Role of natural benzoxazinones in the survival strategy of plants

International Review of Cytology

Volumn 198, Issue , 2000, Pages 319-346

  Sicker, Dieter ^a   Frey, Monika ^b   Schulz, Margot ^c   Gierl, Alfons ^b  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c UNIVERSITY OF BONN   (Germany)

Author keywords

Acetal glucosides; Allelopathy; Benzoxazinones; Biosynthesis; Cyclic hydroxamic acids; Defence

Indexed keywords

BENZOXAZINE DERIVATIVE; GLUCOSIDE; PESTICIDE;

CEREAL; CROP; INFECTION; MAIZE; NONHUMAN; PHYTOCHEMISTRY; PLANT GROWTH; PRIORITY JOURNAL; REVIEW; WHEAT;

HEXAPODA; POACEAE; SECALE CEREALE; TRITICUM AESTIVUM; ZEA MAYS;

EID: 0034014079     PISSN: 00747696     EISSN: None     Source Type: Book Series    
DOI: 10.1016/s0074-7696(00)98008-2     Document Type: Review

References (114)

1. Argandona, V. H., Corcuera, L. J., Niemeyer, H. M., and Campbell, B. C. (1983). Toxicity and feeding deterrency of hydroxamic acids from Gramineae in synthetic diets against the greenbug Shizaphis graminum. Entomol. Exp. Appl. 34, 134-138.
2. Atkinson, J., Morand, P., Arnason, J. T., Niemeyer, H. M., and Bravo, H. R. (1991). Analogues of the cyclic hydroxamic acid 2,4-dihydroxy-2H-1,4-benzoxazin-3-one: Decomposition to benzoxazolinones and reaction with b-mercaptoethanol. J. Org. Chem. 56, 1788-1800.
3. Babcock, G. D., and Esen, A. (1994). Substrate specifity of maize b-glucosidase. Plant Sci. 101, 31-39.
4. Bailey, B. A., and Larson, R. L. (1991). Maize microsomal benzoxazinone N-monooxygenase. Plant Physiol. 95, 792-796.
5. Barnes, J. P., and Putnam, A. R. (1987). Role of benzoxazinones in allelopathy by rye (Secale cereale L.) J. Chem. Ecol. 13, 889-906.
6. Barnes, J. P., Putnam, A. R., and Burke, B. A. (1986). Allelopathic activity of rye (Secale cereale L.). In: "The Science of Allelopathy" (A. R. Putnam and C. S. Tang, Eds.), pp. 271-286. Wiley and sons, New York.
7. Barria, B. N., Copaja, S. V., and Niemeyer, H. M. (1992). Occurence of DIBOA in wild Hordeum species and its relation to aphid resistance. Phytochemistry 31, 89-91.
8. Barry D., Alfaro D., and Darrah L. L. (1994). Relation of European Corn borer (Lepidoptera : Pyralidae) Leaf Feeding resistance and DIMBOA content in maize. Environ. Entomol. 23, 177-182.
9. Bravo, H. R., and Lazo, W. (1993). Antimicrobal activity of cereal hydroxamic acids and related compounds. Phytochemistry 33, 569-571.
10. Bravo, H. R., and Lazo, W. (1996). Antialgal and antifungal activity of natural hydroxamic acids and related compounds. J. Agric. Food Chem. 44, 1569-1571.
11. Bravo, H. R., Copaja, S. V., and Lazo, W. (1997). Antimicrobal activity of natural 2-benzoxazolinones and related derivatives. J. Agric. Food Chem. 45, 3255-3257.
12. Campos, F., Atkinson, J., Arnason, J. T., Philogène B. J. R., Morand, P., Werstiuk, N. H., and Timmins, G. (1989). Toxicokinetics of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) in the European corn borer, Ostrinia nubilalis (Hübner). J. Chem. Ecol. 15, 1989-1994.
13. Chase, W. R., Nair, M. G., and Putnam, A. R. (1991). 2,2′-Oxo-1,1′-azobenzene: Selective toxicity of rye (Secale cereale L.) allelochemicals to weed and crop species: II. J. Chem. Ecol. 17, 9-18.
14. Chatterjee, A., Sharma, N. J., Basserji, J., and Basa, S. C. (1990). Studies and Acanthaceae - Benzoxazine glucoside and benzoxazolone from Blepharis edulis Pers. Ind. J. Chem. 29B, 132-134.
