Patent GB-892405-A (GB)
Title: New organic phosphorus compounds, and their manufacture and use
IPC: C07F7/28
Filed: 1959-07-10
Abstract: The invention comprises compounds of the general formula <FORM:0892405/IV (b)/1> in which R and R1 each represent an alkyl, alkenyl, cycloalkyl, aralkyl, aryl or heterocyclic radical which may be substituted or R and R1 together form part of a ring system, R2 is a branched or unbranched alkyl or alkylaryl radical interrupted by at least one oxygen or sulphur atom, preferably by at least two oxygen or sulphur atoms, R3 is a hydrogen or halogen atom or an alkyl radical, R4 is an aliphatic, alicyclic, aromatic, e.g. phenyl, chlorophenyl or nitrophenyl, or heterocyclic radical, X and Y each represent -O-, -S-, -NH-, or <FORM:0892405/IV (b)/2> Z is an oxygen or sulphur atom, and n and m each represent 1 or 2. They may be obtained (1) by reacting a compound of the formula <FORM:0892405/IV (b)/3> in which R5 is a C1-C4 alkyl group with a compound of the formula <FORM:0892405/IV (b)/4> in which Hal is halogen, e.g. Cl or Br, accompanied by the splitting off of a compound R5-Hal; (2) by reacting a compound of the formula <FORM:0892405/IV (b)/5> in which Me is an alkali metal, e.g. Na, with a compound of the formula <FORM:0892405/IV (b)/6> Compounds in which R3 is a hydrogen atom or an alkyl group can also be made by the following condensation <FORM:0892405/IV (b)/7> wherein Me and the other symbols present are as defined above. The reaction components are heated at a raised temperature, e.g. 50 DEG C.-200 DEG C., and an inert solvent, e.g. benzene, toluene, xylene, chlorobenzene or benzine may be present. If desired, the reaction may be carried out in an atmosphere of an inert gas, e.g. nitrogen and/or under reduced pressure.  The specified aliphatic radicals which R and R1 may represent may be substituted by chlorine, thiocyano, cyano or ester groups and substituted aromatic radicals specified for R and R1 are 2- or 4-chlorophenyl, 2 : 4-dichlorophenyl, 4-methoxyphenyl, and 4-nitro-phenyl and the radical <FORM:0892405/IV (b)/8> may be, for example <FORM:0892405/IV (b)/9> The radical R4 when heterocylic may be a furfuryl or tetrahydrofurfuryl radical.  Several examples are given for the production of a wide variety of compounds which fall within the scope of the first given formula.  The products have pesticidal properties (see Group VI).  Specification 875,583 is referred to.  Reference has been directed by the Comptroller to Specification 807,119.ALSO:A pesticidal composition comprises a compound of the formula <FORM:0892405/VI/1> in which R and R1 each represent an alkyl, alkenyl, cycloalkyl, aralkyl, aryl or heterocyclic radical which may be substituted or R and R1 together form part of a ring system, R2 is a branched or unbranched alkyl or alkylaryl radical interrupted by at least one oxygen or sulphur atom, preferably by at least two oxygen or sulphur atoms, R3 is a hydrogen or halogen atom or an alkyl radical, R4 is an aliphatic, alicyclic, aromatic, e.g. phenyl, chlorophenyl, or nitrophenyl, or heterocyclic radical, X and Y each represent -O-, -S-, -NH-, or -N-R, Z is an oxygen or sulphur atom, and n and m each represent 1 or 2 (see Group IV (b)) in admixture with a solid or liquid diluent.  The composition may be in the form of a solution or suspension prepared with water or a suitable organic solvent, e.g. an alcohol, petroleum, or tar distillate, or a spraying or dusting preparation containing an inert filler such as kaolin, gypsum or bentonite and which may also contain a wetting agent and an adhesive.  Other insecticides and/or fungicides may also be present.  The specified aliphatic radicals which R and R1 may represent may be substituted by chlorine, thiocyano, cyano or ester groups and substituted aromatic radicals specified for R and R1 are 2- or 4-chlorophenyl, 2 : 4-dichlorophenyl, 4-methoxyphenyl, and 4-nitrophenyl.  When R4 is a heterocyclic residue it may suitably be a furfuryl or tetrahydrofurfuryl radical.  Specified solvents which may be used to form spray concentrates are methanol, ethanol, isopropanol, butanol, acetone, methyl ethyl ketone, methyl cyclohexanol, benzene, toluene, xylene, kerosenes, petroleum fractions, and mixtures of such solvents.  Specification 875,583 is referred to.  Reference has been directed by the Comptroller to Specification 807,119.