Green Synthesis, Characterization, In Silico Molecular Docking and Biological Evaluation of Imidazolylchalcones as Promising Fungicide/s and Nematicide/s

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Abstract

Chalcones and their derivatives have garnered attention due to their broad-spectrum biological activities. In this study a series of 15 imidazolylchalcone derivatives were synthesized by Claisen-Schmidt condensation of benzaldehydes and 4-(Imidazol-1-yl) acetophenone through ultrasonication as green synthesis. These compounds were characterized by various spectroscopic techniques, namely 1 H-NMR, 13 C-NMR and LC-HRMS. These molecules were evaluated for their fungicidal activity against Rhizoctonia solani & Fusarium oxysporum and nematicidal activity against Meloidogyne incognita . The result revealed that compound IC-8 ((E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(4-benzyloxy)phenyl)prop-2-en-1-one) exhibited the most potent fungicidal activity, with an ED 50 value of 0.69 µg mL − 1 , significantly lower than the ED 50 value (3.57 µg mL − 1 ) of commercially available hexaconazole 5% SC fungicide against R. solani , while IC-4 ((E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(2-bromophenyl) prop-2-en-1-one; ED 50  = 119.22 µg mL − 1 ) showed highest activity against F. oxysporum as compared with the positive control Carbendazim 50% Wettable powder (WP; ED 50  = 9.01 µg mL − 1 ). The compound IC-6 ((E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(3-nitrophenyl) prop-2-en-1-one; LC 50  = 33.62 µg mL − 1 ) was found to be most active against M. incognita (LC 50  = 31.25 µg mL − 1 ) after 24 h of inoculation but lesser active than positive control Velum Prime 34.48% SC (Fluopyrum; LC 50  = 3.46 µg mL − 1 ). Molecular docking studies of imidazolylchalcone derivative-based structural isomers were carried out against cutinase of fungi and acetylcholinesterase (AChE) enzyme of nematode as primary targets. The binding potential of target compounds was investigated by using AutoDock Vina. Ligands were ranked according to their binding affinities via BIOVIA Discovery Studio. Ligand-protein interactions strengthened results of biological evaluation that predicted compound IC-8 as the most active with highest binding energy (-8.5 kcal mol − 1 ) against R . solani , IC-4 (-8.0 kcal mol − 1 ) against cutinase of F . oxysporum and IC-6 (-9.7 kcal mol − 1 ) with acetylcholinesterase (AChE) of M . incognita .

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