2-(1H-Pyrazol-4-ylmethyl)-sulfonyl-oxazole derivatives, 2-(1H-pyrazol-4-ylmethyl)-sulfanyl-oxazole derivatives and chiral 2-(1H-pyrazol-4-ylmethyl)-sulfinyl-oxazole derivatives, method for production of same and their use as herbicides and plant growth regulators

摘要

2-[(1H-Pyrazol-4-yl-methyl)-sulfanyl]-oxazole derivatives (I) and their salts are new. 2-[(1H-Pyrazol-4-yl-methyl)-sulfanyl]-oxazole derivatives of formula (I) and their salts are new. R 1, R 2e.g. (1-6C)-alkyl, (1-6C)-alkylcarbonyl, (1-6C)-alkylcarbonyl-(1-4C)-alkyl, (1-6C)-alkylcarbonyloxy, (1-6C)-alkoxy, (1-6C)-alkoxycarbonyl (all optionally substituted), H, halo, nitro or CN; R 3-R 5e.g. (1-6C)-alkyl, (1-6C)-haloalkyl, (1-6C)-alkylcarbonyl, (1-6C)-haloalkylcarbonyl or (1-6C)-alkylcarbonyloxy, (1-6C)-haloalkylcarbonyloxy, (1-6C)-alkylcarbonyl-(1-4C)-alkyl or (1-6C)-haloalkylcarbonyl-(1-4C)-alkyl (all optionally substituted, where: the adjacent residues R 4and R 5are optionally cyclically bonded and/or forms (1-6C)alkylene group optionally containing O and/or S, and the (1-6C)-alkylene group is optionally substituted by halo), H, halo, OH, CN, nitro, amino, C(O)OH or formyl; and n : 0-2, preferably 1. Full Definitions are given in the DEFINITIONS (Full Definitions) Field. Independent claims are included for: (1) the preparation of (I); (2) the preparation of thioether compound of formula (II), comprising (a) reacting 2-mercaptooxazole or an oxazol-2-(3H)-thione or its salt of formula (V), (Va), (Vb) or (Vc) with (1H-pyrazol-4-yl-methyl) derivative of formula (VI) in the presence of an alkali or alkaline earth metal base or an organic base in a solvent; or reacting an oxazole derivative of formula (VII) with [(1H-pyrazol-4-yl-methyl)]-imidothiocarbamate salt of formula (VIII), in stew procedure, in the presence of an aqueous alkali- or alkaline earth metal base or an alkali metal- or alkaline earth metal carbonate base and a solvent; or reacting (VII) with (1H-pyrazol-4-yl-methyl)mercaptane compound of formula (IX) in the presence of an alkali or alkaline earth metal base; or halogenating or nitrating an oxazole derivative of formula (X) to obtain (II) (in which R 1is halo or NO 2); or reacting (1H-pyrazol-4-yl-methyl)disulfide derivatives of formula (XV) with 2-amino-oxazole compound of formula (XIV) and a diazotizing agent; and (3) a composition comprising (I). Lg, Lg1 : a leaving group. [Image] [Image] [Image] [Image] [Image] ACTIVITY : Plant Growth Regulant; Fungicide; Antibacterial; Virucide; Herbicide. MECHANISM OF ACTION : None given.