Protoporphyrinogen Oxidase-Inhibiting Herbicides

Hayes' Handbook of Pesticide Toxicology

Volumn , Issue , 2010, Pages 1733-1751

  Dayan, Franck E ^a   Duke, Stephen O ^a  

^a United States Department of Agriculture ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650648798     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-374367-1.00081-1     Document Type: Chapter

References (147)

1. Adler I.L., Jones B.M., Waego J.P. Fate of 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene (oxyfluorfen) in rats. J. Agric. Food Chem. 1977, 25:1339-1341.
2. Herbicide Handbook 1994, Weed Science Society of America, Champaign, IL. 7th ed. W.H. Ahrens (Ed.).
3. Aizawa K., Brown H.M. Metabolism and degradation of porphyrin biosynthesis inhibitor herbicides. Peroxidizing Herbicides 1999, 371-383. Springer-Verlag, Berlin. P. Böger, K. Wakabayashi (Eds.).
4. Amuti, K., Trombinin, A., Giammarrusti, L., Sbriscia, C., Harder, H., and Gabard, J. (1997). Azafenidin, a new low use rate herbicide for weed control in perennial crops, industrial weed control and forestry. In "Brighton Crop Protection Conference," pp. 59-66.
5. Anderson R.J., Norris A.E., Hess F.D. Synthetic organic chemicals that act through the porphyrin pathway. Am. Chem. Soc. Symp. Ser. 1994, 559:18-33.
6. "Authority Herbicide," Technical Information Bulletin 1995, Anonymous, FMC Corporation, Philadelphia.
7. "Carfentrazone-Ethyl Herbicide," Technical Information Bulletin 1995, Anonymous, FMC Corporation, Philadelphia.
8. Armbruster B.L., Clark R.D., Sharp C.R., Dill G.M. Herbicidal action of nitrophenyl pyrazole ether MON 12800: Immunolocalization, ultrastructural, and physiological studies. Pestic. Sci. 1993, 47:21-35.
9. Becerril J.M., Duke S.O. Protoporphyrin IX content correlates with activity of photobleaching herbicides. Plant Physiol. 1989, 90:1175-1181.
10. Birchfield N.B., Casida J.E. Protoporphyrinogen oxidase of mouse and maize: Target site selectivity and thiol effects on peroxidizing herbicide action. Pestic. Biochem. Physiol. 1997, 57:36-43.
11. Böger P. Multiple modes of action of diphenyl ethers. Z. Naturforsch C. Biosci. 1984, 39:468-475.
12. Bray H.G., James S.P., Thorpe W.V., Wasdell M.R. The metabolism of ethers in the rabbit. Biochem. J. 1953, 54:547-551.
13. Choi K.W., Han O., Lee H.J., Yun Y.C., Moon Y.H., Kim M., Kuk Y.I., Han S.U., Guh J.O. Generation of resistance to the diphenyl ether herbicide, oxyfluorfen via expression of the Bacillus subtilis protoporphyrinogen oxidase gene in transgenic: On tobacco plants. Biosci. Biotechnol. Biochem. 1998, 62:558-560.
14. Clark R.D. Synthesis of protoporphyrinogen oxidase inhibitors. Am. Chem. Soc. Symp. Ser. 1994, 559:34-47.
15. Clark R.D. Synthesis and QSAR of herbicidal 3-pyrazoyl α,α,α-trifluorotolyl ethers. J. Agric. Food Chem. 1996, 44:3643-3652.
16. Condon M.E., Alvarado S.I., Arthen F.J., Birk J.H., Brady T.E., Crews A.D., Marc J.H., Karp G.M., Lavanish J.M., Nielsen D.R., Lies T.A. 6-aryloxy-lH-benzotriazoles. Am. Chem. Soc. Symp. Ser. 1995, 584:123-135.
17. Corradi H.R., Corrigall A.V., Boix E., Mohan C.G., Sturrock E.D., Meissner P.N., Acharya K.R. Crystal structure of protoporphyrinogen oxidase from Myxococcus xanthus and its complex with the inhibitor acifluorfen. J. Biol. Chem. 2006, 281:38625-38633.
18. Cox G.S., Krieg M., Whitten D.G. Self-sensitized photooxidation of protoporphyrin IX derivatives in aqueous surfactant solutions: Product and mechanistic studies. J. Am. Chem. Soc. 1982, 104:6930-6937.
