Citation: Lei Peng, Ding Xinji, Wu Yuanyong, Ma Zhiqing. Synthesis and Insecticidal Activity of Terpinen-4-ol Derivatives Containing Oxime Ether[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 2070-2074. doi: 10.6023/cjoc201812039 shu

Synthesis and Insecticidal Activity of Terpinen-4-ol Derivatives Containing Oxime Ether

College of Plant Protection, Northwest A & F University, Yangling 712100

Corresponding author: Ma Zhiqing, mazhiqing2000@126.com

^†

Received Date: 21 December 2018
Revised Date: 21 January 2019
Available Online: 29 July 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 31572029) and the Starting Research Fund from the Northwest A & F University (No. 00200-Z109021809)the Starting Research Fund from the Northwest A & F University 00200-Z109021809the National Natural Science Foundation of China 31572029

Figures(3)

In order to discover high activity lead compound, based on our previous studies, a series of terpinen-4-ol deri- vatives containing oxime ether were designed and synthesized. The bioassay results showed that the target compounds displayed good insecticidal activity against Mythimna separata (Walker). Especially, compound 3a exhibited satisfied activity with the LD₅₀ value of 0.0054 mg/insect, which is 19.1 times than terpinen-4-ol. As a high activity compound with simple structure, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-prop-2-yn-1-yl oxime (3a) could be a lead compound for further study.
- oxime ether,
- terpinen-4-ol,
- natural product,
- biological activity,
- Mythimna separata
1. [1]
  Jiang, Y.-Y.; Li, C.-G.; Zeng, J.; Liu, J. Chin. J. Appl. Entomol. 2014, 51, 890(in Chinese). doi: 10.7679/j.issn.2095-1353.2014.109
2. [2]
  Bian, H.-X.; Ma, H.-F.; Zheng, X.-X.; Peng, M.-H.; Li, Y.-P.; Su, J.-F.; Wang, H.; Li, Q.; Xia, R.-X.; Liu, Y.-Q.; Jiang, X.-F. Sci. Rep. 2017, 7, 2324. doi: 10.1038/s41598-017-02513-6
3. [3]
  Huang, Q.; Jiang, T.; Jiang, X.-B.; Ling, Y.; Chen, Y.-C.; Long, L.-P. J. Environ. Entomol. 2017, 39, 1363(in Chinese).
4. [4]
  Nie, J.-D.; Wang, H.-W. Plant Protect. 2017, 8, 84(in Chinese).
5. [5]
  Li, L.-C.; Shi, T.; Su, N.-N. Plant Protect. 2016, 4, 100(in Chinese).
6. [6]
  Wang, J.-D.; Wang, Y.-R.; Wang, Y.-Z.; Wang, W.-Z.; Wang, R.; Gao, S.-J. Gene 2018, 670, 1. doi: 10.1016/j.gene.2018.05.094
7. [7]
  Kim, K.-N.; Yun, C.-N.; Sin, U.-C.; Huang, Z.-J.; Huang, Q.-Y.; Lei, C.-L. Environ. Sci. Pollut. Res. 2018, 25, 35176. doi: 10.1007/s11356-018-3415-y
8. [8]
  Yasoob, H.; Abbas, N.; Li Y.-F.; Zhang, Y.-L. Phytoparasitica 2018, 46, 627. doi: 10.1007/s12600-018-0692-4
9. [9]
  Zhang, X.-M.; Lei. P.; Li, X.-L.; Yang, X.-L.; Zhang, X.-B.; Sun, T.-D.; Ling, Y. Chin. J. Org. Chem. 2019, 39, 3197(in Chinese).
10. [10]
  Lei, P.; Xu, Y.; Du, J.; Yang, X.-L.; Yuan, H.-Z.; Xu, G.-F.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 2544. doi: 10.1016/j.bmcl.2016.03.085
11. [11]
  Nascimento, N. R. F.; Leal-Cardoso, J. H.; Lessa, L. M. A.; Roriz-Filho, J. S.; Cunha K. M. A.; Fonteles, M. C. J. Pharm. Pharmacol. 2005, 57, 467. doi: 10.1211/0022357055696
12. [12]
  Liu, Y.-C.; Hei, Y.-R. Shaanxi J. Agric. Sci. 2013, 4, 92(in Chinese).
13. [13]
  Tighe, S.; Gao, Y.-Y.; Tseng, S. C. G. Transl. Vis. Sci. Technol. 2013, 2, 1.
14. [14]
