Herbicidal picolinamide derivatives

Details Herbicidal picolinamide derivatives Herbicidal picolinamide derivatives

1995-08-04

1998-01-13

Fan, Jane

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

5462761, A01N 4356, C07D40102

Patent

active

057079323

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/EP93/02925 filed Oct. 21, 1993 now WO 94/08991 Apr. 28, 1994.
The invention relates to certain pyrazolyloxypicolinamide derivatives, process for their preparation, compositions containing such compounds and their use as herbicides to combat undesired plant growth.
The herbicidal activity of 2-phenoxy-3-pyridine carboxamide compounds is well known. In 1981 and 1982 three U.S. patent specifications were published, U.S. Pat. Nos. 4,251,263, 4,270,946 and 4,327,218, directed to A. D. Gutman's work on 2-phenoxynitcotinamide herbicides. His later review articles, Chapter 5 of "Synthesis and Chemistry of Agrochemicals" (1987) published by the American Chemical Society, shows that his investigations started with 2-phenoxynicotinic acids (which were found to be inactive) progressed to N-alkyl amide derivatives (found to have weak herbicidal activity), and then concentrated on N-phenyl and N-benzyl amides as the most active of the compound type. Indeed, diflufenican carboxamide! was subsequently developed, by a different research group, as a commercial herbicide for use against broad-leaved weeds in winter cereals, such as winter wheat and barley.
U.S. Pat. No. 4,251,263 is concerned with the N-alkyl amides of Gutman, and related N-alkenyl and N-alkynyl amides. The compound documented as being the most active of the aliphatic amides prepared and tested is N-(1,1-dimethylprop-2-ynyl)-2-(3-trifluoromethylphenoxy)-3-pyridine carboxamide, which gives 85% control pre-emergence and only 57% control post-emergence on specified narrow- and broad-leaved species.
EP-A-0488474 discloses herbicidal 2-phenoxy-6-pyridine carboxamide compounds of the general formula: ##STR2## wherein n is an integer from 1 to 5 and the or each X independently represents a hydrogen or halogen atom, an alkyl group optionally substituted by one or more of the same or different substituents selected from halogen atoms and cyano, hydroxy and alkoxy groups, or a cyano, nitro, alkenyloxy, alkynyloxy, alkylthio, haloalkylthio or alkylnylthio group; a halogen atom or an alkyl or haloalkyl group; alkyl group optionally substituted by one or more of the same or different substituents selected from halogen atoms or hydroxy, cyano, alkoxy, alkylthio, alkoxycarbonyl, or mono- or di-alkylamino groups, an alkenyl, alkynyl, cycloalkyl, or optionally substituted cycloalkylalkyl group, or a hydroxy, alkoxy, alkenyloxy, alkynyloxy, alkoxycarbonyl, amino, mono- or di-alkylamino, alkoxycarbonylamino group, an arylamino group optionally substituted by a halogen atom, or a dialkylcarbamoyl group; or optionally interrupted by an oxygen or sulphur atom or by a group --NR-- in which R represents a hydrogen atom or an alkyl group.
It has now been found that certain new pyrazolyloxy-picolinamide compounds show excellent herbicidal activity against representative narrow- and broad-leaved test species in pre- and/or post-emergence application, certain examples exhibiting 90 to 100% effectiveness against test species both pre- and post-emergence.
The present invention therefore relates to compounds of the general formula I ##STR3## in which Z represents an oxygen or sulphur atom, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl or alkaryl group or one but not both of R.sup.1 and R.sup.2 may additionally represent a hydroxy group or an optionally substituted alkoxy, alkenyloxy,.alkynyloxy, alkylcarbonyl, amino, mono- or di-alkylamino, alkoxycarbonylamino, arylamino, arylalkylamino or dialkylcarbamoyl group, or together R.sup.1 and R.sup.2 represent an alkylene chain which is optionally interrupted by an oxygen or sulphur atom or by a group --NH-- in which R represents a hydrogen atom or an alkyl group, alkoxy, alkylthio, dialkylamino or haloalkyl group, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, alkaryl, alkoxy, dialkylcarbamoyl, acyl or cyano group, and atom, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, alkaryl, alkoxy, amino, mono- or di-alk

REFERENCES:
patent: 4251263 (1981-02-01), Gutman
patent: 4772309 (1988-09-01), Stetter et al.

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