Patent GB-990327-A (GB)
Title: Substituted vinyl phosphorothiates and phosphonothioates and pesticidal compositions containing them
IPC: C07F9/173
Filed: 1964-01-23
Abstract: The invention comprises compounds having the general formula <FORM:0990327/C2/1> wherein " alkyl " represents an alkyl group containing 1 to 4 carbon atoms, n is 0 or 1, p is 2 or 3, x is bromine or chlorine, and X1 is hydrogen, bromine or chlorine.  They are prepared by reacting an alpha-polyhaloacetophenone of the formula <FORM:0990327/C2/2> wherein X, X1 and p are the same as above, with a phosphoro- or phosphono halidothionate having the formula <FORM:0990327/C2/3> wherein " alkyl " and n have the same meanings as above and hal represents a halogen atom, in the presence of a base. The reaction may be carried out by mixing approximately equimolar amounts of the reactants and base together, in a suitable solvent at a temperature above 0 DEG  C. preferably between room temperature and 35 DEG  C.  Suitable solvents are ether and benzene.  A suitable base is sodium hydride.  The product may be isolated by filtering the reaction mixture or by distilling off the solvent and crystallizing the residue from a suitable solvent such as pentane.  Examples are given for the preparation of compounds where " alkyl " represents methyl and/or ethyl groups, n is 0 or 1, p is 2 or 3, X is bromine and chlorine and X1 is hydrogen, bromine or chlorine.  The products are useful for controlling insects.  The alpha-polyhaloacetophenones used as starting materials may be prepared by halogenating the appropriate acetophenones. Alternatively, they may be prepared by a Friedel-Crafts ketone synthesis in which aluminium chloride is mixed with the appropriate polyhalobenzene, then the resulting mixture is mixed with the appropriate polyhaloacetyl chloride and then heated to 80-100 DEG  C. until the reaction is complete.  Then the mixture is cooled and treated with an ice-hydrochloric acid mixture to decompose the complex formed and separate out the water-soluble aluminium salts.  The product may be isolated by extraction with a suitable solvent e.g. ether, stripping the solvent from the extract, and distilling the residue.ALSO:A pesticidal composition comprises as active ingredient a compound of the general formula <FORM:0990327/A5-A6/1> wherein "alkyl" represents a C1-C4 alkyl group, n is 0 or 1, p is 2 or 3, X is bromine or chlorine and X1 is hydrogen, bromine or chlorine (see Division C2) together with a carrier or a surface-active agent or both.  The term "carrier" means a material which may be inorganic or organic and synthetic or of natural origin with which the active substance is mixed. The carrier may be a solid, a liquid or a compressed gas.  The compositions may contain surface-active agents which act as spreading, wetting, dispersing and/or emulsifying agents.  The compositions may be formulated as granules prepared e.g. by impregnating and/or coating granules of a solid carrier with a compound of the above formula or by forming granules of mixtures of the compound and a carrier.  The compositions may also be formlated as dusts, as wettable powders or as emulsifiable concentrates.  The compositions may contain other ingredients such as other pesticides, hormones, stickers and/or fertilizers.  The compositions may be applied for insecticidal purposes to the surfaces of plants, buildings, soil, materials such as paper, sand, bricks, concrete or plaster; they may be disseminated into soil; they may be incorporated into surface coatings such as waxes, resins, paints, lacquers or varnishes; or in plastic materials such as plastic sheetings to give packaging and wrapping materials which are resistant to insect attack.