By the addition of substituted benzyl halides to hexamethylenetetramine, a series of quaternary salts of this base was obtained. These salts represent a new group of organic bactericides. The results obtained in the tests with these substances upon Bacillus typhosus have demonstrated the existence of direct relationships between chemical constitution and bactericidal action within the series.
The bactericidal character is directly attributable to the presence of the hexamethylenetetramine nucleus. The degree of the bactericidal action, however, is determined by the position, character, and number of the groups substituted in the benzene nucleus.
By the introduction of the methyl, chlorine, bromine, iodine, cyano, and nitro groups into the benzene nucleus of the parent benzyl hexamethylenetetraminium salt, the bactericidal power of this compound was notably enhanced. The substitution of these groups in the ortho position almost invariably resulted in substances which were more active than their meta or para isomers. The introduction of the methoxy group was without marked effect.
Several substances in which two hexamethylenetetraminium side-chains occurred were found to be the most active of the substances of this series when tested against Bacillus typhosus. Comparative tests with other bacterial types demonstrated that these compounds possessed a marked degree of specificity for Bacillus typhosus.