CAS 5234-68-4|Carboxin|2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide|Vitavax|Carboxine|2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin|Kisvax|carboxin|2,3-Dihydro-6-methyl-5-phenylcarb...

General Information

Structure

Molecular Formula

C₁₂H₁₃NO₂S

Molecular Mass

235.30212

Exact Mass

235.06669966

Charge

InChI

InChI=1S/C12H13NO2S/c1-9-11(16-8-7-15-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14)

InChIKey

GYSSRZJIHXQEHQ-UHFFFAOYSA-N

Canonic Smiles

O=C(C1=C(C)OCCS1)Nc1ccccc1

Isomeric Smiles

CC1=C(SCCO1)C(=O)Nc1ccccc1

Calculated Properties

JChem

LogD (pH = 7.4)

1.51

LogD (pH = 5.5)

1.51

Log P

1.51

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

13.24

Polar Surface Area

38.33

Polarizability

24.84

Molar Refractivity

69.10

LOG S

-3.51

Data Source

Names and Identifiers

Synonyms

CarboxinCarboxine2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin2,3-Dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiinCarbathiinCarbathiineCBXVitavax 100CarboxineFenoxanVitavax2-Methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxaMideVitaflo 250Carboxin莠锈灵萎锈灵5-Carboxanilido-2,3-dihydro-6-methyl-1,4-oxathiinCarbathiin2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin5,6-Dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamideCarboxine2,3-Dihydro-6-methyl-1,4-oxathiin-5-carboxanilideoxatin5,6-Dihydro-2-methyl-3-carboxanilido-1,4-oxathiin5,6-Dihydro-2-methyl-1,4-oxathiin-3-carboxanilide2,3-Dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiincarboxin

IUPAC name

2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide

Brand Name

VitavaxKisvax

IUPAC Traditional name

carboxin 2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide

Names and Identifiers

Registration numbers

MDL Number

MFCD00055403

PubChem SID

2486884546507275160967649223439118

CAS Number

Beilstein Number

EC Number

PubChem CID

PubMed Citation Links

2304732021228470241190862326112424785712

Protein Data Bank

2wdq2wp92wu22wu52fbw2ws32wqy

LINCS Database

LSM-25660

BRENDA Ligand Database

CHEMBL

BKMS React Database

PPDB Database

PDBeChem Database

CompTox Database

CHEBI ID

MetaboLights Database

MTBLS1108MTBLS4967MTBLS2878MTBLS1622MTBLS379

BRENDA Database

ACToR Database

Pesticides Database

SureChEMBL Database

Reaxys Registry

KEGG ID

MetaCyc Database

Registration numbers

Properties

Product Information

Purity

95+%

98%

Empirical Formula (Hill Notation)

C12H13NO2S

Grade

PESTANAL®, analytical standard

Application(s)

Systemic agricultural fungicide

Physical Property

Flash Point

100 °C

212 °F

Pharmacology Properties

Mechanism of Action

Prevents the growth of yeast by inhibiting protein synthesis

The resumption of growth in the presence of this chemical appears to be primarily due to a cellular alteration affecting carboxin entry into the cells

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB04657

Drug Groups

experimental

Description

A systemic agricultural fungicide and seed treatment agent.

Sigma Aldrich

45371

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

ChEBI

CHEBI:3405

An anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid. A fungicide for control of bunts and smuts normally that is normally used as a seed treatment.

Molecule Details

References

PubChem Literature

From Data Sources

• U.S. Pat., 1965, 3 399 214; CA, 68, 78294x, (synth)

• White, G.A. et al., Pestic. Biochem. Physiol., 1978, 9, 165, (synth, activity)

• Lee, W.S. et al., J.O.C., 1986, 51, 27, (synth)

• Pesticide Manual, 9th edn., 1991, No. 2080

• Onuska, F.I. et al., Biomed. Mass Spectrom., 1976, 3, 248, (synth, ms)

• U.K. Pat., 1965, 1 099 242; CA, 65, 7190g

• Nevalainen, V. et al., Acta Chem. Scand., 1990, 44, 591, (synth)

• Caputo, R. et al., J.C.S. Perkin 1, 1995, 1971, (synth, pmr)

• Corbeil, M.A. et al., Can. J. Chem., 1973, 51, 2650, (synth, pmr)

• Larson, J.D. et al., J. Agric. Food Chem., 1984, 32, 177, (metab, ms)

• Dangerous Prop. Ind. Mater. Rep., 1990, 10, 47, (tox)

• Siskin, H.R. et al., J. Agric. Food Chem., 1971, 19, 738, (glc)

• McGlinchey, M.J. et al., J.C.S. Perkin 2, 1978, 1267, (pmr, cmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DLV200

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide

Brand Name

VitavaxKisvax

IUPAC Traditional name

carboxin 2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide

Registration numbers

MDL Number

MFCD00055403

PubChem SID

2486884546507275160967649223439118

CAS Number

Beilstein Number

EC Number

PubChem CID

PubMed Citation Links

2304732021228470241190862326112424785712

Protein Data Bank

2wdq2wp92wu22wu52fbw2ws32wqy

LINCS Database

LSM-25660

BRENDA Ligand Database

CHEMBL

BKMS React Database

PPDB Database

PDBeChem Database

CompTox Database

CHEBI ID

MetaboLights Database

MTBLS1108MTBLS4967MTBLS2878MTBLS1622MTBLS379

BRENDA Database

ACToR Database

Pesticides Database

SureChEMBL Database

Reaxys Registry

KEGG ID

MetaCyc Database

Properties

Product Information

Purity

95+%

98%

Empirical Formula (Hill Notation)

C12H13NO2S

Grade

PESTANAL®, analytical standard

Application(s)

Systemic agricultural fungicide

Physical Property

Flash Point

100 °C

212 °F

Pharmacology Properties

Mechanism of Action

Prevents the growth of yeast by inhibiting protein synthesis

The resumption of growth in the presence of this chemical appears to be primarily due to a cellular alteration affecting carboxin entry into the cells