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Nicosulfuron, primisulfuron, and bentazon hydroxylation by corn (Zea mays), woolly cupgrass (Eriochloa villosa), and shattercane (Sorghum bicolor) cytochrome P-450

Published online by Cambridge University Press:  12 June 2017

John R. R. Hinz
Affiliation:
Agronomy Department. Iowa State University, Ames, IA 50011-1010
Michael Barrett
Affiliation:
University of Kentucky, Lexington, KY 40506-0091

Abstract

Microsomes (100,000 g pellet containing mixed membrane fractions but primarily endoplasmic reticulum) were isolated from shoots of corn, shattercane, and woolly cupgrass grown from naphthalic anhydride treated or untreated seed to determine if metabolism of bentazon, nicosulfuron, and primisulfuron could be demonstrated in the preparations. Corn is tolerant of all three herbicides, shattercane is tolerant of bentazon, and woolly cupgrass is tolerant of bentazon and primisulfuron. Naphthalic anhydride treatment was required for detectable bentazon, nicosulfuron, and primisulfuron hydroxylation in corn microsomes and for bentazon hydroxylation in woolly cupgrass microsomes. Bentazon hydroxylation was low, but detectable, in microsomes from shattercane shoots without naphthalic anhydride treatment. Naphthalic anhydride-treated corn microsomes hydroxylated 292, 120, and 52 pmol mg−1 protein min−1 of bentazon, nicosulfuron, and primisulfuron, respectively. Primisulfuron (19 pmol mg−1 protein min−1), but not nicosulfuron, was hydroxylated in woolly cupgrass microsomes. Neither nicosulfuron nor primisulfuron was hydroxylated in shattercane microsomes. Bentazon and primisulfuron inhibited nicosulfuron hydroxylation in corn microsomes. Bentazon, but not nicosulfuron, also inhibited primisulfuron hydroxylation in the corn microsomes. This indicates that the three herbicides can interact at the same cytochrome P-450(s) in corn. Primisulfuron hydroxylation was not inhibited by either bentazon or nicosulfuron in woolly cupgrass microsomes. This suggests that the cytochrome P-450(s) for primisulfuron hydroxylation are different between corn and woolly cupgrass. Also, bentazon hydroxylation in corn and shattercane microsomes was inhibited by the cytochrome P-450 inhibitor tetcyclasis, while that in woolly cupgrass was not. Again, this suggests a difference in the cytochrome P-450(s) responsible for bentazon metabolism among the species. Although absolute conclusions comparing in vitro microsomal activities to whole plant herbicide tolerance cannot be made because it is unknown whether the same cytochrome P-450(s) are studied in microsomes from naphthalic anhydride-treated tissue as are responsible for in vivo herbicide metabolism, there was a broad correlation between metabolism of a particular herbicide in microsomes of a species and the species' tolerance of that herbicide.

Type
Physiology, Chemistry, and Biochemistry
Copyright
Copyright © 1997 by the Weed Science Society of America 

