Resorcinol was reacted with dl-malic acid or ethyl acetoacetate under the catalysis of sulfuric acid via Pechmann condensation to produce three umbelliferone (7-hydroxycoumarin) analogs 5～7. 5a, 6a and 7a were synthesized by methylation of 5～7. Fourteen new coumarin compounds 5b～5e, 6b～6f and 7b～7f were prepared from the intermediates and alkyl halides via Williamson reaction using TBAB (tetrabutylammonium bromide) as catalyst. The structures of all those new compounds were confirmed by ¹H NMR, IR, MS techniques and elemental analysis. The preliminary bioassay showed that, compound 6 had inhibitory activity 58.5% against Phytophythora capsici, 7c had antifungal activity 54.0% against Botrytis cinerea and 6c had antifungal activity 83.7.0% against Rhiazoctonia solani at 50 μg/mL.

Key words: umbelliferone, coumarin, synthesis, inhibitory activity