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Synthesis and antifungal activity of novel α-alkoxyimino-(1H-benzoimidazol-2-yl)acetonitriles containing piperazine moiety

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Abstract

A series of α-alkoxyimino-[1-(4-methylpiperazino-1-yl)carbonylmethyl-1H-benzimidazol-2-yl] acetonitriles were synthesized from o-phenylenediamine, ethyl cyanoacetate, chloroacetyl piperazine, and haloalkane/benzyl chloride by multi-step reactions. The structures of the target compounds were elucidated by IR, 1H NMR, MS, and elemental analysis. All the target compounds were tested for in vitro antifungal activities against Sclerotinia sclerotiorum and Botrytis cinerea by the mycelium growth rate method, and the results indicated that some compounds displayed higher antifungal activity as compared to carbendazim.

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References

  1. P.Z. Zhang, S.F. Zhou, T.R. Li, L. Jiang, Chin. Chem. Lett. 23, 1381–1384 (2012)

    Article  CAS  Google Scholar 

  2. R.V. Patel, P.K. Patel, P. Kumari, D.P. Rajani, K.H. Chikhalia, Eur. J. Med. Chem. 53, 41–51 (2012)

    Article  CAS  Google Scholar 

  3. S.M. Abu-Bakr, F.A. Bassyouni, M.A. Rehim, Res. Chem. Intermed. 38, 2523–2545 (2012)

    Article  CAS  Google Scholar 

  4. A.T. Mavrova, D. Vuchev, K. Anichina, N. Vassilev, Eur. J. Med. Chem. 45, 5856–5861 (2010)

    Article  CAS  Google Scholar 

  5. M. Gaba, S. Singh, C. Mohan, Eur. J. Med. Chem. 76, 494–505 (2014)

    Article  CAS  Google Scholar 

  6. K. Shah, S. Chhabra, S.K. Shrivastava, P. Mishra, Med. Chem. Res. 22, 5077–5104 (2013)

    Article  CAS  Google Scholar 

  7. H.Z. Yang, X.M. Zou, Y.Q. Zhu, Morden pesticide chemistry (Chemical Industry Press, Beijing, 2013), pp. 300–302

    Google Scholar 

  8. J.B. Qiu, J.Q. Xu, J.J. Yu, C.W. Bi, C.J. Chen, M.G. Zhou, Pest Manag. Sci. 67, 191–198 (2011)

    Article  CAS  Google Scholar 

  9. S. Tu, Y.Q. Xie, S.Z. Gui, L.Y. Ye, Z.L. Huang, Y.B. Huang, L.M. Che, Bioorg. Med. Chem. Lett. 24, 2173–2176 (2014)

    Article  CAS  Google Scholar 

  10. R. Sun, Y. Li, M. Lu, L. Xiong, Q. Wang, Bioorg. Med. Chem. Lett. 20, 4693–4699 (2010)

    Article  CAS  Google Scholar 

  11. K.G. Watson, Aust. J. Chem. 64, 367–372 (2011)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  14. Y. Li, Appl. Chem. Ind. 42, 287–290 (2013)

    Google Scholar 

  15. S. Zhou, F. Li, P. Zhang, L. Jiang, Res. Chem. Intermed. 39, 1735–1743 (2013)

    Article  CAS  Google Scholar 

  16. M. Wang, Z. Qu, D. Du, L. Jiang, Chin. J. Org. Chem. 33, 1005–1009 (2013)

    Article  CAS  Google Scholar 

  17. H.F. Song, S.M. Ding, Dyestuffs Color. 40, 116 (2003)

    CAS  Google Scholar 

  18. O.T. Ilkun, S.J. Archibald, C.L. Barnes, N. Gerasimchuk, R. Biagioni, S. Silchenko, O.A. Gerasimchuk, V.N. Nemykin, Dalton Trans. 42, 5715–5729 (2008)

    Article  Google Scholar 

  19. J.L. Sun, W. Mu, Pesticide science experimental techniques and guidance (Chemical Industry Press, Beijing, 2009), pp. 228–229

    Google Scholar 

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Acknowledgments

This project was supported by Shandong Province Science and Technology Development Plan (No. 2013GZX20109).

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Authors and Affiliations

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

    Qingdong Jin & Fubo Li

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

    Ying Li, Fei Jin & Lin Jiang

Authors
  1. Qingdong Jin
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  2. Fubo Li
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  3. Ying Li
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  4. Fei Jin
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  5. Lin Jiang
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Correspondence to Lin Jiang.

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Jin, Q., Li, F., Li, Y. et al. Synthesis and antifungal activity of novel α-alkoxyimino-(1H-benzoimidazol-2-yl)acetonitriles containing piperazine moiety. Res Chem Intermed 41, 7695–7702 (2015). https://doi.org/10.1007/s11164-014-1853-9

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  • DOI: https://doi.org/10.1007/s11164-014-1853-9

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