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]

Quick facts Names, Identifiers ...

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
CAS Number	23564-05-8 Y
3D model (JSmol)	Interactive image
ChemSpider	2297683
ECHA InfoCard	100.041.567
PubChem CID	3032791
UNII	K4N81R84L8 Y
CompTox Dashboard (EPA)	DTXSID1024338
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−1
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 [77 °F], 100 kPa). Infobox references

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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.