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Mechanisms of Herbicide Absorption Across Plant Membranes and Accumulation in Plant Cells

Published online by Cambridge University Press:  12 June 2017

Tracy M. Sterling*
Affiliation:
Dep. Entomol., Plant Pathol. and Weed Sci., New Mexico State Univ., Las Cruces, NM 88003

Abstract

In most cases, a herbicide must traverse the cell wall, the plasma membrane, and organellar membranes of a plant cell to reach its site of action where accumulation causes phytotoxicity. The physicochemical characteristics of the herbicide molecule including lipophilicity and acidity, the plant cell membranes, and the electrochemical potential in the plant cell control herbicide absorption and accumulation. Most herbicides move across plant membranes via nonfacilitated diffusion because the membrane's lipid bilayer is permeable to neutral, lipophilic xenobiotics. Passive absorption of lipophilic, ionic herbicides or weak acids can be mediated by an ion-trapping mechanism where the less lipophilic, anionic form accumulates in alkaline compartments of the plant cell. A model that includes the pH and electrical gradients across plant cell membranes better predicts accumulation concentrations in plant cells of weak acid herbicides compared to a model that uses pH only. Herbicides also may accumulate in plant cells by conversion to nonphytotoxic metabolites, binding to cellular constituents, or partitioning into lipids. Evidence exists for herbicide transport across cell membranes via carrier-mediated processes where herbicide accumulation is energy dependent; absorption is saturable and slowed by metabolic inhibitors and compounds of similar structure.

Type
Special Topics
Copyright
Copyright © 1994 by the Weed Science Society of America 

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References

Literature Cited

1. Balke, N. E. and Price, T. P. 1988. Relationship of lipophilicity to influx and efflux of triazine herbicides in oat roots. Pestic. Biochem. Physiol. 30:228237.Google Scholar
2. Barak, E., Dinoor, A., and Jacoby, B. 1983. Adsorption of systemic fungicides and a herbicide by some components of plant tissues, in relation to some physicochemical properties of the pesticides. Pestic. Sci. 14:213219.Google Scholar
3. Barrett, M. and Ashton, F. M. 1983. Napropamide fluxes in corn (Zea mays) root tissue. Weed Sci. 31:4348.CrossRefGoogle Scholar
4. Baur, J. R. and Bovey, R. W. 1970. The uptake of picloram by potato tuber tissue. Weed Sci. 18:2224.CrossRefGoogle Scholar
5. Baur, J. R., Bovey, R. W., Baker, R. D., and Riley, I. 1971. Absorption and penetration of picloram and 2,4,5-T into detached live oak leaves. Weed Sci. 19:138141.Google Scholar
6. Boulware, M. A. and Camper, N. D. 1973. Sorption of some 14C-herbicides by isolated plant cells and protoplasts. Weed Sci. 21:145149.Google Scholar
7. Brecke, B. J. and Duke, W. B. 1980. Effect of glyphosate on intact bean plants (Phaseolus vulgaris L.) and isolated cells. Plant Physiol. 66:656659.Google Scholar
8. Briggs, G. G., Bromilow, R. H., and Evans, A. A. 1982. Relationships between lipophilicity and root uptake and translocation of non-ionised chemicals by barley. Pestic. Sci. 13:495504.CrossRefGoogle Scholar
9. Briggs, G. G., Rigitano, R. L. O., and Bromilow, R. H. 1987. Physicochemical factors affecting uptake by roots and translocation to shoots of weak acids in barley. Pestic. Sci. 19:101112.Google Scholar
