Hydroxamic acids derived from 2-hydroxy-2h-1,4-benzoxazin-3(4h)-one: Key defense chemicals of cereals

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 5, 2009, Pages 1677-1695

  Niemeyer, Hermann M ^a  

^a UNIVERSITY OF CHILE   (Chile)

Author keywords

Allelopathy; Benzoxazin 3 ones; Benzoxazolinones; Cereal aphids; Cereals; Defense; European corn borer; Gramineae; Hydroxamic acids; Poaceae; Secondary metabolites

Indexed keywords

2 HYDROXY 1,4 BENZOXAZIN 3 ONE; 2-HYDROXY-1,4-BENZOXAZIN-3-ONE; BENZOXAZINE DERIVATIVE; HYDROXAMIC ACID;

ANIMAL; APHID; CEREAL; GENE EXPRESSION REGULATION; GENETICS; IMMUNOLOGY; METABOLISM; MICROBIOLOGY; PARASITOLOGY; PHYSIOLOGY; PLANT DISEASE; REVIEW;

ANIMALS; APHIDS; BENZOXAZINES; CEREALS; GENE EXPRESSION REGULATION, PLANT; HYDROXAMIC ACIDS; PLANT DISEASES;

APHIDIDAE; FUNGI; OSTRINIA NUBILALIS; POACEAE; SECALE CEREALE; TRITICUM AESTIVUM; ZEA MAYS;

EID: 64549113674     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8034034     Document Type: Review

References (327)

1. Niemeyer, H. M. Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the Gramineae. Phytochemistry 1988, 27, 3349-3358.
2. Niemeyer, H. M.; Pérez, F. J. Potential of hydroxamic acids in the control of cereal pests, diseases, and weeds. In Allelopathy. Organisms, Processes, and Applications.; Inderjit, Dakshini, K. M. M., Einhellig, F. A., Eds.; American Chemical Society Symposium Series 582; American Chemical Society: Washington, DC, 1995; pp 260-270.
3. Hashimoto, Y.; Shudo, K. Chemistry of biologically active benzoxazinoids. Phytochemistry 1996, 43, 551-559.
4. Sicker, D.; Hartenstein, H.; Kluge, M. Natural benzoxazinoidss synthesis of acetal glucosides, aglucones, and analogues. In Recent Research DeVelopments in Phytochemistry; Pandalai, S. G., Ed.; Research Signpost: Trivandrum, India, 1997; pp 203-223.
5. Sicker, D.; Frey, M.; Schulz, M.; Gierl, A. Role of natural benzoxazinones in the survival strategy of plants. In International Review of Cytologysa Survey of Cell Biology; Academic Press Inc: San Diego, 2000; Vol. 198, pp 319-346.
6. Sicker, D.; Schultz, M. Benzoxazinones in plants: occurrence, synthetic access, and biological activity. In Studies in Natural Products Chemistry, Vol. 27. BioactiVe Natural Products (Part H); Atta-ur-Rahman, Ed.; Elsevier Science B.V.: 2002; pp 185-232.
7. Reimann, J. E.; Byerrum, R. U. Studies on the biosynthesis of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one. Biochemistry 1964, 3, 847-851.
8. Tipton, C. L.; Wang, M.-C.; Tsao, F. H.-C.; Lin Tu, C.-C.; Husted, R. R. Biosynthesis of 1,4-benzoxazin-3-ones in Zea mays. Phytochemistry 1973, 12, 347-352.
9. Peng, S. Y.; Chilton, W. S. Biosynthesis of DIMBOA in maize using deuterium oxide as a tracer. Phytochemistry 1994, 37, 167-171.
10. 4 into DIMBOA in maize. Tetrahedron Lett. 1994, 35, 3247-3250.
11. Kumar, P.; Moreland, D. E.; Chilton, W. S. 2H-1,4-Benzoxazin-3(4H)-one, an intermediate in the biosynthesis of cyclic hydroxamic acids in maize. Phytochemistry 1994, 36, 893-898.
12. Desai, S. R.; Kumar, P.; Chilton, W. S. Indole is an intermediate in the biosynthesis of cyclic hydroxamic acids in maize. Chem. Commun. 1996, 1321-1321.
13. 2. Phytochemistry 1997, 45, 715-718.
14. Frey, M.; Chomet, P.; Glawischnig, E.; Stettner, C.; Grun, S.; Winklmair, A.; Eisenreich, W.; Bacher, A.; Meeley, R. B.; Briggs, S. P.; Simcox, K.; Gierl, A. Analysis of a chemical plant defense mechanism in grasses. Science 1997, 277, 696-699.
15. Spiteller, P.; Glawischnig, E.; Gierl, A.; Steglich, W. Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2- one in Zea mays. Phytochemistry 2001, 57, 373-376.
16. Bailey, B. A.; Larson, R. L. Hydroxamic acid glycosyltransferases from maize seedlings. Plant Physiol. 1989, 90, 1071-1076.
17. Bailey, B. A.; Larson, R. L. Maize microsomal benzoxazinone N-monooxygenase. Plant Physiol. 1991, 95, 792-796.
18. Leighton, V.; Niemeyer, H. M.; Jonsson, L. M. V. Substrate specificity of a glucosyltransferase and an N-hydroxylase involved in the biosynthesis of cyclic hydroxamic acids in Gramineae. Phytochemistry 1994, 36, 887-892.
19. Glawischnig, E.; Grun, S.; Frey, M.; Gierl, A. Cytochrome P450 monooxygenases of DIBOA biosynthesis: Specificity and conservation among grasses. Phytochemistry 1999, 50, 925-930.
20. Tanabe, J.; Sue, M.; Ishihara, A.; Iwamura, H. Occurrence and characterization of 2-hydroxy-1,4-benzoxazin-3-one and indole hydroxylases in juvenile wheat. Biosci. Biotech. Biochem. 1999, 63, 1614-1617.
21. Sue, M.; Ishihara, A.; Iwamura, H. Occurrence and characterization of a UDP-glucose: hydroxamic acid glucosyltransferase isolated from wheat (Triticum aestivum) seedlings. Z. Naturforsch. C 2000, 55, 701-707.
22. Ebisui, K.; Ishihara, A.; Iwamura, H. Purification and characterization of UDP-glucose: cyclic hydroxamic acid -glucosyltransferases from maize seedlings. Plant Physiol. Biochem. 2001, 39, 27-35.
23. von Rad, U.; Huttl, R.; Lottspeich, F.; Gierl, A.; Frey, M. Two glucosyltransferases are involved in detoxification of benzoxazinoids in maize. Plant J. 2001, 28, 633-642.
24. Frey, M.; Huber, K.; Park, W. J.; Sicker, D.; Lindberg, P.; Meeley, R. B.; Simmons, C. R.; Yalpani, N.; Gierl, A. A 2-oxoglutarate-dependent dioxygenase is integrated in DIMBOA biosynthesis. Phytochemistry 2003, 62, 371-376.
25. Melanson, D.; Chilton, M. D.; Masters-Moore, D.; Chilton, W. S. A deletion in an indole synthase gene is responsible for the DIMBOA-deficient phenotype of bxbx maize. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 13345-13350.
26. Frey, M.; Stettner, C.; Pare, P. W.; Schmelz, E. A.; Tumlinson, J. H.; Gierl, A. An herbivore elicitor activates the gene for indole emission in maize. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 14801-14806.
27. Gierl, A.; Frey, M. Evolution of benzoxazinone biosynthesis and indole production in maize. Planta 2001, 213, 493-498.
28. Jonczyk, R.; Schmidt, H.; Osterrieder, A.; Fiesselmann, A.; Schullehner, K.; Haslbeck, M.; Sicker, D.; Hofmann, D.; Yalpani, N.; Simmons, C.; Frey, M.; Gierl, A. Elucidation of the final reactions of DIMBOA-glucoside biosynthesis in maize: characterization of Bx6 and Bx7. Plant Physiol. 2008, 146, 1053-1063.
29. Cuevas, L.; Niemeyer, H. M.; Jonsson, L. M. V. Partial purification and characterization of a hydroxamic acid glucoside β-D-glucosidase from maize. Phytochemistry 1992, 31, 2609-2612.
30. Sue, M.; Ishihara, A.; Iwamura, H. Purification and characterization of a hydroxamic acid glucoside β-glucosidase from wheat (Triticum aestivum L.) seedlings. Planta 2000, 210, 432-438.
31. Sue, M.; Ishihara, A.; Iwamura, H. Purification and characterization of a β-glucosidase from rye (Secale cereale L.) seedlings. Plant Sci 2000, 155, 67-74.
32. Esen, A.; Stetler, D. A. Subcellular localization of maize β-glucosidase. Maize Genet. News Lett. 1993, 67, 19-20.
33. Oikawa, A.; Ebisui, K.; Sue, M.; Ishihara, A.; Iwamura, H. Purification and characterization of a β-glucosidase specific for 2,4-dihydroxy-7- methoxy-1,4-benzoxazin-3-one (DIMBOA) glucoside in maize. Z. Naturforsch. C 1999, 54, 181-185.
34. Nomura, T.; Ishihara, A.; Imaishi, H.; Endo, T. R.; Ohkawa, H.; Iwamura, H. Molecular characterization and chromosomal localization of cytochrome P450 genes involved in the biosynthesis of cyclic hydroxamic acids in hexaploid wheat. Mol. Genet. Genomics 2002, 267, 210-217.
35. Grün, S.; Frey, M.; Gierl, A. Evolution of the indole alkaloid biosynthesis in the genus Hordeum: distribution of gramine and DIBOA and isolation of the benzoxazinoid biosynthesis genes from Hordeum lechleri. Phytochemistry 2005, 66, 1264-1272.
36. Argandoña, V. H.; Luza, J. G.; Niemeyer, H. M.; Corcuera, L. J. Role of hydroxamic acids in the resistance of cereals to aphids. Phytochemistry 1980, 19, 1665-1668.
37. Frey, M.; Kliem, R.; Saedler, H.; Gierl, A. Expression of a cycochrome P450 gene family in maize. Mol. Gen. Genet. 1995, 246, 100-109.
38. Nomura, T.; Ishihara, A.; Imaishi, H.; Ohkawa, H.; Endo, T. R.; Iwamura, H. Rearrangement of the genes for the biosynthesis of benzoxazinones in the evolution of Triticeae species. Planta 2003, 217, 776-782.
