Citation: Yan Zhang, Yuxin Li, Huan Li, Junfeng Shang, Zhengming Li, Baolei Wang. Synthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators[J]. Chinese Chemical Letters, ;2022, 33(1): 501-507. doi: 10.1016/j.cclet.2021.05.027 shu

Synthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

nkzml@vip.163.com

nkwbl@nankai.edu.cn

Received Date: 5 March 2021
Revised Date: 1 May 2021
Accepted Date: 12 May 2021
Available Online: 24 May 2021

Figures(7)

With the aim of discovering new bioactive pesticides for crop protection, a series of novel sulfide-containing amide derivatives A were efficiently synthesized via a strategy of modifying the "amide" structure of anthranilic diamide insecticides. The single-crystal structures of A2-3 and A4-5 were firstly reported. The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities. Particularly, some sulfone-containing compounds, e.g., A2-3, A3-3 and A6-3, not only possessed favorable lethality rate (50%–100%) against P. xylostella at a concentration of 0.1 mg/L, but also held good activities towards a variety of agricultural pests such as M. separata, C. pipiens pallen, H. armigera and O. nubilalis; the larvicidal activities of A4-1 and A6-1 towards P. xylostella were close to that of chlorantraniliprole at 0.01 mg/L. The calcium imaging experiments revealed that the representative compounds A2-3 and A6-3 are potential ryanodine receptor (RyR) modulators. The structure–activity relationships were discussed in detail. These results provide useful information for further design and development of novel insecticides.
- Sulfide-containing amide derivatives,
- Sulfoxide,
- Sulfone,
- Insecticidal activities,
- Calcium channel
1. [1]
  R.R. Silva, J. Agric. Food Chem. 67 (2019) 4395-4396. doi: 10.1080/07391102.2018.1552623
2. [2]
  F. Wang, J.F. Yang, M.Y. Wang, et al., Sci. Bull. 65 (2020) 1184-1191. doi: 10.1016/j.scib.2020.04.006
3. [3]
  H. Yang, H. Qi, Z. Hao, et al., Chin. Chem. Lett. 31 (2020) 1271-1275. doi: 10.1016/j.cclet.2019.11.035
4. [4]
  Y. Zhang, J. Shang, H. Li, et al., Chin. Chem. Lett. 31 (2020) 1276-1280. doi: 10.1016/j.cclet.2019.10.039
5. [5]
  C.Y. Jia, F. Wang, G.F. Hao, G.F. Yang, J. Chem. Inf. Model. 59 (2019) 630-635. doi: 10.1021/acs.jcim.8b00843
6. [6]
  S. Zhou, Y. Gu, M. Liu, et al., J. Agric. Food Chem. 62 (2014) 11054-11061. doi: 10.1021/jf503513n
7. [7]
  J.E. Casida, Chem. Res. Toxicol. 28 (2015) 560-566. doi: 10.1021/tx500520w
8. [8]
  G.P. Lahm, T.P. Selby, J.H. Frendenberger, et al., Bioorg. Med. Chem. Lett. 15 (2005) 4898-4906. doi: 10.1016/j.bmcl.2005.08.034
9. [9]
  J.F. Zhang, J.Y. Xu, B.L. Wang, et al., J. Agric. Food Chem. 60 (2012) 7565-7572. doi: 10.1021/jf302446c
10. [10]
  M. Tohnishi, H. Nakao, T. Furuya, et al., J. Pestic. Sci. 30 (2005) 354-360. doi: 10.1584/jpestics.30.354
11. [11]
  G.P. Lahm, T.M. Stevenson, T.P. Selby, et al., Bioorg. Med. Chem. Lett. 17 (2007) 6274-6279. doi: 10.1016/j.bmcl.2007.09.012
12. [12]
  K.A. Hughes, G.P. Lahm, T.P. Selby, T.M. Stevenson, WO 2004067528 A1, 2004.
