CHROMATOGRAPHIC APPROACH IN THE ASSESSMENT OF LIPOPHILICITY OF CHLOROACETAMIDE DERIVATIVES

Abstract

Chloroacetamides are widely used and highly effective herbicides. However, in addition to the positive aspects of application, their residues and metabolites remain in water and soil for a long time, which is why they represent a threat to the ecosystem. Lipophilicity, as the most important physico-chemical parameter closely related to bioavailability or potential biological activity of compounds for the newly synthesized chloroacetamide derivatives was determined computationally by using appropriate software packages, as well as experimentally, by using thin-layer chromatography on reversed phases, RPTLC C18/ UV254s in a mixture of water and four organic modifier, separately. It was found that the chromatographic behavior of the studied derivatives of chloroacetamide is affected to a small extent by the applied organic modifier, and to a greater extent by the total number of carbon atoms in the structure of their molecules, as well as by the type of hydrocarbon substituents. Dependence between the chromatographic parameters and the software-derived values of the partition coefficient as a standard measure of lipophilicity, as well as the relevant parameters of acute ecotoxicity, was examined by using the linear regression analysis. The reliable application of chromatographic parameters in the assessment of lipophilicity and ecotoxicity of the tested chloroacetamide derivatives was confirmed by the obtained mathematical models.