Abstract
The benzoxazinones are naturally occurring cyclic hydroxamic acids found in numerous plant species. Their possible role in insect and disease resistance, and detoxication of the triazine herbicides, has aroused scientific interest in several disciplines.
Michigan Agricultural Experiment Station, Journal Article No. 7470.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
Similar content being viewed by others
References
Ashford, A. E., and M. E. McCully: Histochemical localization of ß-glycosidases in roots of Zea mays. Protoplasma 77, 411 (1973).
Barba, R. C., and R. R. Romanowskr, JR.: Differential phytotoxicity of atrazine and ametryne to bananas. Weed Res. 9, 114 (1969).
Beck, S. D.: Resistance of plants to insects. Ann. Rev. Entomol. 10, 207 (1965).
Beck, S. D., E. T. Kaske, and E. E. Smissman: Quantitative estimation of the resistance factor, 6-methoxybenzoxazolinone, in corn plant tissue. J. Agr. Food Chem. 5, 933 (1957).
Bemiller, J. N., and A. J. Pappelis: 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside in corn. I. Relation of water-soluble, I-butanol-soluble glycoside fraction content of pith cores and stalk rot resistance. Phytopathol. 55, 1237 (1965).
Calus, A. G., G. M. Dunn, D. G. Routley, and R. M. Couture: Genetic and environmental effects on production of inhibitory compounds in corn resistant to Helminthosporium turcicum. Crop Sci. 14, 359 (1974).
Couture, R. M., D. G. Routley, and G. M. Dunn: Role of cyclic hydroxamic acids in monogenic resistance of maize to Helminthosporium turcicum. Physiol. Plant. Pathol. 1, 515 (1971).
Dabler, J. M., A. J. Pappelis, and J. N. Bemiller: Effect of phenolic acids and corn extracts upon spore germination of Diplodia zeae. Phytopathol. 59, 1098 (1969).
Elnaghy, M. A., and P. Linko: The role of 4–0-glucosyl-2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one in resistance of wheat to stem rust. Physiol. Plant. 15, 764 (1962).
Elnaghy, M. A., and M. Shaw: Correlation between resistance to stem rust and the concentration of glucoside in wheat. Nature 210, 417 (1966).
Gahagan, H. E., and R. O. Mumma: The isolation of 2-(2-hydroxy-7-methoxy-1,4benzoxazin-3-one)ß-D-glucopyranoside from Zea mays. Phytochem. 6, 1441 (1967).
Gallun, R. L., K. J. Starxs, and W. D. Guthrie: Plant resistance to insects attacking cereals. Ann. Rev. Entomol. 20, 337 (1975).
Hamilton, R. H.: Tolerance of several grass species to 2-chloro-s-triazine herbicides in relation to degradation and content of benzoxazinone derivatives. J. Agr. Food Chem. 12, 14 (1964).
Hamilton, R. H., and D. E. Moreland: Simazine: Degradation by corn seedlings. Science 135, 373 (1961).
Hamilton, R. H., R. S. Bandurski, and W. H. Reusch: Isolation and characterization of cylic hyroxamate from Zea mays. Cereal Chem. 39, 107 (1962).
Hieta, P. K., and A. I. Virtanen: Precursors of benzoxazolinone in rye plants. II. Precursor I, the glucoside. Acta Chem. Scand. 14, 502 (1960).
Hofman, J., and O. Hofmanova: 1,4-Benzoxazine derivatives in plants: Sephadex fractionation and identification of a new glucoside. European J. Biochem. 8, 109 (1969).
Hofman, J., and O. Hofmanova: 1,4-Benzoxazine derivatives in plants: Absence of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3 (4H) -one from uninjured Zea mays plants. Phytochem. 10, 1441 (1971).
Honkanen, E., and A. I. Virtanen: On the reaction of 2,4-dihydroxy-1,4-benzoxazin-3-one to 2(3) -benzoxazolinone. Acta Chem. Scand. 15, 221 (1961).
Hurter, J.: Abbauprodukte von Simazine in Gramineen. Experientia 22, 741 (1966).
Ingham, J. L.: Phytoalexins and other natural products as factors in plant disease resistance. The Bot. Rev. 38, 343 (1972).
Klun, J. A., and T. A. Brindley: Role of 6-methoxy benzoxazolinone in inbred resistance of host plants (Maize) to first-brood larvae of european corn borer. J. Econ. Entomol. 59, 711 (1966).
