Application of various methods to determine the lipophilicity parameters of the selected urea pesticides as predictors of their bioaccumulation

Abstract

Different lipophilicity procedures including a newly developed (based on Ościk's equation) was applied in order to compare various urea pesticides with herbicidal and also insecticidal activity, such as monolinuron, chlorotoluron, diuron, isoproturon, linuron, dimefuron, diflubenzuron, teflubenzuron and lufenuron. Lipophilicity parameters (R_MWS and R_MW0) of nine examined pesticides were determined on the chromatographic plates RP-8F₂₅₄ with the use of methanol–water as a mobile phase_. Similarity analysis enabled to group all examined pesticides depending on their lipophilic character and allowed to perform a more objective comparison of different lipophilicity parameters obtained for investigated compounds by means of thin-layer chromatography and by the use of computational methods. It was stated that with the number of fluorine in examined pesticides, the lipophilic character of insecticides and also their tendency to bioaccumulation in the living systems increases noticeably. The results of this work confirmed that a new procedure for determining the lipophilicity parameter (R_MW0) by Ościk's equation could be a suitable tool in the prediction of pesticide bioaccumulation in living system and may be used as an indicator in design of new urea pesticides, which will be safe for humans and the environment.

Keywords:

• Pesticides
• lipophilic parameter
• similarity analysis
• bioaccumulation
• QSAR

Funding

This research was financed by the Medical University of Silesia as part of statutory research project in 2014 year, project no. KNW-1-006/N/4/0.