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Synthesis and Herbicidal Activity of 3-Hexyl-4-R-6,7-dimethoxy Isocoumarin
Corresponding Author(s) : Jing Qian Huo
Asian Journal of Chemistry,
Vol. 28 No. 3 (2016): Vol 28 Issue 3
Abstract
According to Suzuki reaction, four kinds of 3-hexyl-4-R-6,7-dimethoxy isocoumarin derivatives have been designed and synthesized with the 3-hexyl-4-iodo-6,7-dimethoxy isocoumarin as raw materials. Their structures were characterized by 1H NMR, 13C NMR and mass spectrometry. The herbicidal activity of target compounds was studied through a small cup test. The results showed that the inhibition rates of compounds 1 and 2 on the root of Amaranthus retroflexus L were higher than 80 % at the concentration of 250 mg/L, while the inhibition rate of compound 3 to the stem of Setaria viridis (L.) Beauv. was over 80 % at the concentration of 500 mg/L. Compounds 1, 2 and 3 were safe to the sorghum growth at the same concentration.
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- A. Suzuki, J. Organomet. Chem., 576, 147 (1999); doi:10.1016/S0022-328X(98)01055-9.
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References
S.Y. Zhang, L. Meng, W.Y. Gao, N.N. Song, W. Jia and H.Q. Duan, China J. Chinese Mater. Medica, 30, 410 (2005).
J. Arunpanichlert, V. Rukachaisirikul, Y. Sukpondma, S. Phongpaichit, S. Tewtrakul, N. Rungjindamai and J. Sakayaroj, Chem. Pharm. Bull. (Tokyo), 58, 1033 (2010); doi:10.1248/cpb.58.1033.
L. Apostolakos, P. Livanos and B. Galatis, Cell Motil. Cytoskeleton, 66, 342 (2009); doi:10.1002/cm.20366.
R.D. Barry, Chem. Rev., 64, 229 (1964); doi:10.1021/cr60229a002.
F. Takuya, JP Patent JP 60142976 (1985).
M. Ryoichi and Y. Takeo, JP Patent JP 0597841 (1993).
K. Hemmi, J.W. Harper and J.C. Powers, Biochemistry, 24, 1841 (1985).
J.K. Kendall, T.H. Fisher, H.P. Schultz and T.P. Schultz, J. Org. Chem., 54, 4218 (1989); doi:10.1021/jo00278a043.
L. Li, J.F. Yang and X.G. Yuan, J. Nan Jing Normal Univ. (Eng. Technol.), 5, 64 (2005).
E. Napolitano, Org. Prep. Proced. Int., 29, 631 (1997); doi:10.1080/00304949709355245.
J.Q. Huo, J.H. Xing, L.H. Zhang, Z.H. Kang and J.L. Zhang, J. Intergrat. Agric., 13, 804 (2014).
A. Suzuki, J. Organomet. Chem., 576, 147 (1999); doi:10.1016/S0022-328X(98)01055-9.
A.N. Bumagin, V.V. Bykov and I.P. Beletskaya, Bull. Acad. Sci. USSR, Div. Chem. Sci., 38, 2206 (1989); doi:10.1007/BF00962156.
H.J. Dong, X.D. Ban, C. Li, J.Q. Huo, Z.H. Gong, Z.H. Kang, J.G. Dong and J.L. Zhang, Asian J. Chem., 26, 3623 (2014); doi:10.14233/ajchem.2014.16703.