Patent GB-923701-A (GB)
Title: New organic phosphorus compounds and their manufacture and use
IPC: C07F9/32
Filed: 1961-02-23
Abstract: The invention comprises organo-phosphorus compounds of the general formula:- <FORM:0923701/IV(a)/1> in which R and R1 each represent an aliphatic hydrocarbon, cycloalkyl, aralkyl, aryl or heterocyclic residue which may be substituted, or R and R1 together form part of a ring system, R2 is an aralkyl or alkyl residue interrupted by at least one oxygen or sulphur atom, R3 is a hydrogen atom, a halogen atom or an alkyl residue, R4 is an aliphatic, alicyclic, aromatic, or heterocyclic residue and R5 is a hydrogen atom, an alkyl residue, or the same residue as R2, X and Y each represent -O-, -S-, -NH-, or -N(R)- wherein R is as defined above, Z is an oxygen or sulphur atom, and n and m p  each represent 1 or 2.  They may be obtained (a) by reacting a compound of the formula:- <FORM:0923701/IV(a)/2> in which R6 is an alkyl or chloroalkyl residue of 1 to 4 carbon atoms with a compound of the formula:- <FORM:0923701/IV(a)/3> in which Hal is a halogen atom, e.g. Cl or Br, the condensation being accompanied by the splitting off of a compound R6Hal, and (b) by reacting a compound of the formula:- <FORM:0923701/IV(a)/4> in which Me is an alkali metal, e.g. Na, with a compound of the formula:- <FORM:0923701/IV(a)/5> in which Hal is as defined above.  Also, compounds in which R3 is a hydrogen atom or an alkyl residue may be obtained by carrying out the following condensation:- <FORM:0923701/IV(a)/6> where in R, R1, R2, R4 and R5, X, Y, Z and m and n are as defined above, R3 is hydrogen or alkyl, Me is an alkali metal and Hal is a halogen atom.  The aliphatic residues which R and R1 may represent include methyl, octadecyl, allyl and 2-chloroethyl groups and the aromatic residues which R and R1 may represent include phenyl, 2- or 4-chlorophenyl, 2,4-dichlorophenyl, 4-methyoxyphenyl, 4-nitrophenyl, naphthyl and 4-diphenyl residues.  Other specified R and R1 groups include cyclohexyl, benzyl and tetrahydrofurfuryl.  The residue R2 may suitably be methoxy(ethoxy, propoxy or butoxy)ethyl radical or a phenoxyethyl group.  Specified R4 radicals include methyl, ethyl, phenyl, chlorophenyl and nitrophenyl groups and furfuryl and tetrahydrofurfuryl groups.  The reaction components are generally heated to 50 to 200 DEG C. and an inert solvent may be present.  The reactions may also be carried out in an atmosphere of an inert gas, e.g. nitrogen and/or under reduced pressure.  Several examples are given and the products have pesticidal properties (see Group VI).ALSO:A pesticidal composition contains, in admixture with a carrier therefor, a compound of the formula <FORM:0923701/VI/1> wherein R and R1 each represent an aliphatic hydrocarbon, cycloalkyl, aralkyl, aryl, or heterocyclic residue which may be substituted, or R and R1 together form part of a ring system, R2 is an aralkyl or alkyl residue interrupted by at least one oxygen or sulphur atom, R3 is a hydrogen atom, a halogen atom, or an alkyl residue, R4 is an aliphatic, alicyclic, aromatic, or heterocyclic residue and R5 is a hydrogen atom, an alkyl residue, or the same residue as R2, X and Y each represent-O- -S-, -NH-, or -N(R)- wherein R is as defined above, Z is an oxygen or sulphur atom and n and m each represent 1 or 2 (see Group IV (b)).  The carrier may be solid, liquid or gaseous and the composition may be in the form of a solution, paste, suspension or emulsion, which may be prepared with water and/or an organic solvent e.g. alcohol, acetone, methyl cyclohexanol, benzene, kerosene, petroleum, or a tar distillate or may be in the form of a dusting preparation. The composition may contain, in addition to the usual diluents, other additives such as sulphite cellulose waste liquor or cellulose derivatives or wetting or adhesive agents.  Other insecticides or fungicides may also be present.  The active ingredient may also be used in vapour form as a fumigant.