15. Chen, C. M., and Chen, M. T. (1976). 6-Methoxybenzoxazolinone and triterpenoids from roots of Scoparia dulcis. Phytochemislry 15, 1997-1999.
16. Chomet, P. (1994). Transposon tagging with Mutator. In "The Maize Handbook" (M. Freeling and V. Walbot, Eds.), pp. 243-249. Springer Verlag, New York.
17. Cicek, M., and Esen, A. (1998). Structure and expression of a dhurrinase (beta-glucosidase) from sorghum. Plant Physiol. 116, 1469-1478.
18. Copaja S.V., Barria B. N., and Niemeyer H. M. (1991a). Hydroxamic acid content of perennial triticeae. Phytochemistry 30, 1531-1534.
19. Copaja, S. V., Niemeyer, H. M., and Wratten, S. D. (1991b). Hydroxamic acid levels in Chilean and British wheat seedlings. Ann. Appl. Biol. 118, 223-227.
20. Creighton, T. E., and Yanofsky, C. (1966). Association of the alpha and beta subunits of the tryptophan synthase of Escherichia coli. J. Biol. Chem. 241, 980-990.
21. Cuevas, L., and Niemeyer, H. M. (1993). Effect of hydroxamic acids from cereals on aphid cholinesterases. Phytochemistry 34, 983-985.
22. Cuevas, L., Niemeyer, H. M., and Perez, F. J. (1990). Reaction of DIMBOA, a resistance factor from cereals, with a-chymotrypsin. Phytochemistry 29, 1429-1432.
23. Devos, K. M., and Gale, M. D. (1997). Comparative genetics in the grasses. Plant Mol. Biol. 35, 3-15.
24. Desai S. R., Kumar P., and Chilton, W. S. (1996). Indole is an intermediate in the biosynthesis of cyclic hydroxamic acids in maize. Chem. Commun. 1321.
25. Esen, A. (1992). Purification and partial characterization of maize (Zea mays L.) b-glucosidase. Plant Physiol. 98, 174-182.
26. Fielder, D. A., Collins, F. W., Blackwell, B. A., Bensimon, C., and ApSimon, J. W. (1994). Isolation and characterization of 4-acetyl-benzoxazolin-2-one (4-ABOA), a new benzoxazolinone from Zea mays. Tetrahedron Lett. 35, 521-524.
27. Frey, M., Kliem, R., Saedler, H., and Gierl, A. (1995). Expression of a cytochrome P450 gene family in maize. Mol. Gen. Genet. 246, 100-109.
28. Frey, M., Chomet, P., Glawischnig, E., Stettner, C., Grün, S., Winklmair, A, Eisenreich, W., Bacher, A., Meeley, R. B., Briggs, S. P., Simcox, K., and Gierl, A. (1997). Analysis of a chemical plant defense mechanism in grasses. Science 277, 696-699.
29. Frey, M., Stettner, C., and Gierl, A. (1998). A general method for gene isolation in tagging approaches: Amplification of insertion mutagenised sites (AIMS). Plant J. 13, 717-722.
30. Freymark, P. J., Lee, M., Woodman, W. L., and Martinson, C. A. (1993). Quantitative and qualitative trait loci affecting host-plant response to Exserohilum turcicum in maize (Zea mays L.). Theor. Appl. Genet. 87, 537-544.
31. Friebe, A., Schulz, M., Kück, P., and Schnabl, H. (1995). Phytotoxins from shoot extracts of Agropyron repens seedlings. Phytochemistry 38, 1157-1159.
32. Friebe, A., Wieland, I., and Schulz, M. (1996). Tolerance of Avena sativa to the allelochemical benzoxazolinone. Degradation of BOA by root-colonizing bacteria. Angew. Bot. 70, 150-154.
33. +-ATPase. Phytochemistry 44, 979-983.
34. Gerber, N. N., and Lechevalier, M. P. (1964). Phenazines and phenoxazinones from Waksmania aerata sp. nov. and Pseudomonas iodina. Biochemistry 3, 598-602.
35. Gianoli, E., and Niemeyer, H. M. (1998). Allocation of herbivory-induced hydroxamic acids in the wild wheat Triticum uniaristatum. Chemoecology 8, 19-23.
36. Givovich A., and Niemeyer H. M. (1996). Role of hydroxamic acids in the resistance of wheat to the Russian Wheat Aphid diuraphis noxia (Mordvilko) (Hom., Ahidae). J. Appl. Ent. 120, 537-539.
