Synthesis and Insecticidal Evaluation of Novel Phthalic Diamides Containing 1,2,3-Triazoles via Click Reaction

被引：12

作者：

Chen, Yinbo ^{[1
]}

Xiao, Youxin ^{[1
]}

Shao, Xusheng ^{[1
]}

Xu, Xiaoyong ^{[1
]}

Li, Zhong ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2014年 / 32卷 / 07期

基金：

中国国家自然科学基金; 国家高技术研究发展计划(863计划);

关键词：

phthalic diamide; 1,2,3-triazole; click chemistry; synthesis; bioactivity; ONE-POT SYNTHESIS; CHEMISTRY; AZIDE; ACID; DERIVATIVES; HALIDES;

D O I：

10.1002/cjoc.201400202

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of novel phthalic diamide derivatives containing 1,2,3-triazole moiety were synthesized using one-pot click chemistry approach and characterized by H-1 NMR and HRMS. The insecticidal activity against armyworm (Mythimna separata), Tetranychus cinnabarinus and cowpea aphid (Aphis craccivora) was evaluated. Compounds 4II-a and 4II-i showed 50% insecticidal activity against armyworm (Mythimna separata) at the concentration of 4 mg/L and one-third of the compounds had moderate activity against Tetranychus cinnabarinus at 500 mg/L.

引用

页码：592 / 598

页数：7

共 27 条

[1] Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].

Agalave, Sandip G. ;

Maujan, Suleman R. ;

Pore, Vandana S. .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718

[2] Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues [J].

Aher, Nilkanth G. ;

Pore, Vandana S. ;

Mishra, Nripendra N. ;

Kumar, Awanit ;

Shukla, Praveen K. ;

Sharma, Aanchal ;

Bhat, Manoj K. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (03) :759-763

[3] Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].

Barral, Karine ;

Moorhouse, Adam D. ;

Moses, John E. .

ORGANIC LETTERS, 2007, 9 (09) :1809-1811

[4] 1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics [J].

Bock, Victoria D. ;

Speijer, Dave ;

Hiemstra, Henk ;

van Maarseveen, Jan H. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (06) :971-975

[5] Heterocycles in organic synthesis: thiazoles and triazoles as exemplar cases of synthetic auxiliaries [J].

Dondoni, Alessandro .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (15) :3366-3385

[6] 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

[7] 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

[8] Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis [J].

Genin, MJ ;

Allwine, DA ;

Anderson, DJ ;

Barbachyn, MR ;

Emmert, DE ;

Garmon, SA ;

Graber, DR ;

Grega, KC ;

Hester, JB ;

Hutchinson, DK ;

Morris, J ;

Reischer, RJ ;

Ford, CW ;

Zurenko, GE ;

Hamel, JC ;

Schaadt, RD ;

Stapert, D ;

Yagi, BH .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :953-970

[9] A Copper(I)-Catalyzed 1,2,3-Triazole Azide-Alkyne Click Compound Is a Potent Inhibitor of a Multidrug-Resistant HIV-1 Protease Variant [J].

Giffin, Michael J. ;

Heaslet, Holly ;

Brik, Ashraf ;

Lin, Ying-Chuan ;

Cauvi, Gabrielle ;

Wong, Chi-Huey ;

McRee, Duncan E. ;

Elder, John H. ;

Stout, C. David ;

Torbett, Bruce E. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (20) :6263-6270

[10] 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

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