GB850984A - Thiophosphoric acid esters - Google Patents

Abstract

The invention comprises thiophosphoric acid esters of the formula: <FORM:0850984/IV(b)/1> wherein R, R1 and R2 are C1-C4 alkyl radicals and R3 is hydrogen or a C1-C4 alkyl radical and wherein R1 and R2 may also form a ring system, e.g. piperidine or morpholine, with the nitrogen atom, and Z is oxygen or sulphur. They may be obtained by reacting a haloalkyl sulphonic acid dialkylamide of the formula: Hal,CH2,CH(R3),SO2,N(R1)(R2) with an appropriate dialkylthiol- or dialkyl thionothiol-phosphoric acid, the acid being either free in which case the reaction is carried out in the presence of an acid binding agent, or being in the form of a salt, e.g. the sodium or ammonium salt. The reaction may be effected in an inert organic solvent, e.g. an alcohol, aliphatic ketone or aromatic hydrocarbon, and suitable reaction temperatures are between room temperature and the boiling point of the solvent used. Examples are given for the production of compounds in which Z is sulphur, each R is ethyl, R3 is hydrogen and N(R1)(R2) is N(CH3)2, piperidino, and morpholino and of the compounds of the formula (C2H5O)2P(O)SCH2,CH2, SO2N(CH3)2, (C2H5O)2P(S)S,CH2,CH(CH3) SO2 N(CH3)2, (CH3O)2P(S)SCH2 CH2SO2N(CH3)2, ((CH3)2CHO)2P(S)S,CH2,CH2 ,SO2N(CH3)2 and the corresponding thiolo phosphoric acid derivative, and ((CH3)2CHO)2P(S)SCH2CH2,SO2N (C2H5)2. The products are useful as insecticide (see Group VI). Starting materials: Cl,CH2CH2,S,N(CH3)2 is obtained by reacting b -chlorethyl sulphenic acid chloride with dimethylamine and is then treated with potassium permanganate in the presence of magnesium sulphate and acetone to form the compound Cl,CH2,CH2,SO2N(CH3)2. The latter on treatment with sodium iodide in methyl ethyl ketone at 80 DEG C followed by the oxidation of acetone yields I,CH2,CH2,CH2,SO2N(CH3) 2.ALSO:An insecticidal composition comprises as active ingredient one or more thiophosphoric acid esters of the formula <FORM:0850984/VI/1> wherein R, R1 and R2 are C1-C4 alkyl, or R1 and R2 may form a ring system, e.g. piperidine or morpholine, with the nitrogen atom, R3 is hydrogen or C1-C4 alkyl, and Z is oxygen or sulphur (see Group IV(b)) and a solid or liquid carrier or diluent. Specified carriers are talc, chalk, bentonite, clay, water (if desired with an emulsifier e.g. benzyl hydroxy diphenyl polyglycol ether), dimethyl formamide, alcohols ketones, and liquid hydrocarbons. The active ingredient may be used in conjunction with known insecticides and/or fertilisers. Typical active ingredients are <FORM:0850984/VI/2> and the corresponding 0,0-diisopropyl dithiophosphate.