39. Niemeyer, H. M.; Jerez, J. M. Chromosomal location of genes for hydroxamic acid accumulation in Triticum aestivum L (wheat) using wheat aneuploids and wheat substitution lines. Heredity 1997, 79, 10-14.
40. Simcox, K. D.; Weber, D. F. Location of the benzoxazinless (bx) locus in maize by monosomic and B-A translocational analyses. Crop Sci. 1985, 25, 827-830.
41. Devos, K. M.; Gale, M. D. Comparative genetics in the grasses. Plant Mol. Biol. 1997, 35, 3-15.
42. Liu, C. J.; Atkinson, M. D.; Chinoy, C. N.; Devos, K. M.; Gale, M. D. Nonhomoeologous translocations between group 4, 5 and 7 chromosomes within wheat and rye. Theor. Appl. Genet. 1992, 83, 305-312.
43. Devos, K. M.; Atkinson, M. D.; Chinoy, C. N.; Francis, H. A.; Harcourt, R. L.; Koebner, R. M. D.; Liu, C. J.; Masojc, P.; Xie, D. X.; Gale, M. D. Chromosomal rearrangements in the rye genome relative to that of wheat. Theor. Appl. Genet. 1993, 85, 673-680.
44. Nomura, T.; Ishihara, A.; Yanagita, R. C.; Endo, T. R.; Iwamura, H. Three genomes differentially contribute to the biosynthesis of benzoxazinones in hexaploid wheat. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 16490-16495.
45. Nomura, T.; Ishihara, A.; Iwamura, H.; Endo, T. R. Molecular characterization of benzoxazinone-deficient mutation in diploid wheat. Phytochemistry 2007, 68, 1008-1016.
46. Nomura, T.; Nasuda, S.; Kawaura, K.; Ogihara, Y.; Kato, N.; Sato, F.; Kojima, T.; Toyoda, A.; Iwamura, H.; Endo, T. R. Structures of the three homoeologous loci of wheat benzoxazinone biosynthetic genes TaBx3 and TaBx4 and characterization of their promoter sequences. Theor. Appl. Genet. 2008, 116, 373-381.
47. Eljarrat, E.; Barceló, D. Sample handling and analysis of allelochemical compounds in plants. Trends Anal. Chem. 2001, 20, 584-590.
48. Lyons, P. C.; Hipskind, J. D.; Wood, K. V.; Nicholson, R. L. Separation and quantification of cyclic hydroxamic acids and related compounds by high-pressure liquid chromatography. J. Agric. Food Chem. 1988, 36, 57-60.
49. Niemeyer, H. M.; Pesel, E.; Franke, S.; Francke, W. Ingestion of the benzoxazinone DIMBOA from wheat plants by aphids. Phytochemistry 1989, 28, 2307-2310.
50. Xie, Y. S.; Atkinson, J.; Arnason, J. T.; Morand, P.; Philogène, B. J. R. Separation and quantification of 1,4-benzoxazin-3-ones and benzoxazolin-2-ones in maize root extract by highperformance liquid chromatography. J. Chromatogr. 1991, 543, 389-395.
51. Mayoral, A. M.; Gutiérrez, C.; Ruiz, M. L.; Castañera, P. A high performance liquid chroamatography method for quantification of DIBOA, DIMBOA, and MBOA from aqueous extracts of corn and winter cereal plants. J. Liq. Chromatogr. 1994, 17, 2651-2665.
52. Stochmal, A.; Kus, J.; Martyniuk, S.; Oleszek, W. Concentration of benzoxazinoids in roots of field-grown wheat (Triticum aestivum L.) varieties. J. Agric. Food Chem. 2006, 54, 1016-1022.
53. Villagrasa, M.; Guillamón, M.; Eljarrat, E.; Barceló, D. Determination of benzoxazinone derivatives in plants by combining pressurized liquid extraction-solid-phase extraction followed by liquid chromatography- electrospray mass spectrometry. J. Agric. Food Chem. 2006, 54, 1001-1008.
54. Rice, C. P.; Park, Y. B.; Adam, F.; Abdul-Baki, A. A.; Teasdale, J. R. Hydroxamic acid content and toxicity of rye at selected growth stages. J. Chem. Ecol. 2005, 31, 1887-1905.
55. Wu, H. W.; Haig, T.; Pratley, J.; Lemerle, D.; An, M. Simultaneous determination of phenolic acids and 2,4-dihydroxy- 7-methoxy-1,4-benzoxazin-3- one in wheat (Triticum aestivum L.) by gas chromatography-tandem mass spectrometry. J. Chromatogr. A 1999, 864, 315-321.
56. García, C.; García, S.; Heinzen, H.; Moyna, P.; Niemeyer, H. M. An efficient method for the quantification of hydroxamic acids from wheat by thin layer chromatography-densitometry. Phytochem. Anal. 1998, 9, 278-282.
57. Cambier, V.; Hance, T.; de Hoffmann, E. Non-injured maize contains several 1,4-benzoxazin-3-one related compounds but only as glucoconjugates. Phytochem. Anal. 1999, 10, 119-126.
58. Eljarrat, E.; Guillamón, M.; Seuma, J.; Mogensen, B. B.; Fomsgaard, I. S.; Olivero-Bastidas, A.; Macías, F. A.; Stochmal, A.; Oleszek, W.; Shakaliene, O.; Barceló, D. First European interlaboratory study of the analysis of benzoxazinone derivatives in plants by liquid chromatography. J. Chromatogr. A 2004, 1047, 69-76.
59. Bonnington, L.; Eljarrat, E.; Guillamón, M.; Eichhorn, P.; Taberner, A.; Barceló, D. Development of a liquid chromatography- electrospray-tandem mass spectrometry method for the quantitative determination of benzoxazinone derivatives in plants. Anal. Chem. 2003, 75, 3128-3136.
60. Villagrasa, M.; Guillamón, M.; Navarro, A.; Eljarrat, E.; Barceló, D. Development of a pressurized liquid extraction-solid-phase extraction followed by liquid chromatography-electrospray ionization tandem mass spectrometry method for the quantitative determination of benzoxazolinones and their degradation products in agricultural soil. J. Chromatogr. A 2008, 1179, 190-197.
61. Bonnington, L. S.; Barceló, D.; Knepper, T. P. Utilisation of electrospray time-of-flight mass spectrometry for solving complex fragmentation patterns: Application to benzoxazinone derivatives. J. Mass Spectrom. 2003, 38, 1054-1066.
62. Finney, M. M.; Danehower, D. A.; Burton, J. D. Gas chromatographic method for the analysis of allelopathic natural products in rye (Secale cereale L.). J. Chromatogr. A 2005, 1066, 249-253.
63. Guillamón, A.; Villagrasa, A.; Eljarrat, E.; Barceló, D. Development of a liquid chromatography-electrospray mass spectrometric method for the simultaneous analysis of benzoxazolinones and their degradation products. J. Chromatogr. A 2004, 1052, 53-59.
64. Hartenstein, H.; Klein, J.; Sicker, D. Efficient isolation procedure for (2R)-D-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one from maize. Indian J. Heterocycl. Chem. 1993, 2, 151-153.
65. Hartenstein, H.; Sicker, D. (2R)-2-β-D-glucopyranosyloxy-4-hydroxy- 2H-1,4-benzoxazin-3(4H)-one from Secale cereale. Phytochemistry 1994, 35, 827-828.
66. Kluge, M.; Grambow, H. J.; Sicker, D. (2R)-2-β-D-Glucopyranosyloxy- 4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one from Triticum aestivum. Phytochemistry 1997, 44, 639-641.
67. Hartenstein, H.; Lippmann, T.; Sicker, D. An efficient procedure for the isolation of pure 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) from maize. Indian J. Heterocycl. Chem. 1992, 2, 75-76.
68. Larsen, E.; Christensen, L. P. Simple method for large scale isolation of the cyclic arylhydroxamic acid DIMBOA from maize (Zea mays L.). J. Agric. Food Chem. 2000, 48, 2556-2558.
69. Sicker, D.; Prätorius, B.; Mann, G.; Meyer, L. A convenient synthesis of 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one. Synthesis 1989, 211-212.
70. Hartenstein, H.; Sicker, D. Syntheses of cyclic hydroxamic acids and lactams with 2,3-dioxo-1,4-benzoxazine skeleton. J. Prakt. Chem. 1993, 335, 359-362.
71. Kluge, M.; Sicker, D. Double diastereoselective glucosidation of cyclic hemiacetals: synthesis of the 1,4-benzoxazinone acetal glucosides GDIBOA and GDIMBOA from Gramineae. Tetrahedron 1996, 52, 10389-10398.
72. Niemeyer, H. M. Hydroxamic acid content of Triticum species. Euphytica 1988, 37, 289-293.
73. Copaja, S. V.; Barría, B. N.; Niemeyer, H. M. Hydroxamic acid content of perennial triticeae. Phytochemistry 1991, 30, 1531-1534.
74. Barría, B. N.; Copaja, S. V.; Niemeyer, H. M. Occurrence of DIBOA in wild Hordeum species and its relation to aphid resistance. Phytochemistry 1992, 31, 89-91.
75. Niemeyer, H. M.; Copaja, S. V.; Barría, B. N. The Triticeae as sources of hydroxamic acids, secondary metabolites in wheat conferring resistance against aphids. Hereditas 1992, 116, 295-299.
76. Gianoli, E.; Niemeyer, H. M. Allocation of herbivory-induced hydroxamic acids in the wild wheat Triticum uniaristatum. Chemoecology 1998, 8, 19-23.
77. Gianoli, E.; Niemeyer, H. M. DIBOA in wild Poaceae: Sources of resistance to the Russian wheat aphid (Diuraphis noxia) and the greenbug (Schizaphis graminum). Euphytica 1998, 102, 317-321.
78. Copaja, S. V.; Niemeyer, H. M.; Wratten, S. D. Hydroxamic acid levels in Chilean and British wheat seedlings. Ann. Appl. Biol. 1991, 118, 223-227.
79. Xie, Y. S.; Arnason, J. T.; Philogène, B. J. R.; Olechowski, H. T.; Hamilton, R. I. Variation of hydroxamic acid content in maize roots in relation to geographic origin of maize germplasm and resistance to western corn rootworm (Coleoptera: Chrysomelidae). J. Econ. Entomol. 1992, 85, 2478-2485.
80. Nicol, D.; Copaja, S. V.; Wratten, S. D.; Niemeyer, H. M. A screen of worldwide wheat cultivars for hydroxamic acid levels and aphid antixenosis. Ann. Appl. Biol. 1992, 121, 11-18.
81. Escobar, C. A.; Niemeyer, H. M. Potencial of hydroxamic acids in breeding for aphid resistance in wheat. Acta Agric. Scand. Sect. Bs-Soil Plant Sci. 1993, 43, 163-167.
82. Assabgui, R. A.; Arnason, J. T.; Hamilton, R. I. Hydroxamic acid content in maize (Zea mays) roots of 18 Ontario recommended hybrids and prediction of antibiosis to the western cornrootworm, Diabrotica virgifera virgifera LeConte (Coleoptera, Chrysomelidae). Can. J. Plant Sci. 1993, 73, 359-363.
83. Ni, X. Z.; Quisenberry, S. S. Comparison of DIMBOA concentrations among wheat isolines and corresponding plant introduction lines. Entomol. Exp. Appl. 2000, 96, 275-279.
84. Singh, P.; Suman, A.; Shrivastava, A. K. Isolation and identification of allelochemicals from sugarcane leaves. Allelopathy J. 2003, 12, 71-79.
85. Wu, H. W.; Haig, T.; Pratley, J.; Lemerle, D.; An, M. Allelochemicals in wheat (Triticum aestivum L.): Production and exudation of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one. J. Chem. Ecol. 2001, 27, 1691-1700.
86. Reberg-Horton, S. C.; Burton, J. D.; Danehower, D. A.; Ma, G. Y.; Monks, D. W.; Murphy, J. P.; Ranells, N. N.; Williamson, J. D.; Creamer, N. G. Changes over time in the allelochemical content of ten cultivars of rye (Secale cereale L.). J. Chem. Ecol. 2005, 31, 179-193.
87. Quader, M.; Daggard, G.; Barrow, R.; Walker, S.; Sutherland, M. W. Allelopathy, DIMBOA production and genetic variability in accessions of Triticum speltoides. J. Chem. Ecol. 2001, 27, 747-760.
88. Corcuera, L. J.; Argandoña, V. H.; Niemeyer, H. M. Effect of cyclic hydroxamic acids from cereals on aphids. In Chemistry and Biology of Hydroxamic Acids; Kehl, H., Ed.; Karger, A.G.: Basel, 1982; pp 111-118.
89. Copaja, S. V.; Villarroel, E.; Bravo, H. R.; Pizarro, L.; Argandoña, V. H. Hydroxamic acids in Secale cereale L. and the relationship with their antifeedant and allelopathic properties. Z. Naturforsch. C 2006, 61, 670-676.
90. Chatterjee, A.; Basa, S. C. Extractives of Acanthaceae: blepharin, a novel glucoside from Blepharis edulis Pers. Chem. Ind. 1969, 328.
91. Wolf, R. B.; Spencer, G. F.; Plattner, R. D. Benzoxazolinone, 2,4-dihydroxy-1,4-benzoxazin-3-one, and its glucoside from Acanthus mollis seeds inhibit velvetleaf germination and growth. J. Nat. Prod. 1985, 48, 59-63.
92. Kokpol, U.; Chittawong, V.; Miles, D. H. Chemical constituents of the roots of Acanthus illicifolius. J. Nat. Prod. 1986, 49, 355-356.
93. Chatterjee, A.; Sharma, N. J.; Banerji, J.; Basa, S. C. Studies on Acanthaceaesbenzoxazine glucoside and benzoxazolone from Blepharis edulis Pers. Indian J. Chem. 1990, 29B, 132-134.
94. Pratt, K.; Kumar, P.; Chilton, W. S. Cyclic hydroxamic acids in dicotyledonous plants. Biochem. Syst. Ecol. 1995, 23, 781-785.
95. Baumeler, A.; Hesse, M.; Werner, C. Benzoxazinoids-cyclic hydroxamic acids, lactams and their corresponding glucosides in the genus Aphelandra (Acanthaceae). Phytochemistry 2000, 53, 213-222.
96. Wahidulla, S.; Bhattacharjee, J. J. Benzoxazinoids from Acanthus illicifolius. J. Indian Inst. Sci. 2001, 81, 485-489.
97. Kanchanapoom, T.; Kasai, R.; Picheansoonthon, C.; Yamasaki, K. Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus. Phytochemistry 2001, 58, 811-817.
98. Kanchanapoom, T.; Kamel, M. S.; Kasai, R.; Picheansoonthon, C.; Hiraga, Y.; Yamasaki, K. Benzoxazinoid glucosides from Acanthus ilicifolius. Phytochemistry 2001, 58, 637-640.
99. Bravo, H. R.; Copaja, S. V.; Martin, J. S. Contents of 1,4-benzoxazin-3-ones and 2-benzoxazolinone from Stenandriumdulce (Nees). Z. Naturforsch. C 2004, 59, 177-180.
100. Huo, C. H.; Wang, B.; Lin, W. H.; Zhao, Y. Y. Benzoxazinones from Acanthus ilicifolius. Biochem. Syst. Ecol. 2005, 33, 643-645.
101. Ö zden, S.; Ö zden, T.; Attila, I.; Kücükislamoglu, M.; Okatan, A. Isolation and identification via high-performance liquid chromatography and thin-layer chromatography of benzoxazolinone precursor from Consolida orientalis flowers. J. Chromatogr. 1992, 609, 402-406.
102. Kamperdick, C.; Lien, T. P.; Sung, T. V.; Adam, G. 2-Hydroxy-2H-1,4- benzoxazin-3-one from Scoparia dulcis. Pharmazie 1997, 52, 965-966.
103. Bravo, H. R.; Copaja, S. V.; Figueroa-Duarte, S.; Lamborot, M.; Martin, J. S. 1,4-Benzoxazin-3-one, 2-benzoxazolinone and gallic acid from Calceolaria thyrsilora Graham and their antibacterial activity. Z. Naturforsch. C 2005, 60, 389-393.
104. Alipieva, K. I.; Taskova, R. M.; Evstatieva, L. N.; Handjieva, N. V.; Popov, S. S. Benzoxazinoids and iridoid glucosides from four Lamium species. Phytochemistry 2003, 64, 1413-1417.
105. Schullehner, K.; Dick, R.; Vitzthum, F.; Schwab, W.; Brandt, W.; Frey, M.; Gierl, A. Benzoxazinoid biosynthesis in dicot plants. Phytochemistry 2008, 69, 2668-2677.
106. Nakagawa, E.; Amano, T.; Hirai, N.; Iwamura, H. Non-induced cyclic hydroxamic acids in wheat during juvenile stage of growth. Phytochemistry 1995, 38, 1349-1354.
107. Cambier, V.; Hance, T.; de Hoffmann, E. Variation of DIMBOA and related compounds content in relation to the age and plant organ in maize. Phytochemistry 2000, 53, 223-229.
108. Villagrasa, M.; Guillamón, M.; Labandeira, A.; Taberner, A.; Eljarrat, E.; Barceló, D. Benzoxazinoid allelochemicals in wheat: distribution among foliage, roots, and seeds. J. Agric. Food Chem. 2006, 54, 1009-1015.
109. Iwamura, H.; Nakagawa, E.; Hirai, N. Localization of benzoxazinones that occur constitutively in wheat seedlings. Z. Naturforsch. C 1996, 51, 807-812.
110. Copaja, S. V.; Nicol, D.; Wratten, S. D. Accumulation of hydroxamic acids during wheat germination. Phytochemistry 1999, 50, 17-24.
111. Burgos, N. R.; Talbert, R. E.; Mattice, J. D. Cultivar and age differences in the production of allelochemicals by Secale cereale. Weed Sci. 1999, 47, 481-485.
112. Wu, H. W.; Haig, T.; Pratley, J.; Lemerle, D.; An, M. Distribution and exudation of allelochemicals in wheat Triticum aestivum. J. Chem. Ecol. 2000, 26, 2141-2154.
113. Park, W. J.; Hochholdinger, F.; Gierl, M. Release of the benzoxazinoids defense molecules during lateral-and crown root emergence in Zea mays. J. Plant Physiol. 2004, 161, 981-985.
114. Gianoli, E.; Ríos, J. M.; Niemeyer, H. M. Factors governing within-plant allocation of a chemical defence in Secale cereale. Which is the appropriate currency of allocation? Chemoecology 1999, 9, 113-117.
115. Mogensen, B. B.; Krongaard, T.; Mathiassen, S. K.; Kudsk, P. Quantification of benzoxazinone derivatives in wheat (Triticum aestivum) varieties grown under contrasting conditions in Denmark. J. Agric. Food Chem. 2006, 54, 1023-1030.
116. Thackray, D. J.; Wratten, S. D.; Edwards, P. J.; Niemeyer, H. M. Resistance to the aphids Sitobion avenae and Rhopalosiphum padi in Gramineae in relation to hydroxamic acid levels. Ann. Appl. Biol. 1990, 116, 573-582.
117. Xie, Y. S.; Arnason, J. T.; Philogène, B. J. R.; Lambert, J. D. H.; Atkinson, J.; Morand, P. Role of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3- one (DIMBOA) in the resistance of maize towestern corn rootworm Diabrotica virgifera virgifera (Leconte) (Coleoptera: Chrysomelidae). Can. Entomol. 1990, 122, 1177-1186.
118. Morse, S.; Wratten, S. D.; Edwards, P. J.; Niemeyer, H. M. Changes in the hydroxamic acid content of maize leaves with time and after artificial damage; implications for insect attack. Ann. Appl. Biol. 1991, 119, 239-249.
119. Gregersen, P. L.; Holm, P. B. Transcriptome analysis of senescence in the flag leaf of wheat (Triticum aestivum L.). Plant Biotech. J. 2007, 5, 192-206.
120. Zúñiga, G. E.; Massardo, F. Hydroxamic acid content in undifferentiated and differentiated tissues of wheat. Phytochemistry 1991, 30, 3281-3283.
121. Zúñiga, G. E.; Copaja, S. V.; Bravo, H. R.; Argandoña, V. H. Hydroxamic acids accumulation by wheat callus. Phytochemistry 1990, 29, 2139-2141.
122. Givovich, A.; Sandström, J.; Niemeyer, H. M.; Pettersson, J. Presence of a hydroxamic acid glucoside in wheat phloem sap, and its consequences for performance of Rhopalosiphum padi (L.) (Homoptera: Aphididae). J. Chem. Ecol. 1994, 20, 1923-1930.
