Thiophanate-methyl

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.[1] In Europe it is applied to tomato, wine grapes, beans, wheat, and aubergine.[2]

Thiophanate-methyl
Chemical structure of thiophanate-methyl.
Names
Preferred IUPAC name
Dimethyl N,N′-[1,2-phenylenebis(azanediylcarbonothioyl)]dicarbamate
Other names
Dimethyl 4,4′-(o-phenylene)bis(3-thioallophanate)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.041.567
UNII
  • 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
  • COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC
Properties
C12H14N4O4S2
Molar mass 342.39 g·mol−1
Appearance white powder
Melting point 172 °C (342 °F; 445 K)
26.6 mg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methods for its analysis have received considerable attention.[3][4][5] It is commonly used to treat botrytis bunch rot and gray mold caused by Botrytis cinerea strawberry in California.[6] 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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