Cloethocarb

Basic Info

Common NameCloethocarb(F03982)
2D Structure
Description

Cloethocarb 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 IDF03982
CAS Number51487-69-5
PubChem CID40032
FormulaC11H14ClNO4
IUPAC Name

[2-(2-chloro-1-methoxyethoxy)phenyl] N-methylcarbamate

InChI Key

PITWUHDDNUVBPT-UHFFFAOYSA-N

InChI

InChI=1S/C11H14ClNO4/c1-13-11(14)17-9-6-4-3-5-8(9)16-10(7-12)15-2/h3-6,10H,7H2,1-2H3,(H,13,14)

Canonical SMILES

CNC(=O)OC1=CC=CC=C1OC(CCl)OC

Isomeric SMILES

CNC(=O)OC1=CC=CC=C1OC(CCl)OC

Synonyms
        
            o-(2-Chloro-1-methoxyethoxy)phenyl methylcarbamate
        
            CLOETHOCARB
        
            51487-69-5
        
            Lance
        
            BAS 263
        
            Cloethocarb [BSI:ISO]
        
            BAS 263I
        
            BASF 263
        
            BAS 263-51I
        
            BAS 263-52I
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 - Phenol ether - Carbamic acid ester - Carbonic acid derivative - Acetal - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxygen compound - Carbonyl group - Alkyl halide - Alkyl chloride - 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 Weight259.686
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Complexity240
Monoisotopic Mass259.061
Exact Mass259.061
XLogP1.3
Formal Charge0
Heavy Atom Count17
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+0.9484
Human Intestinal AbsorptionHIA+0.9974
Caco-2 PermeabilityCaco2+0.6281
P-glycoprotein SubstrateNon-substrate0.7884
P-glycoprotein InhibitorNon-inhibitor0.9143
Non-inhibitor0.9498
Renal Organic Cation TransporterNon-inhibitor0.8795
Distribution
Subcellular localizationMitochondria0.7599
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7330
CYP450 2D6 SubstrateNon-substrate0.6343
CYP450 3A4 SubstrateSubstrate0.6294
CYP450 1A2 InhibitorInhibitor0.6910
CYP450 2C9 InhibitorNon-inhibitor0.8516
CYP450 2D6 InhibitorNon-inhibitor0.9153
CYP450 2C19 InhibitorNon-inhibitor0.5000
CYP450 3A4 InhibitorNon-inhibitor0.6538
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6314
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9694
Non-inhibitor0.9525
AMES ToxicityAMES toxic0.6986
CarcinogensNon-carcinogens0.8583
Fish ToxicityHigh FHMT0.9093
Tetrahymena Pyriformis ToxicityHigh TPT0.9923
Honey Bee ToxicityHigh HBT0.6220
BiodegradationNot ready biodegradable0.9497
Acute Oral ToxicityI0.7804
Carcinogenicity (Three-class)Non-required0.6466
Model Value Unit
Absorption
Aqueous solubility-2.5337LogS
Caco-2 Permeability1.0253LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.8339LD50, mol/kg
Fish Toxicity0.0170pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0606pIGC50, ug/L

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