Citation: Sun Guoshao, Zhang Jingjing, Jin Shuhui, Zhang Jianjun. Synthesis and Insecticidal Activity of 4"-Avermectin Triazole Derivatives Containing Amide Unit[J]. Chinese Journal of Organic Chemistry, ;2018, 38(5): 1214-1222. doi: 10.6023/cjoc201712019 shu

Synthesis and Insecticidal Activity of 4"-Avermectin Triazole Derivatives Containing Amide Unit

College of Science, China Agricultural University, Beijing 100193

Corresponding author: Jin Shuhui, shuhuij@cau.edu.cn Zhang Jianjun, zhangjianjun@cau.edu.cn
Received Date: 12 December 2017
Revised Date: 5 January 2018
Available Online: 10 May 2018
Fund Project: Project supported by the National Natural Science Fondation of China (No. 21772230)the National Natural Science Fondation of China 21772230

Figures(2)

Based on avermectin structure framework, a series of novel 4"-avermectin triazole derivatives containing amide unit were synthesized via the method of click reaction and amidation. The structures of target compounds were fully characterized by ¹H NMR, ¹³C NMR and HRMS. The preliminary bioassay showed that the target compounds possessed certain insceticidal activities against Tetranychus cinnabarinus, Myzus persicae and Caenorhabditis elegans. At the concentration of 0.1 μg/mL, the lethal rates of 4"-(1-(4-(2-(4-chlorphenyl)-3-methylbutylamido)-1H-1, 2, 3-triazolyl)acetamido)avermectin B1a (11b) and 4"-(1-(4-chlorobenzoamido)-1H-1, 2, 3-triazolyl)acetamido)avermectin B1a (11e) against Tetranychus cinnabarinus were 83.5% and 81.2%, respectively, and the lethal rates of 4"-(1-(2-amido-3-methylphenylethylamido)-1H-1, 2, 3-triazolyl)acetamido)avermectin B1a (11i) against Myzus persicae (c=50 μg/mL) and Caenorhabditis elegans (c=1 μg/mL) were 86.4% and 74.6%, which were better than that of avermetcin B1a.
- amide,
- 1, 2, 3-triazole,
- avermectin B1a,
- insecticidal activity
1. [1]
  Wang, Z. J.; Gao Y.; Hou, Y. L.; Zhang, C.; Yu, S. J.; Bian, Q.; Li, Z. M.; Zhao, W. G. Eur. J. Med. Chem. 2014, 86, 87. doi: 10.1016/j.ejmech.2014.08.029
2. [2]
  Ma, Y. M.; Liu, R. H.; Gong, X. Y.; Li, Z.; Huang, Q. C.; Wang, H. S.; Song, G. H. J. Agric. Food Chem. 2006, 54, 7724. doi: 10.1021/jf0609328
3. [3]
  Liu, J. H.; Liu, Y.; Jian, J. Y.; Bao, X. P. Chin. J. Org. Chem. 2013, 33, 370(in Chinese).
4. [4]
  Fu, N. N.; Wang, S. L.; Zhang, Y. Q.; Zhang, C. X.; Yang, D. L.; Weng, L. X.; Zhao, B. M.; Wang, L. H. Eur. J. Med. Chem. 2017, 136, 596. doi: 10.1016/j.ejmech.2017.05.001
5. [5]
  Dai, H.; Liu, J. B.; Tao, W. F.; Miao, W. K.; Fang, J. X.; Wang, Q. M. Chin. J. Org. Chem. 2016, 36, 393(in Chinese).
6. [6]
  Mao, M. Z.; Li, Y. X.; Liu, Q. X.; Xiong, L. X.; Zhang, X.; Li, Z. M. J. Pestic. Sci. (Tokyo, Jpn.) 2015, 40, 138. doi: 10.1584/jpestics.D15-020
7. [7]
  Xiong, X. Q.; Chen, H. X. Chin. J. Org. Chem. 2013, 33, 1437(in Chinese).