123. Caillaud, C. M.; Niemeyer, H. M. Possible involvement of the phloem sealing system in the acceptance of a plant as host by an aphid. Experientia 1996, 52, 927-931.
124. Pérez, F. J.; Ormeño-Núñez, J. Difference in hydroxamic acid content in roots and root exudates of wheat (Triticum aestivum L.) and rye (Secale cereale L.): possible role in allelophathy. J. Chem. Ecol. 1991, 17, 1037-1043.
125. Pethó, M. Occurrence and physiological role of benzoxazinones and their derivatives. III. Possible role of 7-methoxy-benzoxazinone in the iron uptake of maize. Acta Agron. Hung. 1992, 41, 57-64.
126. Konstantopoulou, M. A.; Krokos, F. D.; Mazomenos, B. E. Chemical composition of corn leaf essential oils and their role in the oviposition behavior of Sesamia nonagrioides females. J. Chem. Ecol. 2004, 30, 2243-2256.
127. Zhang, X.; Habib, F. K.; Ross, M.; Burger, U.; Lewenstein, A.; Rose, K.; Jaton, J. C. Isolation and characterization of a cyclic hydroxamic acid from a pollen extract, which inhibits cancerous cell growth in vitro. J. Med. Chem. 1995, 38, 735-738.
128. Bravo, H. R.; Copaja, S. V. Contents and morphological distribution of 2,4-dihydroxy-1,4-benzoxazin-3-one and 2-benzoxazolinone in Acanthus mollis in relation to protection from larvae of Pseudaletia impuncta. Ann. Appl. Biol. 2002, 140, 129-132.
129. Wilkes, M. A.; Marshall, D. R.; Copeland, L. Hydroxamic acids in cereal roots inhibit the growth of take-all. Soil Biol. Biochem. 1999, 31, 1831-1836.
130. Schulz, M.; Friebe, A.; Kuck, P.; Seipel, M.; Schnabl, H. Allelopathic effects of living quackgrass (Agropyrens repens L.). Identification of inhibitory allelochemicals exuded from rhizome borne roots. Ang. Bot. 1994, 68, 195-200.
131. Gianoli, E.; Niemeyer, H. M. Lack of costs of herbivory-induced defenses in a wild wheat: integration of physiological and ecological approaches. Oikos 1997, 80, 269-275.
132. Pethó, M. Occurrence of cyclic hydroxamic acids in the tissues of barnyard grass (Echinochloa crus-galli/L./P.B.), and their possible role in allelopathy. Acta Agron. Hung. 1993, 42, 197-202.
133. Friebe, A.; Schulz, M.; Kuck, P.; Schnabl, H. Phytotoxins from shoot extracts and root exudates of Agropyron repens seedlings. Phytochemistry 1995, 38, 1157-1159.
134. Virtanen, A. I.; Hietala, P. K. Precursors of benzoxazolinone in rye plants. I. Precursor II, the aglucone. Acta Chem. Scand. 1960, 14, 499-502.
135. Hofman, J.; Hofmanová, O. 1,4-Benzoxazine derivatives in plants. Eur. J. Biochem. 1969, 8, 109-112.
136. Leszczynski, B.; Dixon, A. F. G. Resistance of cereals to aphids: interaction between hydroxamic acids and the aphid Sitobion avenae. Ann. Appl. Biol. 1990, 117, 21-30.
137. Ebisui, K.; Ishihara, A.; Hirai, N.; Iwamura, H. Occurrence of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and a β-glucosidase specific for its glucoside in maize seedlings. Z. Naturforsch. C 1998, 53, 793-798.
138. Belz, R. G.; Hurle, K. Differential exudation of two benzoxazinoids - One of the determining factors for seedling allelopathy of Triticeae species. J. Agric. Food Chem. 2005, 53, 250-261.
139. Epstein, W. W.; Rowsemitt, C. N.; Berger, P. J.; Negus, N. C. Dynamics of 6-methoxybenzoxazolinone in winter wheat. Effects of photoperiod and temperature. J. Chem. Ecol. 1986, 12, 2011-2021.
140. Richardson, M. D.; Bacon, C. W. Cyclic hydroxamic acid accumulation in corn seedlings exposed to reduced water potentials before, during, and after germination. J. Chem. Ecol. 1993, 19, 1613-1624.
141. Mwaja, V. N.; Masiunas, J. B.; Weston, L. A. Effects of fertility on biomass, phytotoxicity, and allelochemical content of cereal rye. J. Chem. Ecol. 1995, 21, 81-96.
142. Nie, C. R.; Luo, S. M.; Lin, C. X.; Zeng, R. S.; Huang, J. H.; Wang, J. W. Status of DIMBOA and phenolic acids in transgenic Bt corn. Aust. J. Agric. Res. 2005, 56, 833-837.
143. Manuwoto, S.; Scriber, J. M. Neonate larval survival of European corn borers, Ostrinia nubilalis on high and low DIMBOA genotypes of maize: Effects of light intensity and degree of insect inbreeding. Agric. Ecosyst. Environ. 1985, 14, 221-236.
144. Åhman, I.; Johansson, M. Effect of light on DIMBOA-glucoside concentration in wheat (Triticum aestivum L.). Ann. Appl. Biol. 1994, 124, 569-574.
145. Bergvinson, D. J.; Arnason, J. T.; Hamilton, R. I.; Tachibana, S.; Towers, G. H. N. Putative role of photodimerized phenolic acids in maize resistance to Ostrinia nubilalis (Lepidoptera, Pyralidae). Environ. Entomol. 1994, 23, 1516-1523.
146. Bergvinson, D. J.; Larsen, J. S.; Arnason, J. T. Effect of light on changes in maize resistance against the European corn borer, Ostrinia nubilalis (Hübner). Can. Entomol. 1995, 127, 111-122.
147. Kato-Noguchi, H. Effect of light-irradiation on allelopathic potential of germinating maize. Phytochemistry 1999, 52, 1023-1027.
148. Gianoli, E.; Niemeyer, H. M. Environmental effects on the induction of wheat chemical defences by aphid infestation. Oecologia 1996, 107, 549-552.
149. Gianoli, E.; Niemeyer, H. M. Environmental effects on the accumulation of hydroxamic acids in wheat seedlings: the importance of plant growth rate. J. Chem. Ecol. 1997, 23, 543-551.
150. Oikawa, A.; Ishihara, A.; Hasegawa, M.; Kodama, O.; Iwamura, H. Induced accumulation of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) in maize leaves. Phytochemistry 2001, 56, 669-675.
151. Slesak, E.; Slesak, M.; Gabrys, B. Effect of methyl jasmonate on hydroxamic acid content, protease activity, and bird cherryoat aphid Rhopalosiphum padi (L.) probing behavior. J. Chem. Ecol. 2001, 27, 2529-2543.
152. Zheng, Y. Q.; Zhao, Y.; Liu, X. G.; Yao, J. R.; Dong, F. S. Chemical inducement of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) in wheat seedlings. Allelopathy J. 2008, 21, 263-271.
153. Blassioli Moraes, M. C.; Birkett, M. A.; Gordon-Weeks, R.; Smart, L. E.; Martin, J. L.; Pye, B. J.; Bromilow, R.; Pickett, J. A. cis-Jasmone induces accumulation of defence compounds in wheat, Triticum aestivum. Phytochemistry 2007, 69, 9-17.
154. Wang, J. W.; Xu, T.; Zhang, L. W.; Zhong, Z. M.; Luo, S. M. Effects of methyl jasmonate on hydroxamic acid and phenolic acid content in maize and its allelopathic activity to Echinochloa crusgalli (L.). Allelopathy J. 2007, 19, 161-169.
155. Oikawa, A.; Ishihara, A.; Iwamura, H. Induction of HDMBOAGlc accumulation and DIMBOA-Glc 4-O-methyltransferase by jasmonic acid in poaceous plants. Phytochemistry 2002, 61, 331-337.
156. Atkinson, J.; Arnason, J.; Campos, F.; Niemeyer, H. M.; Bravo, H. R. Synthesis and reactivity of cyclic hydroxamic acids. Resistance factors in the Gramineae. In Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J.,Eds.; American Chemical Society Symposium Series 504; American Chemical Society: Washington, DC, 1992; pp 349-360.
157. Copaja, S. V.; Bravo, H. R.; Niemeyer, H. M. Quantitation of N-(2-hydroxy-4-methoxy-phenyl)-glyoxylo-hydroxamic acid, a reactive intermediate in reactions of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one. J. Org. Chem. 1986, 51, 3542-3545.
158. Niemeyer, H. M.; Bravo, H. R.; Peña, G. F.; Corcuera, L. J. Decomposition of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, a hydroxamic acid from Gramineae. In Chemistryand Biology of Hydroxamic Acids; Kehl, H., Ed.; Karger, A.G.: Basel, 1982; pp 22-28.
159. Bravo, H. R.; Niemeyer, H. M. Decomposition in aprotic solvents of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one, a hydroxamic acid from cereals. Tetrahedron 1985, 21, 4983-4986.
160. Quiroz, A.; Niemeyer, H. M. Reaction of 7-substituted 4-hydroxyl-1,4-benzoxazin-3-ones in strongly acidic media. Heterocycles 1991, 32, 1681-1685.
161. Atkinson, J.; Morand, P.; Arnason, J. T.; Niemeyer, H. M.; Bravo, H. R. Analogues of the cyclic hydroxamic acid 2,4-dihydroxy-7-methoxy-1,4-benzoxazin- 3-one (DIMBOA): decomposition to benzoxazolinones and reaction with -mercaptoethanol. J. Org. Chem. 1991, 56, 1788-1800.
162. Bravo, H. R.; Niemeyer, H. M. Descomposition of 7-nitro-2,4-dihydroxy-1, 4-benzoxazin-3-one in aqueous solutions. Heterocycles 1991, 32, 1687-1691.
163. Argandoña, V. H.; Peña, G. F.; Niemeyer, H. M.; Corcuera, L. J. Effect of cysteine on stability and toxicity to aphids of a cyclic hydroxamic acid from Gramineae. Phytochemistry 1982, 21, 1573-1574.
164. Niemeyer, H. M.; Corcuera, L. J.; Pérez, F. J. Reaction of a cyclic hydroxamic acid from Gramineae with thiols. Phytochemistry 1982, 21, 2287-2289.
165. Pérez, F. J.; Niemeyer, H. M. The reduction of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one by thiols. Phytochemistry 1985, 24, 2963-2966.
