N-METHYL- AND N,N-DIMETHYLCARBAMATES OF HYDROXYBENZALDEHYDE ACETALS AND MERCAPTALS

A series of new N-methyl- and N,N-dimethylcarbamates of hydroxybenzaldehyde acetals and mercaptals has been prepared. The synthesis of these compounds and their physical, anticholinesterase, and insecticidal properties are reported. Considering over-all insecticidal activity, 2-(1,3-dioxolan-2-yl)phenyl N-methylcarbamate has been found outstanding. Furthermore, phenyl N-methylcarbamates with the following ortho-substituents show interesting insecticidal properties: 4-methyl-1,3-dioxolan-2-yl, 4,4-dimethyl-1,3-dioxolan-2-yl, 4,5-dimethyl-1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, and 1,3-dithiolan-2-yl. Salicylaldehyde dimethyl acetal N-methylcarbamate and 2-(1,3-dithiolan-2-yl)phenyl N,N-dimethylcarbamate have remarkable selective toxicides. Meta isomers are less active and para compounds show practically no insecticidal properties. © 1969, American Chemical Society. All rights reserved.