Synthesis of Bis-Quaternary Salts of Ammonia from Aromatic Compounds through the Formation of Glycidyl Ether and their Plant Growth Retardant Potential

Trialkylamines, 1-N,N-diethylamino-3-(2’-methylphenoxy)propan-2-ol (5a); 1-N,N-diethyl amino-3-(3’-methylphenoxy)propan-2-ol (5b); 1-N,N-diethylamino-3-(4’-methylphenoxy) propan-2-ol (5c) and 1-N,N-diethylamino-3-(2’-hydroxymethylphenoxy) propan-2-ol (5d); were prepared from respective phenols and (3-N,N-diethylamino-2-hydroxypropyl)2’-aryloxyethanoate (9a-d), were prepared from phenoxyethanoic acid (6a), 2-methylphenoxyethanoic acid (6b), 3-methyiphenoxyethanoic acid (6c) and 4-methylphenoxyethanoic acid (6d) through the reaction of epichlorohydrin (2,3-epoxypropylchloride) followed by reaction with diethylamine. The tertiary amines (5a-d) were then converted into bis-quaternary salts by reacting with 1,6-hexanodioyl chloride and 9a-d with 1,2-dichloroethane separately. These salts were found to inhibit seedling growth and adventitious root formation on hypocotyls cuttings of vigina radiata (SML-668) significantly.