ContaminantDB: Methomyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:04 UTC

Update Date

2026-03-27 02:15:58 UTC

Accession Number

CHEM000844

Identification

Common Name

Methomyl

Class

Small Molecule

Description

Methomyl is a carbamate pesticide. Methomyl is an Agricultural insecticide and nematocide. Methomyl belongs to the family of Carbamic Acids. These are compounds containing the carbamic acid structure.

Contaminant Sources

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

Contaminant Type

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

Chemical Structure

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

Synonyms

Value	Source
1-(Methylthio)acetaldehyde O-methylcarbamoyloxime	HMDB
1-(Methylthio)ethylideneamino methylcarbamate	HMDB
2-Methylthio-acetaldehyd-O-(methylcarbamoyl)-oxim	HMDB
2-Methylthio-acetaldehyd-O-(methylcarbamoyl)-oxime	HMDB
2-Methylthio-propionaldehyd-O-(methylcarbamoyl)-oxim	HMDB
3-Thiabutan-2-one, O-(methylcarbamoyl)oxime	HMDB
Acetimidothioic acid, methyl-, N-(methylcarbamoyl) ester	HMDB
Du pont 1179	HMDB
Du pont insecticide 1179	HMDB
Dupont 1179	HMDB
Flytek	HMDB
Insecticide 1,179	HMDB
Insecticide 1179	HMDB
Kipsin	HMDB
Lannabait	HMDB
Lannate	HMDB
Lannate 20	HMDB
Lannate L	HMDB
Lannate LB	HMDB
Lannate LV	HMDB
Lannate(R)	HMDB
Lanox	HMDB
Lanox 216	HMDB
LANOX 90	HMDB
Memilene	HMDB
Mesomile	HMDB
Methavin	HMDB
Methomex	HMDB
Methomyl (lannate)	HMDB
Methomyl 5g	HMDB
Methomyl lannate	HMDB
Methyl (1E)-N-([(methylamino)carbonyl]oxy)ethanimidothioate	HMDB
Methyl N-(((methylamino)carbonyl)oxy)ethanimidothioate	HMDB
Methyl N-((methylcarbamoyl)oxy)thioacetimidate	HMDB
Methyl N-(methylcarbamoyloxy)ethanimidothioate	HMDB
Methyl N-[(methylcarbamoyl)oxy]thioacetimidate	HMDB
Methyl N-[[(methylamino)carbonyl]oxy]ethanimidothioate, 9ci	HMDB
Methyl O-(methylcarbamoyl)thiolacethohydroxamate	HMDB
Methyl O-(methylcarbamoyl)thiolacetohydroxamate	HMDB
Methyl O-(methylcarbamyl)thiolacetohydroxamate	HMDB
Metomil	HMDB
N-((Methylcarbamoyl)oxy)thioacetimidic acid methyl ester	HMDB
N-[(Methylcarbamoyl)oxy]thioacetimidic acid methyl ester	HMDB
N-[[(Methylamino)carbonyl]oxy]-2-(methylthio)ethanimine	HMDB
Nu-bait II	HMDB
Nudrin	HMDB
S-Methyl N-(methylcarbamoyloxy)thioacetimidate	HMDB
S-Methyl N-[[(methylamino)carbonyl]oxy]ethanimidothioate	HMDB
Sorex golden fly bait	HMDB
Thiobutan-2-one, O-(methylcarbamoyl)oxime	HMDB
20, Lannate	HMDB

Chemical Formula

C₅H₁₀N₂O₂S

Average Molecular Mass

162.210 g/mol

Monoisotopic Mass

162.046 g/mol

CAS Registry Number

16752-77-5

IUPAC Name

(E)-[(methyl-C-hydroxycarbonimidoyl)oxy][1-(methylsulfanyl)ethylidene]amine

Traditional Name

lannate LV

SMILES

CS\C(C)=N\OC(O)=NC

InChI Identifier

InChI=1S/C5H10N2O2S/c1-4(10-3)7-9-5(8)6-2/h1-3H3,(H,6,8)/b7-4+

InChI Key

UHXUZOCRWCRNSJ-QPJJXVBHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Not Available

Direct Parent

Carboximidic acids and derivatives

Alternative Parents

Substituents

Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Carboximidic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Carbamate pesticides (C11196 )
Carbamate insecticides (C11196 )

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	78 - 79°C
Boiling Point	Not Available
Solubility	58 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	2.76 g/L	ALOGPS
logP	1.07	ALOGPS
logP	1.54	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	1.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.18 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	40.78 m³·mol⁻¹	ChemAxon
Polarizability	16.35 Å³	ChemAxon
Number of Rings	0	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	splash10-052b-9200000000-08a2425520720fc4ddeb	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006t-9200000000-e336671b45724f2223f8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00y0-9700000000-fb58e6c723ee86fa0521	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9500000000-bc37fefdbd44b78215b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9500000000-c048d4fb7391b51e8092	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9500000000-b6e2ca797273130b4579	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9300000000-7208ae44a68a6aefb55a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9200000000-a3d913d869d143089c32	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05g0-9100000000-ef272eaa6dee90335521	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9600000000-f23a2fc883ac3c1eec87	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9500000000-b725712ec0d1c8f22d6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9500000000-6c16bc52b03ec9f35248	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9400000000-58a29283a18ff87fed94	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052r-9200000000-db11172c09d336f4352b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05g0-9000000000-c800429b256376d754ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00y0-9800000000-e1b10436e09d20202a33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-05g0-9100000000-ef272eaa6dee90335521	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052r-9200000000-a3d913d869d143089c32	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-052r-9500000000-dbe88752e49f586980ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-052r-9500000000-a30a2ae7d641e550cec1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052r-9200000000-db11172c09d336f4352b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9800000000-28c1600c0ec8ebe5185f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-a24d6210888235a5f3dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-4aa2ee0cb39b1280c11e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-4900000000-c24b0468dccb53bcd16b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9100000000-c487f2a68e3df2908ea3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00gm-9000000000-3c743531b809e60da5c1	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9300000000-52e81fc7bc39a7bd7ad4	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	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	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

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

Methomyl 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: 10 mg/kg (Oral, Mouse) (4) LD50: 9 mg/kg (Subcutaneous, Rat) (4) LC50: 0.45 mg/kg over 4 hours (Inhalation, Rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Methomyl 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

HMDB0031804

FooDB ID

FDB008477

Phenol Explorer ID

Not Available

KNApSAcK ID