Design, Synthesis and Fungicidal Activities of Novel 1,2,3-Triazole Functionalized Strobilurins

被引：10

作者：

Li, Yuanxiang ^{[1
,2
]}

Lei, Sufang ^{[1
]}

Liu, Yilin ^{[1
,2
]}

机构：

[1] Huaihua Univ, Coll Chem & Mat Engn, Huaihua 418008, Peoples R China

[2] Huaihua Univ, Inst Organ Synth, Huaihua 418008, Peoples R China

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 03期

关键词：

Fungicidal activities; Strobilurin; Synthesis; 1,2,3-Triazoles; REGIOSELECTIVE SYNTHESIS; CATALYZED ARYLATION; BIOLOGICAL-ACTIVITY; DERIVATIVES; INHIBITORS; DISCOVERY;

D O I：

10.1002/slct.201803597

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of new strobilurin derivatives bearing different 1,2,3-triazole side chains were designed and synthesized. The target compounds were characterized by HRMS, H-1 NMR, C-13 NMR spectra. Among them, the structure of compound 5q was confirmed by X-ray single crystal diffraction. All of the target compounds were evaluated in vitro for their fungicidal activity against Gibberella zeae, Phytophythora capsici, Alternaria alternate, Botrytis cinerea and Sclerotonia sclerotiorum at a concentration of 25 mg/L. The bio-assay results exhibited that some of them showed moderate to good fungicidal activity against Phytophythora capsici and Alternaria alternate. The inhibition rates of compound 5f and 5g were up to 73.6% against Phytophythora capsic, which were significantly higher than 42.5% for Difenoconazole. Preliminary structure-activity relationships (SAR) were also discussed.

引用

页码：1015 / 1018

页数：4

共 41 条

[1] Synthesis and structure-activity relationships of 1-phenyl-1H-1,2,3-triazoles as selective insect GABA receptor antagonists [J].

Alam, MS ;

Kajiki, R ;

Hanatani, H ;

Kong, XY ;

Ozoe, F ;

Matsui, Y ;

Matsumura, F ;

Ozoe, Y .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (04) :1361-1372

[2] Review of strobilurin fungicide chemicals [J].

Balba, Hamdy .

JOURNAL OF ENVIRONMENTAL SCIENCE AND HEALTH PART B-PESTICIDES FOOD CONTAMINANTS AND AGRICULTURAL WASTES, 2007, 42 (04) :441-451

[3] The strobilurin fungicides [J].

Bartlett, DW ;

Clough, JM ;

Godwin, JR ;

Hall, AA ;

Hamer, M ;

Parr-Dobrzanski, B .

PEST MANAGEMENT SCIENCE, 2002, 58 (07) :649-662

[4] OUDEMANSIN, STROBILURIN-A, STROBILURIN-B AND MYXOTHIAZOL - NEW INHIBITORS OF THE BC1 SEGMENT OF THE RESPIRATORY-CHAIN WITH AN E-BETA-METHOXYACRYLATE SYSTEM AS COMMON STRUCTURAL ELEMENT [J].

BECKER, WF ;

VONJAGOW, G ;

ANKE, T ;

STEGLICH, W .

FEBS LETTERS, 1981, 132 (02) :329-333

[5] Synthesis of 1,2,3-Thiadiazole and Thiazole-Based Strobilurins as Potent Fungicide Candidates [J].

Chen, Lai ;

Zhu, Yu-Jie ;

Fan, Zhi-Jin ;

Guo, Xiao-Feng ;

Zhang, Zhi-Ming ;

Xu, Jing-Hua ;

Song, Ying-Qi ;

Yurievich, Morzherin Y. ;

Belskaya, Nataliya P. ;

Bakulev, Vasiliy A. .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2017, 65 (04) :745-751

[6] Conformational control in the regioselective synthesis of N-2-substituted-1,2,3-triazoles [J].

Chen, Yunfeng ;

Liu, Yuxiu ;

Petersen, Jeffrey L. ;

Shi, Xiaodong .

CHEMICAL COMMUNICATIONS, 2008, (28) :3254-3256

[7] Copper-Catalyzed [3+2] Cycloaddition/Oxidation Reactions between Nitro-olefins and Organic Azides: Highly Regioselective Synthesis of NO2-Substituted 1,2,3-Triazoles [J].

Chen, Yunfeng ;

Nie, Gang ;

Zhang, Qi ;

Ma, Shan ;

Li, Huan ;

Hu, Qinquan .

ORGANIC LETTERS, 2015, 17 (05) :1118-1121

[8] Direct Pd-catalyzed arylation of 1,2,3-triazoles [J].

Chuprakov, Stepan ;

Chernyak, Natalia ;

Dudnik, Alexander S. ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2007, 9 (12) :2333-2336

[9]

Clough J. M., 1992, CHEM ABSTR, V117, P90329

[10] Copper-Catalyzed Cross-Dehydrogenative N2-Coupling of NH-1,2,3-Triazoles with N,N -Dialkylamides: N-Amidoalkylation of NH-1,2,3-Triazoles [J].

Deng, Xiaocong ;

Lei, Xue ;

Nie, Gang ;

Jia, Lihui ;

Li, Yuanxiang ;

Chen, Yunfeng .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (12) :6163-6171

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