Metabolism-based herbicide resistance: Regulation by safeners

Weed Science

Volumn 52, Issue 3, 2004, Pages 454-467

  Hatzios, Kriton K ^a   Burgos, Nilda ^b  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b UNIVERSITY OF ARKANSAS   (United States)

Author keywords

ATP binding cassette transporters; Cytochrome P450 monooxygenases; Glucosyl transferases; Glutathione; Glutathione S transferases; Herbicide metabolism; Herbicide resistance; Herbicide safeners; Regulation of herbicide metabolism

Indexed keywords

HERBICIDE; MAIZE; METABOLISM; PESTICIDE RESISTANCE; PHYTOTOXICITY; RICE;

SORGHUM BICOLOR BICOLOR; TRITICUM AESTIVUM; ZEA MAYS;

EID: 19944421312     PISSN: 00431745     EISSN: None     Source Type: Journal    
DOI: 10.1614/P2002-168C     Document Type: Conference Paper

References (131)

1. Adams, C. A., E. Blee, and J. E. Casida. 1983. Dichloroacetamide herbicide antidotes enhance sulfate metabolism in corn roots. Pestic. Biochem. Physiol. 19:350-360.
2. Alfenito, M. and V. Walbot. 1997. Flavonoids and phytohormones, two toxic secondary metabolites are GST substrates. Pages 197-208 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
3. Anderson, M. P. and J. W. Gronwald. 1991. Atrazine resistance in a velveltleaf (Abutilon theophrasti) biotype due to enhanced glutathione S-transferase activity. Plant Physiol. 96:104-109.
4. Anonymous. 1992. MON 13900 Safener. Technical Data Sheet. St. Louis, MO: Monsanto. 2 p.
5. Barrett, M. 1995. Metabolism of herbicides by cytochrome P450 in corn. Drug Metab. Drug Interact. 12:299-315.
6. Barrett, M., N. Polge, R. Baerg, L. Bradshaw, and C. Poneleit. 1997. Role of cytochrome P450 in herbicide metabolism and selectivity and multiple herbicide metabolizing cytochrome P450 activities in maize. Pages 35-50 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
7. Blake-Kalff, M.M.A., R. A. Randaqll, and J.O.D. Coleman. 1997. Compartmentation of detoxified xenobiotics in plant cells. Pages 245-259 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
8. Bolwell, G. P., K. Bozak, and A. Zimmerlin. 1994. Plant cytochrome P450. Phytochemistry 37:1491-1506.
9. Bordas, B., T. Kömives, Z. Szanto, and A. Lopata. 2000. Comparative three-dimensional quantitative structure-activity relationship study of safeners and herbicides. J. Agric. Food Chem. 48:926-931.
10. Brazier, M., D. Cole, and R. Edwards. 2002. O-Glucosyltransferase activities involved in herbicide metabolism in wheat. Abstr. Weed Sci. Soc. Am. 42:29-30.
11. Breaux, E. J. 1987. Initial metabolism of acetochlor in tolerant and susceptible species. Weed Sci. 35:463-468.
12. Breaux, E. J., M. A. Hoobler, J. E. Patanella, and C. A. Leyes. 1989. Mechanisms of action of thiazole safeners. Pages 163-175 in K. K. Hatzios and R. E. Hoagland, eds. Crop Safeners for Herbicides: Development, Uses, and Mechanisms of Action. San Diego, CA: Academic.
13. Breaux, E. J., J. E. Patanella, and E. F. Sanders. 1987. Chloroacetanilide herbicide selectivity: analyses of glutathione and homoglutathione in tolerant, susceptible, and safened seedlings. J. Agric. Food Chem. 35: 474-478.
14. Brown, H. M., L. B. Brattsten, D. E. Lilly, and P. J. Hanna. 1993. Metabolic pathways and residue levels of thifensulfuron methyl in soybeans. J. Agric. Food Chem. 41:1724-1730.
15. Brown, H. M., M. M. Joshi, A. T. Van, T. H. Carski, J. J. Dulka, M. C. Patrick, R. W. Reister, R. S. Livingston, and J. Doughty. 1997. Degradation of thifensulfuron methyl in soil: role of microbial carboxylesterase activity. J. Agric. Food Chem. 45:955-961.
16. Brown, H. M., V. A. Wittenbach, D. R. Forney, and S. D. Strachan. 1990. Basis for soybean tolerance to thifensulfuron methyl. Pestic. Biochem. Physiol. 37:303-313.
17. Carringer, R. D., C. E. Rieck, and L. P. Bush. 1978. Effects of R-25788 on EPTC metabolism in corn (Zea mays). Weed Sci. 26:167-171.
18. Cole, D. J. 1994. Detoxification and activation of agrochemicals in plants. Pestic. Sci. 42:209-222.
19. Cole, D. J., I. Cummins, P. J. Hatton, D. Dixon, and R. Edwards. 1997. Glutathione transferases in crops and weeds. Pages 139-154 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
20. Cole, D. J. and R. Edwards. 2000. Secondary metabolism of agrochemicals in plants. Pages 107-154 in T. Roberts, ed. Metabolism of Agrochemicals in Plants. Chicester, U.K.: Wiley.
21. Dangl, J. L. and J.D.G. Jones. 2001. Plant pathogens and integrated defense responses to infection. Nature 411:826-833.
22. Davies, J. and J. C. Caseley. 1999. Herbicide safeners: a review. Pestic. Sci. 55:1043-1058.
23. Deng, F. and K. K. Hatzios. 2002a. Purification and characterization of two glutathione S-transferase isozymes from indica-type rice involved in herbicide detoxification. Pestic. Biochem. Physiol. 72:10-23.
24. Deng, F. and K. K. Hatzios. 2002b. Characterization and safener-induction of multiple glutathione S-transferases in three genetic lines of rice. Pestic. Biochem. Physiol. 72:24-39.
25. De Veylder, L., M. Montagu, and D. Inze. 1997. Herbicide-safener inducible gene expression in Arabidopsis thaliana. Plant Cell Physiol. 38: 568-577.
26. Dixon, D. A., D. J. Cole, and R. Edwards. 1998a. Purification, regulation and cloning of a glutathione transferase (GST) from maize resembling the auxin-inducible type-III GSTs. Plant Mol. Biol. 36:75-87.
27. Dixon, D. A., J. Cummins, D. J. Cole, and R. Edwards. 1998b. Glutathione-mediated degradation systems in plants. Curr. Opin. Plant Biol. 1:258-270.
28. Droog, F. 1997. Plant glutathione S-transferase, a tale of theta and tau. J. Plant Growth Regul. 16:95-107.
29. Dubelman, A. M., T. R. Solsten, H. Fujiwara, and A. Mehresheikh. 1997. Metabolism of halosulfuron-methyl by corn and wheat. J. Agric. Food Chem. 45:2314-2321.
30. Durst, F., I. Benveniste, A. Lesot, J.-P. Salaun, and D.-P. Reichhart. 1997. Induction of plant cytochrome P450. Pages 19-34 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
31. Durst, F. and D. R. Nelson. 1995. Diversity and evolution of plant P450 and P450 reductases. Drug Metab. Drug Interact. 12:189-206.
32. Durst, F. and D. P. O'Keefe. 1995. Plant cytochromes P450: an overview. Drug Metab. Drug Interact. 12:171-188.
33. Evans, I. J. and A. J. Greenland. 1998. Transgenic approaches to disease protection: applications of antifungal proteins. Pestic. Sci. 54:353-359.
34. Farago, S. and C. Brunold. 1990. Regulation of assimilatory sulfate reduction by herbicide antidotes. Plant Physiol. 94:1808-1812.
35. Farago, S. and C. Brunold. 1993. Regulation of thiol contents in maize roots by intermediates and effectors of glutathione synthesis. J. Plant Physiol. 144:433-437.
36. Farago, S., C. Brunold, and K. Kreuz. 1994. Herbicide safeners and glutathione metabolism. Physiol. Plant. 91:537-542.
37. Frear, D. S. 1995. Wheat microsomal cytochrome P450 monooxygenases: characterization and importance in the metabolic detoxification and selectivity of wheat herbicides. Drug Metab. Drug Interact. 12:329-357.
