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Record Information
Version2.0
Creation Date2009-06-17 23:53:02 UTC
Update Date2014-12-24 20:22:59 UTC
Accession NumberT3D0956
Identification
Common NameDi-allate
ClassSmall Molecule
DescriptionDiallate is a thiocarbamate herbicide used to control weeds and grasses amongst crops. It can be applied to the soil before planting or to the growing crops. It is used on alfalfa, alsike clover, barley, corn, flax, soybeans, lentils, peas, potatoes, red clover, sugar beets and sweet clover. 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-DCDT
2,3-Dichlorallyl-N,N-(diisopropyl)-thiocarbamate
2,3-Dichloro-2-propene-1-thiol, diisopropylcarbamate
2,3-Dichloro-2-Propene-1-Thiol, S-2,3-Diisopropyl carbamate
2,3-Dichloroallyl Diisopropylthiocarbamate
2,3-Dichloroallyl N,N-diisopropylthiolcar bamate
2,3-Dichloroallyl N,N-diisopropylthiolcarbamate
2-Propene-1-thiol, 2,3-dichloro-, diisopropylcarbamate
Avadex
Avadex I
Avadex II
Caswell No. 299
Cis-diallate
DATC
DCDT
Di-allic acid
Di-isopropylthiolocarbamate de S-(2,3-dichloro allyle)
Diallaat
Diallat
Diallate
Dichloroallyl dIIsopropylthiocarbamate
Diisopropylthiocarbamic acid, S-(2,3-dichloroallyl) ester
Propene-1-thiol, 2,3-dichloro-, diisopropylcarbamate
Pyradex
RCRA waste no. U062
Rcra waste number U062
S-(2,3-Dichlor-allyl)-N,N-diisopropyl-monothiocarbamaat
S-(2,3-Dichloro-allil)-N,N-diisopropil-monotiocarbammato
S-(2,3-Dichloroallyl) diisopropyl-thiocarbamate
S-(2,3-Dichloroallyl) Diisopropylthiocarbamate
S-2,3-Dichloroallyl diisopropylthiocarbamate
S-2,3-Dichloroallyl N,N-diisopropylthiolcarbamate
S-[(2Z)-2,3-Dichloro-2-propenyl] diisopropylthiocarbamate
S-[2,3-dichloroprop-2-en-1-yl] diisopropylthiocarbamate
Chemical FormulaC10H17Cl2NOS
Average Molecular Mass270.219 g/mol
Monoisotopic Mass269.041 g/mol
CAS Registry Number2303-16-4
IUPAC NameN,N-bis(propan-2-yl){[(2Z)-2,3-dichloroprop-2-en-1-yl]sulfanyl}formamide
Traditional NameN,N-diisopropyl{[(2Z)-2,3-dichloroprop-2-en-1-yl]sulfanyl}formamide
SMILESCC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl
InChI IdentifierInChI=1S/C10H17Cl2NOS/c1-7(2)13(8(3)4)10(14)15-6-9(12)5-11/h5,7-8H,6H2,1-4H3/b9-5-
InChI KeyInChIKey=SPANOECCGNXGNR-UITAMQMPSA-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 Point25°C
Boiling PointNot Available
Solubility0.014 mg/mL at 25°C [WORTHING,CR & WALKER,SB (1983)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP3.68ALOGPS
logP3.36ChemAxon
logS-4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.4 m³·mol⁻¹ChemAxon
Polarizability27.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-1790000000-cf1cb2e692c20b2be8c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-3930000000-23107a784f899293598bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9800000000-9e2af06a3701aa16b03fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01di-0960000000-0649f3d608161e6f9efaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-1920000000-e22dfd9b4a3470bf108aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-9700000000-1b03e08d5a7318afa569JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-000f-9210000000-d04d68947e99c3684ac6JSpectraViewer | MoNA
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)3, not classifiable as to its carcinogenicity to humans. (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 EffectsDiallate is carcinogenic. 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)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5284376
ChEMBL IDCHEMBL2252931
ChemSpider ID4447452
KEGG IDC19094
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDCPD-9439
CTD IDC004755
Stitch IDDi-allate
PDB IDNot Available
ACToR ID395
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0956.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 ]