Cationic micellar-catalyzed hydrolysis of pesticide fenitrothion using α-nucleophiles

Letters in Drug Design and Discovery

Volumn 7, Issue 3, 2010, Pages 194-199

  Tiwari, Shuchi ^a   Ghosh, Kallol K ^a   Marek, Jan ^b   Kuca, Kamil ^b  

^a PT RAVISHANKAR SHUKLA UNIVERSITY   (India)

^b UNIVERSITY OF DEFENCE   (Czech Republic)

Author keywords

Cationic surfactant; Fenitrothion; Hydrolysis, nucleophiles

Indexed keywords

ALPHA NUCLEOPHILE; BENZOHYDROXAMIC ACID; BUTANE 2,3 DIONE MONOXIME; CATIONIC SURFACTANT; FENITROTHION; FUNCTIONAL GROUP; NUCLEOPHILE; PESTICIDE; PRALIDOXIME; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEGRADATION; HYDROLYSIS; HYDROPHOBICITY; PH; PRIORITY JOURNAL; SPECTROPHOTOMETRY;

EID: 77949733060     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018010790596650     Document Type: Article

References (33)

1. Smith, B.M. Catalytic methods for the destruction of chemical warfare agents under ambient conditions. Chem. Soc. Rev., 2008, 37, 470-478.
2. Malosse, L.; Buvat, P.; Ades, D.; Siove, A. Detection of degradation products of chemical warfare agents by highly porous molecularly imprinted microspheres. Analyst, 2008, 133, 588-595.
3. Antonijevic, B.; Stojiljkovic, M.P. Unequal efficacy of pyridinium oximes in acute organophosphate poisoning. Clin. Med. Res., 2007, 5, 71-82.
4. Worek, F.; Thiermann, H.; Szinic, L.; Eyer P. Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes. Biochem. Pharm., 2004, 68, 2237-2248.
5. Desloges, W.; Neverov, A.A.; Brown, R.S. Zinc catalyzed methanolysis of phosphate trimesters: a process for catalytic degradation of the organophosphorus pesticides Paraoxon and Fenitrothion. Inorg. Chem., 2004, 43, 6752-6761.
6. Juan, D.; Xiangguang, M.; Wei, H.; Xiancheng Z. Phosphate monoester cleavage with dinuclear zinc(II) an copper(II) macrocyclic complexes in micellar solution. J. Dispers. Sci. Technol., 2007, 28, 199-206.
7. Couderc, S.; Toullec, J. Catalysis of phosphate triester hydrolysis by micelles of hexadecyltrimethylammonium anti-pyruvaldehyde 1-oximate. Langmuir, 2001, 17, 3819-3828.
8. Hu, C.C.; Chen, W.H.; Liu, C.Y.; Chen, J.L. Hydrolysis of phosphate esters with polymer-supported catalysts containing cyclodextrin pendant group. J. Inclusion Phenom. Macrocycl. Chem., 1996, 23, 289-303.
9. Verschueren, K. Handbook of Environmental Data on Organic Chemicals; Van Nostrand Reinhold: New York, 1996.
10. José, F.; Pilar, H.; Josefa, L.; Alberto, G.; Alfredo, L.; Pilar, F. Dissipation rates of fenitrothion in greenhouse grown lettuce and under cold storage conditions. Int. J. Food Sci. Tech. 2009, 44, 1034-1040.
11. Han, X.; Balakrishnan, V.K.; Buncel, E. Kinetics of decompositition of organophosphate Fenitrothion by decontaminating foammaking blends. Langmuir, 2007, 23, 6519-6525.
12. Han, X.; Balakrishnan, V.K.; VanLoon, G.W.; Buncel, E. Degradation of the pesticide fenitrothion as mediated by cationic surfactants and α-nucleophilic reagents. Langmuir, 2006, 22, 9009-9017.
13. Balakrishnan, V.K.; Buncel, E.; VanLoon, G.W. Micellar catalyzed degradation of fenitrothion, an organophosphorus pesticide, in solution and soils. Environ. Sci. Technol., 2005, 39, 5824-5830.
14. Vico, R.V.; Buján, E.I.; de Rossi, R.H. Effect of cyclodextrin on the hydrolysis of the pesticide fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate. J. Phys. Org. Chem., 2002, 15, 858-862.
15. Cabal, J.; Kuca, K.; Micova J. Kinetics of decompositition of organophosphate fenitrothion by decontaminating foam-making blends. J. Appl. Biomed., 2007, 5, 167-170.
16. Chanda, A.; Khetan, S.K.; Banerjee, D.; Ghosh, A.; Collins, T.J. Total degradation of fenitrothion and other organophosphorus pesticides by catalytic oxidation employing Fe-TAML peroxide activators. J. Am. Chem. Soc., 2006, 128, 12058-12059.
17. Tiwari, S.; Kolay, S.; Ghosh, K.K.; Kuca, K.; Marek, J. Kinetic study of the reactions of p-nitrophenyl acetate and p-nitrophenyl benzoate with oximate nucleophiles. Int. J. Chem. Kinet., 2009, 41, 57-64.
18. Tiwari, S.; Ghosh, K.K.; Marek, J.; Kuca, K. Functionalized surfactant mediated reactions of carboxylate, phosphate and sulphonate esters. J. Phys. Org. Chem., 2010, DOI:10.1002/poc.1635.
19. Tiwari, S.; Ghosh, K.K.; Marek, J.; Kuca, K. Comparative study of nucleophilic efficacy of pralidoxime towards phosphorus, sulfur and thiophosphorus based esters. React. Kinet. Catal. Lett., 2009, 98, 91-97.
20. Tiwari, S.; Ghosh, K.K.; Marek, J.; Kuca, K. Spectrophotometric determination of the acidity constants of some oxime-based α-nucleophiles. J. Chem. Eng. Data, 2009, DOI:10.1021/je9005773.
21. Ghosh, K.K.; Bal, S.; Kolay, S.; Shrivastava, A. Comparative nucleophilic reactivities in carboxylate, phosphate and thiophosphate esters cleavage. J. Phys. Org. Chem., 2008, 21, 492-497.
22. Ghosh, K.K.; Satnami, M.L.; Sinha, D. Dephosphorylation of paraoxon by hydroxamate ions in micellar media. Tetrahedron Lett., 2004, 45, 9103-9105.
23. Ghosh, K.K.; Sinha, D.; Satnami, M.L. Enhanced nucleophilic reactivity of hydroxamate in some novel micellar systems for the cleavage of parathion. J. Colloid Interface Sci., 2006, 301, 564-568.
24. Ghosh, K.K.; Sinha, D.; Satnami, M.L.; Dubey, D.; Dafonte, P.R.; Mundhara, G.L. Nucleophilic dephosphorylation of p-nitrophenyl diphenyl phosphate in cationic micellar media. Langmuir, 2005, 21, 8664-8669.
25. Ghosh, K.K.; Vaidya, J.; Satnami, M.L. The α-effect in micelles: Nucleophilic substitution reaction of p-nitrophenyl acetate with Nphenylbenzohydroxamate ion. Int. J. Chem. Kinet., 2006, 38, 26-31.
26. Tee, O.S.; Fedortchenko, A.A. Transition state stabilization by micelles: the hydrolysis p-nitrophenyl alkanoates in cetyltrimethylammonium bromide micelles. Can. J. Chem., 1997, 75, 1434-1438.
27. Ghosh, K.K.; Kolay, S.; Satnami, M.L.; Moore, S.; Palepu, R.M. Kinetics of reaction of oximate α-nucleophiles with p-nitrophenyl acetate in alkyltriphenylphosphonium bromide micelles. J. Dispers. Sci. Technol., 2007, 28, 213-218.
28. Eddleston, M.; Szinicz, L.; Eyer, P.; Buckley, N. Oximes in acute organophosphorus pesticide poisoning: a systematic review of clinical trials. Q. J. Med., 2002, 95, 275-283.
29. Um, I.H.; Kim, E.H.; Lee, J.Y. Kinetic studies on nucleophilic substitution reactions of O-aryl thionobenzoates with azide, cynide, and hydroxide: Contrasting reactivity and mechanism. J. Org. Chem., 2009, 74, 1212-1217.
30. Um, I.H.; Shin, Y.H.; Han, J.Y.; Buncel, E. Medium effects on the α-effect in DMSO-H2O mixtures: Comparative studies of pnitrophenyl benzoate and acetate. Dissection of ground-state and transition-state. Can. J. Chem., 2006, 84, 1550-1556.
31. Buncel, E.; Um, I.H. The α-effect and its modulation by solvent. Tetrahedron, 2004, 60, 7801-7825.
32. Bunton, C.A.; Gillitt, N.D.; Foroudian, H.J. A quantitative treatment of dephosphorylation by an amphiphilic hydroxamate ion. The role of micellar charge. Langmuir, 1998, 14, 4415-4421.
33. Bunton, C.A., Blasko, A.; Gillitt, N.D. Micellar and solvent effects on the geometrical isomerism of hydroxamic acids and their anions. Langmuir, 1997, 13, 6439-6446.