Abstract
Among the phenylurea herbicides, chlorotoluron (N’-(3-chloro-4-methylphenyl)N,N-dimethylurea) is one of the most widely used in winter wheat, due to its selectivity (Ryan et al., 1981). This herbicide controls a range of broad-leaf weeds, and is also effective against slender foxtail (Alopecurus myosuroides) and wild oat (Avena fatua) (Ryan and Owen, 1982). The parent compound undergoes rapid metabolism in plants by oxidative Ndemethylation and hydroxylation of the 4-methyl phenyl group, forming a number of derivatives with modified phytotoxicity (Ryan et al., 1981). Chlorotoluron resistance has been commonly correlated to the presence of a detoxifying capability associated with Cyt P-450 monooxygenases. This superfamily encodes several enzyme isoforms which are involved in a number of biosynthetic pathways in plants, including those leading to phenolics, terpenoids, steroids, alkaloids, lignins and hydroxylated fatty acids. The relationship between plant Cyt P-450 and detoxification processes has been established for several crops and herbicides (Mouguin et al., 1990; Fonne-Pfister et al., 1990), this metabolic capability being the basis for the selectivity of chlorotoluron vs. weeds. However, the continuous use of chlorotoluron in monoculture systems has led to the appearance of several chlorotoluronresistant biotypes of various weeds, including Alopecurus myosuroides (Niemans and Pestemer, 1984; Moss and Cussans, 1985; De Prado et al., 1991) and Lolium rigidum (Burnet et al., 1993).
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References
Buhler, D.D., Swisher, B.A. and Burnside, O.C. (1985) Behaviour of 14C-haloxyfop-methyl in intact plants and cell cultures. Weed Science 33: 291–299.
Burnet, M.W.M., Loveys, B.R., Holtum, J.A.M. and Powles, S.B. (1993) A mechanism of chlorotoluron resistance in Lolium rigidum. Planta 190: 182–189.
Canivenc, M.C., Cagnac, B., Cabanne, F. and Scalia, R. (1989) Induced changes of chlorotoluron metabolism in wheat cell suspension cultures. Plant Physiology Biochemistry 27: 193–201.
Chaleff, R.S. and Ray, T.B. (1984) Herbicide-resitant mutants from tobacco cell cultures. Science 223: 1148–1151.
Cole, D.J. and Owen, W.J. (1988) Metabolism of chlorotoluron in cell suspensions of Latuca sativa: a qualitative change with age of culture. Phytochemistry 27: 1709–1711.
Davis, D.G. and Shimabukuro, R.H. (1980) Studies of herbicide toxicity and mode of action using mesophyll cells and callus-derived cell suspensions. Canadian Journal Botany 58: 1482–1489.
De Prado R, Plaisance K, Menendez J, Gronwald J. (1995) Effect of graminicide herbicides on growth and ACCase activity in a chlorotoluron-resistant biotype of Alopecurus myosuroides Huds. In: International Symposium Weed and Crop Resistance to Herbicides (R. De Prado, J. Jorrin, L. garcía-Torres and G. Marshall, eds.), 59–61. University of Córdoba, Córdoba, Spain.
Devine, M.D., Duke, S.O. and Fedtke, C., eds. (1993) Physiology of Herbicide Action, Prentice Hall, Englewood Cliffs, NJ.
Grossman K, Berghaus R, Retzlaff G. (1992) Heterotrophic plant cell suspension cultures for monitoring biological activity in agrochemical research. Comparision with screens using algae, germinating seeds and whole plants. Pesticide Science 35: 283–289.
Jorrin, J., Menendez, J., Romera, E., Tena, M and De Prado, R. (1992) Detoxification of chlorotoluron by Alopecurus myosuroides via conjugation. Mededelingen van de Faculteit Landbouwwetenschappen. Universiteit Gent 57/3B: 1047–1052.
