The synthesis of two new methacrylates such as 2-[(cyclohexylideneamino)oxy]-2-oxoethyl methylacrylate (CHOEMA) and 2-[(cyclopentylideneamino)oxy]-2-oxoethyl methylacrylate (CPOEMA) are described. The monomers produced from the reaction of corresponding cyclohexanone O-(2-chloroacetyl) oxime and cyclopentanone O-(2-chloroacetyl) oxime with sodium methacrylate was polymerized in 1,4-dioxane solution at 65οC using AIBN as an initiator. The monomers and their polymers were characterized by IR, 1H- and 13C-NMR spectroscopy. The glass transition temperature of the polymers was investigated by DSC and the apparent thermal decomposition activation energies (Ed) were calculated by Ozawa and multiple heating rate kinetics (MHRK) method using the Shimadzu TGA thermobalance. By using gel permeation chromatography, weight-average (Mw) and number-average (Mn) molecular weights and polydispersity indices of the polymers were determined. The antibacterial and antifungal effects of the monomers and polymers were also investigated on various bacteria and fungi. The photochemical properties of the polymers were investigated by UV and FTIR spectra.