Basic Info

Common NameThiophanate-Methyl(F05147)
2D Structure
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.

FRCD IDF05147
CAS Number23564-05-8
PubChem CID3032791
FormulaC12H14N4O4S2
IUPAC Name

methyl N-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate

InChI Key

QGHREAKMXXNCOA-UHFFFAOYSA-N

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)

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            Thiophanate-methyl
        
            Cercobin methyl
        
            23564-05-8
        
            Thiophanate M
        
            Methylthiofanate
        
            THIOPHANATE METHYL
        
            Methylthiophanate
        
            Mildothane
        
            Neotopsin
        
            Fungo
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsMonocyclic 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
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight342.388
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Complexity407
Monoisotopic Mass342.046
Exact Mass342.046
XLogP2.6
Formal Charge0
Heavy Atom Count22
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.6212
Human Intestinal AbsorptionHIA-0.8033
Caco-2 PermeabilityCaco2-0.5552
P-glycoprotein SubstrateNon-substrate0.7446
P-glycoprotein InhibitorNon-inhibitor0.7923
Non-inhibitor0.9796
Renal Organic Cation TransporterNon-inhibitor0.9666
Distribution
Subcellular localizationMitochondria0.7852
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7094
CYP450 2D6 SubstrateNon-substrate0.8160
CYP450 3A4 SubstrateNon-substrate0.7087
CYP450 1A2 InhibitorNon-inhibitor0.5103
CYP450 2C9 InhibitorInhibitor0.5204
CYP450 2D6 InhibitorNon-inhibitor0.9519
CYP450 2C19 InhibitorNon-inhibitor0.6718
CYP450 3A4 InhibitorNon-inhibitor0.9214
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8738
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9831
Non-inhibitor0.9271
AMES ToxicityAMES toxic0.9107
CarcinogensNon-carcinogens0.8074
Fish ToxicityHigh FHMT0.9983
Tetrahymena Pyriformis ToxicityHigh TPT0.9752
Honey Bee ToxicityLow HBT0.6814
BiodegradationNot ready biodegradable0.9781
Acute Oral ToxicityIV0.6104
Carcinogenicity (Three-class)Non-required0.6700

Model Value Unit
Absorption
Aqueous solubility-3.2907LogS
Caco-2 Permeability0.7012LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7433LD50, mol/kg
Fish Toxicity1.3894pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3896pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Mangoes0163030European Union101/01/2012
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union601/01/2012
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union601/01/2012
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union601/01/2012
Others (2)0110990European Union0.1*01/01/2012
Tree nuts0120000European Union0.2*01/01/2012
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.2*01/01/2012
Brazil nuts0120020European Union0.2*01/01/2012
Cashew nuts0120030European Union0.2*01/01/2012
Chestnuts0120040European Union0.2*01/01/2012
Coconuts (Areca nuts/betel nuts,)0120050European Union0.2*01/01/2012
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.2*01/01/2012
Macadamias0120070European Union0.2*01/01/2012
Pecans (Hickory nuts,)0120080European Union0.2*01/01/2012
Papayas (Akee apples, Feijoas/pineapple guavas, Langsats/lanzones/longkongs, Mangosteens, Naranjillas/lulos, Paw paws, Tamarillos,)0163040European Union101/01/2012
Granate apples/pomegranates0163050European Union0.1*01/01/2012
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.2*01/01/2012
Pistachios0120100European Union0.2*01/01/2012
Walnuts0120110European Union0.2*01/01/2012
Others (2)0120990European Union0.2*01/01/2012

References

TitleJournalDatePubmed ID
[Simultaneous determination of seven high risk pesticide residues in royal jelly by high performance liquid chromatography-tandem mass spectrometry].Se Pu2018 Feb 829582599
Determination of trace thiophanate-methyl and its metabolite carbendazim withteratogenic risk in red bell pepper (Capsicumannuum L.) by surface-enhanced Ramanimaging technique.Food Chem2017 Mar 127719947
[Simultaneous determination of three benzimidazole fungicides in fruits andvegetables by capillary electrophoresis based on bacterial cellulose].Se Pu2017 Dec 829372782
The influence of chemical protection on the content of heavy metals in wheat(Triticum aestivum L.) growing on the soil enriched with granular sludge.Environ Monit Assess2017 Aug28762146
Influence of different planting seasons of six leaf vegetables on residues offive pesticides.J Agric Food Chem2013 Sep 2523978278
Spinach or amaranth may represent highest residue of thiophanate-methyl with openfield application on six leaf vegetables.Bull Environ Contam Toxicol2013 Apr23242258
Effect of preharvest anti-fungal compounds on Aspergillus steynii and A. carbonarius under fluctuating and extreme environmental conditions.Int J Food Microbiol2012 Oct 122947301
[Determination of thiophanate-methyl and carbendazim in cucumber and soil byQuEChERS-high performance liquid chromatography-triple quadrupole tandem massspectrometry].Se Pu2012 Jan22667099
[Rapid determination of 6 pesticide residues in tomato paste by ultra performanceliquid chromatography-tandem mass spectrometry].Se Pu2011 Nov22393693
Determination of sixteen pesticides in peppers using high-performance liquidchromatography/mass spectrometry.J Environ Sci Health B201121726151
Determination of carbendazim, thiophanate, thiophanate-methyl and benomylresidues in agricultural products by liquid chromatography-tandem massspectrometry.Shokuhin Eiseigaku Zasshi201121720119
Dissipation study of thiophanate methyl residue in/on grapes (Vitis vinifera L.) in India.Bull Environ Contam Toxicol2010 May20401648
Ionic liquid based dispersive liquid-liquid microextraction for the extraction ofpesticides from bananas.J Chromatogr A2009 Oct 2319700165
Description of Cryptosporiopsis kienholzii and species profiles of Neofabraea in major pome fruit growing districts in the Pacific Northwest USA.Mycol Res2009 Nov19733662
Pesticide extraction from table grapes and plums using ionic liquid baseddispersive liquid-liquid microextraction.Anal Bioanal Chem2009 Dec19779926
[Study on usage of pesticides in various countries].Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku200718220053
A simple and rapid spectrophotometric method for determination ofthiophanate-methyl in commercial formulations and its residues in foodstuffs.J AOAC Int2004 Jul-Aug15295873
[Effect of pesticides on field-controlling root rot of Vicia faba].Ying Yong Sheng Tai Xue Bao2002 Aug12418252
[Effects of Atractylodes macrocephala seeds coated with SCF on field diseases].Zhong Yao Cai2002 Apr12583169
Postharvest-applied agrochemicals and their residues in fresh fruits andvegetables.J Assoc Off Anal Chem1991 Sep-Oct1783584