19. Dann E.K., Diers B.W., Hammerschmidt R. Suppression of Scherotina stem rot of soybean by lactofen herbicide treatment. Phytopathology 1999, 89:598-602.
20. Dayan F.E., Duke S.O. Porphyrin-generating herbicides. Pestic. Outlook 1996, 7:22-27.
21. Dayan F.E., Duke S.O. Phytotoxicity of protoporphyrinogen oxidase inhibitors: Phenomenology, mode of action and mechanisms of resistance. Herbicide Activity: Toxicology, Biochemistry and Molecular Biology 1997, 11-35. IOS Press, Amsterdam. R.M. Roe, J.D. Burton, R.J. Kuhr (Eds.).
22. Dayan F.E., Weete J.D., Hancock H.G. Physiological basis for differential sensitivity to sulfentrazone by sicklepod (Senna obtusifolia) and coffee senna (Cassia occidentalis). Weed Sci. 1996, 44:12-17.
23. Dayan F.E., Duke S.O., Reddy K.N., Hamper B.C., Leschinsky K.L. Effect of isoxazole herbicides on protoporphyrinogen oxidase and porphyrin physiology. J. Agric. Food Chem. 1997, 45:967-975.
24. Dayan F.E., Duke S.O., Weete J.D., Hancock H.G. Selectivity and mode of action of carfentrazone-ethyl, a novel phenyl triazolinone herbicide. Pestic. Sci. 1997, 51:65-73.
25. Dayan F.E., Weete J.D., Duke S.O., Hancock H.G. Soybean (Glycine max) cultivar differences in response to sulfentrazone. Weed Sci. 1997, 45:634-641.
26. Dayan F.E., Armstrong B.M., Weete J.D. Inhibitory activity of sulfentrazone and its metabolic derivatives on soybean (Glycine max) protoporphyrinogen oxidase. J. Agric. Food Chem. 1998, 46:2024-2029.
27. Dayan F.E., Reddy K.N., Duke S.O. Structure-activity relationships of diphenyl ethers and other oxygen-bridged protoporphyrinogen oxidase inhibitors. Peroxidizing Herbicides 1999, 144-162. Springer-Verlag, Berlin. P. Böger, K. Wakabayashi (Eds.).
28. Dayan F.E., Romagni J.G., Duke S.O. Protoporphyrinogen oxidase inhibitors. Handbook of Pesticide Toxicology 2001, Vol. 2:1529-1542. Academic Press, San Diego. 2nd ed. R. Krieger, J. Doull, D. Ecobichon, D. Gammon, E. Hodgson, L. Reiter, J. Ross (Eds.).
29. de Castro V.L.S.S., Destefani C.R., Diniz C., Poli C. Evaluation of neurodevelopmental effects on rats exposed prenatally to sulfentrazone. Neurotoxicology 2007, 28:1249-1259.
30. Devine, M. D., Duke, S. O., and Fedtke, C. (1993). Oxygen toxicity and herbicidal action. In "Physiology of Herbicide Action", pp. 177-189. Prentice Hall, Englewood Cliffs, NJ.
31. Deybach J.C., de Vemeuil H., Nordmann Y. The inherited enzymatic defect in porphyria variegata. Hum. Genet. 1981, 58:425-428.
32. Dickmann, R., Melgarejo, J., Loubiere, P., and Montagnon, M. (1997). Oxadiargyl, a novel herbicide for rice and sugarcane. In "Brighton Crop Protection Conference," pp. 51-57.
33. Duke S.O. Taking stock on herbicide-resistant crops ten years after introduction. Pest Manag. Sci. 2005, 61:211-218.
34. Duke S.O., Kenyon W.H. Photosynthesis is not involved in the mechanism of action of acifluorfen in cucumber (Cucumis sativus L.). Plant Physiol. 1986, 81:882-888.
35. Duke S.O., Powles S.B. Glyphosate: A once in a century herbicide. Pest Manag. Sci. 2008, 64:319-325.
36. Duke S.O., Rebeiz C.A. Porphyric pesticides: Chemistry, toxicology, and pharmaceutical applications. Am. Chem. Soc. Symp. Ser. 1994, 559.
37. Duke S.O., Lydon J., Becerril J., Sherman T.D., Lehnen L.P., Matsumoto M. Protoporphyrinogen oxidase-inhibiting herbicides. Weed Sci. 1991, 39:465-473.
