Skip to main content
SpringerLink
Log in

Synthesis and antifungal activity of novel 1-(1H-benzoimidazol-1-yl)propan-2-one oxime-ethers containing the morpholine moiety

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

Abstract

A series of 1-(2-(4-morpholinomethyl)-1H-benzoimidazol-1-yl)propan-2-one oxime-ethers have been synthesized from 2-chloromethyl-1H-benzoimidazole, morpholine, bromoacetone, hydroxylamine, and a haloalkane (or benzyl halide). Their structures were elucidated by IR, 1H NMR, elemental analysis, and MS. Antifungal activity against Botrytis cinerea, Sclerotinia sclerotiorum, and Beans sclerotia was evaluated by the mycelium growth-rate method; the results indicated that many of the target compounds have excellent antifungal activity, even higher than that of the control fungicide (carbendazim).

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

Similar content being viewed by others

References

  1. A. Mobinikhaledi, N. Foroughifar, M. Kalhor, M. Mirabolfathy, J. Heterocyclic Chem. 47, 77–80 (2010)

    CAS  Google Scholar 

  2. L. Keurulainen, O. Salin, A. Siiskonen, J.M. Kern, J. Alvesalo, P. Kiuru, M. Maass, J. Yli-Kauhaluoma, P. Vuorela, J. Med. Chem. 53, 7664–7674 (2010)

    Article  CAS  Google Scholar 

  3. F. Xue, X.J. Luo, C.H. Ye, W.D. Ye, Y. Wang, Bioorg. Med. Chem. 19, 2641–2649 (2011)

    Article  CAS  Google Scholar 

  4. S. Demirayak, I. Kayagil, L. Yurttas, Eur. J. Med. Chem. 46, 411–416 (2011)

    Article  CAS  Google Scholar 

  5. A.A. Farahat, E. Paliakov, A. Kumar, A.M. Barghash, F.E. Goda, H.M. Eisa, T. Wenzler, R. Brun, Y. Liu, W.D. Wilson, D.W. Boykin, Bioorg. Med. Chem. 19, 2156–2167 (2011)

    Article  CAS  Google Scholar 

  6. Y. Zhang, S. Yang, B.A. Song, D.Y. Hu, Agrochemicals 47, 164–170 (2008)

    CAS  Google Scholar 

  7. L. Jiang, H. Wang, W. Mu, Z. Ji, P. Cao, Chin. J. Chem. 29, 539–543 (2011)

    Article  CAS  Google Scholar 

  8. L.Z. Ling, A.P. Liu, C. Chen, Z.Z. Wei, D.S. Wang, D.L. Yin, X.G. Wang, Chin. J. Pestic. Sci. 8, 25–29 (2006)

    CAS  Google Scholar 

  9. X.F. Zhu, D.Q. Shi, Chin. J. Chem. 27, 565–568 (2009)

    Article  CAS  Google Scholar 

  10. L. Chen, J.H. Yao, L.P. Yuan, J. Cao, Y. Huang, W. Xie, C.C. Ni, Z. Shen, X.L. Li, Y.B. Zhang, Acta Chim. Sinica 65, 2583 (2007)

    CAS  Google Scholar 

  11. P. Leroux, A.S. Walker, Pest Manag. Sci. 67, 44–59 (2011)

    Article  CAS  Google Scholar 

  12. A.S. Walker, C. Auclair, M. Gredt, P. Leroux, Pest Manag. Sci. 65, 906–915 (2009)

    Article  CAS  Google Scholar 

  13. Y.B. Zhang, Y. Zhang, X.Y. Wu, New Developments in the World Pesticide. (Chemical Industry Press, Beijing, 2010), p 242

  14. H.M.F. Madkour, A.A. Farag, S.S. Ramses, N.A.A. Ibrahiem, Phosphorus. Sulfur Silicon 181, 255–265 (2006)

    Article  CAS  Google Scholar 

  15. J.L. Sun, W. Mu, Pesticide Science Experimental Techniques and Guidance. Chemical Industry Press, Beijing, 2009), pp. 228–229

  16. L.L. Jiang, C.N. Chen, Y.F. Zhou, Q. Chen, G.F. Yang, Chin. J. Org. Chem. 29, 1392–1404 (2009)

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Chemistry and Material Science, Shandong Agricultural University, Tai’an, 271018, China

    Shaofang Zhou, Peizhi Zhang & Lin Jiang

  2. College of Plant Protection, Shandong Agricultural University, Tai’an, 271018, China

    Fubo Li

Authors
  1. Shaofang Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fubo Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Peizhi Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lin Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lin Jiang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhou, S., Li, F., Zhang, P. et al. Synthesis and antifungal activity of novel 1-(1H-benzoimidazol-1-yl)propan-2-one oxime-ethers containing the morpholine moiety. Res Chem Intermed 39, 1735–1743 (2013). https://doi.org/10.1007/s11164-012-0708-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0708-5

Keywords

Search

Navigation