Abstract:
The invention comprises compounds of the general formula:- in which R and R1 are C1-C4 alkyl groups, X is an oxygen or sulphur atom and Y is C1-C4 alkoxy, allyloxy, phenoxy, nitrophenoxy, mono-or dialkylamino with 1 to 4 carbon atoms in the alkyl groups, cycloalkylamino, anilino, pyrrolidino, piperidino, C1-C4 alkylmercapto, C1-C4 alkyl sulphonyl, phenylmercapto or phenyl sulphonyl group. They may be obtained by reacting a compound of the formula (RO) (R1O) P(X) Hal in which Hal is a halogen atom, e.g. chlorine, bromine, or iodine, and R, R1 and X are as defined above with a 1-substituted butene-(3)-ol-(2) of the formula HO.CH.(CH2Y).CH =CH2 in which Y is as defined above. The reation may be carried out in the presence of an inert organic diluent, e.g. an aromatic, aliphatic or cycloaliphatic hydrocarbon or an aliphatic chlorohydrocarbon and it is advantageous to effect the reaction in the presence of an agent which binds hydrogen halide, e.g. pyridine, aniline, methylaniline, triethylamine, tripropylamine or other amine whose boiling point is above the reaction temperature or an alkali metal carbonate or bicarbonate. The reaction is preferably effected at about 10 to 130 DEG C. e.g. at 15 to 75 DEG C. Examples are given for the production of compounds in which R and R1 are each ethyl, X is S and Y is -NHC3H7, N(C2H5)2, SC2H5, p.NH.C6H5. p.SO2C6H5, SO2C2H5, phenoxy, cyclooctylamino, pyrrolidine, p.S.C6H5, ethoxy, allyloxy, and p.nitrophenoxy respectively. Examples are also given for the production of (CH3O)2P(S)O.CH(CH2SC2H5) CH=CH2 and the corresponding O,O- diisopropyl and O,O-dibutyl compounds, (CH3O)2 P(O)O CH(CH2.O. C6H5)CH=CH2, (iso C3H7O)2 P(S)OCH (CH2S.C6H5) CH=CH2, and (C2H5O)2 P(O)O CH(CH2SC2H5)CH=CH2. The products have insecticidal properties.