Disulfoton (CED0000026)

Record Information
Version1.0
Creation Date2009-03-06 18:57:58 UTC
Update Date2026-08-24 18:14:20 UTC
Accession NumberCHEM000034
Identification
Common NameDisulfoton
ClassSmall Molecule
Description
Disulfoton is an exogenous liquid compound with the formula C8H19O2PS3 and an average molecular weight of 274.40 g/mol. Disulfoton belongs to the dithiophosphate o-esters, a subclass of organic dithiophosphoric acids and derivatives within the organic compounds. It is used as an agrochemical, biocide, and acaricide. Biologically and chemically, disulfoton acts as an EC 3.1.1.7 (acetylcholinesterase) inhibitor. Its protein targets include acetylcholinesterase (ACHE), cytochrome P450 2B6 (CYP2B6), cytochrome P450 2C9 (CYP2C9), interleukin-1 alpha (IL1A), transforming growth factor beta-1 proprotein (TGFB1), and one other protein. The toxic metabolites of disulfoton—primarily disulfoton sulfone, disulfoton sulfoxide, demeton S-sulfone, and demeton S-sulfoxide—inhibit acetylcholinesterase in nervous tissue. This inhibition leads to the accumulation of acetylcholine at the nicotinic and muscarinic cholinergic receptors of nerve synapses, resulting in the overstimulation of effector organs and cholinergic nerves. Disulfoton is found in or released from seven recorded sources. These include food preservation and the preparation of malt within the food, food processing and cookware category. In the electrical and electronic equipment category, it is associated with hybrid capacitors and electrically stimulated smoking devices. Additionally, it is found in household cleaning and consumer products, specifically within perfumes, soaps, detergents, and cigar cigarettes.
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Human Neurotoxin
  • Organic Compound
  • Organophosphate
  • Pesticide
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
EthylthiometonChEBI
O,O-Diethyl S-(2-(ethylthio)ethyl) dithiophosphateChEBI
O,O-Diethyl S-(2-ethylmercaptoethyl) dithiophosphateChEBI
Phosphorodithioic acid, O,O-diethyl S-(2-(ethylthio)ethyl) esterChEBI
S-[2-(Ethylsulfanyl)ethyl] O,O-dimethyl dithiophosphateChEBI
O,O-Diethyl S-(2-(ethylthio)ethyl) dithiophosphoric acidGenerator
O,O-Diethyl S-(2-ethylmercaptoethyl) dithiophosphoric acidGenerator
Phosphorodithioate, O,O-diethyl S-(2-(ethylthio)ethyl) esterGenerator
S-[2-(Ethylsulfanyl)ethyl] O,O-dimethyl dithiophosphoric acidGenerator
S-[2-(Ethylsulphanyl)ethyl] O,O-dimethyl dithiophosphateGenerator
S-[2-(Ethylsulphanyl)ethyl] O,O-dimethyl dithiophosphoric acidGenerator
DisulphotonGenerator
Di systonMeSH
DisystonMeSH
DemetonMeSH
Di-systonMeSH
ThiodemetonMeSH
Chemical FormulaC8H19O2PS3
Average Molecular Mass274.404 g/mol
Monoisotopic Mass274.028 g/mol
CAS Registry Number298-04-4
IUPAC NameO,O-diethyl {[2-(ethylsulfanyl)ethyl]sulfanyl}phosphonothioate
Traditional NameO,O-diethyl [2-(ethylsulfanyl)ethyl]sulfanylphosphonothioate
SMILESCCOP(=S)(OCC)SCCSCC
InChI IdentifierInChI=1S/C8H19O2PS3/c1-4-9-11(12,10-5-2)14-8-7-13-6-3/h4-8H2,1-3H3
InChI KeyDOFZAZXDOSGAJZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic dithiophosphoric acids and derivatives
Sub ClassDithiophosphate O-esters
Direct ParentDithiophosphate O-esters
Alternative Parents
Substituents
  • Dithiophosphate o-ester
  • Dithiophosphate s-ester
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organothiophosphorus compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical Roles
Organoleptic EffectsNot Available
Physical Properties
StateLiquid
AppearanceColorless (pure) or dark yellow (technical grade) oil.
