Metabolism of fungicide diethofencarb in grape (Vitis vinifera L.): Definitive identification of thiolactic acid conjugated metabolites

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 18, 2003, Pages 5329-5336

  Fujisawa, Takuo ^a   Ichise Shibuya, Keiko ^a   Katagi, Toshiyuki ^a   Ruzo, Luis O ^b   Takimoto, Yoshiyuki ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

^b PTRL West Inc   (United States)

Author keywords

Conjugate; Diethofencarb; Metabolism; Thiolactic acid; Vitis vinifera L.

Indexed keywords

ACETONITRILE; DIETHOFENCARB; FUNGICIDE; GLUCOSE DERIVATIVE; HYDROXYL GROUP; ISOPROPYL 3 ETHOXY 4 HYDROXYCARBANILATE; LACTIC ACID; PHENOL DERIVATIVE; PHENYL GROUP; THIOLACTIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; FRUIT; GRAPE; GREENHOUSE; HARVEST; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; PLANT GROWTH; PLANT LEAF; PROTON NUCLEAR MAGNETIC RESONANCE;

CARBAMATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUIT; FUNGICIDES, INDUSTRIAL; MAGNETIC RESONANCE SPECTROSCOPY; PHENYLCARBAMATES; PLANT LEAVES; SULFHYDRYL COMPOUNDS; VITIS;

VITIS; VITIS SP.; VITIS VINIFERA;

EID: 0042513824     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf034367+     Document Type: Article

References (36)

