Endosulfan

Basic Info

Common NameEndosulfan(F06190)
2D Structure
FRCD IDF06190
CAS Number115-29-7
PubChem CID3224
FormulaC9H6Cl6O3S
IUPAC Name

None

InChI Key

RDYMFSUJUZBWLH-UHFFFAOYSA-N

InChI

InChI=1S/C9H6Cl6O3S/c10-5-6(11)8(13)4-2-18-19(16)17-1-3(4)7(5,12)9(8,14)15/h3-4H,1-2H2

Canonical SMILES

C1C2C(COS(=O)O1)C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl

Isomeric SMILES

C1C2C(COS(=O)O1)C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl

Synonyms
        
            endosulfan
        
            Chlorthiepin
        
            Benzoepin
        
            Thiodan
        
            Thiosulfan
        
            Thionex
        
            115-29-7
        
            Insectophene
        
            Rasayansulfan
        
            Devisulphan
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
SubclassOrganic sulfites
Intermediate Tree NodesNot available
Direct ParentSulfite esters
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsSulfite ester - Oxacycle - Chloroalkene - Haloalkene - Organoheterocyclic compound - Vinyl halide - Vinyl chloride - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Alkyl halide - Alkyl chloride - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as sulfite esters. These are organic compounds containing an organic group attached to the sulfite oxoanion, with the formula R[SO3]2-.

Properties

Property NameProperty Value
Molecular Weight406.904
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Complexity470
Monoisotopic Mass403.817
Exact Mass405.814
XLogP3.8
Formal Charge0
Heavy Atom Count19
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count4
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9256
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2-0.5793
P-glycoprotein SubstrateNon-substrate0.6946
P-glycoprotein InhibitorInhibitor0.8105
Non-inhibitor0.9949
Renal Organic Cation TransporterNon-inhibitor0.8557
Distribution
Subcellular localizationLysosome0.5538
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8783
CYP450 2D6 SubstrateNon-substrate0.8042
CYP450 3A4 SubstrateNon-substrate0.5248
CYP450 1A2 InhibitorNon-inhibitor0.6378
CYP450 2C9 InhibitorNon-inhibitor0.7094
CYP450 2D6 InhibitorNon-inhibitor0.8671
CYP450 2C19 InhibitorNon-inhibitor0.6227
CYP450 3A4 InhibitorNon-inhibitor0.8427
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6910
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.6088
Non-inhibitor0.8324
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.5340
Fish ToxicityHigh FHMT0.9602
Tetrahymena Pyriformis ToxicityHigh TPT0.9467
Honey Bee ToxicityHigh HBT0.8934
BiodegradationNot ready biodegradable0.9939
Acute Oral ToxicityII0.7668
Carcinogenicity (Three-class)Non-required0.4696
Model Value Unit
Absorption
Aqueous solubility-4.0206LogS
Caco-2 Permeability0.9106LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.5104LD50, mol/kg
Fish Toxicity1.3309pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5895pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Beans,DryJapan1ppm
AvocadosKorea1ppm
PapayaKorea1ppm
TomatoKorea0.5ppm
CabbageKorea1ppm
PeanutsBritain0.1mg/kg
Leaves & Stems Of BrassicaBritain0.05mg/kg
Milk & Dairy ProduceBritain0.004mg/kg
All Meat Except PoultrymeatBritain0.1mg/kg
HopBritain0.1mg/kg
TeaBritain30mg/kg
Ware PotatoesBritain0.05mg/kg
Early PotatoesBritain0.05mg/kg
Other OilseedsBritain0.1mg/kg
Hemp SeedBritain0.1mg/kg
Cotton SeedBritain5mg/kg
Mustard SeedBritain0.1mg/kg
Soya BeanBritain0. 5mg/kg
Rape SeedBritain0.1mg/kg
Sunflower SeedBritain0.1mg/kg

References

TitleJournalDatePubmed ID
Persistent organochlorine pesticides in aquatic environments and fishes in Taiwan and their risk assessment.Environ Sci Pollut Res Int2018 Mar29288298
Solvent effect on endosulfan adsorption onto polymeric arginine-methacrylatecryogels.Environ Sci Pollut Res Int2018 Jun 2729951763
Serum concentrations of organochlorine compounds and predictors of exposure inchildren living in agricultural communities from South-Eastern Spain.Environ Pollut2018 Jun29129429
The effects of imidacloprid combined with endosulfan on IgE-mediated mouse bonemarrow-derived mast cell degranulation and anaphylaxis.Pestic Biochem Physiol2018 Jun29891367
Development and Validation of a Method for the Detection of α- and β-Endosulfan(Organochlorine Insecticide) in Calliphora vomitoria (Diptera: Calliphoridae).J Med Entomol2018 Jan 1029029268
Discrepant effects of α-endosulfan, β-endosulfan, and endosulfan sulfate onoxidative stress and energy metabolism in the livers and kidneys of mice.Chemosphere2018 Aug29702342
Pesticide genotoxicity in cotton picking women in Pakistan evaluated using comet assay.Drug Chem Toxicol2018 Apr28721745
Genome-wide gene expression changes associated with exposure of rat liver, heart,and kidney cells to endosulfan.Toxicol In Vitro2018 Apr29391264
Self-Reported Symptoms and Pesticide Use among Farm Workers in Arusha, NorthernTanzania: A Cross Sectional Study.Toxics2017 Sep 2729051456
Organochlorine pesticide concentrations in pooled serum of people in differentage groups from five Chinese cities.Sci Total Environ2017 May 1528238380
Lower levels of Persistent Organic Pollutants, metals and the marine omega3-fatty acid DHA in farmed compared to wild Atlantic salmon (Salmo salar).Environ Res2017 May28189073
Residues of organochlorine pesticides in surface soil and raw foods from ruralareas of the Republic of Tajikistan.Environ Pollut2017 May28237311
Determination of the priority substances regulated by 2000/60/EC and 2008/105/EC Directives in the surface waters supplying water treatment plants of Athens, Greece.J Environ Sci Health A Tox Hazard Subst Environ Eng2017 Mar 2127973987
Vitamin E reduces endosulfan-induced toxic effects on morphology and behavior in early development of zebrafish (Danio rerio).Food Chem Toxicol2017 Mar28065758
Presence of pesticide residues on produce cultivated in Suriname.Environ Monit Assess2017 Jun28567597
Extraction of Organochlorine Pesticides from Plastic Pellets and Plastic Type Analysis.J Vis Exp2017 Jul 128715401
Status of pesticides pollution in Tanzania - A review.Chemosphere2017 Jul28324837
Sex-dependent effects of developmental exposure to different pesticides onspatial learning. The role of induced neuroinflammation in the hippocampus.Food Chem Toxicol2017 Jan27908700
Levels of persistent organic pollutants in breast milk of Maya women in Yucatan, Mexico.Environ Monit Assess2017 Feb28091886
Pesticide incidence in poisoned baits: A 10-year report.Sci Total Environ2017 Dec 128564626