The key intermediate 7-methoxybenzofuran-2-carboxyl ic acid ethyl ester ( 1 ) was synthesized starting from ortho- vanillin and diethyl bromomalonate, which was conve rted into 7-methoxy-benzofuran-2-carboxylic acid hy drazide ( 2 ) by treating with hydrazine hydrate in presence of ethanol. Further the compound ( 2 ) in acetic acid medium got cyclised with substituted benzaldehyde in presence of ammonium acetate to form the 3-(7-methoxybenzofu ran-2-yl)- 5-aryl-4H-[1,2,4]triazole 3 (a-k) . Structural assignments of these compounds have b een made on the basis of elemental analysis, IR, 1 H NMR and GCMS spectral data. All the compounds syn thesized have been screened for antimicrobial and DNA cleavage activities. Some of them gave encouraging results.