38. Duke S.O., Lee H.J., Duke M.V., Reddy K.N., Sherman T.D., Becerril J.M., Nandihalli U.B., Matsumoto H., Jacobs N.J., Jacobs J.M. Mechanisms of resistance to protoporphyrinogen oxidase-inhibiting herbicides. Herbicide Resistance in Crops and Weeds 1997, 155-160. Kluwer, Amsterdam. R. DePrado, L. García-Torres, J. Jorrin (Eds.).
39. Duke S.O., Wedge D.E., Cerdeira A.L., Matallo M.B. Interactions of synthetic herbicides with plant disease and microbial herbicides. Novel Biotechnologies for Biocontrol Agent Enhancement and Management 2007, 277-296. Springer, Dordrecht, The Netherlands. M. Vurro, J. Gressel (Eds.).
40. El Naggar, S. F., Creekmore, R. W., Cornell, S. S., Dunn, C., McLaughlin, T. (2000). Metabolism of benzfendizone herbicide in rat. Abstract A.C.S. 220th Agro-114.
41. Falk J.S., Shoup D.E., Al-Khatib K., Peterson D.E. Survey of common waterhemp (Amaranthus rudis) response to Protox- and ALS-inhibiting herbicides in northeast Kansas. Weed Technol. 2005, 19:838-846.
42. Falk J.S., Al-Khatib K., Peterson D.E. Protox-resistant common waterhemp (Amaranthus rudis) response to herbicides applied at different growth stages. Weed Sci. 2006, 54:793-799.
43. Fonne-Pfister, R., De Marco, A., and Volrath, S. L. (2001). Protoporphyrinogen oxidase genes of crop plants and their use in the development of herbicide-resistant plants. PCT Int. App. 6 WO2001-EP2753 20010312.
44. Frear D.S., Swanson H.R. Metabolism of substituted diphenyl ether herbicides in plants: I. Enzymic cleavage of fluorodifen in peas (Pisum sativum). Pestic. Biochem. Physiol. 1973, 3:473-482.
45. Frear D.S., Swanson H.R., Mansager E.R. Acifluorfen metabolism in soybean: Diphenyl ether bond cleavage and the formation of homoglutathione, cysteine and glucose conjugates. Pestic. Biochem. Physiol. 1983, 20:299-310.
46. Gianessi L.P. Economic impacts of glyphosate-resistant crops. Pest Manag. Sci. 2008, 64:346-352.
47. Gilham D.J., Dodge A.D. The mode of action of nitro-diphenyl ether herbicides. Progress in Pesticide Biochemistry and Physiology 1987, Vol. 7:147-167. Wiley, New York. D.H. Hutson, T.R. Roberts (Eds.).
48. Graham M.Y. The diphenylether herbicide lactofen induces cell death and expression of defense-related genes in soybean. Plant Physiol. 2005, 139:1784-1794.
49. Gressel J., Levy A.A. Agriculture: The selector of improbable mutations. Proc. Natl. Acad. Sci. USA 2006, 103:12215-12216.
50. Grey T.L., Walker R.H., Wehtje G.R., Hancock H.G. Sulfentrazone adsorption and mobility as affected by soil and pH. Weed Sci. 1997, 45:733-738.
51. Halling B.P., Yuhas D.A., Fingar V.F., Winkelmann J.W. Protoporphyrinogen oxidase inhibitors for tumor therapy. Am. Chem. Soc. Symp. Ser. 1994, 559:280-290.
52. Hamper B.C., Leschinsky K.L., Massey S.S., Bell C.L., Brannigan L.H., Prosch S.D. Synthesis and herbicidal activity of 3-aryl-5-(haloalkyl)-4-isoxazolecarboxamides and their derivatives. J. Agric. Food Chem. 1995, 43:219-228.
53. Heap, I. (2008). International survey of herbicide resistant weeds. Available at (accessed July 2008). http://www.weedscience.org/In.asp.
54. Horikoshi, M., and Hirooka, T. (1997). Cloning of plant protoporphyrinogen oxidase cDNA and production of transgenic plants resistant to light-dependent type herbicides. Japanese patent JP 09275986.
55. Hou Z., Ren Y., Lei M., Huang M., Song J., Chen L. Synthesis and biological evaluation of novel N-benzoxazolonyluracils as Protox-inhibitor. Trans. Tianjin Univers 2005, 11:26-29.
