Patent GB-1019227-A (GB)
Title: Heterocyclic phosphate and thiophosphate derivatives
Inventor: MCHATTIE GORDON VICTOR
IPC: A01N57/16
Filed: 1963-03-28
Abstract: Insecticidal and fungicidal compositions comprise one or more pyrimidine derivatives of the formula:- <FORM:1019227/C4-C5/1> wherein R1, R2 and R5, which may be the same or different, represent alkyl or alkenyl radicals of not more than 6 carbon atoms, or R1 and R2 together with the adjacent N atom form a heterocyclic radical, R3 and R4 represent a hydrogen atom, alkyl or alkenyl radicals of not more than 6 carbon atoms and X represents O or S (see Division C2) in admixture with a diluent or carrier in the form of aerosols for use as sprays.  Specified propellants are CFCl3 and CF2Cl2.  An example is given where o, o-diethyl-o - (2 - dimethyl - amino - 4 - methylpyrimid-6-yl) phosphorothionate is mixed with CF2Cl2 in the presence of cyclohexanone at - 40 DEG  C. and the resulting solution put into suitable containers. The spray is suitable for use on domestic animals for treatment of parasitic infestations or for use as an insecticidal spray.ALSO:The invention comprises compounds of the formula <FORM:1019227/C2/1> wherein R1, R2 and R5, which may be the same or different, represent alkyl or alkenyl radicals of not more than 6 carbon atoms, or wherein R1 and R2 together with the adjacent nitrogen atom form a heterocyclic radical, R3 and R4 represent hydrogen, an alkyl or alkenyl radical of not more than 6 carbon atoms and X represents oxygen or sulphur. They may be obtained by reacting a compound of the formula <FORM:1019227/C2/2> wherein R1, R2, R3 and R4 have the same meanings as above, and R6 represents hydrogen or an alkali metal atom, with a halogeno derivative of the formula <FORM:1019227/C2/3> wherein R5 and X have the same meanings as above, and Y represents a halogen atom. Preferably alkali metal atoms for R6 are sodium and potassium and suitable halogen atoms for Y are chlorine and bromine.  When R6 represents hydrogen the reaction may be carried out in the presence of an acid-binding agent such as an alkali metal salt of a weak acid, or a tertiary organic base such as a trialkylamine of not more than 12 carbon atoms, or an N,N-dialkylarylamine. The reaction may be carried out in an inert diluent or solvent, e.g. benzene and may be accelerated by the application of heat.  The reaction may be carried out in the presence of a catalyst, e.g. mercurous chloride, mercuric chloride, mercurous iodide, mercuric iodide or cupric chloride.  Examples are given for the preparation of compounds where (1) R1 and R2 are methyl, R3 is methyl, R4 is hydrogen, R5 is ethyl, and X is sulphur; (2) R1, R2 and R3 are methyl, R4 is hydrogen, R5 is n-butyl and X is sulphur; (3) R1, R2 and R3 are methyl, R4 is hydrogen, R5 is ethyl and X is oxygen; (4) R1 and R2 are methyl, R3 is n-butyl, R4 is hydrogen, R5 is ethyl and X is sulphur; (5) R1 and R2 are n-butyl, R3 is methyl, R4 is hydrogen, R5 is ethyl and X is sulphur; (6) R1 and R2 are methyl, R3 and R4 are hydrogen, R5 is ethyl and X is sulphur; (7) R1, R2 and R3 are methyl, R4 is n-butyl, R5 is ethyl and X is sulphur; (8) R1 and R2 together with the adjacent nitrogen atom are piperidino, R3 is methyl, R4 is hydrogen, R5 is ethyl, and X is sulphur; and (9) R1, R2 and R3 are methyl, R4 is allyl, R5 is methyl and X is sulphur.  The compounds are useful as insecticides and fungicides (see Division A5).  5 - n - Butyl - 2 - dimethylamino - 4 - hydroxy-6-methyl of pyrimidine used as a starting material may be prepared by adding a sodium hydroxide solution to a stirred suspension of dimethyl guanidine sulphate in ethyl a -n-butyl-acetoacetate and ethanol and refluxing the mixture for 8 hours.  Pharmaceutical compositions comprise compounds of the above general formula in admixture with a solid diluent or carrier which may be used internally in the form of tablets, capsules, boluses, suspensions, emulsions or solutions, and they may also contain conventional excipients, lubricating agents, and granulating and disintegrating agents.  Alternatively the veterinary compositions may be administered parenterally in the form of sterile solutions, suspensions or emulsions and may contain conventional excipients. The veterinary compositions may also contain additionally one or more substances of known veterinary utility for example anthelmintics and/or bactericides. The veterinary compositions may additionally be stabilized by the incorporation of stabilizing agents.  Examples are given which show the preparation and uses of these compositions.ALSO:Insecticidal and fungicidal compositions suitable for the eradication of undesired insect or fungal infestations in growing plants or crops, or of insect infestations in domestic animals comprise one or more pyrimidine derivatives of the formula: <FORM:1019227/A5-A6/1> where R1, R2 and R5, which may be the same or different, represent alkyl or alkenyl radicals of not more than 6 carbon atoms, or R1 and R2 together with the adjacent nitrogen atom form a heterocyclic radical, R3 and R4 represent a hydrogen atom, alkyl or alkenyl radicals of not more than 6 carbon atoms and X represents sulphur or oxygen (see Division C2), in admixture with a solid diluent or carrier.  The usual solid diluents or carriers may be employed.  The compositions may also be in the form of liquid preparations to be used as dips or sprays which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more wetting agents, dispersing agents, emulsifying agents or suspending agents.  The compositions to be used as sprays may also be in the form of aerosols.  The composition may be stored in the form of a concentrate containing a high proportion (e.g. 10-85% by weight) of the active ingredient or ingredients and the concentrate diluted with water before use.  For agricultural or horticultural purposes an aqueous solution containing between 0.001% and 0.1% by weight of the active ingredient or ingredients may be used.  The compositions may be used for veterinary purposes and in this case they may be in the form of dips, sprays or dusting powders, or a hand dressing prepared from an ointment or cream base when applied externally.