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

• ChemBase ID: 4217
• Molecular Formular: C12H13NO2S
• Molecular Mass: 235.30212
• Monoisotopic Mass: 235.06669966
• SMILES: CC1=C(SCCO1)C(=O)Nc1ccccc1
• Canonical SMILES: O=C(C1=C(C)OCCS1)Nc1ccccc1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
• IUPAC Traditional name: carboxin; 2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
• Brand Name: Vitavax; Kisvax
• Synonyms: Carbathiin; Carboxine; Carbathiine; 2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin; 2,3-Dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiin; CBX; Carboxin; Carboxine; Vitavax; Vitaflo 250; Vitavax 100; Fenoxan; Carboxin; 2-Methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxaMide; 莠锈灵; 萎锈灵

Database IDs

• CAS Number: 5234-68-4
• EC Number: 226-031-1
• MDL Number: MFCD00055403
• Beilstein Number: 983249
• PubChem SID: 160967649; 24868845; 46507275
• PubChem CID: 21307

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.243225
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.512659
• LogD (pH = 7.4): 1.5126584
• Log P: 1.512659
• Molar Refractivity: 69.0963 cm^3
• Polarizability: 25.383682 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.65
• LOG S: -2.64
• Solubility (Water): 5.36e-01 g/l

PROPERTIES

Physical Property

• Flash Point: 100 °C; 212 °F

Safety Information

• Storage Warning: IRRITANT
• RTECS: RP4550000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 21/22
• Safety Statements: 36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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

Product Information

• Purity: 95+%; 98%
• Grade: PESTANAL®, analytical standard
• Application(s): Systemic agricultural fungicide
• Empirical Formula (Hill Notation): C12H13NO2S

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

REFERENCES

• U.K. Pat., 1965, 1 099 242; CA, 65, 7190g
• U.S. Pat., 1965, 3 399 214; CA, 68, 78294x, (synth)
• Siskin, H.R. et al., J. Agric. Food Chem., 1971, 19, 738, (glc)
• Corbeil, M.A. et al., Can. J. Chem., 1973, 51, 2650, (synth, pmr)
• Onuska, F.I. et al., Biomed. Mass Spectrom., 1976, 3, 248, (synth, ms)
• McGlinchey, M.J. et al., J.C.S. Perkin 2, 1978, 1267, (pmr, cmr)
• White, G.A. et al., Pestic. Biochem. Physiol., 1978, 9, 165, (synth, activity)
• Larson, J.D. et al., J. Agric. Food Chem., 1984, 32, 177, (metab, ms)
• Lee, W.S. et al., J.O.C., 1986, 51, 27, (synth)
• Nevalainen, V. et al., Acta Chem. Scand., 1990, 44, 591, (synth)
• Dangerous Prop. Ind. Mater. Rep., 1990, 10, 47, (tox)
• Pesticide Manual, 9th edn., 1991, No. 2080
• Caputo, R. et al., J.C.S. Perkin 1, 1995, 1971, (synth, pmr)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DLV200