Citation: Nan-Yang Chen, Li-Ping Ren, Min-Ming Zou, Zhi-Ping Xu, Xu-Sheng Shao, Xiao-Yong Xu, Zhong Li. Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs[J]. Chinese Chemical Letters, ;2014, 25(2): 197-200. shu

Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs

1.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Xu-Sheng Shao, Zhong Li,
Received Date: 23 September 2013
Available Online: 25 November 2013
Fund Project: This work was financial supported by National Basic Research Program of China (973 Program, No. 2010CB126100) (973 Program, No. 2010CB126100) National High Technology Research Development Program of China (863 Program, No. 2011AA10A207) (863 Program, No. 2011AA10A207) Key Projects in the National Science & Technology Pillar Program (No. 2011BAE06B05) (No. 2011BAE06B05) National Natural Science Foundation of China (No. 21372079) (No. 21372079) Shanghai Education Committee (No. 12ZZ057) (No. 12ZZ057)

Spiro heterocycles frequently occur in bioactive molecules. In the pursuit of neonicotinoids with spiro heterocycles, three types of novel neonicotinoids with spirobenzofuranone, spirooxindole or spiroacenaphythylenone framework were designed and synthesized. Insecticidal evaluation showed that some of spirobenzofuranone containing neonicotinoids exhibited moderate activity against cowpea aphid, armyworm or brown planthopper.
- Neonicotinoid,
- Spiro heterocycle,
- Activity,
- Insecticide
1. [1]
  [1] R. Rios, Enantioselective methodologies for the synthesis of spiro compounds, Chem. Soc. Rev. 41 (2012) 1060-1074.
2. [2]
  [2] T. Jin, M. Himuro, Y. Yamamoto, Triflic acid catalyzed synthesis of spirocycles via acetylene cations, Angew. Chem. Int. Ed. 48 (2009) 5893-5896.
3. [3]
  [3] G.S. Singh, Z.Y. Desta, Isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks, Chem. Rev. 112 (2012) 6104-6155.
4. [4]
  [4] H. Diirr, R. Gleiter, Spiroconjugation, Angew. Chem. Int. Ed. 17 (1978) 559-569.
5. [5]
  [5] B. Gleiter, H. Hoffmann, H. Irngartinger, M. Nixdorf, Donor-acceptor spiro-compounds- syntheses, structures and electronic properties, Chem. Ber. 127 (1994) 2215-2224.
6. [6]
  [6] J. Sun, Y.J. Xie, C.G. Yan, Construction of dispirocyclopentanebisoxindoles via selfdomino michael-aldol reactions of 3-phenacylideneoxindoles, J. Org. Chem. 78 (2013) 8354-8365.
7. [7]
  [7] K. Murai, H. Komatsu, R. Nagao, H. Fujioka, Oxidative rearrangement of spiro cyclobutane cyclic aminals: efficient construction of bicyclic amidines, Org. Lett. 14 (2012) 772-775.
8. [8]
  [8] W.Y. Xu, Y.M. Jia, J.K. Yang, Z.T. Huang, C.Y. Yu, Reactions of heterocyclic detene aminals with 2-[3-oxoisobenzofuran-1(3H)-ylidenne]malononitrile: synthesis of novel polyfunctionalized 1,4-dihydropyridine-fused 1,3-diazaheterocycles, Synlett 11 (2010) 1682-1684.
9. [9]
  [9] F. Shi, G.J. Xing, R.Y. Zhu, W. Tan, S.J. Tu, A catalytic asymmetric isatin-involved povarov reaction: diastereo- and enantioselective construction of spiro[indolin- 3,2'-quinoline] scaffold, Org. Lett. 15 (2013) 1128-1131.
10. [10]
  [10] S. Pal, M.N. Khan, S. Karamthulla, S.J. Abbas, L.H. Choudhury, One pot fourcomponent reaction for the efficient synthesis of spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-3'-carboxylate derivatives, Tetrahedron Lett. 54 (2013) 5434-5440.
11. [11]
  [11] F.Y. Miyake, K. Yakushijin, D.A. Horne, Preparation and synthetic applications of 2-halotryptamines: synthesis of elacomine and isoelacomine, Org. Lett. 6 (2004) 711-713.
12. [12]
  [12] B. Tan, N.R. Candeias, C.F. Barbas Ⅲ, Construction of bispirooxindoles containing three quaternary stereocentres in a cascade using a single multifunctional organocatalyst, Nat. Chem. 3 (2011) 473-477.
13. [13]
  [13] S. Rapposelli, M.C. Breschi, V. Calderone, et al.,A. Balsamo, Synthesis and biological evaluation of 5-membered spiro heterocycle-benzopyran derivatives against myocardial ischemia, Eur. J. Med. Chem. 46 (2011) 966-973.
