Synthesis and Fungicidal Activity of 2,5-Disubstituted-1,3,4-oxadiazole Derivatives

被引:11
|
作者
Liu, Jianchao [1 ]
Wang, Weidong [1 ]
He, Hongwu [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Wuhan 430079, Peoples R China
基金
中国国家自然科学基金;
关键词
1,3,4-oxadiazole; pyridine ring; thiazole ring; fungicidal activity; 1,3,4-OXADIAZOLE;
D O I
10.6023/cjoc201403013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of new 2,5-disubstituted-1,3,4-oxadiazole derivatives have been designed and synthesized by adding pyridine ring and thiazole ring to the structure of 1,3,4-oxadiazole. The structures of target compounds have been confirmed by H-1 NMR, EI-MS, IR spectroscopy and elemental analyses. The structure of 2-[(6-pyridin-3-yOmethylthio]-5-(pyridin-4-yl)-1,3,4-oxadazole has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that some compounds possess potential fungicidal activities against Fusarium oxyporium, Gibberella zeae, Rhizoctonia solani, Dothiorella gregaria and Colletotrichum gossypii at a dosage of 5.0 X 10(-5) g/mL. The fungicidal activities of 1,3,4-oxadiazole derivatives adding thiazole ring were better than those of those adding pyridine ring.
引用
收藏
页码:1447 / 1451
页数:5
相关论文
共 16 条
  • [1] Fragment-to-Hit-to-Lead Discovery of a Novel Pyridylurea Scaffold of ATP Competitive Dual Targeting Type II Topoisomerase Inhibiting Antibacterial Agents
    Basarab, Gregory S.
    Manchester, John I.
    Bist, Shanta
    Boriack-Sjodin, P. Ann
    Dangel, Brian
    Illingworth, Ruth
    Sherer, Brian A.
    Sriram, Shubha
    Uria-Nickelsen, Maria
    Eakin, Ann E.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (21) : 8712 - 8735
  • [2] Burbuliene Milda Malvina, 2004, Farmaco (Lausanne), V59, P767, DOI 10.1016/j.farmac.2004.05.007
  • [3] Syntheses and insecticidal activity of new 2-(5-(trifluoromethyl)pyridyloxymethyl)-1,3,4-oxadiazoles
    Cao, S
    Qian, XH
    Song, GH
    Huang, QC
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2002, 117 (01) : 63 - 66
  • [4] Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (thiadiazoles)
    Chen, HS
    Li, ZM
    Han, YF
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (11) : 5312 - 5315
  • [5] Synthesis and herbicidal activity of O,O-dialkyl phenoxyacetoxyalkylphosphonates containing fluorine
    Chen, T
    Shen, P
    Li, YJ
    He, HW
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (02) : 291 - 295
  • [6] New class of potent antitumor acylhydrazone derivatives containing furan
    Cui, Zining
    Li, Ying
    Ling, Yun
    Huang, Juan
    Cui, Jingrong
    Wang, Ruiqing
    Yang, Xinling
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) : 5576 - 5584
  • [7] HYDRAZONES .3. INTRAMOLECULAR 1,3-DIPOLAR ADDITIONS INVOLVING NITRO- AND CARBONYL GROUPS
    GIBSON, MS
    [J]. TETRAHEDRON, 1962, 18 (DEC) : 1377 - &
  • [8] Novel and orally active 5-(1,3,4-oxadiazol-2-yl)pyrimidine derivatives as selective FLT3 inhibitors
    Ishida, Hiroshi
    Isami, Shoichi
    Matsumura, Tsutomu
    Umehara, Hiroshi
    Yamashita, Yoshinori
    Kajita, Jiro
    Fuse, Eiichi
    Kiyoi, Hitoshi
    Naoe, Tomoki
    Akinaga, Shiro
    Shiotsu, Yukimasa
    Arai, Hitoshi
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (20) : 5472 - 5477
  • [9] Synthesis and Antifungal Activity of Novel 2-(1H-Benzimidazol-2-yl)-5-substituted-1,3,4-oxadiazole Derivatives
    Ji, Zengchen
    Liu, Feng
    Zhang, Zeyuan
    Li, Fubo
    Jiang, Lin
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (11) : 2129 - 2133
  • [10] Khan MSY, 2004, INDIAN J CHEM B, V43, P1302