N-烷氧基取代酰胺类化合物的合成及杀菌活性
收稿日期: 2018-06-19
修回日期: 2018-09-05
网络出版日期: 2018-10-26
基金资助
长沙市科技计划（Nos.kq1801163，kq1801052）和湖南省水生资源食品加工工程技术研究中心开放基金（No.2018KJY08）资助项目.
Synthesis and Fungicidal Activity of N-Alkoxyl Amide Derivatives
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).
黄朋勉, 周智慧, 杜永磊, 庞怀林, 吕亮 . N-烷氧基取代酰胺类化合物的合成及杀菌活性[J]. 有机化学, 2019 , 39(3) : 867 -872 . DOI: 10.6023/cjoc201806029
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.
Key words： pydiflumetofen; amide; pesticide; fungicidal activity
[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].
/
| 〈 |
|
〉 |