14. [14]
  [14] C.W. Lee, R. Lira, J. Dutra, K. Ogilvie, et al., Stereoselective synthesis of spiropiperidines as BACE-1 aspartyl protease inhibitors via late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore, J. Org. Chem. 78 (2013) 2661-2669.
15. [15]
  [15] M. Rottmann, C. McNamara, B.K.S. Yeung, et al., Spiroindolones, a potent compound class for the treatment of malaria, Science 329 (2010) 1175-1180.
16. [16]
  [16] A. Elbert, M. Schindler, R. Nauen, P. Jeschke, Overview of the status and global strategy for neonicotinoids, J. Agric. Food Chem. 59 (2011) 2897-2908.
17. [17]
  [17] S. Kagabu, Discovery of imidacloprid and further developments from strategic molecular designs, J. Agric. Food Chem. 59 (2011) 2887-2896.
18. [18]
  [18] M. Tomizawa, J.E. Casida, Molecular recognition of neonicotinoid insecticides: the determinants of life or death, Acc. Chem. Res. 42 (2009) 260-269.
19. [19]
  [19] R. Nauen, I. Denholm, Resistance of insect pests to neonicotinoid insecticides: current status and future prospects, Arch. Insect. Biochem. Physiol. 58 (2005) 200-215.
20. [20]
  [20] M. Henry, M. Bé guin, F. Requier, et al., A common pesticide decreases foraging success and survival in honey bees, Science 336 (2012) 348-350.
21. [21]
  [21] S.A. Cameron, J.D. Lozier, J.P. Strange, et al., Patterns of widespread decline in North American bumble bees, Proc. Natl. Acad. Sci. U.S.A. 108 (2011) 662-667.
22. [22]
  [22] X.S. Shao, P.W. Lee, Z.W. Liu, et al., cis-Configuration: a new tactic/rationale for neonicotinoid molecular design, J. Agric. Food Chem. 59 (2011) 2943-2949.
23. [23]
  [23] X.S. Shao, Z. Li, X.H. Qian, X.Y. Xu, Design, synthesis and insecticidal activities of novel analogues of neonicotinoids: replacement of nitromethylene with nitroconjugated system, J. Agric. Food Chem. 57 (2009) 951-957.
24. [24]
  [24] X.S.Shao,H.Fu, X.Y.Xu, etal.,Divalentandoxabridgedneonicotinoidsconstructedby dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities, J. Agric. Food Chem. 58 (2010) 2696-2702.
25. [25]
  [25] W.W. Zhang, X.B. Yang, W.D. Chen, et al., Design, multicomponet synthesis, and bioactivities of novel neonicotinoid analogues with 1,4-dihydropyridine scaffold, J. Agric. Food Chem. 58 (2010) 2741-2745.
26. [26]
  [26] A. Alizadeh, T. Firuzyar, A. Mikaeili, Efficient one-pot synthesis of spirooxindole derivatives containing 1,4-dihydropyridine-fused-1,3-diazaheterocycle fragments via four-component reaction, Synthesis 22 (2010) 3913-3917.
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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  Xinyu Tian , Jiaxiang Guo , Zeyi Li , Shihou Sheng , Tianyu Zhang , Xianfei Li , Chuandong Dou . Control over electronic structures of organic diradicaloids via precise B/O-heterocycle fusion. Chinese Chemical Letters, 2025, 36(1): 110174-. doi: 10.1016/j.cclet.2024.110174
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
16. [16]
  Simin Wei , Yaqing Yang , Junjie Li , Jialin Wang , Jinlu Tang , Ningning Wang , Zhaohui Li . The Mn/Yb/Er triple-doped CeO₂ nanozyme with enhanced oxidase-like activity for highly sensitive ratiometric detection of nitrite. Chinese Chemical Letters, 2024, 35(6): 109114-. doi: 10.1016/j.cclet.2023.109114
17. [17]
  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
18. [18]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
19. [19]
  Qi Tan , Run-Zhu Fan , Wencong Yang , Ge Zou , Tao Chen , Jianying Wu , Bo Wang , Sheng Yin , Zhigang She . (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Chinese Chemical Letters, 2024, 35(9): 109390-. doi: 10.1016/j.cclet.2023.109390
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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(771)
HTML views(29)

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