166. Pérez, F. J.; Niemeyer, H. M. Reaction of DIMBOA with amines. Phytochemistry 1989, 28, 1831-1834.
167. Pérez, F. J.; Niemeyer, H. M. Reaction of DIMBOA, a resistance factor from cereals, with papain. Phytochemistry 1989, 28, 1597-1600.
168. Cuevas, L.; Niemeyer, H. M.; Pérez, F. J. Reaction of DIMBOA, a resistance factor from cereals, with α-chymotrypsin. Phytochemistry 1990, 29, 1429-1432.
169. Cuevas, L.; Niemeyer, H. M. Effect of hydroxamic acids from cereals on aphid cholinesterases. Phytochemistry 1993, 34, 983-985.
170. Queirolo, C. B.; Andreo, C. S.; Vallejos, R. H.; Niemeyer, H. M.; Corcuera, L. J. Effect of hydroxamic acids from Gramineae on adenosine 5'-triphosphate synthesis in chloroplasts. Plant Physiol. 1981, 68, 941-943.
171. Niemeyer, H. M.; Calcaterra, N. B.; Roveri, O. A. Inhibition of mitochondrial energy-linked reactions by 2,4-dihydroxy-7-methoxy-1,4-benzoxazin- 3-one (DIMBOA), a hydroxamic acid from Gramineae. Biochem. Pharmacol. 1986, 35, 3909-3914.
172. Massardo, F.; Zúñiga, G. E.; Pérez, L. M.; Corcuera, L. J. Effects of hydroxamic acids on electron transport and their cellular location in corn. Phytochemistry 1994, 35, 873-876.
173. González, L. F.; Rojas, M. C. Role of wall peroxidases in oat growth inhibition by DIMBOA. Phytochemistry 1999, 50, 931-937.
174. Hashimoto, Y.; Ishizaki, T.; Shudo, K. A multi-centered electrophile formed a unique bioactive cyclic hydroxamic acid, 4-hydroxy-7-methoxy-2H-1,4- benzoxazin-3-(4H)-one. Tetrahedron 1991, 47, 1837-1860.
175. Dubois, M.; Canadas, D.; Despres-Pernot, A. G.; Coste, C.; Pfohl-Leszkowicz, A. Oxygreen process applied on nongerminated and germinated wheat: role of hydroxamic acids. J. Agric. Food Chem. 2008, 56, 1116-1121.
176. Ishizaki, T.; Hashimoto, Y.; Shudo, K.; Okamoto, T. Reaction of 4-acetoxy-1,4-benzoxazin-3-one with DNA. A possible chemical mechanism for the antifungal and mutagenic activities. Tetrahedron Lett. 1982, 23, 4055-4056.
177. Buchmann, C. A.; Nersesyan, A.; Kopp, B.; Schauberger, D.; Darroudi, F.; Grummt, T.; Krupitza, G.; Kundi, M.; Schulte-Hermann, R.; Knasmueller, S. Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4- benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2). Cancer Lett. 2007, 246, 290-299.
178. Figueroa, C. C.; Loayza-Muro, R.; Niemeyer, H. M. Temporal variation of RAPD-PCR phenotype composition of the grain aphid Sitobion avenae (Hemiptera: Aphididae) on wheat: the role of hydroxamic acids. Bull. Entomol. Res. 2002, 92, 25-33.
179. Belz, R. G. Allelopathy in crop/weed interactionssan update. Pest Manag. Sci. 2007, 63, 308-326.
180. Barnes, J. P.; Putnam, A. R. Role of benzoxazinones in allelopathy by rye (Secale cereale L.). J. Chem. Ecol. 1987, 13, 889-906.
181. Barnes, J. P.; Putnam, A. R.; Burke, B. A.; Aasen, A. J. Isolation and characterization of allelochemicals in rye herbage. Phytochemistry 1987, 26, 1385-1390.
182. Tabaglio, V.; Gavazzi, C.; Schulz, M.; Marocco, A. Alternative weed control using the allelopathic effect of natural benzoxazinoids from rye mulch. Agron. Sustainable Dev. 2008, 28, 397-401.
183. Yenish, J. P.; Worsham, A. D.; Chilton, W. S. Disappearance of DIBOA-glucoside, DIBOA, and BOA from rye (Secale cereale L) cover crop residue. Weed Sci. 1995, 43, 18-20.
184. Burgos, N. R.; Talbert, R. E. Differential activity of allelochemicals from Secale cereale in seedling bioassays. Weed Sci. 2000, 48, 302-310.
185. Wu, H. W.; Haig, T.; Pratley, J.; Lemerle, D.; An, M. Biochemical basis for wheat seedling allelopathy on the suppression of annual ryegrass (Lolium rigidum). J. Agric. Food Chem. 2002, 50, 4567-4571.
186. Zheng, Y. Q.; Zhao, Y.; Dong, F. S.; Yao, J. R.; Hurle, K. Relationship of DIMBOA content in wheat seedlings and its resistance to plant pathogens. Allelopathy J. 2005, 15, 137-143.
187. Zhang, J.; Boone, L.; Kocz, R.; Zhang, C. H.; Binns, A. N.; Lynn, D. G. At the maize/Agrobacterium interface: natural factors limiting host transformation. Chem. Biol. 2000, 7, 611-621.
188. Einhellig, F. A. Interactions involving allelopathy in cropping systems. Agronomy J. 1996, 88, 886-893.
189. Wu, H.; Pratley, J.; Lemerle, D.; An, M. Crop cultivars with allelopathic capability. Weed Res. 1999, 39, 171-190.
190. Macías, F. A.; Oliveros-Bastidas, A.; Marín, D.; Castellano, D.; Simonet, A. M.; Molinillo, J. M. G. Degradation studies on benzoxazinoids. Soil degradation dynamics of 2,4-dihydroxy-7-methoxy-(2H) -1,4-benzoxazin-3(4H)-one (DIMBOA) and its degradation products, phytotoxic allelochemicals from Gramineae. J. Agric. Food Chem. 2004, 52, 6402-6413.
191. Macías, F. A.; Oliveros-Bastidas, A.; Marín, D.; Castellano, D.; Simonet, A. M.; Molinillo, J. M. G. Degradation studies on benzoxazinoids. Soil degradation dynamics of (2R)-2-O-β- Dglucopyranosyl-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and its degradation products, phytotoxic allelochemicals from gramineae. J. Agric. Food Chem. 2005, 53, 554-561.
192. Fomsgaard, I. S.; Mortensen, A. G.; Carlsen, S. C. K. Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicalssa review. Chemosphere 2004, 54, 1025-1038.
193. Gagliardo, R. W.; Chilton, W. S. Soil transformation of 2(3H)-benzoxazolone of rye into phytotoxic 2-amino-3H-phenoxazin-3-one. J. Chem. Ecol. 1992, 18, 1683-1691.
194. 2BOA into aminophenoxazinones. J. Chem. Ecol. 1993, 19, 2453-2461.
195. Fomsgaard, I. S.; Mortensen, A. G.; Idinger, J.; Coja, T.; Blümel, S. Transformation of benzoxazinones and derivatives and microbial activity in the test environment of soil ecotoxicological tests on Poecilus cupreus and Folsomia candida. J. Agric. Food Chem. 2006, 54, 1086-1092.
196. Etzerodt, T.; Mortensen, A. G.; Fomsgaard, I. S. Transformation kinetics of 6-methoxybenzoxazolin-2-one in soil. J. Environ. Sci. Health B 2008, 43, 1-7.
197. Understrup, A. G.; Ravnskov, S.; Hansen, H. C. B.; Fomsgaard, I. S. Biotransformation of 2-benzoxazolinone to 2-amino-(3H)-phenoxazin-3-one and 2-acetylamino-(3H)-phenoxazin-3-one in soil. J. Chem. Ecol. 2005, 31, 1205-1222.
198. Friebe, A.; Vilich, V.; Hennig, L.; Kluge, M.; Sicker, D. Detoxification of benzoxazolinone allelochemicals from wheat by Gaeumannomyces graminis var tritici, G. graminis var. graminis, G. graminis var. avenae, and Fusarium culmorum. Appl. Environ. Microbiol. 1998, 64, 2386-2391.
199. Yue, Q.; Bacon, C. W.; Richardson, M. D. Biotransformation of 2-benzoxazolinone and 6-methoxy-benzoxazolinone by Fusarium monilforme. Phytochemistry 1998, 48, 451-454.
200. Zikmundová, M.; Drandaroiv, K.; Bigler, L.; Hesse, M.; Werner, C. Biotransformation of 2-benzoxazolinone and 2-hydroxy-1,4-benzoxazin-3-one by endophytic fungi isolated from Aphelandra tetragona. Appl. Environ. Microbiol. 2002, 68, 4863-4870.
201. Richardson, M. D.; Bacon, C. W. Catabolism of 6-methoxybenzoxazolinone and 2-benzoxazolinone by Fusarium moniliforme. Mycologia 1995, 87, 510-517.
202. Vilich, V.; Lohndorf, B.; Sikora, R. A.; Friebe, A. Metabolism of benzoxazolinone allelochemicals from Zea mays by Fusarium subglutinans. Mycol. Res. 1999, 103, 1529-1532.
203. 3]-MBOA in soil. J. Agric. Food Chem. 2006, 54, 1075-1085.
204. Bacon, C. W.; Hinton, D. M. Use of Bacillus subtilis as an endophyte for the control of diseases caused by fungi. US Patent and Trademark Office, Patent number 5,994,117, November 30, 1999.
205. Bacon, C. W.; Hinton, D. M.; Glenn, A. E.; Macías, F. A.; Marín, D. Interactions of Bacillus mojavensis and Fusarium verticillioides with a benzoxazolinone (BOA) and its transformation product, APO. J. Chem. Ecol. 2007, 33, 1885-1897.
206. Sicker, D.; Hao, H.; Schultz, M. Benzoxazolin-2(3H)-ones: generation, effects and detoxification in the competition among plants. In Allelopathy: Chemistry and Mode of Action of Allelochemicals; Macías, F. A., Galindo, J. C. G., Molinillo, J. M. G., Cutler, H. G., Eds.; CRC Press: Boca Raton, 2003; pp 77-102.
207. Schultz, M.; Knop, M.; Kant, S.; Sicker, D.; Voloshchuk, N.; Gryganski, A. Detoxification of allelochemicals: the case of benzoxazolin-2(3H)-one (BOA). In Allelopathy: a Physiological Process with Ecological Implications; Reigosa, M. J., Pedrol, N., González, L., Eds.; Springer: Dordrecht, The Netherlands, 2006; pp 157-171.
