Citation: Yin-Bo Chen, Ji-Ling Li, Xu-Sheng Shao, Xiao-Yong Xu, Zhong Li. Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold[J]. Chinese Chemical Letters, ;2013, 24(8): 673-676. shu

Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold

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

Corresponding author: Zhong Li,
Received Date: 5 March 2013
Available Online: 18 April 2013

A series of novel anthranilic diamides with benzyl sulfide scaffold were synthesized, in which N-pyridylpyrazole moiety generally regarded as key pharmacophore was abandoned. The target compounds were characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. The preliminary bioassays indicated that half of the title compounds were endowed with good insecticidal activities against armyworm (Mythimna sepatara) at the concentration of 500 mg/L. Exhilaratingly, the synthesized compound 3a was also active against Tetranychus cinnabarinus at 100 mg/L. The difference in activities between the target compounds was influenced by the substituents, which provided some hints for further investigation on structure modifications.
- Anthranilic diamides,
- Benzyl sulfide,
- Synthesis,
- Insecticidal activity
1. [1]
  [1] T. Unruh, L. Willett, Survey for resistence to four insecticides in Myzus Persicae clones from peach trees and weeds in south-central Washington, J. Econ. Entomol. 101 (2008) 1919-1926.
2. [2]
  [2] G.P. Lahm, T.M. Stevenson, T.P. Selby, et al., Rynaxypyr: a new insecticidal anthranilic diamide that acts as a potent and selective ryanodine receptor activator, Bioorg. Med. Chem. Lett. 17 (2007) 6274-6279.
3. [3]
  [3] M. Tohnishi, H. Nakao, T. Furuya, et al., Flubendiamide, a new insecticide characterized by its novel chemistry and biology, J. Pestic. Sci. 30 (2005) 354-360.
4. [4]
  [4] D.B. Sattelle, D. Cordova, T.R. Cheek, Insect ryanodine receptors: molecular targets for novel pest control chemicals, Invert. Neurosci. 8 (2008) 107-119.
5. [5]
  [5] B. Alig, R. Fischer, C. Funke, et al., Anthranilamides, WO 2006000336 A2, 2006.
6. [6]
  [6] B. Alig, R. Fischer, C. Funke, et al., Anthranilic acid diamide derivative with heteroaromatic and hetero-cyclic substituents, WO 2007144100 A1, 2007.
7. [7]
  [7] G.P. Lahm, Novel anthranilamides useful for controlling invertebrate pests, WO 2006023783, 2006.
8. [8]
  [8] Q. Feng, Z.L. Liu, L.X. Xiong, et al., Synthesis and insecticidal activities of novel anthranilic diamides containing modified N-pyridylpyrazoles, J. Agric. Food Chem. 58 (2010) 12327-12336.
9. [9]
  [9] K.A. Hughes, G.P. Lahm, T.P. Selby, et al., Cyano anthranilamide insecticides, WO 2004067528 A1, 2004.
10. [10]
  [10] O. Loiseleur, R.G. Hall, A.D. Stoller, et al., Novel insecticides, WO 2009024341 A2, 2009.
11. [11]
  [11] O. Loiseleur, P. Durieux, S. Trah, et al., Pesticides containing a bicyclic bisamide structure, WO 2007093402 A1, 2007.
12. [12]
  [12] N. Monir, D. Pedroni, R. Senn, A method of reducing insect-vectored viral infections, WO 2011134876 A1, 2011.
13. [13]
  [13] W.L. Dong, J.Y. Xu, L.X. Xiong, et al., Synthesis, structure and insecticidal activities of some novel amides containing N-pyridylpyrazole moeities, Molecules 17 (2012) 10414-10428.
14. [14]
  [14] G.P. Lahm, T.P. Selby, T.M. Stevenson, Anthranilamide insecticides, WO 2004033468 A1, 2004.
15. [15]
  [15] A. Jeanguenat, A.C. O'sullivan, Anthranilamide derivatives as insecticides, WO 2006061200 A1, 2006.
16. [16]
  [16] B. Kruger, A. Hense, B. Alig, et al., Dioxazine-and oxadiazine-substituted arylamides, WO 2007031213 A1, 2007.
17. [17]
  [17] M. Muehlebach, G.W. Craig, N-Cyanoalkylanthranilamides as insecticides, WO 2008064891 A1, 2008.
18. [18]
  [18] W.L. Dong, J.Y. Xu, X.H. Liu, et al., Synthesis, crystal structure and biological activity of novel anthranilic diamides containing 1,2,3-thiadiazole, Chem. J. Chin. Univ. 29 (2008) 1990-1994.
19. [19]
  [19] W.L. Dong, X.H. Liu, J.Y. Xu, et al., Design and synthesis of novel anthranilic diamides containing 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine, J. Chem. Res. (2008) 530-533.
20. [20]
  [20] L. Clemens, Surfur chemistry in crop protection, J. Sulfur. Chem. 25 (2004) 39-62.
21. [21]
  [21] S. Kagabu, Discovery of imidacloprid and further developments from strategic molecular designs, J. Agric. Food Chem. 59 (2011) 2887-2896.
22. [22]
  [22] Y. Zhu, M.R. Loso, G.B. Watson, et al., Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests, J. Agric. Food Chem. 59 (2011) 2950-2957.
23. [23]
  [23] L. Chen, Q.M. Wang, R.Q. Huang, et al., Synthesis and insecticidal evaluation of propesticides of benzoylphenylureas, J. Agric. Food Chem. 53 (2005) 38-41.
24. [24]
  [24] Y.P. Luo, G.F. Yang, Discovery of a new insecticide lead by optimizing a targetdiverse scaffold: tetrazolinone derivatives, Bioorg. Med. Chem. 15 (2007) 1716-1724.
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]
  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
4. [4]
  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
5. [5]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
6. [6]
  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
7. [7]
  Yuetong Gao , Tong Mu , Xinyue Hu , Yang Pang , Chengji Zhao . Facile synthesis of all-carbon fluorinated backbone polymers containing sulfide linkage as proton exchange membranes for fuel cells. Chinese Chemical Letters, 2025, 36(6): 110763-. doi: 10.1016/j.cclet.2024.110763
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]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
15. [15]
  Hang Wang , Qi Wang , Chuan-De Wu . Continuous synthesis of ammonia. Chinese Journal of Structural Chemistry, 2025, 44(3): 100437-100437. doi: 10.1016/j.cjsc.2024.100437
16. [16]
  Zhaojun Liu , Zerui Mu , Chuanbo Gao . Alloy nanocrystals: Synthesis paradigms and implications. Chinese Journal of Structural Chemistry, 2023, 42(11): 100156-100156. doi: 10.1016/j.cjsc.2023.100156
17. [17]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
18. [18]
  Hui Jin , Qin Cai , Peiwen Liu , Yan Chen , Derong Wang , Weiping Zhu , Yufang Xu , Xuhong Qian . Multistep continuous flow synthesis of Erlotinib. Chinese Chemical Letters, 2024, 35(4): 108721-. doi: 10.1016/j.cclet.2023.108721
19. [19]
  Xingjie Li , Chengjun Yi , Weifei Hu , Huishan Zhang , Jiale Xia , Yuanyuan Li , Jinping Liu . Emerging sulfide-polymer composite solid electrolyte membranes. Chinese Chemical Letters, 2025, 36(6): 110215-. doi: 10.1016/j.cclet.2024.110215
20. [20]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(997)
HTML views(39)

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