betadex and norflurazone

High pesticide concentrations in soil from spills or discharges can result in point-source contamination of ground and surface waters. Cost-effective technologies are needed for on-site treatment that meet clean-up goals and restore soil function. Remediation is particularly challenging when a mixture of pesticides is present. beta-Cyclodextrins (BCD) solutions are employed to enhance the aqueous solubility of a hydrophobic organic compound. The interaction of norflurazon (NFL) with BCD yielded the formation of inclusion complexes at a 1:1 stoichiometric ratio in solution. The change of the sorption parameter K(d) as affected by the time, and desorption studies of NFL previously adsorbed on four different soils with different characteristics have been performed in the presence of 0.01 M BCD or 0.01 M Ca(NO(3))(2) acting as extractant solutions. NFL sorption increased with the residence time in soil, making it more resistant to be desorbed. Likewise, leaching experiments were performed in packed soil columns eluting initially with distilled water, with the aim to simulate the herbicide drainflow losses because of rainfall, approaching to a more realistic environment, and later with 0.01 M BCD solutions to extract the residual NFL bound. The results showed that removal efficiencies of the different flushing systems were significantly influenced by their affinity and selectivity for the contaminants in the soil matrix as well as BCD adsorption on soils, since this could act like a bridge between pesticide molecule and soil particles increasing the stay of NFL in soil. These results are further information to be in condition to predict the potential effect of the BCD solutions on soil chemical decontamination in the field situation assessing the likelihood for bioremediation of a pesticide contaminated-soil, since the increasing in hydrosolubility of the contaminants means the first step before microorganism uptaken.

Topics: beta-Cyclodextrins; Environmental Restoration and Remediation; Pesticides; Pyridazines; Soil Pollutants; Solutions

The effects of beta-cyclodextrin (BCD) on the sorption-desorption and transport processes of the herbicide norflurazon (NFL) in soils of different characteristics when both are applied simultaneously have been investigated. Adsorption-desorption studies of NFL on six soils of very different characteristics in the presence of BCD have been performed using a batch equilibration method and correlated to its mobility in homogeneous hand-packed soil columns. NFL determinations were undertaken by HPLC equipped with a diode array detector at a wavelength of 220 nm. BCD was also analyzed by HPLC with fluorimetric detection using a postcolumn reaction. The interaction of NFL with BCD yielded the formation of an inclusion complex in solution. When this complex is applied to soils, a large decrease in NFL adsorption capacity and an increase in its desorption were observed, due to the higher tendency of NFL-BCD complexes to remain in solution. The results obtained in adsorption and soil column experiments indicated that the influence of BCD on NFL mobility and availability depends on the different affinities of BCD to be sorbed on soils of different characteristics and on the concentration of BCD used. The lower the concentration of BCD added, the more tenaciously it adheres to the soil, and most of the BCD molecules would be adsorbed, providing a coating to soil particles that acts as a bridge between NFL and the soil surface, acting as an adsorbent and retarding the mobility of the herbicide. At higher concentrations of BCD, or in soils where its adsorption is very low, most of the BCD molecules are in the aqueous phase and NFL molecules tend to be complexed with BCD in solution, acting then as a solubilizing agent.

Topics: Adsorption; beta-Cyclodextrins; Chemical Phenomena; Chemistry, Physical; Chromatography, High Pressure Liquid; Herbicides; Pyridazines; Soil

The effect of beta-cyclodextrin (beta-CD) on the removal of the herbicide norflurazon (NFL) from soils has been investigated. The interaction of NFL with beta-CD in solution yielded the formation of a water-soluble inclusion complex at 1:1 stoichiometric ratio, which gave an increase in NFL solubility. Desorption studies of NFL previously adsorbed on six soils of different characteristics have been performed in the presence of 0.01 M beta-CD or 0.01 M Ca(NO(3))(2) as extractant solutions. Positive hysteresis was observed in all soils when 0.01 M Ca(NO(3))(2) solution was used, indicating that desorption of NFL from these soils was not completely reversible. On the contrary, the application of beta-CD solutions to soils where NFL had been previously adsorbed increased very much its desorption, and a negative hysteresis was obtained for all soils studied; that is, more NFL was desorbed with respect to NFL adsorption isotherm. A clear relationship was observed between the physicochemical characteristics of the soils and the beta-CD concentration necessary to remove the herbicide, the percentages of desorption observed for each soil being inversely related to the values obtained for the Freundlich sorption capacity parameter of the herbicide, K(f). In general, high desorption yields can be obtained with very low beta-CD concentrations, which is an important advantage from an economic point of view, although in those soils that present an extremely high NFL adsorption, higher amounts of beta-CD should be used. The results obtained indicate the high extracting power of beta-CD toward the herbicide previously adsorbed on the soils and the potential use of beta-CD for in situ remediation of pesticide-contaminated soils.

Topics: Adsorption; beta-Cyclodextrins; Chemical Phenomena; Chemistry, Physical; Herbicides; Pyridazines; Soil; Solutions

The formulation of inclusion complexes of the herbicide norflurazon as guest and beta-cyclodextrin (beta-CD) as host has been studied as a first step in the use of cyclodextrins to obtain improved formulations of this herbicide. The interaction of norflurazon with beta-CD produced the formation of an inclusion complex in solution and in solid state. The inclusion of norflurazon in beta-CD in solution was studied by phase solubility, and an apparent stability constant of 360 M(-)(1), a 1:1 stoichiometric ratio for the complex, and up to 5-fold increase in norflurazon solubility were determined. Three processing methods (kneading, spray drying and vacuum evaporation) were used to prepare norflurazon-beta-CD solid inclusion complexes. X-ray diffraction, infrared spectroscopy, differential scanning calorimetry, and scanning electron microscopy techniques were used to study the solid complexes. From the different solid systems, an increase of norflurazon aqueous dissolution rate was obtained in comparison to the uncomplexed herbicide. This finding is a first step to obtain controlled release and/or protective formulations of norflurazon, which allow a more rational application of norflurazon, diminishing the use of organic solvents and increasing its efficacy.

Topics: beta-Cyclodextrins; Calorimetry, Differential Scanning; Cyclodextrins; Herbicides; Kinetics; Pyridazines; Solubility; Solutions; Spectroscopy, Fourier Transform Infrared; Structure-Activity Relationship; X-Ray Diffraction