Synthesis, antifungal evaluation, two-dimensional quantitative structure-activity relationship and molecular docking studies of isoxazole derivatives as potential fungicides.

Autor: Tripathi K; Division of Agricultural Chemicals, ICAR-Indian Agricultural Research Institute, New Delhi, India.; ICAR-National Research Centre on Seed Spices, Ajmer, India.; The Graduate School, ICAR-Indian Agricultural Research Institute, New Delhi, India., Kaushik P; Division of Agricultural Chemicals, ICAR-Indian Agricultural Research Institute, New Delhi, India., Yadav DK; ICAR-Indian Institute of Soil Science, Bhopal, India., Kumar R; ICAR-Central Inland Fishries Research Institute, Guwahati, India., Misra SR; Division of Agricultural Chemicals, ICAR-Indian Agricultural Research Institute, New Delhi, India., Godara R; Division of Agricultural Chemicals, ICAR-Indian Agricultural Research Institute, New Delhi, India., Bashyal BM; Division of Plant Pathology, ICAR-Indian Agricultural Research Institute, New Delhi, India., Rana VS; Division of Agricultural Chemicals, ICAR-Indian Agricultural Research Institute, New Delhi, India., Kumar R; Division of Agricultural Chemicals, ICAR-Indian Agricultural Research Institute, New Delhi, India., Yadav J; Division of Plant Pathology, ICAR-Indian Agricultural Research Institute, New Delhi, India., Shakil NA; Division of Agricultural Chemicals, ICAR-Indian Agricultural Research Institute, New Delhi, India.
Jazyk: angličtina
Zdroj: Pest management science [Pest Manag Sci] 2024 May 01. Date of Electronic Publication: 2024 May 01.
DOI: 10.1002/ps.8152
Abstrakt: Background: Sheath blight and bakanae disease, prominent among emerging rice ailments, exert a profound impact on rice productivity, causing severe impediments to crop yield. Excessive use of older fungicides may lead to the development of resistance in the pathogen. Indeed, a pressing and immediate need exists for novel, low-toxicity and highly selective fungicides that can effectively combat resistant fungal strains.
Results: A series of 20 isoxazole derivatives were synthesized using alkoxy/halo acetophenones and N,N-dimethylformamidedimethylacetal. These compounds were characterized by various spectroscopic techniques, namely 1 H nuclear magnetic resonance (NMR), 13 C NMR and liquid chromatography-high-resolution mass spectrometry, and were evaluated for their fungicidal activity against Rhizoctonia solani and Fusarium fujikuroi. Compound 5n (5-(2-chlorophenyl) isoxazole) exhibited highest activity (effective dose for 50% inhibition [ED 50 ] = 4.43 μg mL -1 ) against R. solani, while 5p (5-(2,4-dichloro-2-hydroxylphenyl) isoxazole) exhibited highest activity (ED 50  = 6.7 μg mL -1 ) against F. fujikuroi. Two-dimensional quantitative structural-activity relationship (QSAR) analysis, particularly multiple linear regression (MLR) (Model 1), highlighted chi6chain and DistTopo as the key descriptors influencing fungicidal activity. Molecular docking studies revealed the potential of these isoxazole derivatives as novel fungicides targeting sterol 14α-demethylase enzyme, suggesting their importance as crucial intermediates for the development of novel and effective fungicides.
Conclusion: All test compounds were effective in inhibiting both fungi, according to the QSAR model, with various descriptors, such as structural, molecular shape analysis, electronic and thermodynamic, playing an important role. Molecular docking studies confirmed that these compounds can potentially replace commercially available fungicides and help control fungal pathogens in rice crops effectively. © 2024 Society of Chemical Industry.
(© 2024 Society of Chemical Industry.)
Databáze: MEDLINE
Externí odkaz: