ContaminantDB: Ethiofencarb

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:03 UTC

Update Date

2026-03-25 19:25:57 UTC

Accession Number

CHEM000825

Identification

Common Name

Ethiofencarb

Class

Small Molecule

Description

Ethiofencarb is a carbamate pesticide. Systemic agricultural insecticide. Ethiofencarb is used for control of aphids on hard and soft fruits, vegetables and sugar beet. Ethiofencarb belongs to the family of Aromatic Homomonocyclic Compounds. These are aromatic compounds containig only one ring, which is homocyclic.

Contaminant Sources

FooDB Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Ether
Food Toxin
Metabolite
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-((Ethylthio)methyl)phenol methylcarbamate	ChEBI
2-((Ethylthio)methyl)phenyl methylcarbamate	ChEBI
alpha-(Ethylthio)-O-tolyl methylcarbamate	ChEBI
alpha-Ethylthio-O-tolyl methylcarbamate	ChEBI
Croneton	ChEBI
2-((Ethylthio)methyl)phenol methylcarbamic acid	Generator
2-((Ethylthio)methyl)phenyl methylcarbamic acid	Generator
a-(Ethylthio)-O-tolyl methylcarbamate	Generator
a-(Ethylthio)-O-tolyl methylcarbamic acid	Generator
alpha-(Ethylthio)-O-tolyl methylcarbamic acid	Generator
Α-(ethylthio)-O-tolyl methylcarbamate	Generator
Α-(ethylthio)-O-tolyl methylcarbamic acid	Generator
a-Ethylthio-O-tolyl methylcarbamate	Generator
a-Ethylthio-O-tolyl methylcarbamic acid	Generator
alpha-Ethylthio-O-tolyl methylcarbamic acid	Generator
Α-ethylthio-O-tolyl methylcarbamate	Generator
Α-ethylthio-O-tolyl methylcarbamic acid	Generator
(2-Ethylthiomethyl-phenyl)-N-methylcarbamate	HMDB
2-(Ethylthiomethyl)phenyl methylcarbamate, 9ci	HMDB
2-Ethyl-mercaptomethyl-phenyl-N-methylcarbamate	HMDB
2-Ethylthiomethylphenyl N-methylcarbamate	HMDB
2-[(Ethylsulfanyl)methyl]phenyl methylcarbamate	HMDB
Arylmate	HMDB
BAY-hox-1901	HMDB
Carbamic acid, methyl-, 2-(ethylthiomethyl)phenyl ester	HMDB
Carbamic acid, methyl-, alpha-(ethylthio)-O-tolyl ester	HMDB
Croneton 500	HMDB
Ethiophencarbe	HMDB
Kronetone	HMDB
N-Methyl-O-(2-ethylthiomethyl) phenylcarbamate	HMDB
Phenol, 2-((ethylthio)methyl)-, methylcarbamate	HMDB
Phenol, 2-((ethylthio)methyl)-, methylcarbamate (9ci)	HMDB
Phenol, 2-[(ethylthio)methyl]-, methylcarbamate	HMDB
Kroneton	HMDB

Chemical Formula

C₁₁H₁₅NO₂S

Average Molecular Mass

225.307 g/mol

Monoisotopic Mass

225.082 g/mol

CAS Registry Number

29973-13-5

IUPAC Name

1-{2-[(ethylsulfanyl)methyl]phenoxy}-N-methylmethanimidic acid

Traditional Name

1-2-[(ethylsulfanyl)methyl]phenoxy-N-methylmethanimidic acid

SMILES

CCSCC1=CC=CC=C1OC(O)=NC

InChI Identifier

InChI=1S/C11H15NO2S/c1-3-15-8-9-6-4-5-7-10(9)14-11(13)12-2/h4-7H,3,8H2,1-2H3,(H,12,13)

InChI Key

HEZNVIYQEUHLNI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenyl methylcarbamates

Direct Parent

Phenyl methylcarbamates

Alternative Parents

Substituents

Phenyl methylcarbamate
Phenoxy compound
Carbamic acid ester
Carbonic acid derivative
Thioether
Sulfenyl compound
Dialkylthioether
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:38483 )
Carbamate insecticides (C18649 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
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	33.4°C
Boiling Point	Not Available
Solubility	1.82 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.76	ALOGPS
logP	3.13	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	2.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63.58 m³·mol⁻¹	ChemAxon
Polarizability	23.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-5900000000-a0e811b07807c20dc226	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05d0-9450000000-a60b46f1581a965f9032	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0fri-2900000000-bf3fb5f61e7feada8244	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-88bea6aea0d489c3f2c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0udi-3900000000-46322dfaf2d53e16a49d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0900000000-29066967c94841f1d9e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0udi-4900000000-235640fb18dd10be8316	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0f79-5900000000-1bc801b831d549388ecd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0900000000-f5a1672c171880c2db04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02di-6930000000-f6673165e1a176b115db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08fr-9600000000-b5a2082ff68df8b1e4e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-9200000000-8ab2ca87a079db8a8838	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-9310000000-94bc3480b80e35059030	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-9300000000-153b9e9dba9bd6921897	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bt9-9200000000-58c7056048f6ab3a59db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0980000000-45a70864a14bdde67c9a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2900000000-52ac022ae80cc42785d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-63473c24d7f7238b1d94	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-9120000000-130d83cd4bb2f5f4cc67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-9000000000-7cddd57379173ec27f5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fr-9000000000-f7b8425c2b01328b6cf9	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (2) ; oral (2); dermal (2)

Mechanism of Toxicity

Ethiofencarb 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. (2)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Ethiofencarb 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. (3)

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

HMDB0031782

FooDB ID

FDB008455

Phenol Explorer ID

Not Available

KNApSAcK ID