Notes

Synthesis and Fungicidal Activity of N-Alkoxyl Amide Derivatives

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  • a School of Chemistry and Food Engineering, Changsha University of Science and Technology, Changsha 410114;
    b CAC Shanghai International Trading Co., Ltd., Shanghai 200335

Received date: 2018-06-19

  Revised date: 2018-09-05

  Online published: 2018-10-26

Supported by

Project supported by the Changsha Science and Technology Project (Nos. kq1801163, kq1801052) and the Hunan Provincial Engineering Research Center for Food Processing of Aquatic Biotic Resources (No. 2018KJY08).

Abstract

In order to find lead compounds with high fungicidal activity, the phenyl moiety of pydiflumetofen was replaced by substituted 1-phenyl-3-hydroxylpyrazole moiety of pyraclostrobin according to the method of active substructure combination. 12 novel N-alkoxyl amides were synthesized and their structures were confirmed by 1H NMR, 13C NMR and HRMS. Preliminary fungicidal activity screening results showed that some analogues exhibited certain fungicidal activity against Phakopsora pachyrhizi, Pseudoperonospora cubensis or Erysiphe cichoracearum, compound 3a displayed 95% protective effect against Erysiphe cichoracearum at 100 mg/L.

Cite this article

Huang Pengmian, Zhou Zhihui, Du Yonglei, Pang Huailin, Lü Liang . Synthesis and Fungicidal Activity of N-Alkoxyl Amide Derivatives[J]. Chinese Journal of Organic Chemistry, 2019 , 39(3) : 867 -872 . DOI: 10.6023/cjoc201806029

References

[1] Wang, B. Z.; Xu, X. Y.; Tao, Y. C. Chin. J. Pestic. Sci. 2010, 12, 429(in Chinese). (王宝珠, 徐晓勇, 陶玉成, 农药学学报, 2010, 12, 429.)
[2] Loiseleur, O.; Durieux, P.; Trah, S.; Edmunds, A.; Jeanguenta,A.; Stoller, A.; Hughes, D. J. WO 093402, 2007[Chem. Abstr. 2007, 147, 301166.]
[3] Ikegami, H.; Jachmann, M.; Nokura, Y.; Iwata, Y. WO 043677, 2007[Chem. Abstr. 2007, 146, 421979].
[4] Sanz, D.; Gazeneuve, E. WO 051814, 2007[Chem. Abstr. 2007, 146, 485984].
[5] Li. X.; Shen, Y. Q.; Jiang, L. N.; Zhu, X. L.; Yang, W. C.; Huang, W.; Yang, G. F. ACS Symp. Ser. 2015, 1204, 175.
[6] Kulka, M.; Schmeling, B. Modern Selective Fungicides——Prop-erties, Applications, Mechanisms of Action, 2nd ed., Gustav Fischer Verlag, New York, 1995, p. 133.
[7] Schewe, T.; Lyr, H. Modern Selective Fungicides——Proper-ties, Applications, Mechanisms of Action, 2nd ed., Gustav Fischer Verlag, New York, 1995, p. 149.
[8] Stammler, G.; Brix, H. D.; Glattli, A.; Semar, M.; Schoefl, U. Proceedings of the XVI International Plant Protection Congress, Glasgow, Scotland, 2007, p. 40.
[9] Avenot, H. F.; Michailides, T. J. Crop Prot. 2010, 29, 643.
[10] Qiu S. S.; Bai Y. L. Modern Agrochem. 2014, 13, 1(in Chinese). (仇是胜, 柏亚罗, 现代农药, 2014, 13, 1.)
[11] Qiu S. S.; Bai Y. L. Modern Agrochem. 2015, 14, 1(in Chinese). (仇是胜, 柏亚罗, 现代农药, 2015, 14, 1.)
[12] Li. X.; Li, H.; Jiang, L. N.; Ge, J. M.; Yang, W.-C.; Zhu, X. L.; Yang, G. F. J. Agric. Food Chem. 2017, 65, 1021.
[13] Li. X.; Zhu, X. L.; Gao, H. W.; Fu, Y.; Hu, S. Q.; Jiang, L. N.; Yang, W. C.; Yang, G. F. J. Agric. Food Chem. 2016, 64, 4830.
[14] Li. X.; Zhu, X. L.; Shen, Y. Q.; Wishwa, W. K. W. M.; Li, K.; Yang, G.-F. Eur. J. Med. Chem. 2015, 95, 424.
[15] Yao, T. T.; Fang, S. W.; Li, Z. S.; Xiao, D. X.; Cheng, J. L.; Ying, H. Z.; Du, Y. J.; Zhao, J. H.; Dong, X. W. J. Agric. Food Chem. 2017, 65, 3204.
[16] Bai Y. L. Pestic. Express 2011, 22, 24(in chinese). (柏亚罗, 农药快讯, 2011, 22, 24.)
[17] Rheinheimer, J.; Terteryan, V.; Redlich S.; Kremzow, D.; Rosenbaum, C.; Rohrer S.; Grammenos, W.; Pilger C.; Roehl F.; Gewehr, M.; Stammler, G.; Montag, J.; Sauter, H. WO 2013092224, 2013[Chem. Abstr. 2013, 159, 160272].
[18] Stierli, D.; Walter, H.; Rommel, M.; Hanreich, R. G.; Zeller, M.; Vettiger, T.; Smejkal, T. WO 2013127764, 2013[Chem. Abstr. 2013, 159, 426447].

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