Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-05-08
1998-06-02
Grumbling, Matthew V.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544405, 544406, 544407, C07D24118, C07D40112, C07D40312, A01N 4360
Patent
active
057599564
DESCRIPTION:
BRIEF SUMMARY
This is a 35 U.S.C. .sctn.371 application of PCT/EP94/01759 filed May 26, 1994.
The present invention relates to herbicidal compounds, and in particular to herbicidal carboxamide derivatives, their preparation and their use.
European Patent Specification No. 0 488 474 A1 describes and claims phenoxypicolinamides of the general formula ##STR3## wherein n is an integer from 1 to 5 and the or each X independently represents a hydrogen or halogen atom, an alkyl or alkoxy 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, alkenylthio or alkynylthio 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.
Variation of the central ring of such compounds and of related pyridyloxy- and pyrazolyloxy- derivatives, to include additional hetero atoms have now been found to show high herbicidal activity. Useful intermediates to such new compounds have also been found to exhibit herbicidal properties.
The present invention accordingly provides a compound of the general formula ##STR4## wherein A represents a group of the general formula ##STR5## in which the or each X independently represents a halogen atom or an optionally substituted alkyl, alkoxy, aryl or aryloxy group, or an alkenyloxy, alkynyloxy, alkylthio, haloalkylthio, alkenylthio, alkenylthio, alkylsulphinyl, alkylsulphonyl or cyano group; and n is 0, an integer from 1 to 4, or, for the phenyl group, 5; or A represents a group of the general formula ##STR6## in which each of R.sup.4 , R.sup.5 and R.sup.6 independently represents a hydrogen or halogen atom, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, alkaryl, alkoxy, amino, mono- or di-alkylamino, alkoxycarbonylamino, arylamino, dialkylcarbamoyl, acyl or acylamido group or a cyano group, with the proviso that R.sup.5 and R.sup.6 do not represent an acyl, acylamido or cyano group; optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, aryl, aralkyl, alkaryl, hydroxy, alkoxy, alkenyloxy, alkynyloxy, alkylcarbonyl, alkoxycarbonyl, amino, mono- or di-alkylamino, alkoxycarbonylamino, arylamino, arylalkylamino or dialkylcarbamoyl group, or together represent an alkylene chain which is optionally interrupted by an oxygen or sulphur atom or by a group --N.sup.7 -- in which R.sup.7 represents a hydrogen atom or an alkyl group; and CR.sup.3 in which R.sup.3 represents a hydrogen atom or an optionally substituted alkyl, alkoxy, alkylthio or mono- or di-alkylamino group, provided that all three of Q.sup.1, Q.sup.2 and Q.sup.3 are not a nitrogen atom or the group CR.sup.3.
Generally, herein, any alkyl, alkenyl or alkynyl moiety which is or forms part of a group represented by X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 or R.sup.7 suitably contains up to 12 carbon atoms, conveniently up to 8, preferably up to 6, and especially up to 4, carbon atoms. Such moieties may be linear or branched chain moieties. As part of a larger group, alkyl moieties are especially methyl or ethyl.
A cycloalkyl moiety suitably contains from 3 to 10, preferably from 3 to 8, carbon atoms. An aryl group is usefully a single ring or fused ring system having from 6 to 14 ring members, preferably 6 or 10 ring atoms; a preferred aryl group is phenyl.
A heterocyclic group is suitab
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Nakamura et al., "Structure-Activity Relationship of Herbicidal 2,3-Dicvano-5-Substituted Pyrazines", Agric. Biol. Chem., 47(7), pp. 1555-1560, 1983.
Eisenacht Rudi
Niedermann Hans-Peter
American Cyanamid Company
Grumbling Matthew V.
Hill Gregory M.
Rao Deepak R.
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