JPS60351B2 - ３―フエニル―４（ｉｈ）ピリドンおよびピリジンチオン類ならびにそれらの塩類 - Google Patents
３―フエニル―４（ｉｈ）ピリドンおよびピリジンチオン類ならびにそれらの塩類Info
- Publication number
- JPS60351B2 JPS60351B2 JP142576A JP142576A JPS60351B2 JP S60351 B2 JPS60351 B2 JP S60351B2 JP 142576 A JP142576 A JP 142576A JP 142576 A JP142576 A JP 142576A JP S60351 B2 JPS60351 B2 JP S60351B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- pyridone
- methyl
- phenyl
- yield
- 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
- 150000003839 salts Chemical class 0.000 title claims description 19
- LFXDDUCUKGFLFJ-UHFFFAOYSA-N 3-phenyl-1h-pyridin-4-one Chemical compound O=C1C=CNC=C1C1=CC=CC=C1 LFXDDUCUKGFLFJ-UHFFFAOYSA-N 0.000 title claims description 5
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 title claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 114
- -1 cyano, carboxy, hydroxy Chemical group 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical group 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 224
- 241000196324 Embryophyta Species 0.000 description 108
- 238000012360 testing method Methods 0.000 description 66
- 238000000034 method Methods 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 239000002689 soil Substances 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 238000011282 treatment Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 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 description 20
- 239000002904 solvent Substances 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000002363 herbicidal effect Effects 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 14
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 230000035784 germination Effects 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
- 239000004009 herbicide Substances 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 9
- 238000006170 formylation reaction Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000022244 formylation Effects 0.000 description 7
- 230000001629 suppression Effects 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000009331 sowing Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 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 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 238000007429 general method Methods 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- MHBVFQPMQKODRK-UHFFFAOYSA-N 1-phenyl-3-[3-(trifluoromethyl)phenyl]propan-2-one Chemical compound FC(F)(F)C1=CC=CC(CC(=O)CC=2C=CC=CC=2)=C1 MHBVFQPMQKODRK-UHFFFAOYSA-N 0.000 description 4
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- 241000217446 Calystegia sepium Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 235000001560 Prosopis chilensis Nutrition 0.000 description 4
- 235000014460 Prosopis juliflora var juliflora Nutrition 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 240000002439 Sorghum halepense Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 235000014571 nuts Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000009333 weeding Methods 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- 244000052363 Cynodon dactylon Species 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241001494501 Prosopis <angiosperm> Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical class CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 2
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical class C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- QOYMDVZODDSWDA-UHFFFAOYSA-N 1-methyl-3-(2-methylphenyl)-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CC1=CC=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 QOYMDVZODDSWDA-UHFFFAOYSA-N 0.000 description 2
- HNASGVMMKOVJEJ-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CC1=CC=CC(C=2C(C(C=3C=C(C=CC=3)C(F)(F)F)=CN(C)C=2)=O)=C1 HNASGVMMKOVJEJ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- SBERCJBUNCPWER-UHFFFAOYSA-N 1-methyl-3-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound CN1C=CC(=O)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 SBERCJBUNCPWER-UHFFFAOYSA-N 0.000 description 2
- ZXHBGILCPUXDED-UHFFFAOYSA-N 1-methyl-3-phenyl-5-(3-phenylsulfanylphenyl)pyridin-4-one Chemical compound O=C1C(C=2C=C(SC=3C=CC=CC=3)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 ZXHBGILCPUXDED-UHFFFAOYSA-N 0.000 description 2