Klun, J. A., and J. F. Robinson: Concentration of two 1,4-benzoxazinones in dent corn at various stages of development of the plant and its relation to resistance of the host plant to the european corn borer J. Econ. Entomol. 62, 214 (1969).
Klun, J. A., W. D. Guthrie, A. R. Hallauer, and W. A. Russell: Genetic nature of the concentration of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one and resistance to the european corn borer in a diallele set of eleven maize inbreds. Crop Sci. 10, 87 (1970a).
Klun, J. A., C. L. Tipton, J. F. Robinson, D. L. Ostrem, and M. Beroza: Isolation and identification of 6,7-dimethoxy-2-benzoxazolinone from dried tissues of Zea mays (L.) and evidence of its cyclic hydroxamic acid precursor. J. Agr. Food Chem. 18, 663 (1970b).
Klun, J. A., and T. A. Brindley: 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), an active agent in the resistance of maize to the european corn borer. J. Econ. Entomol. 60, 1529 (1967).
Knott, D. R., and J. Kumar: Tests of the relationship between a specif phenolic glucoside and stem rust resistance in wheat. Physiol. Plant Pathol. 2, 393 (1972).
Lamoureux, G. L., L. E. Stafford, and R. H. Shimabukuro: Conjugation of 2-chloro-4,6-bis(alkylamino)-s-triazines in higher plants. J. Agr. Food Chem. 20, 1004 (1972).
Long, B. J., G. M. Dunn, and D. G. Routley: Relationship of hydroxamic acid content (DIMBOA) in maize to resistance to Helminthosporium turcicum. Crop Sci. 15, 333 (1975).
Loomis, R. S., S. D. Beck, and J. F. Stauffer: The European corn borer, Pyrausta nibilalis (Hubn). and its principal host plant. V. A. chemical study of host plant resistance. Plant Physiol. 32, 379 (1957).
Lund-Hole, K.: Uptake, translocation and metabolism of simazine in Norway Spruce (Picea abies). Weed Res. 9, 142 (1969).
Mace, M. E.: Histochemistry of beta-glucosidase in isolines of Zea mays susceptible or resistant to Northern Corn Leaf Blight. Phytopathol. 63, 243 (1973).
Maehr, H.: Antibiotics and other naturally occurring hydroxamic acids and hy-droxamates. Pure & Applied Chem. 28, 603 (1971).
Maxwell, F. G., J. N. Jenkins, and W. L. Parrot: Influence of constituents of the cotton plant of feeding, oviposition, and development of the boll weevil. J. Econ. Entomol. 60, 1294 (1967).
Maxwell, F. G., J. N. Jenkins, and W. L. Parrot: Review of European corn borer resistance. Adv. Agron. 24, 187 (1972).
Molot, P. M.: Recherches sur la résistance du maïs à l’Helminthosporiose et aux Fusarioses. II. Ann. Phytopathol. 1, 353 (1969).
Molot, P. M., and P. Anclade: Résistance commune des lignées de mais à L’Helmintho-sporiose (Helminthosporium turcicum Pass.) et à la Pyrale (Ostrinia nubilalis Hbn.) en relation avec la présence d’une substance identifiable à la 6-methoxy-2(3) -benzoxazolinone. Ann. Epiphyties 19, 75 (1968).
Palmer, R. D., and C. O. Groyan: Tolerance of corn lines to atrazine in relation to content of benzoxazinone derivative, 2-glucoside. Weeds 13, 219 (1965).
Radosevich, S. R., and A. P. Appleby: Studies on the mechanism of resistance to simazine in common groundsel. Weed Sci. 21, 497 (1973).
Roeth, F. W., and T. L. Lavy: Atrazine translocation and metabolism in Sudangrass, sorghum and corn. Weed Sci. 19, 98 (1971).
Shimabuxuro, R. H.: Significance of atrazine dealkylation in root and shoot of pea plants. J. Agr. Food Chem. 15, 557 (1967a).
Shimabuxuro, R. H.: Atrazine metabolism and herbicidal selectivity. Plant Physiol. 42, 1269 (1967b).
Shimabuxuro, R. H.: Atrazine metabolism in resistant corn and sorghum. Plant Physiol. 43, 1925 (1968).
Shimabuxuro, R. H., and H. R. Swanson: Atrazine metabolism in cotton as a basis for intermediate tolerance. Weed Sci. 18, 231 (1970).
Shimabuxuro, R. H., D. S. Frear, H. R. Swanson, and W. C. Walsh: Glutathione conjugation of atrazine. Plant Physiol. 47, 10 (1971).
