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Thiophanate-methyl

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Thiophanate-methyl
Chemical structure of thiophanate-methyl.
Names
Preferred IUPAC name Dimethyl N,N′-dicarbamate
Other names Dimethyl 4,4′-(o-phenylene)bis(3-thioallophanate)
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.041.567 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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)Key: QGHREAKMXXNCOA-UHFFFAOYSA-N
SMILES
  • COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC
Properties
Chemical formula C12H14N4O4S2
Molar mass 342.39 g·mol
Appearance white powder
Melting point 172 °C (342 °F; 445 K)
Solubility in water 26.6 mg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Thiophanate-methyl is an organic compound with the formula C6H4(NHC(S)NH(CO)OCH3)2. The compound is a colorless or white solid, although commercial samples are generally tan-colored. It is prepared from o-phenylenediamine. It is a widely used fungicide used on tree, vine, and root crops. In Europe it is applied to tomato, wine grapes, beans, wheat, and aubergine.

Methods for its analysis have received considerable attention. It is commonly used to treat botrytis bunch rot and gray mold caused by Botrytis cinerea strawberry in California. Thiophanate-methyl acts as a fungicide via its primary metabolite carbendazim.

References

  1. "Thiophanate-methyl" (PDF). Environmental Protection Agency.
  2. European Food Safety Authority; et al. (2018). "Peer review of the pesticide risk assessment of the active substance thiophanate-methyl". EFSA Journal. 16 (1): e05133. doi:10.2903/j.efsa.2018.5133. PMC 7009477. PMID 32625680. S2CID 79538931.
  3. Mol, Hans G. J.; Plaza-Bolaños, Patricia; Zomer, Paul; De Rijk, Theo C.; Stolker, Alida A. M.; Mulder, Patrick P. J. (2008). "Toward a Generic Extraction Method for Simultaneous Determination of Pesticides, Mycotoxins, Plant Toxins, and Veterinary Drugs in Feed and Food Matrixes". Analytical Chemistry. 80 (24): 9450–9459. doi:10.1021/ac801557f. PMID 19072261.
  4. Romero-González, R.; Garrido Frenich, A.; Martínez Vidal, J.L.; Prestes, O.D.; Grio, S.L. (2011). "Simultaneous determination of pesticides, biopesticides and mycotoxins in organic products applying a quick, easy, cheap, effective, rugged and safe extraction procedure and ultra-high performance liquid chromatography–tandem mass spectrometry". Journal of Chromatography A. 1218 (11): 1477–1485. doi:10.1016/j.chroma.2011.01.034. PMID 21292276.
  5. Kiljanek, Tomasz; Niewiadowska, Alicja; Semeniuk, Stanisław; Gaweł, Marta; Borzęcka, Milena; Posyniak, Andrzej (2016). "Multi-residue method for the determination of pesticides and pesticide metabolites in honeybees by liquid and gas chromatography coupled with tandem mass spectrometry—Honeybee poisoning incidents". Journal of Chromatography A. 1435: 100–114. doi:10.1016/j.chroma.2016.01.045. PMID 26830634.
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