38. Frear, D. S. and G. G. Still. 1968. The metabolism of 3,4-dichloropropionanilide in plants. Partial purification and properties of an aryl acylamidase from rice. Phytochemistry 7:913-920.
39. Frova, C., M. Sari Gorla, M. E. Pe, A. Greenland, I. Jepson, and L. Rossini. 1997. Role of the different GST isozymes of maize in herbicide tolerance: genetic and biochemical analysis. Pages 171-181 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
40. Gaillard, F., A. Dufaud, R. Tommasini, K. Kreuz, N. Amhrein, and E. Martinoia. 1994. A herbicide antidote (safener) induces the activity of both the herbicide detoxifying enzyme and of a vacuolar transporter for the detoxified herbicide. FEBS Lett. 352:219-221.
41. Glazebrook, J. 2001. Genes controlling expression of defense responses in Arabidopsis. 2001 status. Curr. Opin. Plant Biol. 13:1983-1986.
42. Gronwald, J. W. 1989. Influence of herbicide safeners on herbicide metabolism. Pages 103-128 in K. K. Hatzios and R. E. Hoagland, eds. Crop Safeners for Herbicides: Development, Uses, and Mechanisms of Action. San Diego, CA: Academic.
43. Gronwald, J. W. and K. L. Plaisance. 1998. Isolation and characterization of glutathione S-transferase isozymes from sorghum. Plant Physiol. 117:877-892.
44. Hall, J. C., R. E. Hoagland, and R. M. Zablotowicz. 2001. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergencies. ACS Symposium Series 777. Washington, D.C.: American Chemical Society.
45. Hall, J. C. and G. R. Stephenson. 1995. The basis for the synergism and safening action of fenchlorazole-ethyl on the herbicidal activity of fenoxaprop-ethyl: a review. Pages 261-268 in Proceedings of the Brighton Crop Protection Conference-Weeds. Crop Protection Council, Surrey, U.K.
46. Han, S. and K. K. Hatzios. 1991. Effects of the herbicide pretilachlor and the safener fenclorim on glutathione content and glutathione-dependent enzyme activity of rice. Z. Naturforsch. 46c:861-865.
47. Hatzios, K. K. 1983. Herbicide antidotes: development, chemistry and mode of action. Adv. Agron. 36:265-316.
48. Hatzios, K. K. 1991a. An overview of the mechanisms of action of herbicide safeners. Z. Naturforsch. 46c:819-827.
49. Hatzios, K. K. 1991b. Biotransformations of herbicides in higher plants. Pages 141-185 in R. Grover and M. Fich, eds. Environmental Chemistry of Herbicides, Vol. II. Boca Raton, FL: CRC.
50. Hatzios, K. K. 1993. Mode of action of naphthalic anhydride as a maize safener for the fensulfuron-methyl. Pages 1259-1266 in Proceedings of the Brighton Crop Protection Conference-Weeds. Volume 3. BCPC, Loughborough, U.K.
51. Hatzios, K. K., ed. 1997. Regulation of Enzymatic System Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
52. Hatzios, K. K. 2000. Herbicide safeners and synergists. Pages 259-294 in T. Roberts, ed. Metabolism of Agrochemicals in Plants. Chicester, U.K.: Wiley.
53. Hatzios, K. K. 2001. Functions and regulation of plant glutathione S-transferases. Pages 218-239 in J. C. Hall, R. E. Hoagland, and R. M. Zablotowicz, eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergences. ACS Symposium Series 777. Washington, D.C.: American Chemical Society.
54. Hatzios, K. K. and R. E. Hoagland, eds. 1989. Crop Safeners for Herbicides: Development, Uses, and Mechanisms of Action. San Diego, CA: Academic. 404 p.
55. Hershey, H. P. and T. D. Stoner. 1991. Isolation and characterization of cDNA clones for RNA species induced by substituted benzenesulfonamides in corn. Plant Mol. Biol. 17:679-690.
56. Hill, B. D., E. H. Stobbe, and B. L. Jones. 1978. Hydrolysis of benzoylprop-ethyl by a wild oat esterase. Weed Res. 18:669-675.
57. Hirase, K. and W. T. Molin. 2001. Effect of flurazole and other safeners for chloroacetanilide herbicides on cysteine synthase in sorghum roots. Pestic. Biochem. Physiol. 71:116-123.
