Herbicidal picolinamide derivatives

Details Herbicidal picolinamide derivatives Herbicidal picolinamide derivatives

1992-09-02

1994-12-06

Ivy, C. Warren

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

544124, 546 14, 546193, 546194, 546256, 546261, C07P21302, A01N 4340

Patent

active

053710614

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to certain new picolinamide derivatives, their preparation, herbicidal compositions containing them, and their use in combating undesired plant growth.
In accordance with the present invention there is provided a compound of the general formula: ##STR2## wherein R.sub.1 and R.sub.2 each independently represents a hydrogen atom, or an alkyl, aryl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl, alkaryl, hydroxy, alkoxy, alkenyloxy, alkynyloxy, alkylcarbonyl, alkoxycarbonyl, amino, mono- or di-alkylamino, alkoxycarbonylamino group, in which groups any alkyl, alkenyl, alkynyl, cycloalkyl or aryl moiety is optionally substituted, an optionally substituted heterocyclic group, an arylamino group optionally substituted by a halogen atom, a dialkylcarbamoyl group, a trialkylsilyl group or a fused ring structure, or together form an alkenylene chain or an optionally substituted alkylene chain which is optionally interrupted by an oxygen or sulphur atom or by a group --NR-- in which R represents a hydrogen atom or an alkyl group; R.sub.3 represents a hydrogen or halogen atom, or an alkyl, alkoxy, aryl or aryloxy group optionally substituted by one or more of the same or different substituents selected from halogen atoms and cyano, hydroxy and alkoxy groups, or represents a cyano, carboxy, alkoxycarbonyl, (alkylthio)carbonyl, alkylcarbonyl, amido, alkylamido, nitro, alkenyloxy, alkynyloxy, alkylthio, haloalkylthio, alkenylthio, alkynylthio, alkylsulphinyl, alkylsulphonyl, alkyloximinoalky1 or alkenyloximinoalkyl group; R.sub.4 represents a halogen atom or an alkyl or haloalkyl group; Z represents an oxygen or sulphur atom; m is 0-3; and n is 1-4.
Where substituted, any of the alkyl, alkenyl, alkynyl, cycloalkyl or aryl moieties in R.sub.1 and R.sub.2 may be substituted by one or more of the same or different substituents selected from halogen atoms and hydroxy, cyano, alkyl, alkoxy, alkylthio, alkoxycarbonyl, aryl, aryloxy, and mono- or di-alkylamino groups.
When any of the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents or contains an alkyl, alkenyl or alkynyl substituent group, this may be linear or branched and suitably has up to 12, preferably up to 6, carbon atoms. Preferred alkyl groups are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl and t-butyl. Where a cycloalkyl substituent group is present, this suitably has from 3 to 6 carbon ring atoms. An aryl group is suitably a phenyl group. An alkenylene or alkylene chain suitably has 3 to 6 chain members. A halogen atom suitably denotes a fluorine, chlorine or bromine atom; preferred haloalkyl groups are fluoroethyl, chloroethyl, trifluoromethyl and trifluoroethyl groups.
The substituent(s) R.sub.3 may be at any free position or combination of positions on the pyridyloxy ring.
Each substituent R.sub.3 is preferably a hydrogen, chlorine or bromine atom, or a methyl or trifluoromethyl group.
Preferably m is 0 and n is 1-2.
Preferably Z represents an oxygen atom.
The substituents R.sub.1 and R.sub.2 when individually present may be the same or different. Preferably R.sub.1 represents an unsubstituted C.sub.1-6 alkyl group, a C.sub.1-5 alkyl group substituted by an alkoxy, aryloxy or cyano group or by one or more halogen atoms, for example a trifluoroethyl group, a C.sub.1-6 alkoxy group optionally aryl-substituted, a C.sub.2-7 alkynyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkenyloxy group, an unsubstituted aryl group, especially a phenyl group, a substituted aryl group, especially a phenyl group substituted by one or more halogen atoms, an aralkyl group, especially a benzyl or phenethyl group, an alkaryl group, especially a tolyl group, a cycloalkyl group, especially a cyclopropyl or cyclopentyl group, a substituted cycloalkylalkyl group, a heterocyclic group, especially a furfuryl or substituted isoxazolyl group, a dialkylaminoalkyl group, a naphthyl group or a trimethylsilyl group, while R.sub.2 represents a hydrogen atom or an optionally substituted C.sub.1-6 alkyl group, especially a methyl

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