16. N-Haloalkylthio compounds

Excerpt

N-Holoalkylthio compounds with antimicrobial activity are obtained in almost any desired number according to the following reaction scheme, provided that the H atom has acidic character: The most important microbicides within this substance class are the compounds bearing a trihalomethylthio group (S-CX₃) as toxophor. The antimicrobial efficacy of _N-haloalkylthio compounds is based on the capacity of the N-S bond to open and react with nucleophilic components of the microbial cell (Paulus & Kühle, 1986). The most effective compounds are those containing the S-CCl₂F group. These also contrary to the trichloromethylthio derivatives do not show mutagenic activities (Schuphan et al.​, 1981). Optimum antimicrobial activity is achieved with compounds whose N-S bond has a medium stability.¹ Taking account of the facts mentioned, it is possible to select from the wide range of N-haloalkylthio compounds already available, microbicides with such chemico-physical and toxicological properties as are suited to defined uses, e.g. as fungicides and algicides in plastics, paint films, wood preservatives and antifouling coatings. …