Basic Info

Common NameDebacarb(F03984)
2D Structure
Description

Debacarb 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 IDF03984
CAS Number62732-91-6
PubChem CID62208
FormulaC14H19N3O4
IUPAC Name

2-(2-ethoxyethoxy)ethyl N-(1H-benzimidazol-2-yl)carbamate

InChI Key

DNBMPXLFKQCOBV-UHFFFAOYSA-N

InChI

InChI=1S/C14H19N3O4/c1-2-19-7-8-20-9-10-21-14(18)17-13-15-11-5-3-4-6-12(11)16-13/h3-6H,2,7-10H2,1H3,(H2,15,16,17,18)

Canonical SMILES

CCOCCOCCOC(=O)NC1=NC2=CC=CC=C2N1

Isomeric SMILES

CCOCCOCCOC(=O)NC1=NC2=CC=CC=C2N1

Synonyms
        
            Debacarb [ISO]
        
            Carbamic acid, 1H-benzimidazol-2-yl-, 2-(2-ethoxyethoxy)ethyl ester
        
            Debacarb
        
            62732-91-6
        
            UNII-P87O1S290W
        
            P87O1S290W
        
            2-(2-Ethoxyethoxy)ethyl 2-benzimidazole carbamate
        
            2-(2-Ethoxyethoxy)ethyl 1H-benzimidazol-2-ylcarbamate
        
            AC1L1WOG
        
            SCHEMBL22401
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassBenzimidazoles
Subclass2-benzimidazolylcarbamic acid esters
Intermediate Tree NodesNot available
Direct Parent2-benzimidazolylcarbamic acid esters
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents2-benzimidazolylcarbamic acid ester - Benzenoid - Azole - Imidazole - Carbamic acid ester - Heteroaromatic compound - Carbonic acid derivative - Dialkyl ether - Ether - Azacycle - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.

Properties

Property NameProperty Value
Molecular Weight293.323
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count9
Complexity317
Monoisotopic Mass293.138
Exact Mass293.138
XLogP1.6
Formal Charge0
Heavy Atom Count21
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+0.9261
Human Intestinal AbsorptionHIA+0.9875
Caco-2 PermeabilityCaco2-0.6463
P-glycoprotein SubstrateSubstrate0.7111
P-glycoprotein InhibitorNon-inhibitor0.6426
Non-inhibitor0.9222
Renal Organic Cation TransporterNon-inhibitor0.8187
Distribution
Subcellular localizationMitochondria0.5633
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8218
CYP450 2D6 SubstrateNon-substrate0.7804
CYP450 3A4 SubstrateNon-substrate0.5979
CYP450 1A2 InhibitorInhibitor0.5932
CYP450 2C9 InhibitorNon-inhibitor0.7793
CYP450 2D6 InhibitorNon-inhibitor0.8586
CYP450 2C19 InhibitorNon-inhibitor0.6891
CYP450 3A4 InhibitorNon-inhibitor0.9626
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7286
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8975
Non-inhibitor0.7449
AMES ToxicityNon AMES toxic0.6450
CarcinogensNon-carcinogens0.9508
Fish ToxicityHigh FHMT0.9757
Tetrahymena Pyriformis ToxicityHigh TPT0.9855
Honey Bee ToxicityLow HBT0.6835
BiodegradationNot ready biodegradable0.9909
Acute Oral ToxicityIII0.6516
Carcinogenicity (Three-class)Non-required0.5749

Model Value Unit
Absorption
Aqueous solubility-3.6674LogS
Caco-2 Permeability0.4004LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4406LD50, mol/kg
Fish Toxicity1.5583pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3785pIGC50, 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