37. 2. Phytochemistry 45, 715-718.
38. Glawischnig, E., Grün, S., Frey, M., and Gierl, A. (1999). Cytochrome P450 monooxygenases of DIBOA biosynthesis: Specificity and conservation among grasses. Phytochemistry 50, 925-930.
39. Grambow, H. J., Lückge, A., Klausener, E., and Müller, Z. (1986). Occurrence of 2-(2-Hydroxy-4,-7-dimethoxy-2H-1,4-benzoxazin-3-one)-b-D-glucopyranosi in Triticum aestivum leaves and ist conversion into 6-methoxybenzoxazolinone. Z. Naturforsch. 41c, 684-690.
40. Grombacher A. W., Russel, W. A., Guthrie, W. D. (1989). Resistance to first-generation European corn borer (Lepidoptera: Pyralidae) and DIMBOA concentration in midwhorl leaves of the BS9 maize synthetic. J. Kans Entom. Soc. 62, 103-107.
41. Gross, D. (1989). Antimicrobial defense compounds in the Gramineae. J. Plant Dis. Prot. 96, 535-553.
42. Hamilton R. H. (1964). A corn mutant deficient in 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one with an alteredtolerance of atrazine. Weeds 12, 27-30.
43. Harborne, J. B. (1977). "Introduction to Ecochemical Biochemistry." Academic Press, London.
44. Hartenstein, H., Lippmann, T., and Sicker, D. (1992). An efficient procedure for the isolation of pure 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) from maize. Ind. J. Heterocycl. Chem. 2, 75-76.
45. Hashimoto, Y., and Shudo, K. (1996). Chemistry of biologically active benzoxazinoids. Phytochemistry 43, 551-559.
46. Hashimoto, Y., Ishizaki, T., and Shudo, K. (1991). A multi-centered electrophile from a unique bioactive cyclic hydroxamic acid, 4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one. Tetrahedron 47, 1837-1860.
47. Hayashi, T., Goton, K., Ohnishi, K., Okamura, K., and Asamizu, T. (1994). 6-Methoxy-2-benzoxazolinone in Scoparia dulcis and its production by cultured tissues. Phytochemistry 37, 1611-1614.
48. Heath, M. C. (1985). Implications of nonhost resistance for understanding host parasite interactions. In "Genetic Basis of Biochemical Mechanisms of Plant Disease" (J. V. Groth, W. R. Bushnel, Eds.), American Phytopathological Society Press, St. Paul, MN. pp. 25-42.
49. Hedin, P. A., Davis, F. M., and Williams, W. P. (1993). 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one (N-O-ME-DIMBOA), a possible toxic factor in corn to the southwestern corn borer. J. Chem. Ecol. 19, 531-541.
50. Hietala, P. K., and Virtanen, A. I. (1960). Precursors of benzoxazolinone in rye plants. II. Precursor I, the glucoside. Acta Chem. Scand. 14, 502-504.
51. Hofman, J., and Masojidkova, M. (1973). 1,4-Benzoxazine glucosides from Zea mays. Phytochemistry 12, 207-208.
52. Hofmann, A., and Sicker, D. (1999). A formylating agent by dehydration of the natural product DIMBOA. J. Nat Prod. 62, 1151-1153.
53. Iida, K., Fukuda, S., Tanaka, T., Hirama, M., Imajo, S., Ishiguro, M, Yoshida, K., and Otani, T. (1996). Absolute Configuration of C-1027 Chromophore. Tetrahedron Lett. 37, 4997-5000.
54. Ishizaki, T., Hashimoto, Y., Shudo, K., and Okamoto, T. (1982). Reaction of 4-acetoxy-1,4-benzoxazin-3-one with DANN. A possible chemical mechanism for the antifungal and mutagenic activities. Tetrahedron Lett. 23, 4055-4056.
55. Iwamura, H., Nakagawa, E., and Hirai, N. (1996). Localization of benzoxazinones that occur constitutively in wheat seedlings. Z. Naturforschung. 51c, 807-812.
56. Kamperdick, C., Lien, T. P., Sung, T. V., and Adam, G. (1997). 2-Hydroxy-2H-1,4-benzoxazin-3-one from Scoparia dulcis. Pharmazie 52, 965-966.
