A Facile Synthetic Approach to Imidazolidinone Biocides

Abstract

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.

Kinetics of N‐bromination of 2‐oxazolidinone

“…Although this work involved the single substrate 2-oxazolidinone, the reverse rate constants k i obtained in the studies of NBS and NBA give the rates of bromination of CH 3 …”

“…N -Halo-2-oxazolidinones [1,2] form polymers that can be used as coatings on plastics, glass and synthetic fibres [3], and the monomers can be used as disinfectants [4][5][6][7][8][9]. Although certain organisms are quite resistant to the most thoroughly studied chloro compound, 3-chloro-4,4-dimethyl-2-oxazolidinone [10] does have advantages as an auxiliary biocide, especially for disinfection of minor water supplies: it is an easily stored powder, and its relative stability ensures sustained action.…”

N‐Halamines

“…It has also been shown to have use potential for the aquaculture industry (187). Spirocycloalkyl derivatives of the N-chloroimidazolidinones, which may find application as disinfectants for nonpolar media, have also been reported (188). Melamines.…”

Preparation of antibacterial cellulose with s‐triazine‐based quaternarized N‐halamine

“…15 As one of the most effective biocides, N-halamine has been applied in many other fields, such as water purification, food packaging, latex paint, stainless steel, and air cleaning materials, due to its perfect antimicrobial efficacy, rechargeability, long-term stability, and nontoxicity. [16][17][18][19] Due to the existence of abundant hydroxyl groups, cotton fibers can be easily modified to bind with other compounds with antimicrobial properties. For example, N-halamines are usually able to attach to the surface of cotton fibers through chemical bonds or physical adsorption.…”

“…The oxidative halogens in N‐ halamines could be directly transferred to microbial cell membranes and inactivate microbes within a short period of time without releasing free halogen . As one of the most effective biocides, N‐ halamine has been applied in many other fields, such as water purification, food packaging, latex paint, stainless steel, and air cleaning materials, due to its perfect antimicrobial efficacy, rechargeability, long‐term stability, and nontoxicity …”