GB822477A - Thiophosphoric acid esters and a process for their production - Google Patents

Abstract

The invention comprises thiophosphoric acid esters of the formula <FORM:0822477/IV (a)/1> in which R is an alkyl radical, especially a C1-C4 alkyl radical, R1 is an aliphatic or aromatic radical and X is oxygen or sulphur, at least one X being sulphur. They may be obtained by reacting a 3-aliphatic (or aromatic)-mercapto - 1 - cyano - isopropyl alcohol with a halide of an O,O-dialkyl thiophosphoric acid or by reacting a 3-aliphatic (or aromatic) mercapto-1-cyano isopropyl halide with a salt (e.g. an alkali metal or ammonium salt) of an O,O-dialkyl thiol (or thionothiol-) phosphoric acid or with the free acid in the presence of an acid-binding agent. The first-mentioned reaction yields compounds in which one X is oxygen and is preferably carried out in an inert organic solvent and in the presence of an acid binding agent, especially a tertiary amine such as pyridine. The second type of reaction is also advantageously carried out in the presence of an inert organic solvent. Specified reaction temperatures in each case are between 0 DEG and 150 DEG C. Examples are given for the production of compounds in which each R is C2H5, each X is sulphur and R1 is C2H5, and CH (CH3)2 respectively and the compounds <FORM:0822477/IV (a)/2> and <FORM:0822477/IV (a)/3> The products are stated to be effective as insecticides (see Group VI). The compound C2H5SCH2CH(OH)(CH2CN) used as a starting material is obtained by adding g -chloro-b -hydroxy butyronitrile to a solution of potassium hydroxide and ethyl mercaptan in methanol and removing the precipitated potassium chloride. The compounds p-CH3.C6H4.SCH2CH(OH)(CH2CN) and (CH3)2CH.SCH2CH(OH)CH2CN are obtained similarly using p-thiocresol and isopropyl mercaptan respectively instead of ethyl mercaptan. Also the chlorides corresponding to each of these mercapto alcohols are obtained by reacting the latter with thionyl chloride in the presence of chloroform.ALSO:An insecticidal composition comprises a solid or liquid carrier and one or more thiophosphoric acid esters of the formula <FORM:0822477/VI/1> in which R is an alkyl radical, especially a C1-C4 alkyl radical, R1 is an aliphatic or aromatic radical, and X is oxygen or sulphur, at least one X being sulphur (see Group IV (b)). A specified composition comprises an aqueous solution comprising the compound <FORM:0822477/VI/2> acetone and benzyl hydroxy diphenyl polyglycol ether as emulsifier. Other liquid diluents specified are methanol, ethanol, methyl ethyl ketone and liquid hydrocarbons. Known insecticides and/or fertilizers may also be present.