Li Ding, Yao Xiaofang, Wang Wei-Wei, Wang Yu, Wu Wenjun, Hu Zhaonong
Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, Northwest A&F University, Yangling, P. R. China.
Key Laboratory for Botanical Pesticide R&D of Shaanxi Province, Institute of Pesticide Science, Northwest A&F University, Yangling, P. R. China.
Pest Manag Sci. 2025 Apr;81(4):1909-1922. doi: 10.1002/ps.8591. Epub 2024 Dec 4.
The potential application of vanillin as a fungicide has garnered significant attention in the agricultural product market and food industries. Consequently, a novel series of vanillin derivatives containing thiazole and hydrazone fragments were strategically designed, synthesized, and evaluated for their antifungal activity against six representative plant phytopathogenic fungi.
In the in vitro antifungal assay, some title vanillin derivatives showed good antifungal activity against Botrytis cinerea, Fusarium solani, and Magnaporthe grisea. Significantly, compound 4a exhibited remarkable broad-spectrum fungistatic potency and displayed the most potent antifungal activity against B. cinerea and F. solani, with half maximal effective concentration (EC) values of 1.07 and 0.78 μg/mL, respectively, substantially surpassing the efficacy of the commercial fungicide hymexazol and comparable to carbendazim. In addition, compound 4k selectively inhibited M. grisea with the lowest EC value of 7.77 μg/mL. The in vivo antifungal assay revealed that compound 4a exhibited superior protective efficacy against B. cinerea compared to carbendazim. At the same time, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and fluorescent dye staining showed compound 4a exerted its fungicidal activity by damaging the cell wall, cell membrane and mitochondria of B. cinerea.
Modification of vanillin through electron-withdrawing group substitution and hydrophobic substitution, followed by condensation with thiazole-4-carbohydrazide, could result in highly active antifungal derivatives. Among them, compound 4a, which exhibited excellent inhibitory activities in vitro and in vivo, could potentially serve as a lead compound. © 2024 Society of Chemical Industry.
香兰素作为一种杀菌剂的潜在应用在农产品市场和食品工业中引起了广泛关注。因此，我们有针对性地设计、合成了一系列含有噻唑和腙片段的新型香兰素衍生物，并对其针对六种代表性植物病原真菌的抗真菌活性进行了评估。
在体外抗真菌试验中，一些目标香兰素衍生物对灰葡萄孢菌、茄丝核菌和稻瘟病菌表现出良好的抗真菌活性。值得注意的是，化合物4a表现出显著的广谱抑菌效力，对灰葡萄孢菌和茄丝核菌的抗真菌活性最强，其半数有效浓度（EC）值分别为1.07和0.78μg/mL，大大超过了商业杀菌剂恶霉灵的功效，与多菌灵相当。此外，化合物4k对稻瘟病菌具有选择性抑制作用，最低EC值为7.77μg/mL。体内抗真菌试验表明，与多菌灵相比，化合物4a对灰葡萄孢菌具有更好的保护效果。同时，扫描电子显微镜（SEM）、透射电子显微镜（TEM）和荧光染料染色显示，化合物4a通过破坏灰葡萄孢菌的细胞壁、细胞膜和线粒体发挥其杀菌活性。
通过吸电子基团取代和疏水取代对香兰素进行修饰，然后与噻唑-4-碳酰肼缩合，可以得到高活性的抗真菌衍生物。其中，化合物4a在体外和体内均表现出优异的抑制活性，有望作为先导化合物。©2024化学工业协会。
