2H-1,4-benzoxazin-3(4H)-one
2H-1,4-benzoxazin-3-one
Identification
| Name | 2H-1,4-benzoxazin-3(4H)-one |
| CAS Number | 5466-88-6 |
| FDA UNII | Q0QAF5G662 |
| Molecular Formula | C8 H7 N O2 |
| Molecular Weight | 149.14919000 |
| MDL Number | MFCD00158536 |
| Nikkaji Number | J81.041J |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 400 mg/L @ 20 °C (exp) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for 2H-1,4-benzoxazin-3(4H)-one usage levels up to | not for fragrance use. |
| Recommendation for 2H-1,4-benzoxazin-3(4H)-one flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4.3-oxo-4H-
benzo[1,4]oxazine
2H-1,4-
benzoxazin-3-one
4H-1,4-
benzoxazin-3-one
PubMed:
Using gene expression database to uncover biology functions of 1,4-disubstituted 1,2,3-triazole analogues synthesized via a copper (I)-catalyzed reaction.
PubMed:
Melanogenesis inhibitors from Coix lacryma-jobi seeds in B16-F10 melanoma cells.
PubMed:
Plant defense and herbivore counter-defense: benzoxazinoids and insect herbivores.
PubMed:
Benzoxazinone-Mediated Triazine Degradation: A Proposed Reaction Mechanism.
PubMed:
A New Neolignan from Coix lachryma-jobi var. mayuen.
PubMed:
Synthesis and antifungal activity of 2H-1,4-benzoxazin-3(4H)-one derivatives.
PubMed:
2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) inhibits trichothecene production by Fusarium graminearum through suppression of Tri6 expression.
PubMed:
In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one].
PubMed:
Plant-plant-microbe mechanisms involved in soil-borne disease suppression on a maize and pepper intercropping system.
PubMed:
Discovery of 6-[5-(4-fluorophenyl)-3-methyl-pyrazol-4-yl]-benzoxazin-3-one derivatives as novel selective nonsteroidal mineralocorticoid receptor antagonists.
PubMed:
A new phenolic component from Triticum aestivum sprouts and its effects on LPS-stimulated production of nitric oxide and TNF-α in RAW 264.7 cells.
PubMed:
In silico characterization of three two-component systems of Ehrlichia canis and evaluation of a natural plant-derived inhibitor.
PubMed:
Benzoxazinoids from Scoparia dulcis (sweet broomweed) with antiproliferative activity against the DU-145 human prostate cancer cell line.
PubMed:
Benzoxazinoids in root exudates of maize attract Pseudomonas putida to the rhizosphere.
PubMed:
Study of the role played by NfsA, NfsB nitroreductase and NemA flavin reductase from Escherichia coli in the conversion of ethyl 2-(2'-nitrophenoxy)acetate to 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIBOA), a benzohydroxamic acid with interesting biological properties.
PubMed:
Identification of benzoxazin-3-one derivatives as novel, potent, and selective nonsteroidal mineralocorticoid receptor antagonists.
PubMed:
Is the basal area of maize internodes involved in borer resistance?
PubMed:
Benzoxazinoid metabolites regulate innate immunity against aphids and fungi in maize.
PubMed:
Acanmontanoside, a new phenylethanoid diglycoside from Acanthus montanus.
PubMed:
Structure-activity relationship of benzoxazinones and related compounds with respect to the growth inhibition and alpha-amylase activity in cress seedlings.
PubMed:
A novel glycoside from Acanthus hirsutus (Acanthaceae).
PubMed:
Pharmacological characterization of olodaterol, a novel inhaled beta2-adrenoceptor agonist exerting a 24-hour-long duration of action in preclinical models.
PubMed:
Fluconazole analogues containing 2H-1,4-benzothiazin-3(4H)-one or 2H-1,4-benzoxazin-3(4H)-one moieties, a novel class of anti-Candida agents.
PubMed:
Rediscovering the bioactivity and ecological role of 1,4-benzoxazinones.
PubMed:
Aromatic-ring-functionalised benzoxazinones in the system Oryza sativa-Echinochloa crus-galli as biorational herbicide models.
PubMed:
Species-specific glucosylation of DIMBOA in larvae of the rice Armyworm.
PubMed:
Hydroxamic acids derived from 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one: key defense chemicals of cereals.
PubMed:
8-Chloro-4-cyclo-hexyl-2H-1,4-benzoxazin-3(4H)-one.
PubMed:
7-Chloro-4-phenethyl-2H-1,4-benzoxazin-3(4H)-one.
PubMed:
Activity of Hydroxamic Acids from Secale cereale Against the Plant-Parasitic Nematodes Meloidogyne incognita and Xiphinema americanum.
PubMed:
Benzoxazinoid biosynthesis in dicot plants.
PubMed:
Modified benzoxazinones in the system Oryza sativa-Echinochloa crus-galli: an approach to the development of biorational herbicide models.
PubMed:
Novel 5-HT(1A/1B/1D) receptors antagonists with potent 5-HT reuptake inhibitory activity.
PubMed:
Preparative isolation and purification of two benzoxazinoid glucosides from Acanthus ilicifolius L. by high-speed counter-current chromatography.
PubMed:
Effects of four benzoxazinoids on gibberellin-induced alpha-amylase activity in barley seeds.
PubMed:
Elucidation of the final reactions of DIMBOA-glucoside biosynthesis in maize: characterization of Bx6 and Bx7.
PubMed:
6-Chloro-2H-1,4-benzoxazin-3(4H)-one.
PubMed:
Synthesis of novel 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones as anticonvulsant agents.
PubMed:
cis-Jasmone induces accumulation of defence compounds in wheat, Triticum aestivum.
PubMed:
Characterization of the potent 5-HT(1A/B) receptor antagonist and serotonin reuptake inhibitor SB-649915: preclinical evidence for hastened onset of antidepressant/anxiolytic efficacy.
PubMed:
Simultaneous blockade of 5-HT1A/B receptors and 5-HT transporters results in acute increases in extracellular 5-HT in both rats and guinea pigs: in vivo characterization of the novel 5-HT1A/B receptor antagonist/5-HT transport inhibitor SB-649915-B.
PubMed:
New herbicide models from benzoxazinones: aromatic ring functionalization effects.
PubMed:
Optimization of benzoxazinones as natural herbicide models by lipophilicity enhancement.
PubMed:
SB-649915, a novel, potent 5-HT1A and 5-HT1B autoreceptor antagonist and 5-HT re-uptake inhibitor in native tissue.
PubMed:
Structure-activity relationship (SAR) studies of benzoxazinones, their degradation products, and analogues. Phytotoxicity on problematic weeds Avena fatua L. and Lolium rigidum Gaud.
PubMed:
Isolation and synthesis of allelochemicals from gramineae: benzoxazinones and related compounds.
PubMed:
Effects of the benzoxazoid DIMBOA, selected degradation products, and structure-related pesticides on soil organisms.
PubMed:
Hydroxamic acid content and toxicity of rye at selected growth stages.
PubMed:
On the structural basis of the catalytic mechanism and the regulation of the alpha subunit of tryptophan synthase from Salmonella typhimurium and BX1 from maize, two evolutionarily related enzymes.
PubMed:
The possible role of hydroxylation in the detoxification of atrazine in mature vetiver (Chrysopogon zizanioides Nash) grown in hydroponics.
PubMed:
Structure-activity relationship studies of benzoxazinones and related compounds. Phytotoxicity on Echinochloa crus-galli (L.) P. Beauv.
PubMed:
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.
PubMed:
Enantioseparation of 2-O-beta-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one and its 7-chloro-derivative by capillary zone electrophoresis using native and substituted beta-cyclodextrins as chiral additives.
PubMed:
Detoxification and transcriptome response in Arabidopsis seedlings exposed to the allelochemical benzoxazolin-2(3H)-one.
PubMed:
Degradation studies on benzoxazinoids. Soil degradation dynamics of (2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-(2H)- 1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and its degradation products, phytotoxic allelochemicals from Gramineae.
PubMed:
Structure-Activity Relationships (SAR) studies of benzoxazinones, their degradation products and analogues. phytotoxicity on standard target species (STS).
PubMed:
Chemical composition of corn leaf essential oils and their role in the oviposition behavior of Sesamia nonagrioides females.
PubMed:
Differential exudation of two benzoxazinoids--one of the determining factors for seedling allelopathy of Triticeae species.
PubMed:
Development of a liquid chromatography-electrospray mass spectrometric method for the simultaneous analysis of benzoxazolinones and their degradation products.
PubMed:
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.
PubMed:
Benzoxazinoids and iridoid glucosides from four Lamium species.
PubMed:
Utilisation of electrospray time-of-flight mass spectrometry for solving complex fragmentation patterns: application to benzoxazinone derivatives.
PubMed:
Antitumor agents. Part 218: Cappamensin A, a new In vitro anticancer principle, from Capparis sikkimensis.
PubMed:
A mechanistic dehydration study with [2-(13)C]-DIMBOA.
PubMed:
Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus.
PubMed:
Benzoxazinoid glucosides from Acanthus ilicifolius.
PubMed:
Simple method for large scale isolation of the cyclic arylhydroxamic acid DIMBOA from maize (Zea mays L.).
PubMed:
Metabolism of 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4- (2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (S-53482, flumioxazin) in the rat: II. Identification of reduced metabolites.
PubMed:
Metabolism of 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4- (2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (S-53482) in rat. 1. Identification of a sulfonic acid type conjugate.
PubMed:
Chemistry of biologically active benzoxazinoids.
PubMed:
[Chemistry of benzoxazinoids produced by plants as phytoalexin].
PubMed:
Isolation and characterization of a cyclic hydroxamic acid from a pollen extract, which inhibits cancerous cell growth in vitro.
PubMed:
Corn metabolites affect growth and virulence of Agrobacterium tumefaciens.
PubMed:
Hydroxamic Acid glucosyltransferases from maize seedlings.
PubMed:
Lipid lowering actions of 7-(2-methylene butyryl)-(2H)-1,4-benzoxazin-3-(4H)-one derivatives in mice, rats and Syrian hamsters.
PubMed:
Identification of 1,4-Benzoxazin-3-ones in Maize Extracts by Gas-Liquid Chromatography and Mass Spectrometry.
PubMed:
Factors That Influence the Activity of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one on Erwinia Species in Growth Assays.
PubMed:
Decomposition of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in Aqueous Solutions.
PubMed:
2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, an Inhibitor from Zea mays with Differential Activity against Soft Rotting Erwinia Species.