Decarbofuran

Basic Info

Common NameDecarbofuran(F03985)
2D Structure
Description

Decarbofuran 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 IDF03985
CAS Number1563-67-3
PubChem CID15279
FormulaC11H13NO3
IUPAC Name

(2-methyl-2,3-dihydro-1-benzofuran-7-yl) N-methylcarbamate

InChI Key

JTBBRGSSVACAJM-UHFFFAOYSA-N

InChI

InChI=1S/C11H13NO3/c1-7-6-8-4-3-5-9(10(8)14-7)15-11(13)12-2/h3-5,7H,6H2,1-2H3,(H,12,13)

Canonical SMILES

CC1CC2=C(O1)C(=CC=C2)OC(=O)NC

Isomeric SMILES

CC1CC2=C(O1)C(=CC=C2)OC(=O)NC

Synonyms
        
            ENT 27,324
        
            Decarbofuran
        
            1563-67-3
        
            Decarbofuran [ISO]
        
            Bayer 62863
        
            OMS-1094
        
            BAY 48130
        
            BAY 62863
        
            AI3-27324
        
            A 468
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 - Carbamic acid ester - Carbonic acid derivative - Oxacycle - Ether - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - 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 Weight207.229
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Complexity244
Monoisotopic Mass207.09
Exact Mass207.09
XLogP2.1
Formal Charge0
Heavy Atom Count15
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9680
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5991
P-glycoprotein SubstrateNon-substrate0.7498
P-glycoprotein InhibitorNon-inhibitor0.8129
Non-inhibitor0.8516
Renal Organic Cation TransporterNon-inhibitor0.9221
Distribution
Subcellular localizationMitochondria0.4362
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7669
CYP450 2D6 SubstrateNon-substrate0.5707
CYP450 3A4 SubstrateSubstrate0.5702
CYP450 1A2 InhibitorInhibitor0.7690
CYP450 2C9 InhibitorNon-inhibitor0.8642
CYP450 2D6 InhibitorNon-inhibitor0.8684
CYP450 2C19 InhibitorNon-inhibitor0.8519
CYP450 3A4 InhibitorNon-inhibitor0.9283
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6622
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9766
Non-inhibitor0.9585
AMES ToxicityNon AMES toxic0.6144
CarcinogensNon-carcinogens0.9395
Fish ToxicityHigh FHMT0.7929
Tetrahymena Pyriformis ToxicityHigh TPT0.9714
Honey Bee ToxicityHigh HBT0.8011
BiodegradationNot ready biodegradable0.7944
Acute Oral ToxicityI0.7887
Carcinogenicity (Three-class)Non-required0.4895
Model Value Unit
Absorption
Aqueous solubility-2.0563LogS
Caco-2 Permeability1.2323LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.7145LD50, mol/kg
Fish Toxicity0.5508pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2056pIGC50, ug/L

Targets

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. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
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