Synthesis, properties and fungicidal activity of 4-hydroxy(alkoxy)imino-oxazolidin-2-ones

Article abstract of DOI:10.3797/scipharm.aut-01-197

4-Hydroxyimino-oxazolodin-2-ones (3) were prepared by hydroxylaminolysis of 4-alkoxy-3-oxazolin-2-ones (2). Treatment of 3a with ethyl chloroformate in a molar ratio of 1:1 afforded 6, whereas the reaction 3a with two equivalents of ethyl chloroformate produced 4 and 5. By reacting 3a,d with diphosgene or thiophosgene the novel tetrahydro-oxazolo [4,3-c]1,2,4-oxadiazoles 7 could be obtained in low yields. From the prepared novel compounds only 3a displayed a remarkable fungicidal activity at 2 ppm.