56. Huang M-Z., Huang K.-L., Ren Y.-G., Lei M.-X, Huang L., Hou Z.-K., Liu A.-P., Ou X.-M. Synthesis and herbicidal activity of 2-(7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1, 3-diones. J. Agric. Food Chem. 2005, 53:7908-7914.
57. Hunt L.M., Chamberlain W.F., Gilbert B.N., Hopkins D.E., Gingrich A.R. Absorption, excretion, and metabolism of nitrofen by a sheep. J. Agric. Food Chem. 1977, 25:1062-1065.
58. Ichinose K., Che F.-S., Kimura Y., Matsunobu A., Sato F., Yoshida S. Selection and characterization of protoporphyrinogen oxidase inhibiting herbicide (S23142) resistant photomixotrophic cultured cells of Nicotiana tabacum. J. Plant Physiol. 1995, 146:693-698.
59. Jacobs J.M., Jacobs N.J., Sherman T.D., Duke S.O. Effect of diphenyl ether herbicides on oxidation of protoporphyrinogen to protoporphyrin in organellar and plasma membrane-enriched fractions of barley. Plant Physiol. 1991, 97:197-203.
60. Jacobs J.M., Jacobs N.J., Duke S.O. Protoporphyrinogen destruction by plant extracts and correlation with tolerance to protoporphyrinogen oxidase inhibiting herbicides. Pestic. Biochem. Physiol. 1996, 55:77-83.
61. Johnson W.O., Kollman G.E., Swithenbank C., Yih R.Y. RH-6201 (Blazer): A new broad spectrum herbicide for postemergence use in soybean. J. Agric. Food Chem. 1978, 26:285-286.
62. Jung H.I., Kuk Y.I. Resistance mechanisms in protoporphyrinogen oxidase (PROTOX) inhibitor-resistant transgenic rice. J. Plant Biol. 2007, 50:586-594.
63. Jung H.I., Kuk Y.I., Back K., Burgos N.R. Resistance pattern and antioxidant enzyme profiles of protoporphyrinogen oxidase (PROTOX) inhibitor-resistant transgenic rice. Pestic. Biochem. Physiol. 2008, 91:53-65.
64. Karp G.M., Condon M.E., Arthen F.J., Birk J.H., Marc P.A., Hunt D.A., Lavanish J.M., Schwindeman J.A. Aryloxyindolin-2(3H)-ones. Am. Chem. Soc. Symp. Ser. 1995, 584:136-148.
65. Kawamura S., Kato T., Matsuo M., Katsuda Y., Yasuda M. Species difference in protoporphyrin IX accumulation produced by an N-phenylimide herbicide in embryos between rats and rabbits. Toxicol. Appl. Pharmacol. 1996, 141:520-525.
66. Kenyon W.H., Duke S.O., Vaughn K.C. Sequences of effects of acifluorfen on physiological and ultrastructural parameters in cucumber cotyledon discs. Pestic. Biochem. Physiol. 1985, 24:240-250.
67. Koch M., Breithaupt C., Kiefersauer R., Freigang J., Huber R., Messerschmidt A. Crystal structure of protoporphyrinogen IX oxidase: A key enzyme in haem and chlorophyll biosynthesis. EMBO J. 2004, 23:1720-1728.
68. Komives T., Casida J.E. Diphenyl ether herbicides: Effects of acifluorfen on phenylpropanoid biosynthesis and phenylalanine ammonia-lyase activity in spinach. Pestic. Biochem. Physiol. 1982, 18:191-196.
69. Komives T., Casida J.E. Acifluorfen increases the leaf content of phytoalexins and stress metabolites in several crops. J. Agric. Food Chem. 1983, 31:751-755.
70. Krijt J., Vokurda M., Sanitrák J., Janousek V. Effect of protoporphyrinogen oxidase inhibition on mammalian porphyrin metabolism. Am. Chem. Soc. Symp. Series. 1994, 559:247-254.
71. Krijt J., Stranska P., Maruna P., Vokurka M., Sanitrák J. Herbicide-induced experimental variegate porphyria in mice: Tissue porphyrinogen accumulation and response to porphyrogenic drugs. Can. J. Physiol. Pharmacol. 1997, 75:1181-1187.
72. Kuk Y.I., Lee H.J., Chung J.S., Kim K.M., Lee S.B., Ha S.B., Back K., Guh J.O. Expression of a Bacillus subtilis protoporphyrinogen oxidase gene in rice plants reduces sensitivity to peroxidizing herbicides. Biol. Plant 2005, 49:577-583.
