Dipropylcarbamothioic acid S-ethyl ester (CHEM000824)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (7)XML
Record Information
Version1.0
Creation Date2009-06-17 23:53:03 UTC
Update Date2016-11-09 01:08:22 UTC
Accession NumberCHEM000824
Identification
Common NameDipropylcarbamothioic acid S-ethyl ester
ClassSmall Molecule
DescriptionN,N-dipropyl(ethylsulfanyl)formamide or ethylsulfanyl-N,N-dipropylformamide or EPTC is thiocarbamate herbicide used for control of annual grassy weeds, perennial weeds, and some broadleaf weeds in beans, forage legumes, potatoes, corn, and sweet potatoes. It is usually applied preemergence, that is before weed seeds germinate, and is usually incorporated into the soil immediately after application either mechanically or by overhead irrigation. Thiocarbamates are mainly used in agriculture as insecticides, herbicides, and fungicides. Additional uses are as biocides for industrial or other commercial applications, and in household products. Some are used for vector control in public health. Thiocarbamates are mostly liquids or solids with low melting points.
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Carbamate
  • Ether
  • Herbicide
  • Nutraceutical
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
S-Ethyl dipropylthiocarbamateKegg
S-Ethyl dipropylthiocarbamic acidGenerator
Dipropylcarbamothioate S-ethyl esterGenerator
EptamMeSH
Chemical FormulaC9H19NOS
Average Molecular Mass189.318 g/mol
Monoisotopic Mass189.119 g/mol
CAS Registry Number759-94-4
IUPAC NameN,N-dipropyl(ethylsulfanyl)formamide
Traditional Nametorbin
SMILESCCCN(CCC)C(=O)SCC
InChI IdentifierInChI=1S/C9H19NOS/c1-4-7-10(8-5-2)9(11)12-6-3/h4-8H2,1-3H3
InChI KeyGUVLYNGULCJVDO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thiocarbamic acid derivatives. These are organic compounds containing a functional group with the general structure OC(=S)NR2 or SC(=O)NR2.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiocarbonyl compounds
Sub ClassThiocarbamic acid derivatives
Direct ParentThiocarbamic acid derivatives
Alternative Parents
Substituents
  • Thiocarbamic acid derivative
  • Carbonic acid derivative
  • Sulfenyl compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid
Experimental Properties
PropertyValue
Melting Point< 25°C
Boiling PointNot Available
Solubility0.375 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
logP3.32ALOGPS
logP2.8ChemAxon
logS-2.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity55.52 m³·mol⁻¹ChemAxon
Polarizability22.57 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r6-9400000000-fe5e9c48997afd4c3c33Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-4900000000-1f169b5c884ef855796aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9800000000-70d081b80cbbe7f7a56bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0d1414e122ea5d603b45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-f0a83f000615a3f3b94eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h00-6900000000-8b2b4de56772a77e9857Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9300000000-0ea76150ac6663dbf6bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fbc-1900000000-717d4be1107a2beba313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009l-9700000000-a2279508661a11a2d433Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-bd92eb449ded8797b09eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-4900000000-ceedf619e8be12ff6874Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-9000000000-647094c7108d0d4dc81bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-c304e9232027657cfe1bSpectrum
MSMass Spectrum (Electron Ionization)splash10-002o-9300000000-1bf58f4958dee4b86e68Spectrum
Toxicity Profile
Route of ExposureInhalation (1) ; oral (1); dermal (1)
Mechanism of ToxicitySome thiocarbamates (EPTC, Molinate, Pebulate, and Cycloate) share a common mechanism of toxicity, i.e. the inhibition of acetylcholinesterase. An acetylcholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. 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.
MetabolismAs a general rule, thiocarbamates can be absorbed via the skin, mucous membranes, and the respiratory and gastrointestinal tracts. They are eliminated quite rapidly, mainly via expired air and urine. Two major pathways exist for the metabolism of thiocarbamates in mammals. One is via sulfoxidation and conjugation with glutathione. The conjugation product is then cleaved to a cysteine derivative, which is metabolized to a mercapturic acid compound. The second route is oxidation of the sulfur to a sulfoxide, which is then oxidized to a sulfone, or hydroxylation to compounds that enter the carbon metabolic pool.
Toxicity ValuesEPTC is slightly toxic via ingestion, with reported oral LD50 values of 1632 mg/kg in rats, 3160 mg/kg in mice, 112 mg/kg in cats, and 2460 mg/kg in rabbits
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThiocarbamates are widely used throughout the world and are produced in great quantities, mainly as herbicides and fungicides.
Minimum Risk LevelNot Available
Health EffectsData concerning the effects of thiocarbamates on man are scarce. However, cases of irritation and sensitization have been observed among agricultural workers. Some thiocarbamates, e.g., molinate, have an effect on sperm morphology and, consequently, on reproduction. However, no teratogenic effects have been observed. EPTC was not mutagenic when tested in a series of assays with microbial and human cell culture lines. The results of mutagenicity studies have shown that thiocarbamates containing dichloroallyl groups are highly mutagenic. Some thiocarbamates are acetylcholine esterase inhibitors. Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved.
SymptomsAs with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (2)
TreatmentTreatment of carbamate poisoning is similar to that of organophosphate poisoning in that atropine sulfate injections readily reverse the effects. For acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0251894
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID12428
ChEBI IDNot Available
PubChem Compound ID12968
Kegg Compound IDC11081
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available