Patent GB-926234-A (GB)
Title: Phosphonic and thiophosphonic acid esters
IPC: C07F9/6518
Filed: 1960-03-28
Abstract: The invention comprises phosphonic and thiophosphonic acid esters of the general formula:-(R1)(R2O)P(X)YA wherein R1 is an unsubstituted or substituted phenyl radical, an alkyl radical containing up to 8 carbon atoms, an alkenyl radical, an ethoxyvinyl radical or a cycloalkyl radical, R2 is an alkyl radical containing up to 4 carbon atoms, X and Y stand for oxygen or sulphur atoms and A stands for the grouping (a):-C(R4)=CH-R3 wherein R4 is an alkyl or alkoxy radical containing up to 4 carbon atoms and R3 is a cyano or alkyl-carbonyl group, the alkyl radical of which contains up to 4 carbon atoms, or when R4 is an alkoxy radical containing up to 4 carbon atoms R3 may also stand for an aminocarbonyl or alkoxycarbonyl group, the alkoxy radical of which contains up to 4 carbon atoms; or for the grouping: (b):- <FORM:0926234/IV(a)/1> wherein R5 is an alkyl radical containing up to 4 carbon atoms, R6 is an alkyl radical containing up to 4 carbon atoms or an alkylmercapto radical containing up to 4 carbon atoms, or the grouping:-(c): <FORM:0926234/IV(a)/2> wherein R7 is a hydrogen atom or an alkyl radical containing up to 4 carbon atoms and R8 is a hydrogen atom, an alkyl radical containing up to 4 carbon atoms or a phenyl radical,; or the grouping:-(d): <FORM:0926234/IV(a)/3> wherein R9 and R10 are alkyl radicals containing up to 4 carbon atoms.  They may be obtained by reacting an appropriate enolisable keto or thioketo compound with an appropriate O-alkyl thionophosphonic acid halide or phosphonic acid halide.  The reaction is preferably carried out with the alkali metal salts of the enolic compounds or by using the enolic compounds in the presence of alkali metal hydroxides, preferably in an inert organic solvent at room temperature or at slightly elevated temperature.  Several examples are given typical products being:- <FORM:0926234/IV(a)/4> The products have insecticidal properties (see Group VI).ALSO:An insecticidal composition contains, in conjunction with an inert solid or liquid diluent or carrier, a compound of the general formula (R1)(R2O)P(X)YA wherein R1 is an unsubstituted or substituted phenyl radical, an alkyl radical containing up to 8 carbon atoms, or an alkenyl, ethoxyvinyl or cycloalkyl radical, R2 is a C1-C4 alkyl radical, X and Y are oxygen or sulphur atoms and A stands for the grouping (a)-C(R4) = CH-R3 wherein R4 is an alkyl or alkoxy radical containing up to 4 carbon atoms and R3 is a cyano group or alkylcarbonyl group the alkyl radical of which contains up to 4 carbon atoms, or when R4 is an alkoxy radical containing up to 4 carbon atoms R3 may also stand for an aminocarbonyl or alkoxycarbonyl group, the alkoxy radical of which contains up to 4 carbon atoms; or for the grouping <FORM:0926234/VI/1> wherein R5 is a C1-C4 alkyl radical, R6 is a C1-C4 alkyl radical or an alkylmercapto radical containing up to 4 carbon atoms; or for the grouping <FORM:0926234/VI/2> wherein R7 is a hydrogen atoms or C1-C4 alkyl radical and R8 is a hydrogen atom, an alkyl radical containing up to 4 carbon atoms or a phenyl radical; or for the grouping <FORM:0926234/VI/3> wherein R9 and R10 are C1-C4 alkyl radicals (see Group IV (b)).  A typical composition is obtained by mixing the compound <FORM:0926234/VI/4> with acetone, adding benzoyl hydroxy diphenyl polyglycol ether as emulsifier and then diluting with water.