Synthesis and Bioactivity of (E)-2-Benzylidenimino-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazole

被引:14
|
作者
Shen, Fang [1 ]
Hu, Aixi [1 ]
Luo, Xianfu [1 ]
Ye, Jiao [1 ]
Ou, Xiaoming [2 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China
[2] Hunan Res Inst Chem Ind, Changsha 410007, Hunan, Peoples R China
关键词
(E)-2-benzylidenimino-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazole; synthesis; insecticidal activity; fungicidal activity; herbicidal activity; BIOLOGICAL-ACTIVITY; CARBOFURAN;
D O I
10.6023/cjoc1108151
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sixteen (E)-2-benzylidenimino-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazoles were synthesized from 2,3-dihydro-2,2-dimethyl-7-benzofuranol by etherification, Friedel-Crafts acylation, alpha-bromation, cyclization of thiazole and imidization. Their structures were clearly established by H-1 NMR, MS spectra and elemental analysis. The preliminary bioassays indicated that compounds 2a and 21 exhibited insecticidal activity against T. urticae were 53.10% and 67.71% at 500 mg/L. Compounds 2a and 2k exhibited fungicidal activity against S. sclerotiorum were 57.9% and 59.8% at 25 mg/L. Compound 21 showed different degrees of herbicidal activity against A. theophrasti, A. spinosus L and C. album at 2250 g.ai/ha.
引用
收藏
页码:388 / 392
页数:5
相关论文
共 11 条
  • [1] Carbofuran in water: Subchronic toxicity to rats
    Brkic, Dragica V.
    Vitorovic, Slavoljub Lj.
    Gasic, Slavica M.
    Neskovic, Nesko K.
    [J]. ENVIRONMENTAL TOXICOLOGY AND PHARMACOLOGY, 2008, 25 (03) : 334 - 341
  • [2] Desai SB, 2001, HETEROCYCL COMMUN, V7, P83
  • [3] Hu AX, 2008, CHEM J CHINESE U, V29, P739
  • [4] Hu AX, 2010, CHINESE J ORG CHEM, V30, P923
  • [5] [胡德禹 HU Deyu], 2006, [合成化学, Chinese Journal of Synthetic Chemistry], V14, P319
  • [6] Jackson A., 1998, [No title captured], Patent No. [US 5705652, 5705652]
  • [7] Luo XF, 2011, CHEM J CHINESE U, V32, P2800
  • [8] A practical preparation of 5-(ketoaryl)thiazoles
    Marcantonio, KM
    Frey, LF
    Murry, JA
    Chen, CY
    [J]. TETRAHEDRON LETTERS, 2002, 43 (49) : 8845 - 8848
  • [9] Shao L, 2007, CHEM J CHINESE U, V28, P270
  • [10] Ye J, 2011, CHINESE J ORG CHEM, V31, P886