N-Haloalkylthio compounds

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:

$$ {\rm R}_1 {\rm R}_2 {\rm N - H}\,{\rm + }\,{\rm Cl - S - alkylX}\, \to \,{\rm R}_1 {\rm R}_2 \,{\rm Cl - S - alkylX}\,{\rm + }\,{\rm HCl}\,\,\,\,\,\,\,\,\,{\rm X}\, = \,{\rm halogen} $$

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.¹Taking...