Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2206-2216.DOI: 10.6023/cjoc202208027 Previous Articles     Next Articles


王余, 陈艺方, 罗鑫, 邢志富, 彭菊, 陈吉祥*()   

  1. 贵州大学绿色农药与农业生物工程国家重点实验室培育基地 教育部绿色农药与农业生物工程重点实验室 贵阳 550025
  • 收稿日期:2022-08-20 修回日期:2022-10-03 发布日期:2022-12-21
  • 基金资助:
    贵州省自然科学基金(QKHJC-ZK[2022]039); 贵州大学自然科学基金((2021)01)

Design, Synthesis and Nematicidal Activity of Novel 2-Cyanoacrylate (Amide) Derivatives

Yu Wang, Yifang Chen, Xin Luo, Zhifu Xing, Ju Peng, Jixiang Chen*()   

  1. Key Laboratory of Green Pesticide and Agricultural Bioengineering, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025
  • Received:2022-08-20 Revised:2022-10-03 Published:2022-12-21
  • Contact: E-mail:
  • Supported by:
    Natural Science Foundation of Guizhou Province(QKHJC-ZK[2022]039); Natural Science Foundation of Guizhou University((2021)01)

To find novel and efficient nematicides, 28 2-cyanoacrylate (amide) derivatives were designed and synthesized. The structures of all target compounds were confirmed by 1H NMR, 13C NMR, and high-resolution mass spectra (HRMS). The configuration of ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate (3f) was confirmed by X-ray single crystal diffraction. The results of nematicidal activities test showed that all the target compounds had certain nematicidal activities against Meloidogyne incognita, Aphelenchoides besseyi, and Ditylenchus destructor (second-stage juveniles) after 72 h of treatment at 100 mg/L. Among them, the LC50s of ethyl (E)-2-cyano-3-(4-fluorophenyl)acrylate (3i) and ethyl (E)-2-cyano-3-(furan-2-yl)- acrylate (3n) against Meloidogyne incognita for 72 h were 24.58 and 32.13 mg/L, respectively. The LC50s of ethyl (E)-3-(4-(2- ((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)ethoxy)phenyl)-2-cyanoacrylate (17a) against A. besseyi and D. destructor were 31.97 and 38.26 mg/L, respectively, which were significantly better than that of the control agent Tioxazafen (48.95 and 74.95 mg/L). In addition, compound 3i could significantly promote the production of reactive oxygen species (ROS) and the accumulation of lipofuscin and lipid in M. incognita, which indicated that compound 3i might promote oxidative stress of M. incognita and eventually lead to the death of nematodes. Compound 3i can be used as a lead compound to develop novel nematicides.

Key words: 2-cyanoacrylate, amide, nematicidal activity, Meloidogyne incognita, Aphelenchoides besseyi, Ditylenchus destructor, oxidative stress