Citation: Zhang Dong-Dong, Cui Shu-Xia, Xu Zhi-Ping, Li Dong-Mei, Tian Zhong-Zhen. Synthesis and insecticidal activities of novel bridged-neonicotinoids[J]. Chinese Chemical Letters, ;2017, 28(8): 1743-1745. doi: 10.1016/j.cclet.2017.05.002 shu

Synthesis and insecticidal activities of novel bridged-neonicotinoids

a.
Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China
b.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Tian Zhong-Zhen, chm_tianzz@ujn.edu.cn
Received Date: 7 March 2017
Revised Date: 24 April 2017
Accepted Date: 4 May 2017
Available Online: 10 August 2017

Figures(3)

A series of novel bridged-neonicotinoid analogues were designed and synthesized, which were constructed by starting material 8 with cyclopentenone or cyclohexenone in the presence of catalyst aluminium chloride. All of the compounds were characterized and confirmed by ¹H NMR, ¹³C NMR, HRMS and IR. The bioassay tests showed that compounds 5 and 6a showed higher bioactivities than imidacloprid against Aphis craccivora.
- Neonicotinoid Bridged compound,
- Insecticidal activity,
- Michael addition,
- Resistance
1. [1]
  Guan A., Liu C.L., Yang X.P., Dekeyser M.. Application of the intermediate derivatization approach in agrochemical discovery[J]. Chem. Rev., 2014,114:7079-7107. doi: 10.1021/cr4005605
2. [2]
  Li J., Ju X.L., Jiang F.C.. Pharmacophore model for neonicotinoid insecticides[J]. Chin. Chem. Lett., 2008,19:619-622. doi: 10.1016/j.cclet.2008.03.011
3. [3]
  Shen H.F., Chen X., Liao P.. Design synthesis, and insecticidal bioactivities evaluation of pyrrole-and dihydropyrrole-fused neonicotinoid analogs containing chlorothiazole ring[J]. Chin. Chem. Lett., 2015,26:509-512. doi: 10.1016/j.cclet.2015.03.017
4. [4]
  Tomizawa M., Casida J.E.. Molecular recognition of neoniconoid insecticide:the determinants of life or death[J]. Acc. Chem. Res., 2009,42:260-269. doi: 10.1021/ar800131p
5. [5]
  Shao X.S., Xia S.S., Durkin K.A., Casida J.E.. Insect nicotinic receptor interactions in vivo with neonicotinoid, organophosphorus and methylcarbamate insecticides and a synergist[J]. Proc. Natl. Acad. Sci. U. S. A., 2013,110:17273-17277. doi: 10.1073/pnas.1316369110
6. [6]
  Jeschke P., Nauen R., Schindler M., Elbert A.. Overview of the status and global strategy for neonicotinoids[J]. J. Agric. Food Chem., 2011,59:2897-2908. doi: 10.1021/jf101303g
7. [7]
  Jeschke P., Nauen R., Beck M.E.. Nicotinic acetylcholine receptor agonists:a milestone for modern crop protection[J]. Angew. Chem. Int. Ed., 2013,52:9464-9485. doi: 10.1002/anie.v52.36
8. [8]
  Elbert A., Nauen R.. Resistance of bemisia tabaci (Homoptera:aleyrodidae) to insecticides in southern Spain with special reference to neonicotinoids[J]. Pest. Manage. Sci., 2000,56:60-64. doi: 10.1002/(ISSN)1526-4998
9. [9]
  Rauch N., Nauen R.. Identification of biochemical markers linked to neonicotinoid cross-resistance in bemisia tabaci (Hemiptera:Aleyrodidae)[J]. Arch. Insect. Biochem. Physiol., 2003,54:165-176. doi: 10.1002/(ISSN)1520-6327
10. [10]
  Nauen R., Denholm I.. Resistance of insect pests to neonicotinoid insecticides:current status and future prospects[J]. Arch. Insect Biochem. Physiol., 2005,58:200-215. doi: 10.1002/(ISSN)1520-6327
11. [11]
  Sanada S., Morimura -, Sakumoto S., Ohtsu R.. Current status of insecticide resistance in the small brown planthopper Laodelphax striatellus, in Japan Taiwan, and Viatnam[J]. Appl. Entomol. Zool., 2011,46:65-73. doi: 10.1007/s13355-010-0009-7
12. [12]
  Zhu Y., Loso M.R., Watson G.B.. Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests[J]. J. Agric. Food Chem., 2011,59:2950-2957. doi: 10.1021/jf102765x
13. [13]
  Y. Zhu, R. B. Rogers, Insecticidal N-substituted sulfoximines, WO Patent 2006060029, (2006).
14. [14]
  P. Jeschke, R. , Velten, T. Schenke, et al. Substituted enaminocarbonyl compounds, WO Patent 2007115643, (2007).
15. [15]
  Zhang W.M., Barry J.D., Cordova D.. Discovery synthesis, and evaluation of N-substituted amino-2(5H)-oxazolones as novel insecticides activating nicotinic acetylcholine receptors[J]. Bioorg. Med. Chem. Lett., 2014,24:2188-2192. doi: 10.1016/j.bmcl.2014.03.037
16. [16]
  Yu H.B., Qin Z.F., Dai H.. Synthesis and insecticidal activity of Nsubstituted (1, 3-thiazole) alkyl sulfoximine derivatives[J]. J. Agric. Food Chem., 2008,56:11356-11360. doi: 10.1021/jf802802g
17. [17]
  M. R. Loso, B. M. Nugent, J. X. Huang, et al. Preparation of insecticidal Nsubstituted (6-haloalkylpyridin-3-yl)alkyl sulfoximines, WO Patent 2007095229, (2007).
