Basic Info

Common NameCarbanolate(F03971)
2D Structure
Description

Carbanolate 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 IDF03971
CAS Number671-04-5
PubChem CID12636
FormulaC10H12ClNO2
IUPAC Name

(2-chloro-3,4-dimethylphenyl) N-methylcarbamate

InChI Key

FNAAOMSRAVKQGQ-UHFFFAOYSA-N

InChI

InChI=1S/C10H12ClNO2/c1-6-4-5-8(9(11)7(6)2)14-10(13)12-3/h4-5H,1-3H3,(H,12,13)

Canonical SMILES

CC1=C(C(=C(C=C1)OC(=O)NC)Cl)C

Isomeric SMILES

CC1=C(C(=C(C=C1)OC(=O)NC)Cl)C

Synonyms
        
            2-Chloro-3,4-dimethylphenyl N-methylcarbamate
        
            Phenol, 2-chloro-3,4-dimethyl-, 1-(N-methylcarbamate)
        
            UNII-3LJD4G02CI
        
            3LJD4G02CI
        
            2-Chloro-3,4-xylyl methylcarbamate
        
            AC1Q3L1H
        
            Phenol, 2-chloro-3,4-dimethyl-, methylcarbamate
        
            AC1L200R
        
            SCHEMBL5934117
        
            CHEBI:82090
        
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 - O-xylene - Xylene - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - 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 Weight213.661
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity210
Monoisotopic Mass213.056
Exact Mass213.056
XLogP2.9
Formal Charge0
Heavy Atom Count14
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+0.9783
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7511
P-glycoprotein SubstrateNon-substrate0.8650
P-glycoprotein InhibitorNon-inhibitor0.9583
Non-inhibitor0.9814
Renal Organic Cation TransporterNon-inhibitor0.9027
Distribution
Subcellular localizationMitochondria0.7653
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7602
CYP450 2D6 SubstrateSubstrate0.6094
CYP450 3A4 SubstrateSubstrate0.6394
CYP450 1A2 InhibitorInhibitor0.8547
CYP450 2C9 InhibitorNon-inhibitor0.7480
CYP450 2D6 InhibitorNon-inhibitor0.8664
CYP450 2C19 InhibitorInhibitor0.5750
CYP450 3A4 InhibitorNon-inhibitor0.8235
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6205
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9102
Non-inhibitor0.9302
AMES ToxicityAMES toxic0.7036
CarcinogensNon-carcinogens0.7957
Fish ToxicityHigh FHMT0.9208
Tetrahymena Pyriformis ToxicityHigh TPT0.9921
Honey Bee ToxicityHigh HBT0.7428
BiodegradationNot ready biodegradable0.9759
Acute Oral ToxicityI0.7770
Carcinogenicity (Three-class)Non-required0.5315

Model Value Unit
Absorption
Aqueous solubility-3.4146LogS
Caco-2 Permeability1.8091LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.0541LD50, mol/kg
Fish Toxicity1.0312pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6633pIGC50, ug/L

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