Synthesis and Biological Activity of 1,2,4-Triazole Thioether Derivatives Containing Pyrazole Moiety

被引:31
|
作者
Zhai, Zhiwen [1 ]
Wang, Qiao [1 ]
Shen, Zhonghua [1 ]
Tan, Chengxia [1 ]
Weng, Jianquan [1 ]
Liu, Xinghai [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
关键词
pyrazole; 1,2,4-triazole; synthesis; fungicidal activity; herbicidal activity; ONE-POT SYNTHESIS; DIMERIC CRYSTAL-STRUCTURE; ANTIFUNGAL ACTIVITY; FACILE; DFT;
D O I
10.6023/cjoc201607031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel 1,2,4-triazole derivatives were synthesized from ethyl trifluoroacetoacetate, triethyl orthoformate, methylhydrazine, phenyl isothiocyanate by multi-step reactions. Their structures were characterized by H-1 NMR, C-13 NMR, HRMS and X-ray diffraction. The target compounds were evaluated for their fungicidal activity and herbicidal activitiy. The results indicated that some of the title compounds displayed certain fungicidal activities against Colletotrichum orbiculare and herbicidal activity against dicotyledons.
引用
收藏
页码:232 / 236
页数:5
相关论文
共 23 条
  • [1] Radiosynthesis and evaluation of 5-methyl-N-(4-[11C]methylpyrimidin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine ([11C]ADX88178) as a novel radioligand for imaging of metabotropic glutamate receptor subtype 4 (mGluR4)
    Fujinaga, Masayuki
    Yamasaki, Tomoteru
    Nengaki, Nobuki
    Ogawa, Masanao
    Kumata, Katsushi
    Shimoda, Yoko
    Yui, Joji
    Xie, Lin
    Zhang, Yiding
    Kawamura, Kazunori
    Zhang, Ming-Rong
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (02) : 370 - 374
  • [2] Liu C. L., 1997, WORD PESTIC, V19, P24
  • [3] Synthesis and insecticidal activity of novel pyrimidine derivatives containing urea pharmacophore against Aedes aegypti
    Liu, Xing-Hai
    Wang, Qiao
    Sun, Zhao-Hui
    Wedge, David E.
    Becnel, James J.
    Estep, Alden S.
    Tan, Cheng-Xia
    Weng, Jian-Quan
    [J]. PEST MANAGEMENT SCIENCE, 2017, 73 (05) : 953 - 959
  • [4] Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives
    Liu, Xing-Hai
    Zhao, Wen
    Shen, Zhong-Hua
    Xing, Jia-Hua
    Yuan, Jing
    Yang, Guo
    Xu, Tian-Ming
    Peng, Wei-Li
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (15) : 3626 - 3628
  • [5] Facile and efficient synthesis and herbicidal activity determination of novel 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one derivatives via microwave irradiation
    Liu, Xing-Hai
    Zhai, Zhi-Wen
    Xu, Xiao-Yan
    Yang, Ming-Yan
    Sun, Zhao-Hui
    Weng, Jian-Quan
    Tan, Cheng-Xia
    Chen, Jie
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (23) : 5524 - 5528
  • [6] Microwave Assistant One Pot Synthesis, Crystal Structure, Antifungal Activities and 3D-QSAR of Novel 1,2,4-Triazolo[4,3-a]pyridines
    Liu, Xing-Hai
    Sun, Zhao-Hui
    Yang, Ming-Yan
    Tan, Cheng-Xia
    Weng, Jian-Quan
    Zhang, Yong-Gang
    Ma, Yi
    [J]. CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 84 (03) : 342 - 347
  • [7] Microwave-assisted synthesis of novel fluorinated 1,2,4-triazole derivatives, and study of their biological activity
    Liu, Xing-Hai
    Weng, Jian-Quan
    Wang, Bao-Lei
    Li, Yong-Hong
    Tan, Cheng-Xia
    Li, Zheng-Ming
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2014, 40 (08) : 2605 - 2612
  • [8] Synthesis, structure, and biological activity of novel (oxdi/tri)azoles derivatives containing 1,2,3-thiadiazole or methyl moiety
    Liu, Xing-Hai
    Pan, Li
    Weng, Jian-Quan
    Tan, Cheng-Xia
    Li, Yong-Hong
    Wang, Bao-Lei
    Li, Zheng-Ming
    [J]. MOLECULAR DIVERSITY, 2012, 16 (02) : 251 - 260
  • [9] SYNTHESIS, DIMERIC CRYSTAL STRUCTURE, AND FUNGICIDAL ACTIVITY OF 1-(4-METHYLPHENYL)-2-(5-((3,5-DIMETHYL-1H-PYRAZOL-1-YL)METHYL)-4-PHENYL-4H-1,2,4-TRIAZOL-3-YLTHIO)ETHANONE
    Liu, Xing-Hai
    Tan, Cheng-Xia
    Weng, Jian-Quan
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (03) : 558 - 564
  • [10] PHASE TRANSFER-CATALYZED, ONE-POT SYNTHESIS OF SOME NOVEL N-PYRIMIDINYL-N′-NICOTINYL THIOUREA DERIVATIVES
    Liu, Xing-Hai
    Tan, Cheng-Xia
    Weng, Jian-Quan
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (03) : 552 - 557