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

Green Synthesis, Characterization, In Silico Molecular Docking and Biological Evaluation of Imidazolylchalcones as Promising Fungicide/s and Nematicide/s | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Green Synthesis, Characterization, In Silico Molecular Docking and Biological Evaluation of Imidazolylchalcones as Promising Fungicide/s and Nematicide/s Rakesh Kumar, Parshant Kaushik, Kailashpati Tripathi, Rajni Godara, and 9 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-5803429/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 29 Apr, 2025 Read the published version in BMC Chemistry → Version 1 posted 4 You are reading this latest preprint version 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 . Green Synthesis Imidazolylchalcones Ultrasonication Molecular Docking Fusarium oxysporium Rhizoctonia solani Meloidogyne incognita Figures Figure 1 Figure 2 Figure 3 Figure 4 1. Introduction In modern agriculture, emerging diseases caused by fungi, bacteria, viruses, and nematodes pose a severe threat to global crop production, affecting yield and quality. Trade globalization and climate change have accelerated the spread of these infections, intensifying the challenge to food security and economic stability, especially in agriculture-dependent regions of world (Oraon et al., 2024). Pests and pathogens destroy 40–50% of crop yields, with plant diseases responsible for about a quarter of these losses (Khan et al., 2021) and plant parasitic nematodes cause an estimated 12.3% annual yield loss in global food production, valued at $157 billion (Hassan et al., 2013). The most devastating vegetable diseases include root rot, damping-off, charcoal rot, and wilt, are caused by pathogens like Rhizoctonia solani , Alternaria solani , Fusarium oxysporum , Sclerotium rolfsii , Macrophomina phaseolina , and Pythium spp (El-Kazzaz et al., 2022). Among vegetables, Solanum melongena (brinjal) is highly vulnerable to pre- and post-emergence damping-off, root rot ( R. solani ) and wilt ( F. oxysporum ) of seedlings at nursery stage of crop. These soil-borne fungi cause severe plant mortality and significant crop losses, impacting food security and farmers' livelihoods (Singh et al., 2014). Similarly, Meloidogyne incognita (Root-knot nematode), also causes severe damage to crop roots, disrupting nutrient uptake and reducing plant vigor, often leading to crop failure. In India, it is responsible for a 21% yield loss in brinjal (Gawade et al., 2022). While, over the past three decades, natural products from diverse microbial sources and botanicals have been explored for control of pests and diseases (Kumar et al., 2021). However, due to narrow spectrum, low stability and low efficacy are limitation for immediate control of pests. Therefore, the importance of synthetic agrochemicals such as fungicides, insecticides, antimicrobial agents, herbicides, nematicides, seed protectants, insect repellents and rodenticides cannot be overstated, especially considering that certain insect pests have developed resistance to specific chemicals (Brevik et al., 2018). Synthetic pesticides have also shown limitations, such as health risks, pesticide residues, environmental impact, and the emergence of resistant pathogens. Additionally, climate change has affected the efficacy of these chemicals (Ul Haq et al., 2020). To overcome resistance, there is a need to synthesize safe, broad spectrum, efficient, cost-effective and potential bioactive molecule/s to control pests and diseases (DeVito, 2016). In recent years, there has been growing interest in environment friendly synthesis of synthetic agrochemicals. The application of ultrasound irradiation as an alternative energy source or green organic synthesis has gained significant interest with a focus on multicomponent reactions at ambient reaction conditions, eco-friendly solvents and catalyst-free synthesis of bioactive heterocyclic scaffolds (Karmakar and Mukhopadhyay, 2021 and Puri et al., 2013). In the present study compounds were synthesized via ultrasonication and compared with the conventional methodology for their yield and time. Chalcones, a class of naturally occurring flavonoids, have emerged as potent bioactive molecules with a wide range of biological activities, including antifungal, antiparasitic, antibacterial, insecticidal, nematicidal, antioxidant, antiplasmodial, antitumor, and anthelmintic activities (Shakil et al., 2010, 2011, 2013). The structural diversity of chalcones and their ease of modification make them attractive candidates for the development of new agrochemicals (Yadav et al., 2019). Chalcones are α,β-unsaturated ketones characterized by the presence of two aromatic rings connected by a three-carbon α,β-unsaturated carbonyl system. This unique structure enables chalcones to exhibit various mechanisms of action, including enzyme inhibition, cell membrane disruption, and the generation of reactive oxygen species (Godara et al., 2024). Furthermore, the introduction of heterocyclic moieties into the chalcone framework has been shown to enhance their biological activity. Imidazole, a five-membered heterocycle containing two nitrogen atoms, is one such moiety that has attracted significant attention due to its presence in a wide range of biologically active compounds (Siwach and Verma, 2021). Imidazole derivatives are known for their antibacterial, anti-inflammatory, antidiabetic, antiparasitic, antituberculosis, antifungal, antioxidant, antitumor, antimalarial, anticancer, antidepressant properties (Tolomeu and Fraga, 2023; Rani et al., 2013) making them ideal candidates for the development of new agrochemicals or therapeutic agents. In this context, imidazolylchalcones, a class of chalcones with an imidazole ring, can represent a promising avenue for the development of novel agrochemical. The introduction of the imidazole ring into the chalcone structure is expected to enhance the biological activity of the resulting compounds by improving their ability to interact with biological targets. In this study, we report an eco-friendly synthesis of imidazolylchalcone derivatives via Claisen-Schmidt condensation using ultrasonication and compared with conventional synthetic approach, followed by evaluation against plant pathogenic fungi, F. oxysporum , R. solani and root knot nematode, M. incognita . Simultaneously, we carried out a computational modelling or docking study by simulating the binding of imidazolylchalcones to key enzymes, such as fungal cutinase and nematode acetylcholinesterase (AChE) to predict/identify lead compounds with high binding affinity and potential for biological efficacy. 2. Materials and Methods 2.1 Chemicals and Instruments Benzaldehydes, 4-(Imidazol-1-yl) acetophenone were obtained from Sigma-Aldrich and used without further purification. Analytical grade solvents and chemicals were used. Thin layer chromatography (TLC) was used to monitor reactions on 200 mm thick aluminium sheets of Merck silica gel 60F 254 and spots were visualised under UV light. A Heidolf rotary evaporator was employed for solvent removal. 1 H-NMR and 13 C-NMR spectra were obtained on a JEOL 400 MHz Spectrospin spectrometer, with tetramethylsilane (TMS) serving as an internal standard for calibration. Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS) was performed using an AB SCIEX Triple TOFTM 5600+ apparatus with TurboIonSpray (TIS), SCIEX ExionLC, and a PDA detector. A C 18 column (2.7μm, 4.6x100 mm) was utilised for compound separation. The column was eluted with Methanol: Water (98:2% (v/v) containing 0.1% formic acid at a flow rate of 1.0 mL/min and a column oven temperature of 40 °C. Ultrasonic bath (Labman Scientific Instruments) was used for synthesis and cleaning of glasswares. Melting point was recorded in Buchi M-560 instrument and were uncorrected. 2.2 Methods of Synthesis 2.2.1 Conventional synthesis of imidazolylchalcones (Single step reaction) The imidazolyl chalcone series was synthesized via base-catalyzed Claisen-Schmidt reaction using the method described by Liu et al., (2013). Equimolar amounts of selected benzaldehydes were dissolved in 5 mL of 40% ethanolic NaOH solution in a round-bottomed flask and stirred at room temperature for 10 minutes. After that, 4-(Imidazol-1-yl) acetophenone (dissolved in 5 mL of ethanol) was added dropwise with continuously stirring on magnetic stirrer. The stirring duration ranged from 1 to 28 h for different reactions at room temperature, as shown in Scheme I . After the reaction was complete, the reaction mixture was neutralized with 2M HCl, resulting in the formation of a creamy white or light-yellow precipitate. This precipitate was separated by filtration and rinsed with cold water. In case of no precipitate formation, the reaction mixture was extracted with ethyl acetate (30 mL × 3). The organic layer was dehydrated using anhydrous Na 2 SO 4 and solvent was removed using a rotary evaporator, leaving behind a viscous residue. 2.2.2 Ultrasonic synthesis of imidazolylchalcones (Single step reaction): Equimolar amounts of 4 -(Imidazol-1-yl) acetophenone (100 mg, 0.537 mmol) in 40% ethanolic KOH (5 mL) was taken in 250 mL round bottom flask and ethanolic solution of the different benzaldehydes were added. RB flask was fixed with burette stand in ultrasonic bath at temp. 25-30 o C, frequency 40 KHz with time range, 5-90 min., depending on the compounds listed in Table 1 and the reactions were monitored by TLC in ethyl acetate: hexane (2:8) solvent systems. After completion of reaction, reaction mixture was worked up as described in conventional method. Crude product purified through column chromatography on silica gel, using a solvent mixture of hexane and ethyl acetate with increasing polarity. The desired compound was eluted with a solvent mixture containing 10% ethyl acetate and hexane. Table 1: Different substituents of imidazolylchalcone derivatives Compounds X IC-1 2,6-Cl IC-2 4-F IC-3 4-Br IC-4 2-Br IC-5 2-NO 2 IC-6 3-NO 2 IC-7 4-NO 2 IC-8 4-OCH 2 -C 6 H 5 IC-9 4-OCH 3 IC-10 3-Cl IC-11 2,4-Cl IC-12 2-Cl IC-13 3-OH IC-14 4-OH IC-15 3,4,5-OCH 3 2.3 Spectral analysis of imidazolylchalcone derivatives 2.3.1 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(2,6-dichlorophenyl) prop-2-en-1-one (IC-1) Creamy yellow solid; m.p.: 149-151 o C, R f : 0.56 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.28 (d, J = 16.8 Hz, H-3), 8.02 – 7.92 (3H, m, Ar-H’), 7.89 (1H, d, J = 16.8 Hz, H-2), 7.84 – 7.63 (4H, m, Ar-H”), 7.37 – 7.20 (2H, m, H-4’” & H-5’”), 7.11 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO-D 6 ) δ 198.01(C1), 143.54(C3), 140.76(C4”), 136.26(C1”), 135.07(C1’, C2’”), 131.90(C2’, C6’), 130.94(C2”, C3”, C5”, C6”), 130.45(C4’”), 128.22(C3’, C5’), 126.38(C4’), 120.20(C2), 118.29(C5’”). HRMS for C 18 H 12 Cl 2 N 2 O [M+H] + m/z : Calcd 343.0394; Observed 343.0399. 2.3.2 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-fluorophenyl) prop-2-en-1-one (IC-2) Yellow-brown solid; m.p.: 144-145 o C, R f : 0.55 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.35 (1H, d, J = 16.7 Hz, H-3), 8.28 – 8.09 (4H, m, Ar-H”), 7.94 (1H, d, J = 16.7 Hz, H-2), 7.63 – 7.40 (6H, m, Ar-H’ & H-4’”, H-5’”), 7.16 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO- D 6 ) δ 189.70 (C-1), 162.15 (C-4’), 143.65 (C-3), 142.83 (C-4”), 137.49 (C-1”), 135.60 (C-2’”), 130.70 (C-2’, C-6’), 130.40 (C-2”, C-3”, C-5”, C-6”), 129.93 (C-1’), 129.48 (C-4’”), 121.30 (C-2), 118.20 (C-5’”), 115.40 (C-3’, C-5’). HRMS for C 18 H 13 FN 2 O [M+H] + m/z : Calcd 293.1084; Observed 293.1085. 2.3.3 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-bromophenyl) prop-2-en-1-one (IC-3) White solid; m.p.: 161-162 o C, R f : 0.57 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.02 (1H, d, J = 15.7 Hz, H-3), 7.96 – 7.77 (8H, m, Ar-H’ &Ar-H”), 7.70 (1H, d, J = 15.7 Hz, H-2), 7.66 – 7.59 (2H, m, H-4’” & H-5’”), 7.13 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO-D6) δ 188.22 (C-1), 143.37 (C-3), 140.86 (C-4”), 136.32 (C-1”), 135.85 (C-2’”), 134.49 (C-1’), 132.42 (C-3’), 132.42 (C-5’), 131.45 (C-2”), 131.45 (C-6”), 131.13 (C-3”), 131.13 (C-5”), 130.95 (C-4’”), 128.52 (C-2’), 128.52 (C-6’), 123.08 (C-4’), 120.31 (C-2), 118.35 (C-5’”). HRMS for C 18 H 13 BrN 2 O [M+H] + m/z : Calcd 353.0311; Observed 353.0284. 2.3.4 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(2-bromophenyl) prop-2-en-1-one (IC-4) Cream yellow solid; m.p.: 121-123 o C, R f : 0.70 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.29 (1H, d, J = 16.9 Hz, H-3), 8.24 – 8.01 (4H, m, Ar-H”), 7.89 (4H, d, J = 16.9 Hz, H-2), 7.86 – 7.67 (4H, m, Ar-H’), 7.56 – 7.24 (2H, m, H-4’” & H-5’”), 7.13 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO- D 6 ) δ 188.12 (C-1), 141.95 (C-3), 140.98 (C-4”), 136.34 (C-1”), 135.65 (C-2’”), 133.85 (C-1’), 132.82 (C-3’), 131.23 (C-2”, C-6”), 130.98 (C-3”, C-5”), 129.42 (C-4’”), 128.77 (C-6’), 126.03 (C-5’), 125.16 (C-4’), 120.32 (C-2’), 120.15 (C-2), 118.33 (C-5’”). HRMS for C 18 H 13 BrN 2 O [M+H] + m/z : Calcd 353.0311; Observed 353.0284. 2.3 .5 (E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(2-nitrophenyl) prop-2-en-1-one (IC-5) Black solid; m.p.: 118-120 o C, R f : 0.56 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.45 (1H, d, J = 15.4 Hz, H-3), 8.42 – 8.34 (4H, m, Ar-H”), 8.18 (1H, d, J = 15.4 Hz, H-2), 8.12 – 7.67 (6H, m, Ar-H’ & H-4’”, H-5’”), 7.12 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO- D 6 ) δ 203.51 (C-1), 147.95 (C-2’), 145.67 (C-3), 143.48 (C-4”), 137.87 (C-1”), 136.12 (C-2’”), 134.70 (C-5’), 131.74 (C-2”, C-3”, C-5”, C-6”), 130.65 (C-4’”), 129.19 (C-4’), 128.37 (C-1’), 126.87 (C-6’), 123.96 (C-3’), 120.85 (C-2), 118.39 (C-5’”). HRMS for C 18 H 13 N 3 O 3 [M+H] + m/z : Calcd 320.1027; Observed 320.1030. 2.3 .6 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(3-nitrophenyl) prop-2-en-1-one (IC-6) Pale-yellow solid; m.p.: 141-143 o C, R f : 0.54 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.44 (1H, s, H-2’), 8.26 (1H, d, J = 15.5 Hz, H-3), 7.95 – 7.85 (3H, m, H-4’, H-5’, H-6’), 7.84 (1H, d, J = 15.5 Hz, H-2), 7.35 – 7.16 (6H, m, Ar-H” & H-4’”, H-5’”), 7.13 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO- D 6 ) δ 197.74 (C-1), 148.22 (C-3’), 142.58 (C-4”), 140.84 (C-3), 136.26 (C-1’), 136.26 (C-1”), 135.52 (C-2’”), 134.97 (C-6’), 130.94 (C-2”), 130.94 (C-6”), 130.47 (C-3”), 130.47 (C-5”), 130.47 (C-4’”), 128.16 (C-5’), 123.12 (C-4’), 120.19 (C-2’), 120.19 (C-2), 118.28 (C-5’”). HRMS for C 18 H 13 N 3 O 3 [M+H] + m/z : Calcd 320.1027; Observed 320.1030. 2.3 .7 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-nitrophenyl) prop-2-en-1-one (IC-7) Light brown solid; m.p.: 165-167 o C, R f : 0.59 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.25 (1H, d, J = 16.4 Hz, H-3), 8.15 – 8.00 (4H, m, Ar-H’), 7.91 – 7.77 (4H, m, Ar-H”), 7.64 (1H, d, J = 16.4 Hz, H-2), 7.57 – 7.41 (2H, m, H-4’” & H-5’”), 7.16 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO- D 6 ) δ 201.17 (C-1), 151.76 (C-4’), 147.01 (C-3), 143.84 (C-4”), 142.11 (C-1’), 136.03 (C-1”), 134.89 (C-2’”), 131.25 (C-2”, C-3”, C-5”, C-6”), 130.43 (C-4’”), 128.16 (C-2’, C-6’), 123.83 (C-3’, C-5’), 120.89 (C-2), 118.89 (C-5’”). HRMS for C 18 H 13 N 3 O 3 [M+H] + m/z : Calcd 320.1027; Observed 320.1030. 2.3. 8 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one (IC-8) Cream white solid; m.p.: 153-155 o C, R f : 0.70 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.25 (1H, d, J = 15.9 Hz, H-3), 7.91 – 7.81 (4H, m, Ar-H”), 7.47 – 7.39 (2H, m, H-4’” & H-5’”), 7.39 – 7.25 (9H, m, Ar-H’ & Ar-Ha’), 7.13 (1H, s, H-2’”), 7.07 (1H, d, J = 15.9 Hz, H-2), 5.15 (2H, s, -OCH 2 ). 13 C NMR (101 MHz, DMSO- D 6 ) δ 188.14 (C-1), 161.04 (C-4’), 144.71 (C-3), 140.64 (C-4”), 137.20 (C-1”), 136.30 (C-1’a), 136.26 (C-2’”), 131.48 (C-2”, C-6”), 130.93 (C-3”, C-5”), 129.02 (C-2’, C-6’), 128.51 (C-4’”), 128.35 (C-3’a, C-5’a), 128.03 (C-4’a, C-1’), 127.25 (C-2’a, C-6’a), 120.28 (C-2), 118.34 (C-5’”), 115.76 (C-3’,C-5’), 69.92 (OCH 2 ). HRMS for C 25 H 20 N 2 O 2 [M+H] + m/z : Calcd 381.1462; Observed 381.1468. 2.3.9 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-methoxyphenyl) prop-2-en-1-one (IC-9) Cream white solid; m.p.: 146-147 o C, R f : 0.57 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.26 (1H, d, J = 16.4 Hz, H-3), 7.97 – 7.62 (10H, m, Ar-H’, Ar-H” & H-4’”, H-5’”), 7.13 (1H, s, H-2’”), 6.98 (1H, d, J = 16.4 Hz, H-2), 3.78 (3H, s, OCH 3 ). 13 C NMR (101 MHz, DMSO- D 6 ) δ 188.15 (C-1), 161.97 (C-4’), 144.78 (C-3), 140.63 (C-4”), 136.27 (C-1”), 135.12 (C-2’”), 131.49 (C-2”, C-3”, C-5”, C-6”), 130.92 (C-2’, C-6’, C-4’”), 127.83 (C-1’), 120.28 (C-2), 118.34 (C-5’”), 114.94 (C-3’, C-5’), 55.93 (-OCH 3 ). HRMS for C 19 H 16 N 2 O 2 [M+H] + m/z : Calcd 305.1314; Observed 305.1318. 2.3 .10 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(3-chlorophenyl) prop-2-en-1-one (IC-10) Pale-yellow solid; m.p.: 142-143 o C, R f : 0.56 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.26 (1H, d, J = 16.9 Hz, H-3), 7.94 – 7.86 (4H, m, Ar-H”), 7.83 (1H, d, J = 16.9 Hz, H-2), 7.33 – 7.17 (6H, m, Ar-H’ & H-4’”, H-5’”), 7.13 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO- D 6 ) δ 188.14 (C-1), 145.87 (C-3), 140.98 (C-4”), 139.19 (C-1”), 136.34 (C-1’), 135.65 (C-2’”), 134.98 (C-3’), 132.66 (C-2”, C-6”), 131.23 (C-3”, C-5”), 130.97 (C-4’”), 130.58 (C-5’), 129.25 (C-4’), 128.24 (C-6’), 125.02 (C-2’), 120.33 (C-2), 118.34 (C-5’”). HRMS for C 18 H 13 ClN 2 O [M+H] + m/z : Calcd 309.0784; Observed 309.0789. 2.3.11 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(2,4-dichlorophenyl) prop-2-en-1-one (IC-11) Brown solid; m.p.: 125-126 o C, R f : 0.55 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.03 (1H, d, J = 16.2 Hz, H-3), 7.86 (1H, s, H-3’), 7.80 (1H, d, J = 16.2 Hz, H-2), 7.75 – 7.65 (6H, m, Ar-H” & H-4’”, H-5’”), 7.52 (1H, d, J = 2.1 Hz, H-5’), 7.50 (1H, d, J = 2.1 Hz, H-6’), 7.11 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO- D 6 ) δ 197.36 (C-1), 140.75 (C-3), 137.60 (C-4”), 136.78 (C-1”), 136.26 (C-2’), 135.30 (C-2’”), 131.60 (C-1’), 130.64 (C-2”, C-3”, C-5”, C-6”), 130.58 (C-6’, C-4’”), 128.13 (C-3’), 126.58 (C-5’), 125.38 (C-4’), 120.19 (C-2), 118.30 (C-5’”). HRMS for C 18 H 12 Cl 2 N 2 O [M+H] + m/z : Calcd 344.0232; Observed 344.0238. 