58. Holton, T. A. and E. C. Cornish. 1995. Genetics and biochemistry of anthocyanin biosynthesis. Plant Cell 7:1071-1083.
59. Incledon, B. J. and J. C. Hall. 1997. Enzymatic deesterification of xenobiotics in plants. Pages 67-82 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
60. Irzyk, G. P. and E. P. Furest. 1997. Characterization and induction of maize glutathione S-transferases involved in herbicide detoxification. Pages 155-170 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
61. Ishikawa, T. 1992. The ATP-dependent glutathione S-conjugate export pump. Trends Biochem. Sci. 17:463-468.
62. Jepson, I., C. J. Andrews, V. Roussel, M. Skipsey, and J. K. Towson. 1999. Transgenic approaches to understanding glutahione S-transferases. Abstr. Weed Sci. Soc. Am. 39:179.
63. Jepson, I., D. C. Holt, V. Roussel, S. Y. Wright, and A. J. Greenland. 1997. Transgenic plant analysis as a tool for the study of maize glutathione S-transferases. Pages 313-323 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
64. Jepson, I., A. Martinez, and J. P. Sweeman. 1998. Chemical-inducible gene expression systems for plants-a review. Pestic. Sci. 54:360-367.
65. Koeppe, M. K. and H. M. Brown. 1995. Sulfonylurea herbicide plant metabolism and crop selectivity. Agro-Food-Ind. Hi-Tech. 6:9-14.
66. Kömives, T., G. Gullner, and Z. Kiraly. 1997. The ascorbate-glutathione cycle and oxidative stresses in plants. Pages 85-96 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
67. Kömives, T. and K. K. Hatzios. 1991. Chemistry and structure-activity relationships of herbicide safeners. Z. Naturforsch. 46c:867-871.
68. Kömives, T., V. A. Kömives, M. Balzazs, and F. Dutka. 1985. Role of glutathione-related enzymes and the mode of action of herbicide antidotes. Pages 1155-1162 in Proceedings of the British Crop Protection Conference-Weeds. BCPC, Loughborough, U.K.
69. Kreuz, K. 1993. Herbicide safeners: recent advances and biochemical aspects of their mode of action. Pages 1249-1258 in Proceedings of the Brighton Crop Protection Conference-Weeds. Volume 3. BCPC, Loughborough, U.K.
70. Kreuz, K., J. Gaudin, J. Stingelin, and E. Ebert. 1991. Metabolism of the aryloxyphenoxypropionate herbicide CGA 184927 in wheat, barley, and maize: differential effects of the safener CGA 185072. Z. Naturforsch. 46c:901-905.
71. Kreuz, K., R. Tommasini, and E. Martinoia. 1996. Old enzymes for a new job: herbicide detoxification in plants. Plant Physiol. 111:349-353.
72. Lamoureux, G. L. and D. G. Rusness. 1989. The role of glutathione and glutathione S-transferases in pesticide metabolism, selectivity and mode of action in plants and insects. Pages 153-196 in D. Dolphin, R. Poulson, and O. Avramovic, eds. Glutathione: Chemical Biochemical and Medical Aspects. New York: Wiley.
73. Lamoureux, G. L. and D. G. Rusness. 1991. The effect of BAS-145138 safener on chlorimuron ethyl metabolism and toxicity in corn. Z. Naturforsch. 46c:882-886.
74. Lamoureux, G. L. and D. G. Rusness. 1993. Glutathione in the metabolism and detoxification of xenobiotics in plants. Pages 221-237 in L. J. De Kok, I. Stulen, H. Rennenberg, C. Brunold, and W. Rauser, eds. Sulfur Nutrition and Assimilation in Higher Plants. Hague, The Netherlands: SPB Academic.
75. Lamoureux, G. L., R. H. Shimabukuro, and D. S. Frear. 1991. Glutathione and glycoside conjugation in herbicide selectivity. Pages 227-261 in J. C. Caseley, G. W. Cussans, and R. K. Atkin, eds. Herbicide Resistance in Weeds and Crops. Oxford, U.K.: Butterworth-Heinemann.
