Carbofuran

Basic Info

Common NameCarbofuran(F03976)
2D Structure
Description

Carbofuran is a carbamate pesticide. It is used as systemic agricultural insecticide, acaricide and nematocide. Carbofuran has been shown to exhibit neuroprotectant and neuroprotective functions (A7790, A7790). Carbofuran belongs to the family of Benzofurans. These are organic compounds containing a benzene ring fused to a furan.

FRCD IDF03976
CAS Number1563-66-2
PubChem CID2566
FormulaC12H15NO3
IUPAC Name

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

InChI Key

DUEPRVBVGDRKAG-UHFFFAOYSA-N

InChI

InChI=1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)

Canonical SMILES

CC1(CC2=C(O1)C(=CC=C2)OC(=O)NC)C

Isomeric SMILES

CC1(CC2=C(O1)C(=CC=C2)OC(=O)NC)C

Synonyms
        
            carbofuran
        
            Furadan
        
            1563-66-2
        
            Curaterr
        
            Yaltox
        
            Chinufur
        
            Crisfuran
        
            Furacarb
        
            Furadan 3G
        
            Furadan G
Classifies
                

                  
                    Pollutant
                  
                    Illegal Additives
                  
                    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 - Carboximidic acid derivative - Ether - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Oxacycle - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Imine - Hydrocarbon derivative - Organopnictogen compound - 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 Weight221.256
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Complexity277
Monoisotopic Mass221.105
Exact Mass221.105
XLogP2.3
Formal Charge0
Heavy Atom Count16
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+0.9287
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5452
P-glycoprotein SubstrateNon-substrate0.6608
P-glycoprotein InhibitorNon-inhibitor0.6724
Non-inhibitor0.8431
Renal Organic Cation TransporterNon-inhibitor0.9366
Distribution
Subcellular localizationMitochondria0.4656
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7571
CYP450 2D6 SubstrateNon-substrate0.6644
CYP450 3A4 SubstrateSubstrate0.6748
CYP450 1A2 InhibitorInhibitor0.5843
CYP450 2C9 InhibitorNon-inhibitor0.7181
CYP450 2D6 InhibitorNon-inhibitor0.8489
CYP450 2C19 InhibitorNon-inhibitor0.7218
CYP450 3A4 InhibitorNon-inhibitor0.8667
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5591
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9919
Non-inhibitor0.9567
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.8957
Fish ToxicityHigh FHMT0.8519
Tetrahymena Pyriformis ToxicityHigh TPT0.9738
Honey Bee ToxicityHigh HBT0.8501
BiodegradationNot ready biodegradable0.9770
Acute Oral ToxicityI0.7862
Carcinogenicity (Three-class)Non-required0.4922
Model Value Unit
Absorption
Aqueous solubility-2.8626LogS
Caco-2 Permeability1.3092LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.3377LD50, mol/kg
Fish Toxicity0.0513pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6299pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
WatercressJapan0.5ppm
HorseradishJapan0.5ppm
CEREALS0500000European Union0.01*03/10/2015
Guavas (Brazilian guavas, Cattley guavas, Costarican guavas, Guayabillos, Parà guavas,)0163070European Union0.01*03/10/2015
Pineapples0163080European Union0.01*03/10/2015
Brussels sprouts (Flower sprouts,)0242010European Union0.002*03/10/2015
Citrus fruits0110000European Union0.01*03/10/2015
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*03/10/2015
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*03/10/2015
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*03/10/2015
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*03/10/2015
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*03/10/2015
Others (2)0110990European Union0.01*03/10/2015
Tree nuts0120000European Union0.02*03/10/2015
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*03/10/2015
Brazil nuts0120020European Union0.02*03/10/2015
Cashew nuts0120030European Union0.02*03/10/2015
Chestnuts0120040European Union0.02*03/10/2015
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*03/10/2015
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*03/10/2015

References

TitleJournalDatePubmed ID
Coating polystyrene beads with iron oxide for the adsorption of carbofuran fromthe water supply.Environ Technol2018 Mar 29:1-729561709
Residue behavior and dietary intake risk assessment of carbosulfan and its metabolites in cucumber.Regul Toxicol Pharmacol2018 Jun29601912
Animal mortality and illegal poison bait use in Greece.Environ Monit Assess2018 Jul 2530046915
Nano carbon black-based screen printed sensor for carbofuran, isoprocarb,carbaryl and fenobucarb detection: application to grain samples.Talanta2018 Aug 1529784378
<i>Ganoderma lucidum</i> and <i>Auricularia polytricha</i> Mushrooms Protect against Carbofuran-Induced Toxicity in Rats.Evid Based Complement Alternat Med201829861774
[Rapid screening and identification of food poisonings by ultra high performance liquid chromatography coupled with quadrupole-time of flight mass spectrometry].Se Pu2017 Sep 829048853
A double-label time-resolved fluorescent strip for rapidly quantitative detectionof carbofuran residues in agro-products.Food Chem2017 Sep 1528450009
Determination of a broad spectrum of endocrine-disrupting pesticides in fishsamples by UHPLC-MS/MS using the pass-through cleanup approach.J Sep Sci2017 Mar28098419
[Combined cytotoxicity mechanism of chlorpyrifos and carbofuran pesticides invitro].Wei Sheng Yan Jiu2017 Jul29903186
Validation and assessment of matrix effect and uncertainty of a gaschromatography coupled to mass spectrometry method for pesticides in papaya andavocado samples.J Food Drug Anal2017 Jul28911635
Trace determination of carbamate pesticides in medicinal plants by a fluorescent technique.Food Chem Toxicol2017 Dec 1829269059
Pesticide incidence in poisoned baits: A 10-year report.Sci Total Environ2017 Dec 128564626
Voltammetric detection of carbofuran determination using screen-printed carbon electrodes modified with gold nanoparticles and graphene oxide.Talanta2017 Dec 128841999
Dietary risk assessment of pesticides from vegetables and drinking water ingardening areas in Burkina Faso.Sci Total Environ2017 Dec 128605838
Protective mechanism of turmeric (Curcuma longa) on carbofuran-inducedhematological and hepatic toxicities in a rat model.Pharm Biol2017 Dec28675957
Highly sensitive microcantilever-based immunosensor for the detection ofcarbofuran in soil and vegetable samples.Food Chem2017 Aug 1528372196
Comprehensive estimate of the theoretical maximum daily intake of pesticideresidues for chronic dietary risk assessment in Argentina.J Environ Sci Health B2017 Apr 328085552
Facile and Sensitive Detection of Carbofuran Carbamate Pesticide in Rice and Soybean Using Coupling Reaction-based Surface-Enhanced Raman Scattering.Anal Sci201728070083
Multi-residue detection of pesticides using a sensitive immunochip assay based onnanogold enhancement.Anal Chim Acta2016 Sep 2827619097
Ecological risk analysis of pesticides used on irrigated rice crops in southernBrazil.Chemosphere2016 Nov27479455

Targets

Target Details

Cholinesterase

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
Target Details

Acetylcholinesterase

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 ]