Basic Info

Common NameFenobucarb(F03995)
2D Structure
Description

Fenobucarb 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 IDF03995
CAS Number3766-81-2
PubChem CID19588
FormulaC12H17NO2
IUPAC Name

(2-butan-2-ylphenyl) N-methylcarbamate

InChI Key

DIRFUJHNVNOBMY-UHFFFAOYSA-N

InChI

InChI=1S/C12H17NO2/c1-4-9(2)10-7-5-6-8-11(10)15-12(14)13-3/h5-9H,4H2,1-3H3,(H,13,14)

Canonical SMILES

CCC(C)C1=CC=CC=C1OC(=O)NC

Isomeric SMILES

CCC(C)C1=CC=CC=C1OC(=O)NC

Synonyms
        
            Hopcin
        
            Fenobucarb
        
            BPMC
        
            3766-81-2
        
            2-sec-Butylphenyl N-methylcarbamate
        
            Baycarb
        
            Bassa
        
            Fenobcarb
        
            Barizon
        
            Carvil
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenyl methylcarbamates
Intermediate Tree NodesNot available
Direct ParentPhenyl methylcarbamates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenyl methylcarbamate - Phenylpropane - Phenoxy compound - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Properties

Property NameProperty Value
Molecular Weight207.273
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Complexity206
Monoisotopic Mass207.126
Exact Mass207.126
XLogP2.8
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+0.9789
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7839
P-glycoprotein SubstrateNon-substrate0.8181
P-glycoprotein InhibitorNon-inhibitor0.8686
Non-inhibitor0.9044
Renal Organic Cation TransporterNon-inhibitor0.9229
Distribution
Subcellular localizationMitochondria0.7428
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7768
CYP450 2D6 SubstrateSubstrate0.7464
CYP450 3A4 SubstrateSubstrate0.5308
CYP450 1A2 InhibitorInhibitor0.7361
CYP450 2C9 InhibitorNon-inhibitor0.8564
CYP450 2D6 InhibitorNon-inhibitor0.8017
CYP450 2C19 InhibitorNon-inhibitor0.8236
CYP450 3A4 InhibitorNon-inhibitor0.9158
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6704
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9187
Non-inhibitor0.9311
AMES ToxicityAMES toxic0.5306
CarcinogensNon-carcinogens0.7996
Fish ToxicityHigh FHMT0.9150
Tetrahymena Pyriformis ToxicityHigh TPT0.9481
Honey Bee ToxicityHigh HBT0.7985
BiodegradationNot ready biodegradable0.8801
Acute Oral ToxicityII0.8390
Carcinogenicity (Three-class)Non-required0.5368

Model Value Unit
Absorption
Aqueous solubility-3.0190LogS
Caco-2 Permeability1.6575LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.4547LD50, mol/kg
Fish Toxicity1.2268pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3068pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
CherryJapan0.3ppm

References

TitleJournalDatePubmed ID
Nano carbon black-based screen printed sensor for carbofuran, isoprocarb,carbaryl and fenobucarb detection: application to grain samples.Talanta2018 Aug 1529784378
Determination of fenobucarb residues in animal and aquatic food products usingliquid chromatography-tandem mass spectrometry coupled with a QuEChERS extractionmethod.J Chromatogr B Analyt Technol Biomed Life Sci2017 Jul 1528514648
Pesticide pollution of multiple drinking water sources in the Mekong Delta,Vietnam: evidence from two provinces.Environ Sci Pollut Res Int2015 Jun25572267
Pesticide-contaminated feeds in integrated grass carp aquaculture: toxicology andbioaccumulation.Dis Aquat Organ2014 Feb 1924553419
Quantifying fenobucarb residue levels in beef muscles using liquidchromatography-tandem mass spectrometry and QuEChERS sample preparation.Food Chem2013 Jun 1523497890
Multivariate study of parameters in the determination of pesticide residues inapple by headspace solid phase microextraction coupled to gas chromatography-massspectrometry using experimental factorial design.Food Chem2013 Dec 1523993624
Determination of four carbamate pesticides in corn by cloud point extraction and high-performance liquid chromatography in the visible region based on theirderivatization reaction.J Agric Food Chem2009 Oct 1419807151
Sequential injection kinetic spectrophotometric determination of quaternarymixtures of carbamate pesticides in water and fruit samples using artificialneural networks for multivariate calibration.Spectrochim Acta A Mol Biomol Spectrosc2009 Dec19864181
Multiresidue analysis of 47 pesticides in cooked wheat flour and polished rice byliquid chromatography with tandem mass spectrometry.Biomed Chromatogr2009 Apr19039807
Competitive degradation and detoxification of carbamate insecticides by membrane anodic Fenton treatment.J Agric Food Chem2003 Aug 2712926887

Targets

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
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