Citation: Huan Li, Hang Liu, Yan Zhang, Na Yang, Lixia Xiong, Zhengming Li, Baolei Wang. Synthesis, insecticidal activities, and SAR studies of novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives[J]. Chinese Chemical Letters, ;2021, 32(9): 2893-2898. doi: 10.1016/j.cclet.2021.02.002 shu

Synthesis, insecticidal activities, and SAR studies of novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives

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

Corresponding author: Baolei Wang, nkwbl@nankai.edu.cn
Received Date: 18 November 2020
Revised Date: 21 December 2020
Accepted Date: 1 February 2021
Available Online: 4 February 2021

Figures(7)

Diamide compounds such as chlorantraniliprole, a famous anthranilic diamide insecticide targeting the insect ryanodine receptor (RyR), have received continuous attention in pesticide research during the past 15 years owing to their excellent insecticidal potentials. With the aim of discovering new heterocyclic pesticides used for crop protection, based on the structural information of compound M from the reported pharmacophore-based virtual screening for RyR insecticides and diamide compound, a series of new heterocyclic mono-, di-, and tri-amide derivatives containing piperazine moiety have been synthesized in this paper. The new compounds were identified and confirmed by melting point, ¹H NMR, ¹³C NMR and HRMS. Compound M was firstly validated for insecticidal activities, and the new synthesized compounds were all made comprehensive insecticidal evaluations against diamondback moth and oriental armyworm. The bioassay results showed that some of the compounds exhibit favorable insecticidal potentials, particularly some novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives such as 8g, 14a, 15a, 15g, 15i, 15j, 15k, 15l, and 15m could be used as new insecticidal leading structures for further study (e.g., towards diamondback moth, 15i-15m LC₅₀: 0.0022−0.0081 mg/L). The structure-activity relationships of the compounds discussed in detail provide useful guidance for further design and development of new insecticides.
- Heterocyclic amide derivatives,
- Piperazine-containing compounds,
- Synthesis,
- Insecticidal activity,
- Structure-activity relationship
1. [1]
  C. Lamberth, J. Dinges, The Significance of Heterocycles for Pharmaceuticals and Agrochemicals, in: C. Lamberth, J. Dinges (Eds.), Bioactive Heterocyclic Compound Classes -- Agrochemicals, Wiley-VCH, Weinheim, 2012, pp. 3-20
2. [2]
  Q. Hou, Y. Jing, X. Shao, Chin. Chem. Lett. 28 (2017) 1723-1726 doi: 10.1016/j.cclet.2017.05.016
3. [3]
  Y. Zhang, J. Shang, H. Li, et al., Chin. Chem. Lett. 31 (2020) 1276-1280 doi: 10.1016/j.cclet.2019.10.039
4. [4]
  E.F. Rogers, F.R. Koniuszy, J. Shavel, K. Folkers, J. Am. Chem. Soc. 70 (1948) 3086-3088 doi: 10.1021/ja01189a074
5. [5]
  M. Tohnishi, H. Nakao, T. Furuya, et al., J. Pestic. Sci. 30 (2005) 354-360 doi: 10.1584/jpestics.30.354
6. [6]
  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
7. [7]
  K.A. Hughes, G.P. Lahm, T.P. Selby, T.M. Stevenson, Patent, WO 2004067528, 2004.
8. [8]
  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
9. [9]
  X. Wang, Y. Wu, J. Econ. Entomol. 105 (2012) 1019-1023 doi: 10.1603/EC12059
10. [10]
  T. Lai, J. Li, J. Su, Pestic. Biochem. Physiol. 101 (2011) 198-205 doi: 10.1016/j.pestbp.2011.09.006
11. [11]
  T. Koyanagi, K. Nakamoto, Patent, WO 2008155990, 2008.
12. [12]
  T.P. Selby, G.P. Lahm, T.M. Stevenson, Pest Manag. Sci. 73 (2017) 658-665 doi: 10.1002/ps.4308
13. [13]
  T. Sindhu, T. Venkatesan, G.R. Gracy, S.K. Jalali, A. Rai, Biochem. Eng. J. 121 (2017) 59-72 doi: 10.1016/j.bej.2017.01.013
14. [14]
  S. Liang, C.M. Liu, Y.S. Jin, Q.Q. He, Chin. J. Med. Chem. 14 (2004) 71-75
15. [15]
  D.H. Jiang, M. Huang, Chem. Reag. 34 (2012) 797-799
16. [16]
  H. Foks, M. Janowiec, Z. Zwolska, E. Augustynowicz-Kope, Phosphorus Sulfur Silicon Relat. Elem. 180 (2005) 537-543 doi: 10.1080/104265090517280
17. [17]
  Q. Wu, Z.C. Wang, X. Wei, W. Xue, Chin. J. Synth. Chem. 22 (2014) 429-434
18. [18]
  V. Amarnath, K. Amarnath, J. Org. Chem. 60 (1995) 301-307 doi: 10.1021/jo00107a006
19. [19]
  B. -L. Wang, H. -W. Zhu, Z. -M. Li, et al., Pest Manag. Sci. 74 (2018) 726-736 doi: 10.1002/ps.4770
20. [20]
  B. Wang, H. Wang, H. Liu, et al., Chin. Chem. Lett. 31 (2020) 739-745 doi: 10.1016/j.cclet.2019.07.064
21. [21]
  B. -L. Wang, Y. -X. Shi, Y. Ma, et al., J. Agric. Food Chem. 58 (2010) 5515-5522 doi: 10.1021/jf100300a
22. [22]
  Y. Zhang, Y. Zhan, Y. Ma, et al., Chin. Chem. Lett. 29 (2018) 441-446 doi: 10.1016/j.cclet.2017.08.035
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
3. [3]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
4. [4]
  A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
5. [5]
  Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094
6. [6]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
7. [7]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
8. [8]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
9. [9]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
10. [10]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
11. [11]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
12. [12]
  Chen Lian , Si-Han Zhao , Hai-Lou Li , Xinhua Cao . A giant Ce-containing poly(tungstobismuthate): Synthesis, structure and catalytic performance for the decontamination of a sulfur mustard simulant. Chinese Chemical Letters, 2024, 35(10): 109343-. doi: 10.1016/j.cclet.2023.109343
13. [13]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
14. [14]
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15. [15]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
16. [16]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
17. [17]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
18. [18]
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19. [19]
  Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
20. [20]
  Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758

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