Thiophanate-Methyl
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Basic Info
Common Name | Thiophanate-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 ID | F05147 |
CAS Number | 23564-05-8 |
PubChem CID | 3032791 |
Formula | C12H14N4O4S2 |
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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Not available |
Intermediate Tree Nodes | Not available |
Direct Parent | Benzene and substituted derivatives |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
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 |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 342.388 |
Hydrogen Bond Donor Count | 4 |
Hydrogen Bond Acceptor Count | 6 |
Rotatable Bond Count | 4 |
Complexity | 407 |
Monoisotopic Mass | 342.046 |
Exact Mass | 342.046 |
XLogP | 2.6 |
Formal Charge | 0 |
Heavy Atom Count | 22 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.6212 |
Human Intestinal Absorption | HIA- | 0.8033 |
Caco-2 Permeability | Caco2- | 0.5552 |
P-glycoprotein Substrate | Non-substrate | 0.7446 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.7923 |
Non-inhibitor | 0.9796 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9666 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7852 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7094 |
CYP450 2D6 Substrate | Non-substrate | 0.8160 |
CYP450 3A4 Substrate | Non-substrate | 0.7087 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.5103 |
CYP450 2C9 Inhibitor | Inhibitor | 0.5204 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9519 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.6718 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9214 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8738 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9831 |
Non-inhibitor | 0.9271 | |
AMES Toxicity | AMES toxic | 0.9107 |
Carcinogens | Non-carcinogens | 0.8074 |
Fish Toxicity | High FHMT | 0.9983 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9752 |
Honey Bee Toxicity | Low HBT | 0.6814 |
Biodegradation | Not ready biodegradable | 0.9781 |
Acute Oral Toxicity | IV | 0.6104 |
Carcinogenicity (Three-class) | Non-required | 0.6700 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.2907 | LogS |
Caco-2 Permeability | 0.7012 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.7433 | LD50, mol/kg |
Fish Toxicity | 1.3894 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.3896 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Mangoes | 0163030 | European Union | 1 | 01/01/2012 | |
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 6 | 01/01/2012 | |
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 6 | 01/01/2012 | |
Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 6 | 01/01/2012 | |
Others (2) | 0110990 | European Union | 0.1* | 01/01/2012 | |
Tree nuts | 0120000 | European Union | 0.2* | 01/01/2012 | |
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.2* | 01/01/2012 | |
Brazil nuts | 0120020 | European Union | 0.2* | 01/01/2012 | |
Cashew nuts | 0120030 | European Union | 0.2* | 01/01/2012 | |
Chestnuts | 0120040 | European Union | 0.2* | 01/01/2012 | |
Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.2* | 01/01/2012 | |
Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.2* | 01/01/2012 | |
Macadamias | 0120070 | European Union | 0.2* | 01/01/2012 | |
Pecans (Hickory nuts,) | 0120080 | European Union | 0.2* | 01/01/2012 | |
Papayas (Akee apples, Feijoas/pineapple guavas, Langsats/lanzones/longkongs, Mangosteens, Naranjillas/lulos, Paw paws, Tamarillos,) | 0163040 | European Union | 1 | 01/01/2012 | |
Granate apples/pomegranates | 0163050 | European Union | 0.1* | 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 ... | 0120090 | European Union | 0.2* | 01/01/2012 | |
Pistachios | 0120100 | European Union | 0.2* | 01/01/2012 | |
Walnuts | 0120110 | European Union | 0.2* | 01/01/2012 | |
Others (2) | 0120990 | European Union | 0.2* | 01/01/2012 |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
[Simultaneous determination of seven high risk pesticide residues in royal jelly by high performance liquid chromatography-tandem mass spectrometry]. | Se Pu | 2018 Feb 8 | 29582599 |
Determination of trace thiophanate-methyl and its metabolite carbendazim withteratogenic risk in red bell pepper (Capsicumannuum L.) by surface-enhanced Ramanimaging technique. | Food Chem | 2017 Mar 1 | 27719947 |
[Simultaneous determination of three benzimidazole fungicides in fruits andvegetables by capillary electrophoresis based on bacterial cellulose]. | Se Pu | 2017 Dec 8 | 29372782 |
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 Assess | 2017 Aug | 28762146 |
Influence of different planting seasons of six leaf vegetables on residues offive pesticides. | J Agric Food Chem | 2013 Sep 25 | 23978278 |
Spinach or amaranth may represent highest residue of thiophanate-methyl with openfield application on six leaf vegetables. | Bull Environ Contam Toxicol | 2013 Apr | 23242258 |
Effect of preharvest anti-fungal compounds on Aspergillus steynii and A. carbonarius under fluctuating and extreme environmental conditions. | Int J Food Microbiol | 2012 Oct 1 | 22947301 |
[Determination of thiophanate-methyl and carbendazim in cucumber and soil byQuEChERS-high performance liquid chromatography-triple quadrupole tandem massspectrometry]. | Se Pu | 2012 Jan | 22667099 |
[Rapid determination of 6 pesticide residues in tomato paste by ultra performanceliquid chromatography-tandem mass spectrometry]. | Se Pu | 2011 Nov | 22393693 |
Determination of sixteen pesticides in peppers using high-performance liquidchromatography/mass spectrometry. | J Environ Sci Health B | 2011 | 21726151 |
Determination of carbendazim, thiophanate, thiophanate-methyl and benomylresidues in agricultural products by liquid chromatography-tandem massspectrometry. | Shokuhin Eiseigaku Zasshi | 2011 | 21720119 |
Dissipation study of thiophanate methyl residue in/on grapes (Vitis vinifera L.) in India. | Bull Environ Contam Toxicol | 2010 May | 20401648 |
Ionic liquid based dispersive liquid-liquid microextraction for the extraction ofpesticides from bananas. | J Chromatogr A | 2009 Oct 23 | 19700165 |
Description of Cryptosporiopsis kienholzii and species profiles of Neofabraea in major pome fruit growing districts in the Pacific Northwest USA. | Mycol Res | 2009 Nov | 19733662 |
Pesticide extraction from table grapes and plums using ionic liquid baseddispersive liquid-liquid microextraction. | Anal Bioanal Chem | 2009 Dec | 19779926 |
[Study on usage of pesticides in various countries]. | Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku | 2007 | 18220053 |
A simple and rapid spectrophotometric method for determination ofthiophanate-methyl in commercial formulations and its residues in foodstuffs. | J AOAC Int | 2004 Jul-Aug | 15295873 |
[Effect of pesticides on field-controlling root rot of Vicia faba]. | Ying Yong Sheng Tai Xue Bao | 2002 Aug | 12418252 |
[Effects of Atractylodes macrocephala seeds coated with SCF on field diseases]. | Zhong Yao Cai | 2002 Apr | 12583169 |
Postharvest-applied agrochemicals and their residues in fresh fruits andvegetables. | J Assoc Off Anal Chem | 1991 Sep-Oct | 1783584 |