Photochemistry of imidacloprid in model systems

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 17, 2008, Pages 8023-8029

  Schippers, Nicole ^a   Schwack, Wolfgang ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

Bound residues; Imidacloprid; Photodegradation

Indexed keywords

CUTINE; EPOXIDE; IMIDACLOPRID; IMIDAZOLE DERIVATIVE; INSECTICIDE; MEMBRANE LIPID; NITRO DERIVATIVE; SOLVENT;

ARTICLE; CHEMISTRY; LIGHT; PHOTOCHEMISTRY;

EPOXY COMPOUNDS; IMIDAZOLES; INSECTICIDES; LIGHT; MEMBRANE LIPIDS; NITRO COMPOUNDS; PHOTOCHEMISTRY; SOLVENTS;

EID: 52649143214     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf801251u     Document Type: Article

References (29)

1. Casida, J. E.; Quistad, G. B. Why insecticides are more toxic to insects than people: the unique toxicology of insects. J. Pestic. Sci. 2004, 29, 81-86.
2. Imidacloprid. In The Pesticide Manual, Incorporating the Agrochemical Handbook, 10th ed.; Tomlin, C., Ed.; British Crop Protection Council: Hampshire, U.K., 1994; pp 591-593.
3. Wamhoff, H.; Schneider, V. Photodegradation of imidacloprid. J. Agric Food Chem. 1999, 47, 1730-1734.
4. Moza, P. N.; Justert, K.; Feicht, E.; Kettrup, A. Photolysis of imidacloprid in aqueous solution. Chemosphere 1997, 36, 497-502.
5. Aguera, A.; Almansa, E.; Malato, S.; Maldonado, M. I.; Fernandez-Alba, A. R. Evaluation of photocatalytic degradation of imidacloprid in industrial water by GC-MS and LC-MS. Analusis 1998, 26, 245-251.
6. Kole, R. K.; Banerjee, H.; Bhattacharyya, A.; Chowdhury, A.; Adityachaudhury, N. Phototransformation of some pesticides. J. Indian Chem. Soc. 1999, 76, 595-600.
7. Imidacloprid. In Metabolic Pathways of Agrochemicals, Part 2: Insecticides and Fungicides; Roberts, T. R., Hutson, D. H., Eds.; The Royal Society of Chemistry Information Services: Cambridge, U.K., 1999; pp 111-120.
8. Schmidt, B. Non-extractable residues of pesticides and xenobiotics in plants - a review. Recent Res. Dev. Agric. Food Chem. 1999, 3, 329-354.
9. Pesticide Residues in Food - Evaluations 2002, Joint FAO/WHO Meeting on Pesticide Residues; World Health Organisation, Food and Agriculture Organization of the United Nations: Geneva, Switzerland, 2002; Vol. 2, pp 687-1007.
10. Scholz, K.; Reinhard, F. Photolysis of imidacloprid (NTN 33893) on the leaf surface of tomato plants. Pestic. Sci. 1999, 55, 652-654.
11. Schwack, W. Photoreduction of parathion-ethyl. Toxicol. Environ. Chem. 1987, 14, 63-72.
12. Schwack, W.; Walker, F.; Bourgeois, B. Fungicides and photochemistry: photodegradation of the dicarboximide fungicide vinclozolin. J. Agric. Food Chem. 1995, 43, 3088-3092.
13. Sinderhauf, K.; Schwack, W. Photolysis experiments on phosmet, an organophosphorus insecticide. J. Agric. Food Chem. 2003, 51, 5990-5995.
14. Kolattukudy, P. E. Polyesters in higher plants. Adv. Biochem. Eng. Biotechnol. 2001, 71, 1-49.
15. Schynowski, F.; Schwack, W. Photochemistry of parathion on plant surfaces: relationship between photodecomposition and iodine number of the plant cuticle. Chemosphere 1996, 33, 2255-2262.
16. Wettach, J. W.; Rung, B.; Schwack, W. Detection of photochemically induced cuticle-bound residues of parathion by immunoassay. Food Agric. Immunol. 2002, 14, 5-13.
17. Rung, B.; Schwack, W. Aminoparathion: a highly reactive metabolite of parathion. 1. Reactions with polyphenols and polyphenol oxidase. J. Agric. Food Chem. 2005, 53, 9140-9145.
18. Kagabu, S.; Yokoyama, K.; Iwaya, K.; Tanaka, M. Chloronicotinyl insecticides. Part X. Imidacloprid and related compounds: structure and water solubility of N-alkyl derivatives of imidacloprid. Biosci. Biotechnol. Biochem. 1998, 62, 1216-1224.
19. Hayakawa, T.; Fujiwara, Y.; Noguchi, J. A new method of reducing nitroarginine-peptide into arginine-peptide, with reference to the synthesis of poly(L-arginine hydrochloride). Bull. Chem. Soc. Jpn. 1967, 40, 1205-1208.
20. Rouchaud, J.; Gustin, F.; Wauters, A. Imidacloprid insecticide soil metabolism in sugar beet field corps. Bull. Environ. Contam. Toxicol. 1996, 56, 29-36.
21. Schwack, W. Photoinduzierte additionen von pesticiden an biomoleküle, III. Modellreaktionen von folpet mit cyclohexen. Z. Lebensm. - Unters. Forsch. 1990, 190, 420-424.
22. Zheng, W.; Liu, W. Kinetics and mechanism of the hydrolysis of imidacloprid. Pestic. Sci. 1999, 55, 482-485.
23. Ohkura, K.; Seki, K.; Terashima, M.; Kanaoka, Y. Direct photolysis of halopyridines in solutions; generation of the 2-pyridyl cation. Chem. Pharm. Bull. 1991, 39, 3168-3169.
24. Bertlett, B. S.; Levine, R. L.; Stadtman, E. R. Use of isosbestic point wavelength shifts to estimate the fraction of a precursor that is converted to a given product. Anal. Biochem. 2000, 287, 329-333.
25. Chow, Y. L.; Richard, H.; Snyder, R. W.; Lockhart, R. W. Generation of aminyl and aminium radicals by photolysis of N-nitrodialkylamines in solution. Can. J. Chem. 1979, 57, 2936-2943.
26. Michejda, C. J.; Rydstrom, T. Photochemistry of N-nitrosamines in neutral media. IARC Sci. Publ. 1984, 57, 365-369.
27. Swern, D.; Findley, T. W. Chemistry of epoxy compounds. XIV. Reaction of cis-9,10-epoxystearic acid with ammonia and amines. J. Am. Chem. Soc. 1952, 74, 6139-6141.
28. Rung, B. Bildung und Analytik gebundener Rückstände des Insektizids Parathion in pflanzlichen Lebensmitteln. Ph.D. Thesis, University of Hohenheim, Stuttgart, Germany, 2003.
29. Robinson, M. W. C.; Timms, D. A.; Williams, S. M.; Graham, A. E. A mild and efficient synthesis of β-amino alcohols from epoxides using a mesoporous aluminosilicate catalyst. Tetrahedron Lett. 2007, 48, 6249-6251.