methyl N-{[2-({[(methoxycarbonyl)amino]methanethioyl}amino)phenyl]carbamothioyl}carbamate

• ChemBase ID: 158098
• Molecular Formular: C12H14N4O4S2
• Molecular Mass: 342.39396
• Monoisotopic Mass: 342.04564695
• SMILES: COC(=O)NC(=S)Nc1ccccc1NC(=S)NC(=O)OC
• Canonical SMILES: COC(=O)NC(=S)Nc1ccccc1NC(=S)NC(=O)OC
• InChI: InChI=1S/C12H14N4O4S2/c1-19-11(17)15-9(21)13-7-5-3-4-6-8(7)14-10(22)16-12(18)20-2/h3-6H,1-2H3,(H2,13,15,17,21)(H2,14,16,18,22)
• InChIKey: QGHREAKMXXNCOA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-{[2-({[(methoxycarbonyl)amino]methanethioyl}amino)phenyl]carbamothioyl}carbamate
• IUPAC Traditional name: zyban
• Synonyms: N,N'-[1,2-Phenylenebis(iminocarbonothioyl)]biscarbamic Acid C,C'-Dimethyl Ester; 4,4'-o-Phenylenebis[3-thioallophanic Acid Dimethyl Ester; 1,2-Bis[3-(methoxycarbonyl)-2-thioureido]benzene; 3336G; Caligran; Cercobin M 70; Cercobin Methyl; Cycosin; Dimethyl 4,4'-o-Phenylenebis(3-thioallophanate); Easout; Enovit M 70; Enovit Super; Enovit-methyl; F 6385; Fungo; Methyl topsin; Methylthiofanate; Methylthiophanate; Metoben; Mildothane; NF 44; NSC 170811; Neotopsin; Thiopan; Thiophanate methyl; Tops; Topsin 500SC; Topsin M 70WP; Topsin MD; Topsin Methyl; o-Bis(3-methoxycarbonyl-2-thioureido)benzene; Thiophanate-Methyl; Thiophanate-methyl; 甲基硫菌灵

Database IDs

• CAS Number: 23564-05-8
• EC Number: 245-740-7
• MDL Number: MFCD00055294
• Beilstein Number: 937942
• PubChem SID: 162252234; 24869253; 24899171
• PubChem CID: 3032791

CALCULATED PROPERTIES

• Acid pKa: 6.7826457
• H Acceptors: 2
• H Donor: 4
• LogD (pH = 5.5): 2.7560196
• LogD (pH = 7.4): 2.0754094
• Log P: 2.7771134
• Molar Refractivity: 91.4982 cm^3
• Polarizability: 34.36215 Å^3
• Polar Surface Area: 100.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 165-167°C (dec.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: BA3675000
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 20-43-50/53-68
• Safety Statements: 36/37-46-60-61
• GHS Pictograms: GHS07; GHS08; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H332-H341-H410
• GHS Precautionary statements: P273-P280-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Grade: analytical standard; PESTANAL®, analytical standard
• Packaging: ampule of 1000 mg
• Empirical Formula (Hill Notation): C12H14N4O4S2

DETAILS

Sigma Aldrich - 45688

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

Toronto Research Chemicals - T344810

Thiophanate-Methyl is a systematic fungicide of the thiophanate class. Thiophanate-Methyl is commonly used in agriculture to protect against powdery mildew, rot and other fungal diseases in fruits, vegetables and other crops.

REFERENCES

• Vonk, J.W. et al.: Pest. Sci., 2, 160 (1971)
• Burchill, R.T. et al.: Plant Pathol., 20, 173 (1971)
• Fuchs, A. et al.: Pest. Biochem. Physiol., 2, 191 (1971)
• Frossard, P. et al.: Fruits, 28, 195 (1971)