In an attempt to find novel antifungal agents with improved activity, a series of compounds bearing 6-chloromethyl-3-hydroxy-2-substituted 4H-pyran-4-one moiety were synthesized and examined for their cytotoxic evaluation and antifungal activities against both standard and isolated dermatophytic fungal species Microsporum gypseum, Trichophyton mentagrophytes var. erinacei and Epidermophyton floccosum.