2.3 .12 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(2-chlorophenyl) prop-2-en-1-one (IC-12) Pale-yellow solid; m.p.: 114-116 o C, R f : 0.54 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.29 (1H, d, J = 16.4 Hz, H-3), 8.10 – 8.01 (4H, m, Ar-H”), 7.87 (1H, d, J = 16.4 Hz, H-2), 7.58 – 7.50 (2H, m, H-4’” & H-5’”), 7.49 – 7.37 (4H, m, Ar-H’), 7.13 (1H, s, H-2’”). 13 C NMR (101 MHz, DMSO- D 6 ) δ 188.14 (C-1), 140.98 (C-3), 139.19 (C-4”), 136.34 (C-1”), 135.65 (C-2’”), 134.97 (C-2’), 132.66 (C-1’), 131.23 (C-2”, C-3”, C-5”, C-6”), 130.97 (C-4’”), 130.58 (C-3’), 129.25 (C-4’), 128.24 (C-6’), 125.02 (C-5’), 120.33 (C-2), 118.34 (C-5’”). HRMS for C 18 H 13 ClN 2 O [M+H] + m/z : Calcd 309.0784; Observed 309.0789. 2.3 .13 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one (IC-13) Cream white solid; m.p.: 232-234 o C, R f : 0.57 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.26 (1H, d, J = 15.8 Hz, H-3), 7.96 – 7.87 (4H, m, Ar-H”), 7.84 (1H, d, J = 15.8 Hz, H-2), 7.37 – 7.15 (5H, m, H-4’, H-5’, H-6’ & H-4’”, H-5’”), 7.13 (1H, s, H-2’”), 6.86 (1H, s, H-2’), 5.41(1H, s, -OH). 13 C NMR (101 MHz, DMSO- D 6 ) δ 188.37 (C-1), 158.40 (C-3’), 145.07 (C-3), 140.75 (C-4”), 136.44 (C-1”), 136.31 (C-1’), 136.03 (C-2’”), 131.05 (C-2”, C-3”, C-5”, C-6”), 130.93 (C-5’), 130.41 (C-4’”), 122.15 (C-2), 120.32 (C-6’), 118.48 (C-5’”), 118.34 (C-2’), 115.95 (C-4’). HRMS for C 18 H 14 N 2 O 2 [M+H] + m/z : Calcd 291.0632; Observed 291.0628. 2.3 .14 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (IC-14) Cream yellow solid; m.p.: 247-249 o C, R f : 0.55 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.34 (1H, d, J = 15.8 Hz, H-3), 8.18 – 7.98 (4H, m, Ar-H”), 7.98 – 7.77 (6H, m, Ar-H’ & H-4’”, H-5’”), 7.73 (1H, d, J = 15.8 Hz, H-2), 7.16 (1H, s, H-2’”), 5.57(1H, s, -OH). 13 C NMR (101 MHz, DMSO- D 6 ) δ 197.62 (C-1), 157.58 (C-4’), 144.76 (C-3), 138.79 (C-4”), 137.40 (C-1”), 135.38 (C-2’”), 130.51 (C-2”, C-3”, C-5”, C-6”, C-2’, C-6’), 130.01 (C-4’”), 127.42 (C-1’), 122.28 (C-2) 118.47 (C-5’”), 115.80 (C-3’, C-5’). HRMS for C 18 H 14 N 2 O 2 [M+H] + m/z : Calcd 291.0632; Observed 291.0628. 2.3 .15 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(3,4,5-trimethoxyphenyl) prop-2-en-1-one (IC-15) Yellow brown solid; m.p.: 135-137 o C, R f : 0.56 (Hexane: ethyl acetate, 1:4). 1 H NMR (400 MHz, DMSO- D 6 ) δ 8.28 (1H, d, J = 16.8 Hz, H-3), 7.88 (1H, d, J = 16.8 Hz, H-2), 7.78 – 7.35 (6H, m, Ar-H” & H-4’”, H-5’”), 7.23 (2H, s, H-2’ & H-6’), 7.14 (1H, s, H-2’”), 3.83 (9H, s, -OCH 3 ). 13 C NMR (101 MHz, DMSO- D 6 ) δ 188.33 (C-1), 153.63 (C-3’, C-5’), 145.31 (C-3), 140.74 (C-4”), 140.31 (C-4’), 136.33 (C-1”), 136.02 (C-2’”), 131.06 (C-2”, C-3”, C-5”, C-6”), 130.95 (C-4’”), 127.51 (C-1’), 120.32 (C-2), 118.36 (C-5’”), 107.16 (C-2’, C-6’), 60.68 (4’-OCH 3 ), 56.66 (3’-OCH 3 & 5’-OCH 3 ). HRMS for C 21 H 20 N 2 O 4 [M+H] + m/z : Calcd 365.0839; Observed 365.0842. 2.4 Antifungal bioassay: Imidazolylchalcone derivatives were assessed for their antifungal properties in vitro against R. solani and F. oxysporum using the poisoned food technique (Nene and Thapliyal, 1979). The fungal strains, F. oxysporum ITCC 8113 and R. solani ITCC 7479 were obtained from ITCC (Indian Type Culture Collection), Division of Plant Pathology, ICAR-IARI, New Delhi, India. These cultures were kept at 27°C for 4-7 days on PDA (Potato Dextrose Agar) slants and were regularly subcultured to maintain their viability and purity. The stock solution of synthesized compounds (1000 μg mL -1 ) was prepared in DMSO. An in vitro bioassay was carried out at five different concentrations namely 200, 100, 50, 25 and 12.5 μg mL -1 using freshly prepared PDA media in quadruplicate. Positive controls for F. oxysporum and R. solani were carbendazim 50% WP (Wettable Powder) and Hexaconazole 5% SC (Soluble Concentrate), respectively. Fungal spores and mycelium were taken from subcultured fungal cultures using a 5-mm-thick disc, which was then inoculated in Petri dishes under laminar flow (sterile conditions). The treatment and control Petri dishes were placed in a BOD incubator at 25±1°C. Incubation was continued until the fungal growth completely covered or reached an advanced stage in the control Petri dish, which usually took about 4-5 days for R. solani and 10-12 days for F. oxysporum (Kaushik et al., 2021). Percentage inhibition was calculated by measuring colony diameter of fungi (Abbott, 1925). I = {(C - T)/C} × 100 Where, I represent inhibition percentage, C for mean diameter (cm) of growth of fungal colony in control and T for treated Petri dishes. The corrected percentage inhibition (IC) was determined with the following equation: IC = (I−CF)/(100−CF) ×100 Here, CF is calculated as: CF = [(90 – C)/C] × 100 Where, 90 is Petri plate diameter (mm) and C represent fungal mycelial growth (mm) in control plate. 2.5 Nematicidal bioassay All synthesized compounds were evaluated for in vitro nematicidal activity using a water screening method. M. incognita infected root galls were obtained from glasshouse of Division of Nematology, ICAR-Indian Agricultural Research Institute, New Delhi. For extraction of nematode culture, galls were incubated at 25-30 °C for 2-3 days, which facilitate the hatching of eggs. Subsequently, nematode population counted and 100 J2s per mL was prepared through dilution. Synthesized compound’s stock solution of 1000 μg mL -1 was prepared in DMSO. The five test concentrations (200, 100, 50, 25 and 12.5 µg mL -1 ) were prepared through serial dilution from stock solution. Velum prime was taken as positive control for M. incognita . A 1 mL suspension of nematodes (J2s) with 1 mL of test compound of different concentrations were added into 24-well culture plates and incubated at 28±2 °C in BOD in triplicates. Both living and dead J2s nematodes were counted in each treatment using a counting dish under stereoscopic binocular microscope. The mortality of J2s nematodes was recorded at 24, 48, 72 and 96 h (Yadav et al., 2021 and 2022; Kumar et al., 2023). The mortality rate was determined by Abbott's formula (Abbott, 1925). Corrected mortality percentage = [(T - C) / (100 - C)] × 100 Here, T and C represents total mortality in the treatment and control, respectively. ED 50 values (effective dose for 50% inhibition) for antifungal and LC 50 values (lethal concentration for 50% inhibition) for nematicidal activities were expressed in µg mL -1 , computed by probit analysis using the SPSS statistical package (version 28.0). 2.6 Molecular docking: Molecular docking is an essential tool for drug and agrochemical discovery, helping in virtual screening of potential candidates as well as providing insights into the mechanism of action of a certain compound (Tripathi et al., 2024). In this study, cutinase and elongation factor proteins were selected as targets for the fungicidal activity whereas acetylcholinesterase was chosen as a target site for nematicidal action. Cutinase and elongation factor both play a crucial role in growth, survival, and virulence of both the fungi. Hence, these enzymes are a potential target for developing new antifungal agents. Similarly, acetylcholinesterase is one of the most important enzyme responsible for maintaining steady transfer of nerve signal, making it a potential target site for various pests including nematodes (Godara et al., 2024). The target enzyme sequences were obtained from the NCBI database (https://www.ncbi.nlm.nih.gov/) and used for homology modeling with the SWISS-MODEL tool (https://swissmodel.expasy.org/). Protein and ligand preparation was conducted using AutoDock Vina. For protein preparation, water molecules were removed, polar hydrogens were added, and appropriate charges were assigned. The two-dimensional structures of the ligand compounds were initially created using ChemDraw Ultra 12.0, and subsequently converted to three-dimensional structures using Chem3D Pro 12.0, followed by energy minimization. These structures were then saved in pdb format using PyMOL and further processed for molecular docking in AutoDock Vina. Following the docking simulations, ligands were ranked based on their binding affinities. Detailed analyses of the most favorable ligand-protein interactions were performed using BIOVIA Discovery Studio. 3. Results and Discussion 3.1 Synthesis and characterization Fifteen imidazolylchalcone derivatives were synthesized successfully using both conventional and ultrasonic methods ( Scheme 1 ). The ultrasonication method showed shorter reaction times ( Figure 1 ) and higher yields compared to the conventional approach ( Table 2 ). In imidazolylchalcones ( IC-1 to IC-15 ), two characteristic doublets of olefinic protons appeared at approximately 7.82 (1H, d, J = 15.9 Hz, H-3) and 7.67 (1H, d, J = 15.9 Hz, H-2) in the 1 H-NMR spectrum of all the compounds, confirming the formation of chalcones. In 13 C-NMR, the peak at δ 188.14-203.51 (C-1) for the carbonyl moiety and peaks at δ 140.75-147.01 (C-3) and 120.15-122.28 (C-2) for the olefinic carbon atoms of imidazolylchalcone were observed. The multiplet present between δ 7.16-8.42 (4H, m, Ar-Hʹʹ) indicates the presence of a phenyl ring at the carbonyl carbon atom in the 1 H-NMR spectra of all the derivatives. A characteristic peak at 7.11-7.13 (H2’”) and the multiplet between δ 7.15-8.12 (H3’” & H4’”) confirmed the presence of imidazolyl ring. The multiplet appearing between δ 7.17-8.15 (Ar-H’) showed the presence of a substituted phenyl ring connected to the C-3 carbon and the chemical shift of this ring was influenced by different substituents like halo, nitro, hydroxy and methoxy groups. Characteristic singlets between δ 3.78-3.83 indicated the presence of methoxy groups in the compounds IC-9 and IC-15. Similarly, compounds IC-13 and IC-14 showed characteristic singlet between 5.41- 5.57, due to the presence of hydroxy group. The structures of all the compounds were further confirmed by 13 C-NMR spectra, which matched well with the respective carbon atom values. Table 2: Comparison of reaction time and yield of ultrasonic and conventional methods of imidazolylchalcones Compounds Conventional method Ultrasonication method Reaction time (min) Yield (%) Reaction time (min) Yield (%) IC-1 30 84 5 92 IC-2 130 79 40 91 IC-3 70 81 30 88 IC-4 25 80 5 87 IC-5 170 77 60 84 IC-6 230 72 70 85 IC-7 210 74 90 87 IC-8 120 81 40 89 IC-9 90 79 30 86 IC-10 110 76 50 84 IC-11 105 80 40 91 IC-12 60 85 20 91 IC-13 150 83 50 92 IC-14 170 84 60 89 IC-15 250 74 90 82 3.2 Antifungal activity The in vitro results of antifungal activity of synthesized imidazolylchalcone derivatives against R. solani and F. oxysporum are presented in Table 3 and Table 4 . It showed 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 , followed by IC-10 (ED 50 =2.28 μg mL -1 ), IC-7 (ED 50 =4.35 μg mL -1 ) and IC-11 (ED 50 =6.75 μg mL -1 ) ( Figure 2 ). However, in case of F. oxysporum bioassay, compound 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 followed by IC-3 (ED 50 =135.76 μg mL -1 ), IC-12 (ED 50 =319.15) and IC-1 (ED 50 =361.62 μg mL -1 ) as compared to positive control, Carbendazim 50 % WP (ED 50 =9.01 μg mL -1 ) ( Figure 3 ). Table 3: in vitro antifungal potential of imidazolylchalcone derivatives against R. solani Compounds Regression equation χ 2 ED 50 (μg mL -1 ) Fiducial limit IC-1 0.714X +- 1.714 2.31 410.3 h 208.3-1867.47 IC-2 1.143X +- 2.543 0.72 176.08 gh 124.86-301.5 IC-3 0.5X +- 0.5 0.17 8.48 b-e 0.35-19.64 IC-4 0.714X +- 0.714 0.007 8.81 b-e 2.80-15.44 IC-5 1.0X +- 1.8 0.15 14.84 b-e 8.39-21.22 IC-6 1.0X +- 1.8 9.56 32.71 d-f 1.17-86.56 IC-7 0.714X +- 0.514 0.27 4.35 ab 0.65-9.59 IC-8 0.571X +- 0.229 0.19 0.69 a 0.005-3.06 IC-9 0.429X +- 0.529 0.27 15.13 b-f 2.26-29.02 IC-10 0.5X +- 0.1 0.78 2.28 a-c 0.035-7.44 IC-11 0.714X +- 0.514 0.28 6.75 a-d 1.85-12.51 IC-12 1.0X +- 1.4 2.69 29.26 c-f 18.45-40.80 IC-13 0.357X +- 0.757 0.03 134.62 fg 63.53-3441.93 IC-14 0.571X +- 0.971 0.66 36.42 ef 19.31-57.81 IC-15 0.857X +- 1.257 2.34 22.66 b-f 13.37-32.01 *Hexaconazole 5% SC, ED 50 = 3.57 µg mL -1 *ED 50 values with different superscripts are significantly different (p<0.001). Table 4: in vitro antifungal potential of imidazolylchalcone derivatives against F. oxysporum . Compounds Regression equation χ 2 ED 50 (μg mL -1 ) Fiducial limit IC-1 0.86X +- 2.06 1.01 361.62 a-d 185.7-1664.54 IC-2 0.86X +- 2.46 0.34 1272.2 c-f 459.65-17661.6 IC-3 0.86X +- 1.86 0.79 135.76 ab 93.06-252.34 IC-4 0.86X +- 1.86 1.11 119.22 a 85.21-198.87 IC-5 0.86X +- 2.26 0.34 400.44 a-e 221.7-1298.64 IC-6 0.893X +- 2.643 0.73 1088.69 ef 461.57-7540.64 IC-7 0.86X +- 2.46 1.60 1122.79 d-f 452.49-9494.94 IC-8 0.86X +- 2.26 0.34 532.89 a-e 259.81-2618.13 IC-9 0.571X +- 1.771 0.16 1174.88 b-e 387.61-32677.63 IC-10 0.71X +- 1.91 0.29 535.24 a-e 255.58-2889.14 IC-11 0.71X +- 1.91 0.24 615.33 a-e 266.31-5112.63 IC-12 0.71X +- 1.71 0.23 319.15 a-c 169.51-1319.40 IC-13 1.071X +- 3.321 1.18 1674.03 ef 599.19-21776.24 IC-14 1.0X +- 3.2 1.36 1260.7 ef 517.01-9960.98 IC-15 1.286X +- 3.886 0.53 1052.59 f 494.08-5622.39 *Carbendazim 50% WP, ED 50 = 9.132 µg mL -1 *ED 50 values with different superscripts are significantly different (p<0.001). 3.3 Nematicidal activity The results of in vitro nematicidal activity of synthesized imidazolylchalcones against M. incognita (root knot nematode) are presented in Table 5 , which revealed that compound IC-6 (LC 50 = 33.62 μg mL -1 ) showed highest activity followed by IC-3 (LC 50 =34.75 μg mL -1 ), IC-5 (LC 50 =64.79 μg mL -1 ) and IC-12 (LC 50 =69.11 μg mL -1 ) after 24 hr observation as compared to positive control Velum Prime 34.48% SC (Fluopyrum; LC 50 = 3.46 μg mL -1 ). Table 5: Nematicidal activity of imidazolylchalcone derivatives against M. incognita : Compounds LC 50 (μg mL -1 ) 24 hr 48 hr 72 hr 96 hr IC-1 84.0 ab 77.15 e 70.49 f 66.43 d IC-2 87.76 ab 82.52 d 77.93 d 68.99 c IC-3 34.75 b 25.98 i 24.09 k 23.46 i IC-4 87.19 ab 83.55 d 72.60 e 59.65 e IC-5 64.79 ab 59.25 fg 53.93 g 47.53 g IC-6 33.62 b 24.27 i 21.29 l 19.49 j IC-7 90.13 ab 82.8 d 72.45 e 58.32 e IC-8 133.22 a 122.9 b 96.11 b 77.65 b IC-9 141.63 a 114.64 c 92.50 c 75.27 b IC-10 195.84 ab 128.47 a 104.98 a 81.88 a IC-11 84.95 b 60.79 f 43.55 h 32.06 h IC-12 69.11 b 50.10 h 38.14 j 30.50 h IC-13 78.05 b 55.85 g 41.08 i 29.74 h IC-14 85.77 b 56.99 g 40.49 i 29.55 h IC-15 172.89 ab 123.69 b 77.92 d 53.87 f *Fluopyram (Velum) LC 50 : 3.46 (24 hr), 1.99 (48 hr), 0.14 (72 hr), 0.05 (96 hr) µg mL -1 *LC 50 values with different superscripts are significantly different (p<0.001). 3.4 Molecular docking: Molecular docking is a computational technique that enables virtual exploration of the interactions between proteins and molecules. This method plays a crucial role in the rational design, optimization, and characterization of protein-ligand interactions, contributing to the development of novel agrochemicals. In this study, molecular docking was employed to investigate the binding interactions of selected compounds with key target sites in two pathogenic fungi, Sclerotium rolfsii and Fusarium oxysporum , as well as in the nematode Meloidogyne incognita . The study focused on two primary fungal targets: cutinase and elongation factor. Cutinases, hydrolytic enzymes found in fungal cell walls, catalyze the breakdown of glycosidic bonds in chitin. These enzymes play a pivotal role in facilitating fungal penetration into plant root tissues, enabling pathogens like F. oxysporum to establish primary infections. Due to its critical role in the pathogenic mechanism of F. oxysporum , cutinase represents an attractive target for antifungal intervention, potentially disrupting the fungus’s ability to cause disease. Similarly, elongation factors, essential for fungal growth and survival, present another prime target for the development of fungicidal compounds (Taruna et al., 2023; Dimarogona et al., 2015; Godara et al., 2024). Additionally, acetylcholinesterase, a vital enzyme for the regulation of nerve signal transmission, was explored as a target in M. incognita . This enzyme's crucial role in maintaining steady nerve signal transfer makes it an important target for pest control strategies against nematodes (Yadav et al., 2024; Mondal et al., 2024). These docking studies provide valuable insights into the molecular interactions at these target sites, facilitating the design of effective antifungal and nematicidal agents. The compound under study showed promising interactions with their respective target enzymes, as summarized in Table 6 . IC -4 , the compound showing the best activity against F . oxysporum , strongly inhibited the activity of cutinase enzyme through conventional H bonding, C-H hydrogen bonding and π-Cation interactions involving the residues like ARG 102, ASN 427 and GLN 424; which was further stabilized by hydrophobic interaction such as π-Alkyl interactions involving ARG 425, ARG 380 and ARG 276. The compound IC -8 was found to inhibit both the elongation factor and cutinase of R . soalni strongly, however, the binding with elongation factor was stronger (ΔG = -9.7 kcal/mol) as compared to cutinase (ΔG = -8.3 kcal/mol). This bonding was again attributed towards the conventional hydrogen bond and π-Anion bond, further strengthened by hydrophobic interactions such as π-Alkyl, π-σ, and π-π T shaped interactions. Similarly, the compound IC -6 was found to bind favorably with acetylcholinesterase of M . incognita . Conventional hydrogen bond involving SER 252 and HIS 514, along with some hydrophobic interactions such as π-π stacked, π-σ, and π-π T shaped interactions, helped in the binding process. Some discrepancies were observed between the molecular docking results and the outcomes of the in vitro experiments. Notably, while the compound IC -4 demonstrated the most potent fungicidal activity against Fusarium oxysporum in vitro , the in silico studies ranked it below compound IC -8 , which exhibited the highest binding affinity. This divergence can be attributed to the inherent complexities of biological systems in vitro , which involve numerous interacting components, dynamic signaling pathways, and environmental fluctuations that are not fully accounted for in computational models. Furthermore, in actual biological environments, additional binding sites on the target molecule may become accessible, leading to interactions that are not predicted by in silico docking analyses (Chen, 2015). ( Figure 4 ). Table 6: Binding energies of synthesized compounds against various target sites Compound Binding affinity (kcal/mol) Fusarium oxysporum Rhizoctonia solani Meloidogyne incognita