Patent GB-970581-A (GB)
Title: New insecticidal thiophosphoric acid esters and their manufacture
IPC: A01N57/10
Filed: 1961-02-24
Abstract: The invention comprises organo-phosphorus compounds of the general formula: <FORM:0970581/C1/1> in which R and R1 each represents an alkyl, cycloalkyl, aralkyl, aryl or heterocyclic residue which may contain substituents and in the case of an alkyl residue may be interrupted by at least one oxygen atom, R2 is a residue of the formula <FORM:0970581/C1/2> or of the formula <FORM:0970581/C1/3> in which m is a whole number from 2 to 4 and n and p each represents a whole number from 1 to 4, R3 is a hydrogen atom, an alkyl residue or the same residue as R2, or when R3 is hydrogen R2 may additionally represent -CH2.CH(OA)2 wherein A is an alkyl residue of at most 4 carbon atoms, R4 is one of the groups -CH2-, -CH2-CH2-, and -CH(R5)- in which R5 is a C1-C4 alkyl group and X is an oxygen or sulphur atom. They may be obtained (a) by reacting a compound of the formula (RO)(R1O)P(X)SMe wherein Me is a salt-forming cation, e.g. an alkali metal ion, with a compound of the formula Hal.R4CON(R2)(R3) in which Hal is a halogen atom, e.g. Br or Cl, or (b) by reacting a compound of the formula: (RO)(R1O)P(X)S.R4.COOR6 in which R, R1, R4 and X are as defined above and R6 is a C1-C4 alkyl group with a compound of the formula H-N(R2)(R3) in which R2 and R3 are as defined above. Reaction (a) may suitably be effected at from 0 to 110 DEG C. and an inert solvent may be present, e.g. an alcohol or ketone.  The reaction may also be carried out in an inert atmosphere e.g. of nitrogen and reduced pressure may be used; also a two phase system consisting of water and an organic solvent e.g. methylene chloride may be used.  General examples are given and the products have pesticidal properties (see Division A5).ALSO:A pesticidal composition comprises a solid, liquid, or gaseous diluent or carrier and an organo-phosphorus compound of the formula <FORM:0970581/A5-A6/1> in which R and R1 each represents an alkyl, cycloalkyl, aralkyl, aryl or heterocyclic residue which may contain substituents and in the case of an alkyl residue may be interrupted by at least one oxygen atom, R2 is a residue of the formula <FORM:0970581/A5-A6/2> or of the formula <FORM:0970581/A5-A6/3> in which m is a whole number from 2 to 4 and n and p each represents a whole number from 1 to 4, R3 is a hydrogen atom, an alkyl residue or the same residue as R2, or when R3 is hydrogen R2 may additionally represent -CH2CH(OA)2, wherein A is an alkyl residue of at most 4 carbon atoms, R4 is one of the groups -CH2-, -CH2-CH2-, and -CH(R5)- in which R5 is a C1-4 alkyl group and X is an oxygen or sulphur atom (see Division C2).  The composition may be in the form of a dusting or spraying preparation which may contain the usual inert fillers, sulphite cellulose waste liquor or cellulose derivatives. The composition may be an aqueous solution or an aqueous emulsion which may contain an organic solvent and the usual wetting or adherent agents or may be in the form of a powder, aqueous paste or dispersion, or self-dispersing oil.  The active ingredient may also be used in vapour form as a fumigant.  Other insecticides and/or fungicides may also be present.