208. Hofmann, D.; Knop, M.; Hao, H.; Hennig, L.; Sicker, D.; Schultz, M. Glucosides from MBOA and BOA detoxification by Zea mays and Portulaca oleracea. J. Nat. Prod. 2006, 69, 34-37.
209. Sicker, D.; Schneider, B.; Hennig, L.; Knop, M.; Schultz, M. Glycoside carbamates from benzoxazolin-2(3H)-one detoxification in extracts and exudates of corn roots. Phytochemistry 2001, 58, 819-825.
210. Baerson, S. R.; Sánchez-Moreiras, A.; Pedrol-Bonjoch, N.; Schultz, M.; Kagan, I. A.; Agarwal, A. K.; Reigosa, M. J.; Duke, S. O. Detoxification and transcriptome response in Arabidopsis seedlings exposed to the allelochemical benzoxazolin-2(3H)-one. J. Biol. Chem. 2005, 23, 21867-21881.
211. Macías, F. A.; Marín, D.; Oliveros-Bastidas, A.; Castellano, D.; Simonet, A. M.; Molinillo, J. M. G. Structure-activity relationships (SAR) studies of benzoxazinones, their degradation products and analogues. Phytotoxicity on standard target species (STS). J. Agric. Food Chem. 2005, 53, 538-548.
212. Macías, F. A.; Chinchilla, N.; Varela, R. M.; Oliveros-Bastidas, A.; Marín, D.; Molinillo, J. M. G. Structure-activity relationship studies of benzoxazinones and related compounds. Phytotoxicity on Echinochloa crus-galli (L.) p. Beauv. J. Agric. Food Chem. 2005, 53, 4373-4380.
213. Macías, F. A.; Marín, D.; Oliveros-Bastidas, A.; Castellano, D.; Simonet, A. M.; Molinillo, J. M. G. Structure-activity relationship (SAR) studies of benzoxazinones, their degradation products, and analogues. Phytotoxicity on problematic weeds Avena fatua L. and Lolium rigidum Gaud. J. Agric. Food Chem. 2006, 54, 1040-1048.
214. Mathiassen, S. K.; Kudsk, P.; Mogensen, B. B. Herbicidal effects of soil-incorporated wheat. J. Agric. Food Chem. 2006, 54, 1058-1063.
215. Jia, C. H.; Kudsk, P.; Mathiassen, S. K. Joint action of benzoxazinone derivatives and phenolic acids. J. Agric. Food Chem. 2006, 54, 1049-1057.
216. Saunders, M.; Kohn, L. M. Host-synthesized secondary compounds influence the in vitro interactions between fungal endophytes of maize. Appl. Environ. Microbiol. 2008, 74, 136-142.
217. Idinger, J.; Cop, T.; Blümel, S. Effects of the benzoxazoid DIMBOA, selected degradation products, and structure-related pesticides on soil organisms. Ecotoxicol. Environ. Safety 2006, 65, 1-13.
218. Fritz, J. I.; Braun, R. Ecotoxicological effects of benzoxazinone allelochemicals and their metabolites on aquatic nontarget organisms. J. Agric. Food Chem. 2006, 54, 1105-1110.
219. Lo Piparo, E.; Smiesko, M.; Mazzatorta, P.; Benfenati, E.; Idinger, J.; Blumel, S. Preliminary analysis of toxicity of benzoxazinones and their metabolites for Folsomia candida. J. Agric. Food Chem. 2006, 54, 1099-1104.
220. Lo Piparo, E.; Fratev, F.; Lemke, F.; Mazzatorta, P.; Smiesko, M.; Fritz, J. I.; Benfenati, E. QSAR models for Daphnia magna toxicity prediction of benzoxazinone allelochemicals and their transformation products. J. Agric. Food Chem. 2006, 54, 1111-1115.
221. Jabeen, R.; Yamada, K.; Shigemori, H.; Hasegawa, T.; Hara, M.; Kuboi, T.; Hasegawa, K. Induction of β-glucosidase activity in maize coleoptiles by blue light illumination. J. Plant Physiol. 2006, 163, 538-545.
222. Hasegawa, T.; Yamada, K.; Shigemori, H.; Miyamoto, K.; Ueda, J.; Hasegawa, K. Isolation and identification of phototropismregulating substances benzoxazinoids from maize coleoptiles. Heterocycles 2004, 63, 2707-2712.
223. Jabeen, R.; Yamada, K.; Hasegawa, T.; Minami, E.; Shigemori, H.; Hasegawa, K. Direct involvement of benzoxazinoids in the growth suppression induced by phototropic stimulation in maize coleoptiles. Heterocycles 2007, 71, 523-529.
224. Burgos, N. R.; Talbert, R. E.; Kim, K. S.; Kuk, Y. I. Growth inhibition and root ultrastructure of cucumber seedlings exposed to allelochemicals from rye (Secale cereale). J. Chem. Ecol. 2004, 30, 671-689.
225. +-ATPase. Phytochemistry 1997, 44, 979-983.
226. Macías, F. A.; Maríun, D.; Oliveros-Bastidas, A.; Molinillo, J. M. G. Optimization of benzoxazinones as natural herbicide models by lipophilicity enhancement. J. Agric. Food Chem. 2006, 54, 9357-9365.
227. Macías, F. A.; De Siqueira, J. M.; Chinchilla, N.; Marín, D.; Varela, R. M.; Molinillo, J. M. G. New herbicide models from benzoxazinones: aromatic ring functionalization effects. J. Agric. Food Chem. 2006, 54, 9843-9851.
228. Klun, J. A.; Tipton, C. L.; Brindley, T. A. 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. 1967, 60, 1529-1533.
229. Guthrie, W. D.;Wilson, R. L.; Coats, J. R.; Robbins, J. C.; Tseng, C. T.; Jarvis, J. L.; Russell, W. A. European corn borer (Lepidoptera: Pyralidae) leaf-feeding resistance and DIMBOA content in inbred lines of dent maize grown under field versus greenhouse conditions. J. Econ. Entomol. 1986, 79, 1492-1496.
230. Barry, D.; Alfaro, D.; Darrah, L. L. Relation of European corn borer leaf-feeding resistance and DIMBOA content in maize. Environ. Entomol. 1994, 23, 177-182.
231. Reid, L. M.; Arnason, J. T.; Nozzolillo, C.; Hamilton, R. I. Laboratory and field-resistance to the European corn borer in maize germplasm. Crop Sci. 1991, 31, 1496-1502.
232. Robinson, J. F.; Klun, J. A.; Brindley, T. A. European corn borer: a non-preference mechanism of leaf feeding resistance and its relationship to 1,4-benzoxazin-3-one concentration in dent corn tissue. J. Econ. Entomol. 1978, 71, 461-465.
233. Campos, F.; Atkinson, J.; Arnason, J. T.; Philogène, B. J. R.; Morand, P.; Werstiuk, N. H.; Timmins, G. Toxicity and toxicokinetics of 6-methoxybenzoxazolinone (MBOA) in the European corn borer, Ostrinia nubilalis (Hübner). J. Chem. Ecol. 1988, 14, 989-1002.
234. Houseman, J. G.; Campos, F.; Thie, N. M. R.; Philogène, B. J. R.; Atkinson, J.; Morand, P.; Arnason, J. T. Effect of the maizederived compounds DIMBOA and MBOA on growth and digestive processes of European corn borer (Lepidoptera, Pyralidae). J. Econ. Entomol. 1992, 85, 669-674.
235. Barry, D.; Darrah, L. L. Effect of research on commercial hybrid maize resistance to European corn borer (Lepidoptera: Pyralidae). J. Econ. Entomol. 1991, 84, 1053-1059.
236. Rojanaridpiched, C.; Gracen, V. E.; Everett, H. L.; Coors, J. G.; Pugh, B. F.; Bouthyette, P. Multiple factor resistance in maize to European corn borer. Maydica 1984, 29, 305-315.
237. Bergvinson, D. J.; Hamilton, R. I.; Arnason, J. T. Leaf profile of maize resistance factors to European corn borer, Ostrinia nubilalis. J. Chem. Ecol. 1995, 21, 343-354.
238. Mao, J. Q.; Burt, A. J.; Ramputh, A. I.; Simmonds, J.; Cass, L.; Hubbard, K.; Miller, S.; Altosaar, I.; Arnason, J. T. Diverted secondary metabolism and improved resistance to european corn borer (Ostrinia nubilalis) in maize (Zea mays L.) transformed with wheat oxalate oxidase. J. Agric. Food Chem. 2007, 55, 2582-2589.
239. Feng, R.; Houseman, J. G.; Downe, A. E. R.; Atkinson, J.; Arnason, J. T. Effects of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 6-methoxybenzoxazolinone (MBOA) on the detoxification processes in the larval midgut of the European corn borer. Pest. Biochem. Physiol. 1992, 44, 147-154.
240. Givovich, A.; Niemeyer, H. M. Effect of hydroxamic acids on feeding behaviour and performance of cereal aphids on wheat. Eur. J. Entomol. 1994, 91, 371-374.
241. Nicol, D.; Wratten, S. D. The effect of hydroxamic acid concentration at late growth stages of wheat on the performance of the aphid Sitobion avenae. Ann. Appl. Biol. 1997, 130, 387-396.
242. Gianoli, E.; Papp, M.; Niemeyer, H. M. Costs and benefits of hydroxamic acids-related resistance in winter wheat against the bird cherry-oat aphid, Rhopalosiphum padi L. Ann. Appl. Biol. 1996, 129, 83-90.
243. Morse, S.; Wratten, S. D.; Edwards, P. J.; Niemeyer, H. M. The effect of maize leaf damage on the survival and growth rate of Rhopalosiphum padi. Ann. Appl. Biol. 1991, 119, 251-256.
244. Bruce, T. J. A.; Martin, L. J.; Pickett, J. A.; Pye, B. J.; Smart, L. E.; Wadhams, L. J. cis-Jasmone treatment induces resistance in wheat plants against the grain aphid, Sitobion avenae (Fabricius) (Homoptera: Aphididae). Pest Manag. Sci. 2003, 59, 1031-1036.
245. Corcuera, L. J.; Queirolo, C. B.; Argandoña, V. H. Effects of 2-β-D-glucosyl-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one on Schizaphis graminum (Rondani) (Insecta, Aphididae) feeding on artificial diets. Experientia 1985, 41, 514-516.
