Synthesis and Herbicidal Activities of 5-Benzyloxymethyl-3-(thiophen-5-yl)-1,2-isoxazoline and Their Related Derivatives

5-Benzyloxymethyl-3-(thiophen-5-yl)-1,2-isoxazoline 유도체의 합성과 제초활성

  • Published : 2007.06.30

Abstract

Nobel series of 5-benzyloxymethyl-3-(thiophen-5-yl)-1,2-isoxazoline derivatives were designed and synthesized. The herbicidal activities of these compounds to main dominant weeds to these compounds were evaluated in pot tests that simulated rice paddy conditions. Most of the compounds showed high herbicidal activity to main dominant weeds occurring in rice field without the serious rice injury.

Keywords

thiophene;isoxazoline;herbicide;rice

References

  1. Ryu, E. K., H. R. Kim, D. J. Jeon, K. M. Kim, J. N. Lee, H. C. Kim, K. S. Hong (2002) Preparation of herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives for weed control in rice. WO 2002019825
  2. Jeon, D. J., Y. M. Kim, K. Y. Park, H. R. Kim, J. H. Song, J. S. Kim, and E. K. Ryu (2003) Synthesis and herbicidal properties of 2-(5-isoxazolinemethoxyphenyl)4,5,6,7-tetrahydro-2H-indazole and their related derivatives. Korean J. Pestic. Sci. 7(4):310-313
  3. Ryu, E. K., D. J. Jeon, J. H. Song, H. R. Kim, J. N. Lee, K. M. Kim, K. Y. Cho (2001) Herbicidal 2-(5-isoxazolinylmethoxyphenyl)-4,5,6, 7 -tetrahydro-2H-i ndazole derivatives. Korean Pat. 0289470
  4. Hwang, I. T., H. R. Kim, D. J. Jeon, K. S. Hong, J. H. Song, and K. Y. Cho (2005) 5-(2,6-difluorobenzyl) oxymethyl- 5-methyl-3-(3-methylthiophen-2-yl) -1,2-isoxazoline as a useful herbicide. J. Agrie. Food Chem. 53:8639-8643 https://doi.org/10.1021/jf051284f
  5. Joachim, R, E. Kart, T. Hans, K. Thomas, W. Karl-Otto, W. Bruno, F. Juergen, and M. Nobert (1989) Isoxazoline, Verfahren zu ihrer Herstellung sowie ihre Verwendung. Eur. Pat. 0334120 A1
  6. Lee, J. N., D. J. Jeon, Y. M. Kim, K. M. Kim, and J. H. Song (2000) Synthesis of new pyrazolylisoxazolines via 1,3-dipolar cycloaddition reacion of bicyclic sydnone with benzyl propiolate. Bull. Korean Chem. Soc. 21 (8):761 -762 https://doi.org/10.1007/BF02705517
  7. David, M. and P. Bipin (1992) Herbicidal compounds, Eur. Pat. 0514987 A1