Photodegradation of fenitrothion and parathion in tomato epicuticular waxes

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 2, 2006, Pages 474-479

  Fukushima, Masao ^a   Katagi, Toshiyuki ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

Epicuticular wax; Fenitrothion; Parathion; Photodegradation

Indexed keywords

FENITROTHION; INSECTICIDE; PARATHION; WAX;

ARTICLE; CHEMISTRY; INFRARED SPECTROSCOPY; KINETICS; LIGHT; PHOTOLYSIS; TOMATO; ULTRAVIOLET SPECTROPHOTOMETRY;

FENITROTHION; INSECTICIDES; KINETICS; LIGHT; LYCOPERSICON ESCULENTUM; PARATHION; PHOTOLYSIS; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; WAXES;

LYCOPERSICON ESCULENTUM;

EID: 33644540786     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf052113d     Document Type: Article

References (28)

1. Walton, T. J. Waxes, Cutin and Suberin, Methods in Plant Biochemistry, Vol.4; Academic Press: New York, 1990; Chapter 5.
2. Katagi, T. Photodegradation of pesticides on plant and soil surfaces. Rev. Environ. Contam. Toxicol. 2004, 182, 1-195.
3. Schwack, W.; Andlauer, W.; Armbruster, W. Photochemistry of parathion in the plant cuticle environment: Model reactions in the presence of 2-propanol and methyl 12-hydroxystearate. Pestic. Sci. 1994, 40, 279-284.
4. Schynowski, F.; Schwack, W. Photochemistry of parathion on plant surfaces: Relationship between photodecomposition and iodine number of plant cuticle. Chemosphere 1996, 33, 2255-2262.
5. Silva, J.; Ferreira, L.; Silva, A.; Oliveira, A. Photochemistry of 4-chlorophenol on cellulose and silica. Environ. Sci. Technol. 2003, 37, 4798-4803.
6. Peacock, G. A.; Riches, M. N.; Wood, S. A new method for the evaluation of the photostability of crop protection compounds; the prediction of photostability in the field. BCPC Monogr. 1994, 59, 251-256.
7. Pirisi, F.; Angioni, A.; Cabizza, M.; Cabras, P.; Maccioni, E. Influence of epicuticular waxes on the photolysis of pirimicarb in the solid phase. J. Agric. Food Chem. 1998, 46, 762-765.
8. Angioni, A.; Cabizza, M.; Cabras, M.; Melis, M.; Tuberoso, C.; Cabras, P. Effect of the epicuticular waxes of fruits and vegetables on the photodegradation of rotenone. J. Agric. Food Chem. 2004, 52, 3451-3455.
9. Cabras, P.; Angioni, A.; Garau, V.; Melis, M.; Pirisi, F.; Minelli, E. Effect of epicuticular waxes of fruits on the photodegradation of fenthion. J. Agric. Food Chem. 1997, 45, 3681-3683.
10. Schöenherr, J.; Riederer, M. Plant cuticles sorb lipophilic compounds during enzymatic isolation. Plant Cell Environ. 1986, 9, 459-466.
11. Ohkawa, H.; Mikami, N.; Miyamoto, J. Photodecomposition of sumithion [O,O-dimethyl-O-(3-methyl-4-nitrophenyl)-phosphorothioate]. Agric. Biol. Chem. 1974, 38, 2247-2255.
12. Greenhalgh, R.; Marshall, W. D. Ultraviolet irradiation of fenitrothion and the synthesis of the photolytic oxidation products. J. Agric. Food Chem. 1976, 24, 708-713.
13. Mikami, N.; Imanishi, K.; Yamada, H.; Miyamoto, J. Photodegradation of fenitrothion in water and on soil surface, and its hydrolysis in water. J. Pestic. Sci. 1985, 10, 263-272.
14. Schwack, W. Photoreduction of parathion ethyl. Toxicol. Environ. Chem. 1987, 14, 63-72.
15. Miyamoto, J.; Kitagawa, K.; Sato, Y. Metabolism of organophosphorus insecticides by Bacillus subtilis, with special emphasis on sumithion. Jpn. J. Exp. Med. 1966, 36, 211-225.
16. Ahmed, M. K.; Casida, J. E.; Nichols, R. E. Bovine metabolism of organophosphorus insecticides: Significance of rumen fluid with particular reference to parathion. J. Agric. Food Chem. 1958, 6, 740-746.
17. Yoshitake, A.; Kawahara, K.; Kodama, T.; Endo, M. Labeled organophosphorus pesticides. I. Synthesis of carbon-14 labeled O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate (sumithion). J. Labelled Compd. Radiopharm. 1976, 13, 323-331.
18. Growth stages of mono-and dicotyledonous. Plants BBCH Monograph, 2nd ed.; Meier, U., Ed.; Federal Biological Research Centre for Agriculture and Forestry: Berlin, Germany, 2001.
19. McDonald, R.; Nordby, H.; McCollum, T. Epicuticular wax morphology and composition are related to grapefruit chilling injury. HortScience 1993, 28, 311-312.
20. Katagi, T. Photoinduced oxidation of the organophosphorus fungicide tolclofos-methyl on clay minerals. J. Agric. Food Chem. 1990, 38, 1595-1600.
21. Baker, E. A. Chemistry and morphology of plant epicuticular waxes. Linn. Soc. Symp. Ser. 1982, 10, 139-165.
22. Frank, M.; Graebing, P.; Chib, J. Effect of soil moisture and sample depth on pesticide photolysis. J. Agric. Food Chem. 2002, 50, 2607-2614.
23. Katagi, T. Ab initio structure of trimethyl- and dimethylphenylphosphorothioates. J. Mol. Struct. 1990, 209, 61-67.
24. Stewart, J. J. P. WINMOPAC Program; Fujitsu Ltd.: Tokyo, Japan, 2001.
25. Pople, J. Approximate self-consistent molecular-orbital theory. V. Intermediate neglect of differential overlap. J. Chem. Phys. 1967, 47, 2026-2033.
26. Chen, Z.; Zablk, M. Leavltt, comparative study of thin film photodegradative rates for 36 pesticides. Ind. Eng. Chem. Prod. Res. Dev. 1984, 23, 5-11.
27. Fukushima, M.; Fujisawa, T.; Katagi, T.; Takimoto, Y. Metabolism of fenitrothion and conjugation of 3-methyl-4-nitrophenol in tomato plant (Lycopersicon esculentum). J. Agric. Food Chem. 2003, 51, 5016-5023.
28. Margulies, L.; Stern, T.; Rubin, B.; Ruzo, L. Photostabilization of trifluralin adsorbed on a clay matrix. J. Agric. Food Chem. 1992, 40, 152-155.