Benfuracarb

Basic Info

Common NameBenfuracarb(F03961)
2D Structure
Description

Benfuracarb 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 IDF03961
CAS Number82560-54-1
PubChem CID54886
FormulaC20H30N2O5S
IUPAC Name

ethyl 3-[[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-propan-2-ylamino]propanoate

InChI Key

FYZBOYWSHKHDMT-UHFFFAOYSA-N

InChI

InChI=1S/C20H30N2O5S/c1-7-25-17(23)11-12-22(14(2)3)28-21(6)19(24)26-16-10-8-9-15-13-20(4,5)27-18(15)16/h8-10,14H,7,11-13H2,1-6H3

Canonical SMILES

CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C

Isomeric SMILES

CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C

Synonyms
        
            Oncol 5G
        
            Benfuracarb
        
            82560-54-1
        
            Aminofuracarb
        
            Oncol
        
            Furacon
        
            Caswell No. 349C
        
            Benfuracarb [BSI:ISO]
        
            UNII-807671FRZY
        
            OK 174
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 - Carboxylic acid ester - Carbonic acid derivative - Oxacycle - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - 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 Weight410.529
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count10
Complexity543
Monoisotopic Mass410.188
Exact Mass410.188
XLogP4.2
Formal Charge0
Heavy Atom Count28
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+0.8481
Human Intestinal AbsorptionHIA+0.9940
Caco-2 PermeabilityCaco2-0.5655
P-glycoprotein SubstrateSubstrate0.6682
P-glycoprotein InhibitorInhibitor0.6000
Non-inhibitor0.8298
Renal Organic Cation TransporterNon-inhibitor0.8172
Distribution
Subcellular localizationMitochondria0.5954
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6234
CYP450 2D6 SubstrateNon-substrate0.7646
CYP450 3A4 SubstrateSubstrate0.6734
CYP450 1A2 InhibitorNon-inhibitor0.7311
CYP450 2C9 InhibitorNon-inhibitor0.5861
CYP450 2D6 InhibitorNon-inhibitor0.8655
CYP450 2C19 InhibitorNon-inhibitor0.5220
CYP450 3A4 InhibitorNon-inhibitor0.6994
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6419
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9247
Non-inhibitor0.6669
AMES ToxicityNon AMES toxic0.5769
CarcinogensNon-carcinogens0.7619
Fish ToxicityHigh FHMT0.9987
Tetrahymena Pyriformis ToxicityHigh TPT0.9925
Honey Bee ToxicityHigh HBT0.5941
BiodegradationNot ready biodegradable0.9894
Acute Oral ToxicityII0.7123
Carcinogenicity (Three-class)Non-required0.5873
Model Value Unit
Absorption
Aqueous solubility-4.6475LogS
Caco-2 Permeability1.1082LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.6162LD50, mol/kg
Fish Toxicity1.0236pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7044pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PotatoJapan0.5ppm
Chicken,FatJapan0.5ppm
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
MaizeBritain0.05mg/kg
TriticaleBritain0.05mg/kg
OatsBritain0.05mg/kg
SorghumBritain0.05mg/kg
BarleyBritain0.05mg/kg
RyeBritain0.05mg/kg
WheatBritain0.05mg/kg
HopBritain5mg/kg
TeaBritain0.1mg/kg
Ware PotatoesBritain0.05mg/kg
Early PotatoesBritain0.05mg/kg
Other OilseedsBritain0.05mg/kg
Hemp SeedBritain0.05mg/kg

References

TitleJournalDatePubmed ID
Fate of benfuracarb insecticide in mollisols and brinjal crop.Bull Environ Contam Toxicol2009 Sep19333533
[Behavior of N-methylcarbamate pesticides during refinement processing of edible oils].J Oleo Sci200717898465
Application of liquid chromatography with electrospray tandem mass spectrometryto the determination of a new generation of pesticides in processed fruits andvegetables.J Chromatogr A2004 May 2115146917
Determination of five pesticide residues in oranges by matrix solid-phasedispersion and liquid chromatography to estimate daily intake of consumers.J AOAC Int2001 May-Jun11417653
Matrix solid-phase dispersion microextraction and determination byhigh-performance liquid chromatography with UV detection of pesticide residues incitrus fruit.J Chromatogr A1999 Apr 1610327624

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