18. [18]
  M. R. Loso, B. M. Nugent, J. X. Huang, Insecticidal N-substituted (Heteroaryl) cycloalkyl sulfoximines, WO Patent 2008027073, (2008).
19. [19]
  Y. M. Zhu, M. R. Loso, B. M. Nugent, J. X. Huang, R. B. Rogers, Multi-substituted pyridyl sulfoximines and their use as insecticides, WO Patent 2008057129, (2008).
20. [20]
  Shao X.S., Fu H., Xu X.Y.. Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid:Design, synthesis, crystal structure, and insecticidal activities[J]. J. Agric. Food. Chem., 2010,58:2696-2702. doi: 10.1021/jf902531y
21. [21]
  Shao X.S., Ye Z.J., Bao H.B.. Advanced research on cis-neonicotinoids[J]. CHIMIA, 2011,65:957-960. doi: 10.2533/chimia.2011.957
22. [22]
  Tian Z.Z., Shao X.S., Li Z., Qian X.H., Huang Q.C.. Synthesis:insecticidal activity and QSAR of novel nitromethylene neonicotinoids with tetrahydro-pyridine fixed cis configuration and exo-ring ether modification[J]. J. Agric. Food Chem., 2007,55:2288-2292. doi: 10.1021/jf063418a
1. [1]
  Yong-Dan Zhao , Yidan Wang , Rongrong Wang , Lina Chen , Hengtong Zuo , Xi Wang , Jihong Qiang , Geng Wang , Qingxia Li , Canqi Ping , Shuqiu Zhang , Hao Wang . Reversing artemisinin resistance by leveraging thermo-responsive nanoplatform to downregulating GSH. Chinese Chemical Letters, 2024, 35(6): 108929-. doi: 10.1016/j.cclet.2023.108929
2. [2]
  Yixuan Wang , Jiexin Li , Zhihao Shang , Chengcheng Feng , Jianmin Gu , Maosheng Ye , Ran Zhao , Danna Liu , Jingxin Meng , Shutao Wang . Wettability-driven synergistic resistance of scale and oil on robust superamphiphobic coating. Chinese Chemical Letters, 2024, 35(7): 109623-. doi: 10.1016/j.cclet.2024.109623
3. [3]
  Yuxin Li , Chengbin Liu , Qiuju Li , Shun Mao . Fluorescence analysis of antibiotics and antibiotic-resistance genes in the environment: A mini review. Chinese Chemical Letters, 2024, 35(10): 109541-. doi: 10.1016/j.cclet.2024.109541
4. [4]
  Shaoqing Du , Xinyong Liu , Xueping Hu , Peng Zhan . Targeting novel sites represents an effective strategy for combating drug resistance. Chinese Chemical Letters, 2025, 36(1): 110378-. doi: 10.1016/j.cclet.2024.110378
5. [5]
  Xiaofang Luo , Ye Wu , Xiaokun Zhang , Min Tang , Feiye Ju , Zuodong Qin , Gregory J Duns , Wei-Dong Zhang , Jiang-Jiang Qin , Xin Luan . Peptide-based strategies for overcoming multidrug-resistance in cancer therapy. Chinese Chemical Letters, 2025, 36(1): 109724-. doi: 10.1016/j.cclet.2024.109724
6. [6]
  Liping Zhao , Xixi Guo , Zhimeng Zhang , Xi Lu , Qingxuan Zeng , Tianyun Fan , Xintong Zhang , Fenbei Chen , Mengyi Xu , Min Yuan , Zhenjun Li , Jiandong Jiang , Jing Pang , Xuefu You , Yanxiang Wang , Danqing Song . Novel berberine derivatives as adjuvants in the battle against Acinetobacter baumannii: A promising strategy for combating multi-drug resistance. Chinese Chemical Letters, 2024, 35(10): 109506-. doi: 10.1016/j.cclet.2024.109506
7. [7]
  Guihuang Fang , Wei Chen , Hongwei Yang , Haisheng Fang , Chuang Yu , Maoxiang Wu . Improved performance of LiMn_0.8Fe_0.2PO₄ by addition of fluoroethylene carbonate electrolyte additive. Chinese Chemical Letters, 2024, 35(6): 108799-. doi: 10.1016/j.cclet.2023.108799
8. [8]
  Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
9. [9]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
10. [10]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
11. [11]
  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
12. [12]
  Yan Cheng , Hai-Quan Yao , Ya-Di Zhang , Chao Shi , Heng-Yun Ye , Na Wang . Nitrate-bridged hybrid organic-inorganic perovskites. Chinese Journal of Structural Chemistry, 2024, 43(9): 100358-100358. doi: 10.1016/j.cjsc.2024.100358
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  Yanbing Shen , Yuan Yuan , Yaxin Wang , Xiaonan Ma , Wensheng Yang , Yulan Chen . Dihydroanthracene bridged bis-naphthopyrans: A multimodal chromophore with mechano- and photo-chromic properties. Chinese Chemical Letters, 2024, 35(5): 108949-. doi: 10.1016/j.cclet.2023.108949
18. [18]
  Hui-Juan Wang , Wen-Wen Xing , Zhen-Hai Yu , Yong-Xue Li , Heng-Yi Zhang , Qilin Yu , Hongjie Zhu , Yao-Yao Wang , Yu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183
19. [19]
  Dan Luo , Jinya Tian , Jianqiao Zhou , Xiaodong Chi . Anthracene-bridged "Texas-sized" box for the simultaneous detection and uptake of tryptophan. Chinese Chemical Letters, 2024, 35(9): 109444-. doi: 10.1016/j.cclet.2023.109444
20. [20]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(739)
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