Discovery of novel acrylopimaric acid triazole derivatives as promising antifungal agents

Author:

Han Xu1,Xu Renle1,Gu Shihao1,Kong Yue1,Lou Yuhang1,Gao Yanqing2,Shang Shibin3,Song Zhanqian3,Song Jie4,Li Jian1ORCID

Affiliation:

1. Jiangsu Province Key Laboratory of Biomass Energy and Materials, College of Forestry Northwest A&F University Yangling P. R. China

2. College of Plant Protection Northwest A&F University Yangling P. R. China

3. Institute of Chemical Industry of Forest Products Chinese Academy of Forestry Nanjing P. R. China

4. Department of Chemistry and Biochemistry University of Michigan‐Flint Flint MI USA

Abstract

AbstractBACKGROUNDTo further develop potential natural fungicides, two series of new acrylopimaric acid triazole derivatives were synthesized, and their antifungal activities were tested and evaluated.RESULTSIn vitro antifungal activity results indicated that compound 5m exhibited significant inhibitory activity against Rhizoctonia solani with an half maximal effective concentration (EC50) value of 1.528 mg/L. Its antifungal effect was comparable to that of the commercially available fungicide fluconazole, epoxiconazole and propiconazole (EC50 values of 1.441, 0.815 and 1.173 mg/L). Subsequently, in vivo studies were conducted on compound 5m, which revealed its significant protective and curative effects against R. solani. In addition, physiological and biochemical studies showed that compound 5m could disrupt the morphology and ultrastructure of R. solani mycelium, increase cell membrane permeability, inhibit ergosterol synthesis, and enhance the activity of defense enzymes in rice plants. Three‐dimensional quantitative structure–activity relationship (3D‐QSAR) studies revealed that the molecular structure significantly influenced the binding of compound 5m to the receptor, thereby enhancing its antifungal activity.CONCLUSIONCompound 5m exhibits excellent antifungal activity against R. solani, making it a promising candidate fungicide for the prevention and control of R. solani. © 2024 Society of Chemical Industry.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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