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543551

Sigma-Aldrich

6-Methoxy-2-benzoxazolinone

97%

Synonym(s):

6-MBOA, 6-Methoxy-2(3H)-benzoxazolone, 6-Methoxy-3H-benzoxazol-2-one, 6-Methoxybenzo[d]oxazol-2(3H)-one, 6-Methoxybenzoxazolin-2(3H)-one, 6-Methoxybenzoxazolinone

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About This Item

Empirical Formula (Hill Notation):
C8H7NO3
CAS Number:
532-91-2
Molecular Weight:
165.15
MDL number:
MFCD00051726
UNSPSC Code:
12352100
PubChem Substance ID:
24878693
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

151-156 °C (lit.)

SMILES string

COc1ccc2NC(=O)Oc2c1

InChI

1S/C8H7NO3/c1-11-5-2-3-6-7(4-5)12-8(10)9-6/h2-4H,1H3,(H,9,10)

InChI key

MKMCJLMBVKHUMS-UHFFFAOYSA-N

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General description

6-Methoxy-2-benzoxazolinone (MBOA) is obtained by reacting 2-amino-5-methoxyphenol hydrochloride with urea. MOBA is a naturally occurring auxin-inhibiting substance present in maize shoots.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000238170
0000269342
0000177591
MKCS0800
MKCQ0913

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J Acharya et al.
Plant disease, 105(4), 752-757 (2020-10-14)
Corn yield reduction following a cereal rye cover crop has been attributed to, among other factors, allelochemicals released from decomposing cereal rye residue. The allelopathic effect of 6-methoxy-2-benzoxazolinone (MBOA) was evaluated on corn seedling growth, mycelial growth of seven pathogenic
On the Synthesis of 6-Methoxy-2-benzoxazolinone.
John DR, et al.
Agricultural and Biological Chemistry, 39(3), 683-685 (1975)
Chunhong Jia et al.
Journal of agricultural and food chemistry, 54(4), 1049-1057 (2006-02-16)
The joint action of binary and ternary mixtures of benzoxazinone derivatives and phenolic acids was studied using the additive dose model (ADM) as reference model. The activity of fixed-ratio mixtures of phenolic acids [ferulic acid (FA), p-coumaric acid (CA), vanillic
Thomas Etzerodt et al.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes, 43(1), 1-7 (2007-12-29)
Wheat (Triticum aestivum L.) and other cereals produce allelochemicals as natural defense compounds against weeds, fungi, insects and soil-borne diseases. The main benzoxazinoid allelochemical of wheat is 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), bound as beta-glucoside and released upon plant injury. When leached from
Elena Lo Piparo et al.
Journal of agricultural and food chemistry, 54(4), 1111-1115 (2006-02-16)
The overall objective of this study is the ecotoxicological characterization of the benzoxazinone 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), the benzoxazolinones benzoxazolin-2-one (BOA) and 6-methoxybenzoxazolin-2-one (MBOA), and their transformation products: phenoxazinones 2-acetylamino-7-methoxy-3H-phenoxazin-3-one (AAMPO), 2-acetylamino-3H-phenoxazin-3-one (AAPO), 2-amino-7-methoxy-3H-phenoxazin-3-one (AMPO), and 2-amino-3H-phenoxazin-3-one (APO); aminophenol 2-aminophenol AP); acetamide
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