Experimental Properties
PropertyValue
Melting Point-25°C
Boiling PointNot Available
Solubility0.0163 mg/mL at 20 °C [BOWMAN,BT & SANS,WW (1983A)]
Predicted Properties
PropertyValueSource
Water Solubility0.0092 g/LALOGPS
logP4.11ALOGPS
logP3.03ChemAxon
logS-4.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity74.12 m³·mol⁻¹ChemAxon
Polarizability29.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-9560000000-9bf6e1eb5b32189fa05eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-9720000000-8bca5c80358331bf4e35Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01p9-9110000000-7495c438425dc6f45bd4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-63ab2f848de48c719200Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-8790000000-84a300807312877e3e26Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9550000000-f4d95badb9b9d9a3c055Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gwb-5930000000-a170a87f479eadd5c40eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dr-9310000000-0356a92bb41107ea8420Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9400000000-123e612083412f9afbefNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-c329bb1b708cbec1f626Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0090000000-a7eefd959b907e8b58a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0h3r-1930000000-35347e0e3252d7f19126Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-0900000000-e750208bc3eb6dc08abcNot AvailableView Spectrum
MSMS Spectrumsplash10-002r-9200000000-18197bdfeb7682331a47Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityDisulfoton is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelAcute Inhalation: 0.006 mg/m3 (3) Intermediate Inhalation: 0.0002 mg/m3 (3) Acute Oral: 0.001 mg/kg/day (3) Intermediate Oral: 0.00009 mg/kg/day (3) Chronic Oral: 0.00006 mg/kg/day (3)
SymptomsDepending on the amount of disulfoton that enters the body, effects on the nervous system, such as narrowing of the pupils, vomiting, diarrhea, drooling, difficulty in breathing, tremors, convulsions, and even death may occur. Skin contact with disulfoton may cause weakness and fatigue. (2)
TreatmentIf the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
25.0mg/kgNot AvailableRatLD50DermalexperimentalT23
6.8mg/kgNot AvailableRatLD50OralexperimentalT23
9.4mg/kgNot AvailableRatLD50IntraperitonealexperimentalT23
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAcetylcholinesteraseP07140Drosophila melanogasterPredicted (SEA)0.467095
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthaseB7UJP3Escherichia coli O127:H6 (strain E2348/69 / EPEC)Predicted (SEA)10.8989
Click to view 3D structureLysophosphatidic acid receptor 3Q9UBY5HumansPredicted (SEA)542.531
Lysophosphatidic acid receptor 2 structureClick to view 3D structureLysophosphatidic acid receptor 2Q9HBW0HumansPredicted (SEA)919.866
Lysophosphatidic acid receptor 1 structureClick to view 3D structureLysophosphatidic acid receptor 1Q92633HumansPredicted (SEA)4077.04
Autotaxin structureClick to view 3D structureAutotaxinQ13822HumansPredicted (SEA)4363.68
Diacylglycerol acyltransferase/mycolyltransferase Ag85C structureClick to view 3D structureDiacylglycerol acyltransferase/mycolyltransferase Ag85CP9WQN9Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)402.247
Lysophosphatidic acid receptor 6 structureClick to view 3D structureLysophosphatidic acid receptor 6P43657HumansPredicted (SEA)79.4062
Click to view 3D structureMonoglyceride lipaseO35678Mus musculusPredicted (SEA)4936.26
Click to view 3D structureFatty-acid amide hydrolase 1O08914Mus musculusPredicted (SEA)5678.09
Click to view 3D structureCarbamate kinaseO97438Giardia intestinalisPredicted (SEA)7.08428
Click to view 3D structureCannabinoid receptor 1P47746Mus musculusPredicted (SEA)5224.07
Click to view 3D structureAcetylcholinesteraseP21836Mus musculusPredicted (SEA)6891.14
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)5568.17
Click to view 3D structureLiver carboxylesteraseQ29550Sus scrofaPredicted (SEA)3197.58
Gasdermin-D structureClick to view 3D structureGasdermin-DP57764HumansPredicted (SEA)14.2464
Click to view 3D structureGasdermin-DQ9D8T2Mus musculusPredicted (SEA)14.2464
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)7731.83
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)7711.35
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)7758.06
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)7742.26
Click to view 3D structureHistidine biosynthesis bifunctional protein HisBP06987Escherichia coli O26:H11 str. CFSAN001629Predicted (SEA)347.208
Click to view 3D structureLysophosphatidic acid receptor 4Q99677HumansPredicted (SEA)1960.87
Click to view 3D structureAminodeoxyfutalosine nucleosidaseQ9ZMY2Helicobacter pylori (strain J99 / ATCC 700824) (Campylobacter pylori J99)Predicted (SEA)937.538
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)7739.07
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansKnownThe toxic metabolites of disulfoton, mainly disulfoton sulfoxide, disulfoton sulfone, demeton S-sulfoxide and demeton S-sulfone, inhibit acetylcholinesterase in nervous tissue. The inhibition of acetylcholinesterase results in the accumulation of acetylcholine at the muscarinic and nicotinic cholinergic receptors of nerve synapses, which causes an overstimulation of cholinergic nerves and effector organs. (L123)
Interleukin-1 alpha structureClick to view 3D structureInterleukin-1 alphaP01583HumansKnownNot Available
Transforming growth factor beta-1 proprotein structureClick to view 3D structureTransforming growth factor beta-1 proproteinP01137HumansKnownNot Available
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansKnownNot Available
Click to view 3D structureUDP-glucuronosyltransferase 1A1P22309HumansKnownNot Available
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDisulfoton
Chemspider IDNot Available
ChEBI ID38661
PubChem Compound ID3118
Kegg Compound IDC18400
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15294458
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22818267
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22968680
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23303564