EA002418B1 - Производные гетароилциклогександиона с гербицидным действием - Google Patents
Производные гетароилциклогександиона с гербицидным действием Download PDFInfo
- Publication number
- EA002418B1 EA002418B1 EA199900273A EA199900273A EA002418B1 EA 002418 B1 EA002418 B1 EA 002418B1 EA 199900273 A EA199900273 A EA 199900273A EA 199900273 A EA199900273 A EA 199900273A EA 002418 B1 EA002418 B1 EA 002418B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- formula
- alkoxy
- haloalkyl
- hydrogen
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 16
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical class O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 title description 2
- -1 phenyloxy, phenylthio, phenylsulfinyl Chemical group 0.000 claims abstract description 396
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 239000001257 hydrogen Substances 0.000 claims abstract description 54
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 39
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 33
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 22
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 239000012634 fragment Substances 0.000 claims abstract description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 15
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 13
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract description 8
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 8
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims abstract description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 6
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims abstract description 6
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims abstract description 6
- 239000004009 herbicide Substances 0.000 claims abstract description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 238000005917 acylation reaction Methods 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 230000010933 acylation Effects 0.000 claims abstract description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 3
- 239000004094 surface-active agent Substances 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 8
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000007788 liquid Substances 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
- 125000005108 alkenylthio group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- YDZNRNHKJQTGCG-UHFFFAOYSA-N 1,1'-binaphthyl-2,2'-dicarboxylic acid Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3C(=O)O)=C(C(O)=O)C=CC2=C1 YDZNRNHKJQTGCG-UHFFFAOYSA-N 0.000 claims description 4
- 125000005109 alkynylthio group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 claims 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 20
- 150000001204 N-oxides Chemical class 0.000 abstract 5
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 5
- 238000004519 manufacturing process Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 15
- 235000011613 Pinus brutia Nutrition 0.000 description 15
- 241000018646 Pinus brutia Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000013543 active substance Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000010410 dusting Methods 0.000 description 7
- 150000002084 enol ethers Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- 150000002537 isoquinolines Chemical class 0.000 description 6
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 125000005138 alkoxysulfonyl group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000009827 uniform distribution Methods 0.000 description 4