10. Briskin, D. P. 1994. Membranes and transport systems in plants: An overview. Weed Sci. 42:255262.CrossRefGoogle Scholar
11. Bromilow, R. H. and Chamberlain, K. 1991. Pathways and mechanisms of transport of herbicides in plants. Pages 245284 in Kirkwood, R. C., ed. Target Sites for Herbicide Action. Topics in Applied Chemistry (Katritzky, A. R. and Sabongi, G. J., series eds.) Plenum Press, New York.CrossRefGoogle Scholar
12. Bromilow, R. H., Chamberlain, K., and Evans, A. A. 1990. Physicochemical aspects of phloem translocation of herbicides. Weed Sci. 38:305314.Google Scholar
13. Buman, R. A., Gealy, D. R., and Fuerst, E. P. 1992. Relationship between temperature and triazinone herbicide activity II. Herbicide absorption by protoplasts and herbicide inhibition of photosynthetic electron transport in thylakoids. Pestic. Biochem. Physiol. 43:2936.Google Scholar
14. Burton, J. D. and Balke, N. E. 1987. Carrier-mediated transport of glyphosate into plant cells. WSSA Abstr. 27:69.Google Scholar
15. Burton, J. D. and Balke, N. E. 1988. Glyphosate uptake by suspension-cultured potato (Solanum tuberosum and S. brevidens) cells. Weed Sci. 36:146153.Google Scholar
16. Collander, R. 1949. The permeability of plant protoplasts to small molecules. Physiol. Plant. 2:300311.CrossRefGoogle Scholar
17. Couderchet, M. and Retzlaff, G. 1990. Bentazone-sethoxydim antagonism: the role of ATP and plasma membrane ATPase. Pestic. Sci. 30:430433.Google Scholar
18. Couderchet, M. and Retzlaff, G. 1991. The role of the plasma membrane ATPase in bentazone-sethoxydim antagonism. Pestic. Sci. 32:295306.CrossRefGoogle Scholar
19. Darmstadt, G. L., Balke, N. E., and Schrader, L. E. 1983. Use of corn root protoplasts in herbicide absorption studies. Pestic. Biochem. Physiol. 19:172183.CrossRefGoogle Scholar
20. Darmstadt, G. L., Balke, N. E., and Price, T. P. 1984. Triazine absorption by excised corn root tissue and isolated corn root protoplasts. Pestic. Biochem. Physiol. 21:1021.Google Scholar
21. Davis, F. S., Villarreal, A., Baur, J. R., and Goldstein, I. S. 1972. Herbicidal concentrations of picloram in cell culture and leaf buds. Weed Sci. 20:185188.Google Scholar
22. Denis, M.-H. and Delrot, S. 1993. Carrier-mediated uptake of glyphosate in broad bean (Vicia faba) via a phosphate transporter. Physiol. Plant. 87:569575.Google Scholar
23. Devine, M. D. 1989. Phloem translocation of herbicides. Rev. Weed Sci. 4:191213.Google Scholar
24. Devine, M. D., Bestman, H. D., and Vanden Born, W. H. 1987. Uptake and accumulation of the herbicides chlorsulfuron and clopyralid in excised pea root tissue. Plant Physiol. 85:8286.Google Scholar
25. Devine, M. D. and Vanden Born, W. H. 1991. Absorption and transport in plants. Pages 119140 in Grover, R. and Cessna, A. J., eds. Environmental Chemistry of Herbicides. Vol. 2. CRC Press, Inc., Boca Raton, FL.Google Scholar
26. Donaldson, T. W., Bayer, D. E., and Leonard, O. A. 1973. Absorption of 2,4-dichlorophenoxyacetic acid and 3-(p-chlorophenyl)-1,1-dimethylurea (monuron) by barley roots. Plant Physiol. 52:638645.Google Scholar
27. El Ibaoui, H., Delrot, S., Besson, J., and Bonnemain, J. 1986. Uptake and release of a phloem-mobile (glyphosate) and of a non-phloem-mobile (iprodione) xenobiotic by broadbean leaf tissues. Physiol. Veg. 24:431442.Google Scholar
