Kinetics and mechanism of propachlor reductive transformation through nucleophilic substitution by dithionite

Chemosphere

Volumn 85, Issue 9, 2011, Pages 1438-1443

  Liu, C S ^a,b   Shih, K ^a   Wei, L ^b   Wang, F ^a   Li, F B ^b  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b GUANGDONG INSTITUTE OF ECO ENVIRONMENTAL AND SOIL SCIENCES   (China)

Author keywords

Chloroacetanilide herbicides; Dechlorination; Nucleophilic reagent; Nucleophilic substitution; Second order kinetics

Indexed keywords

GROUNDWATER; GROUNDWATER POLLUTION; GROUNDWATER RESOURCES; HERBICIDES; KINETICS; RATE CONSTANTS; SULFUR COMPOUNDS; WEED CONTROL;

CHLOROACETANILIDE HERBICIDES; DECHLORINATION PRODUCTS; NON-POINT CONTAMINATION; NUCLEOPHILIC REAGENT; NUCLEOPHILIC SUBSTITUTIONS; REDUCTIVE DECHLORINATION; REDUCTIVE TRANSFORMATIONS; SECOND ORDER KINETICS;

DECHLORINATION;

DITHIONITE; ESYLIC ACID; HYDROXYL PROPACHLOR; NUCLEOPHILE; PROPACHLOR; SULFUR; UNCLASSIFIED DRUG;

BIOREMEDIATION; DECHLORINATION; GROUNDWATER POLLUTION; HERBICIDE; MOLECULAR ANALYSIS; NONPOINT SOURCE POLLUTION; ORGANIC ACID; PH; REACTION KINETICS; SOIL POLLUTION; TEMPERATURE EFFECT; TRANSFORMATION; WEED CONTROL;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DECHLORINATION; EXCITATION; IONIZATION; NUCLEOPHILICITY; PH; REDUCTION; REDUCTION KINETICS; SUBSTITUTION REACTION; TEMPERATURE;

EID: 82455210778     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2011.08.023     Document Type: Article

References (29)

1. Bian H., Chen J., Cai X., Liu P., Wang Y., Huang L., Qiao X., Hao C. Dechlorination of chloroacetanilide herbicides by plant growth regulator sodium bisulfite. Water Res. 2009, 43:3566-3574.
2. Boparai H.K., Comfort S.D., Shea P.J., Szecsody J.E. Remediation explosive-contaminated groundwater by in situ redox manipulation (ISRM) of aquifer sediments. Chemosphere 2008, 71:933-941.
3. Boparai H.K., Shea P.J., Comfort S.D., Snow D.D. Dechlorinating chloroacetanilide herbicides by dithionite-treated aquifer sediment and surface soil. Environ. Sci. Technol. 2006, 40:3043-3049.
4. Cai X., Sheng G., Liu W. Degradation and detoxification of acetochlor in soils treated by organic and thiosulfate amendments. Chemosphere 2007, 66:286-292.
5. Carlson D.L., Than K.D., Roberts A.L. Acid- and base-catalyzed hydrolysis of chloroacetamide herbicides. J. Agric. Food Chem. 2006, 54:4740-4750.
6. Cavalier T.C., Lavy T.L., Mattice J.D. Persistence of selected pesticides in ground-water samples. Ground Water 1991, 29:225-231.
7. Comfort S.D., Shea P.J., Machacek T.A., Gaber H., Oh B.T. Field-scale remediation of a metolachlor-contaminated spill site using zerovalent iron. J. Environ. Qual. 2001, 30:1636-1643.
8. Dagnac T., Jeannot R., Mouvet C., Baran N. Determination of oxanilic and sulfonic acid metabolites of acetochlor in soils by liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr. A 2002, 957:69-77.
9. Fife T.H., Bembi R. Metal ion promoted hydroxide ion and water catalyzed hydrolysis of amides. Effects of the acyl group and the leaving group. J. Am. Chem. Soc. 1993, 115:11358-11363.
10. Gan J.Y., Wang Q.Q., Yates S.R., Koskinen W.C., Jury W.A. Dechlorination of chloroacetanilide herbicides by thiosulfate salts. Proc. Natl. Acad. Sci. USA 2002, 99:5189-5194.
11. Geoffroy N., Demopoulos G.P. Reductive precipitation of elemental selenium from selenious acidic solutions using sodium dithionite. Ind. Eng. Chem. Res. 2009, 48:10240-10246.
12. Goerke J., de Gier J., Bonsen P.P.M. Silica gel stimulates the hydrolysis of lecithin by phospholiphase A. Biochim. Biophys. Acta 1971, 248:245-253.
13. Huang C.H., Stone A.T. Hydrolysis of naptalam and structurally related amides: inhibition by dissolved metal ions and metal (hydro)oxide surfaces. J. Agric. Food. Chem. 1999, 47:4425-4434.
14. Kolpin D.W., Barbash J.E., Gilliom R.J. Pesticides in ground water of the United States, 1992-1996. Ground Water 2000, 38:858-863.
15. Kolpin D.W., Thurman E.M., Goolsby D.A. Occurrence of selected pesticides and their metabolites in near-surface aquifers of the Midwestern United States. Environ. Sci. Technol. 1996, 30:335-340.
16. Kumari N., Narayan O.P., Rai L.C. Understanding butachlor toxicity in Aulosira fertilissima using physiological, biochemical and proteomic approaches. Chemosphere 2009, 77:1501-1507.
17. Lippa K.A., Roberts A.L. Nucleophilic aromatic substitution reactions of chloroazines with bisulfide (HS-) and polysulfides (Sn2-). Environ. Sci. Technol. 2002, 36:2008-2018.
18. Liu W.P., Gan J.Y., Papiernik S.K., Yates S.R. Sorption and catalytic hydrolysis of diethatyl-ethyl on homoionic clays. J. Agric. Food Chem. 2000, 48:1935-1940.
19. Loch A.R., Lippa K.A., Carlson D.L., Chin Y.P., Traina S.J., Roberts A.L. Nucleophilic aliphatic substitution reactions of propachlor, alachlor, and metolachlor with bisulfide (HS-) and polysulfide (Sn2-). Environ. Sci. Technol. 2002, 36:4065-4073.
20. Moran E.E., Timerghazin Q.K., Kwong E., English A.M. Kinetics and mechanism of S-nitrosothiol acid-catalyzed hydrolysis: sulfur activation promotes facile NO+ release. J. Phys. Chem. B 2011, 115:3112-3126.
21. Nzengung V.A., Castillo R.M., Gates W.P., Mills G.L. Abiotic transformation of perchloroethylene in homogeneous dithionite solution and in suspensions of dithionite-treated clay minerals. Environ. Sci. Technol. 2001, 35:2244-2251.
22. Osano O., Nzyuko D., Tole M., Admiraal W. The fate of chloroacetanilide herbicides and their degradation products in the Nzoia Basin, Kenya. Ambio 2003, 32:424-427.
23. Scheunert I., Parlar H. Terrestrial Behavior of Pesticides 1992, Springer-Verlag, New York.
24. Sharma K.K. Degradation of alachlor in water and tropical soils of India. Bull. Environ. Contam. Toxicol. 2002, 68:394-399.
25. Su C., Ludwig R.D. Treatment of hexavalent chromium in chromite ore processing solid waste using a mixed reductant solution of ferrous sulfate and sodium dithionite. Environ. Sci. Technol. 2005, 39:6208-6216.
26. Xie Y., Cwiertny D.M. Use of dithionite to extend the reactive lifetime of nanoscale zero-valent iron treatment systems. Environ. Sci. Technol. 2010, 44:8649-8655.
27. Zheng H.H., Ye C.L. Identification of UV photoproducts and hydrolysis products of butachlor by mass spectrometry. Environ. Sci. Technol. 2001, 35:2889-2895.
28. Zheng W., Gan J., Papiernik S.K., Yates S.R. Identification of volatile/semivolatile products derived from chemical remediation of cis-1,3-dichloropropene by thiosulfate. Environ. Sci. Technol. 2007, 41:6454-6459.
29. Zheng W., Yates S.R., Papiernik S.L., Guo M.X. Transformation of herbicide propachlor by an agrochemical thiourea. Environ. Sci. Technol. 2004, 38:6855-6860.