Skip to main content
Log in

Synthesis and Antifungal Activity of Cuminic Acid Derivatives

  • Published:
Chemistry of Natural Compounds Aims and scope

A series of benzamide derivatives (compounds 1–29) was synthesized based on the lead compound cuminic acid. The crystal structure of compound 11 was characterized by single crystal X-ray diffraction. The antifungal activity of the synthesized compounds was determined against seven plant pathogenic fungi, namely Rhizoctonia solani, Gibberella zeae, Helminthosporium maydis, Sclerotinia sclerotiorum, Botrytis cinerea, Coniothyrium diplodiella, and Coniothyrium lagenarium. Preliminary results indicated that most of them revealed significant antifungal activity. Among them, compound 22 showed the strongest activity and possessed better antifungal activity against H. maydis, S. sclerotiorum, and B. cinerea than carbendazim.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1.

Similar content being viewed by others

References

  1. L. F. Hu, J. T. Feng, X. Zhang, and Y. L. Zhang, Chin. J. Pestic. Sci., 9 (4), 330 (2007).

    CAS  Google Scholar 

  2. L. F. Hu, C. Z. Chen, X. H. Yi, J. T. Feng, and X. Zhang, Acta Bot. Boreal-Occident. Sin., 28 (11), 2349 (2008).

    CAS  Google Scholar 

  3. I. Tunc, B. M. Berger, F. Erler, and F. Dagli, J. Stored Prod. Res., 36 (2), 161 (2000).

    Article  CAS  Google Scholar 

  4. G. Singh and R. K. Upadhyay, Fitoterapia, 61 (1), 86 (1991).

    Google Scholar 

  5. M. Ozcan and O. Erkmen, Eur. Food. Res. Technol., 212 (6), 658 (2001).

    Article  CAS  Google Scholar 

  6. L. Jayasinghea, B. M. M. Jayarathna, K. H. R. N. Jayarathna, N. W. M. G. Udishani, B. M. R. Bandara, N. Hara, and Y. Fujimoto, Phytochemistry, 62 (4), 637 (2003).

    Article  Google Scholar 

  7. B. V. Schmeling and M. Kulla, Science, 152, 659 (1966).

    Article  CAS  PubMed  Google Scholar 

  8. G. Daidone, S. Plescia, D. Raffa, D. Schillaci, B. Maggio, F. Benetollo, and G. Bombieri, Heterocycles, 43, 2385 (1996).

    Article  CAS  Google Scholar 

  9. Y. Xu and S. J. Xue, Chem. Res. Chin. Univ., 25 (6), 846 (2009).

    CAS  Google Scholar 

  10. W. Q. Zhou, W. Yang, L. Q. Xie, and X. C. Cheng, J. Inorg. Biochem., 99, 1314 (2005).

    Article  CAS  Google Scholar 

  11. B. Narayana, K. K. Vijava Raj, B. V. Ashalatha, N. Suchetha Kumari, and B. K. Sarojini, Eur. J. Med. Chem., 39, 867 (2004).

    Article  CAS  PubMed  Google Scholar 

  12. L. R. Wen, M. Li, S. X. Jing, W. Cao, and H. Z. Yang, Chin. J. Org. Chem., 25 (2), 197 (2005).

    CAS  Google Scholar 

  13. B. S. Priya, S. Najunda Swamy, M. V. Tejesvi, Basappa, G. Sarala, S. L. Gaonkar, S. Naveen, J. Shashidhara Prasad, and K. S. Rangappa, Eur. J. Med. Chem., 41, 1262 (2006).

    Article  CAS  PubMed  Google Scholar 

  14. T. Ertan, I. Yildiz, S. Ozkan, O. Temiz-Arpaci, F. Kaynak, I. Yalcin, E. Aki-Sener, and U. Abbasoglu, Bioorg. Med. Chem., 15, 2032 (2007).

    Article  CAS  PubMed  Google Scholar 

  15. F. Wen, H. Zhang, Z. Y. Yu, H. Jin, Q. Yang, and T. P. Hou, Pestic. Biochem. Phys., 98, 248 (2010).

    Article  CAS  Google Scholar 

  16. Z. Y. Yu, G. Y. Shi, Q. Sun, H. Jin, Y. Teng, K. Tao, G. P. Zhou, W. Liu, F. Wen, and T. P. Hou, Eur. J. Med. Chem., 44, 4726 (2009).

    Article  CAS  PubMed  Google Scholar 

  17. P. Leroux, J. Pestic. Sci., 47, 191 (1996).

    Article  CAS  Google Scholar 

  18. R. W. Smiley, D. E. Wilkins, and E. L. Klepper, Plant. Dis., 74, 782 (1990).

    Article  CAS  Google Scholar 

  19. H. R. Kataria, P. R. Verma, and G. Racow, Ann. Appl. Biol., 123, 247 (1993).

    Article  CAS  Google Scholar 

  20. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann, J. Appl. Crystallogr., 42, 339 (2009).

    Article  CAS  Google Scholar 

  21. L. Palatinus and G. Chapuis, J. Appl. Crystallogr., 40, 786 (2007).

    Article  CAS  Google Scholar 

  22. L. Palatinus and A. van der Lee, J. Appl. Crystallogr., 41, 975 (2008).

    Article  CAS  Google Scholar 

  23. L. Palatinus, S. J. Prathapa, and S. van Smaalen, J. Appl. Crystallogr., 45, 575 (2012).

    Article  CAS  Google Scholar 

  24. G. M. Sheldrick, Acta Crystallogr., A64, 112 (2008).

    Article  Google Scholar 

  25. W. Huang and G. F Yang, Bioorg. Med. Chem., 14, 8280 (2006).

Download references

Acknowledgment

This project was supported by the Scientific Research Fund of Sichuan Provincial Education Department (No. 13ZA0206), the Key Scientific Research Fund of Xihua University (No. Z1013314), the Innovation Fund of Postgraduates of Xihua University (No. YCJJ 2015050), and the Research Center for Advanced Computation, Xihua University.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xiaorong Tang.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2017, pp. 945–948.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yang, J., Gao, Y., Liu, H. et al. Synthesis and Antifungal Activity of Cuminic Acid Derivatives. Chem Nat Compd 53, 1112–1116 (2017). https://doi.org/10.1007/s10600-017-2212-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-017-2212-z

Keywords

Navigation