Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, College of Plant Protection, Northwest A&F University, Yangling, China.
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, China.
Pest Manag Sci. 2023 Dec;79(12):5015-5028. doi: 10.1002/ps.7703. Epub 2023 Aug 24.
Plant diseases caused by phytopathogenic fungi and oomycetes pose a serious threat to ensuring crop yield and quality. Finding novel fungicidal candidates based on natural products is one of the critical methods for developing effective and environmentally friendly pesticides. In this study, a series of salicylaldehyde derivatives containing an α-methylene-γ-butyrolactone moiety were designed, synthesized, and their fungicidal activities were evaluated.
The bioassay studies indicated that compound C3 displayed an excellent in vitro activity against Rhizoctonia solani with a half-maximal effective concentration (EC ) value of 0.65 μg/mL, higher than that of pyraclostrobin (EC = 1.44 μg/mL) and comparable to that of carbendazim (EC = 0.33 μg/mL). For Valsa mali and Phytophthora capsici, compound C3 also showed good fungicidal activities with EC values of 0.91 and 1.33 μg/mL, respectively. In addition, compound C3 exhibited promising protective in vivo activity against R. solani (84.1%) at 100 μg/mL, which was better than that of pyraclostrobin (78.4%). The pot experiment displayed that compound C3 had 74.8% protective efficacy against R. solani at 200 μg/mL, which was comparable to that of validamycin (78.2%). The antifungal mode of action research indicated that compound C3 could change the mycelial morphology and ultrastructure, increase cell membrane permeability, affect respiratory metabolism by binding to complex III, and inhibit the germination and formation of sclerotia, thereby effectively controlling the disease.
The present study provides support for the application of these salicylaldehyde derivatives as promising potential pesticides with remarkable and broad-spectrum fungicidal activities against phytopathogenic fungi and oomycetes in crop protection. © 2023 Society of Chemical Industry.
由植物病原菌真菌和卵菌引起的植物病害严重威胁着作物产量和质量的保障。基于天然产物寻找新型杀菌候选物是开发有效和环保农药的关键方法之一。在本研究中，设计、合成了一系列含有α-亚甲基-γ-丁内酯部分的水杨醛衍生物，并评价了它们的杀菌活性。
生物测定研究表明，化合物 C3 对腐霉属（Rhizoctonia solani）表现出优异的体外活性，半效有效浓度（EC ）值为 0.65μg/mL，高于吡唑醚菌酯（EC = 1.44μg/mL），与多菌灵（EC = 0.33μg/mL）相当。对于苹果腐烂病菌（Valsa mali）和辣椒疫霉（Phytophthora capsici），化合物 C3 也表现出良好的杀菌活性，EC 值分别为 0.91 和 1.33μg/mL。此外，化合物 C3 在 100μg/mL 时对腐霉属（R. solani）具有良好的体内保护活性（84.1%），优于吡唑醚菌酯（78.4%）。盆栽试验表明，化合物 C3 在 200μg/mL 时对腐霉属的保护效果为 74.8%，与戊唑醇（78.2%）相当。抑菌作用方式研究表明，化合物 C3 可以改变菌丝形态和超微结构，增加细胞膜通透性，通过与复合物 III 结合影响呼吸代谢，抑制菌核的萌发和形成，从而有效控制病害。
本研究为这些水杨醛衍生物作为具有显著和广谱杀菌活性的潜在农药应用于作物保护提供了支持，对防治植物病原菌真菌和卵菌具有重要意义。 © 2023 化学工业协会。
