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

  • 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.
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    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., RynaxypyrTM: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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