Cutinase Elongation factor Cutinase Elongation factor Acetylcholinesterase IC-1 -8.3 -6.9 -7.5 -9.0 -9.7 IC-2 -8.0 -6.8 -7.8 -9.0 -9.5 IC-3 -8.3 -6.7 -7.2 -9.1 -8.8 IC-4 -8.1 -6.9 -7.4 -9.2 -9.5 IC-5 -8.7 -7.4 -7.6 -9.1 -9.6 IC-6 -8.7 -7.3 -7.8 -9.4 -9.7 IC-7 -8.6 -6.9 -7.7 -9.2 -8.9 IC-8 -9.3 -6.5 -8.3 -9.7 -9.7 IC-9 -8.1 -6.5 -7.4 -9.0 -8.6 IC-10 -8.2 -6.9 -7.6 -8.8 -9.5 IC-11 -8.5 -7.1 -7.9 -9.3 -9.5 IC-12 -8.0 -7.1 -7.5 -9.2 -9.6 IC-13 -8.3 -6.9 -7.5 -9.0 -9.4 IC-14 -7.9 -6.9 -7.6 -8.9 -9.3 IC-15 -8.2 -6.4 -7.1 -8.2 -8.7 4. Conclusion To the best of our knowledge this is the first attempt to synthesize a series of imidazolylchalcone derivatives through ultrasonication method, which is considered as green synthesis and gave higher yield with lesser reaction time as compared to conventional method. The synthesized compounds were characterized by spectroscopic techniques and their efficacy was evaluated against soil borne fungi ( R. solani and F. oxysporum ) and nematicidal activity against M. incognita . Bio efficacy results revealed that compound ((E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(4-benzyloxy)phenyl)prop-2-en-1-one) ( IC-8 ; ED 50 = 0.69 µg mL - 1 ) was found to be most active against R. solani , which was better than commercial hexaconazole 5% SC (ED 50 = 3.75 µg mL - 1 ). Whereas, in case F. oxysporum , compound (E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(2-bromophenyl) prop-2-en-1-one ( IC-4 ; ED 50 = 119.22 µg mL - 1 ) showed highest activity as compared with Carbendazim 50% WP (ED 50 = 9.01 µg mL - 1 ). In nematicidal bioassay, compound (E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(3-nitrophenyl) prop-2-en-1-one ( IC-6 ; LC 50 = 33.62 µg mL - 1 ) was most active against M. incognita (root-knot nematode after 24 h of inoculation as compared with commercial compound Velum Prime (LC 50 = 3.46 µg mL - 1 ). However, the nematicidal activity shown by imidazolylchalcone derivatives was lower than the commercial one. Furthermore, molecular docking investigations supported the findings of biological assessments, identifying IC-8 as the most effective compound against R. solani with highest binding energy (-8.5 kcal mol - 1 ), IC-4 (-8.0 kcal mol - 1 ) against cutinase enzyme of F. oxysporium and IC-6 (-9.7 kcal mol - 1 ) against acetylcholinesterase enzyme of M. incognita . These compounds could serve as lead compounds for the development of potent molecules intended for use as pest control agents. Declarations Ethics Approval and Consent to participate: Not applicable Consent for publication: All authors give consent for the publication of the manuscript in the Journal of BMC Chemistry Availability of data and materials: The data generated and/or analyzed during the current study are not publicly available due feasibility of the study to begin a further in-vivo trial; however, they are available from the corresponding author upon reasonable request. Competing interests: The authors declare that they have no competing interests. Funding: Financial support received from PI Industries Ltd. And CII, New Delhi as Prime Minister’s Fellowship and other facility support from ICAR- Indian Agricultural Research Institute, New Delhi-110012. Authors' contributions: RK: Design of the work, acquisition, analysis, interpretation of data and drafted work, KPT: Analysis, interpretation of data, PK: Design of the work, substantively revised, RG: Interpretation of data and drafted work, SRM: Analysis and draft revision, VK: Experimentation, draft revision, PCM: Analysis and interpretation of data, J: Experimentation and drafting, VSR: Design of the work, interpretation of data, P: Analysis, interpretation of data, VS: Interpretation of data, DK: Substantively revised draft. NAS: Conceptualize, supervision, design of the work, interpretation of data. Acknowledgment: The authors gratefully acknowledge ICAR-Indian Agricultural Research Institute for providing facilities to carry out the research work and thankful for the financial support received from PI Industries Ltd., CII, New Delhi and Prime Minister’s Fellowship for financial support. Supporting information includes chemical structure, 1 H-NMR, 13 C-NMR and HRMS spectra of most effective compounds IC-4, IC-6 and IC-8 with IC-1 as representative of imidazolylchalcone derivatives. References Abbott, W.S. A method of computing the effectiveness of an insecticide. J. Econ. Entomol ., 1925, 18(2), 265-267. Brevik, K., Schoville, S.D., Mota‐Sanchez, D. and Chen, Y.H. Pesticide durability and the evolution of resistance: A novel application of survival analysis. Pest Manag. Sci ., 2018, 74(8), 1953-1963. https://doi.org/10.1002/ps.4899 Chen, Y.C. Beware of docking!. Trends Pharmacol. Sci. , 2015, 36(2), 78-95. DeVito, S.C. On the design of safer chemicals: A path forward. 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Nene, Y. L.; Thapliyal, P. N. “Fungicides in plant disease control,” in Evaluation of fungicides . Editors Y. L. Nene and P. N. Thapliyal (New Delhi, India: Oxford and IBH Publishing Co.),1979, 406–428. Oraon, S., Padamini, R., Shahni, Y.S., Das, N., Sinha, D., Sujatha, G.S., Singh, O.B. and Karanwal, R., 2024. Impact of Emerging Pathogens in Crop Production. Microbiol. Res. J. Int. , 34(7), 80-92. Puri, S., Kaur, B., Parmar, A. and Kumar, H. Applications of ultrasound in organic synthesis-a green approach. Curr Org Chem. , 2013, 17(16), 1790-1828. Rani, N., Sharma, A., Kumar Gupta, G. and Singh, R. Imidazoles as potential antifungal agents: A review. Mini Rev Med Chem , 2013, 13(11), 1626-1655. Shakil, N.A., Singh, M.K., Kumar, J., Sathiyendiran, M., Kumar, G., Singh, M.K., Pandey, R.P., Pandey, A. and Parmar, V.S. Microwave synthesis and antifungal evaluations of some chalcones and their derived diaryl-cyclohexenones. J. Environ. Sci. Health B , 2010, 45(6), 524-530. https://doi.org/10.1080/03601234.2010.493482 Shakil, N.A., Singh, M.K., Sathiyendiran, M. and Kumar, J. Microwave accelerated solvent-free synthesis and antifungal evaluations of flavanones. Arch. Phytopathol. Pflanzenschutz. , 2011, 44(20), 1958-1965. https://doi.org/10.1080/03235408.2010.544467 Shakil, N.A., Singh, M.K., Sathiyendiran, M., Kumar, J. and Padaria, J.C. Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives. Eur. J. Med. Chem. , 2013, 59, 120-131. https://doi.org/10.1016/j.ejmech.2012.10.038 Singh, B.K., Singh, S.S.B.K. and Yadav, S.M. Some important plant pathogenic disease of brinjal ( Solanum melongena L.) and their management. Plant Pathol. J., 2014, 13(3), 208-213. Siwach, A. and Verma, P.K. Synthesis and therapeutic potential of imidazole containing compounds. BMC chem , 2021, 15, 1-69. Taruna, A., Dewi, R.R., Hadiwijoyo, E., Yulianah, I., Syib’li, M.A. and Abadi, A.L. Molecular Docking and In Vitro Study Revealed the Inhibition Mechanism of Cutinase of Fusarium oxsyporum f. sp lycopersici by Natural Compounds of Local Turmeric in Indonesia. AGRIVITA, J Agric Sci , 45(3), 2023, 554-569. Tolomeu, H.V. and Fraga, C.A.M. Imidazole: synthesis, functionalization and physicochemical properties of a privileged structure in medicinal chemistry. Molecules , 2023, 28(2), p.838. Tripathi, K., Kaushik, P., Yadav, D.K., Kumar, R., Misra, S.R., Godara, R., Bashyal, B.M., Rana, V.S., Kumar, R., Yadav, J. and Shakil, N.A. Synthesis, antifungal evaluation, two‐dimensional quantitative structure–activity relationship and molecular docking studies of isoxazole derivatives as potential fungicides. Pest Manag. Sci. 2024. https://doi.org/10.1002/ps.8152. Ul Haq, I., Sarwar, M.K., Faraz, A. and Latif, M.Z. Synthetic chemicals: Major component of plant disease management. Plant disease management strategies for sustainable agriculture through traditional and modern approaches , 2020, 53-81. Yadav, D.K., Kaushik, P., Pankaj, Rana, V.S., Kamil, D., Khatri, D. and Shakil, N.A. Microwave assisted synthesis, characterization and biological activities of ferrocenyl chalcones and their QSAR analysis. Front. Chem. , 2019, 7, 814. https://doi.org/10.3389/fchem.2019.00814 Yadav, D.K., Kaushik, P., Tripathi, K.P., Rana, V.S., Yeasin, M., Kamil, D., Pankaj, Khatri, D. and Shakil, N.A. Bioefficacy evaluation of ferrocenyl chalcones against Meloidogyne incognita and Sclerotium rolfsii infestation in tomato. J. Environ. Sci. Health B. , 2022, 57(3), 192-200. https://doi.org/10.1080/03601234.2022.2042154 Yadav, D.K., Tripathi, K.P., Pankaj, P., Kaushik, P., Rana, V.S., Khatri, D. and Shakil, N.A. Antinemic activity of ferrocenyl chalcones against Meloidogyne incognita infestation in tomato. Indian J. Agric. Sci. , 2021, 91(2), 305-9. https://doi.org/ 10.56093/ijas.v91i2.111644 Yadav, N., Kumar, R., Sangwan, S., Dhanda, V., Rani, R., Devi, S., Duhan, A., Sindhu, J., Chauhan, S., Malik, V.K. and Yadav, S. Design, synthesis, nematicidal evaluation, and molecular docking study of pyrano [3, 2-c] pyridones against Meloidogyne incognita . J. Agric. Food Chem. , 2024, 72(28), 15512-15522. Scheme Scheme 1 is available in the Supplementary Files section. Additional Declarations No competing interests reported. Supplementary Files SupplementaryfileIC1spectra.docx scheme1.png Scheme I- General method for the synthesis of Imidazolylchalcones Cite Share Download PDF Status: Published Journal Publication published 29 Apr, 2025 Read the published version in BMC Chemistry → Version 1 posted Editorial decision: Revision requested 15 Jan, 2025 Editor assigned by journal 14 Jan, 2025 Submission checks completed at journal 14 Jan, 2025 First submitted to journal 10 Jan, 2025 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. 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09:42:22","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":392778,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eFungicidal activity of potent molecules, IC-8 and IC-10 against \u003c/strong\u003e\u003cem\u003e\u003cstrong\u003eR. solani\u003c/strong\u003e\u003c/em\u003e\u003cstrong\u003e.\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-5803429/v1/922f477d66c60bcb71d3c25a.png"},{"id":73851588,"identity":"07b1b4e3-e227-4be7-bad5-35ada7a1571a","added_by":"auto","created_at":"2025-01-15 09:42:22","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":358450,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eFungicidal activity of IC-3 and IC-4 against \u003c/strong\u003e\u003cem\u003e\u003cstrong\u003eF. oxysporum\u003c/strong\u003e\u003c/em\u003e\u003cstrong\u003e.\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-5803429/v1/3b0988fe60f9ffce9f7e500e.png"},{"id":73853127,"identity":"c08a9d30-361e-4383-8cf8-a431b9aca8f7","added_by":"auto","created_at":"2025-01-15 09:58:22","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":294713,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003e2D interaction (A) and protein ligand binding (B) of IC-4, IC-8, and IC-6 with their respective target sites of \u003c/strong\u003e\u003cem\u003e\u003cstrong\u003eF\u003c/strong\u003e\u003c/em\u003e\u003cstrong\u003e. \u003c/strong\u003e\u003cem\u003e\u003cstrong\u003eoxysporum\u003c/strong\u003e\u003c/em\u003e\u003cstrong\u003e, \u003c/strong\u003e\u003cem\u003e\u003cstrong\u003eR\u003c/strong\u003e\u003c/em\u003e\u003cstrong\u003e. \u003c/strong\u003e\u003cem\u003e\u003cstrong\u003esolani\u003c/strong\u003e\u003c/em\u003e\u003cstrong\u003e, and \u003c/strong\u003e\u003cem\u003e\u003cstrong\u003eM\u003c/strong\u003e\u003c/em\u003e\u003cstrong\u003e. \u003c/strong\u003e\u003cem\u003e\u003cstrong\u003eincognita\u003c/strong\u003e\u003c/em\u003e\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-5803429/v1/df12f5462a7d90579d94e4fb.png"},{"id":81988202,"identity":"0f1e24a4-a6cc-4833-880c-2f87e31175c8","added_by":"auto","created_at":"2025-05-05 16:08:17","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":3736457,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-5803429/v1/cbf3751d-828f-447a-a51b-488da288445a.pdf"},{"id":73851583,"identity":"f1abca34-7974-45d8-8f1e-f0c5aa618bcd","added_by":"auto","created_at":"2025-01-15 09:42:22","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":2002425,"visible":true,"origin":"","legend":"","description":"","filename":"SupplementaryfileIC1spectra.docx","url":"https://assets-eu.researchsquare.com/files/rs-5803429/v1/10ff1340e09d93acf6a26fcb.docx"},{"id":73851578,"identity":"5eac137b-1a70-4e86-bac7-5570e46d2470","added_by":"auto","created_at":"2025-01-15 09:42:22","extension":"png","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":28124,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme I- General method for the synthesis of Imidazolylchalcones\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"scheme1.png","url":"https://assets-eu.researchsquare.com/files/rs-5803429/v1/ee5e258b5ec3ea95d11b00ab.png"}],"financialInterests":"No competing interests reported.","formattedTitle":"Green Synthesis, Characterization, In Silico Molecular Docking and Biological Evaluation of Imidazolylchalcones as Promising Fungicide/s and Nematicide/s","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eIn modern agriculture, emerging diseases caused by fungi, bacteria, viruses, and nematodes pose a severe threat to global crop production, affecting yield and quality. Trade globalization and climate change have accelerated the spread of these infections, intensifying the challenge to food security and economic stability, especially in agriculture-dependent regions of world (Oraon et al., 2024). Pests and pathogens destroy 40\u0026ndash;50% of crop yields, with plant diseases responsible for about a quarter of these losses (Khan et al., 2021) and plant parasitic nematodes cause an estimated 12.3% annual yield loss in global food production, valued at $157 billion (Hassan et al., 2013). The most devastating vegetable diseases include root rot, damping-off, charcoal rot, and wilt, are caused by pathogens like \u003cem\u003eRhizoctonia solani\u003c/em\u003e, \u003cem\u003eAlternaria solani\u003c/em\u003e, \u003cem\u003eFusarium oxysporum\u003c/em\u003e, \u003cem\u003eSclerotium rolfsii\u003c/em\u003e, \u003cem\u003eMacrophomina phaseolina\u003c/em\u003e, and \u003cem\u003ePythium\u003c/em\u003e spp (El-Kazzaz et al., 2022). Among vegetables, \u003cem\u003eSolanum melongena\u0026nbsp;\u003c/em\u003e(brinjal) is highly vulnerable to pre- and post-emergence damping-off, root rot (\u003cem\u003eR. solani\u003c/em\u003e) and wilt (\u003cem\u003eF. oxysporum\u003c/em\u003e) of seedlings at nursery stage of crop. These soil-borne fungi cause severe plant mortality and significant crop losses, impacting food security and farmers\u0026apos; livelihoods (Singh et al., 2014). Similarly, \u003cem\u003eMeloidogyne incognita\u003c/em\u003e (Root-knot nematode), also causes severe damage to crop roots, disrupting nutrient uptake and reducing plant vigor, often leading to crop failure. In India, it is responsible for a 21% yield loss in brinjal (Gawade et al., 2022). While, over the past three decades, natural products from diverse microbial sources and botanicals have been explored for control of pests and diseases (Kumar et al., 2021). However, due to narrow spectrum, low stability and low efficacy are limitation for immediate control of pests. Therefore, the importance of synthetic agrochemicals such as fungicides, insecticides, antimicrobial agents, herbicides, nematicides, seed protectants, insect repellents and rodenticides cannot be overstated, especially considering that certain insect pests have developed resistance to specific chemicals (Brevik et al., 2018). Synthetic pesticides have\u0026nbsp;also\u0026nbsp;shown limitations, such as health risks, pesticide residues, environmental impact, and the emergence of resistant pathogens. Additionally, climate change has affected the efficacy of these chemicals (Ul Haq et al., 2020). To overcome resistance, there is a need to synthesize safe, broad spectrum, efficient, cost-effective and potential bioactive molecule/s to control pests and diseases (DeVito, 2016).\u003c/p\u003e\n\u003cp\u003eIn recent years, there has been growing interest in environment friendly synthesis of synthetic agrochemicals. The application of ultrasound irradiation as an alternative energy source or green organic synthesis has gained significant interest with a focus on multicomponent reactions at ambient reaction conditions, eco-friendly solvents and catalyst-free synthesis of bioactive heterocyclic scaffolds (Karmakar and Mukhopadhyay, 2021 and Puri et al., 2013). In the present study compounds were synthesized \u003cem\u003evia\u003c/em\u003e ultrasonication and compared with the conventional methodology for their yield and time. Chalcones, a class of naturally occurring flavonoids, have emerged as potent bioactive molecules with a wide range of biological activities, including antifungal, antiparasitic, antibacterial, insecticidal, nematicidal, antioxidant, antiplasmodial, antitumor, and anthelmintic activities (Shakil et al., 2010, 2011, 2013). The structural diversity of chalcones and their ease of modification make them attractive candidates for the development of new agrochemicals\u0026nbsp;(Yadav et al., 2019). Chalcones are \u0026alpha;,\u0026beta;-unsaturated ketones characterized by the presence of two aromatic rings connected by a three-carbon \u0026alpha;,\u0026beta;-unsaturated carbonyl system. This unique structure enables chalcones to exhibit various mechanisms of action, including enzyme inhibition, cell membrane disruption, and the generation of reactive oxygen species (Godara et al., 2024). Furthermore, the introduction of heterocyclic moieties into the chalcone framework has been shown to enhance their biological activity. Imidazole, a five-membered heterocycle containing two nitrogen atoms, is one such moiety that has attracted significant attention due to its presence in a wide range of biologically active compounds\u0026nbsp;(Siwach and Verma, 2021). Imidazole derivatives are known for their antibacterial, anti-inflammatory, antidiabetic, antiparasitic, antituberculosis, antifungal, antioxidant, antitumor, antimalarial, anticancer, antidepressant properties (Tolomeu and Fraga, 2023; Rani et al., 2013) making them ideal candidates for the development of new agrochemicals or therapeutic agents. In this context, imidazolylchalcones, a class of chalcones with an imidazole ring, can represent a promising avenue for the development of novel agrochemical. The introduction of the imidazole ring into the chalcone structure is expected to enhance the biological activity of the resulting compounds by improving their ability to interact with biological targets. In this study, we report an eco-friendly synthesis of imidazolylchalcone derivatives \u003cem\u003evia\u003c/em\u003e Claisen-Schmidt condensation\u0026nbsp;using ultrasonication and compared with conventional synthetic approach, followed by evaluation against plant pathogenic fungi, \u003cem\u003eF. oxysporum\u003c/em\u003e, \u003cem\u003eR. solani\u003c/em\u003e and root knot nematode, \u003cem\u003eM. incognita\u003c/em\u003e. \u0026nbsp; Simultaneously, we carried out a computational modelling or docking study by simulating the binding of imidazolylchalcones to key enzymes, such as fungal cutinase and nematode acetylcholinesterase (AChE) to predict/identify lead compounds with high binding affinity and potential for biological efficacy.