Basic Info

Common NameMetolcarb(F04011)
2D Structure
Description

Metolcarb 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 IDF04011
CAS Number1129-41-5
PubChem CID14322
FormulaC9H11NO2
IUPAC Name

(3-methylphenyl) N-methylcarbamate

InChI Key

VOEYXMAFNDNNED-UHFFFAOYSA-N

InChI

InChI=1S/C9H11NO2/c1-7-4-3-5-8(6-7)12-9(11)10-2/h3-6H,1-2H3,(H,10,11)

Canonical SMILES

CC1=CC(=CC=C1)OC(=O)NC

Isomeric SMILES

CC1=CC(=CC=C1)OC(=O)NC

WikipediaMetolcarb
Synonyms
        
            3-Tolyl N-methylcarbamate
        
            METOLCARB
        
            m-Tolyl methylcarbamate
        
            Metacrate
        
            MTMC
        
            Tsumacide
        
            m-Cresyl methylcarbamate
        
            1129-41-5
        
            3-Tolyl methylcarbamate
        
            m-Tolyl N-methylcarbamate
        
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 - Phenoxy compound - Toluene - 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 Weight165.192
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity159
Monoisotopic Mass165.079
Exact Mass165.079
XLogP1.7
Formal Charge0
Heavy Atom Count12
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+0.9709
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7768
P-glycoprotein SubstrateNon-substrate0.8597
P-glycoprotein InhibitorNon-inhibitor0.9667
Non-inhibitor0.9710
Renal Organic Cation TransporterNon-inhibitor0.8938
Distribution
Subcellular localizationMitochondria0.7395
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7776
CYP450 2D6 SubstrateSubstrate0.8411
CYP450 3A4 SubstrateSubstrate0.5104
CYP450 1A2 InhibitorInhibitor0.5051
CYP450 2C9 InhibitorNon-inhibitor0.9815
CYP450 2D6 InhibitorNon-inhibitor0.9291
CYP450 2C19 InhibitorNon-inhibitor0.9574
CYP450 3A4 InhibitorNon-inhibitor0.9335
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8677
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9376
Non-inhibitor0.9702
AMES ToxicityAMES toxic0.5121
CarcinogensNon-carcinogens0.8685
Fish ToxicityHigh FHMT0.7020
Tetrahymena Pyriformis ToxicityHigh TPT0.9698
Honey Bee ToxicityHigh HBT0.8353
BiodegradationNot ready biodegradable0.6165
Acute Oral ToxicityII0.7495
Carcinogenicity (Three-class)Non-required0.5338

Model Value Unit
Absorption
Aqueous solubility-2.0337LogS
Caco-2 Permeability1.5824LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7588LD50, mol/kg
Fish Toxicity1.7742pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.0768pIGC50, ug/L

References

TitleJournalDatePubmed ID
Prussian blue mediated amplification combined with signal enhancement of ordered mesoporous carbon for ultrasensitive and specific quantification of metolcarb by a three-dimensional molecularly imprinted electrochemical sensor.Biosens Bioelectron2015 Feb 1525240126
Rapid and sensitive suspension array for multiplex detection of organophosphorus pesticides and carbamate pesticides based on silica-hydrogel hybrid microbeads.J Hazard Mater2014 May 3024769809
Extraction of carbamate pesticides in fruit samples by graphene reinforced hollowfibre liquid microextraction followed by high performance liquid chromatographic detection.Food Chem2014 Aug 1524679760
Rapid determination of metolcarb residues in foods using a biomimeticenzyme-linked immunosorbent assay employing a novel molecularly imprinted polymerfilm as artificial antibody.J AOAC Int2013 Mar-Apr23767373
Determination of metolcarb in food by capillary electrophoresis immunoassay with a laser-induced fluorescence detector.Electrophoresis2012 May22648817
Development of chemiluminescence enzyme-linked immunosorbent assay for thescreening of metolcarb and carbaryl in orange juice, cabbage and cucumber.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2010Mar20155539
Synthesis and insecticidal activity of novel carbamate derivatives as potentialdual-binding site acetylcholinesterase inhibitors.J Agric Food Chem2010 Dec 2221114293
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
Development of an enzyme-linked immunosorbent assay for metolcarb residueanalysis and investigation of matrix effects from different agriculturalproducts.Anal Bioanal Chem2009 Aug19575189
Atmospheric pressure glow discharge desorption mass spectrometry for rapidscreening of pesticides in food.Rapid Commun Mass Spectrom2008 Sep18697232
Metal-organic frameworks supported surface-imprinted nanoparticles for thesensitive detection of metolcarb.NoneNone26735869

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