76. Leustek, T. 1998. Molecular genetics of sulfate assimilation in plants. Physiol. Plant. 97:411-419.
77. Li, Z.-S., Y. Zhao, and P. A. Rea. 1995a. Magnesium adenosine 5′ triphosphate-energized transport of glutathione S-conjugates by plant vacuolar membrane vesicles. Plant Physiol. 107:1257-1268.
78. Li, Z.-S., R.-G. Zhen, and P. A. Rea. 1995b. 1-Chloro-2,4-dinitrobenzene- elicited increase in vacuolar glutathione S-conjugate transport activity. Plant Physiol. 109:177-185.
79. Link, G., K. Tiller, and S. Baginsky. 1997. Glutathione, a regulator of chloroplast transcription. Pages 125-137 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
80. Low, P. S. and J. R. Merida. 1996. The oxidative burst in plant defense: function and signal transduction. Physiol. Plant. 96:533-542.
81. Marrs, K. A. 1996. The functions and regulation of glutathione S-transferases in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 47:127-158.
82. Marrs, K. A., M. R. Alfenito, A. M. Lloyd, and V. Walbot. 1995. A glutathione S-transferase involved in vacuolar transfer by the maize gene Bronze-2. Nature 375:397-400.
83. Martinoia, E., E. Grill, R. Tommasini, K. Kreuz, and N. Amhrein. 1993. ATP-dependent glutathione S-conjugate 'export' pump in the vacuolar membrane of plants. Nature 364:247-219.
84. McGonigle, B., S. J. Keelr, S. M. Lau, M. K. Koeppe, and D. P. O'Keefe. 2000. A genomics approach to the comprehensive analysis of the glutathione S-transferase gene family in soybean and maize. Plant Physiol. 124:1105-1110.
85. McGonigle, B., S.-M.C. Lau, and D. P. O'Keefe. 1997. Endogenous reactions and substrate specificity of herbicide metabolizing enzymes. Pages 9-17 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
86. Meister, A. 1995. Glutathione biosynthesis and its inhibition. Methods Enzymol. 252:26-30.
87. Miller, K. D., G. P. Irzyk, and E. P. Fuerst. 1994. Benoxacor treatment increases glutathione S-transferase activity in suspension cultures of Zea mays. Pestic. Biochem. Physiol. 48:123-134.
88. Miller, K. D., G. P. Irzyk, E. P. Fuerst, J. E. McFarland, M. Barringer, S. Cruz, W. J. Eberle, and W. Foery. 1996a. Time course of benoxacor metabolism and identification of benoxacor metabolites isolated from suspension-cultured Zea mays cells 1 hour after treatment. J. Agric. Food Chem. 44:3326-3334.
89. Miller, K. D., G. P. Irzyk, E. P. Fuerst, J. E. McFarland, M. Barringer, S. Cruz, W. J. Eberle, and W. Foery. 1996b. Identification of metabolites of the herbicide safener benoxacor isolated from suspension-cultured Zea mays cells 3 and 24 hours after treatment. J. Agric. Food Chem. 44:3335-3341.
90. Mougin, C. P., M.-F. Corio-Costet, and D. Werck-Reichhart. 2001. Plant and fungal cytochrome P-450s: their role in pesticide transformation. Pages 166-181 in J. C. Hall, R. E. Hoagland, and R. M. Zablotowicz, eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergencies. ACS Symposium Series 777. Washington, D.C.: American Chemical Society.
91. Nicolaus, B., Y. Sato, K. Wakabayashi, and P. Böger. 1997. Activation of proherbicides by glutathione S-transferase. Pages 183-196 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
92. Noctor, G., L. Jouanin, and C. H. Foyer. 1997. The biosynthesis of glutathione explored in transformed plants. Pages 109-124 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
93. Ohkawa, H., N. Siota, H. Inui, M. Sugiura, Y. Yabusake, Y. Ohkawa, and T. Ishige. 1997. Herbicide-resistant tobacco and potato plants expressing mammalian P450 monooxygenases. Pages 307-312 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
94. O'Keefe, D. P., J. M. Tepperman, C. Dean, K. J. Leto, D. L. Erbes, and J. T. Odell. 1994. Plant expression of a bacterial cytochrome P450 that catalyzes activation of a sulfonylurea herbicide. Plant Physiol. 105: 473-482.