246. Givovich, A.; Niemeyer, H. M. Comparison of the effect of hydroxamic acids from wheat on five species of cereal aphids. Entomol. Exp. Appl. 1995, 74, 115-119.
247. Cambier, V.; Hance, T.; de Hoffmann, E. Effects of 1,4-benzoxazin-3-one derivatives from maize on survival and fecundity of Metopolophium dirhodum (Walker) on artificial diet. J. Chem. Ecol. 2001, 27, 359-370.
248. Bing, J. W.; Guthrie, W. D.; Dicke, F. F.; Obrycki, J. J. Relation of corn leaf aphid (Homoptera: Aphididae) colonization to DIMBOA content in maize inbred lines. J. Econ. Entomol. 1990, 83, 1626-1632.
249. Kazemi, M. H.; van Emden, H. E. Partial antibiosis to Rhopalosiphum padi in wheat and some phytochemical correlations. Ann. Appl. Biol. 1992, 121, 1-9.
250. Gianoli, E.; Caillaud, C. M.; Chaubet, B.; DiPietro, J. P.; Niemeyer, H. M. Variability in grain aphid (Homoptera: Aphididae) performance and aphid-induced phytochemical responses in wheat. Environ. Entomol. 1997, 26, 638-641.
251. Figueroa, C. C.; Simon, J. C.; Le Gallic, J. F.; Prunier-Leterme, N.; Briones, L. M.; Dedryver, C. A.; Niemeyer, H. M. Effect of host defense chemicals on clonal distribution and performance of different genotypes of the cereal aphid Sitobion avenae. J. Chem. Ecol. 2004, 30, 2515-2525.
252. Tjallingii, W. F. Electronic recording of penetration behaviour by aphids. Entomol. Exp. Appl. 1978, 24, 721-730.
253. Walker, G. P., Backus, E. A., Eds. Principles and Applications of Electronic Monitoring and Other Techniques in the Study of Homopteran Feeding Behavior; Thomas Say Publications in Entomology: Lanham, MD, 2000.
254. Givovich, A.; Niemeyer, H. M. Role of hydroxamic acids in the resistance of wheat to the Russian wheat aphid Diuraphis noxia (Mordvilko) (Hom, Aphididae). J. Appl. Entomol. 1996, 120, 537-539.
255. Mayoral, A. M.; Tjallingii, W. F.; Castañera, P. Probing behaviour of Diuraphis noxia on five cereal species with different hydroxamic acid levels. Entomol. Exp. Appl. 1996, 78, 341-348.
256. Ramírez, C. C.; Niemeyer, H. M. Salivation into sieve elements in relation to plant chemistry: the case of the aphid Sitobion fragariae and the wheat, Triticum aestivum. Entomol. Exp. Appl. 1999, 91, 111-114.
257. Ramírez, C. C.; Olea, N.; Niemeyer, H. M. Pattern of cell punctures by the aphid Sitobion fragariae (Sternorrhyncha: Aphididae) and cell arrangement in the leaf tissues of wheat, Triticum aestivum. Eur. J. Entomol. 1999, 96, 73-75.
258. Ramírez, C. C.; Caballero, P. P.; Niemeyer, H. M. Effect of previous exposure to hydroxamic acids in probing behavior of aphid Sitobion fragariae on wheat seedlings. J. Chem. Ecol. 1999, 25, 771-779.
259. Givovich, A.; Niemeyer, H. M. Hydroxamic acids affecting barley yellow dwarf virus transmission by the aphid Rhopalosiphum padi. Entomol. Exp. Appl. 1991, 59, 79-85.
260. Bing, J. W.; Novak, M. G.; Obrycki, J. J.; Guthrie, W. D. Stylet penetration and feeding sites of Rhopalosiphum maidis (Homoptera: Aphididae) on two growth stages of maize. Ann. Entomol. Soc. Am. 1991, 84, 549-554.
261. Givovich, A.; Morse, S.; Cerda, H.; Niemeyer, H. M.; Wratten, S. D.; Edwards, P. J. Hydroxamic acid glucosides in honeydew of aphids feeding on wheat. J. Chem. Ecol. 1992, 18, 841-846.
262. Niemeyer, H. M.; Givovich, A.; Copaja, S. V. Hydroxamic acids: chemical defences in wheat against aphids. In Pest Control and Sustainable Agriculture; Corey, S. A., Dall, D. J., Milne, W. M., Eds.; CSIRO Publications: Collingwood, Australia, 1993; pp 37-41.
263. Leszczynski, B.; Matok, H.; Dixon, A. F. G. Resistance of cereals to aphids: the interaction between hydroxamic acid and UDPglucose transferases in the aphid Sitobion avenae (Homoptera: Aphididae). J. Chem. Ecol. 1992, 18, 1189-1200.
264. Mukanganyama, S.; Figueroa, C. C.; Hasler, J. A.; Niemeyer, H. M. Effects of DIMBOA on detoxification enzymes of the aphid Rhopalosiphum padi (Homoptera: Aphididae). J. Insect Physiol. 2003, 49, 223-229.
265. Leszczynski, B.; Dixon, A. F. G. Resistance of cereals to aphids - The interaction between hydroxamic acids and glutathione S-transferases in the grain aphid Sitobion avenae (F) (Hom, Aphididae). J. Appl. Entomol. 1992, 113, 61-67.
266. Figueroa, C. C.; Koenig, C.; Araya, C.; Santos, M. J.; Niemeyer, H. M. Effect of DIMBOA, a hydroxamic acid from cereals, on peroxisomal and mitochondrial enzymes from aphids: evidence for the presence of peroxisomes in aphids. J. Chem. Ecol. 1999, 25, 2465-2475.
267. Loayza-Muro, R.; Figueroa, C. C.; Niemeyer, H. M. Effect of two wheat cultivars differing in hydroxamic acid concentration on detoxification metabolism in the aphid Sitobion avenae. J. Chem. Ecol. 2000, 26, 2725-2736.
268. Escobar, C. A.; Sicker, D.; Niemeyer, H. M. Evaluation of DIMBOA analogs as antifeedants and antibiotics towards the aphid Sitobion avenae in artificial diets. J. Chem. Ecol. 1999, 25, 1543-1554.
269. Bravo, H. R.; Copaja, S. V.; Argandoña, V. H. Chemical basis for the antifeedant activity of natural hydroxamic acids and related compounds. J. Agric. Food Chem. 2004, 52, 2598-2601.
270. Nicol, D.; Wratten, S. D.; Eaton, N.; Copaja, S. V. Effects of DIMBOA levels in wheat on the susceptibility of the grain aphid (Sitobion avenae) to deltamethrin. Ann. Appl. Biol. 1993, 122, 427-433.
271. Gutiérrez, C.; Castañera, P. Efecto de los tejidos de maíz con alto y bajo contenido en DIMBOA sobre la biología del taladro Sesamia nonagrioides Lef. (Lepidoptera, Noctuidae). Invest. Agrar.: Prod. Prot. Veg. 1986, 1, 109-119.
272. Ortego, F.; Ruiz, M.; Castañera, P. Effect of DIMBOA on growth and digestive physiology of Sesamia nonagrioides (Lepidoptera: Noctuidae) larvae. J. Insect Physiol. 1998, 44, 95-101.
273. Yan, F.; Liang, X.; Zhu, X. The role of DIMBOA on the feeding of Asian corn borer, Ostrinia furnacalis (Guenée) (Lep., Pyralidae). J. Appl. Entomol. 1999, 123, 49-53.
274. Yan, F. M.; Xu, C. G.; Li, S. G.; Lin, C. S.; Li, J. H. Effects of DIMBOA on several enzymatic systems in Asian corn borer, Ostrinia furnacalis (Guenée). J. Chem. Ecol. 1995, 21, 2047-2056.
275. Manuwoto, S.; Scriber, J. M. Consumption and utilization of three maize genotypes by the Southern armyworm. J. Econ. Entomol. 1982, 75, 163-167.
276. Manuwoto, S.; Scriber, J. M. Consumption and utilization of experimentally altered corn by southern armyworm: iron, nitrogen, and cyclic hydroxamates. J. Chem. Ecol. 1985, 11, 1469-1483.
277. Rostás, M. The effects of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin- 3-one on two species of Spodoptera and the growth of Setosphaeria turcica in vitro. J. Pest Sci. 2007, 80, 35-41.
278. Hedin, P. A.; Davis, F. M.; Williams, W. P. 2-Hydroxy-4,7-dimethoxy-1,4- benzoxazin-3-one, a possible toxic factor in corn to the Southwestern corn borer. J. Chem. Ecol. 1993, 19, 531-542.
279. Assabgui, R. A.; Arnason, J. T.; Hamilton, R. I. Field evaluations of hydroxamic acids as antibiosis factors in elite maize inbreds to the Western corn rootworm (Coleoptera: Chrysomelidae). J. Econ. Entomol. 1995, 88, 1482-1493.
280. Assabgui, R. A.; Hamilton, R. I.; Arnason, J. T. Hydroxamic acid content and plant development of maize (Zea mays L) in relation to damage by the western corn rootworm, Diabrotica virgifera virgifera LeConte. Can. J. Plant Sci 1995, 75, 851-856.
281. Xie, Y. S.; Arnason, J. T.; Philogène, B. J. R.; Atkinson, J.; Morand, P. Behavioral responses of western corn rootworm larvae to naturally occurring and synthetic hydroxamic acids. J. Chem. Ecol. 1992, 18, 945-957.
282. Davis, C. S.; Ni, X. Z.; Quisenberry, S. S.; Foster, J. E. Identification and quantification of hydroxamic acids in maize seedling root tissue and impact on western corn rootworm (Coleoptera: Chrysomelidae) larval development. J. Econ. Entomol. 2000, 93, 989-992.
283. Abel, C. A.; Berhow, M. A.; Wilson, R. L.; Binder, B. F.; Hibbard, B. E. Evaluation of conventional resistance to European corn borer (Lepidoptera: Crambidae) and western corn rootworm (Coleoptera: Chrysomelidae) in experimental maize lines developed from a backcross breeding program. J. Econ. Entomol. 2000, 93, 1814-1821.
284. Long, B. J.; Dunn, G. M.; Routley, D. G. Relationship of hydroxamate concentration in maize and field reaction to Helmisthosporium turcicum. Crop Sci. 1978, 18, 573-575.
