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In Vitro Production of Superoxide Radical from Paraquat and Its Interactions by Monuron and Diuron

Published online by Cambridge University Press:  12 June 2017

G.N. Giannopolitis  and
S.K. Ries
G.N. Giannopolitis
Affiliation:
Dep. Hortic., Pesticide Res. Center, Michigan State Univ., E. Lansing, MI 48824
S.K. Ries
Affiliation:
Dep. Hortic., Pesticide Res. Center, Michigan State Univ., E. Lansing, MI 48824
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Abstract

The abilities of herbicides to either produce superoxide radical or react with this radical were examined. The effect of the herbicides on the superoxide-induced reduction of p-nitro blue tetrazolium chloride was used as an index. Paraquat (1,1-dimethyl-4,4′-bipyridinium ion) enhanced and diuron [3-(3,4-dichlorophenyl)-1,1-dimethylurea] inhibited the reduction of p-nitro blue tetrazolium chloride. Paraquat was reduced photochemically (riboflavin/methionine) or enzymatically (xanthine/xanthine oxidase) and produced superoxide radical upon reoxidation. Diuron and monuron [3-(p-chlorophenyl)-1,1-dimethylurea] interacted with photochemically produced superoxide radical, but not with enzymatically produced superoxide radical. The product of the monuron/superoxide interaction was a demethylated, dechlorinated, water-soluble compound containing phenolic hydroxyl group(s), and was not toxic to oats (Avena sativa L.). The enzyme superoxide dismutase prevented the formation of this product.

Type
Research Article
Information
Weed Science , Volume 25 , Issue 4 , July 1977 , pp. 298 - 303
Copyright
Copyright © 1977 by the Weed Science Society of America 

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References

Literature Cited

1. Asada, K. and Kiso, K. 1973. The photooxidation of epinephrine by spinach chloroplasts and its inhibition by superoxide dismutase: evidence for the formation of superoxide radicals in chloroplasts. Agric. Biol. Chem. 37:453–454.Google Scholar
2. Aust, S.D., Roering, D.L., and Pederson, T.C. 1972. Evidence for superoxide generation by NADPH-cytochrome c reductase of rat liver microsomes. Biochem. Biophys. Res. Commun. 46:1133–1137.CrossRefGoogle Scholar
3. Autor, A.P. 1974. Reduction of paraquat toxicity by superoxide dismutase. Life Sci. 14:1309–1319.Google Scholar
4. Babior, B.M., Kipnes, R.S., and Curnutte, J.T. 1973. The production by leucocytes of superoxide: a potential bactericidal agent. J. Clin. Invest. 52:741–744.Google Scholar
5. Beauchamp, C. and Fridovich, I. 1971. Superoxide dismutase: improved assays and an assay applicable to acrylamide gels. Anal. Biochem. 44:276–287.CrossRefGoogle Scholar
6. Black, C.C. Jr. and Myers, L. 1966. Some biochemical aspects of the mechanisms of herbicidal activity. Weeds 14:331–338.CrossRefGoogle Scholar
7. Farrington, J.A., Ebert, M., Land, E.J., and Fletcher, K. 1973. Bipyridylium quaternary salts and related compounds. V. Pulse radiolysis studies of the reaction of paraquat radical with oxygen. Implications for the mode of action of bipyridyl herbicides. Biochim. Biophys. Acta 314:372–381.CrossRefGoogle ScholarPubMed
8. Fridovich, I. 1974. Superoxide dismutases. Adv. Enzymol. 41:35–97.Google Scholar
9. Gregory, E.M. and Fridovich, I. 1973. Oxygen toxicity and the superoxide dismutase. J. Bacteriol. 114:1193–1197.Google Scholar
10. Halliwell, B. 1974. Superoxide dismutase, catalase and glutathione peroxidase: solutions to the problems of living with oxygen. New Phytol. 73:1075–1086.Google Scholar
11. Homann, P. and Gaffron, H. 1963. Flavin sensitized photoreactions effects of 3-(p-chlorophenyl)-1,1-dimethylurea. Science 141:905–907.CrossRefGoogle ScholarPubMed
12. Kok, B., Rurainski, H.J., and Owens, O.V.H. 1965. The reducing power generated in photoact I of photosynthesis. Biochim. Biophys. Acta 109:347–356.CrossRefGoogle ScholarPubMed
13. Massey, V., Strickland, S., Mayhew, S.G., Howell, L.G., Engel, P.C., Matthews, R.G., Schuman, M., and Sullivan, P.A. 1969. The production of superoxide anion radicals in the reaction of reduced flavins and flavoproteins with molecular oxygen. Biochem. Biophys. Res. Commun. 36:891–897.CrossRefGoogle ScholarPubMed
14. McCord, J.M. and Fridovich, I. 1969. Superoxide dismutase: an enzymic function for erythrocuprein (hemocuprein). J. Biol. Chem. 244:6049–6055.Google Scholar
15. Misra, H.P. and Fridovich, I. 1971. The generation of superoxide radical during the autoxidation of ferredoxins. J. Biol. Chem. 246:6886–6890.CrossRefGoogle Scholar
16. Misra, H.P. and Fridovich, I. 1972. The univalent reduction of oxygen by reduced flavins and quinones. J. Biol. Chem. 247:188–192.Google Scholar
17. Nishikimi, M., Rao, N.A., and Yagi, K. 1972. The occurrence of superoxide anion in the reaction of reduced phenzaine methosulfate and molecular oxygen. Biochem. Biophys. Res. Commun. 46:849–854.CrossRefGoogle Scholar
18. Plimmer, J.R., Kearney, P.C., and Klingebiel, U.I. 1971. s-Triazine herbicide dealkylation by free-radical generating systems. J. Agric. Food Chem. 19:572–573.Google Scholar
19. Prema-Kumar, R., Ravindranath, S.D., Vaidyanthan, C.S., and Appaji Rao, N. 1972. Mechanism of hydroxylation or aromatic compounds: II. Evidence for the involvement of superoxide anions in enzymatic hydroxylations. Biochem. Biophys Res Commun. 49:1422–1426.Google Scholar
20. Prema, K. and Gopinathan, K.P. 1974. Involvement of the superoxide anion in sulfoxidation. Biochem. J. 137:119–121.CrossRefGoogle Scholar
21. Stancliffe, T.C. and Pirie, A. 1971. The production of superoxide radicals in reactions of the herbicide diquat. FEBS Lett 17:297–299.Google Scholar
22. Sweetser, P.B. 1963. Photoinactivation of monuron, 3-(p-chlorophenyl)-1,1-dimethylurea, by riboflavin 5′-phosphate. Biochim. Biophys. Acta 66:78–85.Google Scholar
23. White, J.R., Vaughan, T.O., and Yeh, W.S. 1971. Superoxide radical in the mechanism of action of streptonigrin. Fed. Proc. Fed. Am. Soc. Exp. Biol. 30:1145 (Abstr.) Google Scholar
24. Zweig, G., Shavit, N., and Avron, M. 1965. Diquat (1,1′-ethylene-2,2′-dipyridylium dibromide) in photoreactions of isolated chloroplasts. Biochim. Biophys. Acta 109:332–346.CrossRefGoogle Scholar