Skip to main content

Benzoxazinones: Cyclic hydroxamic acids found in plants

  • Conference paper
Residue Reviews

Part of the book series: Residue Reviews ((RECT,volume 64))

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

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).

    Article  CAS  Google Scholar 

  • Barba, R. C., and R. R. Romanowskr, JR.: Differential phytotoxicity of atrazine and ametryne to bananas. Weed Res. 9, 114 (1969).

    Article  CAS  Google Scholar 

  • Beck, S. D.: Resistance of plants to insects. Ann. Rev. Entomol. 10, 207 (1965).

    Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • 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).

    Article  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Elnaghy, M. A., and M. Shaw: Correlation between resistance to stem rust and the concentration of glucoside in wheat. Nature 210, 417 (1966).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Gallun, R. L., K. J. Starxs, and W. D. Guthrie: Plant resistance to insects attacking cereals. Ann. Rev. Entomol. 20, 337 (1975).

    Article  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Hamilton, R. H., and D. E. Moreland: Simazine: Degradation by corn seedlings. Science 135, 373 (1961).

    Article  CAS  Google Scholar 

  • Hamilton, R. H., R. S. Bandurski, and W. H. Reusch: Isolation and characterization of cylic hyroxamate from Zea mays. Cereal Chem. 39, 107 (1962).

    CAS  Google Scholar 

  • Hieta, P. K., and A. I. Virtanen: Precursors of benzoxazolinone in rye plants. II. Precursor I, the glucoside. Acta Chem. Scand. 14, 502 (1960).

    Article  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Hurter, J.: Abbauprodukte von Simazine in Gramineen. Experientia 22, 741 (1966).

    Article  CAS  Google Scholar 

  • Ingham, J. L.: Phytoalexins and other natural products as factors in plant disease resistance. The Bot. Rev. 38, 343 (1972).

    Article  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • Lund-Hole, K.: Uptake, translocation and metabolism of simazine in Norway Spruce (Picea abies). Weed Res. 9, 142 (1969).

    Article  Google Scholar 

  • Mace, M. E.: Histochemistry of beta-glucosidase in isolines of Zea mays susceptible or resistant to Northern Corn Leaf Blight. Phytopathol. 63, 243 (1973).

    Article  CAS  Google Scholar 

  • Maehr, H.: Antibiotics and other naturally occurring hydroxamic acids and hy-droxamates. Pure & Applied Chem. 28, 603 (1971).

    Article  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • Maxwell, F. G., J. N. Jenkins, and W. L. Parrot: Review of European corn borer resistance. Adv. Agron. 24, 187 (1972).

    Article  Google Scholar 

  • Molot, P. M.: Recherches sur la résistance du maïs à l’Helminthosporiose et aux Fusarioses. II. Ann. Phytopathol. 1, 353 (1969).

    CAS  Google Scholar 

  • 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).

    Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Radosevich, S. R., and A. P. Appleby: Studies on the mechanism of resistance to simazine in common groundsel. Weed Sci. 21, 497 (1973).

    CAS  Google Scholar 

  • Roeth, F. W., and T. L. Lavy: Atrazine translocation and metabolism in Sudangrass, sorghum and corn. Weed Sci. 19, 98 (1971).

    CAS  Google Scholar 

  • Shimabuxuro, R. H.: Significance of atrazine dealkylation in root and shoot of pea plants. J. Agr. Food Chem. 15, 557 (1967a).

    Article  Google Scholar 

  • Shimabuxuro, R. H.: Atrazine metabolism and herbicidal selectivity. Plant Physiol. 42, 1269 (1967b).

    Article  Google Scholar 

  • Shimabuxuro, R. H.: Atrazine metabolism in resistant corn and sorghum. Plant Physiol. 43, 1925 (1968).

    Article  Google Scholar 

  • Shimabuxuro, R. H., and H. R. Swanson: Atrazine metabolism in cotton as a basis for intermediate tolerance. Weed Sci. 18, 231 (1970).

    Google Scholar 

  • Shimabuxuro, R. H., D. S. Frear, H. R. Swanson, and W. C. Walsh: Glutathione conjugation of atrazine. Plant Physiol. 47, 10 (1971).

    Article  Google Scholar 

  • Shimabuxuro, R. H.:, R. E. Kadunce, and D. S. Frear: Dealkylation of atrazine in mature pea plants. J. Agr. Food Chem. 14, 392 (1966).

    Article  Google Scholar 

  • Sikka, H. C., and D. E. Davis: Absorption, translocation and metabolism of prometryne in cotton and soybean. Weed Sci. 16, 474 (1968).

    CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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)

    Article  CAS  Google Scholar 

  • 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).

    Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Virtanen, A. I.: Some aspects of factors in the maize plant with toxic effects on insect larvae. Suomen Kemistilehti B. 34, 29 (1961).

    Google Scholar 

  • Virtanen, A. I., and P. K. Hietala: 2(3)-Benzoxazolinone an anti-fusarium factor in rye seedlings. Acta Chem. Scand. 9, 1543 (1955).

    Article  CAS  Google Scholar 

  • Virtanen, A. I., and P. K. Hietala: On the structure of the precursors of benzoxazolinone in rye plants. II. Suomen Kemistilehti 32, 252 (1959).

    Google Scholar 

  • Virtanen, A. I., and P. K. Hietala: Precursors of benzoxazolinone in rye plants I. Precursors II, the aglucone. Acta Chem. Scand. 14, 499 (1960).

    Article  Google Scholar 

  • Virtanen, A. I, and O. Wahlroos: Absence of 6-methoxybenzoxazolinone in uninjured maize tissue. J. Pharm. Sci. 52, 713 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Virtanen, A. I., P. K. Hietala, and O. Wahlroos: An antifungal factor in maize and wheat plants. Suomen Kemistilehti B. 29, 143 (1956).

    Google Scholar 

  • Virtanen, A. I., P. K. Hietala, and O. Wahlroos: Antimicrobial substances in cereals and fodder plants. Arch. Biochem. Biophys. 69, 286 (1957).

    Article  Google Scholar 

  • 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).

    Article  Google Scholar 

  • Wamlroos, O., and A. I. Virtanen: On the formation of 6-methoxybenzoxazolinone in maize and wheat plants. Suomen Kemistilehti B. 32, 139 (1959).

    Google Scholar 

  • Walker, J. C., and M. A. Stahmann: Chemical nature of disease resistance in plants. Ann. Rev. Plant Physiol. 6, 351 (1955).

    Article  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  Google Scholar 

  • 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).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints 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

Publish with us

Policies and ethics