- HXHZCOASPJWXPP-UHFFFAOYSA-N 5-nitroquinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=C([N+]([O-])=O)C2=C1 HXHZCOASPJWXPP-UHFFFAOYSA-N 0.000 description 3
- PPJDILQBGRMTFE-UHFFFAOYSA-N 8-bromoquinoline-5-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(Br)C2=N1 PPJDILQBGRMTFE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 229910000288 alkali metal carbonate Chemical group 0.000 description 3
- 150000008041 alkali metal carbonates Chemical group 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000005134 alkynylsulfinyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- BQZMFXPUPJVQSJ-UHFFFAOYSA-N 1,8-dimethyl-3,4-dihydro-2h-quinoline-5-carboxylic acid Chemical compound C1=CC(C)=C2N(C)CCCC2=C1C(O)=O BQZMFXPUPJVQSJ-UHFFFAOYSA-N 0.000 description 2
- WCXRGNXSZMQYCM-UHFFFAOYSA-N 1-acetyl-4-oxo-2,3-dihydroquinoline-7-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2N(C(=O)C)CCC(=O)C2=C1 WCXRGNXSZMQYCM-UHFFFAOYSA-N 0.000 description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 2
- POFJHSYNRZHABR-UHFFFAOYSA-N 3-amino-4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C=C1N POFJHSYNRZHABR-UHFFFAOYSA-N 0.000 description 2
- MZIWQSVCXANUIX-UHFFFAOYSA-N 4-methanesulfonyl-3-nitro-benzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C=C1[N+]([O-])=O MZIWQSVCXANUIX-UHFFFAOYSA-N 0.000 description 2
- QZGCJUTXCXSJBK-UHFFFAOYSA-N 4-oxo-2,3-dihydro-1h-quinoline-7-carboxylic acid Chemical compound O=C1CCNC2=CC(C(=O)O)=CC=C21 QZGCJUTXCXSJBK-UHFFFAOYSA-N 0.000 description 2
- HOURNFHWRPRYBC-UHFFFAOYSA-N 5-nitroquinoline-6-carboxylic acid Chemical compound N1=CC=CC2=C([N+]([O-])=O)C(C(=O)O)=CC=C21 HOURNFHWRPRYBC-UHFFFAOYSA-N 0.000 description 2
- UBENFVCBHLLYSK-UHFFFAOYSA-N 5-nitroquinoline-8-carbonitrile Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=C(C#N)C2=N1 UBENFVCBHLLYSK-UHFFFAOYSA-N 0.000 description 2
- CENBTULRDDPOGR-UHFFFAOYSA-N 6-methyl-5-nitroquinoline Chemical compound N1=CC=CC2=C([N+]([O-])=O)C(C)=CC=C21 CENBTULRDDPOGR-UHFFFAOYSA-N 0.000 description 2
- LUYISICIYVKBTA-UHFFFAOYSA-N 6-methylquinoline Chemical compound N1=CC=CC2=CC(C)=CC=C21 LUYISICIYVKBTA-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- LEMUPVPKQOTZAE-UHFFFAOYSA-N 8-bromo-5-nitroquinoline Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=C(Br)C2=N1 LEMUPVPKQOTZAE-UHFFFAOYSA-N 0.000 description 2
- UNFYSPONYGTMNH-UHFFFAOYSA-N 8-bromoquinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=C(Br)C2=N1 UNFYSPONYGTMNH-UHFFFAOYSA-N 0.000 description 2
- AKXRRWSXYCJIHR-UHFFFAOYSA-N 8-bromoquinoline-5-carbonitrile Chemical compound C1=CN=C2C(Br)=CC=C(C#N)C2=C1 AKXRRWSXYCJIHR-UHFFFAOYSA-N 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by 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
- A01N43/42—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 condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/08—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with a hetero atom directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19638486A DE19638486A1 (de) | 1996-09-20 | 1996-09-20 | Hetaroylderivate |
| PCT/EP1997/004894 WO1998012180A1 (de) | 1996-09-20 | 1997-09-09 | Hetaroylcyclohexandionderivate mit herbizider wirkung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199900273A1 EA199900273A1 (ru) | 1999-12-29 |
| EA002418B1 true EA002418B1 (ru) | 2002-04-25 |
Family
ID=7806281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199900273A EA002418B1 (ru) | 1996-09-20 | 1997-09-09 | Производные гетароилциклогександиона с гербицидным действием |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6479436B1 (enExample) |