1. Takahashi, J.; Nakamura, S.; Noguchi, H.; Kato, T.; Kamoshita, K. Fungicidal activity of N-phenylcarbamate against benzimidazole resistant fungi. J. Pestic. Sci. 1988, 13, 63-69.
2. Takahashi, J.; Kirino, O.; Takayama, C.; Nakamura, S.; Noguchi, H.; Kato, T.; Kamoshita, K. Quantitative structure - activity relationships of fungicidal N-(3,4-diethoxyphenyl)carbamates. J. Pestic. Sci. 1988, 13, 587-593.
3. Takahashi, J.; Kirino, O.; Takayama, C.; Nakamura, S.; Noguchi, H.; Kato, T.; Kamoshita, K. Quantitative structure- activity relationships of the fungicidal methyl N-phenylcarbamate. Pestic. Biochem. Physiol. 1988, 30, 262-271.
4. James, C. S.; Prendeville, G. N. Metabolism of chlorpropham (isopropyl m-chlorocarbanilate) in various plant species. J. Agric. Food Chem. 1969, 17, 1257-1260.
5. Still, G. G.; Mansager, E. R. Metabolism of isopropyl 3-chlorocarbanilate by soybean plants. J. Agric. Food Chem. 1971, 19, 879-884.
6. Still, G. G.; Mansager, E. R. Aryl hydroxylation of isopropyl-3-chlorocarbanilate by soybean plants. Phytochemistry 1972, 11, 515-520.
7. Still, G. G.; Mansager, E. R. Soybean shoot metabolism of isopropyl-3-chlorocarbanilate: Ortho and para aryl hydroxylation. Pestic. Biochem. Physiol. 1973, 3, 87-95.
8. Still, G. G.; Mansager, E. R. Metabolism of isopropyl-3-chlorocarbanilate by cucumber plants. J. Agric. Food Chem. 1973, 21, 787-791.
9. Still, G. G.; Rusness, D. G. S-cysteinyl-hydroxychlorpropham: Formation of the S-cysteinyl conjugate of isopropyl-3′-chloro-4′-hydroxycarbanilate in oat (Avena sativa L.). Pestic. Biochem. Physiol. 1977, 7, 210-219.
10. Heikes, D. L. Mass spectral identification of a metabolite of chlorpropham in potatoes. J. Agric. Food Chem. 1985, 33, 246-249.
11. Still, G. G.; Mansager, E. R. Metabolism of isopropyl carbanilate by soybean plants. Pestic. Biochem. Physiol. 1973, 3, 289-299.
12. Still, G. G.; Mansager, E. R. Alfalfa metabolism of propham. Pestic. Biochem. Physiol. 1975, 5, 515-522.
13. Zurqiyah, A. A.; Jordan, L. S.; Jolliffe, V. A. Metabolism of isopropyl carbanilate (propham) in alfalfa grown in nutrient solution. Pestic. Biochem. Physiol. 1976, 6, 35-45.
14. Castello, A.; Marquet, J.; Moreno-Manas, M.; Sirera, X. The nucleophilic aromatic photosubstitution in photoaffinity labeling. A model study of a cycloheximide derivative. Tetrahedron Lett. 1985, 26, 2489-2492.
15. Schmidt, R. R.; Zimmermann, P. Synthesis of glycosphingolipids and psychosines. Angew. Chem., Int. Ed. Engl. 1986, 25, 725-726.
16. Hattori, K.; Takido, T.; Itabashi, K. The synthesis of thiols by use of N,N-dimethylthioformamide. Nippon Kagaku Kaishi 1979, 101-105.
17. Fernando, R. C.; Calder, I. C.; Ham, K. N. Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2,6-dimethyl- and N-acetyl-3,5-dimethyl-p-benzoquinone imines. J. Med. Chem. 1980, 23, 1153-1158.
18. Lee, H. H.; Palmer, B. D.; Denny, W. A. Reactivity of quinone imine and quinone diimine metabolites of the antitumor drug amsacrine and related compounds to nucleophiles. J. Org. Chem. 1988, 53, 6042-6047.
19. Lamoureux, G. L.; Gouot, J. M.; Davis, D. G.; Rusness, D. G. Pentachloronitrobenzene metabolism in peanut. 3. Metabolism in peanut cell suspension cultures. J. Agric. Food Chem. 1981, 29, 996-1002.
20. Lamoureux, G. L.; Rusness, D. G. EPTC metabolism in corn, cotton, and soybean: Identification of a novel metabolite derived from the metabolism of a glutathione conjugate. J. Agric. Food Chem. 1987, 35, 1-7.
21. Lamoureux, G. L.; Rusness, D. G. Propachlor metabolism in soybean plants, excised soybean tissues, and soil. Pestic. Biochem. Physiol. 1989, 34, 187-204.
22. Lamoureux, G. L.; Rusness, D. G.; Schröder, P.; Rennenberg, H. Diphenyl ether herbicide metabolism in a spruce cell suspension culture: The identification of two novel metabolites derived from a glutathione conjugate. Pestic. Biochem. Physiol. 1991, 36, 291-301.
23. Hinson, J. A.; Monks, T. J.; Hong, M.; Highet, R. J.; Pohl, L. R. 3-(Glutathion-S-yl)acetaminophen: a biliary metabolite of acetaminophen. Drug Metab. Dispos. 1982, 10, 47-50.
24. Morgan, E. T.; Koop, D. R.; Coon, M. J. Comparison of six rabbit liver cytochrome P-450 isozymes in formation of a reactive metabolite of acetaminophen. Biochem. Biophys. Res. Commun. 1983, 112, 8-13.
25. Albano, E.; Rundgren, M.; Harvison, P. J.; Nelson, S. D.; Moldéus, P. Mechanism of N-acetyl-p-benzoquinone imine cytotoxicity. Mol. Pharmacol. 1985, 28, 306-311.
26. Potter, D. W.; Miller, D. W.; Hinson, J. A. Horseradish peroxidase-catalyzed oxidation of acetaminophen to intermediates that form polymers or conjugate with glutathione. Mol. Pharmacol. 1986, 29, 155-162.
27. Potter, D. W.; Hinson, J. A. Reactions of N-acetyl-p-benzoquinone imine with reduced glutathione, acetaminophen, and NADPH. Mol. Pharmacol. 1986, 30, 33-41.
28. Potter, D. W.; Hinson, J. A. Mechanisms of acetaminophen oxidation to N-acetyl-p-benzoquinone imine by horseradish peroxidase and cytochrom P-450. J. Biol. Chem. 1987, 262, 966-973.
29. Potter, D. W.; Hinson, J. A. The 1- and 2-electron oxidation of acetaminophen catalyzed by prostaglandin H synthase. J. Biol. Chem. 1987, 262, 974-980.
30. Finley, T. K.; Tong, J. L. K. Quinonediimine and related compounds. In The Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Interscience Publishers, London, 1970; pp 663-729.
31. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AMI: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
32. Gemborys, M. W.; Gribble, G. W.; Mudge, G. H. Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate. J. Med. Chem. 1978, 21, 649-652.
33. Miner, D. J.; Kissinger, P. T. Evidence for involvement of N-acetyl-p-quinoneimine in acetaminophen metabolism. Biochem. Pharmacol. 1979, 28, 3285-3290.
34. Buckpitt, A. R.; Rollins, D. E.; Nelson, S. D.; Franklin, R. B.; Mitchell, J. R. Quantitative determination of the glutathione, cycteine, and N-acetyl cysteine conjugates of acetaminophen by high-pressure liquid chromatography. Anal. Biochem. 1977, 83, 168-177.
35. Pascoe, G. A.; Calleman, C. J.; Baille, T. A. Identification of S-(2,5-dihydroxyphenyl)-cysteine and S-(2,5-dihydroxyphenyl)-N-acetyl-cysteine as urinary metabolites of acetaminophen in the mouse. Evidence for p-benzoquinone as a reactive intermediate in acetaminophen metabolism. Chem.-Biol. Intract. 1988, 68, 85-98.
36. Park, S. K.; Boulton, R. B.; Noble, A. C. Automated HPLC analysis of glutathione and thiol-containing compounds in grape juice and wine using pre-column derivatization with fluorescence detection. Food Chem. 2000, 68, 475-480.