Triallate (CHEM000876)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (9)XML
Record Information
Version1.0
Creation Date2009-06-17 23:53:06 UTC
Update Date2016-11-09 01:08:23 UTC
Accession NumberCHEM000876
Identification
Common NameTriallate
ClassSmall Molecule
DescriptionTriallate belongs to the thiocarbamate chemical class. It is a pre-emergence selective herbicide used to control grass weeds in field and pulse crops. It is used selectively to control wild oats, black grass, and annual meadow grass in barley, wheat, peas, lentils, rye, maize, beets, brassicas, carrots, and onions. 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
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Carbamate
  • Ether
  • Herbicide
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Triallic acidGenerator
Far goMeSH
Tri-allateMeSH
Avadex BWMeSH
Tri allateMeSH
Far-goMeSH
FarGoMeSH
Chemical FormulaC10H16Cl3NOS
Average Molecular Mass304.664 g/mol
Monoisotopic Mass303.002 g/mol
CAS Registry Number2303-17-5
IUPAC NameN,N-bis(propan-2-yl)[(2,3,3-trichloroprop-2-en-1-yl)sulfanyl]formamide
Traditional Nametriallate
SMILESCC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl
InChI IdentifierInChI=1S/C10H16Cl3NOS/c1-6(2)14(7(3)4)10(15)16-5-8(11)9(12)13/h6-7H,5H2,1-4H3
InChI KeyMWBPRDONLNQCFV-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
  • Carbonic acid derivative
  • Thiocarbamic acid derivative
  • Vinyl chloride
  • Vinyl halide
  • Sulfenyl compound
  • Chloroalkene
  • Haloalkene
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceAmber liquid
Experimental Properties
PropertyValue
Melting Point29°C
Boiling PointNot Available
Solubility0.004 mg/mL at 25°C [TOMLIN,C (1997)]
Predicted Properties
PropertyValueSource
Water Solubility0.008 g/LALOGPS
logP4.41ALOGPS
logP3.8ChemAxon
logS-4.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85 m³·mol⁻¹ChemAxon
Polarizability29.34 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, Positivesplash10-0006-9500000000-1734325a63b36fa82c77Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udl-4809000000-9f39ba8eeaf4f15c0b61Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-001i-9200000000-8240cbecf495fe405216Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0900000000-1bc876ad1d65aa05e1dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-b815b2e46ab41be5e0d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0945000000-7686998772fbf7682a0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0009000000-bfc551e4edcae01422adSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0006-0900000000-a6d6e532a5ffd84c5076Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0006-3900000000-9cc17661c4a63305337eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000l-9612000000-5a5bdc20e6e2c3f36359Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0006-3900000000-ca1f3c11cb78dbbc9565Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-000x-9800000000-6b8e5ef6ea5938094fadSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0udi-1109000000-b0e6ea4afd3c9427d8cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0619000000-a070bc8a86fa84923b56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2912000000-6f6c2cf9a3bfa9ba291dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ai-3900000000-305c84fc02f8d118b3afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0umi-0905000000-e60a7f31c6be7f69e589Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-1911000000-742ae72722c2cd985a99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-9700000000-12d34f9541e21e31414fSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9110000000-410dff592498b83ed3a2Spectrum
Toxicity Profile
Route of ExposureInhalation (1) ; oral (1); dermal (1)
Mechanism of ToxicityThe metabolic products of triallate, diallate and sulfallate appear to be mutagenic or carcinogenic. In particular, the 2-chloro-allyl group is responsible for the mutagenicity of these herbicides. These metabolites likely bind to or disrupt DNA causes base-pair subsitutions. Diallate has been shown to be a carcinogen in mice. Some 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 ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC. Sulfallate, a metabolite of triallate, is classified by IARC as possibly carcinogenic to humans (Group 2B). Diallate, another metabolite, is not classifiable as to its carcinogenicity to humans (Group 3). (3)
Uses/SourcesThiocarbamates are widely used throughout the world and are produced in great quantities, mainly as herbicides and fungicides.
Minimum Risk LevelNot Available
Health EffectsTriallate is mutagenic. Data 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. 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)
TreatmentFor 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 IDHMDB0259144
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 ID5342
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC18813
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available