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Protoporphyrinogen Oxidase-Inhibiting Herbicides

  • Stephen O. Duke (a1), John Lydon (a1), José M. Becerril (a1), Timothy D. Sherman (a1), Larry P. Lehnen (a1) and Hiroshi Matsumoto (a1)...

Abstract

Several commercial and experimental herbicides such as p-nitrodiphenyl ethers, oxadiazoles, and cyclic imides inhibit protoporphyrinogen IX oxidase (Protox), the enzyme that converts protoporphyrinogen IX to protoporphyrin IX (Proto). This leads to uncontrolled autooxidation of the substrate and results in accumulation of Proto. Blockage of the porphyrin pathway at this site inhibits synthesis of both chlorophylls and heme. Heme is a feedback regulator of the porphyrin pathway. Thus, inhibition of Protox also deregulates the pathway, causing increased carbon flow to the accumulating pool of Proto. Proto is a potent photosensitizer that generates high levels of singlet oxygen in the presence of molecular oxygen and light. In plants treated with these herbicides, damage is light dependent and closely correlated with the level of Proto that accumulates. Proto accumulation is apparently largely extraplastidic, resulting in rapid photodynamic damage to the plasmalemma and tonoplast. After high levels of Proto accumulate in response to these herbicides, protochlorophyllide (PChlide) levels can increase also; however, Proto appears to be the primary photodynamic pigment responsible for the herbicidal activity.

