DIMBOA

DIMBOA

Names
IUPAC name 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one
Identifiers
CAS Number	15893-52-4
ChemSpider	2268
Jmol interactive 3D	Image
PubChem	2358
InChI InChI=1S/C9H9NO5/c1-14-5-2-3-6-7(4-5)15-9(12)8(11)10(6)13/h2-4,9,12-13H,1H3 Key: GDNZNIJPBQATCZ-UHFFFAOYSA-N InChI=1/C9H9NO5/c1-14-5-2-3-6-7(4-5)15-9(12)8(11)10(6)13/h2-4,9,12-13H,1H3 Key: GDNZNIJPBQATCZ-UHFFFAOYAE
SMILES ON(C1=CC=C(OC)C=C1OC2O)C2=O
Properties
Chemical formula	C9H9NO5
Molar mass	211.17 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

DIMBOA (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one) is a naturally-occurring hydroxamic acid, a benzoxazinoid. DIMBOA is a powerful antibiotic present in maize and related grasses, particularly wheat.

In maize, DIMBOA functions as natural defense against European corn borer larvae and many other damaging pests, including fungi and bacteria.^[1] The exact level of DIMBOA varies between individual plants, but higher concentrations are typically found in young seedlings and the concentration decreases as the plant ages.^[2]

References

1. G7113 European Corn Borer: A Multiple-Crop Pest in Missouri, MU Extension
2. Cambier, V; Hance, T; de Hoffmann, E (2000). "Variation of DIMBOA and related compounds content in relation to the age and plant organ in maize". Phytochemistry 53 (2): 223–229. doi:10.1016/S0031-9422(99)00498-7. PMID 10680175.