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Carboxamides and their use as herbicides

  • US 5,201,934 A
  • Filed: 10/03/1990
  • Issued: 04/13/1993
  • Est. Priority Date: 10/07/1989
  • Status: Expired due to Fees
First Claim
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1. A carboxamide of the formula Ia, Ib and Ic ##STR60## where X is sulfur;

  • 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 ##STR61## 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;

    orone of the organic groups stated for R1R3 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;

    C2 -C6 -alkenyl, C2 -C6 -alkynyl, phenyl, phenoxy or phenylthio, where 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 urn 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 or a radical R7 orR7 and R8 together form a 4- to 7-membered alkylene chain, 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,or their agriculturally suitable salts.

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