thiophanate-methyl

Also known as 1,2-Di-(3-methoxycarbonyl-2-thioureido)benzene, dimethyl N,N'-[1,2-phenylenebis(iminocarbonothioyl)]bis[carbamate], dimethyl N,N'-[1,2-phenylenebis(azanediylcarbonothioyl)]dicarbamate, dimethyl 4,4'-(o-phenylene)bis(3-thioallophanate), Methyl thiophanate, o-Bis(3-methoxycarbonyl-2-thioureido)benzene, Methylthiofanate, 1,2-Bis(methoxycarbonylthioureido)benzene

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.

Chemical data

Formula: C12H14N4O4S2
Molecular weight: 342.4 g/mol
IUPAC name: methyl N-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate
SMILES: COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC
InChIKey: QGHREAKMXXNCOA-UHFFFAOYSA-N
XLogP: 2.6
Polar surface area: 165 Å²
H-bond donors: 4
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 342.046
Has use: fungicide

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chemical formula: C₁₂H₁₄N₄O₄S₂
canonical SMILES: COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC
Commons category: Thiophanate-methyl

Sources (3)

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Encyclopedic overview

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Contents

References

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.

Excerpted from Wikipedia’s “thiophanate-methyl” article, available under the CC BY-SA 4.0 licence.