Basic Info

Common NameCarbosulfan(F03977)
2D Structure
Description

Carbosulfan is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795)

FRCD IDF03977
CAS Number55285-14-8
PubChem CID41384
FormulaC20H32N2O3S
IUPAC Name

(2,2-dimethyl-3H-1-benzofuran-7-yl) N-(dibutylamino)sulfanyl-N-methylcarbamate

InChI Key

JLQUFIHWVLZVTJ-UHFFFAOYSA-N

InChI

InChI=1S/C20H32N2O3S/c1-6-8-13-22(14-9-7-2)26-21(5)19(23)24-17-12-10-11-16-15-20(3,4)25-18(16)17/h10-12H,6-9,13-15H2,1-5H3

Canonical SMILES

CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C

Isomeric SMILES

CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C

Synonyms
        
            Dibutylaminosulfenylcarbofuran
        
            Carbosulfan
        
            Marshal
        
            55285-14-8
        
            Posse
        
            Advantage
        
            Marshall
        
            Caswell No. 463C
        
            FMC 35001
        
            UNII-V1DGN4AK6G
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassCoumarans
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentCoumarans
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsCoumaran - Alkyl aryl ether - Benzenoid - Carbonic acid derivative - Oxacycle - Ether - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as coumarans. These are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Properties

Property NameProperty Value
Molecular Weight380.547
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count10
Complexity439
Monoisotopic Mass380.213
Exact Mass380.213
XLogP5.7
Formal Charge0
Heavy Atom Count26
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9413
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2-0.5338
P-glycoprotein SubstrateSubstrate0.7381
P-glycoprotein InhibitorInhibitor0.6047
Non-inhibitor0.9409
Renal Organic Cation TransporterNon-inhibitor0.7810
Distribution
Subcellular localizationMitochondria0.5151
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6020
CYP450 2D6 SubstrateNon-substrate0.7408
CYP450 3A4 SubstrateSubstrate0.6885
CYP450 1A2 InhibitorNon-inhibitor0.6945
CYP450 2C9 InhibitorNon-inhibitor0.6559
CYP450 2D6 InhibitorNon-inhibitor0.7970
CYP450 2C19 InhibitorNon-inhibitor0.5794
CYP450 3A4 InhibitorNon-inhibitor0.8879
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6884
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8673
Non-inhibitor0.6665
AMES ToxicityNon AMES toxic0.6210
CarcinogensNon-carcinogens0.7615
Fish ToxicityHigh FHMT0.9963
Tetrahymena Pyriformis ToxicityHigh TPT0.9807
Honey Bee ToxicityHigh HBT0.6269
BiodegradationNot ready biodegradable0.9934
Acute Oral ToxicityII0.7172
Carcinogenicity (Three-class)Non-required0.6052

Model Value Unit
Absorption
Aqueous solubility-4.2568LogS
Caco-2 Permeability1.3081LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.8415LD50, mol/kg
Fish Toxicity1.0138pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6714pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MitsubaJapan1ppm
CeleryJapan1ppm
ParsleyJapan1ppm
ParsnipJapan1ppm
CarrotJapan1ppm
HuckleberryJapan0.2ppm
CranberryJapan0.2ppm
BlueberryJapan0.2ppm
BlackberryJapan0.2ppm
RaspberryJapan0.2ppm
CherryJapan0.2ppm
Mume PlumJapan0.2ppm
Milk & Dairy ProduceBritain0.05mg/kg
Meat, Fat & Preparations Of MeatBritain0.05mg/kg
Other Cereals Do Not Include RiceBritain0.05mg/kg
RiceBritain0.05mg/kg
MilletBritain0.05mg/kg
BuckwheatBritain0.05mg/kg
MaizeBritain0.05mg/kg
TriticaleBritain0.05mg/kg

References

TitleJournalDatePubmed ID
Residue behavior and dietary intake risk assessment of carbosulfan and its metabolites in cucumber.Regul Toxicol Pharmacol2018 Jun29601912
Self-Reported Symptoms and Pesticide Use among Farm Workers in Arusha, NorthernTanzania: A Cross Sectional Study.Toxics2017 Sep 2729051456
Electrochemical acetylcholinesterase biosensor based on ZnO nanocuboids modified platinum electrode for the detection of carbosulfan in rice.Biosens Bioelectron2016 Mar 1526562329
A comparative study on toxicity induced by carbosulfan and malathion in Wistar rat liver and spleen.Pestic Biochem Physiol2015 Oct26453226
Mutagenic and genotoxic effects of carbosulfan in freshwater fish Channapunctatus (Bloch) using micronucleus assay and alkaline single-cell gelelectrophoresis.Food Chem Toxicol2010 Jan19818828
Persistence and nematicidal efficacy of carbosulfan, cadusafos, phorate, andtriazophos in soil and uptake by chickpea and tomato crops under tropicalconditions.J Agric Food Chem2010 Feb 1020085277
Determination of pesticide residues in integrated pest management andnonintegrated pest management samples of apple (Malus pumila Mill.).J Agric Food Chem2009 Dec 919904932
Liquid chromatography quadrupole time-of-flight mass spectrometry analysis ofcarbosulfan, carbofuran, 3-hydroxycarbofuran, and other metabolites in food.Anal Chem2007 Feb 1517241092
[Behavior of N-methylcarbamate pesticides during refinement processing of edible oils].J Oleo Sci200717898465
An approach for IPM program to control sucking pests infesting garden bean plants(Phaseolus vulgaris L.) in Egypt.Commun Agric Appl Biol Sci200718399490
Supercritical fluid extraction of the pesticides carbosulfan and imidaclopridfrom process dust waste.J Agric Food Chem2000 Nov11087452

Targets

General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
Mechanism of Action:
Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]