13. [13]
  G.P. Lahm, D. Cordova, J.D. Barry, Bioorg. Med. Chem. 17 (2009) 4127-4133. doi: 10.1016/j.bmc.2009.01.018
14. [14]
  T. Koyanagi, K. Nakamoto, W.O. 2008155990 A1, 2008.
15. [15]
  J.E. Silva, C.P.O. Assis, L.M.S. Ribeiro, H.A.A. Siqueira, J. Econ. Entomol. 109 (2016) 2190-2195. doi: 10.1093/jee/tow161
16. [16]
  X. Wang, Y. Wu, J. Econ. Entomol. 105 (2012) 1019-1023. doi: 10.1603/EC12059
17. [17]
  T. Lai, J. Li, J. Su, Pestic. Biochem. Physiol. 101 (2011) 198-205. doi: 10.1016/j.pestbp.2011.09.006
18. [18]
  J. Almássy, L. Csernoch, P.P. Nánási, Toxicol. Sci. 171 (2019) 281. doi: 10.1093/toxsci/kfz061
19. [19]
  M. Mao, Y. Li, Q. Liu, et al., Bioorg. Med. Chem. Lett. 23 (2013) 42-46. doi: 10.1016/j.bmcl.2012.11.045
20. [20]
  R.G. Hall, O. Loiseleur, J. Pabba, et al., WO 200901026 A2, 2009.
21. [21]
  J.B. Liu, Y.X. Li, X.L. Zhang, et al., J. Agric. Food Chem. 64 (2016) 3697-3704. doi: 10.1021/acs.jafc.6b00380
22. [22]
  A.E. Koehler, B. Alig, A. Becker, et al., WO 2013092350 A1, 2013.
23. [23]
  B.L. Wang, H.W. Zhu, Y. Ma, et al., J. Agric. Food Chem. 61 (2013) 5483-5493. doi: 10.1021/jf4012467
24. [24]
  B.L. Wang, H.W. Zhu, Z.M. Li, et al. Pest Manag. Sci. 74 (2018) 726-736. doi: 10.1002/ps.4770
25. [25]
  Y. Zhang, H. Zhu, J. Shang, B. Wang, Z. Li, Chin. J. Org. Chem. 39 (2019) 861-866. doi: 10.6023/cjoc201808033
26. [26]
  B.L. Wang, H.W. Zhu, Z.M. Li, Pest Manag. Sci. 75 (2019) 3273-3281. doi: 10.1002/ps.5449
27. [27]
  A.K. Sarmah, A.J. Sabadie, J. Agric. Food Chem. 50 (2002) 6253-6265. doi: 10.1021/jf025575p
28. [28]
  J. Huang, H.M. Ayad, P.R. Timmons, US 5360910 A, 1994.
29. [29]
  P. Timmons, R. Outcalt, S. Cramp, et al., EP 372982 A2, 1990.
30. [30]
  D.E. Mathre, J. Agric. Food Chem. 19 (1971) 869-871. doi: 10.1021/jf60177a040
31. [31]
  W. Ando, Sulfur. Rep. 1 (1981) 147-207. doi: 10.1080/17415998109408001
32. [32]
  P. Devendar, G.F. Yang, Topics Curr. Chem. 375 (2017) 82-126. doi: 10.1007/s41061-017-0169-9
33. [33]
  S.R. Byeon, Y.J. Jin, S.J. Lim, et al., Bioorg. Med. Chem. Lett. 17 (2007) 4022-4025. doi: 10.1016/j.bmcl.2007.04.079
34. [34]
  M.Z. Mao, H.Y. Wang, W. Wang, et al., Phosphorus Sulfur. Silic. Relat. Elem. 192 (2017) 42-46. doi: 10.1080/10426507.2016.1224876
35. [35]
  K.T. Waghmode, P.K. Shinde, Der. Pharma. Chem., 9 (2017) 47-49.
36. [36]
  L. Thomas, A. Gupta, V. Gupta, J. Fluor. Chem. 122 (2003) 207-213. doi: 10.1016/S0022-1139(03)00092-7
37. [37]
  B. Wang, H. Wang, H. Liu, et al., Chin. Chem. Lett. 31 (2020), 1276-1280. doi: 10.1364/ol.388722
38. [38]
  R. Sun, Y. Li, L. Xiong, Y. Liu, Q. Wang, J. Agric. Food Chem. 59 (2011) 4851-4859. doi: 10.1021/jf200395g
39. [39]
  X. Yu, Y. Liu, Y. Li, Q. Wang, J. Agric. Food Chem. 64 (2016) 3034-3040. doi: 10.1021/acs.jafc.6b00645
40. [40]
  Y. Xie, Y. Li, S. Zhou, et al., Synlett. 2018, 29, 340-343. doi: 10.1055/s-0036-1591496
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2. [2]
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