The increasing incidence of bacterial drug resistance imposes a new search on existing antimicrobial drugs leading to the development of new bioactive molecules. In continuation to this, the present article deals with the synthesis and antimicrobial activity of 1-(1-(1H-benzo [d]imidazol-2-yl)ethylideneamino)-6-(arylideneamino)-4-(2 hydroxyphenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles (4a–k). All newly synthesized compounds have been evaluated against two gram positive bacteria (Staphylococcus aureus, Streptococcus pyogenes), two gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa), and three fungi (Candida albicans, Aspergillus niger, Aspergillus clavatus) using serial broth dilution method. Compounds reported in the present article bearing chloro and hydroxy groups exhibit very good to excellent antimicrobial activity. All the newly synthesized compounds have been characterized by IR, 1 H NMR, 13C NMR, and mass spectra.