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Details

Stereochemistry ACHIRAL
Molecular Formula C12H14N4O4S2
Molecular Weight 342.394
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIOPHANATE-METHYL

SMILES

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

InChI

InChIKey=QGHREAKMXXNCOA-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C12H14N4O4S2
Molecular Weight 342.394
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Thiophanate methyl is an approved EU fungicide used widely to control fungal diseases on crops. It has a low aqueous solubility, low volatility and tends not to be persistent in soil or water systems. It has a low mammalian toxicity, however it is an irritant, a skin sensitiser and may also be mutagen. It is moderately toxic to most aquatic organisms and earthworms but less so to birds and honeybees.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
A case of bupropion-induced Stevens-Johnson syndrome with acute psoriatic exacerbation.
2010-08
The use of snus for quitting smoking compared with medicinal products.
2010-08
Disparities of care for African-Americans and Caucasians with community-acquired pneumonia: a retrospective cohort study.
2010-05-27
Synthesis and biological activity of some novel trifluoromethyl-substituted 1,2,4-triazole and bis(1,2,4-triazole) Mannich bases containing piperazine rings.
2010-05-12
[Pathogen identification of Pinellia ternata tuber disease and selection of fungicide].
2010-04
Design, recruitment, and retention of African-American smokers in a pharmacokinetic study.
2010-01-19
Smoking status and cessation counseling practices among physicians, Guangxi, China, 2007.
2010-01
Effect of Medicaid coverage of tobacco-dependence treatments on smoking cessation.
2009-12
Pesticide extraction from table grapes and plums using ionic liquid based dispersive liquid-liquid microextraction.
2009-12
Description of Cryptosporiopsis kienholzii and species profiles of Neofabraea in major pome fruit growing districts in the Pacific Northwest USA.
2009-11
Ionic liquid based dispersive liquid-liquid microextraction for the extraction of pesticides from bananas.
2009-10-23
Promoting smoking cessation in Bangladeshi and Pakistani male adults: design of a pilot cluster randomised controlled trial of trained community smoking cessation workers.
2009-08-14
Determination of multi-class pesticides in wines by solid-phase extraction and liquid chromatography-tandem mass spectrometry.
2009-07-31
Use of non-assigned smoking cessation programs among participants of a Web-based randomized controlled trial.
2009-06-25
In vitro toxicity of selected fungicides from the groups of benzimidazoles and demethylation inhibitors to Cladobotryum dendroides and Agaricus bisporus.
2009-05
Beneficial impacts of a national smokefree environments law on an indigenous population: a multifaceted evaluation.
2009-04-30
In vitro study on the interaction between thiophanate methyl and human serum albumin.
2009-03-03
Internally-developed teen smoking cessation programs: characterizing the unique features of programs developed by community-based organizations.
2009-03
An algorithm for tailoring pharmacotherapy for smoking cessation: results from a Delphi panel of international experts.
2009-02
Do implementation issues influence the effectiveness of medications? The case of nicotine replacement therapy and bupropion in UK Stop Smoking Services.
2009-01-21
[Psychiatry].
2009-01-14
Rapid development of fungicide resistance by Sclerotinia homoeocarpa on turfgrass.
2008-12
Comparing two web-based smoking cessation programs: randomized controlled trial.
2008-11-18
Trends in employer-sponsored health insurance coverage for tobacco-dependence treatments.
2008-10
Morphological and functional changes in the thyroid gland of methyl thiophanate-injected lizards, Podarcis sicula.
2008-08
Effectiveness of computer-tailored Smoking Cessation Advice in Primary Care (ESCAPE): a randomised trial.
2008-04-29
Clinician perceptions of factors influencing referrals to a smoking cessation program.
2008-03-28
Reliability of internet- versus telephone-administered questionnaires in a diverse sample of smokers.
2008-03-26
A fatal case of bupropion (Zyban) overdose.
2008-03
Molecular characterization of benzimidazole-resistant isolates of Cladosporium fulvum.
2008-01
Modification and re-validation of the ethyl acetate-based multi-residue method for pesticides in produce.
2007-11
Impact of a statewide Internet-based tobacco cessation intervention.
2007-09-30
The effects of the fungicide methyl thiophanate on adrenal gland morphophysiology of the lizard, Podarcis sicula.
2007-08
Generic drug policy in Australia: a community pharmacy perspective.
2007-06-01
A randomised controlled trial of a smoking cessation intervention delivered by dental hygienists: a feasibility study.
2007-05-02
Bupropion hydrochloride produces conditioned hyperactivity in rats.
2007-04-23
PPARalpha mediates the effects of the pesticide methyl thiophanate on liver of the lizard Podarcis sicula.
2007-04
[Susceptibility of Trichogramma pretiosum Riley (Hymenoptera: Trichogrammatidae) adults to fungicides used to control apple diseases].
2007-03-14
Impact of the stem borer, Dectes texanus, on yield of the cultivated sunflower, Helianthus annuus.
2007
[Study on usage of pesticides in various countries].
2007
General practitioners' beliefs about effectiveness and intentions to prescribe smoking cessation medications: qualitative and quantitative studies.
2006-11-08
Barriers and motivators to gaining access to smoking cessation services amongst deprived smokers--a qualitative study.
2006-11-06
Knowledge of Medicaid coverage and effectiveness of smoking treatments.
2006-11
A rationale and model for addressing tobacco dependence in substance abuse treatment.
2006-08-14
The costs and effectiveness of different benefit designs for treating tobacco dependence: results from a randomized trial.
2006
Effects of exposure of youths at risk for smoking to television advertising for nicotine replacement therapy and Zyban: an experimental study.
2006
Combinations of Fungicides with Phylloplane Yeasts for Improved Control of Botrytis cinerea on Geranium Seedlings.
2004-02
Pharmacological treatment for pregnant women who smoke cigarettes.
2003-09-15
Targeting nicotine addiction in a substance abuse program.
2003-08
Phenotype Instability in Botrytis cinerea in the Absence of Benzimidazole and Dicarboximide Fungicides.
2001-03
Patents

