含肟醚和苯氧基吡啶基部分的新型 1,2,4-三唑衍生物的设计、合成和杀菌活性,Molecules

当前位置： X-MOL 学术 › Molecules › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

含肟醚和苯氧基吡啶基部分的新型 1,2,4-三唑衍生物的设计、合成和杀菌活性
Molecules ( IF 4.2 ) Pub Date : 2020-12-11 , DOI: 10.3390/molecules25245852
Hui Bai ₁ , Xuelian Liu ₁ , Pengfei Chenzhang ₁ , Yumei Xiao ₁ , Bin Fu ₁ , Zhaohai Qin ₁

Affiliation

设计并合成了一系列含有肟醚和苯氧基吡啶部分的新型1,2,4-三唑衍生物。新化合物通过核磁共振 (NMR) 光谱和高分辨率质谱 (HRMS) 进行鉴定。化合物 (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-甲基肟 (5a18 ) 通过 X 射线单晶衍射进一步证实。针对八种植物病原体评估了它们的抗真菌活性。体外生物测定表明，大多数标题化合物显示出中度至高度的杀真菌活性。化合物(Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-甲基肟 (5a4) 表现出广谱抗真菌活性，对 S. sclerotiorum, P. 的 EC50 值为 1.59、0.46、0.27 和 11.39 mg/L。infestans、R. solani 和 B. cinerea 分别为。化合物 (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl 肟 (5b2 ) 对核盘菌的 EC50 值最低，为 0.12 mg/L，与商品化的苯醚甲环唑相当。此外，同源建模和分子对接揭示了化合物 5a4 和 5b2 与 CYP51 的可能结合模式。这项工作为发现新的 1,2,4-三唑类杀菌剂提供了有益的指导。同源建模和分子对接揭示了化合物 5a4 和 5b2 与 CYP51 的可能结合模式。这项工作为发现新的 1,2,4-三唑类杀菌剂提供了有益的指导。同源建模和分子对接揭示了化合物 5a4 和 5b2 与 CYP51 的可能结合模式。这项工作为发现新的 1,2,4-三唑类杀菌剂提供了有益的指导。

"点击查看英文标题和摘要"

Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a18) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a4) exhibited a broad-spectrum antifungal activities with the EC50 values of 1.59, 0.46, 0.27 and 11.39 mg/L against S. sclerotiorum, P. infestans, R. solani and B. cinerea, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (5b2) provided the lowest EC50 value of 0.12 mg/L against S. sclerotiorum, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds 5a4 and 5b2 with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.

更新日期：2020-12-11

点击分享查看原文

点击收藏

公开下载

阅读更多本刊新发论文本刊介绍/投稿指南