Chinese Journal of Organic Chemistry >
Synthesis and Fungicidal Activity of 2-(2,2-Dimethyl-2,3-dihydro-benzofuran-5-yl)-2-(1,2,4-triazole-1-methyl)-1,3-dioxolane
Received date: 2014-06-15
Revised date: 2014-07-07
Online published: 2014-07-15
Supported by
Project supported by the State Commission of Science Technology of China (No.2011BAE06B01).
Benzofuran and 1,2,4-triazole have been rewarded with much priority for their broad spectrum of biological activities, especially in the agricultural field. In this specific domain, they have always been used as fungicides, pesticide and plant growth regulators etc. Consequently, a series of new compounds containing 1,2,4-triazole, 1,3-dioxolane and benzofuran moieties were designed and synthesized. 1-(2,2-Dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone (4a) were prepared from 1-(4-hydroxyphenyl)ethanone in three steps. Subsequently, 2-(2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(1,2,4-triazol-1-methyl)-1,3-dioxolane (1a~1l) were synthesized from compounds 4a~4c. All compounds were verified by NMR and elemental analysis. Additionally, their fungicidal activities were evaluated against 7 kinds of crop fungus. The compounds 1a, 1b, 1e, 1f, 1g and 1l had relatively good inhibitory activity against Sclerotonia sclerotiorum, and the inhibitory rate were above 70% at 25 mg/L. Meanwhile, compounds 1a and 1b possessed potent inhibitory activity (80%) against Blumeria graminis at 500 mg/L.
Li Wan , Tang Jiangang , Hu Aixi , Ye Jiao , Yang Zihui , Ou Xiaoming . Synthesis and Fungicidal Activity of 2-(2,2-Dimethyl-2,3-dihydro-benzofuran-5-yl)-2-(1,2,4-triazole-1-methyl)-1,3-dioxolane[J]. Chinese Journal of Organic Chemistry, 2014 , 34(11) : 2272 -2278 . DOI: 10.6023/cjoc201406021
[1] Campbell, S.; David, M. D.; Woodward, L. A.; Li, Q. X. Chemosphere 2004, 54, 1155.
[2] Pang, J. Y.; Xu, Z. L. Chin. J. Org. Chem. 2005, 25, 25 (in Chinese).(庞冀燕, 许遵乐, 有机化学, 2005, 25, 25.)
[3] Xue, N. D. J. Hunan Agric. Univ. (Nat. Sci.) 2000, 26, 236 (in Chinese). (薛南冬, 湖南农业大学学报(自然科学版), 2000, 26, 236.)
[4] Brkic, D.V.; Vitorovic, S. L.; Gasic, S. M.; Neskovic, N. K. Environ. Toxicol. Pharmacol. 2008, 25, 334.
[5] Nagaraju, M.; Deepthi, E. G.; Ashwini, C.; Vishnuvardhan, M. V.; Lakshma, N. V.; Chandra, R.; Ramakrishna, S.; Gawali, B. B. Bioorg. Med. Chem. Lett. 2012, 22, 4314.
[6] Wang, X. C.; Quan, Z. J.; Li, Z. Chin. J. Org. Chem. 2005, 25, 1089 (in Chinese). (王喜存, 权正军, 李政, 有机化学, 2005, 25, 1089.)
[7] Hu, A. X.; Dou, J.; Ye, J.; Shi, L.; Wu, Z. L. CN 102786515, 2012 [Chem. Abstr. 2012, 158, 11629].
[8] Hu, A. X.; Wei, L.; Ye, J.; Shen, F.; Li, W.; Ou, X. M. CN 103145700, 2013 [Chem. Abstr. 2013, 159, 133919].
[9] Hu, A. X.; Li, Q.; Fu, E. X.; Wu, Z. L.; Ou, X. M. CN 103342703, 2013 [Chem. Abstr. 2013, 159, 592774].
[10] Tan, X. S. M.S. Thesis, Central China Normal University, Wuhan, 2000 (in Chinese).(谭效松, 硕士论文, 华中师范大学, 武汉, 2000.)
[11] He, Q. X. M.S. Thesis, Hunan University, Changsha, 2009 (in Chinese).(何奇喜, 硕士论文, 湖南大学, 长沙, 2009.)
[12] Luo, X. F.; Hu, A. X.; Wang, Y.; Ye, J.; Wang, X. G.; Ou, X. M. Chem. J. Chin. Univ. 2011, 32, 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, 32, 2800.)
[13] Shen, F.; Hu, A. X.; Luo, X. F.; Ye, J.; Ou, X. M.; Chin. J. Org. Chem., 2012, 32, 388 (in Chinese). (沈芳, 胡艾希, 罗先福, 叶姣, 欧晓明, 有机化学, 2012, 32, 388.)
[14] Borivoj, R.; Frankko-Filipasic, M. T. US 3320286, 1967 [Chem. Abstr. 1967, 66, 46319].
[15] Brown, F. J.; Bernstein, P. R.; Cronk, L. A.; Dosset, D. L.; Hebbel, K. C.; Maduskuie Jr., T. P.; Shapiro, H. S.; Vacek, E. P.; Yee, Y. K. J. Med. Chem. 1989, 32, 807.
[16] Xu, L. Z.; Jian, F. F.; Niu, S. Y.; Jiang, Z. H. Chem. Res. Chin. Univ. 2004, 20, 558.
[17] Nicolai, S.; Erard, S.; Gonzalez, D. F.; Waser, J. Org. Lett. 2010, 12, 384.
[18] Baddeley, G.; Vickers, M. A. J. Chem. Soc. 1958, 12, 4665.
/
| 〈 |
|
〉 |
