Substitued 5-nitro-1, 3-dioxanes: correlation of chemical structure and antimicrobial activity

Various derivatives of 5-nitro-1, 3-dioxane were synthesized to determine the relative effect of chemical substitution in the 2-and 5-positions on broad spectrum antimicrobial activity. Each compound was evaluated quantitatively by calculation of a microbiocidal index, which measured the time to kill several different microorganisms. This test system indicated that 5-bromo-5-nitro substitution was essential for significant activity. Optimal activity was effected by 2-methyl substitution in the alkyl series and 2-hydroxy-phenyl substitution in the aryl series. The antimicrobial activity of the substituted dioxanes was not related directly to water solubility or hydrolysis to microbiocidal diols or aldehydes.