Dai Peng, Ma Zihua, Dang Yuncong, Huang Jiaxuan, Xue Huizhen, Sun Yafang, Gu Yu-Cheng, Xia Qing, Zhang Weihua
Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing, China.
College of Economics and Management, Huaibei Institute of Technology, Anhui, China.
Pest Manag Sci. 2025 Mar;81(3):1592-1602. doi: 10.1002/ps.8563. Epub 2024 Nov 26.
Plant pathogenic fungi pose a severe threat to crop yield and food security. This study aims to investigate the potential antifungal activity and mechanism of action of camphor-thiazole derivatives against six plant pathogenic fungi. A novel series of camphor-thiazole derivatives were designed, synthesized and evaluated for their antifungal effects against Rhizoctonia solani, Fusarium graminearum, Valsa mali, Alternaria solani, Colletotrichum orbiculare and Botryitis cinerea.
Most of the synthesized camphor-thiazole derivatives exhibited notable antifungal activity. Amongst them, compounds C5, C10 and C17 showed significant activity against R. solani with median effective concentrations (EC) values in the range 3-4 μg mL, demonstrating superior antifungal efficacy to the control drug boscalid (EC = 1.23 μg mL). Structure-activity relationship and density functional theory analysis emphasized the critical role of substituent selection in optimizing the biological activity of these compounds. Moreover, preliminary mechanistic studies revealed that compound C5 induced abnormal mycelial and cellular morphology in R. solani as observed using scanning and transmission electron microscopy, and triggered the production and accumulation of reactive oxygen species. Additionally, the increased concentration of C5 resulted in enhanced cell membrane permeability.
In this study, the designed and optimized compound C5 emerged as a promising candidate for potent antifungal agents. The results demonstrate that synthesized camphor-thiazole derivatives possess potent antifungal activity and can serve as lead compounds for further optimization in antifungal agent development. © 2024 Society of Chemical Industry.
植物病原真菌对作物产量和粮食安全构成严重威胁。本研究旨在探究樟脑 - 噻唑衍生物对六种植物病原真菌的潜在抗真菌活性及作用机制。设计、合成了一系列新型樟脑 - 噻唑衍生物，并评估了它们对立枯丝核菌、禾谷镰刀菌、苹果腐烂病菌、番茄早疫病菌、瓜炭疽病菌和灰葡萄孢菌的抗真菌效果。
大多数合成的樟脑 - 噻唑衍生物表现出显著的抗真菌活性。其中，化合物C5、C10和C17对立枯丝核菌显示出显著活性，半数有效浓度（EC）值在3 - 4μg/mL范围内，表明其抗真菌效果优于对照药物啶酰菌胺（EC = 1.23μg/mL）。构效关系和密度泛函理论分析强调了取代基选择在优化这些化合物生物活性中的关键作用。此外，初步机理研究表明，使用扫描电子显微镜和透射电子显微镜观察发现，化合物C5会导致立枯丝核菌菌丝和细胞形态异常，并引发活性氧的产生和积累。此外，C5浓度的增加导致细胞膜通透性增强。
在本研究中，设计并优化的化合物C5成为一种有潜力的抗真菌剂候选物。结果表明，合成的樟脑 - 噻唑衍生物具有强大的抗真菌活性，可作为抗真菌剂开发中进一步优化的先导化合物。© 2024化学工业协会。
