Aryl-Substituted α-Aminooxycarboxylic Acids

Certain herbicidal aminooxyisovalerate analogs were noted in whole plant phytotoxicity bioassays to cause disoriented roots. Since this symptom is often characteristic of interference with the transport of the plant hormone auxin, the ability of several of these compounds to compete for the N-1-naphthylphthalamic acid (NPA) binding site in corn (Zea mays L.) coleoptile membranes was measured. Significant NPA binding activity was found, expecially for the 2,4-dichlorophenyl analog. Application of structure-activity principles from traditional auxin transport inhibitors to this new class of molecules led to the synthesis of the naphthyl analogue. This molecule was extremely active in competing for NPA binding and in eliciting whole plant growth regulator effects. Possible relationships between these molecules and the mode of auxin transport are discussed.