\u0026nbsp;\u003c/p\u003e"},{"header":"2. Materials and Methods","content":"\u003cp\u003e\u003cstrong\u003e2.1 Chemicals and Instruments\u003cs\u003e\u0026nbsp;\u003c/s\u003e\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eBenzaldehydes,\u0026nbsp;4-(Imidazol-1-yl) acetophenone\u0026nbsp;were obtained from Sigma-Aldrich and used without further purification. Analytical grade solvents and chemicals were used. Thin layer chromatography (TLC) was used to monitor reactions on 200 mm thick aluminium sheets of Merck silica gel 60F\u003csub\u003e254\u003c/sub\u003e and spots were visualised under UV light. A Heidolf rotary evaporator was employed for solvent removal. \u003csup\u003e1\u003c/sup\u003eH-NMR and \u003csup\u003e13\u003c/sup\u003eC-NMR spectra were obtained on a JEOL 400 MHz Spectrospin spectrometer, with tetramethylsilane (TMS) serving as an internal standard for calibration. Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS) was performed using an AB SCIEX Triple TOFTM 5600+ apparatus with TurboIonSpray (TIS), SCIEX ExionLC, and a PDA detector. A C\u003csub\u003e18\u003c/sub\u003e column (2.7\u0026mu;m, 4.6x100 mm) was utilised for compound separation. The column was eluted with Methanol: Water (98:2% (v/v) containing 0.1% formic acid at a flow rate of 1.0 mL/min and a column oven temperature of 40 \u0026deg;C. Ultrasonic bath (Labman Scientific Instruments) was used for synthesis and cleaning of glasswares. Melting point was recorded in Buchi M-560 instrument and were uncorrected.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.2 Methods of Synthesis\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.2.1 Conventional synthesis of imidazolylchalcones (Single step reaction)\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe imidazolyl chalcone series was synthesized \u003cem\u003evia\u003c/em\u003e base-catalyzed Claisen-Schmidt reaction using the method described by Liu et al., (2013). Equimolar amounts of selected benzaldehydes were dissolved in 5 mL of 40% ethanolic NaOH solution in a round-bottomed flask and stirred at room temperature for 10 minutes. After that, 4-(Imidazol-1-yl) acetophenone (dissolved in 5 mL of ethanol) was added dropwise with continuously stirring on magnetic stirrer. The stirring duration ranged from 1 to 28 h for different reactions at room temperature, as shown in \u003cstrong\u003eScheme I\u003c/strong\u003e.\u0026nbsp;After the reaction was complete, the reaction mixture was neutralized with 2M HCl, resulting in the formation of a creamy white or light-yellow precipitate. This precipitate was separated by filtration and rinsed with cold water. In case of\u0026nbsp;\u0026nbsp;no precipitate formation, the\u0026nbsp;reaction mixture was extracted with ethyl acetate (30 mL \u0026times; 3). The organic layer was dehydrated using anhydrous Na\u003csub\u003e2\u003c/sub\u003eSO\u003csub\u003e4\u003c/sub\u003e and solvent was removed using a rotary evaporator, leaving behind a viscous residue.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.2.2 Ultrasonic synthesis of imidazolylchalcones (Single step reaction):\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eEquimolar amounts of 4 -(Imidazol-1-yl) acetophenone (100 mg, 0.537 mmol) in 40% ethanolic KOH (5 mL) was taken in 250 mL round bottom flask and ethanolic solution of the different benzaldehydes were added. RB flask was fixed with burette stand in ultrasonic bath at temp. 25-30 \u003csup\u003eo\u003c/sup\u003eC, frequency 40 KHz with time range, 5-90 min., depending on the compounds listed in \u003cstrong\u003eTable 1\u0026nbsp;\u003c/strong\u003eand the reactions were monitored by TLC in ethyl acetate: hexane (2:8) solvent systems. After completion of reaction, reaction mixture was worked up as described in conventional method. Crude product purified through column chromatography on silica gel, using a solvent mixture of hexane and ethyl acetate with increasing polarity. The desired compound was eluted with a solvent mixture containing 10% ethyl acetate and hexane.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 1: Different substituents of imidazolylchalcone derivatives\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd rowspan=\"2\" style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eCompounds\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" style=\"width: 265px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eX\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd height=\"41\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-1\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e2,6-Cl\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-2\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e4-F\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"27\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-3\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e4-Br\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-4\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e2-Br\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"27\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-5\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e2-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-6\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e3-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"27\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-7\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e4-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-8\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e4-OCH\u003csub\u003e2\u003c/sub\u003e-C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"27\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-9\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e4-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-10\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e3-Cl\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-11\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e2,4-Cl\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"27\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-12\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e2-Cl\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-13\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e3-OH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"27\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-14\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e4-OH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"28\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 219px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-15\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 265px;\"\u003e\n \u003cp\u003e3,4,5-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd height=\"27\" style=\"width: 0px;\"\u003e\u003cbr\u003e\u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u003cstrong\u003e2.3 Spectral analysis of imidazolylchalcone derivatives\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3.1\u003c/strong\u003e \u003cstrong\u003e(E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(2,6-dichlorophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-1)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eCreamy yellow solid; m.p.: 149-151\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.56 (Hexane: ethyl acetate, 1:4).\u003csup\u003e\u0026nbsp;1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.28 (d, J = 16.8 Hz, H-3), 8.02 \u0026ndash; 7.92 (3H, m, Ar-H\u0026rsquo;), 7.89 (1H, d, J = 16.8 Hz, H-2), 7.84 \u0026ndash; 7.63 (4H, m, Ar-H\u0026rdquo;), 7.37 \u0026ndash; 7.20 (2H, m, H-4\u0026rsquo;\u0026rdquo; \u0026amp;amp; H-5\u0026rsquo;\u0026rdquo;), 7.11 (1H, s, H-2\u0026rsquo;\u0026rdquo;). 13 C NMR (101 MHz, DMSO-D\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 198.01(C1), 143.54(C3), 140.76(C4\u0026rdquo;), 136.26(C1\u0026rdquo;), 135.07(C1\u0026rsquo;, C2\u0026rsquo;\u0026rdquo;), 131.90(C2\u0026rsquo;, C6\u0026rsquo;), 130.94(C2\u0026rdquo;, C3\u0026rdquo;, C5\u0026rdquo;, C6\u0026rdquo;), 130.45(C4\u0026rsquo;\u0026rdquo;), 128.22(C3\u0026rsquo;, C5\u0026rsquo;), 126.38(C4\u0026rsquo;), 120.20(C2), 118.29(C5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 343.0394; Observed 343.0399.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3.2 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-fluorophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-2)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eYellow-brown solid; m.p.: 144-145\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.55 (Hexane: ethyl acetate, 1:4).\u003csup\u003e\u0026nbsp;1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.35 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.7 Hz, H-3), 8.28 \u0026ndash; 8.09 (4H, m, Ar-H\u0026rdquo;), 7.94 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.7 Hz, H-2), 7.63 \u0026ndash; 7.40 (6H, m, Ar-H\u0026rsquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.16 (1H, s, H-2\u0026rsquo;\u0026rdquo;).\u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 189.70 (C-1), 162.15 (C-4\u0026rsquo;), 143.65 (C-3), 142.83 (C-4\u0026rdquo;), 137.49 (C-1\u0026rdquo;), 135.60 (C-2\u0026rsquo;\u0026rdquo;), 130.70 (C-2\u0026rsquo;, C-6\u0026rsquo;), 130.40 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;), 129.93 (C-1\u0026rsquo;), 129.48 (C-4\u0026rsquo;\u0026rdquo;), 121.30 (C-2), 118.20 (C-5\u0026rsquo;\u0026rdquo;), 115.40 (C-3\u0026rsquo;, C-5\u0026rsquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eFN\u003csub\u003e2\u003c/sub\u003eO [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 293.1084; Observed 293.1085.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3.3 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-bromophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-3)\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eWhite solid; m.p.: 161-162\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.57 (Hexane: ethyl acetate, 1:4).\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.02 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.7 Hz, H-3), 7.96 \u0026ndash; 7.77 (8H, m, Ar-H\u0026rsquo; \u0026amp;Ar-H\u0026rdquo;), 7.70 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.7 Hz, H-2), 7.66 \u0026ndash; 7.59 (2H, m, H-4\u0026rsquo;\u0026rdquo; \u0026amp; H-5\u0026rsquo;\u0026rdquo;), 7.13 (1H, s, H-2\u0026rsquo;\u0026rdquo;). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-D6) \u0026delta; 188.22 (C-1), 143.37 (C-3), 140.86 (C-4\u0026rdquo;), 136.32 (C-1\u0026rdquo;), 135.85 (C-2\u0026rsquo;\u0026rdquo;), 134.49 (C-1\u0026rsquo;), 132.42 (C-3\u0026rsquo;), 132.42 (C-5\u0026rsquo;), 131.45 (C-2\u0026rdquo;), 131.45 (C-6\u0026rdquo;), 131.13 (C-3\u0026rdquo;), 131.13 (C-5\u0026rdquo;), 130.95 (C-4\u0026rsquo;\u0026rdquo;), 128.52 (C-2\u0026rsquo;), 128.52 (C-6\u0026rsquo;), 123.08 (C-4\u0026rsquo;), 120.31 (C-2), 118.35 (C-5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eBrN\u003csub\u003e2\u003c/sub\u003eO [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 353.0311; Observed 353.0284.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3.4 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(2-bromophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-4)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eCream yellow solid; m.p.: 121-123\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.70 (Hexane: ethyl acetate, 1:4). \u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.29 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.9 Hz, H-3), 8.24 \u0026ndash; 8.01 (4H, m, Ar-H\u0026rdquo;), 7.89 (4H, d, \u003cem\u003eJ\u003c/em\u003e = 16.9 Hz, H-2), 7.86 \u0026ndash; 7.67 (4H, m, Ar-H\u0026rsquo;), 7.56 \u0026ndash; 7.24 (2H, m, H-4\u0026rsquo;\u0026rdquo; \u0026amp; H-5\u0026rsquo;\u0026rdquo;), 7.13 (1H, s, H-2\u0026rsquo;\u0026rdquo;). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 188.12 (C-1), 141.95 (C-3), 140.98 (C-4\u0026rdquo;), 136.34 (C-1\u0026rdquo;), 135.65 (C-2\u0026rsquo;\u0026rdquo;), 133.85 (C-1\u0026rsquo;), 132.82 (C-3\u0026rsquo;), 131.23 (C-2\u0026rdquo;, C-6\u0026rdquo;), 130.98 (C-3\u0026rdquo;, C-5\u0026rdquo;), 129.42 (C-4\u0026rsquo;\u0026rdquo;), 128.77 (C-6\u0026rsquo;), 126.03 (C-5\u0026rsquo;), 125.16 (C-4\u0026rsquo;), 120.32 (C-2\u0026rsquo;), 120.15 (C-2), 118.33 (C-5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eBrN\u003csub\u003e2\u003c/sub\u003eO [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 353.0311; Observed 353.0284.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3\u003c/strong\u003e\u003cstrong\u003e.5 (E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(2-nitrophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-5)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eBlack solid; m.p.: 118-120\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.56 (Hexane: ethyl acetate, 1:4). \u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.45 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.4 Hz, H-3), 8.42 \u0026ndash; 8.34 (4H, m, Ar-H\u0026rdquo;), 8.18 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.4 Hz, H-2), 8.12 \u0026ndash; 7.67 (6H, m, Ar-H\u0026rsquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.12 (1H, s, H-2\u0026rsquo;\u0026rdquo;). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 203.51 (C-1), 147.95 (C-2\u0026rsquo;), 145.67 (C-3), 143.48 (C-4\u0026rdquo;), 137.87 (C-1\u0026rdquo;), 136.12 (C-2\u0026rsquo;\u0026rdquo;), 134.70 (C-5\u0026rsquo;), 131.74 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;), 130.65 (C-4\u0026rsquo;\u0026rdquo;), 129.19 (C-4\u0026rsquo;), 128.37 (C-1\u0026rsquo;), 126.87 (C-6\u0026rsquo;), 123.96 (C-3\u0026rsquo;), 120.85 (C-2), 118.39 (C-5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 320.1027; Observed 320.1030.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3\u003c/strong\u003e\u003cstrong\u003e.6 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(3-nitrophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-6)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003ePale-yellow solid; m.p.: 141-143\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.54 (Hexane: ethyl acetate, 1:4). \u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.44 (1H, s, H-2\u0026rsquo;), 8.26 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.5 Hz, H-3), 7.95 \u0026ndash; 7.85 (3H, m, H-4\u0026rsquo;, H-5\u0026rsquo;, H-6\u0026rsquo;), 7.84 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.5 Hz, H-2), 7.35 \u0026ndash; 7.16 (6H, m, Ar-H\u0026rdquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.13 (1H, s, H-2\u0026rsquo;\u0026rdquo;). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 197.74 (C-1), 148.22 (C-3\u0026rsquo;), 142.58 (C-4\u0026rdquo;), 140.84 (C-3), 136.26 (C-1\u0026rsquo;), 136.26 (C-1\u0026rdquo;), 135.52 (C-2\u0026rsquo;\u0026rdquo;), 134.97 (C-6\u0026rsquo;), 130.94 (C-2\u0026rdquo;), 130.94 (C-6\u0026rdquo;), 130.47 (C-3\u0026rdquo;), 130.47 (C-5\u0026rdquo;), 130.47 (C-4\u0026rsquo;\u0026rdquo;), 128.16 (C-5\u0026rsquo;), 123.12 (C-4\u0026rsquo;), 120.19 (C-2\u0026rsquo;), 120.19 (C-2), 118.28 (C-5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 320.1027; Observed 320.1030.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3\u003c/strong\u003e\u003cstrong\u003e.7 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-nitrophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-7)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eLight brown solid; m.p.: 165-167\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.59 (Hexane: ethyl acetate, 1:4). \u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.25 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.4 Hz, H-3), 8.15 \u0026ndash; 8.00 (4H, m, Ar-H\u0026rsquo;), 7.91 \u0026ndash; 7.77 (4H, m, Ar-H\u0026rdquo;), 7.64 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.4 Hz, H-2), 7.57 \u0026ndash; 7.41 (2H, m, H-4\u0026rsquo;\u0026rdquo; \u0026amp; H-5\u0026rsquo;\u0026rdquo;), 7.16 (1H, s, H-2\u0026rsquo;\u0026rdquo;).\u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 201.17 (C-1), 151.76 (C-4\u0026rsquo;), 147.01 (C-3), 143.84 (C-4\u0026rdquo;), 142.11 (C-1\u0026rsquo;), 136.03 (C-1\u0026rdquo;), 134.89 (C-2\u0026rsquo;\u0026rdquo;), 131.25 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;), 130.43 (C-4\u0026rsquo;\u0026rdquo;), 128.16 (C-2\u0026rsquo;, C-6\u0026rsquo;), 123.83 (C-3\u0026rsquo;, C-5\u0026rsquo;), 120.89 (C-2), 118.89 (C-5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 320.1027; Observed 320.1030.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3.\u003c/strong\u003e\u003cstrong\u003e8 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-8)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eCream white solid; m.p.: 153-155\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.70 (Hexane: ethyl acetate, 1:4).\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.25 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.9 Hz, H-3), 7.91 \u0026ndash; 7.81 (4H, m, Ar-H\u0026rdquo;), 7.47 \u0026ndash; 7.39 (2H, m, H-4\u0026rsquo;\u0026rdquo; \u0026amp; H-5\u0026rsquo;\u0026rdquo;), 7.39 \u0026ndash; 7.25 (9H, m, Ar-H\u0026rsquo; \u0026amp; Ar-Ha\u0026rsquo;), 7.13 (1H, s, H-2\u0026rsquo;\u0026rdquo;), 7.07 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.9 Hz, H-2), 5.15 (2H, s, -OCH\u003csub\u003e2\u003c/sub\u003e). