Skip to main content
SpringerLink
Log in

Synthesis of 1,3-dithiolane-containing nitromethene compounds and their biological activity as insecticides

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

1,3-Dithiolane-containing nitromethylene derivatives, as candidates for screening as neonicotinoid insecticides, were synthesized by reaction of compound (4) with 1,2-ethanedithiol. Compounds 7a–g were obtained via Mannich reaction of (E)-1-((1,3-dithiolan-2-yl)methyl)-2-(nitromethylene)imidazolidine (6), primary amines and formaldehyde. The synthesized compounds were identified by 1H NMR, IR spectroscopy and elemental analysis. Preliminary bioassays indicated that most of the compounds had moderate insecticidal activity against Aphis craccivora. The relationship between molecular structure and biological activity is discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. M. Williams, S. Arneric, Exp. Opin. Invest. Drugs. 5, 1035 (1996)

    Article  CAS  Google Scholar 

  2. I. Yamamo to, Rev. Toxicol. 2, 61 (1998)

    CAS  Google Scholar 

  3. I. Minamida, K. Iwanaga, T. Tabuchi, I. Aoki, T. Fusaka, H. Ishizuka, T. Okauchi, Nihon. Noyaku. Gakkaishi. 18, 41 (1993)

    Google Scholar 

  4. K. Shiokawa, S. Tsuboi, S. Kagabu, S. Sasaki, K. Moriya, Y. Hattori, Eur. Pat. Appl. EP 235725, 1–59 (1987)

    Google Scholar 

  5. I. Aoki, T. Tabuchi, I. Minamida, Eur. Pat. Appl. EP 381130, 1–34 (1990)

    Google Scholar 

  6. H. Uneme, K. Iwanaga, N. Higuchi, Y. Kando, T. Okauchi, A. Akayama, I. Minamida, Pestic. Sci. 55, 202 (1999)

    Article  CAS  Google Scholar 

  7. K. Moriie, J. Ootsu, Y. Hatsutori, A. Watanabe, A. Ito, Jpn. Pat. JP 07224062, 1–12 (1995)

    Google Scholar 

  8. T. Wakita, K. Kinoshita, E. Yamada, N. Yasui, N. Kawahara, A. Naoi, M. Nakaya, K. Ebihara, H. Matsuno, K. Kodaka, Pest Manag. Sci. 59, 1016 (2003)

    Article  CAS  Google Scholar 

  9. P. Jeschkel, R. Nauen, Pest Manag. Sci. 64, 1084 (2008)

    Article  Google Scholar 

  10. R. Nauen, P. Teschke, L. Copping, Pest Manag. Sci. 64, 1081 (2008)

    Article  CAS  Google Scholar 

  11. I. Yamamoto, G. Yabuta, M. Tomizawa, T. Saito, T. Miyamoto, S. Kagabu, J Pestic. Sci. 20, 33 (1995)

    Article  CAS  Google Scholar 

  12. D. Bai, S. Lummis, W. Leicht, H. Breer, D. Sattelle, Pestic. Sci. 33, 197 (1991)

    Article  CAS  Google Scholar 

  13. M.W. Decker, M.D. Meyer, Biochem. Pharmacol. 58, 917 (1999)

    Article  CAS  Google Scholar 

  14. H. Uneme, J. Agric. Food Chem. 59, 2932 (2011)

    Article  CAS  Google Scholar 

  15. M.Y. Liu, B. Latli, J.E. Casida, Pestic. Biochem. Physiol. 52, 170 (1995)

    Article  CAS  Google Scholar 

  16. K.R. Dahnke, L.A. Paquette, J. Org. Chem. 59, 885 (1994)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank the National Science Foundation China Program (grant 20902037), the Promotive Research Fund for Excellent Young and Middle-aged Scientists of Shandong Province (grant BS2010NY001), and the Opening Fund of Shanghai Key Laboratory of Chemical Biology (grant SKLCB-2008-08).

Author information

Authors and Affiliations

  1. Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, 106 Jiwei Road, Jinan, 250022, People’s Republic of China

    Dongmei Li & Zhongzhen Tian

  2. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, People’s Republic of China

    Zhiping Xu & Gaolei Wang

Authors
  1. Dongmei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhongzhen Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhiping Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Gaolei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhongzhen Tian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Li, D., Tian, Z., Xu, Z. et al. Synthesis of 1,3-dithiolane-containing nitromethene compounds and their biological activity as insecticides. Res Chem Intermed 39, 2063–2070 (2013). https://doi.org/10.1007/s11164-012-0737-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0737-0

Keywords

Search

Navigation