基于吩嗪-1-羧酸的新型麦角甾醇生物合成抑制剂叔醇类衍生物的合成及杀菌活性研究  

Synthesis and Fungicidal Activities of Novel Tertiary Alcohol Ergosterol Biosynthesis Inhibitors Based on Phenazine-1-carboxylic Acid

作　　者：汤显军 鲁星亮 杨丹 张敏[1] 熊永通 吴清来[1] 李俊凯[1] Tang Xianjun;Lu Xingliang;Yang Dan;Zhang Min;Xiong Yongtong;Wu Qinglai;Li Junkai(School of Agriculture,Yangtze University,Jingzhou,Hubei 434025)

机构地区：[1]长江大学农学院,湖北荆州434025

出　　处：《有机化学》2020年第8期2491-2501,共11页Chinese Journal of Organic Chemistry

基　　金：国家重点研发计划(No.2018YFD200500);国家自然科学基金(No.31672069)资助项目.

摘　　要：在前期以天然产物吩嗪-1-羧酸为先导化合物进行新农药的开发研究中发现,吩嗪-1-甲醇具有优异的杀菌活性.基于上述发现,通过将吩嗪-1-甲醇作为次级先导化合物,并结合麦角甾醇生物合成抑制剂氯苯嘧啶醇,设计并合成了16个吩嗪-1-芳基(5-嘧啶)甲醇衍生化合物.杀菌测试表明部分目标化合物对水稻纹枯病及辣椒疫病表现出中等抑制活性.有趣的是大多数目标化合物对抗吩嗪-1-羧酸特征性杀菌谱水稻纹枯病活性是显著下降的;而对于抗氯苯嘧啶醇特征性杀菌谱小麦白粉病(Erysiphe graminis)表现出中等以上的杀菌活性.这表明目标化合物的作用机制可能不同于吩嗪-1-羧酸,但相似于氯苯嘧啶醇.进一步的麦角甾醇生物合成抑制实验证明了目标化合物的作用方式与氯苯嘧啶醇相同.During our previous research using natural product phenazine-1-carboxylic acid as the lead compound to develop new pesticides,the phenazine-1-methanol had been found to exhibit excellent fungicidal activity.According to the above fact,a new class of phenazine-1-aryl(5-pyrimidine)methanol derivatives were designed and synthesized by using phenazine-1-methanol as a secondary lead compound,and referring to ergosterol biosynthesis inhibitor fenarimol.The bio-assays showed that compounds 6a^6p displayed moderate fungicidal activities against Thanatephorus cucumeris and Phytophthora capsici.An interesting result is that the fungicidal activities of some of the target compounds against Phenazine-1-carboxylic-Acid(PCA)specific spectrum Thanatephorus cucumeris are greatly reduced,while against fenarimol characteristic spectrum wheat powdery mildew(Erysiphe graminis)retain moderate or strong control effects.The above bio-assays results indicated the mode of action of compounds 6a^6p may be different from that of PCA,but similar to fenarimol.Therefore,further ergosterol biosynthesis inhibition experiment proved that the target compounds had the same mode of action as commercially available fungicide fenarimol.

关 键 词：吩嗪-1-羧酸 杀菌活性 合成 天然产物 

分 类 号：TQ455.4[化学工程—农药化工]