73. Kunert K.J., Sandmann G., Böger P. Modes of action of diphenyl ethers. Rev. Weed Sci. 1987, 3:35-55.
74. Lee H.J., Duke M.V., Duke S.O. Cellular localization of protoporphyrinogen-oxidizing activities of etiolated barley (Hordeum vulgare L.) leaves. Plant Physiol. 1993, 102:881-889.
75. Lee H.J., Duke M.V., Birk J.H., Yamamoto M., Duke S.O. Biochemical and physiological effects of benzheterocycles and related compounds. J. Agric. Food Chem. 1995, 43:2722-2727.
76. Lee H.J., Lee S.B., Chung S.J., Sung U., Han O., Guh O.J., Jeon J.S., An G., Back K. Transgenic rice plants expressing a Bacillus subtilis protoporphyrinogen oxidase gene are resistant to dephenyl either herbicide oxyfluorfen. Plant Cell Physiol. 2000, 41:743-749.
77. Lee K., Yang K., Kang K., Kang S., Lee N., Back K. Use of Myxococcus xanthus protoporphyrinogen oxidase as a selectable marker for transformation of rice. Pestic. Biochem. Physiol. 2007, 88:31-35.
78. Lee R.M., Hager A.G., Tranel P.J. Prevalence of a novel resistance mechanism to PPO-inhibiting herbicides in waterhemp (Amaranthus tuberculatus). Weed Sci. 2008, 56:371-375.
79. Lehnen L.P., Sherman T.D., Becerril J.M, Duke S.O. Tissue and cellular localization of acifluorfen-induced porphyrins in cucumber cotyledons. Pestic. Biochem. Physiol. 1990, 37:239-248.
80. Lermontova I., Grimm B. Overexpression of plastidic protoporphyrinogen IX oxidase leads to resistance to the diphenyl-ether herbicide acifluorfen. Plant Physiol. 2000, 122:75-84.
81. Leung L.Y., Lyga J.W., Robinson R.A. Metabolism and distribution of the experimental triazolinone herbicide sulfentrazone in the rat, goat and hen. J. Agric. Food Chem. 1991, 39:1509-1514.
82. Li J., Smeda R.J., Dayan F.E. Physiological basis for resistance to diphenyl ether herbicides in common waterhemp (Amaranthus rudis). Weed Sci. 2004, 52:333-338.
83. Li X., Nicholl D. Development of PPO inhibitor-resistant cultures and crops. Pest Manag. Sci. 2005, 61:277-285.
84. Luo Y.-P., Jiang L.-L., Wang G.-D., Chen Q., Yang G.-F. Syntheses and herbicidal activities of novel triazolinone derivatives. J. Agric. Food Chem. 2008, 56:2118-2124.
85. Lydon J., Duke S.O. Porphyrin synthesis is required for photobleaching activity of the p-nitrosubstituted diphenyl ether herbicides. Pestic. Biochem. Physiol. 1988, 31:74-83.
86. Lydon J., Duke S.O. Inhibitors of glutamine biosynthesis. Plant Amino Acids: Biochemistry and Biotechnology 1998, 445-463. Dekker, New York. B.K. Singh, (Ed.).
87. Lyga J.W., Patera R.M., Theodoridis G., Hailing B.P., Hotzman F.W., Plummer M.J. Synthesis and quantitative structure-activity relationships of herbicidal N-(2-fluoro-5-methoxyphenyl)-3,4,5,6-tetrahydrophthalimides. J. Agric. Food Chem. 1991, 39:1667-1673.
88. Matringe M., Scalla R. Effects of acifluorfen-methyl on cucumber cotyledons: Protoporphyrin accumulation. Pestic. Biochem. Physiol. 1988, 32:164-168.
89. Matringe M., Camadro J.-M., Labbe P., Scalla R. Protoporphyrinogen oxidase as a molecular target for diphenyl ether herbicides. Biochem. J. 1989, 260:231-235.
90. Matringe M., Camadro J.-M., Labbe P., Scalla R. Protoporphyrinogen oxidase inhibition by three peroxidizing herbicides: Oxadiazon, LS 82-556 and M&B 39279. FEBS Lett. 1989, 245:35-38.
