Patent GB-940033-A (GB)
Title: New unsaturated phosphorus-containing esters and their manufacture and pesticidal preparations containing them
IPC: C07F9/113
Filed: 1960-10-06
Abstract: The invention comprises organo-phosphorus compounds of the general formula:- <FORM:0940033/C2/1> in which R and R1 each represents an alkyl, alkenyl, cycloalkyl, aralkyl, aryl, or heterocyclic residue which may be substituted or R and R1 together form part of a ring system, R2 is the residue of a heterocyclic alcohol containing at least one oxygen atom as a ring hetero-atom, R3 is a hydrogen atom, an alkyl radical or a halogen atom, R4 is an aliphatic residue especially C1-C4 alkyl, X and Y each represents an -O-, -S-, -NH- or -N(R)- bridge wherein R is as defined above, Z is an oxygen or sulphur atom, and n and m each represents 1 or 2. R2 is suitably a tetrahydrofurfuryl residue, the residue of a cyclic acetalised glycerine or the residue of a cyclic derivative of pentaerythritol. They may be obtained by reacting a compound of the formula:- <FORM:0940033/C2/2> in which R5 is a C1-C4 alkyl group or a chlorethyl group and the other symbols are as defined above with a compound of the formula:- <FORM:0940033/C2/3> in which Hal is a halogen atom, e.g. Cl or Br, and the other radicals are as defined above, or by reacting a compound of the formula:- <FORM:0940033/C2/4> in which Me is an alkali metal, e.g. Na, with a compound of the formula:- <FORM:0940033/C2/5> in which R2, R3, R4 and Hal are as defined above.  Compounds in which R3 is a hydrogen atom or an alkyl radical can also be made by the following condensation:- <FORM:0940033/C2/6> wherein the symbols are as defined above.  The reactions are suitably effected at from 50 DEG  to 200 DEG C and an inert solvent may be present.  If desired the reactions may be carried out in an inert gaseous atmosphere, e.g. under nitrogen, and/or under reduced pressure. When the radicals R and R1 are substituted groups they may be for example, 2-chlorethyl groups, aliphatic groups containing thiocyano, cyano, or ester groups, 4-methoxy phenyl, 4-nitrophenyl, 2- or 4-chlorophenyl or 2, 4-dichlorophenyl groups.  The heterocyclic alcohol from which R2 is derived may be tetrahydrofurfuryl alcohol or a cyclic alcohol obtained by acetal formation of a trihydric or higher polyhydric alcohol, e.g. glycerol or penta-erythritol with an aldehyde, e.g. formaldehyde, acetaldehyde, benzaldehyde, or crotonaldehyde or with a ketone such as acetone, methyl isobutyl ketone, or acetophenone. Several examples are given and the products have pesticidal properties (see Division A5).  Reference has been directed by the Comptroller to Specification 807,119.ALSO:A pesticidal composition comprises a solid, liquid or gaseous carrier and a compound of the formula <FORM:0940033/A5-A6/1> in which R and R1 each represents an alkyl, alkenyl, cycloalkyl, aralkyl, aryl or heterocyclic residue which may be substituted, or R and R1 together form part of a ring system, R2 is the residue of a heterocyclic alcohol containing at least one oxygen atom as a ring hetero-atom, e.g. a tetrahydrofurfuryl group or the residue of a cyclic acetalised glycerine, R3 is a hydrogen atom, an alkyl residue or a halogen atom, R4 is an aliphatic residue especially C1-C4 alkyl, X and Y each represent an -O-, -S-, -NH-, or -N(R)- bridge wherein R is as defined above, Z is an O or S atom, and n and m each represents 1 or 2 (see Division C2). The composition may be in the form of a fumigating preparation or of a dusting or spraying preparation, e.g. as a solution or suspension in an organic solvent e.g. alcohol, petroleum, or a tar distillate.  Specified inert fillers are kaolin, gypsum and bentonite, and sulphated cellulose waste liquor, cellulose derivatives and the usual wetting or emulsifying agents or adhesive agents may be present.  Other insecticides and/or fungicides may also be present.  The Specification refers to treatment of air, living rooms, cellars &c., living substrates, pelts, feathers, wool, plants and other vegetable organisms.  Reference has been directed by the Comptroller to Specification 807,119.