Furathiocarb

Basic Info

Common NameFurathiocarb(F04000)
2D Structure
Description

Furathiocarb 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 IDF04000
CAS Number65907-30-4
PubChem CID47759
FormulaC18H26N2O5S
IUPAC Name

(2,2-dimethyl-3H-1-benzofuran-7-yl) N-[butoxycarbonyl(methyl)amino]sulfanyl-N-methylcarbamate

InChI Key

HAWJXYBZNNRMNO-UHFFFAOYSA-N

InChI

InChI=1S/C18H26N2O5S/c1-6-7-11-23-16(21)19(4)26-20(5)17(22)24-14-10-8-9-13-12-18(2,3)25-15(13)14/h8-10H,6-7,11-12H2,1-5H3

Canonical SMILES

CCCCOC(=O)N(C)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C

Isomeric SMILES

CCCCOC(=O)N(C)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C

Synonyms
        
            Furathiocarb
        
            Deltanit
        
            65907-30-4
        
            Deltanet
        
            Promet
        
            Promet 660SCO
        
            UNII-WZI2IZ80UY
        
            Furathiocarb [BSI:ISO]
        
            CGA 73102
        
            HSDB 6664
Classifies
                

                  
                    Pollutant
                  
                    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 Weight382.475
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Complexity502
Monoisotopic Mass382.156
Exact Mass382.156
XLogP4.7
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+0.8562
Human Intestinal AbsorptionHIA+0.9942
Caco-2 PermeabilityCaco2-0.5666
P-glycoprotein SubstrateNon-substrate0.5527
P-glycoprotein InhibitorInhibitor0.5201
Non-inhibitor0.8332
Renal Organic Cation TransporterNon-inhibitor0.9044
Distribution
Subcellular localizationMitochondria0.5887
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5678
CYP450 2D6 SubstrateNon-substrate0.7842
CYP450 3A4 SubstrateSubstrate0.6442
CYP450 1A2 InhibitorNon-inhibitor0.6047
CYP450 2C9 InhibitorNon-inhibitor0.5227
CYP450 2D6 InhibitorNon-inhibitor0.8785
CYP450 2C19 InhibitorNon-inhibitor0.5298
CYP450 3A4 InhibitorNon-inhibitor0.6547
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6959
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9788
Non-inhibitor0.7913
AMES ToxicityNon AMES toxic0.5758
CarcinogensNon-carcinogens0.8108
Fish ToxicityHigh FHMT0.9936
Tetrahymena Pyriformis ToxicityHigh TPT0.9907
Honey Bee ToxicityHigh HBT0.6570
BiodegradationNot ready biodegradable0.9561
Acute Oral ToxicityII0.7190
Carcinogenicity (Three-class)Non-required0.5808
Model Value Unit
Absorption
Aqueous solubility-4.3066LogS
Caco-2 Permeability1.1367LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.8271LD50, mol/kg
Fish Toxicity0.8287pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6984pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Egg PlantJapan0.3ppm
CardoonsBritain0.05mg/kg
AsparagusBritain0.05mg/kg
Other Legume Vegetables (Fresh)Britain0.05mg/kg
Peas (Without Pods)Britain0.05mg/kg
Peas (With Pods)Britain0.05mg/kg
Beans (Without Pods)Britain0.05mg/kg
Beans (With Pods)Britain0.05mg/kg
Other HerbsBritain0.05mg/kg
CeleryBritain0.05mg/kg
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
OatsBritain0.05mg/kg
SorghumBritain0.05mg/kg

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