2-Fluoro and 2-Methoxycarbonyl Epoxy-β-ionylideneacetic Acids as Abscisic Acid Analogs

Abstract

Abscisic acid (ABA) is easily isomerized to inactive trans-ABA by light. To solve this problem, two variations of epoxy-β-ionylideneacetic acid were synthesized as ABA analogs, each of them having a methoxycarbonyl or a fluoric substituent at the 2-position. The 2E-, and 2Z-fluorinated analogs showed moderate growth inhibitory activity toward rice seedlings and lettuce seeds, whereas the methoxycarbonyl analog was inactive toward rice seedling growth and only partially active toward lettuce germination. The 2E-fluorinated analog was extensively isomerized to the 2Z-isomer by UV irradiation. We think that a steric requisite for the 2E-position was high, and that the fluorine substituent was not effective for fixing the 2-double bond in the E-configuration.