Bactericidal activities of selected organic N-halamines

Abstract

The bactericidal efficacies of three organic N,N'-dihalamine disinfectants in the class of compounds termed imidazolidinones were determined for combinations of pH, temperature, and water quality treatments by using Staphylococcus aureus and Shigella boydii as test organisms. The compound 1,3-dibromo-4,4,5,5-tetramethyl-2-imidazolidinone was found to be the most rapidly acting bactericide, especially under halogen-demand-free conditions. The mixed N,N'-dihalamine 1-bromo-3-chloro-4,4,5,5-tetramethyl-2-imidazolidinone was found to be intermediate in terms of rate of disinfection, while the compound 1,3-dichloro-4,4,5,5-tetramethyl-2imidazolidinone was observed to be the slowest acting bactericide. When overall effectiveness was judged on the basis of stability of the disinfectants along with rates of disinfection, the mixed halamine was considered to exhibit great potential for use as a disinfectant in an aqueous solution.

Metabolomic profiling can differentiate between bactericidal effects of free and polymer bound halogen

“…Chlorinated compounds have been used for disinfection purposes since the early 1900s due to their effective bactericidal action 1. They can act either as free small species, such as HOCl or NaOCl (which are considered to be the most effective disinfectants for water and clinical purposes),2–5 attached to amino containing compounds ( N ‐halamines), such as halogenated isoxazoles and halogenated imidazoles,6–11 or attached to high molecular weight compounds ( N ‐halamine polymers) 12–16…”

“…It has been proposed that the action of halogenated heterocyclic compounds ( N ‐halamines) depends on halogen ion exchange between these compounds and the bacterial cell membrane by contact, resulting in cellwall oxidation 6–11. The same explanation has been suggested for the mode of action of N ‐halamine biocidal polymers, but it is still not clear whether the halogen ion is delivered to the bacterial cells by contact,12, 13 halogen ion release22 or a combination of both 16.…”

Effect of organic N-halamines on selected membrane functions in intact Staphylococcus aureus cells

“…Disinfectant (10 ppm of total chlorine [final concentration]) was added to the cell suspension 5 to 10 min before the acid pulse. It should be noted that the ratio of cells to disinfectant was approximately 100 to 500 times that ratio used when disinfection kinetics experiments were performed (22)(23)(24).…”

“…Most of the work conducted has involved the assessment of biocidal activity of the compounds rather than investigations of the possible mode of action of these compounds. It has been shown that the halamine disinfectants discussed have a wide range of biocidal activities based on the compound, pH, water quality (high halogen demand versus demand free), temperature, and test organism (15,19,(23)(24)(25)(26)(27).…”

Synthesis of novel pyridinium N‐chloramine precursors and its antimicrobial application on cotton fabrics

“…In this regard, antimicrobial agents including Ag nanoparticles, polybiguanides, chitosan, quaternary ammonium salts (QAs), and N ‐chloramines have been thus successfully incorporated into cotton fabrics. Among these biocides, both QAs and N ‐chloramines have been widely used either in aqueous or by immobilization on substrate surface . However, QAs are usually regarded as incompatible with anion surfactant, and bacterial resistances to QAs have been reported, which may greatly restrict its applications.…”