Citation: Wei Zhang, Shengxin Guo, Lijiao Yu, Ya Wang, Yonggui Robin Chi, Jian Wu. Piperazine: Its role in the discovery of pesticides[J]. Chinese Chemical Letters, ;2023, 34(8): 108123. doi: 10.1016/j.cclet.2022.108123 shu

Piperazine: Its role in the discovery of pesticides

Wei Zhang ^a ,
Shengxin Guo ^a ,
Lijiao Yu ^a ,
Ya Wang ^a ,
Yonggui Robin Chi ^{a, b, *,} ,
Jian Wu ^{a, *,}

a.
National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China
b.
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

robinchi@ntu.edu.sg

jwu6@gzu.edu.cn

Received Date: 13 October 2022
Revised Date: 26 December 2022
Accepted Date: 28 December 2022
Available Online: 29 December 2022

Figures(7)

Derivatives of piperazine, which is one of the most important heterocycles, are often used as linkers to connect active substructures that show promising bioactivities, especially in the field of agrochemicals. From 2000 to 2022, many piperazine-containing compounds were found to exhibit excellent activities against fungi, bacteria, insects, plant viruses, and weeds and have also been used as plant growth regulators. Currently, the development of novel pesticides to prevent the invasion of crop pathogens and ensure the quality and yields of crops is still needed. We herein investigated and summarized the role that piperazine plays in the discovery of pesticides to provide a comprehensive summary of the broad activities of piperazine derivatives in agricultural applications and offer a potential reference for novel pesticide design using piperazine-containing compounds. Moreover, structure–activity relationships (SARs) analyses of bioactive piperazine-containing compounds are also discussed for a deeper understanding.
- Piperazine,
- Innovation of pesticides,
- Activity,
- Research review,
- Structure–activity relationship
1. [1]
  D.I. Bugaenko, Chem. Heterocycl. Compd. 53 (2017) 1277–1279. doi: 10.1007/s10593-018-2205-2
2. [2]
  V.R. Solomon, C. Hu, H. Lee, Bioorg. Med. Chem. 18 (2010) 1563–1572. doi: 10.1016/j.bmc.2010.01.001
3. [3]
  M. Kimura, T. Masuda, K. Yamada, et al., Bioorg. Med. Chem. Lett. 14 (2004) 4287–4290. doi: 10.1016/j.bmcl.2004.05.091
4. [4]
  A. Garg, A. Kumar, V. Singh, et al., J. Cardiovasc. Dis. Res. 12 (2021) 686–695.
5. [5]
  B.N. Acharya, R. Ghorpade, K.P. Singh, D. Kumar, S. Nayak, Monatsh. Chem. 152 (2021) 357–366. doi: 10.1007/s00706-021-02752-4
6. [6]
  S. Elliott, Drug Test. Anal. 3 (2011) 430–438. doi: 10.1002/dta.307
7. [7]
  M. Borzsonyi, A. Pinter, G. Torok, A. Surjan, L. Nadasdi, IARC Sci. Publ. 19 (1978) 477–484.
8. [8]
  G. Mouriquand, E. Roman, J. Coisnard, J. Med. Lyon 32 (1951) 189–195.
9. [9]
  A.K. Rathi, R. Syed, H.S. Shin, R.V. Patel, Expert Opin. Ther. Pat. 26 (2016) 777–797. doi: 10.1080/13543776.2016.1189902
