SynCED: Chlorpropham

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:02 UTC

Update Date

2026-08-17 23:16:23 UTC

Accession Number

CHEM000811

Identification

Common Name

Chlorpropham

Class

Small Molecule

Description

Chlorpropham 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

HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Ether
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3-Chlorophenyl)carbamic acid, 1-methylethyl ester	ChEBI
1-Methylethyl (3-chlorophenyl)carbamate	ChEBI
3-Chlorocarbanilic acid, isopropyl ester	ChEBI
Chloropropham	ChEBI
Chlorprophame	ChEBI
Isopropyl (3-chlorophenyl)carbamate	ChEBI
Isopropyl 3-chlorocarbanilate	ChEBI
Isopropyl 3-chlorophenylcarbamate	ChEBI
Isopropyl m-chlorocarbanilate	ChEBI
Isopropyl meta-chlorocarbanilate	ChEBI
Isopropyl N-(3-chlorophenyl)carbamate	ChEBI
Isopropyl N-(m-chlorophenyl)carbamate	ChEBI
Isopropyl-m-chlorocarbanilate	ChEBI
Isopropyl-N-(3-chlorophenyl)carbamate	ChEBI
Isopropyl-N-(3-chlorphenyl)-carbamat	ChEBI
Isopropyl-N-3-chlorophenyl carbamate	ChEBI
Isopropyl-N-m-chlorophenyl-carbamate	ChEBI
m-Chlorocarbanilic acid isopropyl ester	ChEBI
m-Chlorocarbanilic acid, isopropyl ester	ChEBI
N-(3-Chlorophenyl)carbamic acid, isopropyl ester	ChEBI
N-(3-Chlorophenyl)isopropyl carbamate	ChEBI
N-3-Chlorophenylisopropylcarbamate	ChEBI
O-Isopropyl N-(3-chlorophenyl)carbamate	ChEBI
(3-Chlorophenyl)carbamate, 1-methylethyl ester	Generator
1-Methylethyl (3-chlorophenyl)carbamic acid	Generator
3-Chlorocarbanilate, isopropyl ester	Generator
Isopropyl (3-chlorophenyl)carbamic acid	Generator
Isopropyl 3-chlorocarbanilic acid	Generator
Isopropyl 3-chlorophenylcarbamic acid	Generator
Isopropyl m-chlorocarbanilic acid	Generator
Isopropyl meta-chlorocarbanilic acid	Generator
Isopropyl N-(3-chlorophenyl)carbamic acid	Generator
Isopropyl N-(m-chlorophenyl)carbamic acid	Generator
Isopropyl-m-chlorocarbanilic acid	Generator
Isopropyl-N-(3-chlorophenyl)carbamic acid	Generator
Isopropyl-N-3-chlorophenyl carbamic acid	Generator
Isopropyl-N-m-chlorophenyl-carbamic acid	Generator
m-Chlorocarbanilate isopropyl ester	Generator
m-Chlorocarbanilate, isopropyl ester	Generator
N-(3-Chlorophenyl)carbamate, isopropyl ester	Generator
N-(3-Chlorophenyl)isopropyl carbamic acid	Generator
N-3-Chlorophenylisopropylcarbamic acid	Generator
O-Isopropyl N-(3-chlorophenyl)carbamic acid	Generator
CIPC	MeSH
Isopropyl N-(3-chlorophenol)carbamate	MeSH

Chemical Formula

C₁₀H₁₂ClNO₂

Average Molecular Mass

213.661 g/mol

Monoisotopic Mass

213.056 g/mol

CAS Registry Number

101-21-3

IUPAC Name

propan-2-yl N-(3-chlorophenyl)carbamate

Traditional Name

isopropyl m-chlorocarbanilate

SMILES

CC(C)OC(=O)NC1=CC=CC(Cl)=C1

InChI Identifier

InChI=1S/C10H12ClNO2/c1-7(2)14-10(13)12-9-5-3-4-8(11)6-9/h3-7H,1-2H3,(H,12,13)

InChI Key

CWJSHJJYOPWUGX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylcarbamic acid esters

Direct Parent

Phenylcarbamic acid esters

Alternative Parents

Substituents

Phenylcarbamic acid ester
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Carbamic acid ester
Carbonic acid derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:34630 )
monochlorobenzenes (CHEBI:34630 )
benzenes (CHEBI:34630 )
Carbanilate herbicides (C14506 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

herbicide

Biological Roles

plant growth retardant

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	41°C
Boiling Point	Not Available
Solubility	0.089 mg/mL at 25°C [TOMLIN,C (2003)]

Predicted Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	3.03	ALOGPS
logP	3.21	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.52 m³·mol⁻¹	ChemAxon
Polarizability	21.31 Å³	ChemAxon
Number of Rings	1	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

Chlorpropham 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

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Chlorpropham 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

HMDB0250135

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID