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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 12: 4332 - 4338

DOI: https://doi.org/10.6023/cjoc202006056

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

  • Tian Zhongzhen ,
  • Wang Xianhao ,
  • Li Dongmei
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  • 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 date: 2020-06-26

  Revised date: 2020-07-21

  Online 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.

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Abstract

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

Cite this article

Tian Zhongzhen , Wang Xianhao , Li Dongmei . Synthesis, Bioactivities of Novel Neonicotinoid Derivatives Containing 1,2-Dithiocyclopentenone Moiety[J]. Chinese Journal of Organic Chemistry, 2020 , 40(12) : 4332 -4338 . DOI: 10.6023/cjoc202006056

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