背景:病原真菌感染的植物病害对全球农业和食品工业的产量具有破坏性影响。小说的发展,环保,高效杀菌剂是防治植物病原真菌的重要技术。
结果:这里,99硫基含羟基衍生物,亚砜,砜,羰基,双键,氨基,亚胺,肟,肟酯,和酰胺部分被合成。还研究了目标化合物对10种典型的植物病原真菌的抗真菌活性。生物测定结果表明,大多数目标化合物在体外对所测试的真菌表现出中等至优异的抗真菌作用。其中,硫色满肟衍生物(12a-12m)发挥了有希望的抑制作用,特别是对镰刀菌,禾谷镰刀菌,ValsaMali,和灰葡萄孢菌菌株。此外,化合物12f和12g显著抑制孢子萌发胚芽和试管生长。同时,它们对被F.solani感染的马铃薯发挥了极好的保护作用,使它们优于商业杀菌剂Hymexazol和百菌清。值得注意的是,化合物12d和12f对被灰霉病菌感染的樱桃番茄也表现出优异的保护作用。进一步的机理研究表明,化合物12f通过明显改变菌丝体结构并显着增加细胞膜通透性而发挥抗真菌作用。幸运的是,优良的生物活性化合物对人类肝细胞系(WRL-68)具有良好的安全性.初步的结构-活性关系分析表明,在硫代吡喃环上引入羟基或肟片段可能对抗真菌活性显着有益。
结论:本研究提供了可用于开发用于植物病原真菌管理的新型植物杀真菌剂的硫色满化合物。©2024化学工业学会。
BACKGROUND: Plant diseases infected by pathogenic fungi have a devastating effect on global agricultural and food industry yields. The development of novel, environmentally friendly, and efficient fungicides is an important technique for preventing and combatting phytopathogenic fungi.
RESULTS: Herein, 99 thiochroman-based derivatives containing hydroxyl, sulfoxide, sulfone, carbonyl, double bond, amino, imine, oxime, oxime ester, and amide moieties were synthesized. The antifungal activities of the target compounds against ten typical phytopathogenic fungi were also investigated. The bioassay results illustrated that most of the target compounds exhibited moderate to excellent antifungal effects against the tested fungi in vitro. Among these, thiochroman-oxime derivatives (12a-12m) exerted a promising inhibition effect, especially against Fusarium solani, Fusarium graminearum, Valsa mali, and Botrytis cinerea strains. Furthermore, the compounds 12f and 12g markedly suppressed the spore germination germ and tube growth. At the same time, they exerted excellent protective effects against potatoes infected by F. solani, making them superior to commercial fungicides Hymexazol and Chlorothalonil. Notably, the compounds 12d and 12f also showed excellent protective effects against cherry tomatoes infected by B. cinerea. Further mechanistic studies revealed that compound 12f exerted an antifungal effect by overtly altering the mycelium structure and remarkably increasing cell membrane permeability. Fortunately, the excellent bioactive compounds showed good safety against human hepatic cell lines (WRL-68). The preliminary structure-activity relationship analysis revealed that the introduction of hydroxyl or oxime fragments at the thiopyran ring might be significantly beneficial to antifungal activity.
CONCLUSIONS: This study provides thiochroman compounds that can be used in the development of novel botanical fungicides for the management of phytopathogenic fungi. © 2024 Society of Chemical Industry.