Pyrimidinyl and triazinyl herbicides

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

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Details

504242, 504243, 544319, 544327, 544333, 544334, 544335, C07D23926, C07D40106, A01N 4354

Patent

active

053170059

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention concerns new pyrimidine and triazine derivatives having herbicidal activity, processes for their preparation, and compositions containing them.


DESCRIPTION In one aspect, the invention provides the pyrimidine and
triazine derivatives of the formula: ##STR2## and salts thereof, where: X represents --CH' or --N.dbd.; or heterocyclyl group; hydrogen, alkyl, alkoxy, amino, alkylamino, dialkylamino or halogen.
Any alkyl moiety present in the molecule is preferably of 1 to 6 carbon atoms, especially of 1 to 4 carbon atoms. Specific preferred unsubstituted alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl and t-butyl.
When Y represents a substituted alkyl group, it may be substituted for example by one or more halogen atoms (eg fluorine, chlorine or bromine atoms), by cyano, by alkoxy of 1 to 4 carbon atoms (eg methoxy or ethoxy), or by a group --COZ, where Z is a group --NR'R" or --OR' in which R' and R" each represent hydrogen or a substituted or unsubstituted alkyl or phenyl group.
When R.sup.1 represents a substituted alkyl group, it may be substituted for example by one or more halogen atoms (eg fluorine, chlorine or bromine atoms), by cyano, by phenyl, by alkoxy of 1 to 4 carbon atoms (eg methoxy or ethoxy), or by a group --COZ, where Z is a group R', --NR'R" r --OR' in which R' and R" each represent hydrogen or a substituted or unsubstituted alkyl or phenyl group.
When R.sup.1 represents a cycloalkyl group, it is preferably of 3 to 7 carbon atoms, especially cyclopentyl or cyclohexyl, and is desirably unsubstituted.
When R.sup.1 represents a substituted phenyl group, it is preferably substituted by one or more halogen atoms, eg fluorine, chlorine or bromine, nitro groups, substituted or unsubstituted amino groups (eg alkylamino, dialkylamino or acylamino groups, especially where the alkyl moiety has from 1 to 4 carbon atoms), cyano groups, alkyl or alkoxy groups of 1 to 4 carbon atoms (eg methyl, ethyl, methoxy or ethoxy), alkoxycarbonyl groups in which the alkyl moiety is of 1 to 4 carbon atoms (eg methoxycarbcnyl or ethoxycarbonyl), or phenoxy groups.
When R.sup.1 represents a heterocyclyl group, it is preferably of 5 or 6 ring atoms, at least one of which is desirably sulphur, oxygen or nitrogen. Preferred such heterocyclic groups include furyl, pyridyl and, especially, thienyl groups. Specific preferred groups are 2-furyl, 2-pyridyl and, particularly, 2-thienyl. If desired, the heterocycle may be substituted, for example by one or more alkyl groups of 1 to 4 carbon atoms.
When R.sup.2, R.sup.4 or R.sup.5 represents halogen, it is preferably fluorine, chlorine or bromine.
The salts of the compounds of formula I are preferably those formed on the nitrogen atom of the sulphonylamino group with an alkali-metal or ammonium cation, eg sodium, potassium, or isopropylammonium.
Specific preferred groups which R.sup.1 may represent include ethyl, n-propyl, isopropyl, s-butyl, 3,3-dimethyl-2-oxcbutyl, 1,3,3-trimethyl-2-oxobutyl, dimethylcarbamcylmethyl, 1-(methoxycarbonyl)el--hyl, 1-(t-butyloxycarbonyl)ethyl, 1-(dimethylcarbamoyl)ethyl, 1-phenylethyl, cyclohexyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 2-cyanophenyl, 3-triflucromethylphenyl, 2-methylphenyl, 3-methylphenyl, 4-aminophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 2-methoxycarbonylphenyl, 2-ethoxycarbonylphenyl and 2-thienyl.
Specific preferred groups which R.sup.2 may represent include hydrogen, methyl, ethyl, n-propyl and isopropyl.
Specific preferred groups which Y may represent include methyl, cyanomethyl, chloromethyl, trifluoromethyl and dimethylamina.
Specific groups which R.sup.4 and R.sup.5 may represent include methylamino, dimethylamino and, more preferably, methyl, methoxy and chloro.
In a particularly preferred group of compounds of formula I, Y represents methyl, R.sup.1 represents isopropyl or phenyl, R.sup.2 represents hydrogen, and R.sup.4 and R.sup.5 both represent methoxy.
Specific preferred compounds according to the invention are those of the Examples provided hereinafter.
In ano

REFERENCES:
patent: 4962109 (1990-10-01), McDonald et al.
patent: 5053072 (1991-10-01), Ort et al.

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