Design, synthesis and insecticidal activity of biphenyl-diamide derivatives

被引:13
作者
Liu, Ye [1 ]
Lei, Chao [1 ]
Xu, Xiao-Yong [1 ]
Shao, Xu-Sheng [1 ]
Li, Zhong [1 ]
机构
[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China
关键词
Diamide; Insecticide; Ryanodine insecticide; Biphenyl; ACID; FLUBENDIAMIDE; MODE;
D O I
10.1016/j.cclet.2015.12.011
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Diamides acting on insect ryanodine receptors are an intensive research area now. In order to search for novel candidates, a series of diamides containing biphenyl substructure were designed and synthesized. Their insecticidal activities against armyworms (Mythimna sepatara) and aphis (Aphis craccivora) were screened. The compounds with 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl substituent were found to be insecticidal to armyworms with the similar symptoms to poisoning by flubendiamide. In this research, we presented a novel type of diamide insecticide as a lead compound for further optimization. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:321 / 324
页数:4
相关论文
共 27 条
[1]   Anthranilic diamides: A new class of insecticides with a novel mode of action, ryanodine receptor activation [J].
Cordova, D ;
Benner, EA ;
Sacher, MD ;
Rauh, JJ ;
Sopa, JS ;
Lahm, GP ;
Selby, TP ;
Stevenson, TM ;
Flexner, L ;
Gutteridge, S ;
Rhoades, DF ;
Wu, L ;
Smith, RM ;
Tao, Y .
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2006, 84 (03) :196-214
[2]  
Dubost C., 2013, Patent No. [WO 2013167550, 2013167550]
[3]   Phthalic acid diamides activate ryanodine-sensitive Ca2+ release channels in insects [J].
Ebbinghaus-Kintscher, U ;
Luemmen, P ;
Lobitz, N ;
Schulte, T ;
Funke, C ;
Fischer, R ;
Masaki, T ;
Yasokawa, N ;
Tohnishi, M .
CELL CALCIUM, 2006, 39 (01) :21-33
[4]   Synthesis, Insecticidal Activity, and Structure-Activity Relationship of Trifluoromethyl-Containing Phthalic Acid Diamide Structures [J].
Feng, Mei-Li ;
Li, Yu-Feng ;
Zhu, Hong-Jun ;
Zha, Liang ;
Xi, Bin-Bin ;
Ni, Jue-Ping .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (20) :10999-11006
[5]   Novel diamide insecticides: Sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives [J].
Gnamm, Christian ;
Jeanguenat, Andre ;
Dutton, Ana C. ;
Grimm, Christoph ;
Kloer, Daniel P. ;
Crossthwaite, Andrew J. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (11) :3800-3806
[6]  
Hueter O. F., 2014, Patent No. [WO 2014067838, 2014067838]
[7]   RYANODYL 3-(PYRIDINE-3-CARBOXYLATE) - A NOVEL RYANOID FROM RYANIA INSECTICIDE [J].
JEFFERIES, PR ;
TOIA, RF ;
CASIDA, JE .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04) :1147-1149
[8]  
Jung PJ. M., 2007, Patent No. [WO 2007128410, 2007128410]
[9]   Diphenic acid as a general conformational lock in the design of bihelical structures [J].
Karle, Isabella L. ;
Venkateshwarlu, Punna ;
Nagaraj, Ramakrishnan ;
Sarma, Akella V. S. ;
Vijay, Dolly ;
Sastry, Narahari G. ;
Ranganathan, Subramania .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (15) :4253-4263
[10]   Rynaxypyr™:: A new insecticidal anthranilic diamide that acts as a potent and selective ryanodine receptor activator [J].
Lahm, George P. ;
Stevenson, Thomas M. ;
Selby, Thomas P. ;
Freudenberger, John H. ;
Cordova, Daniel ;
Flexner, Lindsey ;
Bellin, Cheryl A. ;
Dubas, Christine M. ;
Smith, Ben K. ;
Hughes, Kenneth A. ;
Hollingshaus, J. Gary ;
Clark, Christopher E. ;
Benner, Eric A. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (22) :6274-6279