10. [10]
  E. Lacivita, M. Leopoldo, P. De Giorgio, F. Berardi, R. Perrone, Bioorg. Med. Chem. 17 (2009) 1339–1344. doi: 10.1016/j.bmc.2008.12.015
11. [11]
  S.J. Matthews, Conn. Med. 42 (1978) 509–510.
12. [12]
  X.J. Liu, T.T. Wang, Y.L. Zhong, X. Wang, J. Pharm. Sci. 30 (2013) 253–255. doi: 10.1007/s11712-013-9319-0
13. [13]
  A. Les, K. Badowska-Roslonek, M. Laszcz, et al., Acta Pol. Pharm. 67 (2010) 151–157.
14. [14]
  N.S. Gunasekara, C.M. Spencer. CNS Drugs 9 (1998) 325–340. doi: 10.2165/00023210-199809040-00007
15. [15]
  R.V. Patel, S.W. Park, Mini-Rev. Med. Chem. 13 (2013) 1579–1601. doi: 10.2174/13895575113139990073
16. [16]
  Q.S. Zhang, H.M. Zhang, B.N. Guo, Fine Chem. 23 (2006) 435–438 (in Chinese).
17. [17]
  J.B. Bourke, T.R. Nelsen, D. Eichler, J. Agric. Food Chem. 25 (1977) 36–39. doi: 10.1021/jf60209a023
18. [18]
  K.E. Gettys, Z. Ye, M. Dai, Synthesis (Mass) 49 (2017) 2589–2604. doi: 10.1055/s-0036-1589491
19. [19]
  S.S. Sajadikhah, M. Nassiri, Chem. Heterocycl. Compd. 57 (2021) 905–907. doi: 10.1007/s10593-021-02998-0
20. [20]
  R.H. Zhang, H.Y. Guo, H. Deng, J. Li, Z.S. Quan, J. Enzyme Inhib. Med. Chem. 36 (2021) 1165–1197. doi: 10.1080/14756366.2021.1931861
21. [21]
  P.P. Chen, Z.Y. Zhou, Y.F. Zhou, et al., CN Patent 114262273, 2022.
22. [22]
  X.W. Wang, H. Han, W.Z. Tang, Q.J. Guo, CN Patent 114315593, 2022.
23. [23]
  N.A. Meanwell, O. Loiseleur, J. Agric. Food Chem. 70 (2022) 10942–10971. doi: 10.1021/acs.jafc.2c00726
24. [24]
  N.A. Meanwell, O. Loiseleur, J. Agric. Food Chem. 70 (2022) 10972–11004. doi: 10.1021/acs.jafc.2c00729
25. [25]
  F. Han, R. Yan, M. Zhang, et al., Nat. Prod. Res. 34 (2020) 1282–1287. doi: 10.1080/14786419.2018.1556656
26. [26]
  S.C. Deng, X.J. Li, X. Zhu, et al., Chin. J. Pestic. Sci. 23 (2021) 77–86. doi: 10.1117/12.2605808
27. [27]
  H.B. Fang, Z.F. Chen, X.W. Hua, et al., Med. Chem. Res. 31 (2022) 485–496. doi: 10.1007/s00044-022-02852-8
28. [28]
  M.H. Wang, H.B. Zhu, Z. Peng, L.Z. Xu, CN Patent 108675991, 2018.
29. [29]
  S. Yang, P.Y. Wang, M. Xiang, et al., CN Patent 110776548, 2020.
30. [30]
  Q. Zhou, X.M. Tang, S. Chen, et al., J. Agric. Food Chem. 70 (2022) 1029–1036. doi: 10.1021/acs.jafc.1c05933
31. [31]
  B.E.D.M. El-Gendy, M.E. Rateb, Bioorg. Med. Chem. Lett. 25 (2015) 3125–3128. doi: 10.1016/j.bmcl.2015.06.010
32. [32]
  J.L. Xie, W.T. Xu, H.J. Song, et al., J. Agric. Food Chem. 68 (2020) 5555–5571. doi: 10.1021/acs.jafc.0c00875
33. [33]
  Q.M. Wang, J.M. Guo, Y.X. Liu, et al., CN Patent 113024538, 2021.
34. [34]
  B.L. Wang, Z.M. Li, Y. Zhang, CN Patent 106749262, 2017.
35. [35]
  Y. Zhang, Y.Z. Zhan, Y. Ma, et al., Chin. Chem. Lett. 29 (2018) 441–446. doi: 10.1016/j.cclet.2017.08.035
36. [36]
  Y. Zhang, Z. Li, H. Song, B. Wang, Chin. J. Chem. 36 (2018) 635–638. doi: 10.1002/cjoc.201800110