Patents

JP2001072507A
1
JP2001072512A
1
JP2004018374A
2
JP2005527597A
6
JP2007246495A
1
JP2007332058A
3
JP2007509088A
21
JP2007521231A
2
JP2008509189A
189
JP2009013122A
1
JP2010024175A
1
JP2010159277A
5
JP2011225497A
1
JP2011509959A
61
JP2012006886A
6
JP2012500824A
79
JP4677101B2
3
JP4681565B2
5
JP4711974B2
3
JP4722398B2
5
JP59106406A
1
JPH01190608A
1
JPH02174706A
1
JPH04261106A
1
JPH05148109A
2
JPH0558819A
1
JPH06239708A
1
JPH06298615A
1
JPS05916808A
1
JPS06368506A
1
JPS0638306A
1
JPS54105230A
2
JPS54126730A
1
JPS55124705A
1
JPS5576806A
1
JPS56167606A
1
JPS5677206A
1
JPS5681506A
1
JPS57128605A
1
JPS5726604A
1
JPS5762208A
1
JPS58134007A
1
JPS58192806A
1
JPS5832804A
1
JPS5890505A
1
JPS59106406A
2
JPS5916808A
5
JPS60218366A
1
JPS60218367A
1
JPS6028902A
4
JPS6038306A
1

Sample Use Guides

In Vivo Use Guide
Following the oral administration of 700 and 1000 mg kg(-1) body wt. for five consecutive days, short-term testicular toxicity was examined in the B6C3F1 mouse through specific parameters (sperm head count, specific enzyme activities, histopathology on days 3-35 post-dosing).
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: In the absence of metabolic activation, Thiophanate methyl exerted cytotoxic activity in BALB/c 3T3 cells, evidenced through the formation of cell colonies, at low doses (> 10 ug/ml). In the presence of metabolic activation, the cell-transforming activity was detectable at all tested doses (i.e. from 20 to 200 ug/ml) and it was particularly evident in a level-II transformation amplification test when the cells were allowed to perform active proliferative activity. https://www.ncbi.nlm.nih.gov/pubmed/9434840
Interaction of a genotoxic fungicide Thiophanate methyl (MT) has been studied in vitro with calf thymus DNA. Fluorescence quenching data revealed the binding constant (K(a)=3.23 x 10(4)M(-1)) and binding capacity (n=1.1) of MT with ctDNA.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:11:51 GMT 2025
Edited
by admin
on Mon Mar 31 19:11:51 GMT 2025
Record UNII
K4N81R84L8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CALIGRAN
Preferred Name English
THIOPHANATE-METHYL
HSDB   ISO  
Common Name English
SPOT KLEEN
Brand Name English
CARBAMIC ACID, (1,2-PHENYLENEBIS(IMINOCARBONOTHIOYL))BIS-, DIMETHYL ESTER
Common Name English
METOBEN
Brand Name English
THIOPHANATE-METHYL [HSDB]
Common Name English
THIOPHANATE-METHYL [ISO]
Common Name English
O-BIS(3-METHOXYCARBONYL-2-THIOUREIDO)BENZENE
Common Name English
TOPSIN M
Brand Name English
NSC-170811
Code English
1,2-BIS(METHOXYCARBONYLTHIOUREIDO)BENZENE
Systematic Name English
METHYLTHIOFANATE
Common Name English
MILDOTHANE
Brand Name English
FUNGITOX
Brand Name English
THIOPHANATE O,O-DIMETHYL ANALOG [MI]
Common Name English
FRUMIDOR
Brand Name English
DIMETHYL 4,4'-O-PHENYLENEBIS(3-THIOALLOPHANATE)
Common Name English
CARBAMIC ACID, N,N'-(1,2-PHENYLENEBIS(IMINOCARBONOTHIOYL))BIS-, C,C'-DIMETHYL ESTER
Common Name English
CERCOBIN-M
Brand Name English
THIOPHANATE M
Common Name English
DIMETHYL (1,2-PHENYLENEBIS(IMINOCARBONOTHIOYL))BISCARBAMATE
Systematic Name English
1,2-BIS(3-(METHOXYCARBONYL)-2-THIOUREIDO)BENZENE
Systematic Name English
METHYL TOPSIN
Brand Name English
METHYL THIOPHANATE
Common Name English
ENOVIT-METHYL
Brand Name English
METHYLTHIOPHANATE
Common Name English
ALLOPHANIC ACID, 4,4'-O-PHENYLENEBIS(3-THIO-, DIMETHYL ESTER
Common Name English
THIOPHANATE METHYL
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 102001
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID1024338
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
CHEBI
35014
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
PUBCHEM
3032791
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
MERCK INDEX
m10775
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY Merck Index
NSC
170811
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
HSDB
6937
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
ALANWOOD
thiophanate-methyl
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
FDA UNII
K4N81R84L8
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
CAS
23564-05-8
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
WIKIPEDIA
Thiophanate-methyl
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
245-740-7
Created by admin on Mon Mar 31 19:11:51 GMT 2025 , Edited by admin on Mon Mar 31 19:11:51 GMT 2025
PRIMARY
Related Record Type Details
Structure of CARBENDAZIM
METABOLITE -> PARENT
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