  Sharifi-Rad, J.; Salehi, B.; Varoni, E. M.; Sharopov, F.; Yousaf, Z.; Ayatollahi, S. A.; Kobarfard, F.; Sharifi-Rad, M.; Afdjei, M. H.; Sharifi-Rad, M.; Iriti, M. Phytother. Res. 2017, 31, 1475. doi: 10.1002/ptr.5880
15. [15]
  Shapira, S.; Pleban, S.; Kazanov, D.; Tirosh, P.; Arber, N. PLoS One 2016, 11, e0156540. doi: 10.1371/journal.pone.0156540
16. [16]
  Zhang, Z.; Shen, P.; Lu, X.; Li, Y.; Liu, J.; Liu, B.; Fu, Y.; Cao, Y.; Zhang, N. Front. Immunol. 2017, 8, 558. doi: 10.3389/fimmu.2017.00558
17. [17]
  Li, L.; Xiong, X.; Ma, S.-J.; Ma, Z.-Q.; Zhang, X. Acta Entomol. Sinica 2015, 58, 761(in Chinese).
18. [18]
  Chen, G.-Q.; Li, G.-Z.; Feng, J.-T.; Chen, A.-L.; Zhang, X. J. Northwest A & F Univ. (Nat. Sci. Ed.) 2003, 31, 67(in Chinese).
19. [19]
  Hei, Y.-R.; Ma, Z.-Q.; Zhang, X. Chin. J. Pestic. Sci. 2011, 13, 133(in Chinese). doi: 10.3969/j.issn.1008-7303.2011.02.06
20. [20]
  Feng, J.-T.; Li, Z.-Y.; Ma, Z.-Q.; Chen, G.-Q.; Zhang, X. J. Northwest A & F Univ. (Nat. Sci. Ed.) 2009, 37, 156(in Chinese). doi: 10.3321/j.issn:1671-9387.2009.11.027
21. [21]
  Ma, Z.-Q.; Hei, Y.-R.; Chen, G.-Q.; Cai, C.-L.; Zhang, X. J. Northwest A & F Univ. (Nat. Sci. Ed.) 2009, 37, 147(in Chinese).
22. [22]
  Dai, H.; Yao, W.; Sun, S.-Y.; Li, L.; Shi, L.; Qian, H.-W.; Li, C.-J.; Shi, J.; Shi, Y.-J. Chin. J. Org. Chem. 2017, 37, 3155(in Chinese).
23. [23]
  Zan, N.-N.; Wan, F.-X.; Wang, S.-C.; Zhang, J.-H.; Jiang, L. Chin. J. Org. Chem. 2017, 37, 1537(in Chinese).
24. [24]
  Wei, W.; Cheng, D.-D.; Chen, W.; Liu, J.-B.; Wan, Y.-Y.; Li, Y.-X.; Li, Y.-H.; Yu, S.-J.; Li, Z.-M. Chem. Res. Chin. Univ. 2016, 32, 195. doi: 10.1007/s40242-016-5406-1
25. [25]
  Luo, Y.-P.; Gong, Q.; Chen, Q.; Yang, G.-F. Chin. J. Org. Chem. 2008, 28, 1561(in Chinese).
26. [26]
  Jiang, L.-L.; Chen, C.-N.; Zhou, Y.-F.; Chen, Q.; Yang, G.-F. Chin. J. Org. Chem. 2009, 29, 1392(in Chinese).
27. [27]
  Qin, H.-L.; Leng, J.; Zhang, C.-P.; Jantan, I.; Amjad, M. W.; Sher, M.; Naeem-ul-Hassan, M.; Hussain, M. A.; Bukhari, S. N. A. J. Med. Chem. 2016, 59, 3549. doi: 10.1021/acs.jmedchem.6b00276
28. [28]
  Reddy, D. S.; Kongot, M.; Netalkar, S. P.; Kurjogi, M. M.; Kumar, R.; Avecilla, F.; Kumar, A. Eur. J. Med. Chen. 2018, 150, 864. doi: 10.1016/j.ejmech.2018.03.042
29. [29]
  Tan, J.; Zhou, M.; Cui, X.-H.; Wei, Z.-C.; Wei, W.-X. Molecules 2018, 23, 637. doi: 10.3390/molecules23030637
30. [30]
  Liu, A.-P.; Yao, J.-R. Chin. J. Pesitic. 2004, 43, 196(in Chinese). doi: 10.3969/j.issn.1006-0413.2004.05.002
31. [31]
  Yang, J.-Y.; Kim, M.-G.; Lee, S.-E.; Lee, H.-S. Planta Med. 2014, 80, 165. doi: 10.1055/s-0033-1360313
32. [32]
  Saad, M. M. G.; Abou-Taleb, H. K.; Abdelgaleil, S. A. M. Appl. Entomol. Zool. 2018, 53, 173. doi: 10.1007/s13355-017-0532-x
33. [33]
  Yildirim, E.; Emsen, B.; Kordali, S. J. Appl. Bot. Food Qual. 2013, 86, 198.
34. [34]
  Shen, L.-Q. M.S. Thesis, Hunan Normal University, Changsha, 2004 (in Chinese).
35. [35]
  Li, Q.-H.; Yin, D.-L.; Xiao, Y.; Duan, C.-S. Chin. J. Appl. Chem. 2000, 17, 536(in Chinese). doi: 10.3969/j.issn.1000-0518.2000.05.019
36. [36]
  Yu, M.-X. Chin. J. Pestic. 1994, 33, 14(in Chinese).
37. [37]
  Obata, T.; Fujii, K.; Fukuda, Y.; Tsutsumiuchi, K. EP 0391685, 1990.
38. [38]
  Wu, W.-J. Experimental Technique Introduction of Plant Chemical Protection, Shaanxi Science and Technology Press, Xi'an, 1988, p. 72(in Chinese).
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