Summary
5,6-Dichloroindole-3-acetic acid (1), a new auxin, has been synthesized by Fischer's indolization. It showed the strongest auxin activity among all the known natural and synthetic auxins in three bioassays (elongation ofAvena coleoptiles, hypocotyl growth inhibition of Chinese cabbage, and hypocotyl swelling of mung bean seedlings). It induced many lateral roots in mung bean seedlings, and resisted peroxidase-catalyzed decomposition.
References
Marumo, S., Abe, H., Hattori, H., and Munakata, K., Agric. biol. Chem.32 (1968) 117.
Marumo, S., Hattori, H., Abe, H., and Munakata, K., Nature219 (1968) 959.
Marumo, S., Hattori, H., and Yamamoto, A., in: Plant Growth Substance, p. 419, Hirokawa Publishing Company Inc., Tokyo 1974.
Fox, S. W., and Bullock, M. W., J. Am. chem. Soc.73 (1951) 2756.
Porter, W. L., and Thimann, K. V., Phytochemistry4 (1965) 229.
Hoffmann, O. L., Fox, S. W., and Bullock, M. W., J. biol. Chem.196 (1952) 437.
Sell, H. M., Wittwer, S. H., Rebstock, T. L., and Redemann, C. T., Pl. Physiol.28 (1952) 481.
Engvild, K. C., in: Hormonal Regulation of Plant Growth and Development, vol. 2, p. 221. Agro Botanical Publishing Company Inc., India 1985.
Böttger, M., Engvild, K. C., and Soll, H., Planta140 (1978) 89.
Katekar, G. F., and Geissler, A. E., Phytochemistry21 (1982) 257.
Katekar, G. F., and Geissler, A. E., Phytochemistry22 (1983) 27.
Engvild, K. C., Acta chem. scand.B 31 (1977) 338.
Baldi, B. G., Slovin, J. P., and Cohen, J. D., J. label. Compd. Radiopharm.22 (1985) 279.
Schneider, E. A., and Whightmann, F., A. Rev. Pl. Physiol.25 (1974) 487.
Meudt, W. J., Ann. N.Y. Acad. Sci.144 (1967) 118.
Bonner, J., Am. J. Bot.36 (1949) 323.
Author information
Authors and Affiliations
Additional information
The bioassy has been routinely conducted in our laboratory in order to examine the long term activity of auxins on the growing intact plants. An extent of the hypocotyl inhibition is in proportion to the amount of 2,4-D and 4-Cl-IAA in a concentration range of 10−6 to 10−4 M.
Rights and permissions
About this article
Cite this article
Hatano, T., Katayama, M. & Marumo, S. 5,6-Dichloroindole-3-acetic acid as a potent auxin: its synthesis and biological activity. Experientia 43, 1237–1239 (1987). https://doi.org/10.1007/BF01945542
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF01945542