Substituted phenols as the starting materials were transformed into substituted chromanones by substitution reaction and cyclization reaction, and then 3-(hydroxymethylene)chroman-4-ones were synthesized from substituted chromanones by condensation reaction; at last, the target compounds were synthesized from 3-(hydroxymethylene)chroman-4-ones by chlorination reaction. Their structures were confirmed by 1H NMR and MS. The antifungal activity of the target compounds in vitro was measured by consecutive double dilution, and the result of antifungal experiment indicated that the target compounds had good antifungal action on most fungi tested in vitro. The MIC value of compounds 4c, 4e, 4g and 4h on M. gypseum is 1 microg x mL(-1), better than fluconazole and amphotericin B.