Cyclodextrin inclusion complex to improve physicochemical properties of herbicide bentazon: Exploring better formulations

PLoS ONE

Volumn 7, Issue 8, 2012, Pages

  Yáñez, Claudia ^a   Cañete Rosales, Paulina ^a   Castillo, Juan Pablo ^a   Catalán, Nicole ^a   Undabeytia, Tomás ^b   Morillo, Esmeralda ^b  

^a UNIVERSITY OF CHILE   (Chile)

^b INSTITUTO DE RECURSOS NATURALES Y AGROBIOLOGÍA DE SEVILLA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; BENTAZON; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN SULFOBUTYL ETHER;

ARTICLE; COMPLEX FORMATION; DIFFERENTIAL PULSE VOLTAMMETRY; DIFFERENTIAL SCANNING CALORIMETRY; FREEZE DRYING; INFRARED SPECTROSCOPY; PHYSICAL CHEMISTRY; STOICHIOMETRY; SURFACE TENSION; X RAY DIFFRACTION;

BENZOTHIADIAZINES; CHEMISTRY, PHARMACEUTICAL; CHEMISTRY, PHYSICAL; CYCLODEXTRINS; DRUG DESIGN; ELECTROCHEMISTRY; HERBICIDES; KINETICS; MODELS, CHEMICAL; OLIGOSACCHARIDES; PESTICIDES; PHOTOCHEMISTRY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SURFACE PROPERTIES; X-RAY DIFFRACTION;

EID: 84865431379     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0041072     Document Type: Article

References (42)

