Get access

Design, synthesis and insecticidal activity of novel 1,1-dichloropropene derivatives

Authors

  • Jun Li,

    1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
    Search for more papers by this author
  • Zhen-Yu Wang,

    1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
    Search for more papers by this author
  • Qiong-You Wu,

    1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
    Search for more papers by this author
  • Guang-Fu Yang

    Corresponding author
    1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China
    2. Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin, China
    • Correspondence to: Guang-Fu Yang, Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China. E-mail: gfyang@mail.ccnu.edu.cn

    Search for more papers by this author

Abstract

BACKGROUND

Pyridalyl is a highly active insecticide against lepidopterous larvae, with a novel chemical structure not related to any other existing insecticide. To discover new pyridalyl analogues with high activity against resistant pests, a series of 1,1-dichloropropene derivatives bearing structurally diverse substituted heterocycle rings in place of the pyridine ring of pyridalyl were designed and synthesised.

RESULTS

All of the title compounds were confirmed by 1H NMR, 13C NMR and high-resolution mass spectra. Two representative compounds (Ic and IIa) were further characterised by X-ray diffraction analysis. In addition, bioassays showed that most of the newly synthesised compounds displayed good insecticidal activity against Prodenia litura. Further determination of LD50 values and field trials identified compound IIa as the most promising candidate, which produced a much better 14 day control effect against diamondback moths and longer duration of efficacy than pyridalyl, indicating its potential for further development as a new insecticide for the control of lepidopteran insects.

CONCLUSION

Compound IIa has great potential for further development as a new insecticide for the control of lepidopteran insects. © 2014 Society of Chemical Industry

Ancillary