Chalcones are known for their broad biological activities, which can be enhanced by incorporating heterocyclic moieties. Imidazole, recognized for its diverse properties, was introduced into a series of imidazolylchalcone derivatives (3a-3o) synthesized via Claisen-Schmidt condensation of benzaldehydes (2a-2o) and 4-(Imidazol-1-yl) acetophenone (1a) using ultrasonication as a green method. These compounds were characterized by spectroscopic techniques such as 1H-NMR, 13C-NMR, LC-HRMS and evaluated for fungicidal and nematicidal activity. Compound 3 h showed highest fungicidal activity against Rhizoctonia solani (ED₅₀ = 0.69 μg/mL), outperforming commercial hexaconazole (ED₅₀ = 3.57 μg/mL). Compound 3d exhibited the highest activity against Fusarium oxysporum (ED₅₀ = 119.22 μg/mL), while 3f was most effective against Meloidogyne incognita (LC₅₀ = 33.62 μg/mL), though less active than commercial Velum Prime (LC₅₀ = 3.46 μg/mL). The compounds potential activity may results from interactions of electronegative atom with enzyme active sites via hydrogen bonding. Docking studies against fungal cutinase and nematode acetylcholinesterase supported the in-vitro findings. Promising compounds will undergo further in-vivo and field trials for antifungal and antinemic applications and developed a potent molecule.