Synthesis and biological activity of novel 1,3,4-oxadiazole derivatives containing a pyrazole moiety

被引:18
作者
Yu, Wei [1 ]
Zhai, Zhi-Wen [1 ]
Wedge, David E. [2 ]
Duke, Stephen O. [2 ]
Wu, Hong-Ke [1 ]
Weng, Jian-Quan [1 ]
Tan, Cheng-Xia [1 ]
Zhang, Yong-Gang [3 ]
Liu, Xing-Hai [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
[2] USDA ARS, Nat Prod Utilizat Res Unit, University, MS 38677 USA
[3] Qilu Univ Technol, Biol Inst, Shandong Acad Sci, Jinan, Shandong, Peoples R China
关键词
Oxadiazole; Pyrazole; Synthesis; Fungicide; Herbicide; CRYSTAL-STRUCTURE; NEMATOCIDAL ACTIVITY; ANTIFUNGAL ACTIVITY; FUNGICIDAL ACTIVITY; 1,2,3-THIADIAZOLE DERIVATIVES; ANTIMICROBIAL ACTIVITY; HERBICIDAL ACTIVITY; EFFICIENT SYNTHESIS; ONE-POT; HYDRAZONE;
D O I
10.1007/s11164-019-04015-8
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several new 1,3,4-oxadiazole derivatives containing a pyrazole ring were designed and synthesized from ethyl acetoacetate and triethyl orthoformate as starting materials via multi-step reactions. The compound structures were confirmed by melting point, H-1 NMR and HRMS. They were evaluated for fungicidal and herbicidal activities. Four of the compounds exhibited moderate fungicidal activity against Colletotrichum species. Most of the compounds had moderate-to-good activity as a herbicide.
引用
收藏
页码:5989 / 6001
页数:13
相关论文
共 64 条
[1]   Synthesis and chemical transformations of 3-acetyl-4-hydroxyquinolin-2(1H)-one and its N-substituted derivatives: bird's eye view [J].
Abdou, Moaz M. ;
Seferoglu, Zeynel ;
Fathy, Mahmoud ;
Akitsu, Takashiro ;
Koketsu, Mamoru ;
Kellow, Ruba ;
Amigues, Eric .
RESEARCH ON CHEMICAL INTERMEDIATES, 2019, 45 (03) :919-934
[2]   -CD-catalyzed multicomponent domino reaction: synthesis, characterization, in silico molecular docking and biological evaluation of pyrano[2,3-d]-pyrimidinone derivatives [J].
Chate, Asha V. ;
Dongre, Ravindra M. ;
Khaire, Mahadeo K. ;
Bondle, Giribala M. ;
Sangshetti, Jaiprakash N. ;
Damale, Manoj .
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (10) :6119-6136
[3]   Synthesis and biological evaluation of hydrazone and pyrazoline derivatives derived from androstenedione [J].
Chen, Shaorui ;
Wu, Hao ;
Li, Ai-jun ;
Pei, Juan ;
Zhao, Lianmei .
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (11) :7029-7046
[4]  
Chen SH, 2016, NAT PROD COMMUN, V11, P931
[5]   Synthesis, Nematicidal Activity and Docking Study of Novel Pyrazole-4-carboxamide Derivatives Against Meloidogyne incognita [J].
Cheng, Long ;
Zhao, Wen ;
Shen, Zhong-Hua ;
Xu, Tian-Ming ;
Wu, Hong-Ke ;
Peng, Wei-Li ;
Liu, Xing-Hai .
LETTERS IN DRUG DESIGN & DISCOVERY, 2019, 16 (01) :29-35
[6]   Synthesis and Nematocidal Activity of N-Substituted 3-Methyl-1H-pyrazole-4-carboxamide Derivatives Against Meloidogyne incognita [J].
Cheng, Long ;
Shen, Zhong-Hua ;
Xu, Tian-Ming ;
Tan, Cheng-Xia ;
Weng, Jian-Quan ;
Han, Liang ;
Peng, Wei-Li ;
Liu, Xing-Hai .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (04) :946-950
[7]   Investigating the mode of action of natural phytotoxins [J].
Dayan, FE ;
Romagni, JG ;
Duke, SO .
JOURNAL OF CHEMICAL ECOLOGY, 2000, 26 (09) :2079-2094
[8]   Design, synthesis, biological activity and density function theory study of pyrazole derivatives containing 1,3,4-thiadiazole moiety [J].
Ding, Xiaoming ;
Zhai, Zhiwen ;
Lv, Luping ;
Sun, Zhaohui ;
Liu, Xinghai .
FRONTIERS OF CHEMICAL SCIENCE AND ENGINEERING, 2017, 11 (03) :379-386
[9]   Synthesis and in vitro antiproliferative activity of new 1,3,4-oxadiazole derivatives possessing sulfonamide moiety [J].
El-Din, Mahmoud M. Gamal ;
El-Gamal, Mohammed I. ;
Abdel-Maksoud, Mohammed S. ;
Yoo, Kyung Ho ;
Oh, Chang-Hyun .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 :45-52
[10]   Design, synthesis, antiviral activity and three-dimensional quantitative structure-activity relationship study of novel 1,4-pentadien-3-one derivatives containing the 1,3,4-oxadiazole moiety [J].
Gan, Xiuhai ;
Hu, Deyu ;
Li, Pei ;
Wu, Jian ;
Chen, Xuewen ;
Xue, Wei ;
Song, Baoan .
PEST MANAGEMENT SCIENCE, 2016, 72 (03) :534-543