Jiang Yangming, An Jiansong, Xia Yu, Fei Qiang, Wang Daoping, Lu Yang, Wu Wenneng
State Key Laboratory for Functions and Applications of Medicinal Plants, Guizhou Medical University Guiyang 550014 China.
School of Food Science and Engineering, Guiyang University Guiyang 550005 China
RSC Adv. 2025 Aug 7;15(34):28084-28092. doi: 10.1039/d5ra04574f. eCollection 2025 Aug 1.
The aim of this study was to design and synthesize 17 novel 1,2,4-triazole thioether derivatives containing 1,3,4-thiadiazole thioether. Bioactivity assays indicated that several target compounds exhibited moderate to good antifungal and antibacterial activities. Notably, compound 9d demonstrated significantly stronger antifungal activity against sp. in (TSM) and sp. in (MSD), with EC values of 9.25 and 12.95 μg mL, respectively, compared to the commercial fungicide pyrimethanil, which had EC values of 35.29 and 15.51 μg mL. Furthermore, compound 9d found to have strong antibacterial activity against pv. (PSA) , with an EC of 9.34 μg mL, markedly superior to that of thiodiazole copper (81.74 μg mL). Additionally, the anti-PSA assessment revealed therapeutic and protective activities at 200 μg mL of 59.39% and 79.33%, respectively, outperforming thiodiazole copper (38.91% and 67.64%, respectively). According to molecular docking simulations the interaction between compound 9d and FtsZ was mainly due to hydrogen bond formations with GLU-296, ARG-301, LYS-188, ASP-29 and GLY-30. This report suggests that these novel 1,2,4-triazole thioether derivatives featuring a 1,3,4-thiadiazole skeleton may effectively mitigate fungal and bacterial threats to plants.
本研究的目的是设计并合成17种含1,3,4-噻二唑硫醚的新型1,2,4-三唑硫醚衍生物。生物活性测定表明，几种目标化合物表现出中等至良好的抗真菌和抗菌活性。值得注意的是，化合物9d对番茄灰霉病菌（TSM）和苹果炭疽病菌（MSD）表现出显著更强的抗真菌活性，其EC值分别为9.25和12.95 μg/mL，相比之下，市售杀菌剂嘧霉胺的EC值分别为35.29和15.51 μg/mL。此外，发现化合物9d对梨火疫病菌（PSA）具有很强的抗菌活性，EC值为9.34 μg/mL，明显优于噻菌铜（81.74 μg/mL）。此外，抗梨火疫病菌评估显示，在200 μg/mL时，其治疗活性和保护活性分别为59.39%和79.33%，优于噻菌铜（分别为38.91%和67.64%）。根据分子对接模拟，化合物9d与FtsZ之间的相互作用主要是由于与GLU-296、ARG-301、LYS-188、ASP-29和GLY-30形成氢键。本报告表明，这些具有1,3,4-噻二唑骨架的新型1,2,4-三唑硫醚衍生物可能有效减轻真菌和细菌对植物的威胁。
