Patent GB-932388-A (GB)
Title: New thiophosphoric acid esters and pesticidal compositions containing them
Inventor: SHERLOCK EDWARD
IPC: C07F9/6524
Filed: 1959-04-23
Abstract: The invention comprises compounds of the formula:-<FORM:0932388/IV(a)/1> in which R1 and R11 are C1-C4 alkyl radicals, X is an atom of oxygen or sulphur, and Z together with the adjacent N atom and the adjacent carbon atom constitute a substituted or unsubstituted 5- or 6-membered aromatic heterocyclic ring, said ring containing at least one atom of nitrogen, oxygen, or sulphur in addition to the nitrogen atom depicted, and salts of said compounds. Specified heterocyclic rings are imidazole, pyrazole, triazole, tetrazole, pyrazine, pyridazine, pyrimidine, a triazine, thiazole, thiadiazole, oxazole, and isoxazole.  The heterocyclic ring may contain one or more substituents, e.g. alkyl, cycloalkyl, aryl, nitroaryl, or aralkyl radicals, or amino, hydroxy, or carboxylic ester groups and the substituents can be carried by either carbon or nitrogen atoms in the ring.  The preferred salts of the products are acid addition salts, e.g. oxalates or hydrochlorides.  The compounds may be obtained by reacting a compound of the formula <FORM:0932388/IV(a)/2> with a compound of the formula (R1O)(R11O)P(X)SM wherein Y is Cl, Br or I and M is an alkali metal, e.g. Na, or K, or an ammonium radical.  The process is conveniently effected by using a solution or dispersion of the reactants in a suitable inert organic solvent e.g. methanol, ethanol, acetone or dioxane. Reaction temperatures may vary from room temperature to e.g. 100 DEG C. and it is convenient to reflux a solution of the reactants in the organic solvent.  Several examples are given and the products have pesticidal properties (see Group VI).  The Provisional Specification includes examples for the production of the compounds:- <FORM:0932388/IV(a)/3> Specification 899,701 is referred to.ALSO:A pesticidal composition comprises a suitable diluent or carrier and as active ingredient a compound of the formula <FORM:0932388/VI/1> in which R1 and R11 are C1-C4 alkyl radicals, X is an atom of oxygen or sulphur and Z together with the adjacent N atom and the adjacent C atom constitute a substituted or unsubstituted 5- or 6-membered aromatic heterocyclic ring, said ring containing at least one atom of nitrogen, oxygen or sulphur in addition to the N atom depicted, or a salt of such compound, especially an acid addition salt e.g. an oxalate or hydrochloride (see Group IV (b)).  Specified heterocyclic rings are imidazole, pyrazole, triazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, thiazole, thiadiazole oxazole and isoxazole.  The heterocyclic ring may contain one or more substituents e.g. alkyl, cycloalkyl, aryl, nitroaryl, amino, hydroxy or carboxylic ester groups and the substituents can be carried by either carbon or nitrogen atoms in the ring.  The composition may be in the form of a liquid or powder and may contain a wetting or dispersing agent.  Specified diluents or carriers are water, methanol, tetrahydrofurfuryl alcohol, diacetone alcohol, b -ethoxy ethanol, fuller's earth, talc, kaolin, kieselguhr and bentonite. Specification 899,701 is referred to.