1. Szejtli J, (1998) Introduction and General Overview of Cyclodextrin Chemistry. Chemical Reviews 98: 1743-1754.
2. Misiuk W, Zalewska M, (2009) Investigation of inclusion complex of trazodone hydrochloride with hydroxypropyl-β-cyclodextrin. Carbohydrate Polymers 77: 482-488.
3. Kawasaki N, Araki M, Nakamura T, Tanada S, (2001) Inclusion Behavior of 4-Nonylphenol into Cyclodextrin Derivatives. Journal of Colloid and Interface Science 238: 215-218.
4. Loftsson T, Brewster ME, (1996) Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. Journal of Pharmaceutical Sciences 85: 1017-1025.
5. Szejtli J, (2004) Past, present and futute of cyclodextrin research. Pure and Applied Chemistry 76: 1825-1845.
6. Dodziuk H (2006) Cyclodextrins and Their Complexes: Chemistry, Analytical Methods, Applications: John Wiley & Sons.
7. Pérez-Martínez JI, Morillo E, Ginés JM, (1999) β-CD effect on 2,4-D soil adsorption. Chemosphere 39: 2047-2056.
8. Villaverde J, Morillo E, Pérez-Martínez JI, Ginés JM, Maqueda C, (2004) Preparation and Characterization of Inclusion Complex of Norflurazon and β-Cyclodextrin To Improve Herbicide Formulations. Journal of Agricultural and Food Chemistry 52: 864-869.
9. Villaverde J, Pérez-Martínez JI, Maqueda C, Ginés JM, Morillo E, (2005) Inclusion complexes of α- and γ-cyclodextrins and the herbicide norflurazon: I. Preparation and characterisation. II. Enhanced solubilisation and removal from soils. Chemosphere 60: 656-664.
10. Villaverde J, (2007) Time-dependent sorption of norflurazon in four different soils: Use of β-cyclodextrin solutions for remediation of pesticide-contaminated soils. Journal of Hazardous materials 142: 184-190.
11. Ribeiro AB, Mateus EP, Rodríguez-Maroto J-M, (2011) Removal of organic contaminants from soils by an electrokinetic process: The case of molinate and bentazone. Experimental and modeling. Separation and Purification Technology 79: 193-203.
12. Pourata R, Khataee AR, Aber S, Daneshvar N, (2009) Removal of the herbicide Bentazon from contaminated water in the presence of synthesized nanocrystalline TiO2 powders under irradiation of UV-C light. Desalination 249: 301-307.
13. International Program on Chemical S, International Labour O, World Health O, United Nations Environment P (1990) Bentazone health and safety guide. Geneva: World Health Organization.
14. Galhano V, Peixoto F, Gomes-Laranjo J, Fernández-Valiente E, (2010) Comparative toxicity of bentazon and molinate on growth, photosynthetic pigments, photosynthesis, and respiration of the Portuguese ricefield cyanobacterium Nostoc muscorum. Environmental Toxicology 25: 147-156.
15. Agency USEP (1985) Chemical fact sheet for bentazon and sodium bentazon. Fact sheet no. 64. In: Programs OoP, editor. Washington, DC.
16. Al-Khatib K, Kadir S, Libbey C, (1995) Effect of Adjuvants on Bentazon Efficacy in Green Pea (Pisum sativum. Weed Technology 9: 426-431.
17. Ge X, He J, Qi F, Yang Y, Huang Z, et al. (2011) Inclusion complexation of chloropropham with β-cyclodextrin: Preparation, characterization and molecular modeling. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 81: 397-403.
18. Mount D (2005) Insecticide-impregnated fabric and method of production. 6,896,892.
19. Yañez C, Araya M, Bollo S, (2010) Complexation of herbicide bentazon with native and modified β-cyclodextrin. Journal of Inclusion Phenomena and Macrocyclic Chemistry 68: 237-241.
20. Del Valle EMM, (2004) Cyclodextrins and their uses: a review. Process Biochemistry 39: 1033-1046.
21. Hashimoto H, (2002) Present Status of Industrial Application of Cyclodextrins in Japan. Journal of Inclusion Phenomena and Macrocyclic Chemistry 44: 57-62.
22. Morillo E (2006) Application of Cyclodextrins in Agrochemistry. In: Dodziuk H, editor. Cyclodextrins and Their Complexes: Chemistry, Analytical Methods, Applications: John Wiley & Sons. pp. 459-467.
23. Porini JA, Escandar GM, (2011) Spectrofluorimetric study of the herbicide bentazone in organized media: analytical applications. Analytical Methods 3: 1494-1500.
24. Yáñez C, Núñez-Vergara LJ, Squella JA, (2003) Differential Pulse Polarographic and UV-Vis Spectrophotometric Study of Inclusion Complexes Formed by 1,4-Dihydropyridine Calcium Antagonists, Nifedipine and Nicardipine with β-Cyclodextrin. Electroanalysis 15: 1771-1777.
25. Carrizosa MJ, Koskinen WC, del Carmen Hermosín M, (2004) Interactions of acidic herbicides bentazon and dicamba with organoclays. Soil Science Society of America Journal 68: 1863-1866.
26. De Araújo MVG, Vieira EKB, Lázaro GS, de Souza Conegero L, Ferreira OP, et al. (2007) Inclusion complexes of pyrimethamine in 2-hydroxypropyl-β-cyclodextrin: Characterization, phase solubility and molecular modelling. Bioorganic & Medicinal Chemistry 15: 5752-5759.
27. Mayo DW, Miller FA, Hannah RW (2004) Course notes on the interpretation of infrared and Raman spectra: Wiley-Interscience.
28. Food and Agriculture Organization Of The United Nations F (1999).Specifications and Evaluations For Plant Protection Products: BENTAZONE. Available: http://www.fao.org/agriculture/crops/core-themes/theme/pests/pm/jmps/ps/ps-new/en/#B. Accessed: 11 May 2012.
29. Peschka M, Petrovic M, Knepper T, Barceló D, (2007) Determination of two phototransformation products of bentazone using quadrupole time-of-flight mass spectrometry. Analytical and Bioanalytical Chemistry 388: 1227-1234.
30. Davezza M, Fabbri D, Pramauro E, Bianco Prevot A, (2012) Photocatalytic degradation of bentazone in soil washing wastes containing alkylpolyoxyethylene surfactants. Chemosphere 86: 335-340.
31. Zeng Q, Liao B, Luo Y, Liu C, Tang H, (2003) Inclusion Effects of Highly Water-Soluble Cyclodextrins on the Solubility, Photodegradation, and Acute Toxicity of Methyl Parathion. Bulletin of Environmental Contamination and Toxicology 71: 0668-0674.
32. Villaverde J, Maqueda C, Undabeytia T, Morillo E, (2007) Effect of various cyclodextrins on photodegradation of a hydrophobic herbicide in aqueous suspensions of different soil colloidal components. Chemosphere 69: 575-584.
33. Kamiya M, Nakamura K, (1995) Cyclodextrin inclusion effects on photodegradation rates of organophosphorus pesticides. Environment International 21: 299-304.
34. Hanna K, de Brauer C, Germain P, Chovelon JM, Ferronato C, (2004) Degradation of pentachlorophenol in cyclodextrin extraction effluent using a photocatalytic process. Science of the Total Environment 332: 51-60.
35. Orgoványi J, Otta KH, Pöppl L, Fenyvesi É, Záray G, (2005) Spectrophotometric and thermoanalytical study of cypermethrin/cyclodextrin complexes. Microchemical Journal 79: 77-82.
36. Dua K, Ramana MV, Singh Sara UV, Himaja M, Agrawal A, et al. (2007) Investigation of Enhancement of Solubility of Norfloxacin-Cyclodextrin in Presence of Acidic Solubilizing Additives. Current Drug Delivery 4: 21-25.
37. Leclercq L, Bricout H, Tilloy S, Monflier E, (2007) Biphasic aqueous organometallic catalysis promoted by cyclodextrins: Can surface tension measurements explain the efficiency of chemically modified cyclodextrins? Journal of Colloid and Interface Science 307: 481-487.
38. Nogueiras-Nieto L, Alvarez-Lorenzo C, Sandez-Macho I, Concheiro A, Otero-Espinar FJ, (2009) Hydrosoluble Cyclodextrin/Poloxamer Polypseudorotaxanes at the Air/Water Interface, in Bulk Solution, and in the Gel State. The Journal of Physical Chemistry B 113: 2773-2782.
39. Yañez C, Basualdo J, Jara-Ulloa P, Squella JA, (2007) Inclusion complexes of estrone and estradiol with β-cyclodextrin: Voltammetric and HPLC studies. Journal of Physical Organic Chemistry 20: 499-505.
40. Ibrahim MS, Shehatta IS, Al-Nayeli AA, (2002) Voltammetric studies of the interaction of lumazine with cyclodextrins and DNA. Journal of Pharmaceutical and Biomedical Analysis 28: 217-225.
41. Ureta-Zañartu MS, Yáñez C, Gutiérrez C, (2004) Cyclic voltammetric, EQCM and impedance study of the 1-octanol-β-cyclodextrin-electrodeposited platinum system in perchloric medium. Journal of Electroanalytical Chemistry 569: 275-286.
42. Job P, (1928) Formation and stability of inorganic complexes in solution. Annali di Chimica Applicata 9: 113-203.