ORGANIC PHOSPHORUS COMPOUNDS 102.¹ AMINOOXYALKYLPHOSPHONIC ACIDS AND DERIVATIVES

Abstract

Condensation of α-hydroxyalkylphosphonates, 1, with N-hydroxy-phthalimide using Mitsunobu's condition yields 1-phthalimido-N-oxyalkylphosphonates, 2, which on treatment with hydrazine give 1-aminooxyalkylphosphonates, 3. Hydrolysis of these with HCl produces 1-aminooxyalkylphosphonic acids, 4, in good yield. The reactions of 3 with dinitrodiphenyl ether, isocyanides, aldehydes and ketones are also reported.

1-Aminooxy-2-phenylethylphosphonic acid, 4g, is only a weak inhibitor of PAL, but 4i is a good inhibitor of anthocyanin synthesis. 4g exhibits weak antifungal activity (against Botrytis cinerea) and 5a and 5b show herbicidal activity against dicotyledonous weeds.

Key Words:

• 1-Aminooxyalkylphosphonates
• 1-aminooxyalkylphosphonic acids
• physical properties
• NMR-spectra
• biological activity