CHIRAL 3-(BENZYLSULFINYL)-5,5-DIMETHYL-4,5-DIHYDROISOXAZOLE AND 5,5-DIMETHYL-3-[(1H-PYRAZOL-4-YLMETHYL) SULFINYL]-4,5-DIHYDROISOXAZOLE DERIVATIVES, METHODS FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS

摘要

Optically active 3-sulfinyl-5,5-dimethyl-4H-isoxazole derivatives (I) and their salts or quaternary nitrogen derivatives, are new. Optically active 3-sulfinyl-5,5-dimethyl-4H-isoxazole derivatives of formula (I) and their salts or quaternary nitrogen derivatives, are new. Y 1> : substituted benzene group of formula (a) or pyrazole group of formula (b); R 1>-R 8> : H, halo, OH, CN, nitro, amino, C(O)OH, formyl, (1-6C)-alkyl, (1-6C)-haloalkyl, (1-6C)-alkylcarbonyl, (1-6C)-haloalkylcarbonyl, (1-6C)-alkylcarbonyloxy, (1-6C)- haloalkylcarbonyloxy, (1-6C)-alkylcarbonyl-(1-4C)-alkyl, (1-6C)-haloalkylcarbonyl-(1-4C)-alkyl, (1-6C)-alkylcarbonyl-(1-4C)-haloalkyl, (1-6C)-haloalkylcarbonyl-(1-4C)-haloalkyl, (1-6C)-(halo)alkoxy, (1-6C)-(halo)alkoxycarbonyl, (1-6C)-(halo)alkoxycarbonyl-(1-6C)-alkyl, (1-6C)-(halo)alkoxycarbonyl-(1-6C)-haloalkyl, (2-6C)-(halo)alkenyl, (2-6C)-(halo)alkenylcarbonyl, (2-6C)-(halo)alkenyloxy, (2-6C)-(halo)alkenyloxycarbonyl, (2-6C)-(halo)alkynyl, (2-6C)-(halo)alkynylcarbonyl, (2-6C)-(halo)alkynyloxy, (2-6C)-(halo)alkynyloxycarbonyl, (1-6C)(halo)alkylthiocarbonyl, (1-6C)(halo)alkylthiocarbonyloxy, (1-6C)-alkylthio-(1-6C)-alkoxy, (1-6C)-alkylthio-(1-6C)-alkylcarbonyl, (1-6C)-alkylthio-(1-6C) -alkylcarbonyloxy, (6-14C)-aryl, (6-14C)-aryloxy, (6-14C)-arylcarbonyl, (6-14C)-aryloxycarbonyl, (6-14C)-aryl-(1-6C)-alkyl, (6-14C)-aryl-(1-6C)-alkoxy, (6-14C)-aryloxy-(1-6C)-alkyl, (6-14C)-aryl-(1-6C)-alkyl-carbonyl, (6-14C)-aryl-(1-6C)-alkyl-carbonyloxy, (6-14C)-aryl-(1-6C)-alkoxycarbonyl, (6-14C)-aryl-(1-6C)-alkoxycarbonyloxy, (1-6C)-alkylsulfonyl, (1-6C)-alkylthio, (1-6C)-alkylsulfinyl, (1-6C)-haloalkylsulfonyl, (1-6C)-haloalkylthio, (1-6C)-haloalkylsulfinyl, (1-6C)-alkylsulfony-(1-6C)-alkyl, (1-6C)-alkylthio-(1-6C)-alkyl, (1-6C)-alkylsulfinyl-(1-6C)-alkyl, (1-6C)-haloalkylsulfonyl-(1-6C)-alkyl, (1-6C)-haloalkylthio-(1-6C)-alkyl, (1-6C)-haloalkylsulfinyl-(1-6C)-alkyl, (1-6C)-alkylsulfonyl-(1-6C)-haloalkyl, (1-6C)-alkylthio-(1-6C)-haloalkyl, (1-6C)-alkylsulfinyl-(1-6C)-haloalkyl, (1-6C)-haloalkylsulfonyl-(1-6C)-haloalkyl, (1-6C)-haloalkylthio-(1-6C)-haloalkyl, (1-6C) -haloalkylsulfinyl-(1-6C)-haloalkyl, (1-6C)-alkylsulfonyloxy, (1-6C)-haloalkylsulfonyloxy, (4-14C)-arylsulfonyl, (6-14C)-arylthio, (6-14C)-arylsulfinyl, mono-((1-6C)-alkyl)-amino, mono-((1-6)-haloalkyl)-amino, di-((1-6C)-alkyl)-amino, di-((1-6C)-haloalkyl)-amino, ((1-6C)-alkyl-(1-6C)-haloalkyl)-amino, N-((1-6C)-alkanoyl)-amino, N-((1-6C)-haloalkanoyl)-amino, aminocarbonyl-(1-6C)-alkyl, mono-(1-6c)-alkylaminocarbonyl-(1-6C)-alkyl, di-(1-6C)-alkylaminocarbonyl-(1-6C)-alkyl, mono-((1-6C)-alkyl)-aminocarbonyl, (1-6C)-alkoxy-(1-6C)-alkyl, (1-6C)-alkoxy-(1-6C)-alkoxy, (1-6C)-alkyoxycarbonyl-(1-6C)-alkoxy, (3-8C)-cycloalkyl, (3-8C)-cycloalkoxy, (3-8C)-cycloalkyl-(1-6C)-alkyl, (3-8C)-cycloalkyl-(1-6C)-haloalkyl, (3-8C)-cycloalkyl-(1-6C)-(halo)alkoxy, (3-8C)-cycloalkylcarbonyl, (3-8C)-cycloalkoxycarbonyl, (3-8C)-cycloalkyl-(1-6C)-(halo)alkylcarbonyl, (3-8C)-cycloalkyl-(1-6C)-(halo) alkoxycarbonyl, (3-8C)-cycloalkylcarbonyloxy, (3-8C)-cycloalkoxycarbonyloxy, (3-8C)-cycloalkyl(1-6C)-(halo)alkylcarbonyloxy, (3-8C)-cycloalkyl(1-6C)-(halo)alkoxylcarbonyloxy, (3-8C)-cycloalkenyl, (3-8C)-cycloalkenyloxy, (3-8C)-cycloalkenyl-(1-6C)-(halo)alkyl, (3-8C)-cycloalkenyl-(1-6C)-(halo)alkoxy, (3-8C)-cycloalkenylcarbonyl, (C3-C8)-cycloalkenyloxycarbonyl, (3-8C)-cycloalkenyl-(1-6C)-(halo)alkylcarbonyl, (3-8C)-cycloalkenyl-(1-6C)-(halo)alkoxycarbonyl, (3-8C)-cycloalkenylcarbonyloxy, (3-8C)-cycloalkenyloxycarbonyloxy,(3-8C)-cycloalkenyl-(1-6C)-alkylcarbonyloxy, (3-8C)-cycloalkenyl-(1-6C)-haloalkylcarbonyloxy, (3-8C)-cycloalkenyl-(1-6C)-alkoxycarbonyloxy, (3-8C)-cycloalkenyl-(1-6C)-haloalkoxycarbonyloxy, (3-8C)-cycloalkylthio, (3-8C)-alkenylthio, (3-8C)-cycloalkenylthio, (3-6C)-alkynylthio, hydroxy-(1-6c)-alkyl, hydroxy-(1-6C)-alkoxy, cyano-(1-6c)-alkoxy, cyano-(1-6C)-alkyl, 3-oxetanyloxy, pyrimidinyl-2-yl, 4,6-dimethoxypyrimidinyl-2-yl or C(O)NR 9>R 1> 0>; and either R 9>, R 1> 0> : H, (1-6C)-alkyl, (3-6C)-cycloalkyl or (1-6C)-haloalkyl; or R 9>R 1> 0> : (1-6C)-alkylene group, which contains O or S or one or two amino or (1-6C)-alkylamino group, where the mentioned residues can be cyclically linked among each other and/or two ortho substituents together forms (1-6C)-alkylene group, which contains one or more O and/or S, where the 1-6C alkylene groups can be one or more time substituted by halogen and the respective halogen substituted can be same or different and the cycloalkyl or aryl residue can be substituted one or more times and independently from one another. Independent claims are included for: (1) the preparation of (I); and (2) a composition comprising (I). [Image] [Image] ACTIVITY : Herbicide; Plant Growth Regulant; Insecticide; Antimicrobial; Fungicide; Antibacterial; Virucide. MECHANISM OF ACTION : None given.