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Oxadiazon Activity is Similar to That of p-Nitro-Diphenyl Ether Herbicides

Published online by Cambridge University Press:  12 June 2017

Stephen O. Duke ,
John Lydon  and
Rex N. Paul
Stephen O. Duke
Affiliation:
USDA, Agric. Res. Serv., South. Weed Sci. Lab., P.O. Box 350, Stoneville, MS 38776
John Lydon
Affiliation:
USDA, Agric. Res. Serv., South. Weed Sci. Lab., P.O. Box 350, Stoneville, MS 38776
Rex N. Paul
Affiliation:
USDA, Agric. Res. Serv., South. Weed Sci. Lab., P.O. Box 350, Stoneville, MS 38776
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Abstract

Oxadiazon (10 μM) caused rapid, light-dependent membrane damage to cucumber cotyledon discs. Electrolyte leakage was detected within 1 h of exposure to light, as were cytoplasmic vesiculation and breakage of the tonoplast and plasmalemma. The ultrastructure of chloroplasts was not affected until the cytoplasm was dispersed. Photosynthetic inhibitors had no effect on activity and, after a period of dark incubation with oxadiazon, there was little effect of temperature on the light-caused membrane destruction. Porphyrin synthesis inhibitors (gabaculine and 4,6-dioxoheptanoic acid) almost completely prevented the herbicidal activity of oxadiazon. Oxadiazon treatment caused accumulation of protoporphyrin IX, a photodynamic pigment. Oxadiazon caused physiological effects on cucumber cotyledons that were virtually identical to those of p-nitro-diphenyl ether herbicides like acifluorfen and its methyl ester, which have recently been shown to also cause protoporphyrin IX accumulation.

Keywords

Acifluorfen, 5 - [2-chloro-4-(trifluoromethyl)phenoxy] −2-nitrobenzoic acidcucumber, Cucumis sativus L.gabaculine, 3-amino 2,3-dihydrobenzoic acidoxadiazon, 3-[2,4-dichloro-5-(1-methylethoxy)phenyl]-5-(1,1-dimethyl)-1,3,4-oxadiazol-2-(3H)-oneChlorophyll synthesislipid peroxidationphotobleachingphotodynamicprotoporphyrin IXultrastructure
Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 37 , Issue 2 , March 1989 , pp. 152 - 160
Copyright
Copyright © 1989 by the Weed Science Society of America 