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 188.14 (C-1), 161.04 (C-4\u0026rsquo;), 144.71 (C-3), 140.64 (C-4\u0026rdquo;), 137.20 (C-1\u0026rdquo;), 136.30 (C-1\u0026rsquo;a), 136.26 (C-2\u0026rsquo;\u0026rdquo;), 131.48 (C-2\u0026rdquo;, C-6\u0026rdquo;), 130.93 (C-3\u0026rdquo;, C-5\u0026rdquo;), 129.02 (C-2\u0026rsquo;, C-6\u0026rsquo;), 128.51 (C-4\u0026rsquo;\u0026rdquo;), 128.35 (C-3\u0026rsquo;a, C-5\u0026rsquo;a), 128.03 (C-4\u0026rsquo;a, C-1\u0026rsquo;), 127.25 (C-2\u0026rsquo;a, C-6\u0026rsquo;a), 120.28 (C-2), 118.34 (C-5\u0026rsquo;\u0026rdquo;), 115.76 (C-3\u0026rsquo;,C-5\u0026rsquo;), 69.92 (OCH\u003csub\u003e2\u003c/sub\u003e). HRMS for C\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 381.1462; Observed 381.1468.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3.9 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-methoxyphenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-9)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eCream white solid; m.p.: 146-147\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.57 (Hexane: ethyl acetate, 1:4). \u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.26 (1H, d, J = 16.4 Hz, H-3), 7.97 \u0026ndash; 7.62 (10H, m, Ar-H\u0026rsquo;, Ar-H\u0026rdquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.13 (1H, s, H-2\u0026rsquo;\u0026rdquo;), 6.98 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.4 Hz, H-2), 3.78 (3H, s, OCH\u003csub\u003e3\u003c/sub\u003e). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 188.15 (C-1), 161.97 (C-4\u0026rsquo;), 144.78 (C-3), 140.63 (C-4\u0026rdquo;), 136.27 (C-1\u0026rdquo;), 135.12 (C-2\u0026rsquo;\u0026rdquo;), 131.49 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;), 130.92 (C-2\u0026rsquo;, C-6\u0026rsquo;, C-4\u0026rsquo;\u0026rdquo;), 127.83 (C-1\u0026rsquo;), 120.28 (C-2), 118.34 (C-5\u0026rsquo;\u0026rdquo;), 114.94 (C-3\u0026rsquo;, C-5\u0026rsquo;), 55.93 (-OCH\u003csub\u003e3\u003c/sub\u003e). HRMS for C\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 305.1314; Observed 305.1318.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3\u003c/strong\u003e\u003cstrong\u003e.10 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(3-chlorophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-10)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003ePale-yellow solid; m.p.: 142-143\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.56 (Hexane: ethyl acetate, 1:4).\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.26 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.9 Hz, H-3), 7.94 \u0026ndash; 7.86 (4H, m, Ar-H\u0026rdquo;), 7.83 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.9 Hz, H-2), 7.33 \u0026ndash; 7.17 (6H, m, Ar-H\u0026rsquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.13 (1H, s, H-2\u0026rsquo;\u0026rdquo;). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 188.14 (C-1), 145.87 (C-3), 140.98 (C-4\u0026rdquo;), 139.19 (C-1\u0026rdquo;), 136.34 (C-1\u0026rsquo;), 135.65 (C-2\u0026rsquo;\u0026rdquo;), 134.98 (C-3\u0026rsquo;), 132.66 (C-2\u0026rdquo;, C-6\u0026rdquo;), 131.23 (C-3\u0026rdquo;, C-5\u0026rdquo;), 130.97 (C-4\u0026rsquo;\u0026rdquo;), 130.58 (C-5\u0026rsquo;), 129.25 (C-4\u0026rsquo;), 128.24 (C-6\u0026rsquo;), 125.02 (C-2\u0026rsquo;), 120.33 (C-2), 118.34 (C-5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eO [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 309.0784; Observed 309.0789.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3.11 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(2,4-dichlorophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-11)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eBrown solid; m.p.: 125-126\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.55 (Hexane: ethyl acetate, 1:4). \u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.03 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.2 Hz, H-3), 7.86 (1H, s, H-3\u0026rsquo;), 7.80 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.2 Hz, H-2), 7.75 \u0026ndash; 7.65 (6H, m, Ar-H\u0026rdquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.52 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 2.1 Hz, H-5\u0026rsquo;), 7.50 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 2.1 Hz, H-6\u0026rsquo;), 7.11 (1H, s, H-2\u0026rsquo;\u0026rdquo;). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 197.36 (C-1), 140.75 (C-3), 137.60 (C-4\u0026rdquo;), 136.78 (C-1\u0026rdquo;), 136.26 (C-2\u0026rsquo;), 135.30 (C-2\u0026rsquo;\u0026rdquo;), 131.60 (C-1\u0026rsquo;), 130.64 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;), 130.58 (C-6\u0026rsquo;, C-4\u0026rsquo;\u0026rdquo;), 128.13 (C-3\u0026rsquo;), 126.58 (C-5\u0026rsquo;), 125.38 (C-4\u0026rsquo;), 120.19 (C-2), 118.30 (C-5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 344.0232; Observed 344.0238.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3\u003c/strong\u003e\u003cstrong\u003e.12 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(2-chlorophenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-12)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003ePale-yellow solid; m.p.: 114-116\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.54 (Hexane: ethyl acetate, 1:4).\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.29 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.4 Hz, H-3), 8.10 \u0026ndash; 8.01 (4H, m, Ar-H\u0026rdquo;), 7.87 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.4 Hz, H-2), 7.58 \u0026ndash; 7.50 (2H, m, H-4\u0026rsquo;\u0026rdquo; \u0026amp; H-5\u0026rsquo;\u0026rdquo;), 7.49 \u0026ndash; 7.37 (4H, m, Ar-H\u0026rsquo;), 7.13 (1H, s, H-2\u0026rsquo;\u0026rdquo;). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 188.14 (C-1), 140.98 (C-3), 139.19 (C-4\u0026rdquo;), 136.34 (C-1\u0026rdquo;), 135.65 (C-2\u0026rsquo;\u0026rdquo;), 134.97 (C-2\u0026rsquo;), 132.66 (C-1\u0026rsquo;), 131.23 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;), 130.97 (C-4\u0026rsquo;\u0026rdquo;), 130.58 (C-3\u0026rsquo;), 129.25 (C-4\u0026rsquo;), 128.24 (C-6\u0026rsquo;), 125.02 (C-5\u0026rsquo;), 120.33 (C-2), 118.34 (C-5\u0026rsquo;\u0026rdquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eO [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 309.0784; Observed 309.0789.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3\u003c/strong\u003e\u003cstrong\u003e.13 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-13)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eCream white solid; m.p.: 232-234\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.57 (Hexane: ethyl acetate, 1:4).\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.26 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.8 Hz, H-3), 7.96 \u0026ndash; 7.87 (4H, m, Ar-H\u0026rdquo;), 7.84 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.8 Hz, H-2), 7.37 \u0026ndash; 7.15 (5H, m, H-4\u0026rsquo;, H-5\u0026rsquo;, H-6\u0026rsquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.13 (1H, s, H-2\u0026rsquo;\u0026rdquo;), 6.86 (1H, s, H-2\u0026rsquo;), 5.41(1H, s, -OH). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 188.37 (C-1), 158.40 (C-3\u0026rsquo;), 145.07 (C-3), 140.75 (C-4\u0026rdquo;), 136.44 (C-1\u0026rdquo;), 136.31 (C-1\u0026rsquo;), 136.03 (C-2\u0026rsquo;\u0026rdquo;), 131.05 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;), 130.93 (C-5\u0026rsquo;), 130.41 (C-4\u0026rsquo;\u0026rdquo;), 122.15 (C-2), 120.32 (C-6\u0026rsquo;), 118.48 (C-5\u0026rsquo;\u0026rdquo;), 118.34 (C-2\u0026rsquo;), 115.95 (C-4\u0026rsquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 291.0632; Observed 291.0628.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3\u003c/strong\u003e\u003cstrong\u003e.14 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-14)\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eCream yellow solid; m.p.: 247-249\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.55 (Hexane: ethyl acetate, 1:4).\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.34 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.8 Hz, H-3), 8.18 \u0026ndash; 7.98 (4H, m, Ar-H\u0026rdquo;), 7.98 \u0026ndash; 7.77 (6H, m, Ar-H\u0026rsquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.73 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 15.8 Hz, H-2), 7.16 (1H, s, H-2\u0026rsquo;\u0026rdquo;), 5.57(1H, s, -OH). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 197.62 (C-1), 157.58 (C-4\u0026rsquo;), 144.76 (C-3), 138.79 (C-4\u0026rdquo;), 137.40 (C-1\u0026rdquo;), 135.38 (C-2\u0026rsquo;\u0026rdquo;), 130.51 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;, C-2\u0026rsquo;, C-6\u0026rsquo;), 130.01 (C-4\u0026rsquo;\u0026rdquo;), 127.42 (C-1\u0026rsquo;), 122.28 (C-2) 118.47 (C-5\u0026rsquo;\u0026rdquo;), 115.80 (C-3\u0026rsquo;, C-5\u0026rsquo;). HRMS for C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 291.0632; Observed 291.0628.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3\u003c/strong\u003e\u003cstrong\u003e.15 (E)-1-(4-(1H-imidazole-1-yl) phenyl)-3-(3,4,5-trimethoxyphenyl) prop-2-en-1-one\u003c/strong\u003e \u003cstrong\u003e(IC-15)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eYellow brown solid; m.p.: 135-137\u003csup\u003eo\u003c/sup\u003eC, R\u003csub\u003ef\u003c/sub\u003e: 0.56 (Hexane: ethyl acetate, 1:4).\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 8.28 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.8 Hz, H-3), 7.88 (1H, d, \u003cem\u003eJ\u003c/em\u003e = 16.8 Hz, H-2), 7.78 \u0026ndash; 7.35 (6H, m, Ar-H\u0026rdquo; \u0026amp; H-4\u0026rsquo;\u0026rdquo;, H-5\u0026rsquo;\u0026rdquo;), 7.23 (2H, s, H-2\u0026rsquo; \u0026amp; H-6\u0026rsquo;), 7.14 (1H, s, H-2\u0026rsquo;\u0026rdquo;), 3.83 (9H, s, -OCH\u003csub\u003e3\u003c/sub\u003e). \u003csup\u003e13\u003c/sup\u003eC NMR (101 MHz, DMSO-\u003cem\u003eD\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u0026delta; 188.33 (C-1), 153.63 (C-3\u0026rsquo;, C-5\u0026rsquo;), 145.31 (C-3), 140.74 (C-4\u0026rdquo;), 140.31 (C-4\u0026rsquo;), 136.33 (C-1\u0026rdquo;), 136.02 (C-2\u0026rsquo;\u0026rdquo;), 131.06 (C-2\u0026rdquo;, C-3\u0026rdquo;, C-5\u0026rdquo;, C-6\u0026rdquo;), 130.95 (C-4\u0026rsquo;\u0026rdquo;), 127.51 (C-1\u0026rsquo;), 120.32 (C-2), 118.36 (C-5\u0026rsquo;\u0026rdquo;), 107.16 (C-2\u0026rsquo;, C-6\u0026rsquo;), 60.68 (4\u0026rsquo;-OCH\u003csub\u003e3\u003c/sub\u003e), 56.66 (3\u0026rsquo;-OCH\u003csub\u003e3\u003c/sub\u003e\u0026amp; 5\u0026rsquo;-OCH\u003csub\u003e3\u003c/sub\u003e). HRMS for C\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e [M+H]\u003csup\u003e+\u003c/sup\u003e\u003cem\u003em/z\u003c/em\u003e: Calcd 365.0839; Observed 365.0842.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.4 Antifungal bioassay:\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eImidazolylchalcone derivatives were assessed for their \u0026nbsp; antifungal properties \u003cem\u003ein vitro\u003c/em\u003e\u003cem\u003e\u0026nbsp;\u003c/em\u003eagainst \u003cem\u003eR. solani\u003c/em\u003e and \u003cem\u003eF. oxysporum\u003c/em\u003e using the poisoned food technique (Nene and Thapliyal, 1979). The fungal strains, \u003cem\u003eF. oxysporum\u003c/em\u003e ITCC 8113 and \u003cem\u003eR. solani\u003c/em\u003e ITCC 7479 were obtained from ITCC (Indian Type Culture Collection), Division of Plant Pathology, ICAR-IARI, New Delhi, India. These cultures were kept at 27\u0026deg;C for 4-7 days on PDA (Potato Dextrose Agar) slants and were regularly subcultured to maintain their viability and purity.\u003c/p\u003e\n\u003cp\u003eThe stock solution of synthesized compounds (1000 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) \u0026nbsp;was prepared in DMSO. An \u003cem\u003ein vitro\u003c/em\u003e bioassay was carried out at five different concentrations namely 200, 100, 50, 25 and 12.5\u0026nbsp;\u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e using freshly prepared PDA media in quadruplicate.\u0026nbsp;Positive controls for \u003cem\u003eF. oxysporum\u0026nbsp;\u003c/em\u003eand \u003cem\u003eR. solani\u003c/em\u003e were carbendazim 50% WP (Wettable Powder) and Hexaconazole 5% SC (Soluble Concentrate), respectively.\u0026nbsp;Fungal spores and mycelium were taken from subcultured fungal cultures using a 5-mm-thick disc, which was then inoculated in Petri dishes under laminar flow (sterile conditions). The treatment and control Petri dishes were placed in a BOD incubator at 25\u0026plusmn;1\u0026deg;C. Incubation\u0026nbsp;was\u0026nbsp;continued until the fungal growth completely covered or reached an advanced stage in the control Petri dish, which usually took about 4-5 days for \u003cem\u003eR. solani\u003c/em\u003e and 10-12 days for \u003cem\u003eF. oxysporum\u003c/em\u003e (Kaushik et al., 2021). Percentage inhibition was calculated by measuring colony diameter of fungi (Abbott, 1925).\u003c/p\u003e\n\u003cp\u003eI = {(C - T)/C} \u0026times; 100\u003c/p\u003e\n\u003cp\u003eWhere, I represent inhibition percentage, C for mean diameter (cm) of growth of fungal colony in control and T for treated Petri dishes.\u003c/p\u003e\n\u003cp\u003eThe corrected percentage inhibition (IC) was determined with the following equation:\u003c/p\u003e\n\u003cp\u003eIC = (I\u0026minus;CF)/(100\u0026minus;CF) \u0026times;100\u003c/p\u003e\n\u003cp\u003eHere, CF is calculated as:\u003c/p\u003e\n\u003cp\u003eCF = [(90 \u0026ndash; C)/C] \u0026times; 100\u003c/p\u003e\n\u003cp\u003eWhere, 90 is Petri plate diameter (mm) and C represent fungal mycelial growth (mm) in control plate.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.5 Nematicidal bioassay\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAll synthesized compounds were evaluated for \u003cem\u003ein vitro\u003c/em\u003e nematicidal activity using a water screening method. \u003cem\u003eM. incognita\u003c/em\u003e infected root galls were obtained from glasshouse of Division of Nematology, ICAR-Indian Agricultural Research Institute, New Delhi. For extraction of nematode culture, galls were incubated at 25-30 \u0026deg;C for 2-3 days, which facilitate the hatching of eggs. Subsequently, nematode population counted and 100 J2s per mL was prepared through dilution.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eSynthesized compound\u0026rsquo;s stock solution of 1000 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e was prepared in DMSO. The five test concentrations (200, 100, 50, 25 and 12.5 \u0026micro;g mL\u003csup\u003e-1\u003c/sup\u003e) were prepared through serial dilution from stock solution. Velum prime was taken as positive control\u0026nbsp;for\u003cem\u003e\u0026nbsp;M. incognita\u003c/em\u003e. A 1 mL suspension of nematodes (J2s) with 1 mL of test compound of different concentrations were added into 24-well culture plates and incubated at 28\u0026plusmn;2 \u0026deg;C in BOD in triplicates. Both living and dead J2s nematodes were counted in each treatment using a counting dish under stereoscopic binocular microscope. The mortality of J2s nematodes was recorded at 24, 48, 72 and 96 h (Yadav et al., 2021 and 2022; Kumar et al., 2023). The mortality rate was determined by Abbott\u0026apos;s formula (Abbott, 1925).\u003c/p\u003e\n\u003cp\u003eCorrected mortality percentage = [(T - C) / (100 - C)] \u0026times; 100\u003c/p\u003e\n\u003cp\u003eHere, T and C represents total mortality in the treatment and control, respectively.\u003c/p\u003e\n\u003cp\u003eED\u003csub\u003e50\u003c/sub\u003e values (effective dose for 50% inhibition) for antifungal and LC\u003csub\u003e50\u003c/sub\u003e values (lethal concentration for 50% inhibition) for nematicidal activities were expressed in \u0026micro;g mL\u003csup\u003e-1\u003c/sup\u003e, computed by probit analysis using the SPSS statistical package (version 28.0).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.6 Molecular docking:\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eMolecular docking is an essential tool for drug and agrochemical discovery, helping in virtual screening of potential candidates as well as providing insights into the mechanism of action of a certain compound (Tripathi et al., 2024). In this study, cutinase and elongation factor proteins were selected as targets for the fungicidal activity whereas acetylcholinesterase was chosen as a target site for nematicidal action. Cutinase and elongation factor both play a crucial role in growth, survival, and virulence of both the fungi. Hence, these enzymes are a potential target for developing new antifungal agents. Similarly, acetylcholinesterase is one of the most important enzyme responsible for maintaining steady transfer of nerve signal, making it a potential target site for various pests including nematodes (Godara et al., 2024). The target enzyme sequences were obtained from the NCBI database (https://www.ncbi.nlm.nih.gov/) and used for homology modeling with the SWISS-MODEL tool (https://swissmodel.expasy.org/). Protein and ligand preparation was conducted using AutoDock Vina. For protein preparation, water molecules were removed, polar hydrogens were added, and appropriate charges were assigned. The two-dimensional structures of the ligand compounds were initially created using ChemDraw Ultra 12.0, and subsequently converted to three-dimensional structures using Chem3D Pro 12.0, followed by energy minimization. These structures were then saved in pdb format using PyMOL and further processed for molecular docking in AutoDock Vina. Following the docking simulations, ligands were ranked based on their binding affinities. Detailed analyses of the most favorable ligand-protein interactions were performed using BIOVIA Discovery Studio.\u003c/p\u003e"},{"header":"3. Results and Discussion","content":"\u003cp\u003e\u003cstrong\u003e3.1 Synthesis and characterization\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eFifteen imidazolylchalcone derivatives were synthesized successfully using both conventional and ultrasonic methods (\u003cstrong\u003eScheme 1\u003c/strong\u003e). The ultrasonication method showed shorter reaction times (\u003cstrong\u003eFigure 1\u003c/strong\u003e) and higher yields compared to the conventional approach (\u003cstrong\u003eTable 2\u003c/strong\u003e).