Fenitrothion (CHEM002800)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (16)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:51 UTC
Update Date2016-11-09 01:08:58 UTC
Accession NumberCHEM002800
Identification
Common NameFenitrothion
ClassSmall Molecule
DescriptionFenitrothion is an organophospahate insecticide that has been used since 1959 to control insects on rice, cereals, fruits, vegetables, stored grains, cotton, to control insects in forests and for fly, mosquito, and cockroach control in public health programs. Between 15 000 and 20 000 tons of fenitrothion are produced per year. The health effects of finitrothion are consistent with those of other organophosphates and are the result of cholinesterase inhibition.
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Insecticide
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MEPChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioateChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) thiophosphateChEBI
O,O-Dimethyl O-4-nitro-m-tolyl phosphorothioateChEBI
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioic acidGenerator
O,O-Dimethyl O-(3-methyl-4-nitrophenyl) thiophosphoric acidGenerator
O,O-Dimethyl O-4-nitro-m-tolyl phosphorothioic acidGenerator
AccothionHMDB
AceothionHMDB
Agriya 1050HMDB
AgrothionHMDB
AkotionHMDB
American cyanamid CL-47,300HMDB
ArbogalHMDB
Bayer S 5660HMDB
Bis-fenitrothionHMDB
CekutrothionHMDB
CyfenHMDB
CytelHMDB
CytenHMDB
DicofenHMDB
Dimethyl 3-methyl-4-nitrophenyl phosphorothionateHMDB
Dimethyl 4-nitro-m-tolyl phosphorothionateHMDB
FalithionHMDB
FenitoxHMDB
FenitrotionHMDB
FolithionHMDB
Folithion ec 50HMDB
KotionHMDB
MacbarHMDB
MEP (pesticide)HMDB
MEP (phosphorus insecticide)HMDB
Metathio e-50HMDB
MetathionHMDB
Metathion e-50HMDB
MetathioneHMDB
MetathionineHMDB
Metathionine e-50HMDB
MetationHMDB
Metation e-50HMDB
MethylnitrophosHMDB
Mglawik FHMDB
NitrophosHMDB
NovathionHMDB
NuvanolHMDB
O,O-DiMe O-(3-methyl-4-nitrophenyl) thiophosphateHMDB
O,O-Dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioateHMDB
O,O-Dimethyl O-(4-nitro-3-methylphenyl)thiophosphateHMDB
O,O-Dimethyl O-4-nitro-m-tolyl thiophosphateHMDB
O,O-Dimethyl-O-(3-methyl-4-nitro-phenyl)-monothiophosphateHMDB
O,O-Dimethyl-O-(3-methyl-4-nitrofenyl)-monothiofosfaatHMDB
O,O-Dimethyl-O-(4-nitro-5-methylphenyl)-thionophosphateHMDB
O,O-Dimetil-O-(3-metil-4-nitro-fenil)-monotiofosfatoHMDB
O,O-Dimetil-O-(3-metil-4-nitrofenil) fosforotioatoHMDB
OleometathionHMDB
OleosumifeneHMDB
OvadofosHMDB
OwadofosHMDB
OwadophosHMDB
Pennwalt C-4852HMDB
PhenitrothionHMDB
SumifeneHMDB
SumigranHMDB
SumithianHMDB
SumithionHMDB
Sumitomo S-1102aHMDB
Tionfos 50 leHMDB
VerthionHMDB
1050, AgriaHMDB
Agria 1050HMDB
SumithioneHMDB
Chemical FormulaC9H12NO5PS
Average Molecular Mass277.234 g/mol
Monoisotopic Mass277.017 g/mol
CAS Registry Number122-14-5
IUPAC NameO,O-dimethyl O-3-methyl-4-nitrophenyl phosphorothioate
Traditional NameO,O-dimethyl O-3-methyl-4-nitrophenyl phosphorothioate
SMILESCOP(=S)(OC)OC1=CC=C(C(C)=C1)N(=O)=O
InChI IdentifierInChI=1S/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3
InChI KeyZNOLGFHPUIJIMJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentPhenyl thiophosphates
Alternative Parents
Substituents
  • Phenyl thiophosphate
  • Nitrobenzene
  • Nitrotoluene
  • Phenoxy compound
  • Nitroaromatic compound
  • Thiophosphate triester
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point3.4°C
Boiling PointNot Available
Solubility0.038 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP3.31ALOGPS
logP3.12ChemAxon
logS-4.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area73.51 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.23 m³·mol⁻¹ChemAxon
Polarizability24.74 ųChemAxon
Number of Rings1ChemAxon
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)splash10-01tc-9540000000-a180b7cec61770691237Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1980000000-469fd8d8b5afef55db6dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01tc-9540000000-a180b7cec61770691237Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1980000000-469fd8d8b5afef55db6dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-3950000000-0b6ab147cddeb288eed5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-2848423a70610d0dae28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0090000000-d10a1515515bbdc69975Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-3940000000-5cc3638b33f222c4352cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0390000000-e49f20ded24e19945287Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0490000000-c57ad69bf50c72792ac7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1900000000-d97d44855ea21933b936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-15d4b7303fe1f263e6e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-15d4b7303fe1f263e6e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9380000000-15ab04f4c83619b667beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-4047b7defcfd38181f33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0390000000-106366d9a50461b52a49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-8910000000-5b5ac2d7434bed2a6cd8Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-8980000000-4c5af1b2fb42bdb10504Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityFenitrothion 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 IDHMDB0041893
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFenitrothion
Chemspider ID28941
ChEBI ID34757
PubChem Compound ID31200
Kegg Compound IDC14442
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11201171
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16628916
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23668748