| EP (1) | EP0931070B1 (enExample) |
| JP (1) | JP4386465B2 (enExample) |
| KR (1) | KR20010029525A (enExample) |
| CN (1) | CN1230951A (enExample) |
| AR (1) | AR008848A1 (enExample) |
| AT (1) | ATE234817T1 (enExample) |
| AU (1) | AU736395B2 (enExample) |
| BR (1) | BR9711407A (enExample) |
| CA (1) | CA2266526C (enExample) |
| DE (2) | DE19638486A1 (enExample) |
| EA (1) | EA002418B1 (enExample) |
| HU (1) | HUP9903186A3 (enExample) |
| IL (1) | IL128744A0 (enExample) |
| NZ (1) | NZ334547A (enExample) |
| PL (1) | PL332212A1 (enExample) |
| SK (1) | SK26199A3 (enExample) |
| WO (1) | WO1998012180A1 (enExample) |
| ZA (1) | ZA978452B (enExample) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6093732A (en) * | 1997-12-22 | 2000-07-25 | Pharmacia & Upjohn Company | 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents |
| CA2343144A1 (en) * | 1998-09-08 | 2000-03-16 | Basf Aktiengesellschaft | Cyclohexenonequinolinoyl-derivatives as herbicidal agents |
| WO2001074802A1 (en) * | 2000-04-04 | 2001-10-11 | Idemitsu Kosan Co., Ltd. | Fused-benzoyl derivatives and herbicide compositions containing the same |
| CN1199950C (zh) * | 2000-08-09 | 2005-05-04 | 霍夫曼-拉罗奇有限公司 | 作为抗炎剂的喹啉衍生物 |
| MY133587A (en) | 2002-05-29 | 2007-11-30 | Glaxo Group Ltd | Aromatic sulfones and their medical use |
| US7244316B2 (en) | 2003-05-15 | 2007-07-17 | Delphi Technologies, Inc. | Methods of making gas sensors and sensors formed therefrom |
| CN103880827B (zh) | 2004-07-15 | 2017-01-04 | 阿尔巴尼分子研究公司 | 芳基和杂芳基取代的四氢异喹啉及其阻断去甲肾上腺素、多巴胺和血清素的重摄取的应用 |
| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| WO2008079427A1 (en) | 2006-05-11 | 2008-07-03 | Janssen Pharmaceutica N.V. | 1,2,3,4-tetrahydro-quinoline derivatives as cetp inhibitors |
| CA2651817A1 (en) | 2006-05-11 | 2007-11-22 | Janssen Pharmaceutica N.V. | 3,4-dihydro-2h-benzo[1,4]oxazine and thiazine derivatives as cetp inhibitors |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| NZ584152A (en) | 2007-09-14 | 2011-11-25 | Ortho Mcneil Janssen Pharm | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
| US8722894B2 (en) * | 2007-09-14 | 2014-05-13 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| SI2203439T1 (sl) | 2007-09-14 | 2011-05-31 | Ortho Mcneil Janssen Pharm | 1',3'-disubstituirani 4-fenil-3,4,5,6-tetrahidro-2H-1'H-(1,4')bipiridinil-2'-oni |
| RU2492170C9 (ru) | 2007-11-14 | 2013-12-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Имидазо[1,2-а]пиридиновые производные и их применение в качестве положительных аллостерических модуляторов рецепторов mglur2 |
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| AU2009289784B2 (en) | 2008-09-02 | 2012-03-22 | Addex Pharma S.A. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| US8697689B2 (en) | 2008-10-16 | 2014-04-15 | Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| WO2010060589A1 (en) | 2008-11-28 | 2010-06-03 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| US8334236B2 (en) | 2009-02-03 | 2012-12-18 | Kumiai Chemical Industry Co., Ltd. | Ring-fused 2-pyridone derivatives and herbicides |
| CN102439008B (zh) | 2009-05-12 | 2015-04-29 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其用于治疗或预防神经和精神病症的用途 |
| US8815894B2 (en) * | 2009-05-12 | 2014-08-26 | Bristol-Myers Squibb Company | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
| KR101830447B1 (ko) * | 2009-05-12 | 2018-02-20 | 알바니 몰레큘라 리써치, 인크. | 7-([1,2,4]트리아졸로[1,5-α]피리딘-6-일)-4-(3,4-디클로로페닐)-1,2,3,4-테트라하이드로이소퀴놀린 및 이의 용도 |