Kemp, M.S., Moss, S.R. and Thomas, T.H. (1990) Herbicide resistance in Alopecurus myosuroides. In: Managing Resistance to Agrochemicals: From Fundamental Research to Practical Strategies (M.B. Gree, H.M. LeBaron and W.K. Moberg, eds.), 376–393. American Chemical Society, Washington.
Lamoureux, G.L., Rusness, D.G., Schröder, P. and Rennenberg, H. (1991) Diphenyl ether herbicide metabolism in a Spruce cell suspension culture: the identification of two novel metabolites derived from a glutathione conjugate. Pesticide Biochemistry Physiology 39: 291–301.
Matringe, M., Clair, D. and Scalla, R. (1990) Effects of peroxidizing herbicides on protoporphyrin IX levels in non-chlorophyllous soybean cell culture. Pesticide Biochemistry Physiology 36: 300–307.
Menendez, J., Jorrín, J., Taberner, A. and De Prado, R. (1993) Penetration, translocation and metabolization of diclofop-methyl in chlorotoluron-resistant and -susceptible biotypes of Alopecurus myosuroides. British Crop Protection Conference-Weeds 1: 213–220.
Menendez, J., Jorrín, J., Romera, E. and De Prado, R. (1994) Resistance to chlorotoluron of a slender foxtail (Alopecurus myosuroides)biotype. Weed Science 42: 340–344.
Moss, S.R. and Cussans, G.W. (1985) Variability in the susceptibility of Alopecurus myosuroides (black-grass) to chlorotoluron and isoproturon. Aspects Applied Biology 9: 91–98.
Murashige, T. and Skoog, F. (1962) A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiologia Plantarum 15: 151–158.
Niemans, P. and Pestemer, W. (1984) Resistenz verschiedener Herkunfte vob Acker-Fuchsschwanz (Alopecurus myosuroides) gegenuber Herbizidbehandlungen. Nachrich. Deuts. Pflanzen. 36: 113–118.
Ryan, P.J., Gross, D., Owen, W.J. and Loani, T.L. (1981) The metabolism of chlorotoluron, diuron and CGA 43057 in tolerant and susceptible plants. Pesticide Biochemistry Physilogy 16: 213–221.
Ryan, P.J. and Owen, W.J. (1982) The mechanism of selectivity of chlorotoluron between cereals and grassweeds. In: Proceedings 1982 British Crop Protection Conference-Weeds, 317–324.
Shedletzky, E., Shmuel, M., Delmer, D.P. and Lamport, D.T.A. (1990) Adaptation and growth of tomato cells on the herbicide 2,6-dichlorobenzonitrile leads to production of unique cell walls virtually lacking a cellulose-xyloglucan network. Plant Physiology 94: 980–987.
Shimabukuro, R.H., Walsh, W.C. and Jacobson, (1987) Aryl-O-glucoside of diclofop: A detoxification product in wheat shoots and wild oat cell suspension culture. Journal Agricultural Food Chemistry 35: 393.
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 Science 36: 558–565
Sterling, T.M. and Balke, N.E. (1989) Differential bentazon metabolism and retention of bentazon metabolites by plant cell cultures. Pesticide Biochemistry Physiology 34: 39–48.
Swisher, B.A. and Weimer, M.R. (1986) Comparative detoxification of chlorotoluron in leaf disks and cell cultures of two perennial weeds. Weed Science 34: 507–512.
Vasil, V., Castillo, A.M., Fromm, M.E. and Vasil, I.K. (1992) Herbicide resistant transgenic wheat plants obtained by microprojectile bombardment of regenerable embryogenic callus. Bio/technology 10: 667–674.
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Menendez, J., Jorrin, J., De Prado, R. (1997). Metabolism of Chlorotoluron in Resistant and Susceptible Alopecurus Myosuroides. Biotypes. a Study Using Plant Cell Suspensions. In: De Prado, R., Jorrín, J., García-Torres, L. (eds) Weed and Crop Resistance to Herbicides. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-5538-0_18
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DOI: https://doi.org/10.1007/978-94-011-5538-0_18
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