_active Expired
- 1975-08-22 NL NLAANVRAGE7509935,A patent/NL181272C/nl not_active IP Right Cessation
- 1975-08-23 EG EG508/75A patent/EG12953A/xx active
- 1975-08-25 YU YU02163/75A patent/YU39076B/xx unknown
- 1975-08-25 DE DE2537753A patent/DE2537753C2/de not_active Expired
- 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 DK DK385075A patent/DK385075A/da not_active Application Discontinuation
- 1975-08-27 BR BR7505487D patent/BR7505487A/pt unknown
- 1975-08-27 MX MX756565U patent/MX5136E/es unknown
- 1975-08-27 OA OA55594A patent/OA05093A/xx unknown
- 1975-08-27 AR AR260155A patent/AR218211A1/es active
- 1975-08-27 PL PL1975182943A patent/PL109320B1/pl unknown
- 1975-08-27 IT IT26660/75A patent/IT1042113B/it active
- 1975-08-27 NO NO752942A patent/NO145617C/no unknown
- 1975-08-27 PL PL1975208052A patent/PL111873B1/pl unknown
- 1975-08-27 AT AT0660375A patent/AT365577B/de not_active IP Right Cessation
- 1975-08-27 HU HUEI642A patent/HU169687B/hu unknown
- 1975-08-27 TR TR19047A patent/TR19047A/xx unknown
- 1975-08-27 LU LU73264A patent/LU73264A1/xx unknown
- 1975-08-27 BE BE159503A patent/BE832702A/xx not_active IP Right Cessation
- 1975-08-28 DD DD188073A patent/DD123461A5/xx unknown
- 1975-08-28 DD DD195338A patent/DD127452A5/xx unknown
- 1975-08-28 SU SU752170502A patent/SU1074403A3/ru active
- 1975-08-28 JP JP50104853A patent/JPS611401B2/ja not_active Expired
- 1975-08-28 JP JP50104852A patent/JPS60350B2/ja not_active Expired
-
1977
- 1977-01-26 SU SU772446155A patent/SU716522A3/ru active
-
1979
- 1979-10-22 CH CH947279A patent/CH632248A5/de not_active IP Right Cessation
Also Published As
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