57. Kato-Noguchi, H., Kosemura, S., and Yamamura, S. (1998). Allelopathic potential of 5-chloro-6-methoxy-2-benzoxazolinone. Phytochemistry 48, 433-435.
58. Klun, J. A., Guthrie, W. D., Hallauer, A. R., and Russel, W. A. (1970). 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 diallel set of eleven maize inbreds. Crop. Sci. 10, 87-90.
59. Kosemura, S., Emori, H., Yamamura, S., Anai, T., and Aizawa, H. (1995). Isolation and characterization of 4-chloro-6,7-dimethoxybenzoxazolin-2-one, a new auxin-inhibiting benzoxazolinone from Zea mays. Chem. Lett. 1053-1054.
60. Kramer, V. C., and Koziel, M. G. (1995). Structure of a maize tryptophan synthase alpha subunit gene with pith enhanced expression. Plant Mol. Biol. 27, 1183-1188.
61. 2BOA into aminophenoxazinones. J. Chem. Ecol. 19, 2453-2461.
62. Kutchan, T. M. (1995). Alkaloid biosynthesis - The basis for metabolic engineering of medicinal plants. Plant Cell 7, 1059-1070.
63. Leighton, V., Niemeyer, H. M., and Jonsson, L. M. V. (1994). Substrate specificity of a glucosyltransferase and an N-hydroxylase involved in the biosynthesis of cyclic hydroxamic acids in Graminea. Phytochemistry 36, 887-892.
64. Leszczynski, B., and Dixon, A. F. G. (1992). 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. Ent. 113, 61-67.
65. Massardo, F., Zuniga, G. E., Perez, L. M., and Corcuera, L. J. (1994). Effects of hydroxamic acids on electron transport and their cellular location in corn. Phytochemistry 35, 873-876.
66. Melanson, D., Chilton, M.-D., Masters-Moore, D., and Chilton, W. S. (1997). A deletion in an indole synthase gene is responsible for the DIMBOA-deficient phenotype of bxbx maize. Proc. Natl. Acad. Sci. 94, 13345.
67. Meyer, L. (1988). Role of cyclic hydroxamic acids in resistance of maize to microbial diseases and insects. Zentralbl. Mikrobiol. 143, 39-46.
68. Nagao, T., Otsuka, H., Kohda, H., Sato, T., and Yamasaki, K. (1985). Benzoxazinones from Coix lachryma jobi Var. Ma-Yuen. Phytochemistry 24, 2959-2962.
69. Nair, M. G., Whitenack, C. J., and Putnam, A. R. (1990). 2,2′-Oxo-1,1′-azobenzene: Amicrobially transformed allelochemical from 2,3-benzoxazoline. I. J. Chem. Ecol. 16, 353-364.
70. Niemeyer, H. M. (1988). Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones) defense chemicals in the Gramineae. Phytochemistry 27, 3349-3358.
71. Niemeyer, H. M., Pesel, E., Copaja, S. V., Bravo, H. R., Franke, A., and Francke, W. (1989). Changes in hydroxamic acid levels of wheat plants induced by aphid feeding. Phytochemistry 28, 447-449.
72. Niemeyer, H. M., Copaja, S. V., and Barria, B. N. (1992). The Triticeae as sources of hydroxamic acids, secondary metabolites in Wheat conferring resistance against aphids. Heredidas 116, 295-299.
73. Otani, T., Minami, Y., Marunaka, T., Zhang, R., and Xie, M.-Y. (1988). A new macromolecular antitumor antibiotic, C-1027: Isolation and physicochemical properties. J. Antibiot. 41, 1580-1585.
74. Özden, S., Özden, T., Attila, J., Kücükislamoglu, M., and Okatan, A. (1992). Isolation and identification via high performance liquid chromatography and thin layer chromatography of benzoxazolinone precursors from Consolida orientalis flowers. J. Chromatogr. 609, 402-406.
75. Perez, F. J., and Niemeyer, H. M. (1985). The reduction of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one by thiols. Phytochemistry 24, 2963-2966.
76. Perez, F. J., and Niemeyer, H. M. (1989a). Reaction of DIMBOA, a resistance factor from cereals, with papain. Phytochemistry 28, 1579-1600.
