Triazinyl compounds with herbicidal activity

Details Triazinyl compounds with herbicidal activity Triazinyl compounds with herbicidal activity

1994-02-15

1996-01-09

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

540362, 540363, 540454, 540524, 544 60, 544195, 544214, 544113, 544211, 544212, 544213, 544194, 544218, 544219, 504196, 504197, 504219, 504221, 504225, 504230, 504231, C07D25146, C07D25130, C07D40312, A01N 4366

Patent

active

054829208

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP93/01393 filed Jun. 3, 1993.
The present invention relates to novel, herbicidally active pyrimidinyl-oxy- and triazinyl-oxy- and -thio-propionic acid derivatives, to processes for the preparation thereof, to compositions comprising them as active ingredients, and to the use thereof in controlling weeds, especially selectively in crops of useful plants.
Pyrimidinyl-oxy- and triazinyl-oxy- and -thio-acetic acid derivatives having herbicidal action are generally known. Such compounds are described, for example, in European Patent Applications Nos. 0 347 811, 0 400 741, 0 409 368, 0 481 512 and 0 517 215. Novel herbicidally active pyrimidinyl-oxy- and triazinyl-oxy- and -thio-propionic acid derivatives have now been found.
The pyrimidinyloxy- and triazinyloxy- and pyrimidinylthio- and triazinylthio-propionic acid derivatives according to the invention have the formula I ##STR4## wherein ##STR5## A is a group ##STR6## Y is oxygen or sulfur; Z is methine or nitrogen; methylthio, ethylthio, methylamino, ethylamino, dimethylamino or diethylamino; allcyl mono-substituted by chlorine or mono- to hexa-substituted by fluorine; phenyl, thienyl, or phenyl or thienyl mono- or di-substituted by fluorine, chlorine, methyl or by methoxy; --(CH.sub.2).sub.n --; C.sub.3-6 alkenyloxy, C.sub.3-6 -alkynyloxy, C.sub.3-4 cycloalkyl-C.sub.1-2 alkoxy, C.sub.4-6 cycloalkoxy, C.sub.1-4 alkoxy mono-substituted by cyano, phenyl, C.sub.1-2 alkoxy or chlorine or mono- to hexa-substituted by fluorine; C.sub.1-6 alkylthio or cyano; --(CH.sub.2).sub.p --, --CH.dbd.CH--CH.dbd.CH--, --N--CH--CH.dbd.CH-- or --S--CH.dbd.CH--; --, --CH.sub.2 CH(OH)CH.sub.2 --, --CH.sub.2 SCH.sub.2 -- or --CH.sub.2 CH.sub.2 SCH.sub.2 --; formyl, cyano, phosphono, phosphino, methylphosphino or a group COX, substituted by hydroxy, C.sub.1-4 -alkoxy, mercapto, C.sub.1-4 alkylmercapto, vinyl, phenyl, 4-hydroxyphenyl, 4-imidazolyl, 3-indolyl, carboxy, C.sub.1-4 alkoxycarbonyl, 2-propenyloxycarbonyl, cyano, carbamoyl, methylphosphino or by methylsulfoximino; ethynyl, vinyl, phenyl, or vinyl or phenyl substituted by chlorine, methyl or by methoxy; heterocyclic ring which may in turn contain a nitrogen atom, an oxygen atom, a sulfur atom or a group --S(O)--, --S(O).sub.2, --C(O)--, --C(O)O--, --C(O)S-- --C(S)O-- or --C(S)S-- and/or may additionally be mono- or poly-substituted by C.sub.1-6 alkyl or mono-substituted by benzyl, C.sub.1-3 alkoxy, hydroxy-C.sub.1-2 alkyl or by C.sub.1-2 alkoxy-C.sub.1-2 alkyl; di-substituted by fluorine, chlorine, bromine, iodine, C.sub.1-4 alkyl, trifluoromethyl, C.sub.1-3 alkoxy, difluoroalkoxy, cyano, nitro or by C.sub.1-4 alkoxycarbonyl; pyridyl, or pyridyl mono- or di-substituted by fluorine, chlorine, methyl, methoxy or by trifluoromethyl; C.sub.1-4 alkylamino, C.sub.2`4 -dialkylamino or a group ##STR7## R.sub.16 is hydroxy, C.sub.1-4 alkoxy, 2-propenyloxy, benzyloxy, amino or a further amino acid group (X.sub.1); the salts of those compounds of formula I having a free carboxy group; with the proviso that R.sub.4 are methyl, R.sub.5 is hydrogen, hydrogen or methyl; with the exception of the compounds N-.beta.-[2-(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-methyl-butyryl]-dimethylh ydrazide and N-[2-(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-methyl-butyryl]-hydrazide.
If the compounds of formula I contain an asymmetric centre, the compounds may occur in optically isomeric forms. Some of the compounds of formula I may occur in mutomeric forms (for example keto-enol tautomerism). If an aliphatic C.dbd.C double bond is present it is also possible for geometrical isomerism (E form or Z form ) to occur. This applies especially to those compounds of formula I wherein Q is Q.sub.2. Formula I therefore includes all possible stereoisomers that occur in the form of enantiomers, mutomers, diastereoisomers, E/Z isomers or mixtures thereof.
In formula I the alkyl, alkenyl and alkynyl radicals may be straight-chain or branched. The same applies also to the or each alkyl moiety of alkoxy-, alkylthio- and alkoxycarbonyl-containing

REFERENCES:
Chem. Abst. 116:59390u, p. 865, 1992, Wada et al.

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