28. Fitzgibbon, J. and Braymer, H. D. 1988. Phosphate starvation induces uptake of glyphosate by Pseudomonas sp. strain PG2982. Appl. Environ. Microbiol. 54:18861888.Google Scholar
29. Goldsmith, M. H. M. and Goldsmith, T. H. 1981. Quantitative predictions for the chemiosmotic uptake of auxin. Planta 153:2533.Google Scholar
30. Gougler, J. A. and Geiger, D. R. 1981. Uptake and distribution of N-phos-phonomethylglycine in sugar beet plants. Plant Physiol. 68:668672.Google Scholar
31. Grimm, E., Neumann, S., and Jacob, F. 1983. Uptake of sucrose and xenobiotics into conducting tissue of cyclamen. Biochem. Physiol. Pflanz. 178:2942.Google Scholar
32. Grimm, E., Neumann, S., and Jacob, F. 1985. Transport of xenobiotics in higher plants, II. Absorption of defenuron, carboxyphenylmethylurea, and maleic hydrazide by isolated conducting tissue of cyclamen. Biochem. Physiol. Pflanz. 180:383392.Google Scholar
33. Grimm, E., Neumann, S., and Krug, B. 1987. Transport of xenobiotics in higher plants, IV. Ambimobility of the acidic compounds bromoxynil and pentachlorophenol. Biochem. Physiol. Pflanz. 182:323332.CrossRefGoogle Scholar
34. Gronwald, J. W., Jourdan, S. W., Wyse, D. L., Somers, D. A., and Magnusson, M. U. 1993. Effect of ammonium sulfate on absorption of imazethapyr by quackgrass (Elytrigia repens) and maize (Zea mays) cell suspension cultures. Weed Sci. 41:325334.Google Scholar
35. Gutknecht, J. and Walter, A. 1980. Transport of auxin (indoleacetic acid) through lipid bilayer membranes. J. Membrane Biol. 56:6572.Google Scholar
36. Haderlie, L. C., Widholm, J. M., and Slife, F. W. 1977. Effect of glyphosate on carrot and tobacco cells. Plant Physiol. 60:4043.Google Scholar
37. Hart, J. J., DiTomaso, J. M., Linscott, D. L., and Kochian, L. V. 1992. Transport interactions between paraquat and polyamines in roots of intact maize seedlings. Plant Physiol. 99:14001405.Google Scholar
38. Hatzios, K. K. 1991. Biotransformations of herbicides in higher plants. Pages 141185 in Grover, R. and Cessna, A. J., eds. Environmental Chemistry of Herbicides. Vol. II. CRC Press, Inc., Boca Raton, FL.Google Scholar
39. Hawkes, T. R. 1989. Studies of herbicides which inhibit branched chain amino acid biosynthesis. Pages 131138 in Copping, L. G., Dalziel, J. and Dodge, A. D., eds. Prospects for amino acid biosynthesis inhibitors in crop protection and pharmaceutical chemistry. Proc. Br. Crop Prot. Counc., Monogr. No. 42.Google Scholar
40. Hess, F. D. 1985. Herbicide absorption and translocation and their relationship to plant tolerances and susceptibility. Pages 191214 in Duke, S. O., ed. Weed Physiology. Vol. 2. Herbicide Physiology. CRC Press, Inc., Boca Raton, FL.Google Scholar
41. Hoppe, H. H. and Zacher, H. 1985. Inhibition of fatty acid biosynthesis in isolated bean and maize chloroplasts by herbicidal phenoxy-phenoxypropionic acid derivatives and structurally-related compounds. Pestic. Biochem. Physiol. 24:298305.CrossRefGoogle Scholar
42. Irzyk, G. P., Bauman, T. T., and Carpita, N. C. 1990. Uptake, metabolism, and activity of haloxyfop in liquid cultures of proso millet (Panicum miliaceum L. cv Abarr). Weed Sci. 38:484491.Google Scholar
43. Isensee, A. R., Jones, G. E., and Turner, B. C. 1971. Root absorption and translocation of picloram by oats and soybeans. Weed Sci. 19:727731.Google Scholar
44. Johnson, M. P. and Bonner, J. 1956. The uptake of auxin by plant tissue. Physiol. Plant. 9:102118.Google Scholar