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1. Becerril, J. M. and Duke, S. O. 1989. Protoporphyrin DC content correlates with activity of photobleaching herbicides. Plant Physiol. 90:11751181.
2. Becerril, J. M. and Duke, S. O. 1989. Acifluorfen effects on intermediates of chlorophyll synthesis in green cucumber cotyledon tissues. Pestic. Biochem. Physiol. 35:119126.
3. Böger, P. 1984. Multiple modes of action of diphenyl ethers. Z. Naturforsch. 39C:468475.
4. Bowyer, J. R., Hallahan, B. J., Camilleri, P., and Howard, J. 1989. Mode of action studies on nitrodiphenyl ether herbicides, II. The role of photosynthetic electron transport in Scenedesmus obliquus . Plant Physiol. 89:674680.
5. Brenner, D. A. and Bloomer, J. R. 1980. Enzymatic defect in variegate porphyria — studies with human cultured skin fibroblasts. N. Engl. J. Med. 302:765769.
6. Camadro, J. M., Urban-Grimal, D., and Labbe, P. 1982. A new assay of protoporphyrinogen oxidase: Evidence for a total deficiency in that activity in a heme-less mutant of Saccharomyces cerevisiae . Biochem. Biophys. Res. Commun. 106:724730.
7. Castelfranco, P. A. and Beale, S. I. 1983. Chlorophyll biosynthesis: Recent advances and areas of interest. Annu. Rev. Plant Physiol. 34:241278.
8. Derrick, P. M., Cobb, A. H., and Pallett, K. E. 1988. Ultrastructural effects of the diphenyl ether herbicide acifluorfen and the experimental herbicide M&B 39279. Pestic. Biochem. Physiol. 32:153163.
9. Deybach, J. C., de Verneuil, H., and Nordmann, Y. 1981. The inherited enzymatic defect in porphyria variegate. Hum. Genet. 58:425428.
10. Duke, S. O., Becerril, J. M., Matsumoto, H., and Sherman, T. D. 1991. Photosensitizing porphyrins as herbicides. Am. Chem. Soc. Symp. Ser. 449:371386.
11. 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. 81:882888.
12. Duke, S. O. and Kenyon, W. H. 1987. A non-metabolic model of acifluorfen activity. Z. Naturforsch. 42C:813818.
13. Duke, S. O., Lydon, J., Paul, R. N. 1989. Oxadiazon activity is similar to that of p-nitro-diphenyl ether herbicides. Weed Sci. 37:152160.
14. Duke, S. O., Vaughn, K. C., and Meeusen, R. L. 1984. Mitochondrial involvement in the mode of action of acifluorfen. Pestic. Biochem. Physiol. 21:368376.
15. Ensminger, M. P. and Hess, F. D. 1985. Action spectrum of the activity of acifluorfen-methyl, a diphenyl ether herbicide, in Chlamydomonas eugametos . Plant Physiol. 77:503505.
16. Ensminger, M. P. and Hess, F. D. 1985. Photosynthesis involvement in the mechanism of action of diphenyl ether herbicides. Plant Physiol. 78:4650.
17. Ensminger, M. P., Hess, F. D., and Bahr, J. T. 1985. Nitro free radical formation of diphenyl ether herbicides is not necessary for their toxic action. Pestic. Biochem. Physiol. 23:163170.
18. Fadayomi, O. and Warren, G. F. 1976. The light requirement for herbicidal activity of diphenyl ethers. Weed Sci. 24:598600.
19. Ferreira, G. C., Andrew, T. L., Karr, S. W., and Dailey, H. A. 1988. Organization of the terminal enzymes of the heme biosynthetic pathway. J. Biol. Chem. 263:38353839.
20. Finckh, B. F. and Kunert, K. J. 1985. Vitamins C and E: An antioxidative system against herbicide-induced lipid peroxidation in higher plants. J. Agric. Food Sci. 33:574577.
21. Rear, D. S., Swanson, H. R., and Mansager, E. R. 1983. Acifluorfen metabolism in soybean: diphenylether bond cleavage and the formation of homoglutathione, cysteine, and glucose conjugates. Pestic. Biochem. Physiol. 20:299310.
22. 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. 31:112.
23. Gassman, M. A. 1973. The conversion of photoinactive protochlorophyllide663 to phototransformable protochlorophyllide650 in etiolated bean leaves treated with δ-aminolevulinic acid. Plant Physiol. 52:590594.
24. Halling, B. P. and Peters, G. R. 1987. Influence of chloroplast development on the activation of the diphenyl ether herbicide acifluorfen-methyl. Plant Physiol. 84:11141120.
25. Haworth, P. and Hess, F. D. 1988. The generation of singlet oxygen (IO2) by the nitro-diphenyl ether herbicide oxyfluorfen is independent of photosynthesis. Plant Physiol. 86:672676.
26. Jacobs, J. M. and Jacobs, N. J. 1987. Oxidation of protoporphyrinogen to protoporphyrin, a step in chlorophyll and haem biosynthesis. Purification and partial characterization of the enzyme from barley organelles. Biochem. J. 244:219224.
27. Kenyon, W. H. and Duke, S. O. 1985. Effects of acifluorfen on endogenous antioxidants and protective enzymes in cucumber (Cucumis sativus L.) cotyledons. Plant Physiol. 79:862866.
28. 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. 30:5766.
29. Kenyon, W. H., Duke, S. O., and Vaughn, K. C. 1985. Sequence of herbicidal effects of acifluorfen on ultrastructure and physiology of cucumber cotyledons. Pestic. Biochem. Physiol. 24:240250.
30. Kouji, H., Masuda, T., and Matsunaka, S. 1988. Action mechanism of diphenyl ether herbicides: Light-dependent O2 consumption in diphenyl ether-treated tobacco cell homogenate. J. Pestic. Sci. 13:495499.
31. Kouji, H., Masuda, T., and Matsunaka, S. 1989. Action mechanism of diphenyl ether herbicides: Stimulation of ALA synthesizing activities. Pestic. Biochem. Physiol. 33:230238.
32. Kunert, K. J., Sandmann, G., and Böger, P. 1987. Modes of action of diphenyl ethers. Rev. Weed Sci. 3:3555.
33. Lehnen, L. P., Sherman, T. D., Becerril, J. M., and Duke, S. O. 1990. Tissue and cell localization of acifluorfen-induced porphyrins in cucumber cotyledons. Pestic. Biochem. Physiol. 37:239298.
34. Lydon, J. and Duke, S. O. 1988. Porphyrin synthesis is required for photobleaching activity of the p-nitrosubstituted diphenyl ether herbicides. Pestic. Biochem. Physiol. 31:7483.
