Substituted 1-(3-pyridinyl)pyrazol-4-yl-acetic acids, process for their preparation and their use as herbicide and plant growth regulator.

摘要

Use of substituted 1-(3-pyridinyl)pyrazol-4-yl-acetic acid compounds (I) or their salts as herbicide or plant growth regulator, is claimed. Use of substituted 1-(3-pyridinyl)pyrazol-4-yl-acetic acid compounds of formula (I) or their salts as herbicide or plant growth regulator, is claimed. R 1>H or OH; either R 2>, R 3>H, halo or 1-6C alkyl (optionally substituted with halo, 1-4C alkoxy, 1-4C alkylthio or 1-4C haloalkoxy); or CR 2>R 3>form an optionally saturated 3-6C carbocyclic ring (optionally substituted with halo or 1-4C alkyl); R 4>1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl (all optionally substituted with 3-9C cycloalkyl, 5-9C cycloalkenyl or 5-9C cycloalkynyl (all optionally substituted with halo, 1-4C (halo)alkyl, 2-4C alkenyl, 2-4C alkynyl, 1-4C (halo)alkoxy or 1-4C alkylthio), halo, CN, 1-4C (halo)alkoxy, 1-4C alkoxy-1-4C alkoxy, 1-4C alkylthio, 3-9C cycloalkyl (optionally substituted by halo, CN, 1-4C alkyl or 1-4C haloalkyl)), phenyl (optionally substituted with halo, CN, NO 2, carboxy, 1-4C (halo)alkyl, 2-4C alkenyl, 2-4C alkynyl, 1-4C (halo)alkoxy, 1-4C alkoxy-1-4C alkoxy, 1-4C alkylthio, 1-4C (halo)alkanoyl, [(1-4C)alkoxy]-carbonyl or [(1-4C)haloalkoxy]-carbonyl), 1-6C alkanoyl (optionally substituted by halo, CN, 1-4C (halo)alkoxy, 1-4C alkoxy-1-4C alkoxy or 1-4C alkylthio (optionally substituted with halo, CN, 1-4C alkyl or 1-4C haloalkyl substituted 3-6C cycloalkyl)), [(1-4C)alkoxy]-carbonyl (optionally substituted by halo, CN, 1-4C (halo)alkoxy, 1-4C alkoxy-1-4C alkoxy, 1-4C alkylthio (optionally substituted with halo, CN, 1-4C alkyl or 1-4C haloalkyl substituted (3-6C)cycloaklyl)), [(3-9C)cycloalkoxy]-carbonyl (optionally substituted with halo, 1-4C (halo)alkyl, 2-4C alkenyl, 2-4C alkynyl, 1-4C (halo)alkoxy or 1-4C alkylthio), H, halo or CN; R 5>3-60C aryl (optionally substituted) or 1-30C heteroaromatic ring (containing 1-4 ring heteroatom of N, O or S, and optionally substituted); R 6>1-6C haloalkylsulfonyl, 3-9C cycloalkyl or 5-9C cycloalkenyl (all optionally substituted with halo, 1-4C (halo)alkyl), halo, OH, amino, NO 2, carboxy, CN, carbamoyl, 1-6C (halo)alkyl, 1-4C alkoxy-1-4C alkyl, 1-4C alkylthio-1-4C alkyl, mono or di-[(1-4C)alkyl]-aminoalkyl, OH-(1-4C)alkyl, 2-6C (halo)alkenyl, 2-6C (halo)alkynyl, 1-6C (halo)alkoxy, 1-4C alkoxy-1-4C alkoxy, 1-6C alkylthio, [(1-6C)alkoxy]-carbonyl, [(1-6C)haloalkoxy]-carbonyl, 1-6C alkanoyl, 1-6C haloalkanoyl, mono- or di-[(1-4C) acyl]-N-[(1-6C)alkyl]-amino, (1-6C)alkylsulfinyl, 1-6C haloalkylsulfinyl or 1-6C alkylsulfonyl; and n : 0-4. An independent claim is included for the preparation of (I) comprising: reacting a pyridine hydrazine compound of formula (II) with a dimethyl-carbonyl-carboxyl compound of formula (R 4>-C(=O)-CH 2(-C(R 3>)(R 2>)-C(=O)-OR 1>)-C(=O)-R 5>) (III) to give (I); reacting a substituted pyridinyl-pyrazol compound of formula (IA) or (IB) with an alcohol compound of formula (R 1>-OH) to give (I) (where R 1> is H); and optionally converting (I) into its hydroxide salt. R : one of the residues of R 1> different from H, anhydride, acid halide or an activated ester of (Ia), or H. [Image] [Image] ACTIVITY : Herbicide. MECHANISM OF ACTION : None given.