Abstract Fluoro and trifluoromethyl derivatives of 1, 2-benzisothiazol-3 (2H)-ones and the 2, 2′-dithiobis (benzamides) have been prepared and their antifungal and antibacterial activity evaluated. Several compounds were found highly active against fungi and Gram- positive microorganisms and a few derivatives displayed some activity against Gram- negative strains. Structure-activity relationships are proposed.