95. Pallos, F. and J. E. Casida, eds. 1978. Chemistry and Action of Herbicide Antidotes. New York: Academic.
96. Parker, C. 1983. Herbicide antidotes-a review. Pestic. Sci. 14:40-48.
97. Persans, M. W., J. Wang, and M. A. Schuler. 2001. Characterization of maize cytochrome P450 monooxygenases induced in response to safeners and bacterial pathogens. Plant Physiol. 125:1126-1138.
98. Pflugmacher, S., P. Schröder, and H. Sandermann. 2000. Taxonomic distribution of plant glutathione S-transferases acting on xenobiotics. Phytochemistry 54:267-278.
99. Potter, S., D. E. Moreland, K. Kreuz, and E. Ward. 1995. Induction of cytochrome P450 genes by ethanol in maize. Drug Metab. Drug Interact. 12:317-328.
100. Powles, S. B. and C. Preston. 1995. Herbicide Cross Resistance and Multiple Resistance in Plants. Monograph 2. Basel, Switzerland: Herbicide Resistance Action Committee. 22 p.
101. Ramsey, R.J.L., F. L. Mena, and G. R. Stephenson. 2001. Effects of chemical safeners on herbicide action and metabolism in plants. Pages 310-332 in J. C. Hall, R. E. Hoagland, and R. M. Zablotowicz, eds. Pesticide Biotransformation in Plants and Microorganisms: Similarities and Divergencies. ACS Symposium Series 777. Washington, D.C.: American Chemical Society.
102. Rea, P. A., Z.-S. Li, Y. P. Lu, Y. M. Drozdowicz, and E. Martinoia. 1998. From vacuolar GS-X pumps to multispecific ABC transporters. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49:727-740.
103. Rennenberg, H. and C. Brunold. 1994. Significance of glutathione metabolism in plants under stress. Pages 142-156 in H.-D. Behnke, U. Luttge, K. Esser, J. W. Kadereit, and M. Runge, eds. Progress in Botany, Vol. 5. Berlin, Germany: Springer Verlag.
104. Roberts, T., ed. 2000. Metabolism of Agrochemicals in Plants. Chicester, UK: Wiley.
105. Rushmore, T. H. and C. B. Pickett. 1993. Glutathione S-transferases, structure, regulation and therapeutic implications. J. Biol. Chem. 268: 11475-11478.
106. Sanchez-Fernandez, R., W. Ardiles-Diaz, M. Van Montagu, D. Inze, and M. May. 1998. Cloning and expression analyses of AtMRP4, a novel MRP-like gene from Arabidospsis thaliana. Mol. Gen. Genet. 258: 655-662.
107. Sandermann, H., M. Haas, B. Messner, S. Pflugmacher, P. Schröder, and A. Wetzel. 1997. The role of glucosyl and malonyl conjugation in herbicide selectivity. Pages 231-241 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
108. Schmitz, G. and K. Terres. 1992. Structural and functional analysis of Bz-2 locus of Zea mays: characterization of overlapping transcripts. Mol. Gen. Genet. 233:269-277.
109. Schröder, P. 1997. Fate of glutathione S-conjugates in plants. Pages 233-244 in K. K. Hatzios, ed. Regulation of Enzymatic Systems Detoxifying Xenobiotics in Plants. NATO ASI Series. Dordrecht, The Netherlands: Kluwer.
110. Schuler, M. A. 1996. Plant cytochrome P450 monooxygenases. CRC Crit. Rev. Plant Sci. 15:235-284.
111. Scott-Craig, J. S., J. E. Casida, L. Poduje, and J. D. Walton. 1998. Herbicide safener-binding protein of maize. Plant Physiol. 116:1083-1089.
112. 450 monooxygenase cDNA in yeast and tobacco enhances the metabolism of phenylurea herbicides. Proc. Natl. Acad. Sci. USA 96:1750-1755.
113. Smith, D. R. and J. C. Walker. 1996. Plant protein phosphatases. Annu. Rev. Plant Physiol. Plant Mol. Biol. 47:101-125.