35. Mascia, P. N. and Robertson, D. S. 1978. Studies of chloroplast development in four maize mutants defective in chlorophyll biosynthesis. Planta 143:207211.
36. Masuda, T., Kouji, H., and Matsunaka, S. 1990. Diphenyl ether herbicide-decreased heme contents stimulate 5-aminolevulinic acid synthesis. Pestic. Biochem. Physiol. 36:106114.
37. 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. 27:267274.
38. Matringe, M. and Scalla, R. 1987. Induction of tetrapyrroles by diphenylether-type herbicides. Proc. Br. Crop Prot. Conf. 9B:981988.
39. Matringe, M. and Scalla, R. 1988. Studies on the mode of action of acifluorfen-methyl in non-chlorophyllous soybean cells: Accumulation of tetrapyrroles. Plant Physiol. 86:619622.
40. Matringe, M. and Scalla, R. 1988. Effects of acifluorfen-methyl on cucumber cotyledons: Protoporhyrin accumulation. Pestic. Biochem. Physiol. 32:164172.
41. Matringe, M., Camadro, J.-M., Labbe, P., and Scalla, R. 1989. Protoporphyrinogen oxidase as a molecular target for diphenyl ether herbicides. Biochem. J. 260:231235.
42. Matringe, M., Camadro, J.-M., Labbe, P., and Scalla, P. 1989. Protoporphyrinogen oxidase inhibition by three peroxidizing herbicides: oxadiazon, LS 82–556 and M&B 39279. FEBS Lett. 245:3538.
43. Matsunaka, S. 1969. Acceptor of light energy in photoactivation of diphenylether herbicides. J. Agric. Food Sci. 17:171–5.
44. Matsunaka, S. 1976. Diphenyl ethers. Pages 709739 in Kearney, P. C. and Kaufman, D. D., eds. Herbicides: Chemistry, Degradation, and Mode of Action. Vol. 2. Marcel-Dekker, New York.
45. Méallier, P., Emmelin, C., Périchet, G., and Tissut, M. 1989. Photodependent generation of reactive oxygen species by a phytotoxic pyridine derivative. Chemosphere 19:14271434.
46. Nicolaus, B., Sandmann, G., Watanabe, G., Wakabayashi, K., and Böger, P. 1989. Herbicide-induced peroxidation: Influence of light and diuron on protoporphyrin DC formation. Pestic. Biochem. Physiol. 35:192210.
47. Nurit, F., Ravanel, P., and Tissut, M. 1988. The photodependent effect of LS 82556 and acifluorfen in cucumber cotyledon pieces: The possible indirect involvement of photosynthesis. Pestic. Biochem. Physiol. 31:6773.
48. Orr, G. L., Elliott, C. M., and Hogan, M. E. 1983. Activity in vivo and redox sites in vitro of nitro- and chlorodiphenyl ether herbicide analogs. Plant Physiol. 73:939944.
49. Orr, G. L. and Hess, F. D. 1982. Mechanism of action of the diphenyl ether herbicide acifluorfen-methyl in excised cucumber (Cucumis sativus L.) cotyledons. Plant Physiol 69:502507.
50. Rao, D.N.R. and Mason, R. P. 1988. Photoreduction of some nitrobiphenyl ether herbicides to nitro radical anions by δ-carotene and related compounds. Photochem. Photobiol. 47:791795.
51. Rebeiz, C. A., Montazer-Zouhoor, A., Hopen, H. J., and Wu, S. -M. 1984. Photodynamic herbicides: 1. Concept and phenomenology. Enzyme Microb. Technol. 5:390401.
52. 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. 339:295328.
53. Rebeiz, C. A., Montazer-Zouhoor, A., Mayasich, J. M., Tripathy, B. C., Wu, S. -M., and Rebeiz, C. C. 1988. Phytodynamic herbicides. Recent developments and molecular basis of selectivity. CRC Crit. Rev. Plant Sci. 6:385436.
54. Sandmann, G. and Böger, P. 1988. Accumulation of protoporphyrin DC in the presence of peroxidizing herbicides. Z. Naturforsch. 43C:699704.
55. Sandmann, G. and Böger, P. 1990. Peroxidizing herbicides. Some aspects of tolerance. Am. Chem. Soc. Symp. Ser. 421:407418.
56. Sandmann, G., Reck, H., and Böger, P. 1984. Herbicidal mode of action on chlorophyll formation. J. Agric. Food Chem. 32:868872.
57. 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. 85:11461150.
58. Sato, R., Nagano, E., Oshio, H., and Kamoshita, K. 1988. Activities of the N-phenyl imide S-23142 in carotenoid-deficient seedlings of rice and cucumber. Pestic. Biochem. Physiol. 31:213220.
59. Shaaltiel, Y., Glazer, A., Bocion, P. F., and Gressel, J. 1988. Cross tolerance to herbicidal and environmental oxidants of plant biotypes tolerant to paraquat, sulfur dioxide, and ozone. Pestic. Biochem. Physiol. 31:1323.
60. Tanielian, C. and Wolff, C. 1988. Mechanism of physical quenching of singlet molecular oxygen by chlorophylls and related compounds of biological interest. Photochem. Photobiol. 48:277280.
61. Teraoka, T., Sandmann, G., Böger, P., and Wakabayashi, K. 1987. Effect of cyclic imide herbicides on pigment formation in plants. J. Pestic. Sci. 12:499504.
62. Towers, G.H.N. and Arnason, J. T., Arnason, J. T. 1988. Photodynamic herbicides. Weed Technol. 2:545549.
63. 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. 11:635640.
64. Wakabayashi, K., Sandmann, G., Ohta, H., and Böger, P. 1988. Peroxidizing herbicides: Comparison of dark and light effect. J. Pestic. Sci. 13:461471.
65. Wickliff, J. L., Duke, S. O., and Vaughn, K. C. 1982. Involvement of photobleaching and inhibition of protochlorophyll(ide) accumulation in tentoxin effects on greening mung bean seedlings. Physiol. Plant. 56:399406.
66. Witkowski, D. A. and Hailing, B. P. 1988. Accumulation of photodynamic tetrapyrroles induced by acifluorfen-methyl. Plant Physiol. 87:632637.
67. Witkowski, D. A. and Hailing, B. P. 1989. Inhibition of plant protoporphyrinogen oxidase by the herbicide acifluorfen-methyl. Plant Physiol. 90:12391242.
68. Yanase, D. and Andoh, A. 1989. Porphyrin synthesis involvement in diphenyl ether-like mode of action of TNPP-ethyl, a novel phenylpyrazole herbicide. Pestic. Biochem. Physiol. 35:7080.

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Protoporphyrinogen Oxidase-Inhibiting Herbicides

  • Stephen O. Duke (a1), John Lydon (a1), José M. Becerril (a1), Timothy D. Sherman (a1), Larry P. Lehnen (a1) and Hiroshi Matsumoto (a1)...

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