Tebupirimfos (CHEM002888)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:54 UTC
Update Date2016-11-09 01:08:59 UTC
Accession NumberCHEM002888
Identification
Common NameTebupirimfos
ClassSmall Molecule
DescriptionTebupirimfos, also known as phostebupirim, is an organothiophosphate insecticide. It is used on corn crops, including popcorn.
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Insecticide
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
O-(2-(1,1-Dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) phosphorothioateChEBI
O-(2-Tert-butylpyrimidin-5-yl) O-ethyl O-isopropyl thiophosphateChEBI
Phosphorothioic acid, O-(2-(1,1-dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) esterChEBI
PhostebupirimChEBI
TebupirimphosChEBI
O-(2-(1,1-Dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) phosphorothioic acidGenerator
O-(2-Tert-butylpyrimidin-5-yl) O-ethyl O-isopropyl thiophosphoric acidGenerator
Phosphorothioate, O-(2-(1,1-dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) esterGenerator
Chemical FormulaC13H23N2O3PS
Average Molecular Mass318.372 g/mol
Monoisotopic Mass318.117 g/mol
CAS Registry Number96182-53-5
IUPAC NameO-2-tert-butylpyrimidin-5-yl O-ethyl O-propan-2-yl phosphorothioate
Traditional NameO-2-tert-butylpyrimidin-5-yl O-ethyl O-isopropyl phosphorothioate
SMILESCCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C
InChI IdentifierInChI=1S/C13H23N2O3PS/c1-7-16-19(20,17-10(2)3)18-11-8-14-12(15-9-11)13(4,5)6/h8-10H,7H2,1-6H3
InChI KeyAWYOMXWDGWUJHS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentPyrimidinyl phosphorothioates
Alternative Parents
Substituents
  • Pyrimidinyl phosphorothioate
  • Thiophosphate triester
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP4.4ALOGPS
logP4.37ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)0.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.47 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity84.77 m³·mol⁻¹ChemAxon
Polarizability33.21 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0kbb-3091000000-e482925bb6fcfc44353fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0udi-0950000000-69f7d979b099897396c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0udi-0910000000-38add9d4c6dc3c9b1dcbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0290000000-176b5e76ef68801d2300Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-00or-0095000000-91a7dde839fb7669e005Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0udi-2900000000-3f567a576a7d1fa8d3d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0zg0-5900000000-4c3cc7498ae0d242ad51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1291000000-4d0dc62832ebcc780ce4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1290000000-9368f2f9b8099edef4a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059l-9800000000-381851a99cde0191b3f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00n0-0392000000-57fcec897ede61056ac4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0290000000-9cc36c0cae92a541c630Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3390000000-f5cdaf73ae60de86fbf3Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityTebupirimfos 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 ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as a pesticide.
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.
SymptomsSymptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include 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. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.
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 IDHMDB0258766
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTebupirimfos
Chemspider ID84419
ChEBI ID38951
PubChem Compound IDNot Available
Kegg Compound IDC18692
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available