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
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2019年 / 45卷 / 12期
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.
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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
    Abdou, Moaz M.
    Seferoglu, Zeynel
    Fathy, Mahmoud
    Akitsu, Takashiro
    Koketsu, Mamoru
    Kellow, Ruba
    Amigues, Eric
    [J]. 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
    Chate, Asha V.
    Dongre, Ravindra M.
    Khaire, Mahadeo K.
    Bondle, Giribala M.
    Sangshetti, Jaiprakash N.
    Damale, Manoj
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (10) : 6119 - 6136
  • [3] Synthesis and biological evaluation of hydrazone and pyrazoline derivatives derived from androstenedione
    Chen, Shaorui
    Wu, Hao
    Li, Ai-jun
    Pei, Juan
    Zhao, Lianmei
    [J]. 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
    Cheng, Long
    Zhao, Wen
    Shen, Zhong-Hua
    Xu, Tian-Ming
    Wu, Hong-Ke
    Peng, Wei-Li
    Liu, Xing-Hai
    [J]. 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
    Cheng, Long
    Shen, Zhong-Hua
    Xu, Tian-Ming
    Tan, Cheng-Xia
    Weng, Jian-Quan
    Han, Liang
    Peng, Wei-Li
    Liu, Xing-Hai
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (04) : 946 - 950
  • [7] Investigating the mode of action of natural phytotoxins
    Dayan, FE
    Romagni, JG
    Duke, SO
    [J]. 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
    Ding, Xiaoming
    Zhai, Zhiwen
    Lv, Luping
    Sun, Zhaohui
    Liu, Xinghai
    [J]. 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
    El-Din, Mahmoud M. Gamal
    El-Gamal, Mohammed I.
    Abdel-Maksoud, Mohammed S.
    Yoo, Kyung Ho
    Oh, Chang-Hyun
    [J]. 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
    Gan, Xiuhai
    Hu, Deyu
    Li, Pei
    Wu, Jian
    Chen, Xuewen
    Xue, Wei
    Song, Baoan
    [J]. PEST MANAGEMENT SCIENCE, 2016, 72 (03) : 534 - 543
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