Dimethoate (CHEM000201)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:19 UTC
Update Date2016-11-09 01:08:11 UTC
Accession NumberCHEM000201
Identification
Common NameDimethoate
ClassSmall Molecule
DescriptionDimethoate is an organophosphate insecticide used to kill mites and insects systemically and on contact. It is used against a wide range of insects, including aphids, thrips, planthoppers and whiteflies on ornamental plants, alfalfa, apples, corn, cotton, grapefruit, grapes, lemons, melons, oranges, pears, pecans, safflower, sorghum, soybeans, tangerines, tobacco, tomatoes, watermelons, wheat and other vegetables. It is also used as a residual wall spray in farm buildings for house flies. Dimethoate has been administered to livestock for control of botflies. Dimethoate is moderately toxic and severe poisoning affects the central nervous system. (1)
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Household Toxin
  • Insecticide
  • Organic Compound
  • Organophosphate
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Dimethoxyphosphinothioylthio-N-methylacetamideChEBI
O,O-Dimethyl S-[2-(methylamino)-2-oxoethyl] dithiophosphateChEBI
PhosphamideChEBI
Phosphorodithioic acid, O,O-dimethyl S-(2-(methylamino)-2-oxoethyl) esterChEBI
O,O-Dimethyl S-[2-(methylamino)-2-oxoethyl] dithiophosphoric acidGenerator
Phosphorodithioate, O,O-dimethyl S-(2-(methylamino)-2-oxoethyl) esterGenerator
Dimethoic acidGenerator
Bi 58MeSH
Bi-58MeSH
RogorMeSH
Chemical FormulaC5H12NO3PS2
Average Molecular Mass229.257 g/mol
Monoisotopic Mass229.000 g/mol
CAS Registry Number60-51-5
IUPAC NameO,O-dimethyl {[(methylcarbamoyl)methyl]sulfanyl}phosphonothioate
Traditional Namedimethoate
SMILESCNC(=O)CSP(=S)(OC)OC
InChI IdentifierInChI=1S/C5H12NO3PS2/c1-6-5(7)4-12-10(11,8-2)9-3/h4H2,1-3H3,(H,6,7)
InChI KeyMCWXGJITAZMZEV-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 s-ester
  • Dithiophosphate o-ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceDimethoate is a colorless crystalline solid with a camphor-like odor. (1)
Experimental Properties
PropertyValue
Melting Point52°C
Boiling Point117 °C (390°K) at 10 Pa
Solubility25 mg/mL at 21 °C [MARTIN,H & WORTHING,CR (1977)]
Predicted Properties
PropertyValueSource
Water Solubility2.08 g/LALOGPS
logP1.21ALOGPS
logP0.34ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)15.93ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity55.34 m³·mol⁻¹ChemAxon
Polarizability21.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0002-0910000000-ed8ec0dde52f74f3a67dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00di-0900000000-e025ead26ae3e68a1bd3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0900000000-bef9184359bd74d3b461Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-00di-0900000000-3604a83f4707c27dddf7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-00di-0900000000-cf657743456c790d9583Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 16V, positivesplash10-0002-0900000000-a403532b2a700d0bb90eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 6V, positivesplash10-0002-0920000000-d02ded0e6c91c275f535Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 13V, positivesplash10-00di-0900000000-dc425cd39054cc7d80baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 20V, positivesplash10-00dl-0900000000-6eae390613eea97ecbd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 27V, positivesplash10-00dl-1900000000-2f6bff3bd95d96c32e1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 34V, positivesplash10-006x-2900000000-0ee34ba6c3832a6b2d91Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 41V, positivesplash10-006x-4900000000-bf8f93d91440e270a87cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 25V, positivesplash10-00di-0900000000-76eec21ed353331cbc72Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 36V, positivesplash10-00dl-2900000000-9c36234a485bc6baec04Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 16V, positivesplash10-0002-0900000000-92b5ec6da125b0d970a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00di-2900000000-efcc4129b0b2ce499949Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 16V, positivesplash10-006y-1900000000-a64e8fc263dddfcc8028Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00dl-0900000000-d43550cbd5a4aecf2907Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0udi-0390000000-612adcf5756794a5816aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-2920000000-008d4aec36ec4daa873aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-5940000000-cac4e89879d5ca21a230Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-f5ef08d5b522ad4f8406Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056s-0970000000-7ecf0622179fb1cab244Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0731-1930000000-e6b9b176d6f431c404a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-2900000000-565c86ecd4f189da1096Spectrum
MSMass Spectrum (Electron Ionization)splash10-002u-9200000000-cf18e41a937e5d76b828Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityDimethoate 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.
MetabolismMetabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Toxicity ValuesLD50: 60 to 387 mg/kg (Oral, Rat) LD50: 60 mg/kg (Oral, Mouse) LD50: 400 mg/kg (Oral, Dog) LD50: 200 mg/kg (Oral, Hamster) LD50: 300 mg/kg (Oral, Rabbit) LD50: 350 mg/kg (Oral, Guinea pig) LD50: 100 mg/kg (Oral, Cat) LD50: 1000 mg/kg (Dermal, Rabbit) LD50: 353 mg/kg (Dermal, Rat) LC50: 1.2 mg/l (Rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (2)
Uses/SourcesDimethoate is an organophosphate insecticide used to kill mites and insects systemically and on contact. It is used against a wide range of insects, including aphids, thrips, planthoppers and whiteflies on ornamental plants, alfalfa, apples, corn, cotton, grapefruit, grapes, lemons, melons, oranges, pears, pecans, safflower, sorghum, soybeans, tangerines, tobacco, tomatoes, watermelons, wheat and other vegetables. It is also used as a residual wall spray in farm buildings for house flies. Dimethoate has been administered to livestock for control of botflies. (1)
Minimum Risk LevelNot Available
Health EffectsAcute 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. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
SymptomsThe first symptoms include bloody or runny nose, coughing, chest discomfort, difficult or short breath, and wheezing due to constriction or excess fluid in the bronchial tubes. Skin contact may cause localized sweating and involuntary muscle contractions. Eye contact will cause pain, bleeding, tears, pupil constriction, and blurred vision. Other symptoms following any way of exposure may include pallor, nausea, vomiting, diarrhea, abdominal cramps, headache, dizziness, eye pain, blurred vision, constriction or dilation of the eye pupils, tears, salivation, sweating, and confusion. Severe poisoning will affect the central nervous system, producing incoordination, slurred speech, loss of reflexes, weakness, fatigue, involuntary muscle contractions, twitching, tremors of the tongue or eyelids, and eventually paralysis of the body extremities and the respiratory muscles. In severe cases there may also be involuntary defecation or urination, psychosis, irregular heart beats, unconsciousness, convulsions and coma. Death may be caused by respiratory failure or cardiac arrest. (1)
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.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0251379
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDimethoate
Chemspider ID2973
ChEBI ID34714
PubChem Compound ID3082
Kegg Compound IDC14326
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11054639
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15803959