114. Stephenson, G. R., J. J. Bunce, R. I. Makowski, and J. C. Curry. 1978. Structure-activity relationships for S-ethyl N,N-dipropylthiocarbamate (EPTC) antidotes in corn. J. Agric. Food Chem. 26:137-140.
115. Stephenson, G. R. and G. Ezra. 1987. Chemical approaches for improving herbicide selectivity and crop tolerance. Weed Sci. 35(Suppl. 1):24-27.
116. Streber, W. R., U. Kutschka, E. Thomas, and H. D. Pohlenz. 1994. Expression of a bacterial gene in transgenic plants confers resistance to the herbicide phenmedipham. Plant Mol. Biol. 25:977-987.
117. Tal, A., M. L. Romano, G. R. Stephenson, A. L. Schwan, and J. C. Hall. 1993. Glutathione conjugation: a detoxification pathway for fenoxaprop in barley, crabgrass, oat and wheat. Pestic. Biochem. Physiol. 46:190-199.
118. Thenaken, R., P. Levine, L. F. Brisson, R. A. Dixon, and C. J. Lamb. 1995. Function of the oxidative burst in hypersensitive disease resistance. Proc. Natl. Acad. Sci. USA 92:4158-4163.
119. Timmerman, K. P. 1989. Molecular characterization of corn glutathione S-transferase isozymes involved in herbicide detoxification. Physiol. Plant. 77:323-342.
120. Trewanas, A. 2002. Plant cell signal transduction: the emerging phenotype. Plant Cell 14:S3-S4.
121. Walton, J. D. and J. E. Casida. 1995. Specific binding of a dichloroacetamide herbicide safener in maize at a site that also binds thiocarbamate and chloroacetanilide herbicides. Plant Physiol. 109:213-219.
122. Werck-Reichhart, D., A. Hehn, and L. Didierjan. 2000. Cytochrome P450 for engineering herbicide resistance. Trends Pharmacol. Sci. 5:116-123.
123. Wiegand, R. C., D. M. Shah, T. J. Mozer, E. I. Harding, J. Diaz-Collier, C. Saunders, E. G. Jaworski, and D. C. Tiemeeier. 1986. Messeneger RNA encoding a glutathione S-transferase responsible for herbicide tolerance in maize is induced in response to safener treatment. Plant Mol. Biol. 7:235-243.
124. Wu, J., C. L. Cramer, and K. K. Hatzios. 1999. Characterization of two cDNAs encoding glutathione S-transferases in rice and induction of their transcripts by the herbicide safener fenclorim. Physiol. Plant. 105:102-108.
125. Yaacoby, T., J. C. Hall, and G. R. Stephenson. 1991. Influence of fenchlorazole-ethyl on the metabolism of fenoxaprop-ethyl in wheat, barley, and crabgrass. Pectic. Biochem. Physiol. 41:296-304.
126. Yenne, S. P. and K. J. Hatzios. 1990a. Influence of oxime ether safeners on glutathione levels and glutathione-related enzyme activity in seeds and seedlings of grain sorghum. Z. Naturforsch. 45c:91-106.
127. Yenne, S. P. and K. K. Hatzios. 1990b. Molecular comparisons of selected herbicides and their safeners by computer-assisted molecular modeling. J. Agric. Food Chem. 38:1950-1956.
128. Zentl, R., J. Schell, and K. Palme. 1994. Photoaffinity labeling of Arabidopsis thaliana plasma membrane vesicles by 5-azido-[7-3h] indole-3-acetic acid: identification of a glutathione S-transferase. Proc. Natl. Acad. Sci. USA 91:690-693.
129. Zhang, B. and K. B. Singh. 1994. ocs-Element promoter sequences are activated by auxin and salicylic acid in Arabidopsis. Proc. Natl. Acad. Sci. USA 91:2507-2511.
130. Zhang, J., A. S. Hamill, and S. E. Weaver. 1995. Antagonism and synergism between herbicides: trends from previous studies. Weed Technol. 9:86-90.
131. Zimmerlin, A. and F. Durst. 1992. Aryl hydroxylation of the herbicide diclofop by a wheat cytochrome P450 monooxygenase: substrate specificity and physiological activity. Plant Physiol. 100:874-881.