Preparation and Characterization of Inclusion Complex of Norflurazon and β-Cyclodextrin To Improve Herbicide Formulations

Villaverde, Jaime; Morillo, E.; Pérez-Martínez, J. I.; Ginés, J. M.; Maqueda, C.

doi:10.1021/jf0350358

Cited by 58 publications

(46 citation statements)

References 26 publications

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“…It has been recently demonstrated the formation of an inclusion complex between BCD and the herbicide NFL in solid and solution state [12], and in this way this work will mean an extension of the previous paper from a point of view to obtain an efficient in situ soil decontamination tool.…”

Section: Introductionmentioning

confidence: 78%

“…In a previous work [12], the formulation of inclusion complex in solution of the herbicide NFL as guest and BCD as host was studied, and the interaction produced the formation of an inclusion complex in solution state with an apparent stability constant of 360 M −1 , a 1:1 stoichiometric ratio for the complex, and up to five-fold in NFL hydrosolubility.…”

Section: Resultsmentioning

confidence: 99%

“…This property provides CD a capacity to increase the apparent solubility of several hydrophobic pollutants such as PAH, chlorinated solvents, pesticides, and nitroaromatic compounds and thus their bioavailability for biodegradation [9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

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Time-dependent sorption of norflurazon in four different soils: Use of β-cyclodextrin solutions for remediation of pesticide-contaminated soils

Villaverde¹

2007

Journal of Hazardous Materials

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Section: Introductionmentioning

confidence: 78%

Section: Resultsmentioning

confidence: 99%

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Time-dependent sorption of norflurazon in four different soils: Use of β-cyclodextrin solutions for remediation of pesticide-contaminated soils

Villaverde¹

2007

Journal of Hazardous Materials

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“…Complexes obtained in solution are frequently studied by phase-solubility, to obtain the stoichiometric ratio for the complex and an apparent stability constant [12][13][14], but spectral studies including UV, infrared, fluorescence, and NMR spectroscopy (see Section 10.3 and Chapter 9) can also be used for characterization [6,[15][16][17]. Inclusion compounds obtained in the solid state are frequently characterized using infrared spectroscopy, X-ray diffraction (Chapter 7), scanning electron microscopy techniques [18,19] (Section 10.6), differential scanning calorimetry (DSC) (Chapter 8) [20,21], and/or fluorescence (Section 10.3) and voltammetric measurements (Section 10.5) [16,22].…”

mentioning

confidence: 99%

“…Villaverde et al [14,28] have studied the possibility of obtaining inclusion complexes with natural CyDs to obtain formulations that improve the behavior of this herbicide in soils. An increase in norflurazon solubility up to five-fold was obtained with a-and b-CyDs and up to four-fold with g-CyD.…”

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confidence: 99%

Cyclodextrins and Their Complexes

Dodziuk¹

2006

410

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The ability of cyclodextrins, CyDs, to form inclusion complexes with a wide variety of hydrophobic guest molecules has been used in agriculture. Their ability to alter the physical, chemical, and biological properties of guest molecules has been used for the preparation of new formulations of pesticides. CyDs form complexes with a wide variety of agricultural chemicals including herbicides, insecticides, fungicides, repellents, pheromones, and growth regulators [1,2].Each CyD has its own ability to form inclusion complexes with specific pesticides, depending on a proper fit of the pesticide molecule into the hydrophobic CyD cavity. The principal advantage is that the binding of pesticide molecules within the host molecule is not fixed or permanent but rather is a dynamic equilibrium. Dissociation of the inclusion complex is a relatively rapid process usually driven by a large increase in the number of water molecules in the surrounding environment [3]. aAQ16.3.1aSimilarly to CyD applications in the pharmaceutical (Chapters 14 and 15) and other industries, the most common benefits of CyD applications in agriculture include, among others, alterations of the solubility of the pesticide, stabilization against the effects of light or biochemical degradation, and a reduction of volatility. In some applications, more than one benefit is obtained by complexation with CyDs. However, the application of these hosts in pesticide formulations is very modest, and represents less than 1% of the CyD literature [4]. Moreover, most of these publications are not directly practice oriented. Instead they deal with the preparation of pesticides@CyD complexes using different oligosaccharides and processing methods and their characterization using a wide variety of techniques.Among these papers, some are more or less theoretical papers dealing with the correlation between the properties of the new complexes obtained and the properties of the CyDs, pesticides, or external parameters used. Viernstein et al.

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Enantioselective toxicity of metolachlor to scenedesmus obliquus in the presence of cyclodextrins

Liu¹,

Cai²,

Huang³

et al. 2011

Chirality

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Cyclodextrins (CDs) possess a variety of chiral centers and are capable of recognizing enantiomeric molecules through the formation of inclusion complexes. Two types of CDs, α-cyclodextrin (α-CD) and β-cyclodextrin (β-CD), were selected to evaluate the effects of the enantioselective ecotoxicity of racemic metolachlor (Rac-metolachlor) and its S-enantiomer (S-metolachlor) on the freshwater algae Scenedesmus obliquus (S. obliquus) by acute toxicity test. The results showed that the aquatic toxicity of S-metolachlor was higher than Rac-metolachlor and that CDs enhanced the toxicity of metolachlor enantioselectively by increasing the aquatic toxicity of Rac-metolachlor rather than that of S-metolachlor to S. obliquus. The equilibrium constant for Rac-metolachlor-CD complexes was higher than that of S-metolachlor-CDs, which was responsible for the greater aquatic toxicity shift effect of Rac-metolachlor. Thermodynamic studies of CD complexes showed that inclusion for all of the complexes was primarily a spontaneous, enthalpy-driven process. These results will help to understand the preliminary mechanism of shifting aquatic toxicity of metolachlor by CDs and the CDs mediated environmental processes of metolachlor, to correctly apply CDs to chiral pesticides formulation and environmental remediation of chiral contaminants.

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Preparation and Characterization of Inclusion Complex of Norflurazon and β-Cyclodextrin To Improve Herbicide Formulations

Cited by 58 publications

References 26 publications

Time-dependent sorption of norflurazon in four different soils: Use of β-cyclodextrin solutions for remediation of pesticide-contaminated soils

Time-dependent sorption of norflurazon in four different soils: Use of β-cyclodextrin solutions for remediation of pesticide-contaminated soils

Cyclodextrins and Their Complexes

Enantioselective toxicity of metolachlor to scenedesmus obliquus in the presence of cyclodextrins

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