| EP2429295B1 (en) | 2009-05-12 | 2013-12-25 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| IN2012DN00352A (enExample) * | 2009-06-16 | 2015-08-21 | Bikam Pharmaceuticals Inc | |
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| AR081527A1 (es) | 2010-03-23 | 2012-10-03 | Basf Se | Piridinas sustituidas que tienen accion herbicida |
| JP2013522339A (ja) | 2010-03-23 | 2013-06-13 | ビーエーエスエフ ソシエタス・ヨーロピア | 除草作用を有する置換されたピリジン |
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| JP5852665B2 (ja) | 2010-11-08 | 2016-02-03 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | 1,2,4−トリアゾロ[4,3−a]ピリジン誘導体およびmGluR2受容体のポジティブアロステリックモジュレーターとしてのそれらの使用 |
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| MX2013005694A (es) | 2010-12-23 | 2013-07-05 | Basf Se | Piridinas sustituidas que tienen accion herbicida. |
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| WO2012168241A1 (en) | 2011-06-09 | 2012-12-13 | Basf Se | Substituted pyrazines having herbicidal activity |
| AR086894A1 (es) | 2011-06-09 | 2014-01-29 | Basf Se | Derivados de 2,2-dioxo-oxatiin[3,2-b]piridina, una composicion que los comprende y un metodo para controlar vegetacion indeseada que los emplea |
| AU2012346214B2 (en) * | 2011-11-30 | 2017-09-14 | Bikam Pharmaceuticals, Inc. | Opsin-binding ligands, compositions and methods of use |
| BR112014029531A2 (pt) | 2012-06-01 | 2017-06-27 | Basf Se | composto de piridina, composição e método para controlar vegetação indesejada |
| CN103891748B (zh) * | 2012-12-27 | 2015-11-11 | 北京法盖银科技有限公司 | 一种除草剂组合物及其应用 |
| CN103155923B (zh) * | 2013-03-27 | 2015-01-07 | 北京法盖银科技有限公司 | 一种含有芳氧苯氧丙酸酯类化合物的除草剂组合物及其应用 |
| CN103621507B (zh) * | 2013-03-27 | 2015-10-07 | 北京法盖银科技有限公司 | 含有2-(喹啉-8-基)羰基-环己烷-1,3-二酮类化合物的除草组合物及其应用 |
| WO2014187705A1 (en) | 2013-05-24 | 2014-11-27 | Basf Se | Substituted pyridine compounds having herbicidal activity |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| CN106029076B (zh) | 2013-11-18 | 2019-06-07 | 福马疗法公司 | 作为bet溴域抑制剂的苯并哌嗪组合物 |
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| AR099120A1 (es) | 2014-01-20 | 2016-06-29 | Bayer Cropscience Ag | Derivados de quinolina como insecticidas y acaricidas |
| AU2015208233B2 (en) | 2014-01-21 | 2019-08-29 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| ES2860298T3 (es) | 2014-01-21 | 2021-10-04 | Janssen Pharmaceutica Nv | Combinaciones que comprenden moduladores alostéricos positivos del receptor glutamatérgico metabotrópico de subtipo 2 y su uso |
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| WO2020063981A1 (zh) * | 2018-09-29 | 2020-04-02 | 山东先达农化股份有限公司 | 三酮类化合物及其制备方法和应用以及一种除草剂 |
| CN111670182A (zh) * | 2018-12-21 | 2020-09-15 | 东莞市东阳光农药研发有限公司 | 喹啉衍生物及其制备方法和用途 |
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| EP4045485A1 (en) | 2019-10-18 | 2022-08-24 | The Regents Of The University Of California | 3-phenylsulphonyl-quinoline derivatives as agents for treating pathogenic blood vessels disorders |
| CN110835321B (zh) * | 2019-11-28 | 2020-11-24 | 东北农业大学 | 一种含有喹喔啉结构的三酮类化合物、制备方法及其应用 |
| CN113912537B (zh) * | 2021-08-27 | 2024-05-07 | 重庆化工职业学院 | 2-(喹啉-8-基)羰基-环己烷-1,3-二酮类化合物及其制备方法与应用 |
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| EP0283261A2 (en) * | 1987-03-19 | 1988-09-21 | Zeneca Limited | Herbicidal substituted cyclic diones |
| EP0563817A2 (de) * | 1992-03-31 | 1993-10-06 | Hoechst Aktiengesellschaft | Salze von 2-Benzoyl-cyclohexandionen, Selektive herbizide Mittel, Verfahren zu ihrer Herstellung und ihre Verwendung zur Unkrautbekämpfung |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0243313B1 (de) | 1986-04-24 | 1990-05-16 | Ciba-Geigy Ag | Acyl-cyclohexandione und deren Oximäther mit herbizider und das Pflanzenwachstum regulierender Wirkung |
