Abstract Schiff bases (SB1–SB3) were synthesized from the condensation of 6-formyl-7-hydroxy-5-methoxy-2-methylbenzopyran-4-one with 2-aminopyridine (SB1), p-phenylenediamine (SB2) and o-phenylenediamine (SB3), while Schiff bases (SB4–SB6) were synthesized by condensation of 5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one with 2-aminopyridine (SB4), p-phenylenediamine (SB5) and o-phenylenediamine (SB6). Schiff bases were characterized using elemental analysis, IR, UV–Vis, 1H NMR, 13C NMR and mass spectroscopy. These compounds were screened for antibacterial activities by micro-plate assay technique. Escherichia coli and Staphylococcus capitis were exposed to different concentrations of the Schiff bases. Results showed that the antibacterial effect of these Schiff bases on Gram-negative bacteria were higher than that on Gram-positive bacteria moreover, the Schiff bases containing substituent OCH3 on position five have higher antibacterial activity than that containing hydroxy group on the same position.