Citation: Zhang Yan, Shang Junfeng, Li Huan, Liu Hang, Song Haibin, Wang Baolei, Li Zhengming. Synthesis of novel N-pyridylpyrazole derivatives containing 1, 2, 4-oxadiazole moiety via 1, 3-dipolar cycloaddition and their structures and biological activities[J]. Chinese Chemical Letters, ;2020, 31(5): 1276-1280. doi: 10.1016/j.cclet.2019.10.039 shu

Synthesis of novel N-pyridylpyrazole derivatives containing 1, 2, 4-oxadiazole moiety via 1, 3-dipolar cycloaddition and their structures and biological activities

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

nkwbl@nankai.edu.cn

nkzml@vip.163.com

Received Date: 9 September 2019
Revised Date: 28 October 2019
Accepted Date: 30 October 2019
Available Online: 6 November 2019

Figures(9)

A series of novel 1, 2, 4-oxadiazole-containing N-pyridylpyrazole derivatives 12a-h were efficiently synthesized with pivaldehyde, pyridylpyrazole carboxylic acid and arylamine as raw materials via 1, 3-dipolar cycloaddition. Their structures were identified by melting points, ¹H NMR, ¹³C NMR and elemental analysis or HRMS. The exploration on the single-crystal structures of 12c and 12g revealed the stereochemical and substituent oriental characteristics, and the relevance of the structure and the reaction activity of this type of compounds. The preliminary bioassays indicated that several compounds had good insecticidal activities, among which 12c showed a lethality rate of 80% towards Mythimna separata Walker at 200 μg/mL; some of the compounds exhibited favorable fungicidal activities at 50 μg/mL against Physalospora piricola, Rhizoctonia cereal, Sclerotinia sclerotiorum, etc. Among which, 12a, 12b, 12c and 12h could be considered as new fungicidal leading compounds for further structural optimization. These discoveries along with the structure-activity relationship analysis in this paper will provide useful guidance for the innovative studies on new pyridylpyrazole derivatives and their applications in agrochemical area.
- N-Pyridylpyrazole derivatives,
- 1, 2, 4-Oxadiazole,
- 1, 3-Dipolar cycloaddition,
- Insecticidal activity,
- Fungicidal activity,
- Structure-activity relationship
1. [1]
  E.C. Oerke, H.W. Dehne, Crop Prot. 23(2004) 275-285. doi: 10.1016/j.cropro.2003.10.001
2. [2]
  X.H. Liu, Y.M. Fang, F. Xie, et al., Pest Manag. Sci. 73(2017) 1900-1907. doi: 10.1002/ps.4556
3. [3]
  Q. Hou, Y. Jing, X. Shao, Chin. Chem. Lett. 28(2017) 1723-1726. doi: 10.1016/j.cclet.2017.05.016
4. [4]
  Y. Zhang, Y. Feng, Z. Li, et al., Chin. Chem. Lett. 28(2017) 1228-1231. doi: 10.1016/j.cclet.2017.04.003
5. [5]
  W. Hidalgo, M. Cano, M. Arbelaez, et al., Pest Manag. Sci. 72(2016) 796-800. doi: 10.1002/ps.4055
6. [6]
  F.Y. Li, X.F. Guo, Z.J. Fan, et al., Chin. Chem. Lett. 26(2015) 1315-1318. doi: 10.1016/j.cclet.2015.05.040
7. [7]
  Y. Ren, Q. Sun, Z. Yuan, et al., Chin. Chem. Lett. 30(2019) 1233-1236. doi: 10.1016/j.cclet.2019.03.029
8. [8]
  Y. Zhang, Y.Z. Zhan, Y. Ma, et al., Chin. Chem. Lett. 29(2018) 441-446. doi: 10.1016/j.cclet.2017.08.035
9. [9]
  X. Zhu, W. Jiang, W. Cui, et al., Chin. Chem. Lett. 30(2019) 1133-1136. doi: 10.1016/j.cclet.2019.02.022
10. [10]
  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
11. [11]
  J. Wu, B.A. Song, D.Y. Hu, et al., Pest Manag. Sci. 68(2012) 801-810. doi: 10.1002/ps.2329
12. [12]
  K.A. Hughes, G.P. Lahm, T.P. Selby, et al., Patent, WO 2004067528, 2004.
13. [13]
  W.L. Dong, J.Y. Xu, L.X. Xiong, et al., Molecules 17(2012) 10414-10428. doi: 10.3390/molecules170910414
14. [14]
  T. Yan, S. Yu, P. Liu, et al., Chin. J. Chem. 30(2012) 919-923. doi: 10.1002/cjoc.201100347
15. [15]
  B.L. Wang, H.W. Zhu, Z.M. Li, et al., Pest Manag. Sci. 74(2018) 726-736. doi: 10.1002/ps.4770
16. [16]
  Y. Zhang, H. Zhu, J. Shang, et al., Chin. J. Org. Chem. 39(2019) 861-866. doi: 10.6023/cjoc201808033
17. [17]
  B.L. Wang, H.W. Zhu, Y. Ma, et al., J. Agric. Food Chem. 61(2013) 5483-5493. doi: 10.1021/jf4012467
18. [18]
  A.C. Liu, J.L. Feng, X.L. He, et al., Agrochemicals 53(2014) 561-563.
19. [19]
  J.N. Kim, E.K. Ryu, J. Org. Chem. 57(1992) 1088-1092. doi: 10.1021/jo00030a011
20. [20]
  N.L. Chavana, N.H. Naika, S.K. Nayak, et al., Arkivoc 2010(2010) 248-255.
21. [21]
  K.M. Jiang, U. Luesakul, S.Y. Zhao, et al., Omega 2(2017) 3123-3134. doi: 10.1021/acsomega.7b00490
22. [22]
  D.K. Miller, C.A. Bailey, R.E. Sammelson, Synthesis 47(2015) 2791-2798. doi: 10.1055/s-0034-1378737
23. [23]
  J. Li, D. Wu, X. Xu, et al., Bioorg. Med. Chem. Lett. 26(2016) 3064-3066. doi: 10.1016/j.bmcl.2016.05.016
24. [24]
  J. Xu, W. Dong, L. Xiong, et al., Chin. J. Chem. 27(2009) 2007-2012. doi: 10.1002/cjoc.200990337
25. [25]
  B. Wang, H. Wang, H. Liu, et al., Chin. Chem. Lett. 31(2020) 739-745. doi: 10.1016/j.cclet.2019.07.064
26. [26]
  B. Wang, Y. Shi, Y. Zhan, et al., Chin. J. Chem. 33(2015) 1124-1134. doi: 10.1002/cjoc.201500436
27. [27]
  B.L. Wang, H.W. Zhu, Z.M. Li, et al., Pest Manag. Sci. 75(2019) 3273-3281. doi: 10.1002/ps.5449
28. [28]
  Y. Zhou, Q. Feng, F. Di, et al., Bioorg. Med. Chem. 21(2013) 4968-4975. doi: 10.1016/j.bmc.2013.06.060
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