Patent GB-963986-A (GB)
Title: Succinimidomethyl-substituted quaternary ammonium compounds
IPC: C07D207/404
Filed: 1960-08-26
Abstract: The invention comprises compounds of the general formula: <FORM:0963986/C1/1> in which An represents an anion; R and Rx represent hydrogen or alkyl or alkenyl groups; R1 represents a lipophilic group of 10-25 carbon atoms and R2 and R3 each represent a methyl, ethyl, b -hydroxyethyl or benzyl group; or alternatively at least one of the groups R and Rx represents a lipophilic group of 8-25 carbon atoms the other being hydrogen, alkyl or alkenyl and R1, R2 and R3 each represents a methyl, ethyl, b -hydroxyethyl or benzyl group with the proviso that R1 can also represent a lipophilic group of 10-25 carbon atoms and that R2 and R3 may be joined together to form a heterocyclic group containing 5-6 cyclic atoms which may be substituted by one or more C1-C4 alkyl groups. They may be prepared by reacting an N-halomethyl succinimide of formula: <FORM:0963986/C1/2> with a tertiary amine of formula NR1R2R3 where An is chlorine or bromine.  A "lipophilic" substituent is defined as one which imparts to the quaternary ammonia compound a solubility in xylene of at least 5% at 25-30 DEG C.  The preferred lipophilic groups are alkyl or alkenyl groups containing 8-12 carbon atoms. Suitable tertiary amines which may be used as starting materials are:n-dodecyldimethylamine, cetyldimethylamine, decyldiethylamine, dodecylbenzylmethylamine, dodecyldibenzylamine, N-dodecylmorpholine, N-octadecylmorpholine, N-dodecylbenzylmorpholine, N-nonylmethylbenzylmorpholine, N-myristylpyrrolidine, N - cetylpiperide, oleyldimethylamine, (5, 5, 7, 7-tetramethyl-2-octenyl) dimethylamine, octyloxypentenyldimethylamine, (octylbenzyl)dimethylamine, dodecylbenzyldimethylamine, octylphenoxyethoxyethyldimethylamine, nonylphenoxyethoxyethylbenzylmethylamine, nonylphenoxyethyldi(hydroxyethyl)amine, octylphenoxyethoxyethylmorpholine, nonylphenoxyethoxyethylpiperidine and (diethylphenyl-2-pentenyl)-dimethylamine. Suitable halomethyl succinimides are the N-chloromethyl and N-bromomethyl derivatives of succinimides of a -methyl-, a a 1-dimethyl-, a -butenyl-, a -butyl-, a -dodecenyl- or a -dodecyl-succinimide.  The chloride and bromide ions in the quaternary compounds may be replaced in known manner by other anions. e.g. phosphate, acetate or propionate. (N-Chloromethyl)dodecenylsuccinimide used as starting material may be prepared by reacting dodecenylsuccinimide and formaldehyde to give (N-hydroxymethyl)dodecenyl succinimide and reacting this with thionyl chloride.ALSO:New compounds of the general formula <FORM:0963986/A5-A6/1> in which An represents an anion, R and Rx represent hydrogen or alkyl or alkenyl groups, R1 represents a lipophilic group of 10-25 carbon atoms and R2 and R3 each represent a methyl, ethyl, b -hydroxy ethyl or benzyl groups; or alternatively at least one of the groups R and Rx represents a lipophilic group of 8-25 carbon atoms, the other being hydrogen, alkyl or alkenyl and R1, R2 and R3 each represents a methyl, ethyl, b -hydroxyethyl or benzyl group or R1 may also be a lipophilic group of 10-25 carbon atoms and R2 and R3 joined together to form a heterocyclic ring, may be used, for example at 1% concentration, to treat plants against diseases and fungi.