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]
  Yi-Ru Bai , Qing-Chuan Duan , Dong-Jie Seng , Ying Xu , Hong-Bo Ren , Jie Zhang , Dan-Dan Shen , Li Yang , Hong-Min Liu , Shuo Yuan . A comprehensive review of small molecule drugs approved by the FDA in 2024: Advance and prospect. Chinese Chemical Letters, 2025, 36(10): 111025-. doi: 10.1016/j.cclet.2025.111025
7. [7]
  Haoran Xu , Jiaqi Fan , Jiwei Liu , Qi Wei , Ruoshui Li , Pengcheng Yuan , Bing Xiao , Ying Piao , Wenjing Sun , Jiajia Xiang , Shiqun Shao , Zhuxian Zhou , Youqing Shen , Nigel K.H. Slater , Jianbin Tang . Tetra-branched ionizable lipids enhance the stability and transfection efficiency of lipid nanoparticles for mRNA delivery. Chinese Chemical Letters, 2025, 36(11): 110833-. doi: 10.1016/j.cclet.2025.110833
8. [8]
  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
9. [9]
  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
10. [10]
  Bofei JIA , Zhihao LIU , Zongyuan GAO , Shuai ZHOU , Mengxiang WU , Qian ZHANG , Xiamei ZHANG , Shuzhong CHEN , Xiaohan YANG , Yahong LI . Cu(Ⅱ) and Cu(Ⅰ) complexes based on derivatives of imidazo[1,5-a]pyridine: Synthesis, structures, in situ metal-ligand reactions, and catalytic activity. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 1020-1036. doi: 10.11862/CJIC.20240317
11. [11]
  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
12. [12]
  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
13. [13]
  Wen-Rui Li , Ru-Bing Wang , Huiqiang Wang , Jin-Yao Yong , Yu-Huan Li , Shi-Shan Yu , Shuang-Gang Ma . Ring-reorganization strategy for asymmetric synthesis of sesquiterpenoid illihenin A and its antiviral activity evaluation. Chinese Chemical Letters, 2025, 36(11): 110945-. doi: 10.1016/j.cclet.2025.110945
14. [14]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
15. [15]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
16. [16]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
17. [17]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
18. [18]
  Haiying Jiang , Liuhong Song , Yangyang Cheng , Kefen Yue , Mingli Peng , Huilin Guo . Ph―C≡C―Cu_2.5的力致变色现象探究——推荐一个物理化学实验. University Chemistry, 2025, 40(8): 249-254. doi: 10.12461/PKU.DXHX202410003
19. [19]
  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
20. [20]
  Xiaomeng Hu , Jie Yu , Lijie Sun , Linfeng Zhang , Wei Zhou , Dongpeng Yan , Xinrui Wang . Synthesis of an AVB@ZnTi-LDH composite with synergistically enhance UV blocking activity and high stability for potential application in sunscreen formulations. Chinese Chemical Letters, 2024, 35(11): 109466-. doi: 10.1016/j.cclet.2023.109466

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