Patent GB-888686-A (GB)
Title: Phosphorus-containing amino-triazole derivatives
IPC: C07F9/6518
Filed: 1958-04-24
Abstract: The invention comprises compounds which are <FORM:0888686/IV (b)/1> derivatives of an amino-triazol of the general formula <FORM:0888686/IV (b)/2> or of a tautomeric form thereof, in which derivatives the phosphorus atom is bound to one of the nitrogen atoms of the triazol ring, and in which R1, R2, R3 and R4 designate aliphatic hydrocarbon radicals, X is oxygen or sulphur, and R5 designates a hydrogen atom, an alkyl, cycloalkyl, aryl, or aralkyl group or such group containing one or more substituents, or is an aliphatically unsaturated hydrocarbon group or a carbalkoxy group. They may be obtained by reacting an amino-triazole of the above formula, or a tautomeric form thereof, or a salt thereof, with a compound of the general formula <FORM:0888686/IV (b)/3> or a salt thereof in which Hlg is a halogen atom, e.g. Cl or Br. Suitable salts of the amino-triazole are the hydrochloric acid and sulphuric acid salts and the bisulphate.  The reaction is preferably carried out in the presence of a hydrogen halide binding agent, e.g. a primary, secondary, or tertiary amine, a metal compound, e.g. a metal oxide, hydroxide, carbonate, bicarbonate, alcoholate, or carboxylate, or ammonia or an ammonium compound, e.g. ammonium carbonate or acetate. An excess of the aminotriazole may also be used as acid-binding agent.  A solvent may also be present and several suitable solvents are specified including hydrocarbons, aliphatic ethers and ketones, tertiary amines, acetonitrile, ethyl acetate, ethyl formate, nitrobenzene, carbon tetrachloride, and dimethylformamide. Examples are given for the production of compounds in which R1, R2, R3 and R4 are each methyl, X is oxygen and R5 is H, CH3, C2H5, (CH3)2CH, n-pentyl, heptyl, undecyl, phenyl, benzyl, styryl, p-chlorophenyl, p-methoxyphenyl, carbethoxy, carboisopropoxy, and carbo-n-pentoxy, respectively; R1, R2, R3 and R4 are each methyl, X is sulphur, and R5 is H or n-pentyl, and R1, R2, R3 and R4 ar each ethyl, X is oxygen and R5 is H or n-pentyl. Other R5 radicals mentioned are carboxyalkyl, isobutyl, and n-hexyl.  The products have pesticidal properties (see Group VI).  The amino-triazole starting materials may be obtained by reacting an amino-guanidine salt, e.g. the nitrate, bisulphate or sulphate with a carboxylic acid R5COOH or its acid halide and the preparation by this method of the aminotriazoles in which R5 is heptyl, undecyl, benzyl and styryl, respectively, is described.  The preparation of starting compounds in which R5 is a carbo-n-pentoxy and a carbo-isopropoxy group by treating the corresponding free carboxylic acid (R5=COOH) with n-pentanol and isopropanol, respectively, in the presence of dry HCl gas is also described.ALSO:A pesticidal composition comprises as active ingredient a compound which is a <FORM:0888686/VI/1> derivative of an amino-triazole of the general formula <FORM:0888686/VI/2> or of a tautomeric form thereof, in which derivative the phosphorus atom is bound to one of the nitrogen atoms of the triazol ring and in which R1, R2, R3 and R4 designate aliphatic hydrocarbon radicals, X is oxygen or sulphur, and R5 is a hydrogen atom, an alkyl, cycloalkyl, aryl or aralkyl group, or such group containing one or more substituents, or is an olefinically unsaturated hydrocarbon group or a carbalkoxy group (see Group IV (b)), said compound being dissolved or dispersed in or mixed with a liquid or solid carrier material, if desired with the addition of a surface-active substance, dispersion agent and/or adhesive.  The active ingredient is effective against various fungi and insects and the composition may be in the form of a water-miscible oil, wettable powder or dust powder.  Specified liquid diluents are xylene, toluene, dioxane, petroleum distillates rich in aromatic compounds, e.g. solvent naphtha, distilled tar oil, tetrahydronaphthalene, cyclohexane and mixtures of such liquids. Specified solid carriers include alumina, kaolin, talcum chalk, diatomaceous earth, infusorial earth, wood flour, tobacco dust and ground coconut shells.