37. [37]
  B.L. Wang, Y.X. Shi, Y. Ma, et al., J. Agric. Food Chem. 58 (2010) 5515–5522. doi: 10.1021/jf100300a
38. [38]
  L.Y. Zhang, B.L. Wang, Y.Z. Zhan, et al., Chin. Chem. Lett. 27 (2016) 163–167. doi: 10.1016/j.cclet.2015.09.015
39. [39]
  D.D. Brown, S.Z. Siddiqui, M.D. Kaji, S.G. Forrester, Vet. Parasitol. 185 (2012) 201–209. doi: 10.1016/j.vetpar.2011.10.006
40. [40]
  M.T. Hoekenga, Am. J. Trop. Med. Hyg. 4 (1955) 1088–1090. doi: 10.4269/ajtmh.1955.4.1088
41. [41]
  J.G. Samaritoni, D.A. Demeter, J.M. Gifford, et al., J. Agric. Food Chem. 51 (2003) 3035–3042. doi: 10.1021/jf021185r
42. [42]
  Z.B. Li, Z. Chen, A.L. Chen, et al., Chin. J. Pestic. Sci. 17 (2015) 136–142.
43. [43]
  Y. Xie, Y. Xu, C.L. Liu, et al., Pest Manag. Sci. 73 (2017) 945–952. doi: 10.1002/ps.4369
44. [44]
  Z.Z. Zheng, A.L. Dai, Z.C. Jin, Y.R. Chi, J. Wu, J. Agric. Food Chem. 70 (2022) 11019–11030. doi: 10.1021/acs.jafc.1c08383
45. [45]
  M.H. Wang, Z. Peng, H.Q. Cui, J.Q. Cui, L.Z. Xu, CN Patent 108822082, 2018.
46. [46]
  M.H. Wang, L.Z. Xu, Z. Peng, H.Q. Cui, J.X. Sun, CN Patent 109336882, 2019.
47. [47]
  Q.M. Wang, H.J. Song, L.L. Li, et al., CN Patent 110759896, 2020.
48. [48]
  H. Li, H. Liu, Y. Zhang, et al., Chin. Chem. Lett. 32 (2021) 2893–2898. doi: 10.1016/j.cclet.2021.02.002
49. [49]
  G. Steiner, T. Schmidt, M. Kordes, et al., WO Patent 2004080170, 2004.
50. [50]
  C.H. Lee, H.W. Kim, H.S. Lee, Pest Manag. Sci. 65 (2009) 704–710. doi: 10.1002/ps.1728
51. [51]
  M.Y. Cai, Z. Li, F. Fan, et al., J. Agric. Food Chem. 58 (2010) 2624–2629. doi: 10.1021/jf902640u
52. [52]
  J. Suzuki, A. Ootaka, S. Onoue, M. Onoue, J. Pestic. Sci. 46 (2021) 189–197. doi: 10.1584/jpestics.d21-007
53. [53]
  A. Jain, J. Chaudhary, H. Khaira, B. Chopra, A. Dhingra, Drug Res. 71 (2021) 62–72. doi: 10.1055/a-1323-2813
54. [54]
  R.R. Kumar, B. Sahu, S. Pathania, et al., ChemMedChem 16 (2021) 1878–1901. doi: 10.1002/cmdc.202100045
55. [55]
  R.C.K. Reddy, S. Rasheed, D.S. Rao, et al., Sci. World J. 2013 (2013) 682603.
56. [56]
  V. Nagalakshmamma, M. Venkataswamy, C. Pasala, et al., Bioorg. Chem. 102 (2020) 104084. doi: 10.1016/j.bioorg.2020.104084
57. [57]
  Q. Wu, Z.C. Wang, T. Yang, Int. J. Mol. Sci. 30 (2014) 273–279. doi: 10.1179/1433075X13Y.0000000134
58. [58]
  D.H. Jiang, J.X. Chen, N.N. Zan, et al., J. Agric. Food Chem. 69 (2021) 12126–12134. doi: 10.1021/acs.jafc.1c02467
59. [59]
  D.Y. Hu, Q.Q. Wan, S. Yang, et al., J. Agric. Food Chem. 56 (2008) 998–1001. doi: 10.1021/jf072394k
60. [60]
  D.G. Zhou, D.D. Xie, F.C. He, B.A. Song, D.Y. Hu, Bioorg. Med. Chem. Lett. 28 (2018) 2091–2097. doi: 10.1016/j.bmcl.2018.04.042
61. [61]
  X.H. Gan, T. Yuan, D. Liu, B.A. Song, D.Y. Hu, CN Patent 113461639, 2021.
62. [62]
