ContaminantDB: Bendiocarb

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:00 UTC

Update Date

2026-03-26 19:43:30 UTC

Accession Number

CHEM000788

Identification

Common Name

Bendiocarb

Class

Small Molecule

Description

Bendiocarb is a carbamate pesticide. Bendiocarb is a carbamate insecticide. 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. All bendiocarb-containing products in the United States were recently cancelled, after its manufacturers voluntarily chose to pull their products off the market, rather than conduct additional safety studies required by the EPA. In other countries, Bendiocarb is still used in homes, industrial plants, and food storage sites to control bedbugs, mosquitoes, flies, wasps, ants, fleas, cockroaches, silverfish, and ticks but can be used against a wide variety of insects as well as snails and slugs. It is one of 12 insecticides recommended by the World Health Organization for use in malaria control. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps.

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Food Toxin
Industrial/Workplace Toxin
Insecticide
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2-Dimethyl-1,3-benzodioxol-4-ol methylcarbamate	ChEBI
2,2-Dimethyl-4-(methylcarbamoyloxy)-1,3-benzodioxole	ChEBI
2,3-Isopropylidenedioxyphenyl methylcarbamate	ChEBI
2,2-Dimethyl-1,3-benzodioxol-4-ol methylcarbamic acid	Generator
2,3-Isopropylidenedioxyphenyl methylcarbamic acid	Generator
FICAM	MeSH
FICAM 80W	MeSH
FICAM W	MeSH

Chemical Formula

C₁₁H₁₃NO₄

Average Molecular Mass

223.225 g/mol

Monoisotopic Mass

223.084 g/mol

CAS Registry Number

22781-23-3

IUPAC Name

2,2-dimethyl-2H-1,3-benzodioxol-4-yl N-methylcarbamate

Traditional Name

bendiocarb

SMILES

CNC(=O)OC1=CC=CC2=C1OC(C)(C)O2

InChI Identifier

InChI=1S/C11H13NO4/c1-11(2)15-8-6-4-5-7(9(8)16-11)14-10(13)12-3/h4-6H,1-3H3,(H,12,13)

InChI Key

XEGGRYVFLWGFHI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Ketal
Benzenoid
Carbamic acid ester
Carbonic acid derivative
Oxacycle
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:34556 )
benzodioxoles (CHEBI:34556 )
Carbamate insecticides (C14433 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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	129.5°C
Boiling Point	Not Available
Solubility	0.26 mg/mL at 25°C [USDA PESTICIDE PROPERTIES DATABASE]

Predicted Properties

Property	Value	Source
Water Solubility	2.39 g/L	ALOGPS
logP	1.53	ALOGPS
logP	1.57	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.76	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	56.39 m³·mol⁻¹	ChemAxon
Polarizability	22.59 Å³	ChemAxon
Number of Rings	2	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	splash10-05n0-5910000000-388bfdb7c1f8fec41b82	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-0900000000-4c9c8eb18ec863c33a90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-014i-0900000000-6730488e5e66f4178394	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0aor-1900000000-e5a59a41a94ae52d5261	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-004i-0900000000-e047f05235db657d55c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0900000000-f5ece9ccfaba50f366c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-016r-0900000000-a5477a28d7dce03b2640	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-bee21ca6edccbcd482d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-1d5ca06b865c03681cb6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-0a4i-2900000000-d1bc81970f7b5189c0ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-053r-9800000000-95f768f5d54a780065a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-4970000000-3f323afd9f10568bbbe8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aor-3910000000-750ff9ee81afc648efa9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9600000000-f5c34e6a6eaefb01451e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-9550000000-ebe6168ce90681e76228	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-7920000000-7ca3158aef0e02a4717d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-9400000000-aba2ddc92bd8439a43b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-4ca51b24bd1ba39dab7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-8c33b2106ce81aad9d02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056v-9500000000-54ad6df857e761677aa7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-0960000000-b12a237f3804ece92095	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-81b6a7779c3f7354a563	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-1900000000-a9476af35e2e340ef929	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-5900000000-4e6a18c5310b2dfe28d3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

Bendiocarb 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

LD50: 50 mg/kg (Oral, Rat); LD50: 700 mg/kg (Dermal, Rat); LD50 35-40 mg/kg (Oral, Rabbits); LD50: 35 mg/kg (Oral, Guinea Pigs) (4)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Pesticide, widely used in agriculture production.

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

HMDB0248947

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Bendiocarb

Chemspider ID

2224

ChEBI ID

34556

PubChem Compound ID

Not Available

Kegg Compound ID

C14433

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Bendiocarb (CHEM000788)

Structure for CHEM000788: Bendiocarb