91. 3H]acifluorfen binding to purified pea etioplasts, and evidence that proto-porphyrinogen oxidase specifically binds acifluorfen. Eur. J. Biochem. 1992, 209:861-868.
92. Matsumoto H., Lee J.J., Ishizuka K. Variation in crop response to protoporphyrinogen oxidase inhibitors. Am. Chem. Soc. Symp. Ser. 1994, 559:120-132.
93. Matsunaka S. Acceptor of light energy in photoactivation of diphenyl ether herbicides. J. Agric. Food Chem. 1969, 17:171-175.
94. Matsunaka S. Diphenyl ether herbicides. Herbicides: Chemistry, Degradation and Mode of Action 1976, Vol. 2:709-739. Dekker, New York. P.C. Kearney, D.D. Kaufman (Eds.).
95. Mito N., Sato R., Miyakado M., Oshio H., Tanaka S. In vitro mode of action of N-phenylimide photobleaching herbicides. Pestic. Biochem. Physiol. 1991, 40:128-135.
96. Nakajima, H., and Nagasawa, A. (2005). Protoporphyrinogen IX oxidase variant-expressing transgenic plants resistant to weed herbicidal compounds which disrupt the porphyrin pathways of plants. U.S. 6,570,070, 88 pp.
97. Nandihalli U.B., Duke S.O. The porphyrin pathway as a herbicide target site. Am. Chem. Soc. Symp. Ser. 1993, 524:62-78.
98. Nandihalli U.B., Duke M.V., Duke S.O. Quantitative structure-activity relationships of protoporphyrinogen oxidase-inhibiting diphenyl ether herbicides. Pestic. Biochem. Physiol. 1992, 43:193-211.
99. Nandula V.K., Reddy K.N, Duke S.O., Poston D.H. Glyphosate-resistant weeds: Current status and future outlook. Outlooks Pest Manag. 2005, 16:183-187.
100. Evaluation of the New Active Butafenacil 2002, National Registration Authority, National Registration Authority for Agricultural and Veterinary Chemicals, Kingston, Australia.
101. Patzoldt W.L., Tranel P.J., Hager A.G. A waterhemp (Amaranthus tuberculatus) biotype with multiple resistance across three herbicide sites of action. Weed Sci. 2005, 53:30-36.
102. Patzoldt W.L., Hager A.G., McCormick J.S., Tranel P.J. A codon deletion confers resistance to herbicides inhibiting protoporphyrinogen oxidase. Proc. Natl. Acad. Sci. USA 2006, 103:12329-12334.
103. Pornprom T., Matsumoto H., Usui K., Ishizuka K. Characterization of oxyfluorfen tolerance in selected soybean line. Pestic. Biochem. Physiol. 1994, 50:107-114.
104. Prosch, S. D., Ciha, A. J., Grogna, R., Hamper, B. C., Feucht, D., and Dreist, M. (1997). JV 485: A new herbicide for pre-emergence broad spectrum weed control in winter wheat. In "Brighton Crop Protection Conference," pp. 45-50.
105. Reddy K.N., Nandihalli U.B., Lee H.J., Duke M.V., Duke S.O. Predicting activity of protoporphyrinogen oxidase inhibitors by computer-aided molecular modeling. Am. Chem. Soc. Symp. Series. 1995, 589:221-224.
106. Reddy K.N., Dayan F.E., Duke S.O. QSAR analysis of protoporphyrinogen oxidase inhibitors. Comparative QSAR 1998, 197-234. Taylor & Francis, London. J. Devillers (Ed.).
107. Ritter R.L., Coble H.D. Influence of temperature and relative humidity on the activity of acifluorfen. Weed Sci. 1981, 29:480-485.
108. Ritter R.L., Coble H.D. Penetration, translocation, and metabolism of acifluorfen in soybean (Glycine max), common ragweed (Ambrosia artemissifolia), and cocklebur (Xanthium pensylvanicum). Weed Sci. 1981, 29:474-480.
109. Sanyal D., Shrestha A. Direct effect of herbicides on plant pathogens and disease development in various cropping systems. Weed Sci. 2008, 56:155-160.
110. Sato R., Nagano E., Oshio H., Kamoshita K. Diphenylether-like physiological and biochemical actions of S-23142, a novel N-phenylimide herbicide. Pestic. Biochem. Physiol. 1987, 28:194-200.
