Since the presence of the 1,4-benzodioxane, isoxazole and pyrazole moiety seems to be responsible for the antibacterial property, the series of 1,4-benzodioxinylisoxazole and 1,4-benzodioxinylpyrazole derivatives have been synthesized, characterized and tested their antibacterial activity. The synthesis of new 1,4-benzodioxinylisoxazole and 1,4-benzodioxinylpyrazole derivatives was carried out by chalcone route. This route attracts attention because of its simple operating conditions and easy availability of the chemicals. The title compounds were screened for antibacterial activity. Among the synthesized compounds (4a-j) and (5a-j), some of title compounds exhibited significant activity and few compounds showed moderate and less activity against screened bacterial strains compared to standard. The structures of the title compounds were confirmed by Infrared Spectroscopy (IR), Nuclear Magnetic Resonance (NMR) and mass spectroscopy methods. The synthesized compounds were tested for antibacterial activity. The synthesized compounds were screened for antibacterial activity.