ContaminantDB: Desmedipham

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:02 UTC

Update Date

2026-03-25 19:18:30 UTC

Accession Number

CHEM000817

Identification

Common Name

Desmedipham

Class

Small Molecule

Description

Desmedipham is a selective, systemic post-emergence herbicide of the phenyl carbamate and biscarbamate classes. 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. Desmedipham was developed by Schering AG and approved for use in the United States in 1970. It is commonly used in beet and strawberry crops to protect against weeds, often in comination with Phenmedipham under the trade names Betanal or Betamax. (3)

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
Ether
Herbicide
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-[(Ethoxycarbonyl)amino]phenyl phenylcarbamate	ChEBI
3-Ethoxycarbonylaminophenyl-N-phenylcarbamate	ChEBI
Ethyl 3'-phenylcarbamoyloxycarbanilate	ChEBI
3-[(Ethoxycarbonyl)amino]phenyl phenylcarbamic acid	Generator
3-Ethoxycarbonylaminophenyl-N-phenylcarbamic acid	Generator
Ethyl 3'-phenylcarbamoyloxycarbanilic acid	Generator
Ethyl m-hydroxycarbanilate carbanilate	MeSH

Chemical Formula

C₁₆H₁₆N₂O₄

Average Molecular Mass

300.309 g/mol

Monoisotopic Mass

300.111 g/mol

CAS Registry Number

13684-56-5

IUPAC Name

1-3-{[ethoxy(hydroxy)methylidene]amino}phenoxy-N-phenylmethanimidic acid

Traditional Name

1-3-{[ethoxy(hydroxy)methylidene]amino}phenoxy-N-phenylmethanimidic acid

SMILES

CCOC(O)=NC1=CC(OC(O)=NC2=CC=CC=C2)=CC=C1

InChI Identifier

InChI=1S/C16H16N2O4/c1-2-21-15(19)18-13-9-6-10-14(11-13)22-16(20)17-12-7-4-3-5-8-12/h3-11H,2H2,1H3,(H,17,20)(H,18,19)

InChI Key

WZJZMXBKUWKXTQ-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
Phenoxy compound
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 homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:81733 )
Carbanilate herbicides (C18417 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Metabolic Pathways	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless and odorless powder.

Experimental Properties

Property	Value
Melting Point	120 ° C
Boiling Point	Not Available
Solubility	Practically insoluble in water (0.07 g/L at 20 °C)

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	2.54	ALOGPS
logP	5.12	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.34 m³·mol⁻¹	ChemAxon
Polarizability	30.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	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	splash10-004l-9740000000-2702126f25a7d0cb78b2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052r-1900000000-b610210faee8649eb07f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-000i-0900000000-2dcd41b8d9232793c063	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0ckl-5900000000-786d0a4094b1cba4c088	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0900000000-a3ca580c70151c9bdb61	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052r-2900000000-d3bee578fcce94a7ab89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0awl-7900000000-50b0cf4dd752afa5d83c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-000i-0900000000-93720309f9355a86ea96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000i-0900000000-5415a4e00c88da4b6140	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000i-0900000000-5605cff5c4e1feb31f80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0f80-0900000000-26d4dbcd4361aa31785d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-aeb44cefc56eb2417344	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0900000000-d458abc9e0cf96116d32	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0f80-0900000000-05609d2d4478c145a1f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-79e5d139dd99f808cb99	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-d4149a9c99c193be95fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001r-0900000000-a5e6c8b2202915651100	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0f79-0900000000-421678d6ccd8bd3552f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000i-0900000000-b9557bc3f57d4f124b8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001r-0900000000-6f432c97470339974197	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-4943000000-3fd4093da639e3680508	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-8960000000-c26de169b4253bbc54aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02fx-9520000000-a315f8835bc4cbb1219c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uxr-3690000000-a9d14dbb5e775161c3f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gbc-5960000000-48147b8c2835b8e0a2ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9610000000-13b3f0753c692c69e05b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-015c-9600000000-48cec14e9ec64efc8aef	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

Desmedipham 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: 9600 mg/kg (Rat, oral); LD50: >2000 mg/kg (Rabbits, transdermally)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Desmedipham is a selective, systemic post-emergence herbicide commonly used in beet and strawberry crops to protect against weeds, often in comination with Phenmedipham.

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

HMDB0251050

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID