Synthesis and fungicidal activity of 1,3,4-oxadiazol-2-yl thioether derivatives containing a phenazine-1-carboxylic acid scaffold

被引:13
|
作者
Lu Xingliang [1 ]
Zhu Xiang [1 ,2 ]
Zhang Min [1 ,2 ]
Wu Qinglai [1 ,2 ]
Zhou Xudong [3 ]
Li Junkai [1 ,2 ]
机构
[1] Yangtze Univ, Sch Agr, Jingzhou, Peoples R China
[2] Yangtze Univ, Inst Pesticides, Jingzhou, Peoples R China
[3] Wenzhou Med Univ, Sch Pharmaceut Sci, Wenzhou, Peoples R China
关键词
Phenazine-1-carboxylic acid (PCA); 1,3,4-oxadiazol-2-yl thioether; fungicidal activity; derivatives; synthesis; BIOACTIVITIES;
D O I
10.1080/14786419.2018.1489389
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
To find new higher fungicidal activities lead compounds and develop new eco-friendly agrochemicals, natural product phenazine-1-carboxylic acid (PCA) as scaffold, a series of 1,3,4-oxadiazol-2-yl thioether derivatives was synthesized and bio-assayed. The results reveal that most target compounds possessed moderate to good fungicidal activities against R. solani, S. sclerotioru and P. oryzac Cavgra. Compounds 6n and 6o exhibit more than 90% bioactivity against S. sclerotioru. The EC50 value of compounds 6n and 6o are 11.16 and 30.47 mu M respectively, in particular, compound 6n show equal activity against S. sclerotioru to PCA (10.49 mu M). This result provides a valuable lead compound for further studies. [GRAPHICS] .
引用
收藏
页码:2145 / 2150
页数:6
相关论文
共 50 条
  • [1] Synthesis and fungicidal activity of phenazine-1-carboxylic triazole derivatives
    Li, Xu-Jun
    Zhang, Wei
    Zhao, Chi-Na
    Wu, Qing-Lai
    Li, Jun-Kai
    Xu, Zhi-Hong
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2021, 23 (05) : 452 - 465
  • [2] The Synthesis of (1,3,4-Oxadiazol-2-yl)Acrylic Acid Derivatives with Antibacterial and Protistocidal Activities
    L. D. Popov
    A. A. Zubenko
    L. N. Fetisov
    Yu. D. Drobin
    A. I. Klimenko
    A. N. Bodryakov
    S. A. Borodkin
    I. E. Melkozerova
    Russian Journal of Bioorganic Chemistry, 2018, 44 : 238 - 243
  • [3] The Synthesis of (1,3,4-Oxadiazol-2-yl)Acrylic Acid Derivatives with Antibacterial and Protistocidal Activities
    Popov, L. D.
    Zubenko, A. A.
    Fetisov, L. N.
    Drobin, Yu. D.
    Klimenko, A. I.
    Bodryakov, A. N.
    Borodkin, S. A.
    Melkozerova, I. E.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2018, 44 (02) : 238 - 243
  • [4] Synthesis and hydrazinolysis of β-(1,3,4-oxadiazol-2-yl)pyridines
    O. U. Nesterova
    A. S. Pugachova
    M. V. Voevudsky
    O. V. Krischik
    V. I. Musatov
    Chemistry of Heterocyclic Compounds, 2011, 46 : 1520 - 1526
  • [5] SYNTHESIS AND HYDRAZINOLYSIS OF β-(1,3,4-OXADIAZOL-2-YL)PYRIDINES
    Nesterova, O. U.
    Pugachova, A. S.
    Voevudsky, M. V.
    Krischik, O. V.
    Musatov, V. I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 46 (12) : 1520 - 1526
  • [6] THE SYNTHESIS OF ANTIHYPERTENSIVE 3-(1,3,4-OXADIAZOL-2-YL)PHENOXYPROPANOLAMINES
    SCHLECKER, R
    THIEME, PC
    TETRAHEDRON, 1988, 44 (11) : 3289 - 3294
  • [7] Synthesis, fungicidal activity and phloem mobility of phenazine-1-carboxylic acid-alanine conjugates
    Niu, Junfan
    Nie, Danyue
    Yu, Diya
    Wu, Qinglai
    Yu, Linhua
    Yao, Zongli
    Du, Xiaoying
    Li, Junkai
    PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2017, 143 : 8 - 13
  • [8] BENZOTHIAZOLE DERIVATIVES .4. SYNTHESIS OF SOME 2-(1,3,4-OXADIAZOL-2-YL) AND 6-(1,3,4-OXADIAZOL-2-YL) BENZOTHIAZOLES AND 2-(1,3,4-THIADIAZOL-2-YL) AND 6-(1,3,4-THIADIAZOL-2-YL) BENZOTHIAZOLES AS POTENTIAL ANTIINFLAMMATORY AGENTS
    SAWHNEY, SN
    SINGH, J
    BANSAL, OP
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1974, 51 (10) : 886 - 890
  • [9] Synthesis and bioactivities of phenazine-1-carboxylic piperazine derivatives
    Han, Fei
    Yan, Ru
    Zhang, Min
    Xiang, Zhu
    Wu, Qinglai
    Li, Junkai
    NATURAL PRODUCT RESEARCH, 2020, 34 (09) : 1282 - 1287
  • [10] Synthesis and functionalization of the 3-(1,3,4-oxadiazol-2-yl)-1h-indoles
    S. B. Alyab’ev
    D. V. Kravchenko
    A. V. Ivashchenko
    Chemistry of Heterocyclic Compounds, 2009, 45 : 1270 - 1275