Patent GB-875583-A (GB)
Title: New organic phosphorus compounds and their manufacture and use
IPC: C07F9/12
Filed: 1957-10-21
Abstract: The invention comprises compounds of the formula:  <FORM:0875583/IV (b)/1> in which R, R1 and R2 are alkyl, alkenyl, cycloalkyl, aralkyl, aryl, or heterocyclic residues, which may contain substituents, and of which R and R1 may together form part of a ring system, R3 is hydrogen, alkyl, or halogen atom, R4 is an alicyclic, aromatic, or heterocyclic residue with the proviso that when R4 is an unsubstituted aromatic residue and X, Y and Z simultaneously stand for oxygen, R3 must be either an alkyl residue or a halogen atom and with the further proviso that when R3 is a hydrogen atom or an alkyl residue and X, Y and Z each simultaneously stand for oxygen, no residue of an aliphatic alcohol containing at least one oxygencontaining group in the molecule additional to the hydroxyl group may be present in the molecule, X and Y are -O-, -S-, -NH or -N-R and Z is oxygen or sulphur, and n and m each represent the whole number 1 or 2, or compounds of the general formula <FORM:0875583/IV (b)/2> in which R, R1, R2, R3, X, Y, Z, n and m are as defined above. The products may have either of the given formulae or may be isomeric mixtures of compounds of the two formulae depending on the method of preparation.  They may be obtained by condensing a compound of the formula <FORM:0875583/IV (b)/3> in which R5 is a C1-C4 alkyl radical and the other symbols are as defined above with a compound of the formula <FORM:0875583/IV (b)/4> in which R2, R3 and R4 are as defined abov and Hal is a halogen atom, e.g. bromine or chlorine or by reacting a compound of the formula <FORM:0875583/IV (b)/5> in which Me is an alkali metal, e.g. sodium, with a compound of the formula <FORM:0875583/IV (b)/6> Compounds in which R3 is a hydrogen atom or an alkyl group may also be obtained by the following condensation: <FORM:0875583/IV (b)/7> Reaction is generally effected by heating the reactants at raised temperature, e.g. 50-200 DEG C., and an inert solvent may be present, e.g. benzene, toluene, xylene, chlorobenzene or benzine.  The reaction may be carried out in an inert gas e.g. nitrogen and/or under reduced pressure.  The radicals R and R1 may be the same or different and those specified include various alkyl radicals, allyl and 2-chlorethyl and radicals containing thiocyano, cyano, or ester groups, 2- or 4-chlorophenyl, 2:4 dichlorophenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-diphenyl, and tetrahydrofuryl and the R4 radical includes phenyl, cyclohexyl, furyl, tetrahydrofuryl, chlorophenyl and nitrophenyl. Several examples are given.  The products have pesticidal properties (see Group VI).ALSO:A pesticidal composition comprises in admixture with a liquid or solid diluent an organophosphorus compound of the formula <FORM:0875583/VI/1> or of the formula <FORM:0875583/VI/2> in which R, R1 and R2 are alkyl, alkenyl, cycloalkyl, aralkyl, aryl, or heterocyclic residues, which may contain substituents, and of which R and R1 may together form part of a ring system, R3 is hydrogen, alkyl, or halogen, R4 is alicyclic, aromatic or heterocyclic, with the proviso that when R4 is an unsubstituted aromatic residue and X, Y and Z each simultaneously stand for oxygen, R3 must either be an alkyl group or a halogen atom, and with the further proviso that when R3 is hydrogen or alkyl and X, Y and Z each simultaneously stand for oxygen, no residue of an aliphatic alcohol containing at least one oxygen-containing group in the molecule additional to the hydroxyl group may be present in the molecule, X and Y are -O-, -S-, -NH-, or <FORM:0875583/VI/3> Z is O or S, and n and m each represent the integer 1 or 2 (see Group IV (b)).  The composition may be in the form of a dusting powder, fumigating preparation, or spraying liquor, e.g. in the form of a solution or suspension in water or an organic solvent such as ethanol, petroleum or a tar distillate and a wetting agent may be present.  Specified inert fillers are kaolin, talc, chalk, sulphur, gypsum, bentonite, sulphite cellulose waste liquor, and cellulose derivatives.  Other insecticides and/or fungicides may also be present.  Other organic solvents specified are methanol, isopropanol, butanol, acetone, methyl ethyl ketone, methyl-cyclohexanol, benzene, toluene, xylene and kerosene.