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Four kinds of alkyl p-(methylcarbamoyl)oxybenzoates and carbamates of furfural oxime and of 5-methylfurfural oxime have been newly synthesized. In addition, when alkyl or phenyl salicylate instead of alkyl p-hydroxybenzoates reacted with methyl isocyanate, benz(e)-N-methyl-1, 3-oxazadihydroine-2,4-dione, a heterocyclic compound, was obtained probably due to decomposition of the unstable methylcarbamoyl salicylates followed by ring formation of the residual side chains. All of the carbamates except for furfural oxime carbamate exerted the relaxation of rabbit’’s ileum at the concentrations over 105g/ml. On the other hand, the p-(methylcarbamoyl)oxybenzoates exhibited antibacterial activity on Salmonella paratyphi A, Shigella dysenteriae 2, and Staphylococcus aureus at the concentration range of 50-500mcg/ml, while no such activity was observed with furfural oxime carbamate.
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