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Record Information
Version2.0
Creation Date2009-06-17 23:53:06 UTC
Update Date2014-12-24 20:23:03 UTC
Accession NumberT3D1017
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.
Compound Type
  • Carbamate
  • Ether
  • Herbicide
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
2,3,3-Trichloro-2-propene-1-thiol diisopropylcarbamate
2,3,3-Trichloroallyl diisopropylthiocarbamate
2,3,3-Trichloroallyl N,N-diisopropylthiocarbamate
2-Propene-1-thiol, 2,3,3-trichloro-, diisopropylcarbamate
Avadex be
Avadex BW
Caswell No. 870A
Diisopropylthiocarbamic acid S-(2,3,3-trichloroallyl) ester
DIIsopropyltrichloroallylthiocarbamate
Dipthal
N,N-Diisopropyl-2,3,3-trichlorallyl-thiolcarbamate
RCRA waste no. U389
S-(2,3,3-Trichloro-2-propenyl) diisopropylthiocarbamate
S-(2,3,3-Trichloroallyl) diisopropylthiocarbamate
S-(2,3,3-Trichloroallyl) N,N-diisopropylthiocarbamate
S-(2,3,3-Trichloroallyl)diisopropylthiocarbamate
S-(2,3,3-trichloroprop-2-en-1-yl) diisopropylthiocarbamate
S-2,3,3-Trichloroallyl diisopropylthiocarbamate
S-2,3,3-Trichloroallyl N,N-diisopropylthiocarbamate
S-2,3,3-Trichloroallyl-N,N-diisopropylthiolcarbamate
Tri-allate
Triallic acid
Triamyl
Trichloroallyl dIIsopropylthiocarbamate
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 KeyInChIKey=MWBPRDONLNQCFV-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)]
LogPNot Available
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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-1734325a63b36fa82c772021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udl-4809000000-9f39ba8eeaf4f15c0b612021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-001i-9200000000-8240cbecf495fe4052162021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0900000000-1bc876ad1d65aa05e1db2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-b815b2e46ab41be5e0d22021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0945000000-7686998772fbf7682a0f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0009000000-bfc551e4edcae01422ad2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0006-0900000000-a6d6e532a5ffd84c50762021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0006-3900000000-9cc17661c4a63305337e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000l-9612000000-5a5bdc20e6e2c3f363592021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0006-3900000000-ca1f3c11cb78dbbc95652021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-000x-9800000000-6b8e5ef6ea5938094fad2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0udi-1109000000-b0e6ea4afd3c9427d8cb2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0619000000-a070bc8a86fa84923b562016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2912000000-6f6c2cf9a3bfa9ba291d2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ai-3900000000-305c84fc02f8d118b3af2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0umi-0905000000-e60a7f31c6be7f69e5892016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-1911000000-742ae72722c2cd985a992016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-9700000000-12d34f9541e21e31414f2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9110000000-410dff592498b83ed3a22014-09-20View Spectrum
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5543
ChEMBL IDCHEMBL1884767
ChemSpider ID5342
KEGG IDC18813
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDD014214
Stitch IDTriallate
PDB IDNot Available
ACToR ID6553
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1017.pdf
General References
  1. IPCS Intox Database (1987). Antimony pentoxide. [Link]
  2. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
3. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. doi: 10.1111/j.1476-5381.2009.00614.x. Epub 2010 Feb 5. [20136829 ]
General Function:
Cytokine activity
Specific Function:
Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
Gene Name:
IL1A
Uniprot ID:
P01583
Molecular Weight:
30606.29 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.48 uMBSK_BE3C_IL1a_upBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Serine-type endopeptidase inhibitor activity
Specific Function:
Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
Gene Name:
SERPINE1
Uniprot ID:
P05121
Molecular Weight:
45059.695 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.48 uMBSK_BE3C_PAI1_downBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.90 uMATG_PXRE_CISAttagene
AC509.70 uMNVS_NR_hPXRNovascreen
AC504.89 uMATG_PXRE_CISAttagene
AC502.42 uMNVS_NR_hPXRNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Urokinase plasminogen activator receptor activity
Specific Function:
Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
Gene Name:
PLAUR
Uniprot ID:
Q03405
Molecular Weight:
36977.62 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.44 uMBSK_BE3C_uPAR_upBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC505.16 uMCLZD_CYP2B6_6CellzDirect
AC506.02 uMCLZD_CYP2B6_24CellzDirect
AC504.56 uMCLZD_CYP2B6_48CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC505.61 uMCLZD_CYP3A4_24CellzDirect
AC507.08 uMCLZD_CYP3A4_48CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]