Plant Uptake and Metabolism of Triazine Herbicides

The Triazine Herbicides

Volumn , Issue , 2008, Pages 73-99

  Simoneaux, Bruce J ^a   Gould, Thomas J ^b  

^a Agricultural Consultant   (United States)

^b BAYER CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84865228504     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-044451167-6.50010-6     Document Type: Chapter

References (98)

1. Abusteit E.O. Toxicity, Absorption, Translocation and Metabolism in Diploid and Tetraploid Soybean [Glycine max (L.) Merr.] Plants and Cell Cultures (Dissertation) 1983, 103. North Carolina State University, Raleigh, NC.
2. Abusteit E.O., Corbin F.T., Schmitt D.P., Burton J.W., Worsham A.D., Thompson L. Absorption, translocation, and metabolism of metribuzin in diploid and tetraploid soybean ( Glycine max) plants and cell cultures. Weed Sci. 1985, 33:618-628.
3. Beynon K.I., Stoydin G., Wright A.N. A comparison of the breakdown of the triazine herbicides cyanazine, atrazine and simazine in soils and in maize. Pestic. Biochem. Physiol. 1972, 2:153-161.
4. Beynon K.I., Stoydin G., Wright A.N. The breakdown of the triazine herbicide cyanazine in soils and maize. Pestic. Sci. 1972, 3:293-305.
5. Beynon K.I., Stoydin G., Wright A.N. The breakdown of the triazine herbicide cyanazine in wheat and potatoes grown under indoor conditions in treated soils. Pestic. Sci. 1972, 3:379-387.
6. 14C-Simazine: Nature of the Residues in Citrus 1994, Submitted to USEPA.
7. 1.
8. Castelfranco P., Foy C.L., Deutsch D.B. Nonenzymatic detoxification of 2-chloro-4,6-bis(ethylamino)- s-triazine (simazine) by extracts of Zea mays. Weeds 1961, 9:580-591.
9. 2.
10. Collier R.H. Food Quality Protection Act Metabolism Summary 1997, Submitted to USEPA.
11. Davis D.G., Olson P.A., Swanson H.R., Frear D.S. Metabolism of the herbicide metribuzin by an N-glucosyltransferase from tomato cell cultures. Plant Sci. 1991, 74:73-80.
12. 14C-Ametryn in Corn 1990, Submitted to USEPA.
13. 14C-Ametryn in Sugarcane 1990, Submitted to USEPA.
14. Devlin D.L., Gealy D.R., Morrow L.A. Differential metabolism of metribuzin by downy brome ( Bromus tectorum) and winter wheat ( Triticum aestivum). Weed Sci. 1987, 35:741-745.
15. Dodge A.D. The mode of action of herbicides. Progress in Pesticide Biochemistry and Toxicology 1983, Vol. 3:163-197. John Wiley and Sons, New York. D.H. Hutson, T.R. Roberts (Eds.).
16. Esser H.O., Dupuis G., Eber E., Vogel C., Marco G.J. S-triazines. Herbicides: Chemistry, Degradation, and Mode of Action 1975, Vol. 1:129-208. Marcel Dekker, Inc., New York. 2nd edn. P. Kearney, D. Kaufman (Eds.).
17. Falb L.N., Smith A.E. Metribuzin metabolism in soybeans: Characterization of the intraspecific differential tolerance. J. Agric. Food Chem. 1984, 32:1425-1428.
18. Falb L.N., Smith A.E. Metribuzin metabolism in soybeans: Partial characterization of the polar metabolites. Pestic. Biochem. Physiol. 1987, 27:165-172.
19. Fedtke C Leaf peroxisomes deaminate as-triazinone herbicides: Method of detoxification by tolerant plants. Naturwissenschaften 1983, 70:199-200.
20. Fedtke C Selective metabolism of triazinone herbicides. Pest. Sci. 1986, 17:65-66.