| IL91083A (en) | 1988-07-25 | 1993-04-04 | Ciba Geigy | Cyclohexanedione derivatives, their preparation and their use as herbicides |
| WO1994004524A1 (fr) * | 1992-08-18 | 1994-03-03 | Idemitsu Kosan Co., Ltd. | Derive de cyclohexanedione |
| DE4434987A1 (de) | 1994-09-30 | 1996-04-04 | Basf Ag | 2-Aroylcyclohexandione, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide oder das Pflanzenwachstum regulierende Mittel |
| JPH11509192A (ja) * | 1995-06-29 | 1999-08-17 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 除草性ケタール類およびスピロ環類 |
| EP0846112A1 (en) | 1995-08-25 | 1998-06-10 | E.I. Du Pont De Nemours And Company | Bicyclic herbicides |
-
1996
- 1996-09-20 DE DE19638486A patent/DE19638486A1/de not_active Withdrawn
-
1997
- 1997-09-09 NZ NZ334547A patent/NZ334547A/xx unknown
- 1997-09-09 DE DE59709582T patent/DE59709582D1/de not_active Expired - Lifetime
- 1997-09-09 EP EP97941998A patent/EP0931070B1/de not_active Expired - Lifetime
- 1997-09-09 US US09/254,973 patent/US6479436B1/en not_active Expired - Fee Related
- 1997-09-09 KR KR1019997002348A patent/KR20010029525A/ko not_active Withdrawn
- 1997-09-09 AU AU43833/97A patent/AU736395B2/en not_active Ceased
- 1997-09-09 HU HU9903186A patent/HUP9903186A3/hu unknown
- 1997-09-09 PL PL97332212A patent/PL332212A1/xx unknown
- 1997-09-09 WO PCT/EP1997/004894 patent/WO1998012180A1/de not_active Ceased
- 1997-09-09 SK SK261-99A patent/SK26199A3/sk unknown
- 1997-09-09 JP JP51424298A patent/JP4386465B2/ja not_active Expired - Lifetime
- 1997-09-09 BR BR9711407A patent/BR9711407A/pt not_active Application Discontinuation
- 1997-09-09 AT AT97941998T patent/ATE234817T1/de not_active IP Right Cessation
- 1997-09-09 EA EA199900273A patent/EA002418B1/ru not_active IP Right Cessation
- 1997-09-09 CN CN97198078A patent/CN1230951A/zh active Pending
- 1997-09-09 IL IL12874497A patent/IL128744A0/xx unknown
- 1997-09-09 CA CA002266526A patent/CA2266526C/en not_active Expired - Fee Related
- 1997-09-19 ZA ZA978452A patent/ZA978452B/xx unknown
- 1997-09-22 AR ARP970104348A patent/AR008848A1/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0283261A2 (en) * | 1987-03-19 | 1988-09-21 | Zeneca Limited | Herbicidal substituted cyclic diones |
| EP0563817A2 (de) * | 1992-03-31 | 1993-10-06 | Hoechst Aktiengesellschaft | Salze von 2-Benzoyl-cyclohexandionen, Selektive herbizide Mittel, Verfahren zu ihrer Herstellung und ihre Verwendung zur Unkrautbekämpfung |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ334547A (en) | 2000-09-29 |
| WO1998012180A1 (de) | 1998-03-26 |
| HUP9903186A3 (en) | 2002-01-28 |
| SK26199A3 (en) | 2000-03-13 |
| HUP9903186A2 (hu) | 2000-02-28 |
| ATE234817T1 (de) | 2003-04-15 |
| EP0931070B1 (de) | 2003-03-19 |
| PL332212A1 (en) | 1999-08-30 |
| CN1230951A (zh) | 1999-10-06 |
| KR20010029525A (ko) | 2001-04-06 |
| EP0931070A1 (de) | 1999-07-28 |
| IL128744A0 (en) | 2000-01-31 |
| DE59709582D1 (de) | 2003-04-24 |
| BR9711407A (pt) | 1999-08-17 |
| ZA978452B (en) | 1999-03-19 |
| CA2266526C (en) | 2008-11-18 |
| JP4386465B2 (ja) | 2009-12-16 |
| EA199900273A1 (ru) | 1999-12-29 |
| JP2001501924A (ja) | 2001-02-13 |
| DE19638486A1 (de) | 1998-03-26 |
| US6479436B1 (en) | 2002-11-12 |
| AR008848A1 (es) | 2000-02-23 |
| CA2266526A1 (en) | 1998-03-26 |
| AU736395B2 (en) | 2001-07-26 |
| AU4383397A (en) | 1998-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |