Abiotic reduction reactions of dichloroacetamide safeners: Transformations of "inert" agrochemical constituents

Environmental Science and Technology

Volumn 46, Issue 4, 2012, Pages 2187-2195

  Sivey, John D ^a   Roberts, A Lynn ^a  

^a Johns Hopkins University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABIOTIC REDUCTION; ACTIVE INGREDIENTS; HERBICIDE FORMULATION; HETEROGENEOUS SYSTEMS; HOMOGENEOUS SYSTEM; LINEAR FREE ENERGY RELATIONSHIPS; MOLECULAR PARAMETERS; NEAR-NEUTRAL PH; NEUTRAL COMPOUNDS; ORDERS OF MAGNITUDE; PRODUCT FORMATION; REDUCTANTS; REDUCTION RATE; REDUCTIVE TRANSFORMATIONS; SAFENERS; STRUCTURAL ANALOGUE; TOXIC EFFECT;

ADSORPTION; CHLORINE; CHLORINE COMPOUNDS; HYDROGEN; HYDROGENOLYSIS; HYDROLYSIS; IRON ORES; REACTION RATES; WEED CONTROL;

HERBICIDES;

ACETAMIDE DERIVATIVE; AGRICULTURAL CHEMICAL; CHLORINE; CHROMIUM DERIVATIVE; DICHLOROACETAMIDE SAFENER; FERRIC HYDROXIDE; FERRIC OXIDE; FERROUS ION; HERBICIDE; HYDROGEN; UNCLASSIFIED DRUG;

ADSORPTION; AGROCHEMICAL; HEMATITE; HERBICIDE; HETEROGENEITY; PH; REACTION RATE; REDUCTION; TOXICITY; TRANSFORMATION;

ADSORPTION; ARTICLE; CHEMICAL STRUCTURE; ENERGY; HYDROGENOLYSIS; REACTION TIME; REDUCTION;

ACETAMIDES; FERRIC COMPOUNDS; HERBICIDES; IRON; IRON COMPOUNDS; KINETICS; MINERALS; OXIDATION-REDUCTION;

EID: 84857694525     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es203755h     Document Type: Article

References (40)

1. Rosinger, C.; Kocher, H. Safeners for herbicides. In Modern Crop Protection Compounds; Kramer, W., Schirmer, U., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 259-281.
2. Miaullis, J. B.; Thomas, V. M.; Gray, R. A.; Murphy, J. J.; Hollingworth, R. M. Metabolism of R-25788 (N,N-diallyl-2,2-dichloroacetamide in corn plants, rats and soil. In Chemistry and Action of Herbicide Antidotes; Pallos, F. M., Casida, J. E., Eds.; Academic Press: New York, 1978; pp 109-131.
3. Hatzios, K. K. Herbicide Antidotes: Development, Chemistry, and Mode of Action. In Advances in Agronomy; Brady, N. C., Ed.; Academic Press: New York, 1983; pp 265-316.
4. Abu-Qare, A. W.; Duncan, F. J. Photodegradation of the herbicide EPTC and the safener dichlormid, alone and in combination. Chemosphere 2002, 46, 1183-1189. (Pubitemid 34188645)
5. Abu-Qare, A. W.; Duncan, H. J. Herbicide safeners: Uses, limitations, metabolism, and mechanisms of action. Chemosphere 2002, 48, 965-974. (Pubitemid 34857466)
6. Lucini, L.; Molinari, G. P. Residues of the herbicide fenoxaprop-P-ethyl, its agronomic safener isoxadifen-ethyl and their metabolites in rice after field application. Pest Manage. Sci. 2010, 66, 621-626.
7. Chnirheb, A.; Harir, M.; Kanawati, B.; Fekete, A.; Azzouzi, M. E.; Hertkorn, N.; Schmitt-Kopplin, P. Hydrolysis of mefenpyrdiethyl: An analytical and DFT investigation. Anal. Bioanal. Chem. 2010, 398, 2325-2334.
8. Worthing, C. R.; Walker, S. B. The Pesticide Manual, 8th ed.; The British Crop Protection Council: Thornton Heath, U.K., 1987; p 1081.
9. Mueller, T. C.; Shaw, D. R.; Witt, W. W. Relative dissipation of acetochlor, alachlor, metolachlor, and SAN 582 from three surface soils. Weed Technol. 1999, 13, 341-346. (Pubitemid 29388473)
10. Pesticide Management Education Program, Cornell University. http://pmep.cce.cornell.edu/(accessed October 18, 2010).
11. Hoadland, R. E.; Zablotowicz, R. M.; Locke, M. A. An integrated phytoremediation strategy for chloroacetamide herbicides in soil. In Phytoremediation of Soil and Water Contaminants; Kruger, E., Anderson, T. A., Coats, J. R., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1997; pp 92-105. (Pubitemid 127438760)
12. Aga, D. S.; Thurman, E. M.; Yockel, M. E.; Zimmerman, L. R.; Williams, T. D. Identification of a new sulfonic acid metabolite of metolachlor in soil. Environ. Sci. Technol. 1996, 30, 592-597.
13. Hladik, M. L.; Hsiao, J. J.; Roberts, A. L. Are neutral chloroacetamide herbicide degradates "emerging contaminants" of potential concern? Analysis and occurrence in the upper Chesapeake Bay. Environ. Sci. Technol. 2005, 39, 6561-6574. (Pubitemid 41266138)
14. Kolpin, D. W.; Barbash, J. E.; Gilliom, R. J. Occurrence of pesticides in shallow groundwater of the United States: Initial results from the National Water-Quality Assessment Program. Environ. Sci. Technol. 1998, 32, 558-566. (Pubitemid 28225121)
15. Coupe, R. H.; Blomquist, J. D. Water-soluble pesticides in finished water of community water supplies. J. AWWA 2004, 96, 56-68.
16. Scarponi, L.; Perucci, P.; Martinetti, L. Conjugation of 2-chloroacetanilide herbicides with glutathione: Role of molecular structures and of glutathione S-transferase enzymes. J. Agric. Food Chem. 1991, 39, 2010-2013.
17. Feng, P. C. C. Soil transformation of acetochlor via glutathione conjugation. Pestic. Biochem. Physiol. 1991, 40, 136-142.
18. II in aqueous suspensions of iron (hydr)oxides. Environ. Sci. Technol. 2002, 36, 1734-1741. (Pubitemid 34310941)
19. II and oxime carbamate pesticides. Geochim. Cosmochim. Acta 2003, 67, 2775-2791. (Pubitemid 36965317)
20. II in aqueous mineral suspensions. Environ. Sci. Technol. 1995, 29, 2396-2404.
21. Mohatt, J. L.; Hu, L.; Finneran, K. T.; Strathmann, T. J. Microbially mediated abiotic transformation of the antimicrobial agent sulfamethoxazole under iron-reducing conditions. Environ. Sci. Technol. 2011, 45, 4793-4801.
22. Rügge, K.; Hofstetter, T. B.; Haderlein, S. B.; Bjerg, P. L.; Knudsen, S.; Zraunig, C.; Mosbak, H.; Christensen, T. H. Characterization of predominant reductants in an anaerobic leachatecontaminated aquifer by nitroaromatic probe compounds. Environ. Sci. Technol. 1998, 32, 23-31. (Pubitemid 28035897)
23. Fogler, H. S. Elements of Chemical Reaction Engineering; Prentice Hall: Upper Saddle River, NJ, 2006; p 1080.
24. Arnold, W. A.; Roberts, A. L. Pathways and kinetics of chlorinated ethylene and chlorinated acetylene reaction with Fe(0) particles. Environ. Sci. Technol. 2000, 34, 1794-1805. (Pubitemid 30246857)
25. II species associated with clay minerals. Environ. Sci. Technol. 2003, 37, 519-528. (Pubitemid 36159641)
26. Kohn, T.; Arnold, W. A.; Roberts, A. L. Reactivity of substituted benzotrichlorides toward granular iron, Cr(II), and an iron(II) porphyrin: A correlation analysis. Environ. Sci. Technol. 2006, 40, 4253-4260. (Pubitemid 44161681)
27. Su, Y. H.; Zhu, Y. G.; Sheng, G.; Chiou, C. T. Linear adsorption of nonionic organic compounds from water onto hydrophilic minerals: Silica and alumina. Environ. Sci. Technol. 2006, 40, 6949-6954. (Pubitemid 44772843)
28. Keiluweit, M.; Kleber, M. Molecular-level interactions in soils and sediments: The role of aromatic p-systems. Environ. Sci. Technol. 2009, 43, 3421-3429.
29. Abraham, M. H.; Andonian-Haftan, J.; Whiting, S.; Leo, A.; Taft, R. S. Hydrogen bonding, Part 34. The factors that influence the solubility of gases and vapors in water at 298 K, and a new method for its determination. J. Chem. Soc., Perkin Trans. 1994, 2, 1777-1791.
30. Schwertmann, U. Some properties of soil and synthetic iron (hydr)oxides. In Iron in Soils and Clay Minerals; NATO ASI Series C; Stucki, J. W., Goodman, B. A., Schwertmann, U., Eds.; Kluwer: Norwell, MA, 1988; Vol. 217, pp 203-260.
31. Stookey, L. L. Ferrozine-A new spectrophotometric reagent for iron. Anal. Chem. 1970, 42, 779-781.
32. Curran, D. P.; Tamine, J. Effects of temperature on atom transfer cyclization reactions of allylic a-iodo esters and amides. J. Org. Chem. 1991, 56, 2746-2750.
33. Klupinski, T. P.; Chin, Y.-P. Abiotic degradation of trifluralin by Fe(II): Kinetics and transformation pathways. Environ. Sci. Technol. 2003, 37, 1311-1318. (Pubitemid 36504945)
34. Liger, E.; Charlet, L.; Van Cappellen, P. Surface catalysis of uranium(VI reduction by iron(II). Geochim. Cosmochim. Acta 1999, 63, 2939-2955. (Pubitemid 30106828)
35. Buchholz, A.; Laskov, C.; Haderlein, S. B. Effects of zwitterionic buffers on sorption of ferrous iron at goethite and its oxidation by CCl4. Environ. Sci. Technol. 2011, 45, 3355-3360.
36. Zwank, L.; Elsner, M.; Aeberhard, A.; Schwarzenbach, R. P.; Haderlein, S. B. Carbon isotope fractionation in the reductive dehalogenation of carbon tetrachloride at iron (hydr)oxide and iron sulfide minerals. Environ. Sci. Technol. 2005, 39, 5634-5641.
37. Abraham, M. H.; McGowan, J. C. The use of characteristic volumes to measure cavity terms in reversed phase liquid chromatography. Chromatographia 1987, 25, 243-246.
38. Hamm, P. C. Discovery, development, and current status of the chloroacetamide herbicides. Weed Sci. 1974, 22, 541-545.
39. Jablonkai, I. Alkylating reactivity and herbicidal activity of chloroacetamides. Pest Manage. Sci. 2003, 59, 443-450. (Pubitemid 36402286)
40. Klaassen, C. D.; Watkins, J. B., III, Eds. Casarett & Doull's Essentials of Toxicology; McGraw-Hill: New York, 2003; p 533.