A facile synthetic approach to imidazolidinone biocides

A synthetic route has been developed for the production of novel N-halamine disinfectants. These compounds are derivatives of 1,3-dichloro-2,2,5,5-tetramethylimidazolidin-4-one (DC) The synthetic route chosen consists of producing a 2,2,5,5-tetrasubstituted-imidazolidin-4-thione with identical substituents at the 2- and 5-positions, followed by hydrolysis of the cyclic thione to the corresponding acyclic aminothioamide, condensation with a ketone resulting in the formation of a 2,2,5,5-tetrasubstituted-imidazolidin-4-thione having different substituents at the 2- and 5-positions, oxidation to the corresponding 2,2,5,5-tetrasubstituted-imidazolidin-4-one, and finally, chlorination to the desired N-halamine derivative. These derivatives are more nonpolar than is DC, and thereby may possess more antimicrobial activity against microorganisms containing cell membranes of considerable lipophilicity than does DC. Preliminary results presented in this work show that these new derivatives are bactericidal, with some more so than is DC against Staphylococcus aureus. Potential applications may exist for these compounds in the disinfection of nonpolar media such as oils, paints, and lubricants as well as for aqueous solutions of organisms containing lipophilic cell membranes.