SynCED: Thiophanate-methyl

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:55 UTC

Update Date

2026-08-18 17:50:07 UTC

Accession Number

CHEM002895

Identification

Common Name

Thiophanate-methyl

Class

Small Molecule

Description

Thiophanate-Methyl (TM) is a systemic fungicide. It was first registered to be used as a fungicide by the EPA in 1973. It is effective against a wide range of fungal pathogens including: eyespot and other diseases of cereals; scab on apples and pears; Monilia disease and Gloeosporim rot on apples; Monilia app. On stone fruit; Canker on fruit trees; powdery mildews on pome fruit, stone fruit, vegetables, cucurbits, strawberries, vines, roses. Thiophanate methyl is also used on almonds, pecans, tea, coffee, peanuts, soya beans, tobacco, chestnuts, sugar cane, citrus fruit, figs, hops, mulberries, and many other crops.

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Ether
Fungicide
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Bis(3-(methoxycarbonyl)-2-thioureido)benzene	ChEBI
1,2-Bis(methoxycarbonylthioureido)benzene	ChEBI
1,2-Di-(3-methoxycarbonyl-2-thioureido)benzene	ChEBI
Dimethyl 4,4'-(O-phenylene)bis(3-thioallophanate)	ChEBI
Dimethyl N,n'-[1,2-phenylenebis(azanediylcarbonothioyl)]dicarbamate	ChEBI
Dimethyl N,n'-[1,2-phenylenebis(iminocarbonothioyl)]bis[carbamate]	ChEBI
Methyl thiophanate	ChEBI
Methylthiofanate	ChEBI
Methylthiophanate	ChEBI
O-Bis(3-methoxycarbonyl-2-thioureido)benzene	ChEBI
Dimethyl 4,4'-(O-phenylene)bis(3-thioallophanic acid)	Generator
Dimethyl N,n'-[1,2-phenylenebis(azanediylcarbonothioyl)]dicarbamic acid	Generator
Dimethyl N,n'-[1,2-phenylenebis(iminocarbonothioyl)]bis[carbamic acid]	Generator
Methyl thiophanic acid	Generator
Methylthiofanic acid	Generator
Methylthiophanic acid	Generator
Thiophanic acid-methyl	Generator
Cercobin m 70	MeSH
Dimethylphenylene bis-thioallophanate	MeSH
Thiophanate	MeSH
Dimethylphenylene bis thioallophanate	MeSH
Mildothane	MeSH
Bis-thioallophanate, dimethylphenylene	MeSH
Cercobin m-70	MeSH
Thiophanate methyl	MeSH
Cercobin m70	MeSH

Chemical Formula

C₁₂H₁₄N₄O₄S₂

Average Molecular Mass

342.394 g/mol

Monoisotopic Mass

342.046 g/mol

CAS Registry Number

23564-05-8

IUPAC Name

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

Traditional Name

zyban

SMILES

COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC

InChI Identifier

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)

InChI Key

QGHREAKMXXNCOA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Imine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:35014 )
thioureas (CHEBI:35014 )
benzimidazole precursor fungicide (CHEBI:35014 )
carbamate fungicide (CHEBI:35014 )
Carbamate fungicides (C14432 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0058 g/L	ALOGPS
logP	1.57	ALOGPS
logP	2.78	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	100.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.5 m³·mol⁻¹	ChemAxon
Polarizability	33.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Thiophanate-methyl is likely a human carcinogen. It increases of risk of liver tumours in mice. Thyroid/parathyroid weights were increased The developmental toxicity studies showed the decreased fetal body weight and increases in skeletal variations in the fetuses of rabbits exposed to thiophanate-methyl. It induced histopathological damages in rat thyroid and adrenal glands.

Symptoms

Thiophanate-methyl can cause skin, eye and respiratory irritation, shortness of breath, chest pains, burning eyes, dizziness, and fatigue.

Treatment

Rinse dermal exposure with water, irrigate exposed eyes with water, remove the contaminated clothing. Intubate the patients with altered mental status or airway injury. Treat acidosis and seizures. Patients should be treated with activated charcoal after large ingestions of thiophanate-methyl if they can drink the charcoal.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0259025

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID