Thiophanate-methyl

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 ;
3D model (JSmol)	Interactive image;
ChemSpider	2297683;
ECHA InfoCard	100.041.567
PubChem CID	3032791;
UNII	K4N81R84L8 ;
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

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.