ethoprophos

Also known as O-ethyl S,S-dipropyl dithiophosphate, Phosphorodithioic acid, O-ethyl S,S-dipropyl ester, Ethoprop

Ethoprophos (or ethoprop) is an organophosphate ester with the formula C8H19O2PS2. It is a clear yellow to colourless liquid that has a characteristic mercaptan-like odour. It is used as an insecticide and nematicide and it is an acetylcholinesterase inhibitor.

Chemical data

Formula: C8H19O2PS2
Molecular weight: 242.3 g/mol
IUPAC name: 1-[ethoxy(propylsulfanyl)phosphoryl]sulfanylpropane
SMILES: CCCSP(=O)(OCC)SCCC
InChIKey: VJYFKVYYMZPMAB-UHFFFAOYSA-N
XLogP: 3.6
Polar surface area: 76.9 Å²
H-bond donors: 0
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 242.056
Has use: nematicide

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chemical formula: C₈H₁₉O₂PS₂
canonical SMILES: CCCSP(=O)(OCC)SCCC
Commons category: Ethoprophos
subject has role: carcinogen

Sources (3)

via Wikidata · CC0

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Encyclopedic overview

9 sections

Contents

Synthesis
Applications
Toxicology
Mechanism of action
Metabolism
Distribution & Excretion
Effects on animals
Exposure
References

== Synthesis == Ethoprop can be synthesised by reacting phosphoryl chloride with two equivalents of n-propylmercaptan and one equivalent of sodium ethoxide. A second pathway is reacting n-propylmercaptan and sodium ethoxide with phosphorus trichloride to yield ethoxy-bis(propylsulfanyl)phosphane, which can then be oxidized by hydrogen peroxide to yield the product. thumb|299x299px|Two syntheses of ethoprop. The only difference is the order in which the alkyl groups are attached|alt=|left thumb|500x500px|A different synthesis of ethoprop starting from phosphorus trichloride|alt=|left

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