Patent GB-745064-A (GB)
Title: Fungicidal and bactericidal compositions
Inventor: BIRTWELL STANLEY
IPC: D06P3/52
Filed: 1953-03-26
Abstract: In the preparation of bis-biguanides of the formula <FORM:0745064/IV(a)/1> wherein A and B stand for the same or different aromatic nuclei optionally substituted by one or more halogen, nitro, alkyl or alkoxy radicals, and X stands for a hydrocarbon or a dialkoxybenzene radical of not more than 15 carbon atoms, by reacting a diamine of the formula NH2-X-NH2 with a dicyandiamide of the formula A-NH-C( : NH)-NH-CN or <FORM:0745064/IV(a)/2> with an amine of the formula ANH2 wherein A and X have the meanings stated above, in the form of a salt thereof, the process is carried out in the presence of a non-ionic substance possessing wetting and/or detergent properties as the reaction solvent.  In examples reaction is effected between p-chlorophenyldicyandiamide and hexamethylenediamine dihydrochloride in the presence of the condensation product of octyl or cetyl cresol or stearic acid and ethylene oxide; 4:41-diaminodiphenylmethane dihydrochloride and phenyl dicyandiamide in the presence of the condensation products of octyl cresol with ethylene oxide; phenyldicyandiamide and hexamethylenediamine dihydrochloride in the presence of the condensation product of octyl cresol and ethylene oxide; p-chloroaniline hydrochloride and hexamethylene-bis - dicyandiamide in the presence of the condensation product of octylcresol and ethyleneoxide.  Other starting materials are trimethylenediamine, tetramethylenediamine, pentamethylenediamine, heptamethylenediamine, decamethylenediamine, 1:4 - bis - g -aminopropyloxybenzene, 4:41 - diaminodiphenylmethane and p - phenylenediamine, phenyldicyandiamide, p - tolyldicyandiamide, 2:4 - dimethylphenyldicyandiamide, p - anisyldicyandiamide, o - chlorophenyldicyandiamide, m - chlorophenyldicyandiamide, 2:5 - dichlorophenyldicyandiamide, 3:4 - dichlorophenyldicyandiamide, m - nitrophenyldicyandiamide, a  - naphthyldicyandiamide and b  - naphthyldicyandiamide, aniline, p - toluidine, 2:4 - dimethylaniline, p - anisidine, o - chloroaniline, m - chloraniline, p - chloroaniline, 2:5 - dichloroaniline, 3:4 - dichloroaniline, m - nitroaniline, a  - naphthylamine and b  - naphthylamine; compounds of the formula CN-NH-C(=NH)-NH-X-NH-C(=NH)-NH-CN may for example be those wherein X stands for <FORM:0745064/IV(a)/3> Specifications 705,838 and 710,105, [Group III], are referre to.ALSO:In the preparation of detergent compositions comprising bis-biguanides of the formula <FORM:0745064/III/1> wherein A and B stand for the same or different aromatic nuclei optionally substituted by one or more halogen, nitro, alkyl or alkoxy radicals, and X stands for a hydrocarbon or a dialkoxy-benzene radical of not more than 15 carbon atoms, by reacting a diamine of the formula NH2-X-NH2 in the form of a salt thereof with a dicyandiamide of the formula A-NH-C(:NH)-NH-CN, or reacting a dicyandiamide of the formula <FORM:0745064/III/2> with an amine of the formula ANH2 in the form of a salt thereof, the action in both cases is conducted in the presence of a non-ionic substance possessing wetting and/or detergent properties.  Specified non-ionic substances are condensation products of ethylene oxide with alkylphenols, fatty alcohols, and fatty acids or their amides, e.g. containing at least 7 carbon atoms e.g. octyl or cetyl cresol or stearic acid.  Specifications 705,838 [Group IV(b)] and 710,105, are referred to.ALSO:In the preparation of a fungicidal and bactericidal composition comprising bisbiguanides of the formula <FORM:0745064/VI/1> wherein A and B stand for the same or different aromatic nuclei optionally substituted by one or more halogen, nitro, alkyl or alkoxy radicals, and X stands for a hydrocarbon or a dialkoxybenzene radical of not more than 15 carbon atoms, by reacting a diamine of the formula NH2-X-NH2 in the form of a salt thereof with a dicyandiamide of the formula A-NH-C (:NH)-NH-CN or by reacting a dicyandiamide of the formula <FORM:0745064/VI/2> with an amine of the formula ANH2 in the form of a salt thereof, the reaction in both cases is conducted in the presence of a non-ionic substance possessing wetting and/or detergent properties.  Specified dicyandiamides of the formula NH2-X-NH2 are hexamethylene diamine, trimethylenediamine, tetramethylenediamine, pentamethylenediamine, heptamethylenediamine, decamethylenediamine, 1 : 4-bis-g -aminopropyloxybenzene, 4 : 41-diaminodiphenylmethane and p-phenylenediamine; specified dicyandiamides of the formula A-NH-C (:NH)-NH-CN are p-chloro-phenyldicyandiamide, phenyldi-cyandiamide, p-tolyldicyandiamide, 2 : 4-dimethylphenyldicyandiamide, p-anisyldicyandiamide, o-chlorophenyldicyandiamide, m-chlorophenyldicyandiamide, 2 : 5-dichlorophenyldicyandiamide, 3 : 4-dichlorophenyldicyandiamide, m-nitrophenyldicyandiamide, p  a -naphthyldicyandiamide and b -naphthyldicyandiamide; and specified compounds of the formula CN-NH-C(=NH)-NH-X-NH-C (=NH)-NH-CN are those in which X stands for -[CH2]3-, -[CH2]4,- -[CH2]5-, -[CH2]6-, -[CH2]7-, -[CH2]10-, -[CH2]3OC6H4O[CH2]3-, -C6H4-NH-C6H4- and -C6H4-; are specified amines of the formula ANH2 are aniline, p-toluidine, 2:4-dimethylaniline, p-anisidine, o-chloroaniline, m-chloroaniline, p-chloroaniline, 2:5-dichloroaniline, 3:4-dichloroaniline, m-nitroaniline, a -naphthylamine and b -naphthylamine. Specifications 705,838, [Group IV(b)], and 710,105 are referred to.