- VSPRRCMVOPLABC-UHFFFAOYSA-N 1-methyl-3-phenyl-5-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C=C(OC(F)(F)C(F)F)C=CC=2)=CN(C)C=C1C1=CC=CC=C1 VSPRRCMVOPLABC-UHFFFAOYSA-N 0.000 description 2
- OYPBUQASUUMJKG-UHFFFAOYSA-N 1-methylpyridin-4-one Chemical compound CN1C=CC(=O)C=C1 OYPBUQASUUMJKG-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- XWDHZBMZZGGMKI-UHFFFAOYSA-N 3-(1-methyl-4-oxo-5-phenylpyridin-3-yl)benzoic acid Chemical compound O=C1C(C=2C=C(C=CC=2)C(O)=O)=CN(C)C=C1C1=CC=CC=C1 XWDHZBMZZGGMKI-UHFFFAOYSA-N 0.000 description 2
- GGZDJALKLYSDCA-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one Chemical compound O=C1C(C=2C(=CC=CC=2)Cl)=CN(C)C=C1C1=CC=CC(C(F)(F)F)=C1 GGZDJALKLYSDCA-UHFFFAOYSA-N 0.000 description 2
- UXMVRFNURBAMQM-UHFFFAOYSA-N 3-(3,5-dimethylphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound CC1=CC(C)=CC(C=2C(C(C=3C=CC=CC=3)=CN(C)C=2)=O)=C1 UXMVRFNURBAMQM-UHFFFAOYSA-N 0.000 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 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 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 description 2
- BDSYDSMHSRDZJN-UHFFFAOYSA-N 3-(4-methoxy-3-methylphenyl)-1-methyl-5-phenylpyridin-4-one Chemical compound C1=C(C)C(OC)=CC=C1C(C1=O)=CN(C)C=C1C1=CC=CC=C1 BDSYDSMHSRDZJN-UHFFFAOYSA-N 0.000 description 2
- YRYAAALFYIMNGZ-UHFFFAOYSA-N 3-[3-(benzenesulfonyl)phenyl]-1-methyl-5-phenylpyridin-4-one Chemical compound O=C1C(C=2C=C(C=CC=2)S(=O)(=O)C=2C=CC=CC=2)=CN(C)C=C1C1=CC=CC=C1 YRYAAALFYIMNGZ-UHFFFAOYSA-N 0.000 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 description 2
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 2
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- 240000000560 Citrus x paradisi Species 0.000 description 2
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical group [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000008406 SarachaNachtschatten Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 241000208292 Solanaceae Species 0.000 description 2
- 235000004790 Solanum aculeatissimum Nutrition 0.000 description 2
- 235000008424 Solanum demissum Nutrition 0.000 description 2
- 235000018253 Solanum ferox Nutrition 0.000 description 2
- 235000000208 Solanum incanum Nutrition 0.000 description 2
- 235000013131 Solanum macrocarpon Nutrition 0.000 description 2
- 235000009869 Solanum phureja Nutrition 0.000 description 2
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- 238000007142 ring opening reaction Methods 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography 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
- 239000002356 single layer Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 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
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59166175A | 1975-07-03 | 1975-07-03 | |
| US591661 | 1975-07-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS527968A JPS527968A (en) | 1977-01-21 |
| JPS60351B2 true JPS60351B2 (ja) | 1985-01-07 |
Family
ID=24367366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP142576A Expired JPS60351B2 (ja) | 1975-07-03 | 1976-01-01 | ３―フエニル―４（ｉｈ）ピリドンおよびピリジンチオン類ならびにそれらの塩類 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS60351B2 (cs) |
| CS (2) | CS191942B2 (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0239391A2 (en) | 1986-03-26 | 1987-09-30 | Kumiai Chemical Industry Co., Ltd. | 1,2,6-triphenyl-4(1H)-pyridinone and pyridinethione derivatives, production and uses thereof |
-
1975
- 1975-08-27 CS CS583875A patent/CS191942B2/cs unknown
- 1975-08-27 CS CS109778A patent/CS191950B2/cs unknown
-
1976
- 1976-01-01 JP JP142576A patent/JPS60351B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0239391A2 (en) | 1986-03-26 | 1987-09-30 | Kumiai Chemical Industry Co., Ltd. | 1,2,6-triphenyl-4(1H)-pyridinone and pyridinethione derivatives, production and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS527968A (en) | 1977-01-21 |
| CS191950B2 (en) | 1979-07-31 |
| CS191942B2 (en) | 1979-07-31 |
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