77. Perez, F. J., and Niemeyer, H. M. (1989b). Reaction of DIMBOA with amines. Phytochemistry 28, 1831-1834.
78. Perez, F. J., and Ormeno-Nunez, J. (1991). Differences in hydroxamic acid content in roots and root exudates of wheat (Triticum aestivum L.) and rye (Secale cereale L.). Possible role in allelopathy. J. Chem. Ecol. 17, 1037-1043.
79. Perez, F. J., and Ormeno-Nunez, J. (1993). Weed growth interference from temperate cereals. The effect of a hydroxamic acid exuding rye (Secale cereale L.) cultivar. Weed Res. 33, 115-119.
80. Pethö, M., Levai, L., and Römheld, V. (1997). The possible role of cyclic hydroxamic acids in the iron uptake of maize. Növenytermeles 46, 139-144.
81. Pratt, K., Kumar, P., and Chilton, W. S. (1995). Cyclic hydroxamic acids in dicotyledonous plants. Biochem. Syst. Ecol. 23, 781-785.
82. Putnam, A. R., and De Frank, J. (1983). Use of phytotoxic plant residues for selective weed control. J. Crop. Prot. 2, 173-181.
83. Queirolo, C. B., Andreo, C. S., Niemeyer, H. M., and Corcuera, L. J. (1983). Inhibition of ATPase from chloroplasts by a hydroxamic acid from the Gramineae. Phytochemistry 22, 2455-2458.
84. Radwanski, E. R., and Last, R. L. (1995). Tryptophan biosynthesis and metabolism: Biochemical and molecular genetics. Plant Cell 7, 921-934.
85. Radwanski, E. R., Zhao, J., and Last, R. L. (1995). Arabidopsis thaliana tryptophan synthase alpha: Gene cloning, expression, and subunit interaction. Mol. Gen. Genet. 248, 657-667.
86. Rice, E. L. (1984). "Allelopathy," 2nd ed., Academic Press, Orlando.
87. Rojas, G. M. C., Perez, F., and Gonzalez, L. (1997). Stimulatory effect of DIMBO A on NADH oxidation catalysed by horseradish peroxidase. Phytochemistry 46, 11-15.
88. Sahi, S. V., Chilton, M. D., and Chilton, W. S. (1990). Corn metabolites affect growth and virulence of Agrobacterium tumefaciens. Proc. Natl. Acad. Sci. USA 87, 3879-3883.
89. Schulz, M., Friebe, A., Kück, P., Seipel, M., and Schnabl, H. (1994). Allelopathic effects of living quackgrass (Agropyron repens L.). Identification of inhibitory allelochemicals exuded from rhizome borne roots. Angew. Bot. 68, 195-200.
90. Schulz, M., and Wieland, I. (1999). Variation in metabolism of BOA among species in various field communities - Biochemical evidence for co-evolutionary processes in plant communities? Chemoecology 9, 133-141.
91. Sicker, D., Hartenstein, H., and Kluge, M. (1997). Natural benzoxazinoids - Synthesis of acetal glucosides, aglucones, and analogues. In "Recent Research Developments in Phytochemistry" (S. G. Pandalai, Ed.), Vol. 1, pp. 203-223. Research Signpost, Trivandrum.
92. Tang, C. S., Chang, S. H., Hoo, D., and Yanagjhara, K. H. (1975). Gas chromatographic determination of 2(3)benzoxazolinones from cereal plants. Phytochemistry 14, 2077-2079.
93. Thackray, D. J., Wratten, S. D., Edwards, P. J., and Niemeyer, H. M. (1990). Resistance to the aphids Sitobion avena and Rhopalosiphum padi in Gramineae in relation to hydroxamic acid levels. Ann. Appl. Biol. 116, 573-582.
94. Tipton, C. L., Ming-Chung Wang, Tsao, F. H. C., Chang-Chu Lin Tu, and Husted, R. R., (1973). Biosynthesis of 1,4-benzoxazin-3-ones in Zea mays. Phytochemistry 12, 347-352.
95. Todorova, M., Werner, C., and Hesse, M. (1994). Enzymatic phenol oxidation and polymerization of the spermine alkaloid aphelandrine. Phytochemistry 37, 1251-1256.
