Citation: Liu Weijie, Li Jiao, He Kai, Huang Fangfang, Ma Yi, Li Yuxin, Li Qingshan, Xu Fengbo. Synthesis, bioactivity, action mode and 3D-QSAR of novel anthranilic diamide derivatives[J]. Chinese Chemical Letters, ;2019, 30(2): 417-420. doi: 10.1016/j.cclet.2018.05.023 shu

Synthesis, bioactivity, action mode and 3D-QSAR of novel anthranilic diamide derivatives

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

qli@nankai.edu.cn

xufb@nankai.edu.cn

Received Date: 16 April 2018
Revised Date: 9 May 2018
Accepted Date: 11 May 2018
Available Online: 21 February 2018

Figures(4)

To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized. Bioassays indicated that all of the title compounds displayed 100% mortality against diamondback moth and oriental armyworm at 100 mg/L, among which 12v and 12w showed 100% insecticidal acitvity at 5 mg/L. Surprisingly compound 12w exhibited better insecticidal acitvity than commercialized chlorantraniliprole against Pyrausta nubilalis (0.1 mg/L) and Cnaphalocrocis Medinalis (2 mg/L). 3D-QSAR and SARs statistical analysis revealed that title compounds with R² fixed as methoxy had the highest probability possessing high activity. The calcium fluorescence measurements on neurons revealed that E series compounds containing pyrazinyl may have a molecular target different from caffeine on ryanodine receptors rather than the voltage-gated calcium channel present on cytomembran.
- Anthranilic diamide,
- Ryanodine receptor,
- Insecticide,
- Action mode,
- 3D-QSAR
1. [1]
  Q. Feng, Z.L. Liu, L.X. Xiong, et al., J. Agric. Food Chem. 58(2010) 12327-12336. doi: 10.1021/jf102842r
2. [2]
  S. Treves, H. Jungbluth, F. Muntoni, F. Zorzato, Curr. Opin. Pharmacol. 8(2008) 319-326. doi: 10.1016/j.coph.2008.01.005
3. [3]
  C.W. Taylor, D.L. Prole, T. Rahman, Biochemistry 48(2009) 12062-12080. doi: 10.1021/bi901739t
4. [4]
  D.B. Sattelle, D. Cordova, T.R. Cheek, Invert. Neurosci. 8(2008) 107-119. doi: 10.1007/s10158-008-0076-4
5. [5]
  G.P. Lahm, D. Cordova, J.D. Barry, Bioorg. Med. Chem. 17(2009) 4127-4133. doi: 10.1016/j.bmc.2009.01.018
6. [6]
  H. Wang, M.I. Na, Z.J. Fan, N.P. Belskaia, V.A. Bakulev, J. Sichuan Normal Univ. 34(2011) 427-434.
7. [7]
  M. Porta, A.V. Zima, A. Nani, et al., Biophysics 100(2011) 931-938.
8. [8]
  M. Tohnishi, H. Nakao, T. Furuya, et al., J. Pestic. Sci. 30(2005) 354-360. doi: 10.1584/jpestics.30.354
9. [9]
  L.G. Philip, T.M. Stevenson, B.J. Myers, T.P. Selby, Patent, US 20000191242, 2003.
10. [10]
  T.M. Stevenson, G.P. Lahm, R.J. Pasteris, Patent, WO 03106427(A2), 2003.
11. [11]
  G.P. Lahm, T.P. Selby, Patent, WO 0248137(A2), 2003.
12. [12]
  M.M. Wang, Q.Q. Zhang, K. Yue, Q.S. Li, F.B. Xu, Chin. J. Org. Chem. 37(2017) 1774-1780. doi: 10.6023/cjoc201612030
13. [13]
  M. Ibrahim, K. Andries, N. Lounis, et al., Agents Chem. 51(2007) 1011-1015. doi: 10.1128/AAC.00898-06
14. [14]
  H. Malipeddi, V. Malipeddi, S. Mathur, et al., Int. J. Res. Ayurveda Pharm. 1(2010) 180-185.
15. [15]
  R.C. Reynolds, A. Tiwari, J.E. Harwell, et al., J. Med. Chem. 43(2000) 1484-1488. doi: 10.1021/jm990417j
16. [16]
  Q.S. Ma, X.H. Liu, J.Q. Weng, et al., Chin. J. Org. Chem. 33(2013) 1749-1754. doi: 10.6023/cjoc201301061
17. [17]