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References

Literature Cited

Barrett, M., Bradshaw, L. D., Polge, N. D., Baerge, R. J., and Poneleit, C. G. 1994. Evidence for a multiple herbicide metabolizing cytochrome P-450 from maize. Weed Sci. Soc. Am. Abstr. 34: 60.Google Scholar
Bolwell, G. P., Bozak, K., and Zimmerlin, A. 1994. Review article number 96. Plant cytochrome P-450. Phytochemistry 37: 14911506.Google Scholar
Bradford, M. M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72: 248.Google Scholar
Bradshaw, L. D., Barrett, M., and Poneleit, C. G. 1994. Inheritance of bentazon susceptibility in a corn (Zea mays) line. Weed Sci. 42: 641647.Google Scholar
Brown, H. M. 1990. Mode of action, crop selectivity, and soil relations of the sulfonylurea herbicides. Pestic. Sci. 29: 263281.Google Scholar
Brown, H. M., Dietrich, R. F., Kenyon, W. H., and Lichtner, F. T. 1991. Prospects for biorational design of crop selective herbicides. Brighton Crop Prot. conf.—Weeds 7A-2:847856.Google Scholar
Burton, J. D. and Maness, E. P. 1992. Constitutive and inducible bentazon hydroxylation in shattercane (Sorghum bicolor) and johnsongrass (S. halapense). Pestic. Biochem. Physiol. 44: 4049.Google Scholar
Burton, J. D., Maness, E. M., Monks, D. W., and Robinson, D. K. 1994. Sulfonylurea selectivity and safener activity in ‘Landmark’ and ‘Merit’ sweet corn. Pestic. Biochem. Physiol. 48: 163172.Google Scholar
Diehl, K. E., Stoller, E. W., and Barrett, M. 1995. In vivo and in vitro inhibition of nicosulfuron metabolism by terbufos metabolites in maize. Pestic. Biochem. Physiol. 51: 137149.CrossRefGoogle Scholar
Donaldson, R. P. and Luster, D. G. 1991. Multiple forms of plant cytochromes P-450. Plant Physiol. 96: 369374.Google Scholar
Fonne-Pfister, R., Gaudin, J., Kreuz, K., Ramsteiner, K., and Ebert, E. 1990. Hydroxylation of primisulfuron by an inducible cytochrome P-450-dependant monooxygenase system from maize. Pestic. Biochem. Physiol. 37: 165173.Google Scholar
Frey, M., Kliem, R., Saedler, H., and Gierl, A. 1995. Expression of a cytochrome P450 gene family in maize. Mol. Gen. Genet. 246: 100109.Google Scholar
Gotoh, O. 1992. Substrate recognition sites in cytochrome P450 family 2(cyp2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J. Biol. Chem. 267: 8390.Google Scholar
Green, J. M. and Ulrich, J. F. 1993. Response of maize (Zea mays) inbreds and hybrids to sulfonylureas. Weed Sci. 41: 508516.Google Scholar
Green, J. M. and Ulrich, J. F. 1994. Response of maize (Zea mays) inbreds and hybrids to rimsulfuron. Pestic. Sci. 31: 187191.Google Scholar
Haack, A. E. and Balke, N. E. 1994. Enhancement of microsomal bentazon 6-hydroxylase and cinnamic acid 4-hydroxylase activities in grain sorghum shoots. Pestic. Biochem. Physiol. 50: 92105.Google Scholar
Harms, C. T., Montoya, A. L., Privalle, L. S., and Briggs, R. W. 1990. Genetic and biochemical characterization of corn inbred lines tolerant to the sulfonylurea herbicide primisulfuron. Theor. Appl. Genet. 80: 353358.Google Scholar
Helvig, C., Tardif, F. J., Seyer, A., Powles, S. B., Mioskowski, C., Durst, F., and Salaun, J. P. 1996. Selective inhibition of a cytochrome P450 enzyme in wheat that oxidizes both the natural substrate lauric acid and the synthetic herbicide dichlofop. Pestic. Biochem. Physiol. 54: 161171.Google Scholar
Hinz, J.R.R. and Owen, M.D.K. 1996. Nicosulfuron and primisulfuron selectivity in corn (Zea mays) and two annual grasses. Weed Sci. 44: 219223.Google Scholar
Kang, M. S. 1993. Inheritance of susceptibility to nicosulfuron herbicide in maize. J. Hered. 84: 216217.Google Scholar
Khan, M. and Kapusta, G. 1988. Corn tolerance to postemergence-applied DPX-V9360 and CGA-136872. North Cent. Res. Rep. 45:356357.Google Scholar
Kruez, K. and Fonne-Pfister, R. 1992. Herbicide-insecticide interaction in maize: malathion inhibits cytochrome P450-dependant primisulfuron metabolism. Pestic. Biochem Physiol. 43: 232240.Google Scholar
Lamoureux, G. L. and Rusness, D. G. 1992. The mechanism of action of BAS 145 138 as a safener for chlorimuron ethyl in corn: effect on hydroxylation, glutathione conjugation, glucoside conjugation, and acetolactate synthase. Pestic. Biochem. Physiol. 42: 128139.Google Scholar
Lau, M. C., Harder, P. A., and O'Keefe, D. 1993. Low carbon monoxide affinity allene oxide synthase is the predominant cytochrome P450 in many plant tissues. Biochemistry 32: 19451950.Google Scholar
Moreland, D. E., Corbin, F. T., and McFarland, J. E. 1993a. Effects of safeners on the oxidation of multiple substrates by grain sorghum microsomes. Pestic. Biochem. Physiol. 45: 4353.Google Scholar
Moreland, D. E., Corbin, F. T., and McFarland, J. E. 1993b. Oxidation of multiple substrates by corn shoot microsomes. Pestic. Biochem. Physiol. 47: 206214.CrossRefGoogle Scholar
Neighbors, S. and Privalle, L. S. 1990. Metabolism of primisulfuron by barnyard grass. Pestic. Biochem. Physiol. 37: 145153.Google Scholar
Obrigawitch, T. T., Kenyon, W. H., and Kurtale, H. 1990. Effect of application timing on rhizome johnsongrass (Sorghum halepense) control with DPX-V9360. Weed Sci. 38: 4549.Google Scholar
Omura, T. and Sato, R. 1964. The carbon-monoxide binding pigment of liver microsomes: I. Evidence for its hemoprotein nature. J. Biol. Chem. 239: 23702378.Google Scholar
Polge, N. D. and Barrett, M. 1995. Characterization of cytochrome P450-mediated chlorimuron ethyl hydroxylation in maize microsomes. Pestic. Biochem. Physiol. 53: 193204.CrossRefGoogle Scholar
Schuler, M. A. 1996. Plant cytochrome P450 monooxygenases. Crit. Rev. Plant Sci. 15: 235284.Google Scholar
Sweester, P. B. 1985. Safening of sulfonylurea herbicides to cereal crops: mode of herbicide antidote action. Proc. Br. Crop Prot. Conf.—Weeds 9B-1: 11541174.Google Scholar
Sweester, P. B., Schow, G. S., and Hutchinson, J. M. 1982. Metabolism of chlorsulfuron by plants: basis for selectivity of a new herbicide for cereals. Pestic. Biochem. Physiol. 17: 1823.Google Scholar
Thalacker, F. W., Swanson, H. R., and Frear, D. S. 1994. Characterization, purification, and reconstitution of an inducible cytochrome P450-dependent triasulfuron hydroxylase from wheat. Pestic. Biochem. Physiol. 29: 209223.Google Scholar
Windstrom, N. W. and Dowler, C. C. 1995. Sensitivity of selected field corn (Zea mays) inbreds and hybrids to nicosulfuron. Weed. Technol. 31: 779782.Google Scholar