96. Truan, G., Cullin, C., Reisdorf, P., Urban, P., and Pompon, D. (1993). Enhanced in vivo monooxygenase activities of mammalian P450s in engineered yeast cells producing high levels of NADPH-P450 reductase and human cytochrome b5. Gene 125, 49-55.
97. Tsuji, J., Zook, M., Hammerschmidt, R., Last, R. L., and Sommerville, S. C. (1993). Evidence that tryptophan is not a direct biosynthetic intermediate of camalexin in Arabidopsis thaliana. Physiol. Mol. Plant Pathol. 43, 221-229.
98. Turlings, T. C. J., Tumlinson, J. H., and Lewis, W. J. (1990). Exploitation of herbivore induced plant odors by host-seeking parasitic wasps. Science 250, 1251.
99. Urban, P., Werck-Reichhart, D., Teutsch, H. G., Durst, F., Regnier, S., Kazmaier, M., and Pompon, D. (1994). Characterization of recombinant plant cinnamate 4-hydroxylase produced in yeast. Kinetic and spectral properties of the major plant P450 of the phenylpropanoid pathway. Euro. J. Biochem. 222, 843-850.
100. Virtanen, A. I., and Hietala, P. K. (1955). 2(3)-Benzoxazolinone, an anti-Fusarium factor in rye seedlings. Acta Chem. Scand. 9, 1543-1545.
101. Virtanen, A. I., and Hietala, P. K. (1959). Suomen Kemistilehti B32, 252.
102. Virtanen, A. I., and Hietala, P. K. (1960). Precursors of Benzoxazolinone in Rye Plants. I. Precursor II, the Aglucone. Acta Chem. Scand. 14, 499-502.
103. Virtanen, A. I., Hietala, P. K., and Wahlroos, O. (1957). Arch. Biochem. 69, 486.
104. Wahlroos, Ö., and Virtanen, A. I. (1959). On the formation of 6-methoxybenzoxazolinone in maize and wheat plants. Suomen Kemistilehti 32B, 139-140.
105. Werner, C., Hedberg, C., Lorenzi-Riatsch, A., and Hesse, M. (1993). Accumulation and metabolism of the spermine alkaloid aphelandrine in roots of Aphelandra tetragona. Phytochemistry 33, 1033-1036.
106. Wieland, I., Kluge, M., Schneider, B., Schmidt, J., Sicker, D., and Schulz, M. (1998). 3-β-D-glucopyranosyl-benzoxazolin-2(3H)-one - A detoxification product of benzoxazolin-2(3H)-one in oat roots. Phytochemistry 49, 719-722.
107. Wieland, I., Friebe, A., Kluge, M., Sicker, D., and Schulz, M. (1999). Detoxification of benzoxazolinone in higher plants. "Recent Advances in Allelopathy. A Science for the Future," Vol. 1, pp. 79-88. Proceedings of the First World Congress on Allelopathy. Cadiz, Spain.
108. Wolf, R. B., Spencer, G. F., and Plattner, R. D. (1985). DIBOA-Glc in Acanthus mollis. J. Nat. Prod. 48, 59-62.
109. Woodward, M. D., Corcuera, L. J., Helgeson, J. P., and Upper, C. D. (1978). Decomposition of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in aqueous solutions. Plant. Physiol. 61, 796-802.
110. Woodward, M. D., Corcuera, L. J., Schnoes, H. K., Helgeson, J. P., and Upper, C. D. (1979). Identification of 1,4-Benzoxazin-3-ones in maize extracts by gas-liquid chromatography and mass spectrometry. Plant Physiol. 63, 9-13.
111. Wright, A. D., Moehlenkamp, C. A., Perrot, G. H., Neuffer, M. G., and Cone, K. C. (1992). The maize auxotrophic mutant orange pericarp is defective in duplicate genes for tryptophan synthase beta. Plant Cell 4, 711-719.
112. Yenish, J. P., Worsham, A. D., and Chilton, W. S. (1995). Disappearance of DIBOA-glucoside, DIBOA, and BOA from rye (Secale cereale L.) cover crop. Weed Techn. 11, 473-477.
113. Yu, L., Mah, S., Otani, T., and Dedon, P. (1995). The benzoxazolinate of C-1027 confers intercalative DNA binding. J. Am. Chem. Soc. 117, 8877-8878.
114. Zook, M. (1998). Biosynthesis of camalexin from tryptophan pathway intermediates in cell-suspension cultures of Arabidopsis. Plant Physiol. 118, 1389-1393.