21. 2.
22. Fedtke C., Schmidt R.R. Behavior of metribuzin in tolerant and susceptible soybean varieties. Pesticide Chemistry: Human Welfare and Environment 1983, Vol. 3:177-182. Pergamon Press, Oxford. J. Miyamoto, P.C. Kearney (Eds.).
23. 1.
24. Fleischmann T.J., Toth J.C., Simoneaux B. Prometryn-Nature of the Residues: Characterization of Metabolites Present in Field Grown Celery 1990, Submitted to USEPA.
25. Frear D.S., Swanson H.R. Biosynthesis of S-(4-ethylamino-6-isopropylamino-2- s-triazino) glutathione: Partial purification and properties of a glutathione s-transferase from corn. Phytochemistry 1986, 9:2123-2132.
26. 2.
27. 2.
28. Frear D.S., Mansager E.R., Swanson H.R., Tanaka F.S. Metribuzin metabolism in tomato: Isolation and identification of N-glucoside conjugates. Pestic. Biochem. Physiol. 1983, 19:270-281.
29. Frear D.S., Swanson H.R., Mansager E.R. Alternate pathways of metribuzin metabolism in soybean: Formation of N-glucoside and homoglutathione conjugates. Pestic. Biochem. Physiol. 1985.
30. Gawronski S.W., Haderlie L.C., Callihan R.H., Dwelle R.B. Metribuzin absorption, translocation, and distribution in two potato ( Solarium tuberosum) cultivars. Weed Sci. 1985, 33:629-634.
31. Gawronski S.W., Haderlie L.C., Callihan R.H., Gawronska H. Mechanism of metribuzin tolerance: Herbicide metabolism as a basis for tolerance in potatoes. Weed Res. 1986, 26:307-314.
32. Gawronski S.W., Haderlie L.C., Stark J.C. Metribuzin metabolism as the basis for tolerance in barley ( Hordeum vulgare L.). Weed Res. 1987, 27:49-55.
33. 2.
34. Hamilton R.H. Tolerance of several grass species to 2-chloro- s-triazine herbicides in relation to degradation and content of ben-zoxazinone derivatives. J. Agric. Food Chem. 1964, 12:14-17.
35. Hargroder T.G., Rogers R.L. Behavior and fate of metribuzin in soybean and hemp sesbania. Weed Sci. 1974, 22:238-245.
36. 1.
37. Hilton H.W., Nomura N.S., Yauger W.L., Kameda S.S. Absorption, translocation, and metabolism of metribuzin (BAY- 94337) in sugarcane. J. Agric. Food Chem. 1974, 22:578-582.
38. Hilton H.W., Nomura N.S., Kameda S.S., Yauger W.L. Some patterns of herbicide and growth regulator intake, persistence, and distribution in sugarcane. Arch. Environ. Contam. Toxicol. 1976, 4:385-394.
39. Holt R.F. Determination of hexazinone and metabolite residues using nitrogen-selective gas chromatography. J. Agric. Food Chem. 1981, 29:165-172.
40. Kearney P.C., Kaufman D.D., Sheets T.J. Metabolites of simazine by Aspergillus fumigatus. J. Agric. Food Chem. 1965, 13:369-372.
41. 1.
42. 1.
43. 1.
44. Kern A.D., Meggitt W.F., Penner D. Uptake, movement, and metabolism of cyanazine in fall panicum, green foxtail, and corn. Weed Sci. 1975, 23:277-282.
45. Kern A.D., Meggitt W.F., Penner D. Cyanazine metabolism in corn, fall panicum, and green foxtail. Weed Res. 1976, 16:119-124.
46. Knuesli E., Berrer D., Dupuis G., Esser H.O. s-Triazines. Degradation of Herbicides 1969, 51-78. Marcel Dekker, Inc., New York. 1st edn. P. Kearney, D. Kaufman (Eds.).
47. Lamoureux G.L., Shimabukuro R.H., Swanson H.R., Frear D.S. Metabolism of 2-chloro-4-ethylamino-6-isopropylamino- s- triazine (atrazine) in excised sorghum leaf sections. J. Agric. Food Chem. 1970, 18:81-86.
