Bensulide (CHEM002758)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (31)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:50 UTC
Update Date2016-11-09 01:08:58 UTC
Accession NumberCHEM002758
Identification
Common NameBensulide
ClassSmall Molecule
DescriptionBensulide is an organophosphate acetylcholinesterase inhibitor used as an herbicide. It functions by inhibiting cell division in meristematic root tissues and seedling growth by conjugation of acetyl co-enzyme.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Ester
  • Food Toxin
  • Herbicide
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC14H24NO4PS3
Average Molecular Mass397.513 g/mol
Monoisotopic Mass397.061 g/mol
CAS Registry Number741-58-2
IUPAC NameO,O-bis(propan-2-yl) [(2-benzenesulfonamidoethyl)sulfanyl]phosphonothioate
Traditional NameO,O-diisopropyl (2-benzenesulfonamidoethyl)sulfanylphosphonothioate
SMILESCC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1
InChI IdentifierInChI=1S/C14H24NO4PS3/c1-12(2)18-20(21,19-13(3)4)22-11-10-15-23(16,17)14-8-6-5-7-9-14/h5-9,12-13,15H,10-11H2,1-4H3
InChI KeyRRNIZKPFKNDSRS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Organosulfonic acid amide
  • Dithiophosphate s-ester
  • Dithiophosphate o-ester
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Organic dithiophosphate
  • Organothiophosphorus compound
  • Sulfenyl compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP3.59ALOGPS
logP3.45ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)10.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.63 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity102.18 m³·mol⁻¹ChemAxon
Polarizability40.61 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, Positivesplash10-00ec-0912000000-3f08ecb8e633fb4e4da9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-03di-0910000000-cf9c3d235c297650921fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-03di-0900000000-954283070fd0a0712ea9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-01ot-9300000000-96c6b7a0d6a3698f6de9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-01ot-9100000000-3cca515561fb074358a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0940000000-b74978b32dca430f9e82Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0190000000-0059018d1b077771de1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-052f-1900000000-b200cc338f00ee3251c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-01r6-7900000000-0a47790cc869a8bb57a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03di-0390000000-1eb2ce4468d03d3a39a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-03di-0090000000-995c0e60aa46d24c988bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-03di-0900000000-8f450cd1bf2f598035e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-03di-0900000000-fd0362c7fba25f912786Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1693000000-b969e311084a9f912e31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2429000000-ee26e595556b5f1364f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02dl-9100000000-4005cb1abe3d23404ad7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fs-1539000000-37b65f59922364b3c72dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1932000000-5ee63e16d60ad868405aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-2983000000-4fd808b0285aac05be18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07vi-0179000000-3c1719147c746b81c722Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0693-3951000000-995fdb5f703808bb3266Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9300000000-e4a80b20a5e3a265043aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-99c0a19e2229c31a5cd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-0794000000-47b1acd7b5fe2c081ebfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-0900000000-28f527978bf789133d64Spectrum
MSMass Spectrum (Electron Ionization)splash10-00b9-9600000000-96687229c981d9fd265dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityBensulide 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/SourcesNot Available
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 IDHMDB0248962
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBensulide
Chemspider ID12397
ChEBI IDNot Available
PubChem Compound ID12932
Kegg Compound IDC18703
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.