Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (12): 4332-4338.DOI: 10.6023/cjoc202006056 Previous Articles     Next Articles


田忠贞, 王先浩, 李冬梅   

  1. 内蒙古科技大学化学与化工学院 内蒙古自治区煤化工与煤炭综合利用重点实验室 内蒙古包头 014010
  • 收稿日期:2020-06-26 修回日期:2020-07-21 发布日期:2020-08-11
  • 通讯作者: 李冬梅
  • 基金资助:

Synthesis, Bioactivities of Novel Neonicotinoid Derivatives Containing 1,2-Dithiocyclopentenone Moiety

Tian Zhongzhen, Wang Xianhao, Li Dongmei   

  1. Inner Mongolia Key Laboratory of Coal Chemical Engineering & Comprehensive Utilization, School of Chemistry and Chemical Engineering, Inner Mongolia University of Science & Technology, Baotou, Mongolia 014010
  • Received:2020-06-26 Revised:2020-07-21 Published:2020-08-11
  • Supported by:
    Project supported by the Natural Science Foundation of Shandong Province (No. ZR2018MB013), the National Natural Science Foundation of China (No. 21501066) and the Opening Project of Shanghai Key Laboratory of Chemical Biology.

In search of novel neonicotinoid insecticides with potent bioactivities, a series of 1,2-dithiocyclopentenone derivatives were designed and synthesized by introducing dithiocyclopentenone into neonicotinoids skeleton. The structures of all compounds were confirmed by nuclear magnetic resonance (NMR) and high resolution mass spectrometry (HRMS). Biological activities of all the title compounds were evaluated systematically. Preliminary bioassays indicated that all synthesized compounds exhibited moderate insecticidal activities. 4-Chloro-5-(((6-chloropyridin-3-yl)methyl)(methyl)amino)-3H-1,2-di-thiol-3-one (3a), 4-chloro-5-(((6-chloropyridin-3-yl)methyl)(ethyl)amino)-3H-1,2-dithiol-3-one (3b), 4-chloro-5-(((6-chloro-pyridin-3-yl)methyl)(propyl)amino)-3H-1,2-dithiol-3-one (3c) and 4-chloro-5-(((6-chloropyridin-3-yl)methyl)(2,2-difluoro-ethyl)amino)-3H-1,2-dithiol-3-one (3g) exhibited >90% mortality rate against Aphis craccivora at 100 μg/mL. Compound 3g exhibited 40% insecticidal activity to aphids at 4 μg/mL and >70% mortality rate against Nilaparvata Lugens at 100 μg/mL, and could be utilized in insecticide research with further optimization.

Key words: neonicotinoid insecticide, dithiocyclopentenone, synthesis, insecticidal activity