Chen Cai-Yun, He Hong-Wei, Xu Dan, Lin Guo-Tai, Li Yantao, Zhou Huan, Liu Xili, Xu Gong
Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi, China.
Institute of Cotton Research, Shanxi Agricultural University, Yuncheng 044000, Shanxi, China.
J Agric Food Chem. 2025 Jan 8;73(1):147-158. doi: 10.1021/acs.jafc.4c07402. Epub 2024 Dec 26.
The γ-butyrolactone scaffold, commonly present in natural products and bioactive compounds, has played a crucial role in the development of novel pesticides. In this study, a series of α-methylene-γ-butyrolactone derivatives containing a diphenyl ether moiety were designed and synthesized using the scaffold splicing strategy. Bioassays revealed that several target compounds demonstrated potent fungicidal activities, particularly against and . Notably, compound (EC = 0.809 mg/L) exhibited the highest antioomycete activity against , outperforming (EC = 41.0 mg/L) but being less effective than (EC = 0.180 mg/L). Meanwhile, compound (EC = 1.47 mg/L) showed the strongest antifungal activity against , which was higher than those of (EC = 1.80 mg/L) and (EC = 13.6 mg/L). experiments confirmed that compound has satisfactory protective and curative effects against , which were better than those of . Additionally, compound was found to inhibit sporangia formation, zoospore release, and cystospore germination of at 10 mg/L. Physiological and biochemical studies indicated that compound can induce changes in the mycelial morphology of , increase cell membrane permeability, and modulate respiratory metabolism. Furthermore, both enzymatic inhibition assays and molecular docking analysis suggested that the primary mechanism of action of compound may involve binding to complex III on the respiratory chain. This work provides valuable insights for the development of α-methylene-γ-butyrolactone derivatives incorporating a diphenyl ether moiety as novel agricultural fungicidal agents.
γ-丁内酯骨架常见于天然产物和生物活性化合物中，在新型农药的开发中发挥了关键作用。在本研究中，采用骨架拼接策略设计并合成了一系列含有二苯醚部分的α-亚甲基-γ-丁内酯衍生物。生物测定表明，几种目标化合物表现出强效的杀菌活性，尤其是对[具体对象1]和[具体对象2]。值得注意的是，化合物[具体编号1]（EC = 0.809 mg/L）对[具体对象1]表现出最高的抗卵菌活性，优于[对比化合物1]（EC = 41.0 mg/L），但比[对比化合物2]（EC = 0.180 mg/L）效果稍差。同时，化合物[具体编号2]（EC = 1.47 mg/L）对[具体对象2]表现出最强的抗真菌活性，高于[对比化合物3]（EC = 1.80 mg/L）和[对比化合物|4]（EC = 13.6 mg/L）。[实验名称]实验证实，化合物[具体编号2]对[具体对象2]具有令人满意的保护和治疗效果，优于[对比化合物5]。此外，发现化合物[具体编号2]在10 mg/L时可抑制[具体对象2]的孢子囊形成、游动孢子释放和厚壁孢子萌发。生理生化研究表明，化合物[具体编号2]可诱导[具体对象2]菌丝形态变化，增加细胞膜通透性，并调节呼吸代谢。此外，酶抑制试验和分子对接分析均表明，化合物[具体编号2]的主要作用机制可能涉及与呼吸链上的复合物III结合。这项工作为开发含有二苯醚部分的α-亚甲基-γ-丁内酯衍生物作为新型农用杀菌剂提供了有价值的见解。
