Skip to main content
SpringerLink
Log in

Synthesis, crystal structure and biological activity of a novel anthranilic diamide insecticide containing allyl ether

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

Abstract

In search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamides containing allyl ether were designed and synthesized. All the compounds were characterized by 1H NMR spectroscopy, HRMS or elemental analysis. The single crystal structure of 18e was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results showed that some compounds exhibited excellent insecticidal activities against Lepidoptera pests. Among this series compounds, 18l showed 100 % larvicidal activity against Mythimna separate Walker and Plutella xylostella Linnaeus at the test concentration.

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
Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. M. Tohnishi, H. Nakao, T. Furuya, A. Seo, H. Kodama, K. Tsubata, S. Fujioka, H. Kodama, T. Hirooka, T. Nishimatsu, J. Pestic. Sci. 30, 354 (2005)

    Article  CAS  Google Scholar 

  2. S.H. Thany, Adv. Exp. Med. Biol. 683, 75 (2010)

    Article  CAS  Google Scholar 

  3. J. Legocki, I. Polec, K. Zelechowski, Contemporary trends in development of active substances possessing the pesticidal properties: spinosyn insecticides. Pestycydy/Pesticides 1–4, 59–71 (2010)

    Google Scholar 

  4. R. Coronado, J. Morrissette, M. Sukhareva, D.M. Vaughan, Am. J. Physiol. 266, 1485 (1994)

    Google Scholar 

  5. D.B. Sattelle, D. Cordova, T.R. Cheek, Invert. Neurosci. 8, 107 (2008)

    Article  CAS  Google Scholar 

  6. M. Tohnishi, T. Nishimatsu, K. Motoba, T. Hirooka, S. Akira, J. Pestic. Sci. 35, 508 (2010)

    Article  Google Scholar 

  7. M. Tohnishi, H. Nakao, E. Kohno, T. Nishida, T. Furuya, T. Shimizu, A. Seo, K. Sakata, S. Fujioka, H. Kanno, Euro Patent 919542

  8. M. Tohnishi, H. Nakao, E. Kohno, T. Nishida, T. Furuya, T. Shimizu, A. Seo, K. Sakata, S. Fujioka, H. Kanno, Euro Patent 1006107

  9. G.P. Lahm, T.P. Selby, J.H. Freudenberger, T.M. Stevenson, B.J. Myers, G. Seburyamo, B.K. Smith, L. Flexner, C.E. Clark, D. Cordova, Bioorg. Med. Chem. Lett. 15, 4898 (2005)

    Article  CAS  Google Scholar 

  10. G.P. Lahm, T.M. Stevenson, T.P. Selby, J.H. Freudenberger, D. Cordova, L. Flexner, C.A. Bellin, C.M. Dubas, B.K. Smith, K.A. Hughes, J.G. Hollingshaus, C.E. Clark, E.A. Benner, Bioorg. Med. Chem. Lett. 17, 6274 (2007)