48. Lamoureux G.L., Stafford L.E., Shimabukuro R.H. Conjugation of 2-chloro-4,6-bis(alkylamino)- s-triazines in higher plants. J. Agric. Food Chem. 1972, 20:1004-1010.
49. Lamoureux G.L., Stafford L.E., Shimabukuro R.H., Zaylskie R.G. Atrazine metabolism in sorghum: Catabolism of the glutathione conjugate of atrazine. J. Agric. Food Chem. 1973, 21:1020-1030.
50. Lamoureux G.L., Simoneaux B., Larson J. The metabolism of atrazine and related 2-chloro-4,6-bis(alkylamino)- s-triazines in plants (Chapter 6). Triazine Herbicides: Risk Assessment 1998, 60-81. American Chemical Society, Washington, D.C, Symp. Series 683. L.G. Ballantine, J.E. McFarland, D.S. Hackett (Eds.).
51. 14C-Atrazine: Nature of the Residue in Sugarcane 1993, Submitted to USEPA.
52. 14C-Simazine: Nature of the Residue in Corn 1994, Submitted to USEPA.
53. 14C-Simazine: Nature of the Residue in Apples 1994, Submitted to USEPA.
54. 14C-Simazine: Nature of the Residue in Grapes 1994, Submitted to USEPA.
55. 14C-Atrazine: Nature of the Residue in Corn and Sorghum 1992, Submitted to USEPA.
56. 14C-Atrazine: Nature of the Residue in Sugarcane 1993, Supplement No. 1 to the final report. Submitted to USEPA.
57. 14C-Atrazine: Nature of the Residue in Corn and Sorghum 1994, Amendment No. 2 to the final report. Submitted to USEPA.
58. 14C-SENCOR in Soybeans 1987, Miles Ag. Div. Report Number 94593.
59. Mangeot B.L., Slife F.E., Rieck C.E. Differential metabolism of metribuzin by two soybean ( Glycine max) cultivars. Weed Sci. 1979, 27:267-269.
60. Maun M.A., McLeod W.J. Absorption and metabolism of metribuzin in barnyard grass and American nightshade. Can. J. Plant Sci. 1978, 58:485-492.
61. Montgomery M.L., Freed V.H. Metabolism of triazine herbicides by plants. J. Agric. Food Chem. 1964, 12:11-14.
62. Montgomery M.L., Botsford D.L., Freed V.H. Metabolism of hydroxysimazine by corn plants. J. Agric. Food Chem. 1969, 17:1241-1243.
63. Morgan J.G. Preliminary Studies on the Metabolism of SENCOR in Tomatoes 1972, Miles Ag. Div. Report Number 35013.
64. Morgan J.G. Metabolism of SENCOR in Tomatoes 1973, Miles Ag. Div. Report Number 35969.
65. Morgan J.G. The Metabolism of SENCOR in Seedling Potatoes 1974, Miles Ag. Div. Report Number 40564.
66. Morgan J.G., Lenz C.S. Characterization of Metribuzin Metabolites in Wheat Grain Aqueous Phase 1992, Miles Ag. Div. Report Number 94592-1.
67. Naylor A.W. Herbicide metabolism in plants. Herbicides: Physiology, Biochemistry, Ecology 1976, Academic Press, New York. 2nd edn. L.J. Audus (Ed.).
68. Orr G.R., Simoneaux B.J., Sobralske M.V., Fleischmann T.J. Disposition of Prometon in the Rat 1991, ABR-91040.
69. Oswald T.H., Smith A.E., Phillips D.V. Phytotoxicity and detoxification of metribuzin in dark-grown suspension cultures of soybean. Pestic. Biochem. Physiol. 1978, 8:73-83.
70. 14C (SENCOR) in potatoes, carrots, and soil under outdoor conditions. Chemosphere 1976, 5:137-144.
71. Reiser R.W., Belasco I.J., Rhodes R.C. Identification of metabolites of hexazinone by mass spectrometry. Biomed. Mass Spectrom. 1983, 10:581-585.
72. 2.
