Enantiomeric discrimination and quantification of the chiral organophosphorus pesticide fenamiphos in aqueous samples by a novel and selective 31P nuclear magnetic resonance spectroscopic method using cyclodextrins as chiral selector

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 3, 2011, Pages 803-808

  Molaabasi, Fatemeh ^a   Talebpour, Zahra ^a  

^a ALZAHRA UNIVERSITY   (Iran)

Author keywords

31P nuclear magnetic resonance; Cyclodextrins; Enantiomeric discrimination; Organophosphorus pesticide

Indexed keywords

31P NUCLEAR MAGNETIC RESONANCE; AQUEOUS SAMPLES; AQUEOUS SOLUTIONS; CALIBRATION CURVES; CARBOXYMETHYL; CDS; CHIRAL RECOGNITION; CHIRAL SELECTOR; CHIRAL SOLVATING AGENTS; COEFFICIENTS OF VARIATIONS; DISPLACEMENT VALUE; ENANTIOMERIC DISCRIMINATION; FENAMIPHOS; INCLUSION COMPLEX; LIMITS OF DETECTION; MOLAR RATIO; NUCLEAR OVERHAUSER SPECTROSCOPY; ORGANOPHOSPHORUS PESTICIDE; REAL SAMPLES; ROTATING FRAME; SPECTROSCOPIC METHOD; TWO-DIMENSION;

CHIRALITY; CYCLODEXTRINS; ENANTIOMERS; PESTICIDES; RESONANCE; SPECTROSCOPIC ANALYSIS;

NUCLEAR MAGNETIC RESONANCE;

CYCLODEXTRIN; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FENAMIPHOS; ORGANOPHOSPHORUS COMPOUND; WATER;

ARTICLE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REPRODUCIBILITY; SOLUTION AND SOLUBILITY; STEREOISOMERISM;

CYCLODEXTRINS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOPHOSPHORUS COMPOUNDS; REPRODUCIBILITY OF RESULTS; SOLUTIONS; STEREOISOMERISM; WATER;

EID: 79851505712     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf103169p     Document Type: Article

References (31)