\u003c/p\u003e\n\u003cp\u003eIn imidazolylchalcones (\u003cstrong\u003eIC-1\u003c/strong\u003e to \u003cstrong\u003eIC-15\u003c/strong\u003e), two characteristic doublets of olefinic protons appeared at approximately 7.82 (1H, d, J = 15.9 Hz, H-3) and 7.67 (1H, d, J = 15.9 Hz, H-2) in the \u003csup\u003e1\u003c/sup\u003eH-NMR spectrum of all the compounds, confirming the formation of chalcones. In \u003csup\u003e13\u003c/sup\u003eC-NMR, the peak at \u0026delta; 188.14-203.51 (C-1) for the carbonyl moiety and peaks at \u0026delta; 140.75-147.01 (C-3) and 120.15-122.28 (C-2) for the olefinic carbon atoms of imidazolylchalcone were observed. The multiplet present between \u0026delta; 7.16-8.42 (4H, m, Ar-Hʹʹ) indicates the presence of a phenyl ring at the carbonyl carbon atom in the \u003csup\u003e1\u003c/sup\u003eH-NMR spectra of all the derivatives. A characteristic peak at 7.11-7.13 (H2\u0026rsquo;\u0026rdquo;) and the multiplet between \u0026delta; 7.15-8.12 (H3\u0026rsquo;\u0026rdquo; \u0026amp; H4\u0026rsquo;\u0026rdquo;) confirmed the presence of imidazolyl ring. The multiplet appearing between \u0026delta; 7.17-8.15 (Ar-H\u0026rsquo;) showed the presence of a substituted phenyl ring connected to the C-3 carbon and the chemical shift of this ring was influenced by different substituents like halo, nitro, hydroxy and methoxy groups. Characteristic singlets between \u0026delta; 3.78-3.83 indicated the presence of methoxy groups in the compounds IC-9 and IC-15. Similarly, compounds IC-13 and IC-14 showed characteristic singlet between 5.41- 5.57, due to the presence of hydroxy group. The structures of all the compounds were further confirmed by \u003csup\u003e13\u003c/sup\u003eC-NMR spectra, which matched well with the respective carbon atom values.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 2: Comparison of reaction time and yield of ultrasonic and conventional methods of imidazolylchalcones\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd rowspan=\"2\" style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eCompounds\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"2\" style=\"width: 224px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eConventional method\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"2\" style=\"width: 250px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eUltrasonication method\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eReaction time (min)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eYield (%)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eReaction time (min)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eYield (%)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-1\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e84\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e92\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-2\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e130\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e79\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-3\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e70\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e81\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-4\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e87\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-5\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e170\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e77\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e84\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-6\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e230\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e72\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e70\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e85\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-7\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e210\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e74\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e87\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-8\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e81\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e89\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-9\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e79\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e86\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-10\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e110\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e76\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e84\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-11\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e105\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-12\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e85\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-13\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e150\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e83\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e92\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-14\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e170\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e84\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e89\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-15\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 105px;\"\u003e\n \u003cp\u003e250\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 119px;\"\u003e\n \u003cp\u003e74\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 125px;\"\u003e\n \u003cp\u003e82\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u003cstrong\u003e3.2 Antifungal activity\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe \u003cem\u003ein vitro\u003c/em\u003e results of antifungal activity of synthesized imidazolylchalcone derivatives against \u003cem\u003eR. solani\u003c/em\u003e and \u003cem\u003eF. oxysporum\u003c/em\u003e are presented in \u003cstrong\u003eTable 3\u0026nbsp;\u003c/strong\u003eand\u003cstrong\u003e\u0026nbsp;Table 4\u003c/strong\u003e. \u0026nbsp;It showed that compound \u003cstrong\u003eIC-8\u003c/strong\u003e ((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\u003csub\u003e50\u003c/sub\u003e value of 0.69 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e , significantly lower than the ED\u003csub\u003e50\u003c/sub\u003e value (3.57 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) of commercially available hexaconazole 5% SC fungicide against \u003cem\u003eR. solani\u003c/em\u003e, followed by \u003cstrong\u003eIC-10\u003c/strong\u003e (ED\u003csub\u003e50\u003c/sub\u003e =2.28 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e), \u003cstrong\u003eIC-7\u003c/strong\u003e (ED\u003csub\u003e50\u003c/sub\u003e =4.35 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) and \u003cstrong\u003eIC-11\u0026nbsp;\u003c/strong\u003e(ED\u003csub\u003e50\u003c/sub\u003e =6.75 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) (\u003cstrong\u003eFigure 2\u003c/strong\u003e). However, in case of \u003cem\u003eF. oxysporum\u003c/em\u003e bioassay, compound \u003cstrong\u003eIC-4\u003c/strong\u003e ((E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(2-bromophenyl) prop-2-en-1-one; ED\u003csub\u003e50\u0026nbsp;\u003c/sub\u003e=119.22 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) showed highest activity\u003cem\u003e\u0026nbsp;\u003c/em\u003efollowed by \u003cstrong\u003eIC-3\u003c/strong\u003e (ED\u003csub\u003e50\u0026nbsp;\u003c/sub\u003e=135.76 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e), \u003cstrong\u003eIC-12\u003c/strong\u003e (ED\u003csub\u003e50\u0026nbsp;\u003c/sub\u003e=319.15) and \u003cstrong\u003eIC-1\u003c/strong\u003e (ED\u003csub\u003e50\u0026nbsp;\u003c/sub\u003e=361.62 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) as compared to positive control, Carbendazim 50 % WP (ED\u003csub\u003e50\u003c/sub\u003e =9.01 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) (\u003cstrong\u003eFigure 3\u003c/strong\u003e).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 3: \u003cem\u003ein vitro\u003c/em\u003e antifungal potential of imidazolylchalcone derivatives against \u003cem\u003eR. solani\u0026nbsp;\u003c/em\u003e\u003c/strong\u003e\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eCompounds\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eRegression equation\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026chi;\u003csup\u003e2\u003c/sup\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eED\u003csub\u003e50\u003c/sub\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003cp\u003e\u003cstrong\u003e(\u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eFiducial limit\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-1\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.714X +- 1.714\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e2.31\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e410.3\u003csup\u003eh\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e208.3-1867.47\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-2\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e1.143X +- 2.543\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.72\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e176.08\u003csup\u003egh\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e124.86-301.5\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-3\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.5X +- 0.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.17\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e8.48\u003csup\u003eb-e\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e0.35-19.64\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-4\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.714X +- 0.714\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.007\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e8.81\u003csup\u003eb-e\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e2.80-15.44\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-5\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e1.0X +- 1.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e14.84\u003csup\u003eb-e\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e8.39-21.22\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-6\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e1.0X +- 1.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e9.56\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e32.71\u003csup\u003ed-f\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e1.17-86.56\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-7\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.714X +- 0.514\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.27\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e4.35\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e0.65-9.59\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-8\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.571X +- 0.229\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.19\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e0.69\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e0.005-3.06\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-9\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.429X +- 0.529\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.27\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e15.13\u003csup\u003eb-f\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e2.26-29.02\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-10\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.5X +- 0.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.78\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e2.28\u003csup\u003ea-c\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e0.035-7.44\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-11\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.714X +- 0.514\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.28\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e6.75\u003csup\u003ea-d\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e1.85-12.51\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-12\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e1.0X +- 1.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e2.69\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e29.26\u003csup\u003ec-f\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e18.45-40.80\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-13\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.357X +- 0.757\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.03\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e134.62\u003csup\u003efg\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e63.53-3441.93\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-14\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.571X +- 0.971\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e0.66\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e36.42\u003csup\u003eef\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e19.31-57.81\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 151px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-15\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 180px;\"\u003e\n \u003cp\u003e0.857X +- 1.257\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 66px;\"\u003e\n \u003cp\u003e2.34\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 84px;\"\u003e\n \u003cp\u003e22.66\u003csup\u003eb-f\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 120px;\"\u003e\n \u003cp\u003e13.37-32.01\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e*Hexaconazole 5% SC, ED\u003csub\u003e50\u003c/sub\u003e= 3.57 \u0026micro;g mL\u003csup\u003e-1\u003c/sup\u003e\u003c/p\u003e\n\u003cp\u003e*ED\u003csub\u003e50\u003c/sub\u003e values with different superscripts are significantly different (p\u0026lt;0.001).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 4: \u003cem\u003ein vitro\u003c/em\u003e antifungal potential of imidazolylchalcone derivatives against \u003cem\u003eF. oxysporum\u003c/em\u003e.\u003c/strong\u003e\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eCompounds\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eRegression equation\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026chi;\u003csup\u003e2\u003c/sup\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eED\u003csub\u003e50\u003c/sub\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003cp\u003e\u003cstrong\u003e(\u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eFiducial limit\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-1\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.86X +- 2.06\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e1.01\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e361.62\u003csup\u003ea-d\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e185.7-1664.54\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-2\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.86X +- 2.46\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.34\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e1272.2\u003csup\u003ec-f\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e459.65-17661.6\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-3\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.86X +- 1.86\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.79\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e135.76\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e93.06-252.34\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-4\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.86X +- 1.86\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e1.11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e119.22\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e85.21-198.87\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-5\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.86X +- 2.26\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.34\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e400.44\u003csup\u003ea-e\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e221.7-1298.64\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-6\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.893X +- 2.643\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.73\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e1088.69\u003csup\u003eef\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e461.57-7540.64\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-7\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.86X +- 2.46\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e1.60\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e1122.79\u003csup\u003ed-f\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e452.49-9494.94\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-8\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.86X +- 2.26\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.34\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e532.89\u003csup\u003ea-e\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e259.81-2618.13\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-9\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.571X +- 1.771\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.16\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e1174.88\u003csup\u003eb-e\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e387.61-32677.63\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-10\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.71X +- 1.91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.29\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e535.24\u003csup\u003ea-e\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e255.58-2889.14\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-11\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.71X +- 1.91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e615.33\u003csup\u003ea-e\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e266.31-5112.63\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-12\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e0.71X +- 1.71\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.23\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e319.15\u003csup\u003ea-c\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e169.51-1319.40\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-13\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e1.071X +- 3.321\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e1.18\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e1674.03\u003csup\u003eef\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e599.19-21776.24\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-14\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e1.0X +- 3.