Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2491-2501.DOI: 10.6023/cjoc202004011 Previous Articles     Next Articles

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

汤显军, 鲁星亮, 杨丹, 张敏, 熊永通, 吴清来, 李俊凯   

  1. 长江大学农学院 湖北荆州 434025
  • 收稿日期:2020-04-07 修回日期:2020-04-28 出版日期:2020-08-25 发布日期:2020-05-15
  • 通讯作者: 吴清来, 李俊凯 E-mail:wql106@163.com;junkaili@sina.com
  • 基金资助:
    国家重点研发计划(No.2018YFD200500)和国家自然科学基金(No.31672069)资助项目.

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

Tang Xianjun, Lu Xingliang, Yang Dan, Zhang Min, Xiong Yongtong, Wu Qinglai, Li Junkai   

  1. School of Agriculture, Yangtze University, Jingzhou, Hubei 434025
  • Received:2020-04-07 Revised:2020-04-28 Online:2020-08-25 Published:2020-05-15
  • Supported by:
    Project supported by the National Key Research and Development Program of China (No. 2018YFD200500), and the National Natural Science Foundation of China (No. 31672069).

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.

Key words: phenazine-1-carboxylic acid, fungicidal activity, synthesis, natural product