Patent GB-841634-A (GB)
Title: Triphenylmethane derivatives and their use in molluscicidal compositions
Inventor: DAVEY DAVID GARNET
IPC: C09B11/04
Filed: 1957-04-17
Abstract: The invention comprises secondary amines of the formula R3C.NHR11 wherein R stands for a phenyl radical, optionally substituted by a methyl radical or a chlorine atom, and R11 stands for an alkyl radical, provided that when R11 stands for a methyl, ethyl, n-propyl, tertbutyl or iso-amyl radical, the phenyl radical is substituted as specified above.  The invention also comprises the process of preparing the amines by reacting the corresponding triphenylmethyl halide with the requisite alkylamine.  The invention further comprises the hydrochlorides, sulphates, nitrates, and isethionates of the amines.  The amines and their salts are active components for molluscicidal compositions (see Group VI).  In Example 24, a solution of triphenylmethyl chloride is added to a vigorously-stirred solution of isobutylamine in benzene.  After heating under reflux for 4 hours, the mixture is cooled and filtered.  The filtrate is washed with water, dried over magnesium sulphate, and then evaporated to dryness. The residual syrup is crystallized from methanol to give isobutyl triphenylmethyl amine.  Examples 34 and 35 describe the preparation of n-propyl tri-(p-tolyl) methyl amine and of n-propyl tri-(p-chlorophenyl) methyl amine, respectively.  In Example 36, the hydrochloride of isopropyl triphenylmethyl amine is prepared by dissolving the base in ether, and adding an excess of ethereal hydrogen chloride. The solid so obtained is crystallized from a mixture of methanol and ether.  Examples 37 and 38 describe the preparation of sec.-butyl triphenylmethyl amine and of n-butyl triphenylmethyl amine, and their hydrochlorides.ALSO:The invention comprises molluscicidal compositions wherein the active ingredient is a triphenylmethane derivative of the formula R3CR1 in which R stands for a phenyl radical, optionally substituted with a halogen atom or an alkyl radical, and R1 stands for an alkoxy or alkylamino radical, or for a phenylamino radical optionally substituted with a halogen atom, in admixture with an inert, non-toxic carrier or diluent.  In those cases where the triphenylmethane derivatives are basic, the hydrochlorides, nitrates, sulphates, isethionates, 2-methyl-4-chloro- and 2,4-dichloro-phenoxyacetates, gamma-2-methyl-4-chloro- and gamma-2,4-dichloro-phenoxybutyrates may be used in the compositions. Examples of specified active ingredients are:- n-propyl triphenylmethyl amine and its hydrochloride, nitrate and isethionate, p-chlorophenyl triphenylmethyl amine, n-propyl tri-(p-tolyl)-methylamine, and ethyl triphenylmethyl ether.  The compositions may comprise p  solutions of the active ingredient in acetone, polyethylene glycol trichlorethylene, chloroform and other organic solvents.  Such solutions are admixed with water before use. The salts may be directly dissolved in water.  Preferred compositions for use on ponds are those wherein the active ingredient is dissolved in toluene or kerosene in the presence of a wetting-agent such as a condensation product of octylcresol with 8 to 10 molecular proportions of ethylene oxide.  Dispersible powders containing the active ingredient in the form of a salt in the presence of a wetting agent and a dispensing-agent, such as polyglyceride ricinoleate are particularly useful in slow-moving rivers, and near pumping stations on canals.  Tablets may be prepared by compressing a mixture of the active ingredient a wetting-agent, starch and magnesium stearate, or urea.  Compositions for application to the aqueous habitat of molluscs may be include absorbent materials such as bricks, tiles, paper and cloth. Copper sulphate, benzene hexachloride, ahd dichloro-diphenyltrichloro-ethane may also be included in the compositions.