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e1.36\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e1260.7\u003csup\u003eef\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e517.01-9960.98\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 132px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-15\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 161px;\"\u003e\n \u003cp\u003e1.286X +- 3.886\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 47px;\"\u003e\n \u003cp\u003e0.53\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 104px;\"\u003e\n \u003cp\u003e1052.59\u003csup\u003ef\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 157px;\"\u003e\n \u003cp\u003e494.08-5622.39\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e*Carbendazim 50% WP, ED\u003csub\u003e50\u003c/sub\u003e= 9.132 \u0026micro;g mL\u003csup\u003e-1\u003c/sup\u003e\u003c/p\u003e\n\u003cp\u003e*ED\u003csub\u003e50\u003c/sub\u003e values with different superscripts are significantly different (p\u0026lt;0.001).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e3.3 Nematicidal activity\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe results of \u003cem\u003ein vitro\u003c/em\u003e nematicidal activity of synthesized imidazolylchalcones against \u003cem\u003eM. incognita\u0026nbsp;\u003c/em\u003e(root knot nematode) are presented in \u003cstrong\u003eTable 5\u003c/strong\u003e, which revealed that compound \u003cstrong\u003eIC-6\u003c/strong\u003e (LC\u003csub\u003e50\u003c/sub\u003e = 33.62 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) showed highest activity followed by \u003cstrong\u003eIC-3\u003c/strong\u003e (LC\u003csub\u003e50\u0026nbsp;\u003c/sub\u003e=34.75 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e), \u003cstrong\u003eIC-5\u003c/strong\u003e (LC\u003csub\u003e50\u0026nbsp;\u003c/sub\u003e=64.79 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) and \u003cstrong\u003eIC-12\u003c/strong\u003e (LC\u003csub\u003e50\u0026nbsp;\u003c/sub\u003e=69.11 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e) after 24 hr observation as compared to positive control Velum Prime 34.48% SC (Fluopyrum; LC\u003csub\u003e50\u003c/sub\u003e = 3.46 \u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 5: Nematicidal activity of imidazolylchalcone derivatives against \u003cem\u003eM. incognita\u003c/em\u003e:\u003c/strong\u003e\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\" width=\"94%\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd rowspan=\"2\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eCompounds\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"4\" style=\"width: 78px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eLC\u003csub\u003e50\u003c/sub\u003e (\u0026mu;g mL\u003csup\u003e-1\u003c/sup\u003e)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 19px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e24 hr\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 19px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e48 hr\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 19px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e72 hr\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 19px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e96 hr\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-1\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e84.0\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e77.15\u003csup\u003ee\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e70.49\u003csup\u003ef\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e66.43\u003csup\u003ed\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-2\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e87.76\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e82.52\u003csup\u003ed\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e77.93\u003csup\u003ed\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e68.99\u003csup\u003ec\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-3\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e34.75\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e25.98\u003csup\u003ei\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e24.09\u003csup\u003ek\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e23.46\u003csup\u003ei\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-4\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e87.19\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e83.55\u003csup\u003ed\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e72.60\u003csup\u003ee\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e59.65\u003csup\u003ee\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-5\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e64.79\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e59.25\u003csup\u003efg\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e53.93\u003csup\u003eg\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e47.53\u003csup\u003eg\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-6\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e33.62\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e24.27\u003csup\u003ei\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e21.29\u003csup\u003el\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e19.49\u003csup\u003ej\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-7\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e90.13\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e82.8\u003csup\u003ed\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e72.45\u003csup\u003ee\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e58.32\u003csup\u003ee\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-8\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e133.22\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e122.9\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e96.11\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e77.65\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-9\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e141.63\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e114.64\u003csup\u003ec\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e92.50\u003csup\u003ec\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e75.27\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-10\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e195.84\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e128.47\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e104.98\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e81.88\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-11\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e84.95\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e60.79\u003csup\u003ef\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e43.55\u003csup\u003eh\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e32.06\u003csup\u003eh\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-12\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e69.11\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e50.10\u003csup\u003eh\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e38.14\u003csup\u003ej\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e30.50\u003csup\u003eh\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-13\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e78.05\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e55.85\u003csup\u003eg\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e41.08\u003csup\u003ei\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e29.74\u003csup\u003eh\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-14\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e85.77\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e56.99\u003csup\u003eg\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e40.49\u003csup\u003ei\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e29.55\u003csup\u003eh\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 21px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-15\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e172.89\u003csup\u003eab\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e123.69\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e77.92\u003csup\u003ed\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 19px;\"\u003e\n \u003cp\u003e53.87\u003csup\u003ef\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e*Fluopyram (Velum) LC\u003csub\u003e50\u003c/sub\u003e:\u003csub\u003e\u0026nbsp;\u003c/sub\u003e3.46 (24 hr), 1.99 (48 hr), 0.14 (72 hr), 0.05 (96 hr)\u0026nbsp;\u0026micro;g mL\u003csup\u003e-1\u003c/sup\u003e\u003c/p\u003e\n\u003cp\u003e*LC\u003csub\u003e50\u003c/sub\u003e values with different superscripts are significantly different (p\u0026lt;0.001).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e3.4 Molecular docking:\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eMolecular docking is a computational technique that enables virtual exploration of the interactions between proteins and molecules. This method plays a crucial role in the rational design, optimization, and characterization of protein-ligand interactions, contributing to the development of novel agrochemicals. In this study, molecular docking was employed to investigate the binding interactions of selected compounds with key target sites in two pathogenic fungi, \u003cem\u003eSclerotium rolfsii\u003c/em\u003e and \u003cem\u003eFusarium oxysporum\u003c/em\u003e, as well as in the nematode \u003cem\u003eMeloidogyne incognita\u003c/em\u003e. The study focused on two primary fungal targets: cutinase and elongation factor. Cutinases, hydrolytic enzymes found in fungal cell walls, catalyze the breakdown of glycosidic bonds in chitin. These enzymes play a pivotal role in facilitating fungal penetration into plant root tissues, enabling pathogens like \u003cem\u003eF. oxysporum\u003c/em\u003e to establish primary infections. Due to its critical role in the pathogenic mechanism of \u003cem\u003eF. oxysporum\u003c/em\u003e, cutinase represents an attractive target for antifungal intervention, potentially disrupting the fungus\u0026rsquo;s ability to cause disease. Similarly, elongation factors, essential for fungal growth and survival, present another prime target for the development of fungicidal compounds (Taruna et al., 2023; Dimarogona et al., 2015; Godara et al., 2024). Additionally, acetylcholinesterase, a vital enzyme for the regulation of nerve signal transmission, was explored as a target in \u003cem\u003eM. incognita\u003c/em\u003e. This enzyme\u0026apos;s crucial role in maintaining steady nerve signal transfer makes it an important target for pest control strategies against nematodes (Yadav et al., 2024; Mondal et al., 2024). These docking studies provide valuable insights into the molecular interactions at these target sites, facilitating the design of effective antifungal and nematicidal agents.\u003c/p\u003e\n\u003cp\u003eThe compound under study showed promising interactions with their respective target enzymes, as summarized in \u003cstrong\u003eTable\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;6\u003c/strong\u003e. \u003cstrong\u003eIC\u003c/strong\u003e\u003cstrong\u003e-4\u003c/strong\u003e, the compound showing the best activity against \u003cem\u003eF\u003c/em\u003e. \u003cem\u003eoxysporum\u003c/em\u003e, strongly inhibited the activity of cutinase enzyme through conventional H bonding, C-H hydrogen bonding and \u0026pi;-Cation interactions involving the residues like ARG 102, ASN 427 and GLN 424; which was further stabilized by hydrophobic interaction such as \u0026pi;-Alkyl interactions involving ARG 425, ARG 380 and ARG 276. The compound \u003cstrong\u003eIC\u003c/strong\u003e\u003cstrong\u003e-8\u003c/strong\u003e was found to inhibit both the elongation factor and cutinase of \u003cem\u003eR\u003c/em\u003e. \u003cem\u003esoalni\u003c/em\u003e strongly, however, the binding with elongation factor was stronger (\u0026Delta;G = -9.7 kcal/mol) as compared to cutinase (\u0026Delta;G = -8.3 kcal/mol). This bonding was again attributed towards the conventional hydrogen bond and \u0026pi;-Anion bond, further strengthened by hydrophobic interactions such as \u0026pi;-Alkyl, \u0026pi;-\u0026sigma;, and \u0026pi;-\u0026pi; T shaped interactions. Similarly, the compound \u003cstrong\u003eIC\u003c/strong\u003e\u003cstrong\u003e-6\u003c/strong\u003e was found to bind favorably with acetylcholinesterase of \u003cem\u003eM\u003c/em\u003e. \u003cem\u003eincognita\u003c/em\u003e. Conventional hydrogen bond involving SER 252 and HIS 514, along with some hydrophobic interactions such as \u0026pi;-\u0026pi; stacked, \u0026pi;-\u0026sigma;, and \u0026pi;-\u0026pi; T shaped interactions, helped in the binding process. Some discrepancies were observed between the molecular docking results and the outcomes of the \u003cem\u003ein vitro\u003c/em\u003e experiments. Notably, while the compound \u003cstrong\u003eIC\u003c/strong\u003e\u003cstrong\u003e-4\u003c/strong\u003e demonstrated the most potent fungicidal activity against \u003cem\u003eFusarium oxysporum\u003c/em\u003e \u003cem\u003ein vitro\u003c/em\u003e, the \u003cem\u003ein silico\u003c/em\u003e studies ranked it below compound \u003cstrong\u003eIC\u003c/strong\u003e\u003cstrong\u003e-8\u003c/strong\u003e, which exhibited the highest binding affinity. This divergence can be attributed to the inherent complexities of biological systems \u003cem\u003ein vitro\u003c/em\u003e, which involve numerous interacting components, dynamic signaling pathways, and environmental fluctuations that are not fully accounted for in computational models. Furthermore, in actual biological environments, additional binding sites on the target molecule may become accessible, leading to interactions that are not predicted by \u003cem\u003ein silico\u003c/em\u003e docking analyses (Chen, 2015).\u0026nbsp;(\u003cstrong\u003eFigure 4\u003c/strong\u003e).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;6: Binding energies of synthesized compounds against various target sites\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\" width=\"99%\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd rowspan=\"3\" valign=\"top\" style=\"width: 9px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eCompound\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"5\" valign=\"top\" style=\"width: 90px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eBinding affinity (kcal/mol)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" valign=\"top\" style=\"width: 36px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u003cem\u003eFusarium oxysporum\u003c/em\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"2\" valign=\"top\" style=\"width: 36px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u003cem\u003eRhizoctonia solani\u003c/em\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u003cem\u003eMeloidogyne incognita\u003c/em\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eCutinase\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eElongation factor\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eCutinase\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eElongation factor\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eAcetylcholinesterase\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-1\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.7\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-2\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.5\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-3\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.8\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-4\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.5\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-5\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.6\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-6\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.7\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-7\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.9\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-8\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.7\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-9\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.6\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-10\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.5\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-11\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.5\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-12\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.6\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-13\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.4\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-14\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-9.3\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eIC-15\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-6.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-7.