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({[(2,4-Dimethyl-1,3-dithiolan-2-yl)methylidene]amino}oxy)(methylamino)methanone

HCID 33507
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Basic information

CAS
26419-73-8
Standard SMILES
CNC(=O)ON=CC1(C)SCC(C)S1
InChIKey
GHFMMRFMDHDOBP-UHFFFAOYSA-N
Molecular formula
C8H14N2O2S2
Average molar mass
234.3 g/mol
Monoisotopic mass
234.04967004

Overview

2,4-Dimethyl-1,3-dithiolane-2-carboxaldehyde O-(methylcarbamoyl)oxime 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. (L795)

Names & identifiers

Preferred name
({[(2,4-Dimethyl-1,3-dithiolan-2-yl)methylidene]amino}oxy)(methylamino)methanone
IUPAC
[(2,4-dimethyl-1,3-dithiolan-2-yl)methylideneamino] N-methylcarbamate
English name
[(2,4-dimethyl-1,3-dithiolan-2-yl)methylideneamino] N-methylcarbamate
Molecular formula
C8H14N2O2S2
Molecular weight
234.34

Names & synonyms

SCHEMBL11246586Q7809268({[(2,4-Dimethyl-1,3-dithiolan-2-yl)methylidene]amino}oxy)(methylamino)methanoneMBR-6168ENT-276963M MBR-61682,4-Dimethyl-1,3-dithiolane-2-carbaldehyde O-(methylcarbamoyl)oxime((2,4-DIMETHYL-1,3-DITHIOLANE-2-YL)METHYLENE)AMINOMETHYLCARBAMICACID[(2,4-dimethyl-1,3-dithiolan-2-yl)methylideneamino] N-methylcarbamate1,3-Dithiolane-2-carboxaldehyde,2,4-dimethyl-O-[(methylamino)-carbonyl]oximeCarbamic acid, methyl-, O-(((2,4-dimethyl-1,3-dithiolan-2-yl)methylene)amino)-

Database identifiers

CAS
26419-73-8
PubChem CID
33507
DTXSID
DTXSID3042475

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
101 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
3
Heavy atoms
14
Formal charge
0
Complexity
247

Physicochemical properties

Density
1.3345 · 1.3345 (rough estimate)
refractive index
1.63 · 1.6300 (estimate)
pka
13.558 · 13.558±0.46(predicted)
FDA UNII
8 W03WH1E76 · 8W03WH1E76
EPA Substance Registry System
Tirpate (26419-73-8)
RIDADR
2757 · 2757
HazardClass
6.1 · 6.1(a)
PackingGroup
I
Hazardous Substances Data
26419 · 26419-73-8(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 1mg/kg

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

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.

Health Effects · 1 item

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 (A15321).

Exposure Routes

Chemistry & industry

Pharmacology

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Uses & manufacturing

Uses2,4-Dimethyl-1,3-dithiolane-2-carboxaldehyde O-(methylcarbamoyl)oxime is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Applications

General DescriptionA solid. Used as a nematocide. Manufacture discontinued.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Inhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

2,4-Dimethyl-1,3-dithiolane-2-carboxaldehyde O-(methylcarbamoyl)oxime 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.

Signs and Symptoms · 1 item

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. (L795)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

ridadr
2757
Toxicity
LD50 oral in rat: 1mg/kg
hazard_class
6.1(a)
packing_group
I
Hazardous Substances Data
26419-73-8(Hazardous Substances Data)