Preparation and Characterization of Butachlor/(2-Hydroxypropyl)-β-cyclodextrin Inclusion Complex: Improve Soil Mobility and Herbicidal Activity and Decrease Fish Toxicity

Abstract

A water-soluble inclusion complex for butachlor was prepared by complexation with (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD). Phase solubility results indicated a 1:1 stoichiometric ratio with an apparent stability constant of 864.3 M–1 in the obtained solid complex. The formation of the complex was confirmed by 1H nuclear magnetic resonance, Fourier transform infrared, and differential scanning calorimetry spectra. Coupled with the molecular docking results, butachlor was considered to be completely included in HP-β-CD cavity. Butachlor complexation with HP-β-CD decreased its adsorption capacity and enhanced its mobility in soil. The inclusion complex displayed better herbicidal activities than free butachlor. The 96 h median lethal concentration values of the inclusion complex and free butachlor was 2.30 and 0.65 mg L–1, respectively, for zebrafish, indicating that the complexation could significantly reduce toxicity to fishes. The present study provides an approach to develop environment-friendly formulations using CDs for herbicides.