    Article  CAS  Google Scholar 

  11. G.P. Lahm, B.J. Myers, T.P. Selby, T.M. Stevenson, WO Patent 2001070671

  12. G.P. Lahm, T.P. Selby, T.M. Stevenson, WO Patent 2003015519

  13. X.H. Liu, W.G. Zhao, B.L. Wang, Z.M. Li, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0521-1

  14. G.P. Lahm, D. Cordova, J.D. Barry, Bioorg. Med. Chem. Lett. 17, 4127 (2009)

    Article  CAS  Google Scholar 

  15. X.L. Tong, Z.S. Ren, X.L. Qu, Q.W. Yang, W.Q. Zhang, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0517-x

  16. K.A. Hughes, G.P. Lahm, T.P. Selby, WO Patent 2004046129

  17. G.P. Lahm, T.P. Selby, T.M. Stevenson, WO Patent 2004033468

  18. T.C. Lai, J.Y. Su, J. Pestic. Sci. 84, 381 (2011)

    Article  Google Scholar 

  19. P.L. George, P.S. Thomas, WO Patent 2003026415

  20. W.L. Dong, J.Y. Xu, X.H. Liu, Z.M. Li, B.J. Li, Y.X. Shi, Chem. J. Chin. Univ. 29, 1990 (2008)

    CAS  Google Scholar 

  21. G.M. Sheldrick, SHELXS97 and SHELXL97 (University of Göttingen, Germany, 1997)

    Google Scholar 

  22. Y. Luo, G. Yang, Bioorg. Med. Chem. 15, 1716 (2007)

    Article  CAS  Google Scholar 

  23. Y. Wang, X. Ou, H. Pei, X. Lin, K. Yu, Agrochem. Res. Appl. 10, 20 (2006)

    Google Scholar 

  24. X.H. Liu, L. Pan, C.X. Tan, J.Q. Weng, B.L. Wang, Z.M. Li, Pestic. Biochem. Physiol. 101, 143 (2011)

    Article  CAS  Google Scholar 

  25. Y.L. Xue, Y.G. Zhang, X.H. Liu, Asian J. Chem. 24, 3016 (2012)

    CAS  Google Scholar 

  26. X.H. Liu, L. Pan, J.Q. Weng, C.X. Tan, Y.H. Li, B.L. Wang, Z.M. Li, Mol. Divers. 16, 251 (2012)

    Article  CAS  Google Scholar 

  27. C.X. Tan, J.Q. Weng, Z.X. Liu, X.H. Liu, W.G. Zhao, Phosphorus Sulfur Silicon Relat. Elem. 187, 990 (2012)

    Article  CAS  Google Scholar 

  28. X.H. Liu, J.Q. Weng, C.X. Tan, H.J. Liu, Acta Crystallogr. E67, o493 (2011)

    Google Scholar 

  29. X.H. Liu, C.X. Tan, J.Q. Weng, Phosphorus Sulfur Silicon Relat. Elem. 186, 558 (2011)

    Article  CAS  Google Scholar 

  30. X.F. Liu, X.H. Liu, Acta Crystallogr. E 67, o202 (2011)

    Article  CAS  Google Scholar 

  31. P.Q. Chen, C.X. Tan, J.Q. Weng, X.H. Liu Asian, J. Chem. 24, 2808 (2012)

    CAS  Google Scholar 

  32. Y.L. Xue, Y.G. Zhang, X.H. Liu, Asian J. Chem. 24, 1571 (2012)

    CAS  Google Scholar 

  33. H.J. Liu, J.Q. Weng, C.X. Tan, X.H. Liu, Acta Crystallogr. E67, o1940 (2011)

    Google Scholar 

  34. Y.L. Xue, Y.G. Zhang, X.H. Liu, Asian J. Chem. 24, 5087 (2012)

    CAS  Google Scholar 

  35. X.H. Liu, L. Pan, Y. Ma, J.Q. Weng, C.X. Tan, Y.H. Li, Y.X. Shi, B.J. Li, Z.M. Li, Y.G. Zhang, Chem. Biol. Drug Des. 78, 689 (2011)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Basic Research Program of China (No. 2010CB126106), the Fundamental Research Funds for the Central Universities for the financial support (Grant BE018201) and the Specialized Research Fund for the Doctoral Program of Higher Education (20110031120011).

Author information

Authors and Affiliations

  1. State Key Laboratory of Elemento-Organic Chemistry, National Pesticidal Engineering Centre (Tianjin), Nankai University, Tianjin, 300071, China

    Yu Zhao, Li-xia Xiong, Li-ping Xu, Hongxue Wang, Han Xu, Hua-bin Li, Jun Tong & Zheng-ming Li

Authors
  1. Yu Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Li-xia Xiong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Li-ping Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hongxue Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Han Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hua-bin Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jun Tong
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Zheng-ming Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zheng-ming Li.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhao, Y., Xiong, Lx., Xu, Lp. et al. Synthesis, crystal structure and biological activity of a novel anthranilic diamide insecticide containing allyl ether. Res Chem Intermed 39, 3071–3088 (2013). https://doi.org/10.1007/s11164-012-0820-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0820-6

Keywords

Search

Navigation