Citation: Ye Liu, Chao Lei, Xiao-Yong Xu, Xu-Sheng Shao, Zhong Li. Design, synthesis and insecticidal activity of biphenyl-diamide derivatives[J]. Chinese Chemical Letters, ;2016, 27(03): 321-324. doi: 10.1016/j.cclet.2015.12.011 shu

Design, synthesis and insecticidal activity of biphenyl-diamide derivatives

1.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Xu-Sheng Shao, Zhong Li,
Received Date: 29 April 2015
Available Online: 24 July 2015

Diamides acting on insect ryanodine receptors are an intensive research area now. In order to search for novel candidates, a series of diamides containing biphenyl substructure were designed and synthesized. Their insecticidal activities against armyworms (Mythimna sepatara) and aphis (Aphis craccivora) were screened. The compounds with 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl substituent were found to be insecticidal to armyworms with the similar symptoms to poisoning by flubendiamide. In this research, we presented a novel type of diamide insecticide as a lead compound for further optimization.
- Diamide,
- Insecticide,
- Ryanodine insecticide,
- Biphenyl
1. [1]
  [1] G.P. Lahm, D. Cordova, J.D. Barry, New and selective ryanodine receptor activators for insect control, Bioorg. Med. Chem. 17(2009) 4127-4133.
2. [2]
  [2] E.F. Rogers, F.R. Koniuszy, J. Shaverl Jr., K. Folkers, Plant insecticides. (Ⅰ). Ryanodine, a new alkaloid from Ryania speciosa vahl, J. Am. Chem. Soc. 70(1948) 3086-3088.
3. [3]
  [3] P.R. Jefferies, R.F. Toia, J.E. Casida, Ryanodyl 3-(pyridine-3-carboxylate):a novel ryanoid from ryania insecticide, J. Nat. Prod. 54(1991) 1147-1149.
4. [4]
  [4] U. Ebbinghaus-Kintscher, P. Luemmen, N. Lobitz, et al., Phthalic acid diamides activate ryanodine-sensitive Ca²⁺ release channels in insects, Cell Calcium 39(2006) 21-33.
5. [5]
  [5] D. Cordova, E.A. Benner, M.D. Sacher, et al., Anthranilic diamides:a new class of insecticides with a novel mode of action, ryanodine receptor activation, Pest. Biochem. Physiol. 84(2006) 196-214.
6. [6]
  [6] D.B. Sattelle, D. Cordova, T.R. Cheek, (Ⅰ)nsect ryanodine receptors:molecular targets for novel pest control chemicals, (Ⅰ)nvert. Neurosci. 8(2008) 107-119.
7. [7]
  [7] S.Z. Qi, J.E. Casida, Species differences in chlorantraniliprole and flubendiamide insecticide binding sites in the ryanodine receptor, Pest. Biochem. Physiol. 107(2013) 321-326.
8. [8]
  [8] R. Nauen, (Ⅰ)nsecticide mode of action:return of the ryanodine receptor, Pest. Manage. Sci. 62(2006) 690-692.
9. [9]
  [9] M. Tohnishi, H. Nakao, T. Furuya, et al., Flubendiamide, a novel insecticide highly active against lepidopterous insect pests, J. Pestic. Sci. 30(2005) 354-360.
10. [10]
  [10] G.P. Lahm, T.M. Stevenson, T.P. Selby, et al., Rynaxypyr^TM:a new insecticidal anthranilic diamide that acts as a potent and selective ryanodine receptor activator, Bioorg. Med. Chem. Lett. 17(2007) 6274-6279.
11. [11]
  [11] C. Gnamm, A. Jeanguenat, A.C. Dutton, et al., Novel diamide insecticides:sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives, Bioorg. Med. Chem. Lett. 22(2012) 3800-3806.
12. [12]
  [12] T. Yan, S.J. Yu, P.F. Liu, et al., Design, Synthesis and biological activities of novel benzoyl hydrazines containing pyrazole, Chin. J. Chem. 30(2012) 919-923.
13. [13]
  [13] M.L. Feng, Y.F. Li, H.J. Zhu, et al., Synthesis, insecticidal activity, and structureactivity relationship of trifluoromethyl-containing phthalic acid diamide structures, J. Agric. Food Chem. 58(2010) 10999-11006.
14. [14]
  [14] M. Liu, Y. Wang, W.Z. Wangyang, et al., Design, synthesis, and insecticidal activities of phthalamides containing a hydrazone substructure, J. Agric. Food Chem. 58(2010) 6858-6863.
15. [15]
  [15] P.J.M. Jung, P. Durieux, W. Lutz, et al., (Ⅰ)nsecticidal compounds, WO 2007128410(2007).
16. [16]
  [16] O.F. Hueter, P.J.M. Jung, T. Pitterna, H. Smits, A. Stoller, (Ⅰ)nsecticidal compounds, WO 2014067838(2014).
17. [17]
  [17] A. Yanagi, Y. Watanabe, K. Wada, et al., (Ⅰ)nsecticidal 3-acylaminobenzanilides, WO 2007017075(2007).
18. [18]
  [18] A. Yanagi, Y. Watanabe, J. Mihara, et al., (Ⅰ)nsecticidal 2-acylaminothiazole-4-carboxamides, WO 2007051560(2007).
19. [19]
  [19] K. Yoshida, T. Wakita, H. Katsuta, A. Kai, et al., Agricultural/horticultural insecticide and method for using the same, EP 2324188(2003).
20. [20]
  [20] K. Yoshida, Y. Kobayashi, M. Nomura, et al., Amide derivative, pesticide containing such compound and use thereof, WO 2006137395(2006).
21. [21]
  [21] L. Lu, J.Y. Cassayre, T. Luksch, et al., Dihydrobenzofuran derivatives as insecticidal compounds, WO 2014135095(2014).
22. [22]
  [22] C. Dubost, P.Y. Coqueron, 5-Halogenopyrazole biphenylcarboxamides, WO 2013167550(2013).
23. [23]
  [23] A. Narine, J. Dickhaut, F. Kaiser, et al., Substituted mesoionic imine compounds for combating animal pests, WO 2014033244(2014).
24. [24]
  [24] C. Waldraff, S. Lehr, A. Angermann, et al., Herbicidally and insecticidally active thiazolopyridinones, WO 2013144096(2013).
25. [25]
  [25] (Ⅰ).L. Karle, P. Venkateshwarlu, R. Nagaraj, et al., Diphenic acid as a general conformational lock in the design of bihelical structures, Chem. Eur. J. 13(2007) 4253-4263.
26. [26]
  [26] R.P. Robinson, J.A. Bartlett, P. Bertinato, et al., Discovery of microsomal triglyceride transfer protein (MTP) inhibitors with potential for decreased active metabolite load compared to dirlotapide, Bioorg. Med. Chem. Lett. 21(2011) 4150-4154.
27. [27]
  [27] C.J. Perry, Z. Parveen, The cyclisation of substituted phthalanilic acids in acetic acid solution:a kinetic study of substituted N-phenylphthalimide formation, J. Chem. Soc. Perkin Trans. 2(2001) 512-521.

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