Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1993-07-09
1995-03-28
Ford, John M.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544320, 544323, 544332, 504242, 504243, C07D23947, C07D23942, C07D23948, A01N 4354
Patent
active
054017106
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention concerns sulfonamidopyrimidines and sulfonamidotriazines having herbicidal activity, processes for their preparation and herbicidal compositions containing them.
PRIOR ART
In European Patent Specification No 155872, there are described certain arylsulfamoyl acetic acid derivatives useful for reducing the lignin content of crop plants so as to make the plants more nutritious and palatable for animals.
DESCRIPTION
I have now found that certain related compounds, many of which are new, surprisingly have good herbicidal activity which may make them of use as herbicides, and particularly as selective herbicides, in agriculture.
Accordingly, in one aspect, this invention provides a herbicidal composition which comprises one or more compounds of the formula: ##STR2## or salts thereof, where: A is --CH.dbd. or --N.dbd.; alkyl, alkanoyl or alkoxycarbonyl; each represent hydrogen, substituted or unsubstituted alkyl, or one of R.sup.7 and R.sup.8 represents substituted amino;
In another aspect, the invention provides per se the compounds of formula I in which R.sup.5 represents isopropyl, and/or X represents methoxycarbonyl, and salts thereof.
In a further aspect, the invention provides a method of combating weeds at a locus infested or liable to be infested therewith which comprises applying to said locus an effective amount of one or more compounds of formula I or salts thereof.
Any alkyl group present in the compound of formula I is preferably of 1 to 6 carbon atoms, especially of 1 to 4 carbon atoms. Specific preferred unsubstituted alkyl or alkyl-containing groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, methoxy, ethoxy and n-propoxy. When the alkyl group may be substituted, it is preferably substituted for example by one or more halogen atoms, e.g. fluorine, chlorine or bromine, or by alkoxy groups of 1 to 4 carbon atoms, e.g. methoxy or ethoxy. Specific preferred substituted alkyl-containing groups include chloromethyl, bromomethyl, dichloromethyl, trifluoromethyl, difluoromethoxy, methoxyethyl and ethoxyethyl.
Any alkenyl or alkynyl group in the compound of formula I is preferably of 2 to 6 carbon atoms, for example allyl or propargyl.
Any halogen atom present in the compound of formula I is preferably fluorine, chlorine or bromine.
When R.sup.5 represents an aryl group, it is preferably a substituted or unsubstituted phenyl group. When substituted, it is preferably substituted by one or more halogen atoms, e.g. chlorine, fluorine or bromine atoms, nitro groups, substituted or unsubstituted amino groups (e.g. alkylamino, dialkylamino or acylamino groups, especially where the alkyl moieties have from 1 to 4 carbon atoms), cyano groups, or alkyl or alkoxy groups of 1 to 4 carbon atoms, e.g. methyl, ethyl, methoxy or ethoxy.
A preferably represents --CH.dbd..
R.sup.1 is preferably chloro, methoxy, ethoxy or dimethylamino.
R.sup.2 is preferably methoxy or ethoxy.
In a particularly preferred group of compounds of formula I, R.sup.1 and R.sup.2 are both methoxy.
R.sup.3 is preferably hydrogen, methyl, ethyl, allyl, propargyl, acetyl or methoxycarbonyl, particularly hydrogen.
R.sup.4 is preferably hydrogen.
R.sup.5 is preferably isopropyl.
X is preferably carboxy, methoxycarbonyl, ethoxycarbonyl, carbamoyl or methylcarbamoyl, particularly methoxycarbonyl.
The salts of the compounds of formula I are preferably those formed with alkali-metals, e.g. lithium, sodium or potassium, or organic bases, e.g. amines such as cyclohexylamine or piperidine.
Specific preferred compounds according to the invention are those of the Examples provided hereinafter. Particular mention may, however, be made of methyl 2-(4,6-dimethoxypyrimidin-2-ylsulfamoyl)-3-methylbutanoate, the salts thereof, and the analogues thereof wherein R.sup.3 is other than hydrogen, which break down in use to the compound where R.sup.3 is hydrogen.
The compounds of the invention where R.sup.3 represents hydrogen and X is a group --CO.sub.2 R.sup.6 can be prepared by a process in which a compound
REFERENCES:
Gilmore, Chemical Abstracts, vol. 93, entry 239328v (1980).
Lespagnol, Chemical Abstracts, vol. 64, entry 6649g (1966).
Ford John M.
Schering Agrochemicals Limited
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