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References

Literature Cited

1. Arnon, D. I. 1949. Copper enzymes in isolated chloroplasts. Polyphenol oxidases in Beta vulgaris . Plant Physiol. 24:1–15.Google Scholar
2. Böger, P. 1984. Multiple modes of action of diphenyl ethers. Z. Naturforsch. 39C:468–475.Google Scholar
3. Caiger, D. P., Pearson, S. A., Smith, A. J., and Rogers, L. J. 1986. Differential effects of gabaculin and laevulinic acid on protochlorophyllide regeneration. Plant Cell Environ. 9:495–499.Google Scholar
4. Corriveau, J. L. and Beale, S. I. 1986. Influence of gabaculine on growth, chlorophyll synthesis, and δ-aminolevulinic acid synthase activity in Euglena gracilis . Plant Sci. 45:9–17.Google Scholar
5. Devlin, R. M., Karczmarczyk, S. J., and Zbiec, I. I. 1983. Influence of norflurazon on the activation of substituted diphenylether herbicides by light. Weed Sci. 31:109–112.Google Scholar
6. Duggan, J. and Gassman, M. 1974. Induction of porphyrin synthesis in etiolated bean leaves by chelators of iron. Plant Physiol. 53:206–215.Google Scholar
7. Duke, S. O. and Kenyon, W. H. 1986. Photosynthesis is not involved in the mechanism of action of acifluorfen in cucumber (Cucumis sativus L.). Plant Physiol. 81:882–888.Google Scholar
8. Duke, S. O. and Kenyon, W. H. 1986. Effects of dimethazone (FMC 57020) on chloroplast development. II. Pigment synthesis and photosynthetic function in cowpea (Vigna unguiculata L.) primary leaves. Pestic. Biochem. Physiol. 25:11–18.Google Scholar
9. Duke, S. O. and Kenyon, W. H. 1987. A non-metabolic model of acifluorfen activity. Z. Naturforsch. 42C:813–818.Google Scholar
10. Duke, S. O., Vaughn, K. C., and Meeusen, R. L. 1984. Mitochondrial involvement in the mode of action of acifluorfen. Pestic. Biochem. Physiol. 21:368–376.Google Scholar
11. Ensminger, M. P. and Hess, F. D. 1985. Action spectrum of the activity of acifluorfen-methyl, a diphenylether herbicide, in Chlamydomonas eugametos . Plant Physiol. 77:503–505.Google Scholar
12. Fadayomi, O. and Warren, G. F. 1976. The light requirement for herbicidal activity of diphenyl ethers. Weed Sci. 24:598–600.Google Scholar
13. Gaba, V., Cohen, N., Shaaltiel, Y., Ben-Amotz, A., and Gressel, J. 1988. Light-requiring acifluorfen action in the absence of bulk photosynthetic pigments. Pestic. Biochem. Physiol. 31:1–12.Google Scholar
14. Halling, B. P. and Peters, G. R. 1987. Influence of chloroplast development on the activation of the diphenyl ether herbicide acifluorfen-methyl. Plant Physiol. 84:1114–1120.Google Scholar
15. Hatzios, K. K. 1987. Comparative effects of oxadiazon and its metabolites on biochemical processes of enzymatically isolated leaf cells of soybean. Zizaniology 1:235–242.Google Scholar
16. Haworth, P. and Hess, F. D. 1988. The generation of singlet oxygen (1O2) by the nitro-diphenyl ether herbicide oxyfluorfen is independent of photosynthesis. Plant Physiol. 86:672–676.Google Scholar
17. Hill, C. M., Pearson, S. A., Smith, A. J., and Rogers, L. J. 1985. Inhibition of chlorophyll synthesis in Hordeum vulgare by 3-amino 2,3-dihydrobenzoic acid (gabaculin). Biosci. Rep. 5: 775–781.Google Scholar
18. Hiscox, J. D. and Israelstam, G. F. 1979. A method for the extraction of chlorophyll from leaf tissues without maceration. Can. J. Bot. 57:1332–1334.Google Scholar
19. Kannangara, C. and Schouboe, A. 1985. Biosynthesis of α-amino-levulinate in greening barley leaves. VII. Glutamate 1-semialdehyde accumulation in gabaculine treated leaves. Carlsberg Res. Commun. 50:179–191.Google Scholar
20. Kenyon, W. H., Duke, S. O., and Paul, R. N. 1988. Effects of temperature on the activity of the p-nitrosubstituted diphenyl ether herbicide acifluorfen in cucumber (Cucumis sativus L.). Pestic. Biochem. Physiol. 30:57–66.Google Scholar
