Discovery of novel acrylopimaric acid triazole derivatives as promising antifungal agents

IF 3.8 1区农林科学 Q1 AGRONOMY Pest Management Science Pub Date : 2024-03-26 DOI:10.1002/ps.8102

Xu Han, Renle Xu, Shihao Gu, Yue Kong, Yuhang Lou, Yanqing Gao, Shibin Shang, Zhanqian Song, Jie Song, Jian Li

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Abstract

BACKGROUND

To further develop potential natural fungicides, two series of new acrylopimaric acid triazole derivatives were synthesized, and their antifungal activities were tested and evaluated.

RESULTS

In 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.

CONCLUSION

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发现新型丙烯酰亚胺酸三唑衍生物作为有前途的抗真菌剂。

背景：为进一步开发潜在的天然杀菌剂，合成了两个系列的丙烯酰基丙二酸三唑新衍生物，并对其抗真菌活性进行了测试和评估：体外抗真菌活性结果表明，化合物 5m 对根瘤菌（Rhizoctonia solani）具有显著的抑制活性，EC50 值为 1.528 mg/L。其抗真菌效果与市售杀菌剂氟康唑、环唑醇和丙环唑相当（EC50 值分别为 1.441、0.815 和 1.173 mg/L）。随后，对化合物 5m 进行了体内研究，结果表明其对 R. solani 具有显著的保护和治疗作用。此外，生理生化研究表明，化合物 5m 能破坏 R. solani 菌丝的形态和超微结构，增加细胞膜的通透性，抑制麦角甾醇的合成，提高水稻植物防御酶的活性。3D-QSAR 研究表明，分子结构对化合物 5m 与受体的结合有显著影响，从而增强了其抗真菌活性：结论：化合物 5m 对 R. solani 具有优异的抗真菌活性，有望成为防治 R. solani 的候选杀真菌剂。本文受版权保护。保留所有权利。

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来源期刊

Pest Management Science 农林科学-昆虫学

CiteScore

7.90

自引率

9.80%

发文量

553

审稿时长

4.8 months

期刊介绍： Pest Management Science is the international journal of research and development in crop protection and pest control. Since its launch in 1970, the journal has become the premier forum for papers on the discovery, application, and impact on the environment of products and strategies designed for pest management. Published for SCI by John Wiley & Sons Ltd.