N-((5-烷硫基-1,3,4-噁二唑)-2-基)甲基溴代吡咯腈的合成及生物活性

为了发现农药活性的新化合物，以溴代吡咯腈为原料，通过亲核取代、肼解和成环等反应，设计合成了一系列N-((5-烷硫基-1,3,4-噁二唑)-2-基)甲基溴代吡咯腈目标化合物( 5a ~ 5t )，所有化合物的结构均得到核磁共振氢谱和高分辨质谱确证。杀菌活性测定结果显示:在浓度为0.20 mmol/L时，大部分目标化合物具有一定的抑菌活性，其中化合物 5h 对水稻稻瘟病菌Magnaporthe oryzae的抑制率为60.07%，优于对照药剂咯菌腈(58.21%)。杀虫与杀螨活性测定结果显示:在浓度为0.20 mmol/L时，大部分目标化合物对斜纹夜蛾Spodoptera litura和朱砂叶螨Tetranychus cinnabarinus雌成螨具有一定的杀虫和杀螨活性，但均低于对照药剂虫螨腈(100%)。杀线虫生物测定结果显示:在浓度为0.20 mmol/L时，大部分目标化合物表现出优异的杀线虫活性，其中化合物 5k 、 5r 和 5s 对秀丽隐杆线虫Caenorhabditis elegans的LC₅₀值分别为0.0918、0.0733和0.0810 mmol/L，优于对照药剂噻唑膦(0.2798 mmol/L)。本研究所合成的目标化合物具有一定的杀菌、杀虫、杀螨和杀线虫活性，可为溴代吡咯腈衍生物的设计和合成提供参考。

Synthesis and biological activity of N-((5-alkylthio-1,3,4-oxadiazole)-2-ylmethyl) tralopyril

In order to find new compounds with pesticide activity, a series of N-((5-alkylthio-1,3,4-oxadiazole)-2-methyl) tralopyril were designed and synthesized from tralopyril by nucleophilic substitution, hydrazinolysis and cyclization. The structures of these derivatives were confirmed by 1H NMR and HRMS. The test against 5 pathogenic fungi showed that most of the target compounds had certain fungicidal activity at the concentration of 0.20 mmol/L, and the inhibitory rate of compound 5h against Magnaporthe oryzae was 60.07%, which was better than that of the control agent fludioxonil (58.21%). The results of insecticidal and acaricidal activities showed that at the concentration of 0.20 mmol/L, some of the target compounds had certain insecticidal and acaricidal activities against Spodoptera litura and adult mite of Tetranychus cinnabarinus, while all were lower than the control agent chlorfenapyr (100%). The results of nematicidal activity showed that most of the compounds exhibited excellent nematicidal activity at the concentration of 0.20 mmol/L. The LC₅₀ values of compounds 5k, 5r and 5s against Caenorhabditis elegans were 0.0918, 0.0733, 0.0810 mmol/L respectively, which were better than the control agent fosthiazate (0.2798 mmol/L). The target compounds synthesized in this study have certain fungicidal, insecticidal, acaricidal and nematicidal activities, which can provide a reference for the design and synthesis of tralopyril derivatives.