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 18px;\"\u003e\n \u003cp\u003e-8.7\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n"},{"header":"4. Conclusion","content":"\u003cp\u003eTo the best of our knowledge this is the first attempt to synthesize a series of imidazolylchalcone derivatives through ultrasonication method, which is considered as green synthesis and gave higher yield with lesser reaction time as compared to conventional method. The synthesized compounds were characterized by spectroscopic techniques and their efficacy was evaluated against soil borne fungi (\u003cem\u003eR. solani\u003c/em\u003e and \u003cem\u003eF. oxysporum\u003c/em\u003e) and nematicidal activity against \u003cem\u003eM. incognita\u003c/em\u003e. Bio efficacy results revealed that compound ((E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(4-benzyloxy)phenyl)prop-2-en-1-one) (\u003cb\u003eIC-8\u003c/b\u003e; ED\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;0.69 \u0026micro;g mL\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e) was found to be most active against \u003cem\u003eR. solani\u003c/em\u003e, which was better than commercial hexaconazole 5% SC (ED\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;3.75 \u0026micro;g mL\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e). Whereas, in case \u003cem\u003eF. oxysporum\u003c/em\u003e, compound (E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(2-bromophenyl) prop-2-en-1-one (\u003cb\u003eIC-4\u003c/b\u003e; ED\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;119.22 \u0026micro;g mL\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e) showed highest activity as compared with Carbendazim 50% WP (ED\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;9.01 \u0026micro;g mL\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e). In nematicidal bioassay, compound (E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(3-nitrophenyl) prop-2-en-1-one (\u003cb\u003eIC-6\u003c/b\u003e; LC\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;33.62 \u0026micro;g mL\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e) was most active against \u003cem\u003eM. incognita\u003c/em\u003e (root-knot nematode after 24 h of inoculation as compared with commercial compound Velum Prime (LC\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;3.46 \u0026micro;g mL\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e). However, the nematicidal activity shown by imidazolylchalcone derivatives was lower than the commercial one. Furthermore, molecular docking investigations supported the findings of biological assessments, identifying \u003cb\u003eIC-8\u003c/b\u003e as the most effective compound against \u003cem\u003eR. solani\u003c/em\u003e with highest binding energy (-8.5 kcal mol\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e), \u003cb\u003eIC-4\u003c/b\u003e (-8.0 kcal mol\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e) against cutinase enzyme of \u003cem\u003eF. oxysporium\u003c/em\u003e and \u003cb\u003eIC-6\u003c/b\u003e (-9.7 kcal mol\u003csup\u003e-\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003e) against acetylcholinesterase enzyme of \u003cem\u003eM. incognita\u003c/em\u003e. These compounds could serve as lead compounds for the development of potent molecules intended for use as pest control agents.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eEthics Approval and Consent to participate:\u0026nbsp;\u003c/strong\u003eNot applicable\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConsent for publication:\u0026nbsp;\u003c/strong\u003eAll authors give consent for the publication of the manuscript in the Journal of BMC Chemistry\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAvailability of data and materials:\u0026nbsp;\u003c/strong\u003eThe data generated and/or analyzed during the current study are not publicly available due feasibility of the study to begin a further \u003cem\u003ein-vivo\u003c/em\u003e trial; however, they are available from the corresponding author upon reasonable request.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eCompeting interests:\u0026nbsp;\u003c/strong\u003eThe authors declare that they have no competing interests.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding:\u0026nbsp;\u003c/strong\u003eFinancial support received from PI Industries Ltd. And CII, New Delhi as Prime Minister\u0026rsquo;s Fellowship and other facility support from ICAR- Indian Agricultural Research Institute, New Delhi-110012.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthors\u0026apos; contributions:\u0026nbsp;\u003c/strong\u003eRK: Design of the work, acquisition, analysis, interpretation of data and drafted work, KPT: Analysis, interpretation of data, PK: Design of the work, substantively revised, RG: Interpretation of data and drafted work, SRM: Analysis and draft revision, VK: Experimentation, draft revision, PCM: Analysis and interpretation of data, J: Experimentation and drafting, VSR: \u0026nbsp;Design of the work, interpretation of data, P: Analysis, interpretation of data, VS: Interpretation of data, DK: Substantively revised draft. NAS: Conceptualize, supervision, design of the work, interpretation of data.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAcknowledgment:\u0026nbsp;\u003c/strong\u003eThe authors gratefully acknowledge ICAR-Indian Agricultural Research Institute for providing facilities to carry out the research work and thankful for the financial support received from PI Industries Ltd., CII, New Delhi and Prime Minister\u0026rsquo;s Fellowship for financial support.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eSupporting information includes chemical structure, \u003csup\u003e1\u003c/sup\u003eH-NMR, \u003csup\u003e13\u003c/sup\u003eC-NMR and HRMS spectra of most effective compounds IC-4, IC-6 and IC-8 with IC-1 as representative of imidazolylchalcone derivatives.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eAbbott, W.S. A method of computing the effectiveness of an insecticide. \u003cem\u003eJ. Econ. Entomol\u003c/em\u003e., 1925, 18(2), 265-267.\u003c/li\u003e\n\u003cli\u003eBrevik, K., Schoville, S.D., Mota‐Sanchez, D. and Chen, Y.H. Pesticide durability and the evolution of resistance: A novel application of survival analysis. \u003cem\u003ePest Manag. Sci\u003c/em\u003e., 2018, 74(8), 1953-1963. https://doi.org/10.1002/ps.4899\u003c/li\u003e\n\u003cli\u003eChen, Y.C. Beware of docking!. \u003cem\u003eTrends Pharmacol. Sci.\u003c/em\u003e, 2015, 36(2), 78-95.\u003c/li\u003e\n\u003cli\u003eDeVito, S.C. On the design of safer chemicals: A path forward. \u003cem\u003eGreen Chem.\u003c/em\u003e, 2016, 18(16), 4332-4347. https://doi.org/10.1039/C6GC00526H \u003c/li\u003e\n\u003cli\u003eDimarogona, M., Nikolaivits, E., Kanelli, M., Christakopoulos, P., Sandgren, M. and Topakas, E., 2015. Structural and functional studies of a \u003cem\u003eFusarium oxysporum\u003c/em\u003e cutinase with polyethylene terephthalate modification potential. \u003cem\u003eBiochimica et Biophysica Acta\u003c/em\u003e (BBA)-General Subjects, 2015, 1850(11), 2308-2317.\u003c/li\u003e\n\u003cli\u003eEl-Kazzaz, M.K., Ghoneim, K.E., Agha, M.K.M., Helmy, A., Behiry, S.I., Abdelkhalek, A., Saleem, M.H., Al-Askar, A.A., Arishi, A.A. and Elsharkawy, M.M. Suppression of pepper root rot and wilt diseases caused by \u003cem\u003eRhizoctonia solani\u003c/em\u003e and \u003cem\u003eFusarium oxysporum\u003c/em\u003e. \u003cem\u003eLife\u003c/em\u003e, 2022, 12(4), 587.\u003c/li\u003e\n\u003cli\u003eGawade, B.H., Chaturvedi, S., Khan, Z., Pandey, C.D., Gangopadhyay, K.K., Dubey, S.C. and Chalam, V.C. Evaluation of brinjal germplasm against root-knot nematode, \u003cem\u003eMeloidogyne incognita\u003c/em\u003e. \u003cem\u003eIndian Phytopathol.\u003c/em\u003e, 2022, 75(2), 449-456.\u003c/li\u003e\n\u003cli\u003eGodara, R., Kaushik, P., Tripathi, K., Kumar, R., Rana, V.S., Kumar, R., Mandal, A., Shanmugam, V., Pankaj and Shakil, N.A. Green synthesis, structure\u0026ndash;activity relationships, \u003cem\u003ein silico\u003c/em\u003e molecular docking, and antifungal activities of novel prenylated chalcones. \u003cem\u003eFront. Chem.\u003c/em\u003e, 2024, 12, 1389848. https://doi.org/10.3389/fchem.2024.1389848\u003c/li\u003e\n\u003cli\u003eHassan, M.A., Pham, T.H., Shi, H. and Zheng, J. Nematodes threats to global food security. \u003cem\u003eActa Agriculturae Scandinavica, Section B\u0026ndash;Soil \u0026amp; Plant Science\u003c/em\u003e, 2013, 63(5), 420-425.\u003c/li\u003e\n\u003cli\u003eKarmakar, R. and Mukhopadhyay, C. 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L.; Thapliyal, P. N. \u0026ldquo;Fungicides in plant disease control,\u0026rdquo; in \u003cem\u003eEvaluation of fungicides\u003c/em\u003e. Editors Y. L. Nene and P. N. Thapliyal (New Delhi, India: Oxford and IBH Publishing Co.),1979, 406\u0026ndash;428.\u003c/li\u003e\n\u003cli\u003eOraon, S., Padamini, R., Shahni, Y.S., Das, N., Sinha, D., Sujatha, G.S., Singh, O.B. and Karanwal, R., 2024. Impact of Emerging Pathogens in Crop Production.\u003cem\u003e Microbiol. Res. J. Int.\u003c/em\u003e, 34(7), 80-92.\u003c/li\u003e\n\u003cli\u003ePuri, S., Kaur, B., Parmar, A. and Kumar, H. Applications of ultrasound in organic synthesis-a green approach. \u003cem\u003eCurr Org Chem.\u003c/em\u003e, 2013, 17(16), 1790-1828.\u003c/li\u003e\n\u003cli\u003eRani, N., Sharma, A., Kumar Gupta, G. and Singh, R. Imidazoles as potential antifungal agents: A review. \u003cem\u003eMini Rev Med Chem\u003c/em\u003e, 2013, 13(11), 1626-1655.\u003c/li\u003e\n\u003cli\u003eShakil, N.A., Singh, M.K., Kumar, J., Sathiyendiran, M., Kumar, G., Singh, M.K., Pandey, R.P., Pandey, A. and Parmar, V.S. Microwave synthesis and antifungal evaluations of some chalcones and their derived diaryl-cyclohexenones. \u003cem\u003eJ. Environ. Sci. Health B\u003c/em\u003e, 2010, 45(6), 524-530. https://doi.org/10.1080/03601234.2010.493482 \u003c/li\u003e\n\u003cli\u003eShakil, N.A., Singh, M.K., Sathiyendiran, M. and Kumar, J. Microwave accelerated solvent-free synthesis and antifungal evaluations of flavanones. \u003cem\u003eArch. Phytopathol. Pflanzenschutz.\u003c/em\u003e, 2011, 44(20), 1958-1965. https://doi.org/10.1080/03235408.2010.544467 \u003c/li\u003e\n\u003cli\u003eShakil, N.A., Singh, M.K., Sathiyendiran, M., Kumar, J. and Padaria, J.C. Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives. \u003cem\u003eEur. J. Med. Chem.\u003c/em\u003e, 2013, 59, 120-131. https://doi.org/10.1016/j.ejmech.2012.10.038\u003c/li\u003e\n\u003cli\u003eSingh, B.K., Singh, S.S.B.K. and Yadav, S.M. Some important plant pathogenic disease of brinjal (\u003cem\u003eSolanum melongena\u003c/em\u003e L.) and their management. \u003cem\u003ePlant Pathol. J.,\u003c/em\u003e 2014, 13(3), 208-213.\u003c/li\u003e\n\u003cli\u003eSiwach, A. and Verma, P.K. Synthesis and therapeutic potential of imidazole containing compounds. \u003cem\u003eBMC chem\u003c/em\u003e, 2021, 15, 1-69.\u003c/li\u003e\n\u003cli\u003eTaruna, A., Dewi, R.R., Hadiwijoyo, E., Yulianah, I., Syib\u0026rsquo;li, M.A. and Abadi, A.L. Molecular Docking and In Vitro Study Revealed the Inhibition Mechanism of Cutinase of \u003cem\u003eFusarium oxsyporum\u003c/em\u003e f. sp lycopersici by Natural Compounds of Local Turmeric in Indonesia. AGRIVITA, \u003cem\u003eJ Agric Sci\u003c/em\u003e, 45(3), 2023, 554-569.\u003c/li\u003e\n\u003cli\u003eTolomeu, H.V. and Fraga, C.A.M. Imidazole: synthesis, functionalization and physicochemical properties of a privileged structure in medicinal chemistry. \u003cem\u003eMolecules\u003c/em\u003e, 2023, 28(2), p.838.\u003c/li\u003e\n\u003cli\u003eTripathi, K., Kaushik, P., Yadav, D.K., Kumar, R., Misra, S.R., Godara, R., Bashyal, B.M., Rana, V.S., Kumar, R., Yadav, J. and Shakil, N.A. Synthesis, antifungal evaluation, two‐dimensional quantitative structure\u0026ndash;activity relationship and molecular docking studies of isoxazole derivatives as potential fungicides. \u003cem\u003ePest Manag. Sci.\u003c/em\u003e2024. https://doi.org/10.1002/ps.8152.\u003c/li\u003e\n\u003cli\u003eUl Haq, I., Sarwar, M.K., Faraz, A. and Latif, M.Z. Synthetic chemicals: Major component of plant disease management. \u003cem\u003ePlant disease management strategies for sustainable agriculture through traditional and modern approaches\u003c/em\u003e, 2020, 53-81.\u003c/li\u003e\n\u003cli\u003eYadav, D.K., Kaushik, P., Pankaj, Rana, V.S., Kamil, D., Khatri, D. and Shakil, N.A. Microwave assisted synthesis, characterization and biological activities of ferrocenyl chalcones and their QSAR analysis. \u003cem\u003eFront. Chem.\u003c/em\u003e, 2019, 7, 814. https://doi.org/10.3389/fchem.2019.00814\u003c/li\u003e\n\u003cli\u003eYadav, D.K., Kaushik, P., Tripathi, K.P., Rana, V.S., Yeasin, M., Kamil, D., Pankaj, Khatri, D. and Shakil, N.A. Bioefficacy evaluation of ferrocenyl chalcones against \u003cem\u003eMeloidogyne incognita\u003c/em\u003e and \u003cem\u003eSclerotium rolfsii\u003c/em\u003e infestation in tomato. \u003cem\u003eJ. Environ. Sci. Health B.\u003c/em\u003e, 2022, 57(3), 192-200. https://doi.org/10.1080/03601234.2022.2042154 \u003c/li\u003e\n\u003cli\u003eYadav, D.K., Tripathi, K.P., Pankaj, P., Kaushik, P., Rana, V.S., Khatri, D. and Shakil, N.A. Antinemic activity of ferrocenyl chalcones against \u003cem\u003eMeloidogyne incognita\u003c/em\u003e infestation in tomato. \u003cem\u003eIndian J. Agric. Sci.\u003c/em\u003e, 2021, 91(2), 305-9. https://doi.org/ 10.56093/ijas.v91i2.111644 \u003c/li\u003e\n\u003cli\u003eYadav, N., Kumar, R., Sangwan, S., Dhanda, V., Rani, R., Devi, S., Duhan, A., Sindhu, J., Chauhan, S., Malik, V.K. and Yadav, S. Design, synthesis, nematicidal evaluation, and molecular docking study of pyrano [3, 2-c] pyridones against \u003cem\u003eMeloidogyne incognita\u003c/em\u003e. \u003cem\u003eJ. Agric. Food Chem.\u003c/em\u003e, 2024, 72(28), 15512-15522.\u003c/li\u003e\n\u003c/ol\u003e"},{"header":"Scheme","content":"\u003cp\u003eScheme 1 is available in the Supplementary Files section.\u003c/p\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"bmc-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"ccjo","sideBox":"Learn more about [BMC Chemistry](https://bmcchem.biomedcentral.com/)","snPcode":"","submissionUrl":"https://www.editorialmanager.com/ccjo/default.aspx","title":"BMC Chemistry","twitterHandle":"BMC_series","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"em","reportingPortfolio":"BMC Series","inReviewEnabled":true,"inReviewRevisionsEnabled":true},"keywords":"Green Synthesis, Imidazolylchalcones, Ultrasonication, Molecular Docking, Fusarium oxysporium, Rhizoctonia solani, Meloidogyne incognita","lastPublishedDoi":"10.21203/rs.3.rs-5803429/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-5803429/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eChalcones 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 \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eH-NMR, \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC-NMR and LC-HRMS. These molecules were evaluated for their fungicidal activity against \u003cem\u003eRhizoctonia solani \u0026amp; Fusarium oxysporum\u003c/em\u003e and nematicidal activity against \u003cem\u003eMeloidogyne incognita\u003c/em\u003e. The result revealed that compound \u003cb\u003eIC-8\u003c/b\u003e ((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\u003csub\u003e50\u003c/sub\u003e value of 0.69 \u0026micro;g mL\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e, significantly lower than the ED\u003csub\u003e50\u003c/sub\u003e value (3.57 \u0026micro;g mL\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) of commercially available hexaconazole 5% SC fungicide against \u003cem\u003eR. solani\u003c/em\u003e, while \u003cb\u003eIC-4\u003c/b\u003e ((E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(2-bromophenyl) prop-2-en-1-one; ED\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;119.22 \u0026micro;g mL\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) showed highest activity against \u003cem\u003eF. oxysporum\u003c/em\u003e as compared with the positive control Carbendazim 50% Wettable powder (WP; ED\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;9.01 \u0026micro;g mL\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e). The compound \u003cb\u003eIC-6\u003c/b\u003e ((E)-1-(4-(1 H-imidazole-1-yl) phenyl)-3-(3-nitrophenyl) prop-2-en-1-one; LC\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;33.62 \u0026micro;g mL\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) was found to be most active against \u003cem\u003eM. incognita\u003c/em\u003e (LC\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;31.25 \u0026micro;g mL\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) after 24 h of inoculation but lesser active than positive control Velum Prime 34.48% SC (Fluopyrum; LC\u003csub\u003e50\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;3.46 \u0026micro;g mL\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e). 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 \u003cem\u003evia\u003c/em\u003e BIOVIA Discovery Studio. Ligand-protein interactions strengthened results of biological evaluation that predicted compound \u003cb\u003eIC-8\u003c/b\u003e as the most active with highest binding energy (-8.5 kcal mol\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) against \u003cem\u003eR\u003c/em\u003e. \u003cem\u003esolani\u003c/em\u003e, \u003cb\u003eIC-4\u003c/b\u003e (-8.0 kcal mol\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) against cutinase of \u003cem\u003eF\u003c/em\u003e. \u003cem\u003eoxysporum\u003c/em\u003e and \u003cb\u003eIC-6\u003c/b\u003e (-9.7 kcal mol\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) with acetylcholinesterase (AChE) of \u003cem\u003eM\u003c/em\u003e. \u003cem\u003eincognita\u003c/em\u003e.\u003c/p\u003e","manuscriptTitle":"Green Synthesis, Characterization, In Silico Molecular Docking and Biological Evaluation of Imidazolylchalcones as Promising Fungicide/s and Nematicide/s","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-01-15 09:42:17","doi":"10.21203/rs.3.rs-5803429/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-01-15T13:51:18+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-01-14T08:36:18+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-01-14T08:33:09+00:00","index":"","fulltext":""},{"type":"submitted","content":"BMC Chemistry","date":"2025-01-10T11:37:36+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"bmc-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"ccjo","sideBox":"Learn more about [BMC Chemistry](https://bmcchem.biomedcentral.com/)","snPcode":"","submissionUrl":"https://www.editorialmanager.com/ccjo/default.aspx","title":"BMC Chemistry","twitterHandle":"BMC_series","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"em","reportingPortfolio":"BMC Series","inReviewEnabled":true,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"93170809-4897-4a4e-be80-5f8851e8f65e","owner":[],"postedDate":"January 15th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2025-05-05T16:06:24+00:00","versionOfRecord":{"articleIdentity":"rs-5803429","link":"https://doi.org/10.1186/s13065-025-01451-z","journal":{"identity":"bmc-chemistry","isVorOnly":false,"title":"BMC Chemistry"},"publishedOn":"2025-04-29 15:57:22","publishedOnDateReadable":"April 29th, 2025"},"versionCreatedAt":"2025-01-15 09:42:17","video":"","vorDoi":"10.1186/s13065-025-01451-z","vorDoiUrl":"https://doi.org/10.1186/s13065-025-01451-z","workflowStages":[]},"version":"v1","identity":"rs-5803429","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-5803429","identity":"rs-5803429","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}