Carboxamides and their use as herbicides
First Claim
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.
1 Assignment
0 Petitions
Accused Products
Abstract
Carboxamides of the formulae Ia to Ic ##STR1## where X is oxygen or sulfur;
R1 is hydrogen or substituted or unsubstituted cycloalkyl or alkyl;
R2 is hydroxy, alkoxy, cyanoalkyl, substituted or unsubstituted alkenyl, alkynyl, phenyl or naphthyl, or one of the groups stated for R1 ;
R3 and R4 are nitro, cyano, halogen, substituted or unsubstituted amino, alkoxy, alkylthio, substituted or unsubstituted alkenyl, alkynyl, phenyl, phenoxy or phenylthio, or one of the groups stated for R1 ;
R5 is formyl, 4,5-dihydrooxazol-2-yl or COYR6 (Y═O,S);
R6 is hydrogen, cycloalkyl, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkenyl or phenyl,
phthalimido, tetrahydrophthalimido, succinimido, maleimido, benzotriazolyl or
a group --N═CR7 R8, where
R7 and R8 are hydrogen or alkyl, and R8 may also be cycloalkyl, phenyl, or R7 and R8 together form a 4- to 7-membered alkylene chain;
and if R5 is carboxyl, methoxycarbonyl or ethoxycarbonyl and R2 is hydrogen, R3 is not hydrogen and R4 is not hydrogen or methyl, and if R5 is carboxyl, methoxycarbonyl or ethoxycarbonyl and R4 is hydrogen, R3 is not hydrogen or R2 is not one of the following groups: hydrogen, C1 -C4 -alkyl, phenyl, 2-(3,4-dimethoxyphenyl)ethyl or 2,5-dichlorothien-3-yl;
processes for the manufacture of compounds I and herbicidal agents containing them.
20 Citations
15 Claims
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1. A carboxamide of the formula Ia, Ib and Ic ##STR60## where X is sulfur;
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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 R1 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; 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, or one 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 and R8 is C3 -C6 -cycloalkyl, phenyl or a radical R7 or R7 and R8 together form a 4- to 7-membered alkylene chain, and if R5 is carboxyl, methoxycarbonyl or ethoxycarbonyl and R2 is hydrogen, R3 is not hydrogen and R4 is not hydrogen or methyl, and if R5 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. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15)
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Specification