45. Kasai, F. and Bayer, D. E. 1991a. Quantitative evaluation of the weak acid hypothesis as the mechanism for 2,4-D absorption by corn root protoplasts. J. Pestic. Sci. 16:163170.Google Scholar
46. Kasai, F. and Bayer, D. E. 1991b. Relationship between intracellular pH and 2,4-D absorption by corn root protoplasts under the influence of metabolic inhibitors and antiauxins. J. Pestic. Sci. 16:171177.Google Scholar
47. Kurkdjian, A. and Guern, J. 1989. Intracellular pH: Measurement and importance in cell activity. Annu. Rev. Plant Physiol. Plant Mol. Biol. 40:271303.Google Scholar
48. Ladner, D. W. 1990. Structure-activity relationships among the imidazolinone herbicides. Pestic. Sci. 29:317333.Google Scholar
49. Lichtner, F. T. 1983. Amitrole absorption by bean (Phaseolus vulgaris L. cv ‘Red Kidney’) roots. Plant Physiol. 71:307312.Google Scholar
50. Liebl, R. A., Zehr, U. B., and Teyker, R. H. 1992. Influence of nitrogen form on extracellular pH and bentazon uptake by cultured soybean (Glycine max) cells. Weed Sci. 40:418423.Google Scholar
51. Little, D. L. 1991. Physicochemical parameters affecting root absorption and translocation of 5′-substituted pyridine imidazolinones. 165 pp. Ph.D. Diss., Rutgers Univ., New Jersey.Google Scholar
52. Little, D. L. and Shaner, D. L. 1991. Absorption and translocation of the imidazolinone herbicides. Pages 5369 in Shaner, D. L. and O'Connor, S. L., eds. The Imidazolinone Herbicides. CRC Press, Boston, MA.Google Scholar
53. McCloskey, W. B. 1991. The absorption of atrazine, 2,4-D and glyphosate by wheat leaf protoplasts. 148 pp. Ph.D. Diss. Univ. of California, Davis.Google Scholar
54. McCloskey, W. B. and Bayer, D. E. 1990. Atrazine absorption and effects on photosynthesis in wheat leaf protoplasts. Pestic. Biochem. Physiol. 37:227238.Google Scholar
55. Mersie, W. and Foy, C. L. 1987. Influence of pH on the absorption of chlorsulfuron by leaves and excised roots of velvetleaf (Abutilon theophrasti). Weed Sci. 35:1114.Google Scholar
56. Mersie, W. and Singh, M. 1987. Comparison of norflurazon absorption by excised roots of three plant species. Pestic. Biochem. Physiol. 28:114120.Google Scholar
57. Mervosh, T. L. and Balke, N. E. 1991. Effects of calcium, magnesium, and phosphate on glyphosate absorption by cultured plant cells. Weed Sci. 39:347353.Google Scholar
58. Minocha, S. C. and Nissen, P. 1985. Uptake of 2,4-dichlorophenoxyacetic acid and indoleacetic acid in tuber slices of Jerusalem artichoke and potato. J. Plant Physiol. 120:351362.Google Scholar
59. Moody, K., Kust, C. A., and Buchholtz, K. P. 1970. Uptake of herbicides by soybean roots in culture solutions. Weed Sci. 18:642647.Google Scholar
60. Morrison, I. N. and Vanden Born, W. H. 1975. Uptake of picloram by roots of alfalfa and barley. Can. J. Bot. 53:17741785.Google Scholar
61. Nandihalli, U. B. and Bhowmik, P. C. 1989. Chlorimuron absorption by excised velvetleaf (Abutilon theophrasti) roots. Weed Sci. 37:2933.Google Scholar
62. Neumann, W., Laasch, H., and Urbach, W. 1987. Mechanisms of herbicide sorption in microalgae and the influence of environmental factors. Pestic. Biochem. Physiol. 27:189200.Google Scholar
63. Nobel, P. S. 1991. Solutes. Pages 109189 in Physicochemical and Environmental Plant Physiology. Academic Press, New York.Google Scholar
64. Nooden, L. D. 1970. Metabolism and binding of 14C-maleic hydrazide. Plant Physiol. 45:4652.Google Scholar
65. Ooka, M. and Balke, N. E. 1991. Cellular uptake of sulfonylurea analogs: a compartmental analysis, WSSA Abstr. 31:67.Google Scholar
