Patent GB-885789-A (GB)
Title: 2, 3-dimercaptoquinoxaline derivatives
IPC: C07F9/68
Filed: 1959-07-03
Abstract: Derivatives of 2,3-dimercaptoquinoxaline or its substitution products of general formula <FORM:0885789/IV (b)/1> where Ph represents a substituted or unsubstituted fused benzene or naphthalene nucleus, A represents two acyl radicals, or one hydrogen and one acyl radical, or one =CO, =CS, =CNR1 (R1 being an alkyl or aryl radical), =S, or =SO group, and where the acyl radicals include also esterified carboxylic and thiocarboxylic acid groups, carboxylic acid amide groups and chlorinated alkyl thio groups have acaricidal and ovicidal effects and may be mixed with inert solid or liquid carrier such as chalk, talc or bentonite to form pesticidal compositions.  The 2,3-dimercaptoquinoxaline is reacted with mono-functional acid halides or anhydrides, such as carboxylic, thiocarboxylic, sulphenic, sulphinic, sulphonic and carbamic acid halides, chloroformic, chlorosulphonic acid esters, thio carboxylic acid ester halides, or chlorosulphonic acid amides, bifunctional acid halides such as phosgene, thiophosgene, thionyl or sulphuryl chloride which yield cyclic derivatives, and isocyanates or isothiocyanates, by the usual procedures in aqueous medium or water immiscible solvents, in the presence of alkali metal, or alkaline earth metal hydromides or carbonates, or of tertiary amines, or in the case of acid halides in inert organic solvents. Examples describe the reaction of disodium salts of 2,3dimercaptoquinoxaline and phenyl substituted derivatives thereof such as chloro-, mono- and di-methyl, methoxy, carbamoyl, dimethylcarbamoyl, sulphamoyl, dimethylsulphamoyl, and phenyl sulphamoyl and chloronaphthalene derivatives, with chloroformic acid methyl, ethyl, allyl, benzyl, and phenyl esters, or iron chloroformic acid phenyl ester, phosgene and thiophosgene, thio-carbonic acid ethyl ester chloride, dimethyl carbamic or thio-carbamic acid chloride, thionyl chloride, benzoyl chloride, phenyl isocyanate, perchloromethyl mercaptan, phenyl isocyanate dichloride, and sulphur dichloride.  2,3-dimercaptoquinoxaline is prepared by treating 2,3-dichloroquinoxaline or its derivatives with aqueous solutions of potassium or sodium sulphohydrate at an elevated temperature below 100 DEG C.ALSO:Pesticidal compositions contain as the active ingredient, at least one 2,3-dimercaptoquinoxaline derivative of general formula <FORM:0885789/VI/1> where Ph represents a substituted or unsubstituted fused benzene or naphthalene nucleus, A represents two acyl radicals, or one hydrogen and one acyl radical, or one =CO, =CS, =CNR1 (R1 being an alkyl or aryl radical), =S, or =SO group, and where the acyl radicals include also esterified carboxylic and thiocarboxylic acid groups, carboxylic acid amide groups and chlorinated alkyl thio groups (Group IV (b)), and an inert solid or liquid carrier.  In liquid form the active substance with equal parts of dimethyl formamide and an emulsifier (e.g. an aryl polyglycol ether) are diluted with water, and in solid form chalk, talc or bentonite may be added and the powder slurried if desired with the addition of emulsifiers.  The compounds have activity against various insects, especially spider mites, and Tetranychus telarius and althaeae and Paratetranychus pilosus are mentioned.