111. Scalla R., Matringe M. Inhibitors of protoporphyrinogen oxidase as herbicides: Diphenyl ethers and related photobleaching molecules. Rev. Weed Sci. 1994, 6:103-132.
112. Schiffer, H., Lerchl, J., Grimm, B., Lermontova, I., and Voronetskaja, V. (2001). Protoporphyrin oxidase analogs resistant to herbicidal inhibitor and genes enducing them and the development of herbicide resistant plants. PCT Int. Appl. 6 WO 0136606 A2 200010525.
113. Herbicide Handbook 2007, Weed Science Society of America, Lawrence, KS. 9th ed. S.A. Senseman (Ed.).
114. Shaner D.L. Herbicide safety relative to common targets in plants and mammals. Pest Manag. Sci. 2003, 60:17-24.
115. Sherman T.D., Duke M.V., Clark R.D., Sanders E.F., Matsumoto H., Duke S.O. Pyrazole phenyl ether herbicides inhibit protoporphyrinogen oxidase. Pestic. Biochem. Physiol. 1991, 40:236-245.
116. Shoup D.E., Al-Khatib K. Fate of acifluorfen and lactofen in common waterhemp (Amaranthus rudis) resistant to protoporphyrinogen oxidase-inhibiting herbicides. Weed Sci. 2005, 53:284-289.
117. Shoup D.E., Al-Khatib K., Peterson D.E. Common waterhemp (Amaranthus rudis) resistance to protoporphyrinogen oxidase-inhibiting herbicides. Weed Sci. 2003, 51:145-150.
118. Smith D.A., Hallett S.G. Interactions between chemical herbicides and the candidate bioherbicide Microsphaeropsis amaranthi. Weed Sci. 2006, 54:532-537.
119. Sumida M., Niwata S., Fukami H., Tanaka T., Wakabayashi K., Böger P. Synthesis of novel diphenyl ether herbicides. J. Agric. Food Chem. 1995, 43:1929-1934.
120. Tanaka, A., Tanaka, R., Kato, K., and Fukagawa, T. (2007). DNA and protein sequences of Synechocystis protoporphyrinogen oxidase and its use for plant acifluorfen resistance and screening of herbicides. PCT Int. Appl. WO 2007034953 A1 20070329.
121. Theodoridis G. Structure-activity relationships of herbicidal aryltria-zolinones. Pestic. Sci. 1997, 50:283-290.
122. Theodoridis G., Baum J.S., Hotzman F.W., Manfredi M.C., Maravetz L.L., Lyga J.W., Tymonko J.M., Wilson K.R., Poss K.M., Wyle M.J. Synthesis and herbicidal properties of aryltriazolinones. A new class of pre- and postemergence herbicides. Am. Chem. Soc. Symp. Ser. 1992, 504:135-146.
123. Theodoridis G., Bahr J.T., Davidson B.L., Hart S.E., Hotzman F.W., Baum J.S., Hotzman F.W., Poss K.M., Tutt S.F. Alkyl 3-[2,4-disubstituted-4,5-dihydro-3-methyl-5-oxo-1 H-1,2,4-triazol-1-yl)phenyl]propenoate derivatives: Synthesis and structure-activity relationships. Am. Chem. Soc. Symp. Ser. 1995, 584:90-99.
124. Theodoridis G., Bahr J.T., Hotzman F.W., Sehgel S., Suarez D.P. New generation of Protox-inhibiting herbicides. Crop. Prot. 2000, 19:533-536.
125. Tomigahara Y., Onogi M., Kaneko H., Nakatsuka I., Yamane S. Metabolism of 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4- (2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (S-53482, flumioxazin) in the rat: II. Identification of reduced metabolites. J. Agric. Food Chem. 1999, 47:2429-2438.
126. Trezzi M.M., Felippi C.L., Mattei D., Silva H.L., Nunes A.L., Debastiani C., Vidal R.A., Marques A. Multiple resistance of acetolactate synthase and protoporphyrinogen oxidase inhibitors in Euphorbia heterophylla biotypes. J. Environ. Sci. Health B Pestic. Food Contam. Agric. Wastes 2005, B40:101-109.
127. Tripathy B.C., Mohapatra A., Gupta I. Impairment of the photosynthetic apparatus by oxidative stress induced by photosensitization reaction of protoporphyrin IX. Biochim. Biophys. Acta 2007, 1767:860-868.
128. U.S. Department of Agriculture, National Agricultural Statistics Service (USDA-NASS) (2008) (accessed July 2008). http://www.nass.usda.gov.
