Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3116-3125.DOI: 10.6023/cjoc202103021 Previous Articles     Next Articles



许庆博, 梁培博, 路慧哲, 金淑惠*(), 董燕红, 张建军*()   

  1. 中国农业大学理学院 北京 100193
  • 收稿日期:2021-03-10 修回日期:2021-04-07 发布日期:2021-06-02
  • 通讯作者: 金淑惠, 张建军
  • 基金资助:
    国家重点研发计划(2018YFD0200100); 国家自然科学基金(21772230)

Design, Synthesis and Bioactivity of Fluopyram Derivatives Containing Diamide Moiety

Qingbo Xu, Peibo Liang, Huizhe Lu, Shuhui Jin(), Yanhong Dong, Jianjun Zhang()   

  1. College of Science, China Agricultural University, Beijing 100193
  • Received:2021-03-10 Revised:2021-04-07 Published:2021-06-02
  • Contact: Shuhui Jin, Jianjun Zhang
  • Supported by:
    National Key R&D Program of China(2018YFD0200100); National Natural Science Foundation of China(21772230)

According to the principle of combination of bioactive substructure, the structure of diamide was introduced into fluopyram, and 22 novel fluopyram derivatives containing diamide were designed and synthesized. The structures of the target compounds were characterized by 1H NMR, 13C NMR and HRMS. The inhibitory activities of the target compounds against four plant pathogenic fungi and in vitro insecticidal activities against Caenorhabditis elegans were studied. The results showed that under the concentration of 50 mg/L, most of the compounds showed moderate fungicide activity against Cytospora sp. and Sclerotinia sclerotiorum with inhibition rate over 80%. The EC50 of N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl)- 2-(3-fluorobenzamido)benzamide (7f) to Cytospora sp. was 6.12 mg/L, which is higher than fluopyram (35.5 mg/L), the SDH essay showed that enzyme inhibition rate of 7f reached 90.1%, and the mortality rate against C. elegans was 87% at 200 mg/L. The results of molecular docking show that the SDH may be a potential target of the compounds.

Key words: succinate dehydrogenase, nematicide, diamide, fluopyram