8. [8]
  Pitterna, T.; Cassayre, J.; Huter, O. F.; Jung, P. M. J.; Maienfisch, P.; Kessabi, F. M.; Quaranta, L.; Tobler, H. Bioorg. Med. Chem. 2009, 17, 4085. doi: 10.1016/j.bmc.2008.12.069
9. [9]
  Yamashita, S.; Hayashi, D.; Nakano, A.; Hayashi, Y.; Hirama, M.; J. Antibiot. 2016, 69, 31. doi: 10.1038/ja.2015.47
10. [10]
  Sun, P.; Zhao, Q. F.; Wu, Z. H.; Zhang, W.; Liu, W. J. Nat. Prod. 2015, 78, 301. doi: 10.1021/np500468f
11. [11]
  Zhang, J.; Nan, X.; Yu, H. T.; Cheng, P. L.; Zhang, Y.; Li, Y. Q.; Zhang, S. Y.; Hu, G. F.; Liu, H. X.; Chen, A. L. Eur. J. Med. Chem. 2016, 121, 422. doi: 10.1016/j.ejmech.2016.05.056
12. [12]
  Liu, X. G.; Wu, J. P.; Liang, X. M.; Wang, D. Q. Pest Manage. Sci. 2004, 60, 697. doi: 10.1002/(ISSN)1526-4998
13. [13]
  Blizzard, T.; Margiatto, G.; Linn, B.; Mrozik, H.; Fisher, M.; Bioorg. Med. Chem. Lett. 1991, 1, 369. doi: 10.1016/S0960-894X(01)80475-3
14. [14]
  Jia, Y. M.; Liang, X. M.; Fang, X. Q.; Wu, J. P.; Wang, D. Q.; Rui, C. H.; Fan, X. L.; Zhao, H. Y.; Wang, Y. X. Chin. Chem. Lett. 2007, 18, 895. doi: 10.1016/j.cclet.2007.06.003
15. [15]
  Bi, F. C.; Zhao, J. P. Modern Agrochem. 2003, 2, 34(in Chinese).
16. [16]
  Pan, B. L.; Wang, M.; Wang, Y. W.; Pan, Z. D. Chin. J. Vet. Parasitol. 2003, 11, 59(in Chinese).
17. [17]
  Schmitz, J.; Li, T.; Bartz, U.; Guetschow, M. ACS Med. Chem. Lett. 2016, 7, 211. doi: 10.1021/acsmedchemlett.5b00474
18. [18]
  Gao, X. H.; Qian, P. C.; Zhang, X. G.; Deng, C. L. Synlett 2016, 27, 1110. doi: 10.1055/s-00000083
19. [19]
  Rajagopal, B.; Chen, Y. Y.; Chen, C. C.; Liu, X. Y.; Wang, H. R.; Lin, P. C. J. Org. Chem. 2014, 79, 1254. doi: 10.1021/jo402670d
20. [20]
  Pizzo, C.; Mahler, S. G. J. Org. Chem. 2014, 79, 1856. doi: 10.1021/jo402661b
21. [21]
  Guo, P.; Huang, J. H.; Huang, Q. C.; Qian, X. H. Chin. Chem. Lett. 2013, 24, 957. doi: 10.1016/j.cclet.2013.06.033
22. [22]
  Peng, H. H.; Akhmedov, N. G.; Liang, Y. F.; Jiao, N.; Shi, X. D. J. Am. Chem. Soc. 2015, 137, 8912. doi: 10.1021/jacs.5b05415
23. [23]
  Sriram, D.; Yogeeswari, P.; Dinakaran, M.; Banerjee, D.; Bhat, P.; Gadhwal, S. Eur. J. Med. Chem. 2010, 45, 120. doi: 10.1016/j.ejmech.2009.09.033
24. [24]
  Arcadi, A.; Cacchi, S.; Cascia, L.; Fabrizi, G.; Marinelli, F. Org. Lett. 2001, 3, 2501. doi: 10.1021/ol016133m
25. [25]
  Cvetovich, R. J.; Kelly, D. H.; DiMichele, L. M.; Shuman, R. F.; Grabowski, E. J. J. J. Org. Chem. 1994, 59, 7704. doi: 10.1021/jo00104a028
26. [26]
  Sun, L.; Ling, Y.; Wang, C.; Sun, Y. F.; Rui, C. H.; Yang, X. L. Chin. J. Org. Chem. 2011, 31, 2061(in Chinese).
27. [27]
  Luciana, M. K.; Jorge, F. S. F.; Anne, M. Z.; Carol, M.; David, S. L.; Ana, C. S. C.; Alessandro, F. T. A. Vet. Parasitol. 2011, 182, 264. doi: 10.1016/j.vetpar.2011.05.020
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