73. Roth W Comparative study of the reaction of simazine, a herbicide, on maize and wheat. Compt. Rend. 1957, 245:942-944.
74. Saeman M.C. Chemical and Metabolic Oxidation of the Herbicide Metribuzin [Dissertation] 1984, 94. University of California, Berkeley, CA.
75. Saeman M.C., Casida J.E. Metribuzin metabolites in mammals and liver microsomal oxidase systems: Identification, synthesis, and reactions. J. Agric. Food Chem. 1984, 32:749-755.
76. Saeman M.C., Smith M.T., Casida J.E. Metabolism and toxicity of metribuzin in mouse liver. Pestic. Biochem. Physiol. 1985, 23:123-130.
77. Sanson D. Prometryn: Characterization of Metabolites Present in Field Grown Celery 1992, Supplement to final report. Submitted to USEPA.
78. 14C-Prometryn: Uptake and Metabolism in Greenhouse Grown Cotton 1994, Submitted to USEPA.
79. 2.
80. 2.
81. Schumacher R.W. Metabolism of Metribuzin in Soybeans and Soil [Dissertation] 1974, 91. University of Kentucky, Lexington, KY.
82. Shimabukuro R.H. Significance of atrazine dealkylation in root and shoot of pea plants. J. Agric. Food Chem. 1967, 15:557-562.
83. Shimabukuro R.H. Atrazine metabolism and herbicidal selectivity. Plant Physiol. 1967, 42:1269-1276.
84. Shimabukuro R.H. Atrazine metabolism in resistant corn and sorghum. Plant Physiol. 1968, 43:1925-1930.
85. Shimabukuro R.H., Swanson H.R Atrazine metabolism, selectivity, and mode of action. J. Agric. Food Chem. 1969, 17:199-205.
86. Shimabukuro R.H., Kadunce R.E., Frear D.S. Dealkylation of atrazine in mature pea plants. J. Agric. Food Chem. 1966, 14:392-395.
87. Shimabukuro R.H., Swanson H.R., Walsh W.C. Atrazine detoxification mechanism in corn. Plant Physiol. 1970, 46:103-107.
88. Shimabukuro R.H., Lamoureux G.L., Frear D.S., Bakke J.E. Metabolism of s-triazines and its significance in biological systems. Pesticide Terminal Residues 1971, 323-342. Butterworths, London, England. A.S. Tahori (Ed.).
89. Shimabukuro R.H., Frear D.S., Swanson S.H.R., Walsh W.C. Glutathione conjugation: An enzymatic basis for atrazine resistance in corn. Plant Physiol. 1971, 47:10-14.
90. Shimabukuro R.H., Walsh W.C., Lamoureux G.L., Stafford L.E. Atrazine metabolism in sorghum: Chloroform-soluble intermediates in the N-dealkylation and glutathione conjugation pathways. J. Agric. Food Chem. 1973, 21:1031-1036.
91. 14C-GS-13529 in Field and Greenhouse Sorghum and Soil 1972, GAAC-72045.
92. Smith A.E., Wilkinson R.E. Differential absorption, translocation and metabolism of metribuzin [4-amino-6-tert-butyl-3- (methylthio)- as-triazine-5(4H)one] by soybean cultivars. Physiol. Plant. 1974, 32:253-257.
93. Smith A.E., Phatak S.C., Emmatty D.A. Metribuzin metabolism by tomato cultivars with low, medium, and high levels of tolerance to metribuzin. Pestic. Biochem. Physiol. 1989, 35:284-290.
94. 2.
95. Stephenson G.R., McLeod J.E., Phatak S.C. Differential tolerance of tomato cultivars to metribuzin. Weed Sci. 1976, 24:161-165.
96. 1.
97. 14C-Ametryn: Nature of the Residue in Banana 1996, Submitted to USEPA.
98. Wahlroos O., Virtanen A.I. The precursors of 6-methoxy-benzoxazolinone in maize and wheat plants, their isolation and some of their properties. Acta Chem. Scand. 1959, 13:1906-1908.