GB869181A - Improvements relating to heterocyclic nitrogen compounds and their use - Google Patents

Abstract

The invention comprises compounds of the formula: <FORM:0869181/IV (b)/1> where A is a saturated hydrocarbon radical bound at the two nitrogen atoms by a ,b - or a ,g ..-carbon atoms, R1 is a possibly substituted benzyl radical, and R2 is hydrogen, or an aliphatic, araliphatic or cyclohexyl radical; either R1 or R2 containing, or R2 being, a lipophilic aliphatic radical. The group A may be aliphatic or cycloaliphatic. These compounds may be prepared by reacting a diamine of formula R1-NH-A-NH-R2 with a cyanogen halide, advantageously in an inert organic solvent and heating if necessary, and liberating the base with alkali. Lists of suitable diamines are given, including compounds in which the benzyl radical is substituted by chloro, hydroxy, alkyl and methoxy groups. In a modification, a cyanogen halide is reacted with a diamine of formula NH2-A-NH-R, where R is one of R1 and R2, and introducing the other N-substituent into the product by alkylation or aralkylation. In a second modification where R1 is benzyl substituted by lipophilic groups and R2 is hydrogen, a diamine NH2-A-NH2 is reacted with a cyanogen halide and the product is reacted with about the stoichiometrical amount of a suitable aralkylating agent. The compounds of the invention form salts with inorganic and organic acids. The starting diamines may be prepared by (i) esterifying a,b - or a,g aminoalcohols with e.g. HCl or H2SO4, alkylating or benzylating at the nitrogen, and treating with ammonia or an amine; (ii) reacting di-primary a,b - or a-g ..- diamino-alkanes or cycloalkanes, in which one amino group may be protected by acylation, with reactive alkyl, cyclohexyl or benzyl compounds; (iii) reducing the Schiff's bases obtained from diamines and an aldehyde. The compounds of the invention have biocidal activity (see Group VI). Reference has been directed by the Comptroller to Specification 765,547.ALSO:Biocidal compositions contain as active ingredient a compound of formula <FORM:0869181/VI/1> where A is a saturated hydrocarbon radical bound at the two nitrogen atoms by a , b - or a ,g -carbon atoms, R1 is a possibly substituted benzyl radical, and R2 is hydrogen or an aliphatic, araliphatic or cyclohexyl radical; either R1 or R2 containing, or R2 being, a lipophilic aliphatic radical. The group A may be aliphatic or cycloaliphatic. Specified substituents on R1 include halogen, alkyl, hydroxy and methoxy. The compositions may be powders, dispersions or solutions, and may contain inert carriers or fillers, capillary active agents, cleansing agents, cosmetics, medicinal preparations or other biocidal agents. The compositions may be based on organic solvents, or aqueous solutions of the salts of the above compounds may be used. The compounds have bactericidal or bacteriostatic, fungicidal and algaecidal activity. Reference has been directed by the Comptroller to Specification 765,547.