Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China.
State Key Laboratory of the Discovery and Development of Novel Pesticide (Shenyang Sinochem Agrochemicals R&D Co. Ltd.), Shenyang, 110866, China.
Molecules. 2019 Jul 17;24(14):2607. doi: 10.3390/molecules24142607.
In order to explore more efficient sulfonamides against , 36 novel cyclohexylsulfonamides were synthesized by -(3-dimethylaminopropyl)-'-ethylcarbodiimide (EDCI) and 1-hydroxybenzotriazole (HOBt) condensation reaction using chesulfamide as a lead compound, introducing thiazole and pyrazole active groups. Their structures were characterized by H-NMR, C-NMR, mass spectrum (MS), and elemental analysis. Compound III -31 was further confirmed by X-ray single crystal diffraction. The in vitro and in vivo fungicidal activities against . were evaluated by three bioassay methods. The results of mycelial growth demonstrated that median effective concentration (EC) values of nine compounds were close to boscalid (EC = 1.72 µg/mL) and procymidone (EC = 1.79 µg/mL) against . (KZ-9). In the spore germination experiment, it was found that compounds III-19 and III-31 inhibited germination 93.89 and 98.00%, respectively; at 10 µg/mL, they approached boscalid (95.97%). In the tomato pot experiment, the control effects of two compounds (III-21 and III-27) were 89.80 and 87.90%, respectively, at 200 µg/mL which were significantly higher than boscalid (81.99%). The structure-activity relationship (SAR) was also discussed, which provided a valuable idea for developing new fungicides.
为了探索更有效的磺胺类药物来对抗 ，本文通过 -(3-二甲基氨基丙基)-'-乙基碳化二亚胺 (EDCI) 和 1-羟基苯并三唑 (HOBt) 缩合反应，以 chesulfamide 为先导化合物，引入噻唑和吡唑活性基团，合成了 36 种新型环己基磺胺类化合物。它们的结构通过 H-NMR、C-NMR、质谱 (MS) 和元素分析进行了表征。化合物 III-31 进一步通过 X 射线单晶衍射得到了证实。采用三种生物测定方法评价了它们对. 的体外和体内杀菌活性。菌丝生长结果表明，9 种化合物的中效浓度 (EC) 值接近 boscalid（EC=1.72µg/mL）和 procymidone（EC=1.79µg/mL）对. （KZ-9）的抑制作用。在孢子萌发实验中，发现化合物 III-19 和 III-31 分别抑制萌发 93.89%和 98.00%；在 10µg/mL 时，它们接近 boscalid（95.97%）。在番茄盆栽试验中，两种化合物（III-21 和 III-27）在 200µg/mL 时的防治效果分别为 89.80%和 87.90%，明显高于 boscalid（81.99%）。还讨论了构效关系（SAR），为开发新型杀菌剂提供了有价值的思路。