  R.D.C. Iii, S.B. Wold, Patent, US 5307287(A), 1991.
18. [18]
  Q. Chen, X.L. Zhu, L.L. Jiang, Z.M. Liu, G.F. Yang, Eur. J. Med. Chem. 39(2010) 595-603.
19. [19]
  U. Ebbinghaus-Kintscher, K. Raming, T. Masaki, N. Yasokawa, PflanzenschutzNachrichten Bayer 60(2007) 117-140.
20. [20]
  T. Masaki, N. Yasokawa, S. Fujioka, K. Motoba, M. Tohnishi, et al., J. Pestic. Sci. 34 (2009) 37-42.
1. [1]
  Gengchen Guo , Tianyu Zhao , Ruichang Sun , Mingzhe Song , Hongyu Liu , Sen Wang , Jingwen Li , Jingbin Zeng . Au-Fe₃O₄ dumbbell-like nanoparticles based lateral flow immunoassay for colorimetric and photothermal dual-mode detection of SARS-CoV-2 spike protein. Chinese Chemical Letters, 2024, 35(6): 109198-. doi: 10.1016/j.cclet.2023.109198
2. [2]
  Siyu Zong , Xiaowei Yu , Yining Yang , Xin Yang , Jiyang Li . Multi-mode luminescence anti-counterfeiting and visual iron(Ⅲ) ions RTP detection constructed by assembly of CDs&Eu³⁺ in porous RHO zeolite. Chinese Chemical Letters, 2025, 36(6): 110343-. doi: 10.1016/j.cclet.2024.110343
3. [3]
  Hui Peng , Xiao Wang , Weiguo Huang , Shuiyue Yu , Linghang Kong , Qilin Wei , Jialong Zhao , Bingsuo Zou . Efficient tunable visible and near-infrared emission in Sb³⁺/Sm³⁺-codoped Cs₂NaLuCl₆ for near-infrared light-emitting diode, triple-mode fluorescence anti-counterfeiting and information encryption. Chinese Chemical Letters, 2024, 35(11): 109462-. doi: 10.1016/j.cclet.2023.109462
4. [4]
  Qi Huang , Jun Liao , Jingjing Li , Zhengyan Gu , Xinkang Zhang , Mingxue Sun , Wenqi Meng , Guanchao Mao , Zhipeng Pei , Shanshan Zhang , Songling Li , Chuan Zhang , Yunqin Wang , Jihao Liu , Tingbin Shu , Min Tao , Ying Lu , Kai Xiao , Qingqiang Xu , Jincai Lu . Curcumin-loaded ceria nanoenzymes for dual-action suppression of inflammation and alleviation of oxidative damage in the treatment of acute lung injury. Chinese Chemical Letters, 2025, 36(4): 109914-. doi: 10.1016/j.cclet.2024.109914
5. [5]
  Zhibin Ren , Shan Li , Xiaoying Liu , Guanghao Lv , Lei Chen , Jingli Wang , Xingyi Li , Jiaqing Wang . Penetrating efficiency of supramolecular hydrogel eye drops: Electrostatic interaction surpasses ligand-receptor interaction. Chinese Chemical Letters, 2024, 35(11): 109629-. doi: 10.1016/j.cclet.2024.109629
6. [6]
  Meng Gao , Jiqiu Yin , XianChao Jia , Ye Gao , Yang Jiao . On-target site enriching fluorescent bioprobe for imaging of receptor tyrosine kinase in tumor. Chinese Chemical Letters, 2025, 36(6): 110297-. doi: 10.1016/j.cclet.2024.110297
7. [7]
  Kai Wang , Yun Wang , Lihang Wang , Zhuhai Li , Xi Yu , Xuanhe You , Diwei Wu , Yueming Song , Jiancheng Zeng , Zongke Zhou , Shishu Huang , Yunfeng Lin . Therapeutic siRNA targeting CC chemokine receptor 2 loaded with tetrahedral framework nucleic acid alleviates neuropathic pain by regulating microglial polarization. Chinese Chemical Letters, 2025, 36(3): 109868-. doi: 10.1016/j.cclet.2024.109868
8. [8]
  Yuexi Guo , Zhaoyang Li , Jingwei Dai . Charlie and the 3D Printing Chocolate Factory. University Chemistry, 2024, 39(9): 235-242. doi: 10.3866/PKU.DXHX202309067
9. [9]
