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Dichlormate

HCID 16072
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1966-58-1
Standard SMILES
CNC(=O)OCc1ccc(Cl)c(Cl)c1
InChIKey
DSVOTYIOPGIVPP-UHFFFAOYSA-N
Molecular formula
C9H9Cl2NO2
Average molar mass
234.08 g/mol
Monoisotopic mass
233.0010339

Overview

Dichlormate 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
Dichlormate
IUPAC
(3,4-dichlorophenyl)methyl N-methylcarbamate
English name
3,4-dichlorobenzyl methylcarbamate
Molecular formula
C9H9Cl2NO2
Molecular weight
234.08

Names & synonyms

Dichlormate1966-58-13,4-DICHLOROBENZYL METHYLCARBAMATE3,4-SirmateDichlormate [ISO](3,4-dichlorophenyl)methyl N-methylcarbamateUC 22463XDA707PJIOBenzenemethanol, 3,4-dichloro-, methylcarbamate3,4-Dichlorobenzyl N-methylcarbamateBenzenemethanol, 3,4-dichloro-, 1-(N-methylcarbamate)Caswell No. 298A
Show more names
UC-224633,4-DichlormateN-Methylcarbamic acid 3,4-dichlorobenzyl ester
Caswell No. 301AMethylcarbamate 3,4-dichlorobenzyl esterEINECS 217-813-3UNII-XDA707PJIOEPA Pesticide Chemical Code 298200BRN 2215173Carbamic acid, N-methyl-, 3,4-dichlorobenzyl ester3,4-Dichlorbenzylester kyseliny methylkarbaminove [Czech]

Database identifiers

CAS
1966-58-1
PubChem CID
16072
DTXSID
DTXSID5041853
UNII
XDA707PJIO
EC Number
217-813-3

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
38.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
14
Formal charge
0
Complexity
201

Physicochemical properties

Melting point
52 °C · 52°C
Boiling point
139 °C · 139 °C(Press: 0.5 Torr)
Density
1.3564 · 1.3564 (rough estimate)
refractive index
1.61 · 1.6100 (estimate)
pka
12.45 · 12.45±0.46(Predicted)
Water Solubility
0.17 g/L · 0.17g/L(25 ºC)
FDA UNII
707 PJIO · XDA707PJIO
EPA Substance Registry System
Dichlormate (1966-58-1)

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

UsesDichlormate is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Suppliers17 total

杭州品高化工有限公司0571-87658025 · [email protected]
毕佳索(上海毕得医药科技股份有限公司)400-6005915 · [email protected]
北京索莱宝科技有限公司010-50973130 17801761073 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Alfa Chemistry+1-5166625404 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海林栎生物科技有限公司13761635123 · [email protected]
淮安海玻瑞恩医药研发有限公司

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Nikkaji
J7.832H
Inhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Dichlormate 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).
18114966287 · [email protected]
上海玉函化工有限公司021-61469567 13774476675 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
上海捷世凯生物科技有限公司021-57520305 13795461237 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +8619957148339 · [email protected]
江苏艾康生物医药研发有限公司17714375163 · [email protected]
合肥钼凯医药科技有限公司18001872185; 18001872185 · [email protected]