Sulfinamide derivatives, a process for preparing the derivatives

Details Sulfinamide derivatives, a process for preparing the derivatives Sulfinamide derivatives, a process for preparing the derivatives

1982-09-07

1985-12-10

Chan, Nicky

Chemistry: fertilizers

Processes and products

Forms or conditioning

260456NS, 260940, 260941, A01N 5710, C07C14500, C07F 902

Patent

active

045577501

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to novel sulfinamide derivatives, a process for preparing the derivatives and herbicides containing the same.


BACKGROUND ART

Various types of herbicides have been developed heretofore in the fields of agriculture and horticulture, greatly contributing to the elimination or reduction of weeding work. Among these herbicides, there are known Paraquat (i.e. 1,1'-dimethyl-4,4'-bipyridiniumdichloride) and Glyphosate (i.e., N-phosphonomethylglycine) as useful compounds, particularly as nonselective post-emergence herbicides. However, these conventional herbicides, although markedly effective as herbicides under some conditions, suffer numerous defects when used in some other situations. Thus, it has been desired to provide new herbicides free from such drawbacks. For example, "Paraquat" is a fast-acting contact herbicide, but has herbicidal activity only for a short period of time and high toxicity. "Glyphosate" is a post-emergence translocation herbicide and maintains herbicidal activity for a prolonged period of time. But it has the defects of being slow-active and less effective in killing perennial broad-leaf weeds.


DISCLOSURE OF INVENTION

The sulfinamide derivatives of the present invention are novel compounds heretofore undisclosed in literature and represented by the formula ##STR3## wherein R.sub.1 represents an alkoxy (C.sub.1-6) carbonylmethyl group or cyanomethyl group; R.sub.2 represents a group ##STR4## (in which X and Y are each an alkyl group having 1-6 carbon atoms or alkoxy group having 1-6 carbon atoms and m and n are 0 or an integer of 1 to 3); and Ph represents phenyl.
Examples of the alkoxy (C.sub.1-6) carbonylmethyl groups represented by R.sub.1 in the formula 1 previously given are methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, isopropoxycarbonylmethyl, n-butoxycarbonylmethyl, tert-butoxycarbonylmethyl, n-pentyloxycarbonylmethyl, n-hexyloxycarbonylmethyl, etc. Examples of the alkyl groups having 1-6 carbon atoms and represented by X and Y are methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, etc. Examples of the alkoxy groups having 1-6 carbon atoms and represented by X and Y are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, n-pentyloxy, n-hexyloxy, etc.
The sulfinamide derivatives of this invention have post-emergence herbicidal activity with foliar application substantially without injury to crop plants such as orange and other fruit trees, mulberry trees, field crop plants, etc. These noxious weeds include, for example, Panicum crus-galli L., Amaranthus retroflexus L., Aeschynomene indica, Eclipta alba Hassk, Digitaria adscendens Henr. The derivatives of this invention are safely used because of their low toxicity to humans, other animals and fishes.
The sulfinamide derivatives of this invention can be easily prepared by the reactions schematically illustrated below. ##STR5##
In the foregoing equations, R.sub.1 and R.sub.2 are as defined above, Ph is a phenyl group and Hal is a halogen atom.
Examples of thionyl halides useful in this invention are thionyl chloride, thionyl bromide, etc.
Preferably the reactions of the equations (1) and (2) are carried out after adding to the reaction system a base useful for capturing a hydrogen halide being produced. Examples of solvents to be used in these reactions are diethyl ether, dibutyl ether, tetrahydrofuran, dioxane and like ethers, carbon tetrachloride, chloroform, methylene chloride and like halogenated hydrocarbons, etc. Bases to be used in the reactions include for example triethylamine, tributylamine, dimethylaniline, diethylaniline, N-ethylmorpholine and like tertiary amines, pyridines, etc.
The thionyl halide is used in the reaction of equation (1) in an amount of about 1 to about 1.5 moles, preferably about 1 to about 1.2 moles, per mole of the compound having the formula (II), although the proportions of the two compounds are not particularly limited but can be varied over a wide range. The amount of the base to be used, thou

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