21. Kenyon, W. H., Duke, S. O., and Vaughn, K. C. 1985. Sequence of herbicidal effects of acifluorfen on ultrastructure and physiology of cucumber cotyledon discs. Pestic. Biochem. Physiol. 24:240–250.Google Scholar
22. Lydon, J. and Duke, S. O. 1988. Porphyrin synthesis is required for photobleaching activity of the p-nitrosubstituted diphenylether herbicides. Pestic. Biochem. Physiol. 31:74–83.Google Scholar
23. Matringe, M. and Scalla, R. 1987. Photoreceptors and respiratory electron flow involvement in the activity of acifluorfen-methyl and LS 82-556 on nonchlorophyllous soybean cells. Pestic. Biochem. Physiol. 27:267–274.Google Scholar
24. Matringe, M. and Scalla, R. 1987. Induction of tetrapyroles by diphenylether-type herbicides. Proc. Br. Crop Prot. Conf. 9B: 981–988.Google Scholar
25. Matringe, M. and Scalla, R. 1988. Studies on the mode of action of acifluorfen-methyl in non-chlorophyllous soybean cells: Accumulation of tetrapyroles. Plant Physiol. 86:619–622.Google Scholar
26. Matsunaka, S. 1969. Acceptor of light energy in photoactivation of diphenylether herbicides. J. Agric. Food Chem. 17:171–175.Google Scholar
27. Meller, E. and Gassman, M. L. 1981. The effects of levulinic acid and 4,6-dioxoheptanoic acid the metabolism of etiolated and greening barley leaves. Plant Physiol. 67:728–732.Google Scholar
28. Orr, G. L. and Hess, F. D. 1981. Characterization of herbicidal injury by acifluorfen-methyl in excised cucumber (Cucumis sativus L.) cotyledons. Pestic. Biochem. Physiol. 16:171–178.Google Scholar
29. Orr, G. L. and Hess, F. D. 1982. Proposed site(s) of action of new diphenyl ether herbicides. Am. Chem. Soc. Symp. Ser. 181:131–152.Google Scholar
30. Rebeiz, C. A., Mattheis, J. R., Smith, B. B., Rebeiz, C. C., and Dayton, D. F. 1975. Chloroplast biogenesis: Biosynthesis and accumulation of protoporphyrin IX monoester and longer wavelength metalloporphyrins by greening cotyledons. Arch. Biochem. Biophys. 166:446–465.Google Scholar
31. Rebeiz, C. A., Montazer-Zouhoor, A., Hopen, H. J., and Wu, S. M. 1984. Photodynamic herbicides: 1. Concept and phenomenology. Enzyme Microb. Technol. 5:390–401.Google Scholar
32. Rebeiz, C. A., Montazer-Zouhoor, A., Mayasich, J. M., Tripathy, B. C., Wu, S. M., and Rebeiz, C. C. 1987. Photodynamic herbicides and chlorophyll biosynthesis modulators. Am. Chem. Soc. Symp. Ser. 339:295–328.Google Scholar
33. Sandmann, G., Reck, H., and Böger, P. 1984. Herbicidal mode of action on chlorophyll formation. J. Agric. Food Chem. 32: 868–872.Google Scholar
34. Sato, R., Nagano, E., Oshio, H., Kamoshita, K., and Furuya, M. 1987. Wavelength effect on the action of a N-phenylimide S-23142 and a diphenylether acifluorfen-ethyl in cotyledons of cucumber (Cucumis sativus L.) seedlings. Plant Physiol. 85: 1146–1150.Google Scholar
35. Suzuki, T., Holden, I., and Casida, J. E. 1981. Diphenyl ether herbicides remarkably elevate the content in Spinacia oleracea of (E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-propenamide. J. Agric. Food Chem. 29:992–995.Google Scholar
36. Tissut, M., Ravanel, P., Nurit, F., Deslandres, C., and Bourguignon, J. 1987. Effects of LS 82556 on thylakoid activities and photosynthesis: A comparison with paraquat and acifluorfen. Pestic. Biochem. Physiol. 29:209–216.Google Scholar
37. Vanstone, D. E. and Stobbe, E. H. 1979. Light requirement of the diphenylether herbicide oxyfluorfen. Weed Sci. 27:88–91.Google Scholar
38. Wakabayashi, K., Matsuya, K., Teraoka, T., Sandmann, G., and Böger, P. 1986. Effect of cyclic imide herbicides on chlorophyll formation in higher plants. J. Pestic. Sci. 11:635–640.Google Scholar
39. Walsch, C. T. 1984. Suicide substrates: mechanism-based enzyme inactivators; recent developments. Annu. Rev. Biochem. 53: 493–535.Google Scholar
40. Witkowski, D. A. and Halling, B. P. 1988. Accumulation of photodynamic tetrapyrroles induced by acifluorfen-methyl. Plant Physiol. 86:632–637.Google Scholar