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Carboxamides, their preparation and their use as herbicides

  • US 5,258,357 A
  • Filed: 09/21/1992
  • Issued: 11/02/1993
  • Est. Priority Date: 10/07/1989
  • Status: Expired due to Fees
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1. A carboxamide of the formulae Ia, Ib and Ic ##STR59## where:

  • X is oxygen;

    R1 is hydrogen;

    C3 -C8 -cycloalkyl which may carry from one to three of the following radicals;

    halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy and/or C1 -C4 -haloalkoxy;

    C1 -C6 -alkyl which may carry from one to three of the following radicals;

    hydroxyl, halogen, C3 -C8 -cycloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylthio, C1 -C4 -haloalkylthio, C1 -C4 -alkylamino, di-C1 -C4 -alkylamino and/or C3 -C6 -cycloalkylamino and/or a radical ##STR60## where R is cyano;

    nitro;

    halogen;

    C1 -C4 -alkyl;

    C1 -C4 -haloalkyl;

    C1 -C4 -alkoxy;

    C1 -C4 -haloalkoxy;

    C2 -C4 -alkynyloxy;

    C1 -C4 -alkylthio;

    C1 -C4 -haloalkylthio;

    C3 -C6 -alkoxycarbonylalkoxy and/or C1 -C4 -alkoxycarbonyl andm is 0, 1, 2 or 3, and the radicals R may be different when m is 2 or 3;

    R2 is hydroxy;

    C1 -C4 -alkoxy;

    C2 -C6 -cyanoalkyl;

    C3 -C6 -alkenyl, C3 -C6 -alkynyl, phenyl or naphthyl, where these groups may carry from one to three of the radicals stated for R;

    a 5- or 6-membered heterocyclic structure containing one or two heteroatoms selected from the group consisting of 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-pyrrolyl, 4-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl and 2-(4,6-dimethylprimidinyl), where this ring may carry one or two of the following radicals;

    halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy and/or C1 -C4 -alkylthio;

    one of the organic groups stated for R1 orR1 and R2 and the N-atom to which they are attached form a 4- to 7-membered ring which, in addition to methylene groups, may contain one of the following groups as a ring member;

    oxygen, sulfur, N-methyl or carbonyl;

    R3 and R4 are each nitro;

    cyano;

    halogen;

    amino which carries one or two C1 -C4 -alkyl groups and/or a C1 -C4 -alkylcarbonyl group;

    C1 -C4 -alkoxy or C1 -C4 -alkylthio, where these groups may carry from one to nine halogen atoms;

    a 5- or 6-membered heterocyclic structure containing one or two heteroatoms selected from the group consisting of 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-pyrrolyl, 4-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl and 2-(4,6-dimethylprimidinyl), where this ring may carry one or two of the following radicals;

    halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy and/or C1 -C4 -alkylthio;

    C2 -C6 -alkenyl, C2 -C6 -alkynyl, phenyl, phenoxy or phenylthio, were these groups may carry from one to three of the radicals stated for R, orone of the groups stated for R1 ;

    R5 is formyl, 4,5-dihydrooxazol-2-yl or a group COYR6 ;

    Y is oxygen or sulfur;

    R6 is hydrogen;

    C3 -C8 -cycloalkyl;

    C1 -C6 -alkyl which may carry from one to five halogen atoms or hydroxyl groups and/or one of the following radicals;

    cyano, aminocarbonyl, carboxyl, trimethylsilyl, C1 -C4 -alkoxy, C1 -C4 -alkoxy-C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -alkylamino, di-C1 -C4 -alkylamino, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, C1 -C4 -alkoxycarbonyl, C2 -C4 -alkoxycarbonyl-C1 -C3 -alkoxy, C2 -C4 -alkoxycarbonyl-C1 -C5 -alkoxycarbonyl, C1 -C4 -alkylaminocarbonyl, di-C1 -C4 -alkylaminocarbonyl, di-C1 -C4 -alkylphosphonyl, C1 -C4 -alkyliminoxy, phenyl, thienyl, benzyloxy, benzylthio, furyl, tetrahydrofuryl, phthalimido, pyridyl and/or benzoyl, where the cyclic radicals in turn may carry from one to three of the radicals stated for R;

    C3 -C6 -alkenyl, C3 -C6 -alkynyl or C5 -C7 -cycloalkenyl, where these groups may carry one of the following radicals;

    hydroxy, halogen, C1 -C4 -alkoxy or phenyl, and the phenyl radical in turn may carry from one to three of the radicals stated for R;

    phthalimido;

    tetrahydrophthalimido;

    succinimido;

    maleimido;

    benzotriazolyl;

    phenyl which may carry from one to three of the radicals stated for R;

    a group --N═

    CR7 R8, whereR7 is hydrogen or C1 -C6 -alkyl andR8 is C3 -C6 -cycloalkyl, phenyl, furyl or a radical R7 orR7 and R8 and the C-atom to which they are attached form a 4- to 7-membered alkylene ring, and ifR5 is carboxyl, methoxycarbonyl or ethoxycarbonyl and R2 is hydrogen, R3 is not hydrogen and R4 is not hydrogen or methyl, and ifR5 is carboxyl, methoxycarbonyl or ethoxycarbonyl and R4 is hydrogen, R3 is not hydrogen and R2 is not one of the following groups;

    hydrogen;

    C1 -C4 -alkyl;

    phenyl;

    2-(3,4-dimethoxyphenyl)ethyl or 2,5-dichlorothien-3-yl,and their agriculturally suitable salts.

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