  C.Y. Li, R.J. Song, S.Q. He, et al., J. Agric. Food Chem. 70 (2022) 7375–7386. doi: 10.1021/acs.jafc.2c01813
63. [63]
  G.M. Stoilkova, P. Yonova, K. Ananieva, Plant Growth Regul. 72 (2014) 303–312. doi: 10.1007/s10725-013-9861-0
64. [64]
  Y. Zhang, X.H. Liu, Y.Z. Zhan, et al., Bioorg. Med. Chem. Lett. 26 (2016) 4661–4665. doi: 10.1016/j.bmcl.2016.08.059
65. [65]
  B.L. Wang, L.Y. Zhang, X.H. Liu, et al., Bioorg. Med. Chem. Lett. 27 (2017) 5457–5462. doi: 10.1016/j.bmcl.2017.10.065
66. [66]
  B.L. Wang, Y.X. Shi, Y.Z. Zhan, et al., Chin. J. Chem. 33 (2015) 1124–1134. doi: 10.1002/cjoc.201500436
67. [67]
  A. Foroumadi, F. Soltani, M.H. Moshafi, R. Ashraf-Askari, Farmaco 58 (2003) 1023–1028. doi: 10.1016/S0014-827X(03)00191-5
68. [68]
  A. Foroumadi, S. Ghodsi, S. Emami, et al., Bioorg. Med. Chem. Lett. 16 (2006) 3499–3503. doi: 10.1016/j.bmcl.2006.03.103
69. [69]
  B.B. Lohray, V.B. Lohray, B.K. Srivastava, et al., Bioorg. Med. Chem. Lett. 16 (2006) 1557–1561. doi: 10.1016/j.bmcl.2005.12.025
1. [1]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
2. [2]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
3. [3]
  Zhiliang Li . An Overview of Research on the History of Catalysis Science in China. University Chemistry, 2024, 39(7): 398-404. doi: 10.3866/PKU.DXHX202310101
4. [4]
  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
5. [5]
  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
6. [6]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
7. [7]
  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
8. [8]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
9. [9]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
10. [10]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
11. [11]
  Hongrui Zhang , Miaoying Cui , Yongjie Lv , Yongfang Rao , Yu Huang . A short review on research progress of ZnIn₂S₄-based S-scheme heterojunction: Improvement strategies. Chinese Chemical Letters, 2025, 36(4): 110108-. doi: 10.1016/j.cclet.2024.110108
12. [12]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
13. [13]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
14. [14]
  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
15. [15]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
16. [16]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
17. [17]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
18. [18]
  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
19. [19]
  Meng Wang , Yan Zhang , Yunbo Yu , Wenpo Shan , Hong He . High-temperature calcination dramatically promotes the activity of Cs/Co/Ce-Sn catalyst for soot oxidation. Chinese Chemical Letters, 2025, 36(1): 109928-. doi: 10.1016/j.cclet.2024.109928
20. [20]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(264)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142