Synthesis and biological activity of O, O′-dialkyl-5-aryl-1-hydroxy-2E,4E-pentadienylphosphonates

A series of O,O-dialkyl-5-aryl-1-hydroxy-2E,4E-pentadienylphosphonates with structures similar to that of abscisic acid were synthesized by the reactions of dialkyl phosphites with 5-aryl-2E,4E-pentadienaldehydes. The structures of all new compounds have been confirmed by ¹H NMR, ³¹P NMR, and IR spectroscopy and by elemental analysis or MS. The configurations of carbon-carbon double bonds were determined by X-ray diffraction analyses. The bioassays showed that some of these compounds exhibit inhibitory activity on the elongation of wheat coleoptile. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:303–307, 2000