Methods were developed for the synthesis of a series of new thioethers, interesting for medical chemistry, by reacting 4-fluorothiophenol, 2-mercaptobenzoxazole and 5-methoxy-2-mercaptobenzimidazole with 3-aryl-5-(chloromethyl)-1,2,4-oxadiazoles. The conditions for the oxidation of the obtained thioethers into the corresponding sulfones were selected. Analysis of the results of screening of the prepared derivatives against sensitive strains of Escherichia coli, Pseudomonas fluorescens, Staphylococcus aureus, Bacillus cereus and Candida albicans showed the presence of high and moderate antibacterial activity in a number of compounds in drug concentrations up to 250 μg/mL.