Synthesis and activity of another seleniated auxin: 2,4-dichlorophenylselenoacetic acid

The synthesis of 2,4-dichlorophenylselenoacetic acid (2,4-D-Se) may be completed in three steps starting from 2,4-dichloroaniline. The selenium is inserted in the molecule by reaction of a diazonium salt with potassium selenocyanate. 2,4-D-Se has been tested as an auxin in several bioassays including the regeneration of somatic embryos, adventitious root formation and the associated temporary increase of endogenous auxins at the induction phase, and callus formation, and compared with the natural auxin indoleacetic acid (IAA), the classical synthetic auxin(s) naphthaleneacetic acid (NAA) and/or 2,4-dichlorophenoxyacetic acid (2,4-D), and with the synthetic seleniated IAA, 3-(benzo[b] selenienyl) acetic acid, BSAA. These biological assays classified 2,4-D-Se together with BSAA among the most powerful synthetic auxins. The role of selenium is briefly discussed.