66. Orwick, P. L., Schreiber, M. M., and Hodges, T. K. 1976. Absorption and efflux of chloro-s-triazines by Setaria roots. Weed Res. 16:139144.Google Scholar
67. Owen, W. J. and Donzel, B. 1986. Oxidative degradation of chlorotoluron, propiconazole, and metalaxyl in suspension cultures of various crop plants. Pestic. Biochem. Physiol. 26:7589.Google Scholar
68. Peterson, C. A. and Edgington, L. V. 1976. Entry of pesticides into the plant symplast as measured by their loss from an ambient solution. Pestic. Sci. 7:483491.CrossRefGoogle Scholar
69. Pillmoor, J. B. and Roberts, T. R. 1985. Approaches to the study of non-extractable (bound) pesticide residues in plants. Pages 85101 in Hutson, D. H. and Roberts, T. R., eds. Progress in Pesticide Biochemistry and Toxicology. Vol 4. John Wiley and Sons, Ltd. Google Scholar
70. Pipke, R. and Amrhein, N. 1988. Isolation and characterization of a mutant of Arthrobacter sp. strain GLP-1 which utilizes the herbicide glyphosate as its sole source of phosphorus and nitrogen. Appl. Environ. Microbiol. 54:28682870.Google Scholar
71. Pipke, R., Schulz, A., and Amrhein, N. 1987. Uptake of glyphosate by an Arthrobacter sp. Appl. Environ. Microbiol. 53:974978.Google Scholar
72. Prasad, R. and Blackman, G. E. 1965. Studies in the physiological action of 2,2-dichloropropionic acid, III. Factors affecting the level of accumulation and mode of action. J. Exp. Bot. 16:545568.Google Scholar
73. Price, T. P. and Balke, N. E. 1982. Characterization of rapid atrazine absorption by excised velvetleaf (Abutilon theophrasti) roots. Weed Sci. 30:633639.Google Scholar
74. Price, T. P. and Balke, N. E. 1983a. Characterization of atrazine accumulation by excised velvetleaf (Abutilon theophrasti) roots. Weed Sci. 31:1419.Google Scholar
75. Price, T. P. and Balke, N. E. 1983b. Comparison of atrazine absorption by underground tissues of several plant species. Weed Sci. 31:482487.Google Scholar
76. Raven, J. A. 1975. Transport of indoleacetic acid in plant cells in relation to pH and electrical potential gradients, and its significance for polar IAA transport. New Phytol. 74:163172.Google Scholar
77. Reider Van Ellis, M. and Shaner, D. L. 1988. Mechanism of cellular absorption of imidazolinones in soybean (Glycine max) leaf discs. Pestic. Sci. 23:2534.Google Scholar
78. Retzlaff, G., Hilton, J. L., and St. John, J. B. 1979. Inhibition of photosynthesis by bentazon in intact plants and isolated cells in relation to the pH. Z. Naturforsch. 34c:944947.Google Scholar
79. Richard, E. P. Jr. and Slife, F. W. 1979. In vivo and vitro characterization of the foliar entry of glyphosate in hemp dogbane (Apocynum cannabinum). Weed Sci. 27:426433.Google Scholar
80. Riechers, D. E. 1990. Surfactant effects on the plasma membrane as a mode of action in promoting glyphosate phytotoxicity. 47 pp. M.Sc. Diss. Univ. Illinois, Urbana-Champaign.Google Scholar
81. Rubery, P. H. 1977, The specificity of carrier-mediated auxin transport by suspension-cultured crown gall cells. Planta 135:275283.Google Scholar
82. Rubery, P. H. 1978. Hydrogen ion dependence of carrier-mediated auxin uptake by suspension-cultured crown gall cells. Planta 142:203206.Google Scholar
83. Rubery, P. H. 1987. Auxin Transport. Pages 341362 in Davies, P. J., ed. Plant Hormones and Their Role in Plant Growth and Development. Kluwer Academic Publishers, Dordrecht.Google Scholar