285. Tóth Toldi, E. Relationship between DIMBOA content and Helmisthosporium turcicum resistance in maize. Novenytermeles 1984, 33, 213-218.
286. Couture, R. M.; Routley, D. G.; Dunn, G. M. Role of hydroxamic acids in monogenic resistance of maize to Helmisthosporium turcicum. Physiol. Plant Pathol. 1971, 1, 515-521.
287. Kostandi, S. F.; Koraiem, Y. S.; Kamara, A.; Omar, M. A. Effect of phenols in host-pathogen interaction of maize (Zea mays L.)-Cephalosporium maydis system. Agrochimica 1981, 25, 367-375.
288. ElNaghy, M. A.; Linko, P. The role of 4-O-glucosyl-2,4-dihydroxy-7- methoxy-1,4-benzoxazin-3-one in resistance of wheat to stem rust. Physiol. Plant. 1962, 15, 764-771.
289. ElNaghy, M. A.; Shaw, M. Correlation between resistance to stem rust and the concentration of a glucoside in wheat. Nature 1966, 210, 417-418.
290. Søltoft, M.; Jørgensen, L. N.; Svensmark, B.; Fornsgaard, I. S. Benzoxazinoid concentrations show correlation with Fusarium Head Blight resistance in Danish wheat varieties. Biochem. Syst. Ecol. 2008, 36, 245-259.
291. Lyons, P. C.; Nicholson, R. L. Evidence that cyclic hydroxamate concentrations are not related to resistance of corn leaves to anthracnose. Can. J. Plant Pathol. 1989, 11, 215-220.
292. Glenn, A. E.; Gold, S. E.; Bacon, C. W. Fdb1 and Fdb2, Fusarium verticillioides loci necessary for detoxification of preformed antimicrobials from corn. Mol. Plant-Microbe Interact. 2002, 15, 91-101.
293. Simmons, C. R.; Grant, S.; Altier, D. J.; Dowd, P. F.; Crasta, O.; Folkerts, O.; Yalpani, N. Maize rhm1 resistance to Bipolaris maydis is associated with few differences in pathogenesis-related proteins and global mRNA profiles. Mol. Plant-Microbe Interact. 2001, 14, 947-954.
294. Donoso, E. P.; Bustamante, R. O.; Carú, M.; Niemeyer, H. M. Water deficit as a driver of the mutualistic relationship between the fungus Trichoderma harzianum and two wheat genotypes. Appl. Environ. Microbiol. 2008, 74, 1412-1417.
295. Bücker, C.; Grambow, H. J. Alterations in 1,4-benzoxazinone levels following inoculation with stem rust in wheat leaves carrying various alleles for resistance and their possible role as phytoalexins in moderately resistant leaves. Z. Naturforsch. C 1990, 45, 1151-1155.
296. Weibull, J.; Niemeyer, H. M. Changes of DIMBOA-Glc content in wheat plants upon infection by three plant pathogenic fungi. Physiol. Mol. Plant Pathol. 1995, 47, 201-212.
297. Oikawa, A.; Ishihara, A.; Tanaka, C.; Mori, N.; Tsuda, M.; Iwamura, H. Accumulation of HDMBOA-Glc is induced by biotic stresses prior to the release of MBOA in maize leaves. Phytochemistry 2004, 65, 2995-3001.
298. Basse, C. W. Dissecting defense-related and developmental transcriptional responses of maize during Ustilago maydis infection and subsequent tumor formation. Plant Physiol. 2005, 138, 1774-1784.
299. Glenn, A. E.; Hinton, D. M.; Yates, I. E.; Bacon, C. W. Detoxification of corn antimicrobial compounds as the basis for isolating Fusarium verticilloides and some other Fusarium species from corn. Appl. Environ. Microbiol. 2001, 67, 2973-2981.
300. Niemeyer, H. M.; Pesel, E.; Copaja, S. V.; Bravo, H. R.; Franke, S.; Francke, W. Changes in hydroxamic acid levels of wheat plants induced by aphid feeding. Phytochemistry 1989, 28, 447-449.
301. Gianoli, E.; Niemeyer, H. M. Characteristics of hydroxamic acid induction in wheat triggered by aphid infestation. J. Chem. Ecol. 1997, 23, 2695-2705.
302. Gutiérrez, C.; Castañera, P.; Torres, V. Wound-induced changes in DIMBOA (2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one) concentration in maize plants caused by Sesamia nonagrioides (Lepidoptera, Noctuidae). Ann. Appl. Biol. 1988, 113, 447-454.
303. Huang, C. H.; Wang, X. Y.; Wang, R. J.; Xue, K.; Yan, F. M.; Xu, C. R. Distribution and variations of three 1,4-benzoxazin-3-ones in maize induced by the Asian corn borer, Ostrinia furnacalis (Guenée). Z. Naturforsch. C 2006, 61, 257-262.
304. Collantes, H. G.; Gianoli, E.; Niemeyer, H. M. Effect of defoliation on the patterns of allocation of a hydroxamic acid in rye (Secale cereale). Environ. Exp. Bot. 1997, 38, 231-235.
305. Collantes, H. G.; Gianoli, E.; Niemeyer, H. M. Defoliation affects chemical defenses in all plant parts of rye seedlings. J. Chem. Ecol. 1999, 25, 491-499.
306. Collantes, H. G.; Gianoli, E.; Niemeyer, H. M. Changes in growth and chemical defences upon defoliation in maize. Phytochemistry 1998, 49, 1921-1923.
307. Persans, M. W.; Wang, J.; Schuler, M. A. Characterization of maize cytochrome P450 monooxygenases induced in response to safeners and bacterial pathogens. Plant Physiol. 2001, 125, 1126-1138.
308. Martos, A.; Givovich, A.; Niemeyer, H. M. Effect of DIMBOA, an aphid resistance factor in wheat, on the aphid predator Eriopis connexa Germar (Coleoptera: coccinellidae). J. Chem. Ecol 1992, 18, 469-479.
309. Fuentes-Contreras, E.; Niemeyer, H. M. DIMBOA glucoside, a wheat chemical defense, affects host acceptance and suitability of Sitobion avenae to the cereal aphid parasitoid Aphidius rhopalosiphi. J. Chem. Ecol. 1998, 24, 371-381.
310. Fuentes-Contreras, E.; Niemeyer, H. M. Effect of wheat resistance, the parasitoid Aphidius rhopalosiphi, and the entomopathogenic fungus Pandora neoaphidis, on population dynamics of the cereal aphid Sitobion avenae. Entomol. Exp. Appl. 2000, 97, 109-114.
311. Campos, F.; Donskov, N.; Arnason, J. T.; Philogène, B. J. R.; Atkinson, J.; Morand, P.; Werstiuk, N. H. Biological effects and toxicokinetics of DIMBOA in Diadegma terebrans (Hymenoptera: Ichneumonidae), an endoparasitoid of Ostrinia nubilalis (Lepidoptera: Pyralidae). J. Econ. Entomol. 1990, 83, 356-360.
312. McBride, R. G.; Mikkelsen, R. L.; Barker, K. R. The role of low molecular weight organic acids from decomposing rye in inhibiting root-knot nematode populations in soil. Appl. Soil Ecol. 2000, 15, 243-251.
313. McBride, R. G.; Mikkelsen, R. L.; Barker, K. R. Survival and infection of root-knot nematodes added to soil amended wih rye at different stages of decomposition and cropped with cotton. Appl. Soil Ecol. 1999, 13, 231-235.
314. Zasada, I. A.; Meyer, S. L. F.; Halbrendt, J. M.; Rice, C. Activity of hydroxamic acids from Secale cereale against the plantparasitic nematodes Meloidogyne incognita and Xiphinema americanum. Phytopathology 2005, 95, 1116-1121.
315. Zasada, I. A.; Rice, C. P.; Meyer, S. L. F. Improving the use of rye (Secale cereale) for nematode management: potential to select cultivars based on Meloidogyne incognita host status and benzoxazinoid content. Nematology 2007, 9, 53-60.
316. Timper, P.; Krakowsky, M. D.; Snook, M. E. Resistance in maize to Paratrichodorus minor. Nematropica 2007, 37, 9-20.
317. Shimabukuro, R. H.; Swanson, H. R.; Walsh, W. C. Glutathione conjugation. Atrazine detoxification mechanism in corn. Plant Physiol. Biochem. 1970, 46, 103-107.
318. Siminszky, B. Plant cytochrome P450-mediated herbicide metabolism. Phytochem. Rev. 2006, 5, 445-458.
319. Cherifi, M.; Raveton, M.; Picciocchi, A.; Ravanel, P.; Tissut, M. Atrazine metabolism in corn seedlings. Plant Physiol. Biochem. 2001, 39, 665-672.
320. Wenger, K.; Bigler, L.; Suter, M. J. F.; Schonenberger, R.; Gupta, S. K.; Schulin, R. Effect of corn root exudates on the degradation of atrazine and its chlorinated metabolites in soils. J. Environ. Qual. 2005, 34, 2187-2196.
321. Marcacci, S.; Raveton, M.; Ravanel, P.; Schwitzguebel, J. P. The possible role of hydroxylation in the detoxification of atrazine in mature vetiver (Chrysopogon zizanioides Nash) grown in hydroponics. Z. Naturforsch. C 2005, 60, 427-434.
322. Raveton, M.; Ravanel, P.; Kaouadji, M.; Bastide, J.; Tissut, M. The chemical transformation of atrazine in corn seedlings. Pest. Biochem. Physiol. 1997, 58, 199-208.
323. Dabed, R. G.; Toral, M. I.; Corcuera, L. J.; Niemeyer, H. M. Complexes of bivalent cations with a hydroxamic acid from maize extracts. Polyhedron 1983, 2, 106-108.
324. Hiriart, M. V.; Corcuera, L. J.; Andrade, C.; Crivelli, I. Copper (II) complexes of a hydroxamic acid from maize. Phytochemistry 1985, 24, 1919-1922.
325. Poschenrieder, C.; Tolra, R. P.; Barceló, J. A role for cyclic hydroxamates in aluminium resistance in maize. J. Inorg. Biochem. 2005, 99, 1830-1836.
326. Sahi, S. V.; Chilton, M.-D.; Chilton, W. S. Corn metabolites affect growth and virulence of Agrobacterium tumefaciens. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 3879-3883.
327. Mohamalawari, D.; Sharma, N. C.; Cristae, P.; Sahi, S. V. Transformation of maize by 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one resistant Agrobacterium strains. Biotech. Lett. 2002, 24, 197-203.