Patent GB-921121-A (GB)
Title: New dialkyl phosphorothionic acid derivatives and pesticidal compositions containing them
Inventor: PIANKA MAX
IPC: C07F9/165
Filed: 1958-11-06
Abstract: The invention comprises compounds having the general formula (RO)(R1O)P(S)OCH2CO.NR3.COOR2 in which R and R1 are the same or different C1-C4 alkyl groups, R2 is an aliphatic hydrocarbon group which may be substituted by one or more of the following substituents:-halogen atoms e.g. Cl or F, amino groups, substituted amino groups, nitro groups, alkoxy groups, alkylthio groups, sulphoxy groups and sulphonyl groups, said aliphatic hydrocarbon groups containing not more than 12 carbon atoms, or is an araliphatic hydrocarbon group, a substituted araliphatic hydrocarbon group, an alicyclic group, or a naphthyl group or a substituted naphthyl group, and R3 is hydrogen, an aliphatic group which may be substituted or an alicyclic group, said group R3 containing not more than 9 carbon atoms.  The invention also comprises acid addition salts of basic compounds of the above general formula, e.g. hydrochlorides or hydrogen oxalates.  The preferred compounds are those in which R2 is a C1-C12 alkyl group, a C3-C12 alkenyl group, a benzyl group, a p-nitro benzyl group, a naphthyl group, a b -chloroethyl group, a b -fluoroethyl group, a b -ethoxyethyl group, a b -ethylthioethyl group, or a dimethyl (or diethyl) amino ethyl group and R3 is hydrogen, a C1-C4 alkyl group or a C3 alkenyl group.  The compounds may be obtained by reacting a compound of the formula Y-CH2.CONR3COOR2 in which R2 and R3 are as defined above and Y is Cl, Br or I, the process being carried out in the presence of an acid binding agent where X is hydrogen.  Suitable acid binding agents are sodium or potassium carbonate, and tertiary bases such as pyridine and triethylamine. The reaction temperature should not exceed 100 DEG C. otherwise isomerisation of the products occurs with formation of compounds of the general formula O:P(OR)(OR1)S.CH2CONR3COOR2 wherein R, R1, R2 and R3 are as defined above.  The latter compounds may thus be obtained by heating the compounds of the invention at temperatures above 100 DEG C.  Several examples are given and the products have pesticidal properties (see Group VI). Specification 811,677 also is referred to.ALSO:A pesticidal composition comprises, in association with a carrier or diluent, a compound of the general formula (RO)(R1O)P(S)OCH2CONR3COOR2 in which R and R1 are the same or different C1-C4 alkyl groups, R2 is an aliphatic hydrocarbon group which may be substituted by one or more of the following: halogen atoms, amino or substituted amino groups, nitro groups, alkoxy groups, alkylthio groups, sulphoxy groups and sulphonyl groups, said aliphatic hydrocarbon group containing not more than 12 carbon atoms, or is an araliphatic hydrocarbon group, a substituted araliphatic hydrocarbon group, an alicyclic group or a substituted or unsubstituted naphthyl group, and R3 is a hydrogen, a substituted or unsubstituted aliphatic group, or an alicyclic group, said group R3 containing not more than 9 carbon atoms, or acid addition salts of basic compounds of such formula, e.g. hydrochlorides or hydrogen oxalates.  The composition may be in the form of a solution or emulsion, aerosol, or solid or semisolid preparation, or in the form of a fumigating composition in which the active compound is associated with a solid pyrotechnic component.  The active compound may also be used in admixture with other non-basic insecticides and/or non-basic fungicides.  Specification 811,677 also is referred to.