84. Sabater, M. and Rubery, P. H. 1987. Auxin carriers in Cucurbita vesicles, III. Specificity, with particular reference to 1-naphthylacetic acid. Planta 171:514518.Google Scholar
85. Scheel, D. and Sandermann, H. Jr. 1981. Metabolism of 2,4-dichlorophenoxyacetic acid in cell suspension cultures of soybean (Glycine max L.) and wheat (Triticum aestivum L.). II Evidence for incorporation into lignin. Planta 152:253258.Google Scholar
86. Sheets, T. J. 1961. Uptake and distribution of simazine by oat and cotton seedlings. Weeds 9:113.Google Scholar
87. Shone, M. G. T. and Wood, A. V. 1974. A comparison of the uptake and translocation of some organic herbicides and a systemic fungicide by barley, I. Absorption in relation to physicochemical properties. J. Exp. Bot. 25:390400.Google Scholar
88. Singer, S. and McDaniel, C. N. 1982. Transport of the herbicide 3-amino-1,2,4-triazole by cultured tobacco cells and leaf protoplasts. Plant Physiol. 69:13821386.Google Scholar
89. Smith, A. E. 1972. Accumulation of (2,4-dichlorophenoxy)acetic acid and (2,4,5-trichlorophenoxy)acetic acid by parenchyma tissue as influenced by metabolic inhibitors and lecithin. Physiol. Plant. 27:338341.Google Scholar
90. Smith, A. E. 1989. Degradation, fate, and persistence of phenoxyalkanoic acid herbicides in soil. Rev. Weed Sci. 4:124.Google Scholar
91. Smith, A. M. and Vanden Born, W. H. 1992. Ammonium sulfate increases efficacy of sethoxydim through increased absorption and translocation. Weed Sci. 40:351358.Google Scholar
92. Sterling, T. M. and Balke, N. E. 1988. Use of soybean (Glycine max) and velvetleaf (Abutilon theophrasti) suspension-cultured cells to study bentazon metabolism. Weed Sci. 36:558565.Google Scholar
93. Sterling, T. M. and Balke, N. E. 1989. Differential bentazon metabolism and retention of bentazon metabolites by plant cell cultures. Pestic. Biochem. Physiol. 34:3948.Google Scholar
94. Sterling, T. M., Balke, N. E., and Silverman, D. S. 1990. Uptake and accumulation of the herbicide bentazon by cultured plant cells. Plant Physiol. 92:11211127.Google Scholar
95. Stoller, E. W. 1969. The kinetics of amiben absorption and metabolism as related to species sensitivity. Plant Physiol. 44:854860.Google Scholar
96. Struve, I., Golle, B., and Luttge, U. 1987. Sethoxydim uptake by leaf slices of sethoxydim resistant and sensitive grasses. Z. Naturforsch. 42c:279282.Google Scholar
97. Swanson, C. R. and Baur, J. R. 1969. Absorption and penetration of picloram in potato tuber discs. Weed Sci. 17:311314.Google Scholar
98. Tritter, S. A., Holl, F. B. and Todd, B. G. 1987. Diclofop-methyl and diclofop uptake in oat (Avena sativa L.) protoplasts. Can. J. Plant Sci. 67:215223.Google Scholar
99. Upadhyaya, M. K. and Nooden, L. D. 1980. Mode of dinitroaniline herbicide action, II. Characterization of [14C]oryzalin uptake and binding. Plant Physiol. 66:10481052.Google Scholar
100. Wedding, R. T. and Erickson, L. C. 1957. The role of pH in the permeability of Chlorella to 2,4-D. Plant Physiol. 32:503512.Google Scholar
101. Whitwell, T., Banks, P., Basler, E., and Santelmann, P. W. 1980. Glyphosate absorption and translocation in bermudagrass (Cynodon dactylon) and activity in horsenettle (Solanum carolinense). Weed Sci. 28:9396.Google Scholar
102. Zsoldos, F. and Haunold, E. 1979. Effects of pH changes on ion and 2,4-D uptake of wheat roots. Physiol. Plant. 47:7780.Google Scholar