Abstract <p>A new series of Schiff base was synthesized via acid-catalyzed condensation of 1,3-diphenyl-1<i>H</i>-pyrazole-4-carbaldehydes with 4<i>H</i>-1,2,4-triazol-4-amine. The structures of the compounds were confirmed by ¹H and ¹³C NMR spectroscopy. Antimicrobial screening revealed that nitro and bromo substituted derivatives exhibited the most potent antibacterial and antifungal activities, with minimum inhibitory concentrations comparable to ciprofloxacin and fluconazole. Structure-activity relationship (SAR) analysis indicated that electron-withdrawing substituents significantly enhanced biological activity, while methoxy-substituted analogues displayed moderate efficacy. Molecular docking studies against bacterial DNA gyrase (PDB ID: 1KZN) demonstrated strong binding affinities (from –8.8 to –9.4 kcal/mol) and stable interactions with active-site residues, corroborating the experimental findings. Collectively, these results establish pyrazole–triazole Schiff bases as promising antimicrobial scaffolds, providing a rational basis for future pharmacological development and structural optimization.</p>