Shimabuxuro, R. H.:, R. E. Kadunce, and D. S. Frear: Dealkylation of atrazine in mature pea plants. J. Agr. Food Chem. 14, 392 (1966).
Sikka, H. C., and D. E. Davis: Absorption, translocation and metabolism of prometryne in cotton and soybean. Weed Sci. 16, 474 (1968).
Smissman, E. E., M. D. Corbett, N. A. Jenny, and O. Kristiansen: Mechanism of the transformation of 2,4-dihydroxy-1,4-benzoxazin-3-ones to 2-hydroxy-2-methyl4-methoxy-1,4-benzoxazin-3-one to 2-benzoxazolinone. J. Org. Chem. 37, 1700 (1972).
Tipton, C. L., R. R. Husted, and F. H. C. Tsao: Catalysis of simazine hydrolysis by 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one. J. Agr. Food Chem. 19, 484 (1971)
Tipton, C. L., J. A. Klun, R. R. Husted, and M. D. Pierson: Cyclic hydroxamic acids and related compounds from maize. Isolation and characterization. Biochem. 9, 2866 (1967).
Tipton, C. L., M. C. Wang, F. H. C. Tsao, C. C. L. Tu, and R. R. Husted: Biosynthesis of 1,4-benzoxazin-3-ones in Zea mays. Phytochem. 12, 347 (1973).
Virtanen, A. I.: Some aspects of factors in the maize plant with toxic effects on insect larvae. Suomen Kemistilehti B. 34, 29 (1961).
Virtanen, A. I., and P. K. Hietala: 2(3)-Benzoxazolinone an anti-fusarium factor in rye seedlings. Acta Chem. Scand. 9, 1543 (1955).
Virtanen, A. I., and P. K. Hietala: On the structure of the precursors of benzoxazolinone in rye plants. II. Suomen Kemistilehti 32, 252 (1959).
Virtanen, A. I., and P. K. Hietala: Precursors of benzoxazolinone in rye plants I. Precursors II, the aglucone. Acta Chem. Scand. 14, 499 (1960).
Virtanen, A. I, and O. Wahlroos: Absence of 6-methoxybenzoxazolinone in uninjured maize tissue. J. Pharm. Sci. 52, 713 (1963).
Virtanen, A. I., P. K. Hietala, and O. Wahlroos: An antifungal factor in maize and wheat plants. Suomen Kemistilehti B. 29, 143 (1956).
Virtanen, A. I., P. K. Hietala, and O. Wahlroos: Antimicrobial substances in cereals and fodder plants. Arch. Biochem. Biophys. 69, 286 (1957).
Wamlroos, O., and A. I. Virtanen: The precursors of 6-methoxy-benzoxazolinone in maize and wheat plants, their isolation and some of their properties. Acta Chem. Scand. 13, 1906 (1959).
Wamlroos, O., and A. I. Virtanen: On the formation of 6-methoxybenzoxazolinone in maize and wheat plants. Suomen Kemistilehti B. 32, 139 (1959).
Walker, J. C., and M. A. Stahmann: Chemical nature of disease resistance in plants. Ann. Rev. Plant Physiol. 6, 351 (1955).
Whitney, N. J., and G. G. Mortimore: An antifungal substance in the corn plant and its effect on growth of two stalk-rotting fungi. Nature 183, 341 (1959a).
Whitney, N. J., and G. G. Mortimore: Isolation of the antifungal substance, 6-methoxy benzoxazolinone from field corn (Zea mays L.) in Canada. Nature 184, 1320 (1959b).
Whitney, N. J., and G. G. Mortimore: Effect of 6-methoxy benzoxalinone on the growth of Xanthomonas stewartii (Erw. Smith) Downson and its presence in sweet corn (Zea mays var. saccharata Bailey). Nature 189, 596 (1959c).
Willard, J. I., D. Penner, and D. H. Smith: Physiological tolerance in cereals to the cereal leaf beetle. Amer. Soc. Agron, Abstr. p. 78 (1974).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1976 Springer-Verlag New York Inc.
About this paper
Cite this paper
Willard, J.I., Penner, D. (1976). Benzoxazinones: Cyclic hydroxamic acids found in plants. In: Gunther, F.A., Gunther, J.D. (eds) Residue Reviews. Residue Reviews, vol 64. Springer, New York, NY. https://doi.org/10.1007/978-1-4684-7059-8_3
Download citation
DOI: https://doi.org/10.1007/978-1-4684-7059-8_3
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4684-7061-1
Online ISBN: 978-1-4684-7059-8
eBook Packages: Springer Book Archive