Phosalone (CHEM002862)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (21)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2016-11-09 01:08:59 UTC
Accession NumberCHEM002862
Identification
Common NamePhosalone
ClassSmall Molecule
DescriptionPhosalone is an organophosphate chemical commonly used as an insecticide and acaricide. It is developed by Rhône-Poulenc in France but EU eliminated it from pesticide registration on December 2006.
Contaminant Sources
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Carbamate
  • Ester
  • Insecticide
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-[O,O-(Diethyldithiophosphoryl)methyl]-6-chlorobenzoxazolinoneChEBI
Agria 1060 aChEBI
Phosphorodithioic acid, S-((6-chloro-2-oxo-3(2H)-benzoxazolyl)methyl) O,O-diethyl esterChEBI
S-[(6-Chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)methyl] O,O-diethyl dithiophosphateChEBI
Phosphorodithioate, S-((6-chloro-2-oxo-3(2H)-benzoxazolyl)methyl) O,O-diethyl esterGenerator
S-[(6-Chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)methyl] O,O-diethyl dithiophosphoric acidGenerator
AzofeneHMDB
BenzophosphateHMDB
FosalonHMDB
FosaloneHMDB
FozalonHMDB
PhasolonHMDB
PhosalonHMDB
PhozalonHMDB
RubitoxHMDB
S-[(6-Chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)methyl] O,O-diethyl phosphorodithioateHMDB
ZoloneHMDB
Zolone PMHMDB
ZoolonHMDB
FozaloneHMDB
PhoazloneHMDB
PhozaloneHMDB
Chemical FormulaC12H15ClNO4PS2
Average Molecular Mass367.809 g/mol
Monoisotopic Mass366.987 g/mol
CAS Registry Number2310-17-0
IUPAC NameO,O-diethyl {[(6-chloro-2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl)methyl]sulfanyl}phosphonothioate
Traditional Namephosalone
SMILESCCOP(=S)(OCC)SCN1C(=O)OC2=C1C=CC(Cl)=C2
InChI IdentifierInChI=1S/C12H15ClNO4PS2/c1-3-16-19(20,17-4-2)21-8-14-10-6-5-9(13)7-11(10)18-12(14)15/h5-7H,3-4,8H2,1-2H3
InChI KeyIOUNQDKNJZEDEP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazoles
Sub ClassBenzoxazolones
Direct ParentBenzoxazolones
Alternative Parents
Substituents
  • Benzoxazolone
  • Aryl chloride
  • Aryl halide
  • Dithiophosphate o-ester
  • Dithiophosphate s-ester
  • Benzenoid
  • Azole
  • Oxazole
  • Heteroaromatic compound
  • Organic dithiophosphate
  • Organothiophosphorus compound
  • Sulfenyl compound
  • Oxacycle
  • Azacycle
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point46°C
Boiling PointNot Available
Solubility0.00305 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP3.96ALOGPS
logP3.75ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.24 m³·mol⁻¹ChemAxon
Polarizability35.02 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-3901000000-80a2a63054e8b0fc3477Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-3901000000-80a2a63054e8b0fc3477Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-1907000000-47d821da4a8328facc68Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0aor-9100000000-206bc8b2783f3f3c660bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01qa-9600000000-b57d5aaf11dcb79c0858Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-1903000000-e8ce8cf35e03b1822842Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01qa-9600000000-f5040fecc14bae872dc9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-067i-9200000000-04f05ba8b1a130a8e632Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-067j-9300000000-7c42db87eca9af7d5af4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-067i-9200000000-17020a34c60786caa0dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0aor-9100000000-e80fc69b9148803c6b88Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0aor-9200000000-206bc8b2783f3f3c660bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0191000000-7bddd5607e4d88fd13f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi9-0901000000-77a74f9f40bfc6df4e35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0910000000-c2ed59c980525dd525b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0749000000-eaccb0c5acac66311305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0895000000-21b8f9d07e2d377303c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0391000000-3b3070354a73b33d5a33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-c358770cc9299e9a7e03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-4baf6635b8db64ffca13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h40-0900000000-9aa4ff0cbbe935b3ff75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0911000000-4bf78aa6a97c7cbdf9b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-ff96605f966d88ef5551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00yi-2910000000-3fcdef2bb99fac3a8b03Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-5900000000-1b880221f417da6800b1Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityPhosalone 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 IDHMDB0041985
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhosalone
Chemspider ID4629
ChEBI ID8121
PubChem Compound ID4793
Kegg Compound IDC11028
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15132335
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24053362