129. Vidrine P.R., Reynolds D.B., Griffin J.L. Weed control in soybean (Glycine max) with lactofen plus chlorimuron. Weed Technol. 1993, 7:311-316.
130. Vidrine P.R., Jordan D.L., Girlinghouse J.M. Efficacy of F-6285 in soybeans. Proc. South. Weed Sci. Soc. 1994, 47:62.
131. Vidrine P.R., Griffin J.L., Jordan D.L., Reynolds D.B. Broadleaf weed control in soybean (Glycine max) with sulfentrazone. Weed Technol. 1996, 10:762-765.
132. Volrath, S. L., Johnson, M. A., Ward, E. R., and Heifetz, P. B. (1999). Genes encoding herbicide inhibitor-resistant mutants of plant protoporphyrinogen oxidase and transgenic crop plants expressing same. U.S. Patent 5939602.
133. Volrath, S. L., Johnson, M. A., Potter, S. L., Ward, E. R., and Heifetz, P. B. (2000a). Protoporphyinogen oxidases of crop plants and genes encoding them and the development of herbicide-resistant plants. U.S. Patent 6023012.
134. Volrath, S. L., Johnson, M. A., Ward, E. R., and Heifetz, P. B. (2000b). Plant genes for protoporphyrinogen oxidases and the development of herbicide-resistant forms of the enzyme. U.S. Patent 6084155.
135. Walker R.H., Richburg J.S., Jones R.E. F6285 efficacy as affected by rate and method of application. Proc. South. Weed Sci. Soc. 1992, 45:51.
136. Warabi E., Usui K., Tanaka Y., Matsumoto H. Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial protoporphyrinogenic oxidase. Pest. Manage. Sci. 2001, 57:743-748.
137. Ward, E. R., and Volrath, S. (1995). Manipulation of protoporphyrinogen oxidase enzyme activity in eukaryotic organisms. International Patent Application WO 95/34659.
138. Ward, E. R., and Volrath, S. L. (1998). Manipulation of protoporphyrinogen oxidase enzyme activity in eukaryotic organisms. U.S. Patent 5767373.
139. Ward, E. R., Voltrath, S. L., Johnson, M. A., and Potter, S. L. (2001). Herbicide-tolerant protoporphyrinogen oxidase produced by DNA shuffling of plant genes. U.S. Pat. Appl. Publ. 20010016956 A120010823.
140. Watanabe N., Che F.S., Iwano M., Nakano T., Takayama S., Yoshida S., Isogai A. Molecular characterization of photomixotrophic tobacco cells resistant to photoporphyrinogen oxidase-inhibiting herbicides. Plant Physiol. 1998, 118:451-458.
141. Watanabe N., Che F.-S., Iwano M., Takayama S., Yoshida S. Dual targeting of spinach protoporphyrinogen oxidase II to mitochondria and chloroplasts by alternative use of two in-frame initiation codons. J. Biol. Chem. 2001, 276:20474-20481.
142. Wehtje G.R., Walker R.H., Grey T.L., Hancock H.G. Response of purple (Cyperus rotundus) and yellow nutsedge (Cyperus esculentus) to selective placement of sulfentrazone. Weed Sci. 1997, 45:382-387.
143. Wepplo P., Birk J.H., Lavanish J.M., Mandredi M., Nielsen D.R. 5-Aryloxybenzisoxazole esters. Am. Chem. Soc. Symp. Ser. 1995, 584:149-160.
144. Wills G.D., McWhorter C.G. Effect of environment on the translocation and toxicity of acifluorfen to showy crotalaria (Crotalaria spectabilis). Weed Sci. 1981, 29:397-401.
145. Witkowski D.A., Halling B.P. Accumulation of photodynamic tetrapyrroles induced by aciflurogen-methyl. Plant Physiol. 1988, 87:632-637.
146. Yun, Y. -C., Moon, Y. -H., Choi, J. -N., Choi, K. -W., Kim, C. -H., Kim, M. -K., Guh, J. -O., and Jeon, H. -S. (1997). Herbicide-tolerant transgenic plants expressing protoporphyrinogen oxidase. Eur. Pat. Appl. 6 EP 770682 A2 19970502.
147. Zhang Q., Huang M., Min Z., Chen W. Research progress on herbicidally active uracil derivatives. Nongyao 2006, 45:73-77.