SynCED: Carbaril

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:01 UTC

Update Date

2026-05-14 19:53:41 UTC

Accession Number

CHEM000802

Identification

Common Name

Carbaril

Class

Small Molecule

Description

Carbaril 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. (4)

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Household Toxin
Organic Compound
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Naphthalenol, methylcarbamate	ChEBI
1-Naphthalenyl methylcarbamate	ChEBI
1-Naphthol N-methylcarbamate	ChEBI
1-Naphthyl N-methylcarbamate	ChEBI
alpha-Naphthyl N-methylcarbamate	ChEBI
N-Methyl-1-naphthyl carbamate	ChEBI
N-Methyl-alpha-naphthylurethan	ChEBI
Sevin	ChEBI
Flea and tick powder	Kegg
1-Naphthalenol, methylcarbamic acid	Generator
1-Naphthalenyl methylcarbamic acid	Generator
1-Naphthol N-methylcarbamic acid	Generator
1-Naphthyl N-methylcarbamic acid	Generator
a-Naphthyl N-methylcarbamate	Generator
a-Naphthyl N-methylcarbamic acid	Generator
alpha-Naphthyl N-methylcarbamic acid	Generator
Α-naphthyl N-methylcarbamate	Generator
Α-naphthyl N-methylcarbamic acid	Generator
N-Methyl-1-naphthyl carbamic acid	Generator
N-Methyl-a-naphthylurethan	Generator
N-Methyl-α-naphthylurethan	Generator
1-Naphthyl-N-methylcarbamate	MeSH
Antigale	MeSH
Carbaryl, manganese (2+) salt	MeSH
Carbaryl, nickel (2+) salt	MeSH
Carbyl	MeSH
Carylderm	MeSH
Concentrat vo 18	MeSH
Dog net insecticide poudre	MeSH
Dog-net insecticide poudre	MeSH
DogNet insecticide poudre	MeSH
Fido's free itch	MeSH
Fido's free-itch	MeSH
Fido's freeitch	MeSH
g Wizz	MeSH
g-Wizz	MeSH
GWizz	MeSH
Joseph lyddy	MeSH
Lyddy, joseph	MeSH
Moureau, poudre insecticide	MeSH
Océcoxil	MeSH
Poudre insecticide moureau	MeSH
Poudre insecticide vetoquinol	MeSH
Poutic	MeSH
Skatta tick flea louse powder	MeSH
Sépou	MeSH
Tigal	MeSH
VO 18, concentrat	MeSH
Vetoquinol, poudre insecticide	MeSH
Insecticide moureau, poudre	MeSH
Insecticide vetoquinol, poudre	MeSH
Biové brand OF carbaril	MeSH
Carbaril avicopharma brand	MeSH
Carbaril novartis brand	MeSH
Carbaril ornis brand	MeSH
Novartis brand OF carbaril	MeSH
Carbaril biové brand	MeSH
Carbaril mavlab brand	MeSH
Clément brand OF carbaril	MeSH
intraveno Brand OF carbaril	MeSH
Carbaril clément brand	MeSH
Carbaril intraveno brand	MeSH
Coophavet brand OF carbaril	MeSH
Mavlab brand OF carbaril	MeSH
Sanofi brand OF carbaril	MeSH
18, Concentrat vo	MeSH
Avicopharma brand OF carbaril	MeSH
Carbaril coophavet brand	MeSH
Carbaril sanofi brand	MeSH
Carbaril sogeval brand	MeSH
Carbaril virbac brand	MeSH
Carbaril vétoquinol brand	MeSH
David veterinary laboratories brand OF carbaril	MeSH
Ornis brand OF carbaril	MeSH
Sogeval brand OF carbaril	MeSH
Virbac brand OF carbaril	MeSH
Vétoquinol brand OF carbaril	MeSH

Chemical Formula

C₁₂H₁₁NO₂

Average Molecular Mass

201.221 g/mol

Monoisotopic Mass

201.079 g/mol

CAS Registry Number

63-25-2

IUPAC Name

naphthalen-1-yl N-methylcarbamate

Traditional Name

carbaryl

SMILES

CNC(=O)OC1=C2C=CC=CC2=CC=C1

InChI Identifier

InChI=1S/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14)

InChI Key

CVXBEEMKQHEXEN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
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 homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

carbamate ester (CHEBI:3390 )
naphthalenes (CHEBI:3390 )
Carbamate pesticides (C07491 )
Carbamate insecticides (C07491 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	145°C
Boiling Point	Not Available
Solubility	0.11 mg/mL at 22°C [USDA PESTICIDE PROPERTIES DATABASE]

Predicted Properties

Property	Value	Source
Water Solubility	0.091 g/L	ALOGPS
logP	2.45	ALOGPS
logP	2.46	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.21 m³·mol⁻¹	ChemAxon
Polarizability	21.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Inhalation (3) ; oral (3); dermal (3)

Mechanism of Toxicity

Carbaril is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Metabolism

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (3)

Toxicity Values

LD50: 230 mg/kg (Oral, Rat) (5) LD50: 4000 mg/kg (Dermal, Rat) (5) LD50: 64 mg/kg (Intraperitoneal, Rat) (5) LD50: 1400 mg/kg (Subcutaneous, Rat) (5) LD50: 41 900 ug/kg (Intravenous, Rat) (5)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (2)

Uses/Sources

Carbaril is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (1).

Symptoms

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (4)

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0249612

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID