betadex and isoproturon

There is considerable current interest in using biochar (BC) as a soil amendment to sequester carbon to mitigate climate change. However, the implications of adding BC to agricultural soil for the environmental fate of pesticides remain unclear. In particular, the effect of biochars on desorption behavior of compounds is poorly understood. This study examined the influence of BC on pesticide chemical and biological accessibility using the herbicide isoproturon (IPU). Soils amended with 1% and 2% BC showed enhanced sorption, slower desorption, and reduced biodegradation of IPU. Addition of 0.1% BC had no effect on sorption, desorption or biodegradation of IPU. However, the mineralization of (14)C-IPU was reduced by all BC concentrations, reducing by 13.6%, 40.1% and 49.8% at BC concentrations of 0.1%, 1% and 2% respectively. Further, the ratio of the toxic metabolite 4-isopropyl-aniline to intact IPU was substantially reduced by higher BC concentrations. Hydroxypropyl-β-cyclodextrin (HPCD) extractions were used to estimate the IPU bioaccessibility in the BC-amended soil. Significant correlations were found between HPCD-extracted (14)C-IPU and the IPU desorbed (%) (r(2)=0.8518, p<0.01), and also the (14)C-IPU mineralized (%) (r(2)=0.733; p<0.01) for all BC-amended soils. This study clearly demonstrates how desorption in the presence of BC is intimately related to pesticide biodegradation by the indigenous soil microbiota. BC application to agricultural soils can affect the persistence of pesticides as well as the fate of their degradation products. This has important implications for the effectiveness of pesticides as well as the sequestration of contaminants in soils.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Adsorption; beta-Cyclodextrins; Biodegradation, Environmental; Biological Availability; Charcoal; Chromatography, High Pressure Liquid; Herbicides; Phenylurea Compounds; Soil

Numerous reports have indicated that hydrophobic organic compound bioaccessibility in sediment and soil can be determined by extraction using aqueous hydroxypropyl-beta-cyclodextrin (HPCD) solutions. This study establishes the compatibility of HPCD with Selenastrum capricornutum and assesses whether its presence influences the toxicity of reference toxicants. Algal growth inhibition (72 h) showed no significant (P>0.05) difference at HPCD concentrations up to and including 20 mM. HPCD presence did not influence the toxicity of the inorganic reference toxicant (ZnSO(4)), with IC50 values of 0.82 microM and 0.85 microM, in the presence and absence of HPCD (20 mM), respectively. However, HPCD presence (20 mM) reduced the toxicity of 2,4-dichlorophenol and the herbicides diuron and isoproturon. These reductions were attributed to inclusion complex formation between the toxicants and the HPCD cavity. Liberation of complexed toxicants, by sample manipulation prior to toxicity assessment, is proposed to provide a sensitive, high throughput, bioassay that reflects compound bioaccessibility.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; beta-Cyclodextrins; Chlorophenols; Diuron; Dose-Response Relationship, Drug; Ecology; Eukaryota; Herbicides; Phenylurea Compounds; Soil Pollutants; Toxicity Tests

Proton nuclear magnetic resonance spectroscopy ((1)H NMR), which has become an important tool for the study "in situ" of beta-cyclodextrin (beta-CD) complexes, was used to study and structurally characterize the inclusion complexes formed between beta-CD and isoproturon, fenuron, monuron and diuron. The high variation of the chemical shifts from the proton located inside the cavity (H-3, H-5 and H-6) coupled with the non variation of the one located outer sphere of the beta-CD (H-1, H-2 and H-4) provided clear evidence of the inclusion phenomena. Two-dimensional rotating frame Overhauser effect spectroscopy (ROESY) experiments were carried out to further support the proposed inclusion mode.

Topics: beta-Cyclodextrins; Diuron; Magnetic Resonance Spectroscopy; Methylurea Compounds; Molecular Structure; Phenylurea Compounds

The interaction of diuron and isoproturon herbicides with beta-cyclodextrin is conducive to the formation of inclusion compounds in aqueous solution as well as in the solid state. The physico-chemical study of these complexes was carried out by various analytical techniques such as ultraviolet (UV), Fourier transform infrared (FT-IR), Raman, X-ray diffraction, and 1H-NMR (nuclear magnetic resonance) spectroscopies. The existence of inclusion complexes in water solution between the beta-cyclodextrin and each of the herbicides was revealed by electronic absorption and 1H-NMR spectroscopies. A 1:1 stoichiometry was determined for both complexes in aqueous medium from UV absorption spectra by using the Benesi-Hildebrand method; the relative stability constants at room temperature were calculated at 2700 +/- 300 L mol(-1) and 750 +/- 50 L mol(-1) for isoproturon and diuron, respectively. In the solid state, inclusion processes with beta-cyclodextrin were characterized by means of infrared and Raman techniques and confirmed by X-ray diffraction spectra.

Topics: beta-Cyclodextrins; Cyclodextrins; Diuron; Herbicides; Methylurea Compounds; Phenylurea Compounds; Solutions; Spectrophotometry; Stochastic Processes; Water; X-Ray Diffraction

The inclusion complexes of beta-cyclodextrin-isoproturon were prepared using techniques such as kneading, co-evaporation, and co-precipitation. These complexes were characterised for physical properties and spectral studies such as UV, FTIR, and 1HNMR spectroscopy. To investigate the stoichiometry of the complexes Phase solubility method was adopted. Most of the complexes showed an increase in the dissolution rate of the herbicide. The best results were obtained when inclusion complexes were prepared by co-precipitation and co-evaporation method. Findings of this paper will allow the rational use of isoproturon with increase in its efficacy.

Topics: beta-Cyclodextrins; Carcinogens; Cyclodextrins; Herbicides; Magnetic Resonance Spectroscopy; Methylurea Compounds; Phenylurea Compounds; Solubility; Spectroscopy, Fourier Transform Infrared