Discovery of novel D/L-camphor derivatives containing oxime ester as fungicide candidates: Antifungal activity, structure-activity relationship and preliminary mechanistic study

作者：Peng Dai, Zihua Ma, Huizhen Xue, Kaili Xie, Yufei Li, Yafang Sun, Qing Xia, Ming‐Zhi Zhang, Yu‐Cheng Gu, Weihua Zhang · 发表于：Advanced Agrochem · 年份：2024 · DOI：10.1016/j.aac.2024.11.007 · 被引用次数：14 · 研究领域：Fungal Plant Pathogen Control、Synthesis and biological activity、Pesticide and Herbicide Environmental Studies

To develop new environmentally friendly fungicides, we designed and synthesized a novel series of D/L-configured camphor oxime ester derivatives based on the natural product camphor as a lead compound. We investigated the in vitro antifungal activity of these compounds against six common plant pathogenic fungi. Among them, compounds B1-6, B1-17 and B2-6 displayed great in vitro activity against Rhizoctonia solani with EC 50 values of 7.28, 4.64, and 7.62 μg/mL. The HOMO and LUMO calculations indicated that strong electron-withdrawing halogen elements exhibit better activity compared to electron-donating alkyl groups. Preliminary mechanistic studies, using SEM and TEM, indicated that compound B1-17 induced disordered entanglement of hyphae, shrinkage of hyphal surfaces, and vacuole swelling and rupture, which disrupted normal hyphal growth. Additionally, compound B1-17 induced the production and accumulation of ROS, disrupted MMP, and effectively inhibited the germination and formation of sclerotia in Rhizoctonia solani . These compounds hold potential as new antifungal agents for further research. • A series of novel camphor derivatives were designed and synthesized. • Some compounds showed excellent antifungal activity in primary assays. • R. solani cells treated with B1-17 showed abnormal ultrastructure. • HOMO and LUMO used to explore structure-activity relationships of these derivatives. • Highly active compounds analyzed by ROS, MMP, SEM, and TEM.