Citation: Zhang Jingpeng, Qin Yaoguo, Li Wenhao, Ling Yun, Yang Libo, Song Dunlun, Yang Xinling. Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1883-1889. doi: 10.6023/cjoc201603021 shu

Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions

Zhang Jingpeng ^a ,
Qin Yaoguo ^a ,
Li Wenhao ^a ,
Ling Yun ^a ,
Yang Libo ^b ,
Song Dunlun ^b ,
Yang Xinling ^a,*,,

a.
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193
b.
Department of Entomology, College of Plant Protection, China Agricultural University, Beijing 100193

Corresponding author: Yang Xinling, yangxl@cau.edu.cn
Received Date: 14 March 2016
Revised Date: 7 April 2016

Fund Project: Project supported by the National Natural Science Foundation of China No. 21132003

Figures(2)

In order to discover novel compounds with high-activity to control aphid, aphid alarm pheromone (E)-β-farnesene (EBF) was chosen as lead compound and a series of substituted EBF analogues were designed by replacing unstable conjugated double bond of EBF with different substitutions benzene ring. An N-alkylation route was optimized by using aniline and (E)-1-chloro-3,7-dimethyl-2,6-octadiene. Nineteen EBF analogues were synthesized with yields of 39%～83% in this optimization reaction condition. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS analysis. Bioassay showed that the title compounds demonstrated repellent activity against Myzus persicae (Sulzer). In particular, 4d, 4h and 4k exhibited excellent repellent activity of 56.3%, 58.3% and 50.3% respectively. The performed structure-activity relationship indicated that introduction of halogen group at the 4 position of phenyl ring displayed relatively higher activity.
- EBF analogues,
- benzene ring,
- N-alkylation,
- repellent activity,
- structure-activity relationship
1. [1]
  Wang, G.-P.; Yu, X.-D.; Fan, J.; Wang, C.-S.; Xia, L.-Q. J. Integr. Plant. Biol. 2015, 57, 770.
2. [2]
  Bruce, T. J. A.; Birkett, M. A.; Blande, J.; Hooper, A. M.; Martin, J. L.; Khambay, B.; Prosser, I.; Smart, L. E.; Wadhams, L. J. Pest. Manag. Sci. 2005, 61, 1115.
3. [3]
4. [4]
  Dahl, M. L. Dtsch. Ent. Z. 1971, 18, 121.
5. [5]
  Kislow, C. J.; Edward, L. J. Nature 1972, 235, 108.
6. [6]
  Bowers, W. S.; Nault, L. R.; Webb, R. E.; Dutky, S. R. Science 1972, 177, 1121.
7. [7]
  Mauchamp, B.; Picker, J. J. Agronomie 1987, 7, 523.
8. [8]
  Kunert, G.; Otto, S.; Rose, U. R.; Gershenzon, J.; Weisser, W. W. Ecol. Lett. 2005, 8, 596.
9. [9]
  Joachim, C.; Weisser, W. W. J. Chem. Ecol. 2015, 47, 267.
10. [10]
  Francis, F.; Lognay, G.; Haubruge, E. J. Chem. Ecol. 2004, 30, 741.
11. [11]
  Hatano, E.; Kunert, G.; Weisser, W. W. Eur. J. Entomol. 2008, 105, 797.
12. [12]
  Heuskin, S.; Lorge, S.; Godin, B.; Leroy, P.; Frere, I.; Verheggen, F. J.; Haubruge, E.; Wathelet, J. P.; Mestdagh, M.; Hance, T.; Lognay, G.; Pest. Manage. Sci. 2012, 68, 127.
13. [13]
  Joachim, C.; Hatano, E.; David, A.; Kunert, M.; Linse, C.; Weisser, W. W. J. Chem. Ecol. 2013, 39, 773.
14. [14]
  Griffiths, D. C.; Pickett, J. A. Entomol. Exp. Appl. 1980, 27, 199.
15. [15]
  Dawson, G. W.; Giffiths, D. C.; Pickett, J. A.; Plumb, R. T.; Woodcock, C. M.; Zhang, Z.-N. Pestic. Sci. 1988, 22, l7.
16. [16]
  Bowers, W. S.; Nishino, C.; Montgomery, M. E.; Nault, L. R. Insects Physiol. 1977, 23, 697.
17. [17]
18. [18]
19. [19]
20. [20]
  Sun, Y.-F.; Filomena, D.; Qiao, H.-L.; Immacolata, I.; Yang, S.-X.; Ling, Y.; Lea, R.; Donatella, B.; Patrizia, F.; Yang, X.-L.; Paolo, P. PLoS One 2012, 7, e32759.
21. [21]
  Sun, Y.-F.; Qiao, H.-L.; Ling, Y.; Yang, S.-X.; Rui, C.-H.; Paolo Pelosi; Yang, X.-L. J. Agric. Food Chem. 2011, 59, 2456.
22. [22]
  Ohshima, T,; Miyamoto, Y,; Ipposhi, J.; Nakahara, Y.; Utsunomiya, M.; Mashima, K. J. Am. Chem. Soc. 2009, 131, 14317.
23. [23]
  Zhao, Y.-S.; Foo, S. W.; Saito, S. Angew. Chem., Int. Ed. 2011, 50, 3006.
24. [24]
  Kazuhide, T.; Tsuneaki, Y.; Susumu, A.; Hidenori, K.; Takanao, T.; Hidemasa, T.; Akira, M.; Ryoji, N.; Sei, O. J. Am. Chem. Soc. 1984, 106, 5208.
25. [25]
26. [26]
  Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028.
27. [27]
  Romera, J. L.; Cid, J. M.; Trabanco, A. A. Tetrahedron Lett. 2004, 45, 8797.
28. [28]
  Siswanto, C.; Rathman, J. F. J. Colloid Interface Sci. 1997, 196, 99.
29. [29]
  Pinchin, R.; De Oliveira Filho, A. M.; Figueiredo, M. J.; Muller, C. A.; Gilbert, B.; Szumlewicz, A. P.; Benson, W. W. J. Econ. Entomol. 1978, 71, 950.
30. [30]
  Sun, L. Ph.D. Dissertation, China Agricultural University, Beijing, 2013 (in Chinese).
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