  Shenghui Tu , Anru Liu , Hongxiang Zhang , Lu Sun , Minghui Luo , Shan Huang , Ting Huang , Honggen Peng . Oxygen vacancy regulating transition mode of MIL-125 to facilitate singlet oxygen generation for photocatalytic degradation of antibiotics. Chinese Chemical Letters, 2024, 35(12): 109761-. doi: 10.1016/j.cclet.2024.109761
10. [10]
  Tong Zhang , Xiaojing Liang , Licheng Wang , Shuai Wang , Xiaoxiao Liu , Yong Guo . An ionic liquid assisted hydrogel functionalized silica stationary phase for mixed-mode liquid chromatography. Chinese Chemical Letters, 2025, 36(1): 109889-. doi: 10.1016/j.cclet.2024.109889
11. [11]
  Hejie Zheng , Zhili Wang , Guizhen Luo , Cuicui Du , Xiaohua Zhang , Jinhua Chen . A novel PEC-EC dual-mode biosensing platform for dual target detection of miRNA-133a and cTnI. Chinese Chemical Letters, 2025, 36(4): 110131-. doi: 10.1016/j.cclet.2024.110131
12. [12]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
13. [13]
  Qiuye Wang , Yabing Sun , Liangxue Lai , Haijing Cui , Yonglong Ye , Ming Yang , Weihao Zhu , Bo Yuan , Quanliang Mao , Wenzhi Ren , Aiguo Wu . MMP-9-responsive probe for fluorescence-magnetic resonance dual-mode imaging of hepatocellular carcinoma models with different metastatic capacities. Chinese Chemical Letters, 2025, 36(4): 110212-. doi: 10.1016/j.cclet.2024.110212
14. [14]
  Jie XIE , Hongnan XU , Jianfeng LIAO , Ruoyu CHEN , Lin SUN , Zhong JIN . Nitrogen-doped 3D graphene-carbon nanotube network for efficient lithium storage. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1840-1849. doi: 10.11862/CJIC.20240216
15. [15]
  Xi Xu , Chaokai Zhu , Leiqing Cao , Zhuozhao Wu , Cao Guan . Experiential Education and 3D-Printed Alloys: Innovative Exploration and Student Development. University Chemistry, 2024, 39(2): 347-357. doi: 10.3866/PKU.DXHX202308039
16. [16]
  Qiang Zhou , Pingping Zhu , Wei Shao , Wanqun Hu , Xuan Lei , Haiyang Yang . Innovative Experimental Teaching Design for 3D Printing High-Strength Hydrogel Experiments. University Chemistry, 2024, 39(6): 264-270. doi: 10.3866/PKU.DXHX202310064
17. [17]
  Changyuan Bao , Yunpeng Jiang , Haoyin Zhong , Huaizheng Ren , Junhui Wang , Binbin Liu , Qi Zhao , Fan Jin , Yan Meng Chong , Jianguo Sun , Fei Wang , Bo Wang , Ximeng Liu , Dianlong Wang , John Wang . Synergizing 3D-printed structure and sodiophilic interface enables highly efficient sodium metal anodes. Chinese Chemical Letters, 2024, 35(11): 109353-. doi: 10.1016/j.cclet.2023.109353
18. [18]
  Chengmin Hu , Pingxuan Liu , Ziyang Song , Yaokang Lv , Hui Duan , Li Xie , Ling Miao , Mingxian Liu , Lihua Gan . Tailor-made overstable 3D carbon superstructures towards efficient zinc-ion storage. Chinese Chemical Letters, 2025, 36(4): 110381-. doi: 10.1016/j.cclet.2024.110381
19. [19]
  Run Chai , Qiujie Wu , Yongchao Liu , Xiaohui Song , Xuyong Feng , Yi Sun , Hongfa Xiang . A 3D dual layer host with enhanced sodiophilicity as stable anode for high-energy sodium metal batteries. Chinese Chemical Letters, 2025, 36(6): 110007-. doi: 10.1016/j.cclet.2024.110007
20. [20]
  Yuan Teng , Zichun Zhou , Jinghua Chen , Siying Huang , Hongyan Chen , Daibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs₃Bi₂Br₉/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(909)
HTML views(38)

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