1. Kurihara, N.; Miyamoto, J.; Paulson, G. D.; Zeeh, B.; Skidmore, M. W.; Hollingworth, R. M.; Kuiper, H. A. Chirality in synthetic agrochemicals: bioactivity and safety consideration. Pure Appl. Chem. 1997, 69, 2007-2025.
2. Battershill, J. M.; Edwards, P. M.; Johnson, M. K. Toxicological assessment of isomeric pesticides: a strategy for testing of chiral organophosphorus (OP) compounds for delayed polyneuropathy in a regulatory setting. Food Chem. Toxicol. 2004, 42, 1279-1285. (Pubitemid 38780875)
3. Ohkawa, H.; Mikami, N.; Miyamoto, J. Stereoselectivity in metabolism of the optical isomers of cyanofenphos (O-p-cyanophenyl O-ethyl phenylphosphonothioate) in rats and liver microsomes. Agric. Biol. Chem. 1977, 41, 369-376. (Pubitemid 8115074)
4. Armstrong, D. J.; Fukuto, T. R. Synthesis, resolution, and toxicological properties of the chiral isomers of O, S-dimethyl and- diethylethylphosphonothioate. J. Agric. Food Chem. 1987, 35, 500-503.
5. Wang, Y. Sh.; Tai, K. Th.; Yen, J. H. Separation, bioactivity, and dissipation of enantiomers of the organophosphorus insecticide fenamiphos. Ecotoxicol. Environ. Saf. 2004, 57, 346-353.
6. Zhang, X.; Xia, T.; Chen, J.; Huang, L.; Cai, X. Direct chiral resolution of metalaxyl and metabolite metalaxyl acid in aged mobile phases: the role of trace water. J. Agric. Food Chem. 2010, 58, 5004-5010.
7. Sinclair, C. J.; Boxall, A. B. A. Assessing the ecotoxicity of pesticide transformation products. Environ. Sci. Technol. 2003, 37, 4617-4625. (Pubitemid 37266378)
8. Fidalgo-Used, N.; Blanco-González, E.; Sanz-Medel, A. Evaluation of two commercial capillary columns for the enantioselective gas chromatographic separation of organophosphorus pesticides. Talanta 2006, 70, 1057-1063. (Pubitemid 44693575)
9. Lin, K.; Zhou, S.; Xu, C.; Liuli, W. Enantiomeric resolution and biotoxicity of methamidophos. J. Agric. Food Chem. 2006, 54, 8134-8138. (Pubitemid 44785395)
10. García-Ruiz, C.; Álvarez-Llamas, G.; Puerta, Á.; Blanco, E.; Sanz-Medel, A.; Marina, M. L. Enantiomeric separation of organophosphorus pesticides by capillary electrophoresis. Application to the determination of malathion in water samples after preconcentration by off-line solid-phase extraction. Anal. Chim. Acta 2005, 543, 77-83. (Pubitemid 40804635)
11. Zhu, W.; Wu, F.; Raushel, F. M.; Vigh, G Capillary electrophoretic separation of the enantiomers of organophosphates with a phosphorus stereogenic center using the sodium salt of octakis (2,3-diacetyl-6-sulfo)-γ- cyclodextrin as resolving agent. J. Chromatogr., A, 2000, 895, 247-254.
12. Buonasera, K.; D'Orazio, G.; Fanali, S.; Dugo, P.; Mondello, L. Separation of organophosphorus pesticides by using nano-liquid chromatography. J. Chromatogr., A 2009, 1216, 3970-3976.
13. Cháfer-Pericás, C.; Herráez-Hernández, R.; Campíns-Falcó, P. Intube solid-phase microextraction-capillary liquid chromatography as a solution for the screening analysis of organophosphorus pesticides in untreated environmental water samples. J. Chromatogr., A 2007, 1141, 10-21. (Pubitemid 46053942)
14. Ellington, J. J.; Evans, J. J.; Prickett, K. B.; Champion, W. L. Highperformance liquid chromatographic separation of the enantiomers of organophosphorus pesticides on polysaccharide chiral stationary phases. J. Chromatogr., A 2001, 928, 145-154. (Pubitemid 32822782)
15. Wang, C.; Zhang, N.; Li, L.; Zhang, Q.; Zhao, M.; Liu, W. Enantioselective interaction with acetylcholinesterase of an organophosphate insecticide fenamiphos. Chirality 2010, 22, 612-617.
16. Tian, Q.; Lv, C.; Ren, L.; Zhou, Z. Direct enantiomeric separation of chiral pesticides by LC on amylosetris (3, 5-dimethylphenylcarbamate) stationary phase under reversed phase conditions. Chromatographia 2010, 71, 855-865.
17. Lecoeur-Lorin, M.; Delepee, R.; Morin, Ph. Simultaneous enantioselective determination of fenamiphos and its two metabolites in soil sample by CE. Electrophoresis 2009, 30, 2931-2939.
18. Wenzel, T. J.; Wilcox, J. D. Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy. Chirality 2003, 15, 256-270. (Pubitemid 36268461)
19. Parker, D. NMR determination of enantiomeric purity. Chem. Rev. 1991, 91, 1441-1457.
20. Zhou, L.; Thompson, R.; Reamer, R. A.; Miller, C.; Welch, Ch.; Ellison, D. K.; Wyvratt, J. M. Mechanistic study of enantiomeric recognition with native γ-cyclodextrin by capillary electrophoresis, reversed-phase liquid chromatography, nuclear magnetic resonance spectroscopy, electrospray mass spectrometry and circular dichroism techniques. J. Chromatogr., A 2003, 987, 409-420. (Pubitemid 36140117)
21. Talebpour, Z.; Ghassempour, A.; Zendehzaban, M.; Bijanzadeh, H. R.; Mirjalili, M. H. Monitoring of the insecticide trichlorfon by phosphorus-31 (P NMR) spectroscopy Nnuclear magnetic resonance. Anal. Chim. Acta 2006, 576, 290-296.
22. 31P NMR spectroscopy in food analysis. Prog. Nucl. Magn. Reson. Spectrosc. 2009, 54, 195-207.
23. *-Chiral phosphapalladacycle as derivatizing agent for enantiomeric purity determination of R-amino acids by means of P NMR spectroscopy. Tetrahedron: Asymmetry 2000, 11, 2907-2916. (Pubitemid 30645719)
24. Holzgrabe, U.; Wawer, I.; Diehl, B. NMR Spectroscopy in Drug Development and Analysis; Wiley: New York, 1999; Chapter 6.
25. Mac Nicol, D. D.; Rycroft, D. S. Cyclodextrins as chiral nuclear magnetic resonance shift reagents. Tetrahedron Lett. 1977, 18, 2173-2176.
26. Berthod, A. Chiral recognition mechanisms. Anal. Chem. 2006, 78, 2093-2099.
27. Berlicki, Ł.; Rudzińska, E.; Kafarski, P. Enantiodifferentiation of aminophosphonic and aminophosphinic acids with α-and β-cyclodextrins. Tetrahedron: Asymmetry 2003, 14, 1535-1539. (Pubitemid 36588853)
28. Holzgrabe, U. Quantitative NMR spectroscopy in pharmaceutical applications. Prog. Nucl. Magn. Spectrosc. 2010, 57, 229-240.
29. Jullian, C.; Orosteguis, T.; Pérez-Cruz, F.; Sánchez, P.; Mendizabal, F.; Olea-Azar, C. Complexation of morin with three kinds of cyclodextrin. A thermodynamic and reactivity study. Spectrochim. Acta Part A 2008, 71, 269-275.
30. Cookson, D. J.; Smith, B. E. Optimal experimental parameters for quantitative pulse Fourier transform proton nuclear magnetic resonance spectrometry. Anal. Chem. 1982, 54, 2591-2593.
31. 19F NMR spectroscopic method for determination of insecticide diflubenzuron in different media. Food Chem. 2007, 105, 1682-1687. (Pubitemid 47103237)