SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 02: 388 - 392

DOI: https://doi.org/10.6023/cjoc1108151

研究简报

4-(7-甲氧基-2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-苄亚氨基噻唑的合成与生物活性

  • 沈芳 ,
  • 胡艾希 ,
  • 罗先福 ,
  • 叶姣 ,
  • 欧晓明
展开
  • a 湖南大学化学化工学院 长沙 410082;
    b 湖南化工研究院 长沙 410007

收稿日期: 2011-08-15

  修回日期: 2011-09-30

  网络出版日期: 2012-03-09

基金资助

国家科技支撑计划(No. 2011BAE06B01)资助项目.

收起

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

  • SHEN Fang ,
  • HU Ai-Xi ,
  • LUO Xian-Fu ,
  • YE Jiao ,
  • OU Xiao-Ming
Expand
  • a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b Hunan Research Institute of Chemical Industry, Changsha 410007

Received date: 2011-08-15

  Revised date: 2011-09-30

  Online published: 2012-03-09

Supported by

Project supported by the National Technology R&D Program of China (No. 2011BAE06B01).

Fold

摘要

呋喃酚经醚化、傅克酰化、α-溴代、噻唑环化和亚胺化等反应合成了16 种4-(7-甲氧基-2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-苄亚氨基噻唑新化合物. 化合物的结构经1H NMR、质谱和元素分析等确证. 杀虫活性实验结果表明, 化合物 2a 和 2i 在500 mg/L 对棉红蜘蛛死亡率分别为53.10%和67.71%, 杀菌活性实验结果表明, 化合物2a 和2k 在25mg/L 对油菜菌核病菌抑制率分别为57.9%和59.8%, 除草活性实验结果表明, 2l 在2250 g·ai/ha 浓度下对苘麻、刺苋藜具有一定的除草活性.

关键词： 4-(7-甲氧基-2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-苄亚氨基噻唑; 合成; 杀虫活性; 杀菌活性; 除草活性

本文引用格式

沈芳 , 胡艾希 , 罗先福 , 叶姣 , 欧晓明 . 4-(7-甲氧基-2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-苄亚氨基噻唑的合成与生物活性[J]. 有机化学, 2012 , 32(02) : 388 -392 . DOI: 10.6023/cjoc1108151

Abstract

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, α-bromation, cyclization of thiazole and imidization. Their structures were clearly established by 1H NMR, MS spectra and elemental analysis. The preliminary bioassays indicated that compounds 2a and 2i 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 2l showed different degrees of herbicidal activity against A. theophrasti, A. spinosus L and C. album at 2250 g·ai/ha.

Key words： (E)-2-benzylidenimino-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazole; synthesis; insecticidal activity; fungicidal activity; herbicidal activity

参考文献

[1] Zhang, J. Y.; Hu, A. X.; Wang, Y.; Xiao, X. H.; Guo, J. B.; Luo, X. F. Chin. J. Chem. Eng. 2009, 17, 42.

[2] Brkic, D. V.; Vitorovic, S. L.; Gasic, S. M.; Neskovic, N. K. Environ. Toxicol. Pharmacol. 2008, 25, 334.

[3] Marcantonio, K. M.; Frey, L. F.; Murry, J. A.; Chen, C. Y. Tetrahedron Lett. 2002, 43, 8845.

[4] Jackson, A.; Heys, G.; Grayson, J. I.; Clarke, R. US 5705652, 1998[Chem. Abstr. 1997, 126, 277471].

[5] Hu, D. Y.; Song, B. A.; He, W.; Yang, S.; Jin, L. H. Chin. J. Synth. Chem. 2006, 14, 319 (in Chinese). (胡德禹, 宋宝安, 何伟, 杨松, 金林红, 合成化学, 2006, 14, 319.)

[6] Hu, A. X.; He, L. M.; Dong, M. Y.; Zhang, J. Y.; Ou, X. M. Chem. J. Chin. Univ. 2008, 29, 739 (in Chinese). (胡艾希, 贺丽敏, 董敏宇, 张建宇, 欧晓明, 高等学校化学学 报, 2008, 29, 739.)

[7] Desai, S. B.; Desai, P. B.; Desai, K. R. Herercycl. Commun. 2001, 7, 83.

[8] Shao, L.; Zhang, Q.; Zhou, X.; Jin, Z.; Liu, J. B.; Fang, J. X. Chem. J. Chin. Univ. 2007, 28, 270 (in Chinese). (邵玲, 张青, 周欣, 金钟, 刘建兵, 方建新, 高等学校化学学报, 2007, 28, 270.)

[9] Luo, X. F.; Hu, A. X.; Wang, Y.; Ye, J.; Wang, X. G.; Ou, X. M. Chem. J. Chin. Univ. 2011, 31, 2800 (in Chinese). (罗先福, 胡艾希, 王宇, 叶姣, 王晓光, 欧晓明, 高等学校化学 学报, 2011, 31, 2800.)

[10] Ye, J.; Peng, J. M.; Hu, A. X.; Wang, C.; Zou, M.; Ou, X. M. Chin. J. Org. Chem. 2011, 31, 886 (in Chinese). (叶姣, 彭俊梅, 胡艾希, 王超, 邹孟, 欧晓明, 有机化学, 2011, 31, 886.)

[11] Hu, A. X.; Qin, Z.; Chen, P.; Ye, J. Chin. J. Org. Chem. 2010, 30, 923 (in Chinese). (胡艾希, 覃智, 陈平, 叶姣, 有机化学, 2010, 30, 923.)
Options
文章导航

/

〈 〉