Herbicidal thiazole derivatives

Details Herbicidal thiazole derivatives Herbicidal thiazole derivatives

1996-04-25

1997-12-02

Gerstl, Robert

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544133, 546280, 548188, C07D27756, A01N 4378

Patent

active

056935943

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP94/01758 filed May 26, 1994.
The present invention relates to thiazole derivatives, their preparation and their use as herbicides.
The present invention provides a compound of the general formula ##STR1## wherein
A represents a group of the general formula ##STR2## in which each X independently represents a halogen atom or an optionally substituted alkyl, cycloalkyl, alkoxy, aryl or aryloxy group, or an alkenyloxy, alkynyloxy, alkylthio, haloalkylthio, alkenylthio, alkynylthio, 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 ##STR3## 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.
Z represents an oxygen or sulphur atom;
R.sup.1 and R.sup.2 each independently represents a hydrogen atom or an 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 --NR-- in which R represents a hydrogen atom or an alkyl group; and
R.sup.3 represents a hydrogen or halogen atom or an alkyl group.
EP-A-0419944 discloses somewhat similar herbicidal thiazole derivatives but with different substitution at the 5-position of the thiazole ring.
EP-A-283762 also discloses herbicidal thiazole derivatives but lacking a carboxamide or thiocarboxamide group at the 4-position of the thiazole ring.
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 or R.sup.6, 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 suitably a single ring system having 5 or 6 ring members selected from carbon atoms and at least one nitrogen, oxygen or sulphur atom; preferred heterocyclic groups are morpholino and thienyl.
Halogen is used to denote fluorine, chlorine, bromine or iodine, especially chlorine or fluorine. A preferred haloalkyl moiety is trifluoromethyl.
An acyl group is the group formed by the removal of hydroxyl from a carboxyl group, and is used herein to include formyl and optionally substituted alkylcarbonyl and arylcarbonyl groups.
An alkylene chain suitably has from 3 to 6, preferably 4 or 5 chain members.
Optional substituents may be any of those customarily employed in the development of biocidal compounds, and/or the modification of such compounds to influence their activity, persistence, penetration or any other property. Specific examples of such substituents include halogen, especially fluorine, chlorine or bromine atoms, and phenyl, nitro, cyano, amino, hydroxy, alkyl, alkoxy, mono- or di-alkylamino groups, haloalkyl, haloalkoxy, cycloalkyl, formyl, alkoxycarbonyl, carboxy, halophenyl groups and heterocyclyl, especially thienyl, groups. Alkyl moieties of such optional substituents usefully have from 1 to 6 carbon atoms, preferably 1 or 2 carbon atoms.
Where A represents an optionally substituted phenyl or pyridyl r

REFERENCES:
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patent: 5244867 (1993-09-01), Ditrich et al.
patent: 5256633 (1993-10-01), Ditrich et al.
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