Synthesis and Biological Activities of Some Novel (E)-Alpha-(methoxyimino) benzeneacetate Derivatives with Modified 1,2,4-Triazole Moiety

被引:5
作者
Wang, Xianyou [1 ]
Wang, Hua [2 ]
Chen, Peiyun [1 ]
Pang, Yanping [1 ]
Zhao, Zhilei [1 ]
Wu, Guangchen [1 ]
机构
[1] Hebei Univ, Coll Qual & Tech Supervis, Baoding 071002, Peoples R China
[2] Hubei Acad Agr Sci, Inst Plant Protect & Soil Fertilizer, Wuhan 430064, Peoples R China
关键词
IN-VITRO ANTIFUNGAL; FUNGICIDAL ACTIVITIES; STEREOSELECTIVE-SYNTHESIS; RESISTANCE; DESIGN; CYTOTOXICITY; INHIBITORS; BASES;
D O I
10.1155/2014/681364
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
To find new strobilurin analogues with high activity against resistant pathogens, a series of (E)-alpha-(methoxyimino) benzeneacetate derivatives containing 1,2,4-triazole Schiff base side chain were designed and synthesized. Their structures were confirmed by IR, H-1 NMR, and C-13 NMR, ESI-HRMS, or elemental analyses. Bioassays indicated that most of the target compounds showed moderate to good fungicidal activities against Rhizoctonia solani, Botrytis cinerea Pers., Fusarium graminearum, Cotton rhizoctoniosis, and Blumeria graminis. For example, compounds 6g and 6j exhibited promising antifungal activity against Rhizoctonia solani, Botrytis cinerea Pers., and Fusarium graminearum. Compounds 6c, 6l, and 6m had higher fungicidal activities against Blumeria graminis at the concentration of 50 mu g/mL; inhibitory rate is 91.41%, 92.13%, and 91.77%, respectively.
引用
收藏
页数:9
相关论文
共 29 条
[1]   Design and synthesis of new 4-pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolin-1-ylthiazoles as potential antimicrobial agents [J].
Abdel-Wahab, Bakr F. ;
Abdel-Latif, Ehab ;
Mohamed, Hanan A. ;
Awad, Ghada E. A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 52 :263-268
[2]   Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles [J].
Almasirad, A ;
Tabatabai, SA ;
Faizi, M ;
Kebriaeezadeh, A ;
Mehrabi, N ;
Dalvandi, A ;
Shafiee, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (24) :6057-6059
[3]   STROBILURINS - NEW ANTIFUNGAL ANTIBIOTICS FROM BASIDIOMYCETE STROBILURUS-TENACELLUS (PERS EX FR) SING [J].
ANKE, T ;
OBERWINKLER, F ;
STEGLICH, W ;
SCHRAMM, G .
JOURNAL OF ANTIBIOTICS, 1977, 30 (10) :806-810
[4]   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
[5]   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
[6]   Synthesis, Crystal Structure, and Biological Activity of 4-Methyl-1,2,3-thiadiazole-Containing 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles [J].
Fan, Zhuin ;
Yang, Zhikun ;
Zhang, Haike ;
Na Mi ;
Huan Wang ;
Fei Cai ;
Xiang Zuo ;
Zheng, Qingxiang ;
Song, Haibin .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (05) :2630-2636
[7]   Re-examination of inhibitor resistance conferred by Qo-site mutations in cytochrome b using yeast as a model system [J].
Fisher, N ;
Meunier, B .
PEST MANAGEMENT SCIENCE, 2005, 61 (10) :973-978
[8]   Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides [J].
Gisi, U ;
Sierotzki, H ;
Cook, A ;
McCaffery, A .
PEST MANAGEMENT SCIENCE, 2002, 58 (09) :859-867
[9]   Design, synthesis, and fungicidal activities of new strobilurin derivatives [J].
Huang, Wei ;
Zhao, Pei-Liang ;
Liu, Chang-Ling ;
Chen, Qiong ;
Liu, Zu-Ming ;
Yang, Guang-Fu .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2007, 55 (08) :3004-3010
[10]  
Jalilian AR, 2000, ARCH PHARM, V333, P347, DOI 10.1002/1521-4184(200010)333:10<347::AID-ARDP347>3.0.CO