Patent GB-716020-A (GB)
Title: Improvements in the production of fungicidal cyclohexadienone derivatives
IPC: A01N35/06
Filed: 1952-12-19
Abstract: A process for the production of fungicidal derivatives of cyclohexadienone consists in reacting hexachlorocyclohexadiene-(1 : 4)-one-(3) with compounds containing primary or secondary amino groups.  The products are probably of the formula <FORM:0716020/IV (b)/1> wherein R and R1 represent equal or different alkyl, aralkyl, aryl or cycloalkyl groups which may contain substituents such as amino, hydroxyl, ether, aldehyde, keto, acetal, carboxyl, ester or nitrile groups or halogen atoms or may be members of a common ring, and R may also represent a hydrogen atom.  Specified compounds with primary or secondary amino groups are methylamine, ethylamine, propylamines, hexylamines, dimethylamine, diethylamine, methylhexylamine, ethylene diamine, hexylene diamine, cyclohexylamine, dicyclohexylamine, methyl-hexadecylamine, bis dodecylamine, pyrrolidine, piperidine, morpholine, benzylamine, aniline, and N-methylaniline and their homologues and halogen or nitro-derivatives, allylamine, diallylamine, methallylcyclohexylamine, the mixture of chlorallylamines obtainable by the reaction of trichloropropane with ammonia, hydroxyamines, e.g. ethanolamine, diaminodipropyl ether, aminoketones such as p-aminoacetophenone or aminonitriles, e.g. e -aminocapronitrile.  Di- and polyamino compounds may react with one or more molecules of the hexachlorocyclohexadiene-(1.4)-one (3).  The hexachlorocyclohexadieneone-(1.4)-one-(3) may be obtained by chlorination in the presence of catalysts such as iron chloride or antimony pentachloride of phenol or chlorophenols, especially the chlorophenol mixture obtained from hexachlorocyclohexanes by splitting off hydrogen chloride and reaction with alkali or alkaline earth metal hydroxide or alcoholates.  Examples describe the reaction of hexachlorocyclohexadienene - (1.4) - one-(3) with (1) N-methallylcyclohexylamine; (2) piperidine, benzylamine, dimethylamine, pyrrolidine and ethylene diamine respectively; (3) about one-half and one molecular proportion respectively of ethylene diamine respectively.  As fungicides the products can be used as solutions, emulsions or powders, if desired in admixture with powders such as talc or kieselguhr.ALSO:A process for the production of fungicidal derivatives of cyclohexadienone consists in reacting hexachlorocyclohexadine- (1.4)-one-(3) with compounds containing primary or secondary amino groups.  The products are probably of the formula <FORM:0716020/VI/1> wherein R and R1 represent equal or different alkyl, aralkyl, aryl or cycloalkyl groups which may contain substituents such as amino, hydroxyl, ether, aldehyde, keto, acetal, carboxyl, ester or nitrile groups or halogen atoms or may be members of a common ring and R may also represent a hydrogen atom.  The products may be used as solutions in organic solvents, in aqueous suspensions or emulsions or in powder or dust form, if desired in admixture with powders such as talc or kieselguhr.  Specified compounds with primary or secondary amino groups for the above reaction are methylamine, ethylamine, propylamines, hexaylamines, dimethylamine, dietheylamine, methylhexylamine, ethylene diamine, hexylene diamine, cyclohexylamine, dicyclohexylamine, methyl-hexadecylamine, bis-dodecylamine, pyrrolidine, piperidine, morpholine, benzylamine, aniline and N-methylaniline and their homologues and halogen or nitro-derivatives, allylamino, diallylamine, methallylcyclohexylamine, the mixture of chlorallyamines obtainable by the reaction trichloropropane with ammonia, hydroxyamines, e.g. ethanolamine, diaminodipropyl ether, aminoketones such as p-aminoacetophenone or aminontriles, e.g. E-aminocapronitrile.  Di-and polyamino compounds may react with one ore more molecules of the hexachlorocyclohexadiene-(1.4)-one-(3). Examples of the preparation are given (see Group IV(b)).