A series of (benzamidostyryl)benzimidazole derivatives were synthesized by hydrolyzing 2-phenyl-4-(substituted)benzylidene-5-oxazolones, the azlactone precursors in an acidic medium and treating the product with substituted o-phenylenediamine (OPDA) in situ. The structures of the synthesized compounds were confirmed by spectral and elemental analyses. All synthesized compounds were screened for their in vito antimicrobial activities against some identifiable strains. Thereby, it was found that only nitro substituted benzimidazoles exhibited good to moderate antibacterial activity, while other derivatives were devoid of any antimicrobial effect.