Xylylcarb

HCID 17040CAS 2425-10-7

Basic information

Standard SMILES
CNC(=O)Oc1ccc(C)c(C)c1
InChIKey
WCJYTPVNMWIZCG-UHFFFAOYSA-N
Molecular formula
C10H13NO2
Average molar mass
179.22 g/mol
Monoisotopic mass
179.09462866

Overview

Xylylcarb is a carbamate ester. It has a role as an agrochemical, a carbamate insecticide and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is functionally related to a 3,4-xylenol and a methylcarbamic acid.

Names & identifiers

Preferred name
Xylylcarb
IUPAC
(3,4-dimethylphenyl) N-methylcarbamate
English name
MPMC
Molecular formula
C10H13NO2
Molecular weight
179.22

Names & synonyms

XylylcarbMPMCMeobal2425-10-73,4-Xylyl methylcarbamate3,4-Dimethylphenyl Methylcarbamate3,4-Dimethylphenyl N-methylcarbamatePhenol, 3,4-dimethyl-, methylcarbamateMethylcarbamic acid 3,4-xylyl esterCarbamic acid, methyl-, 3,4-xylyl ester3,4-DIMETHYLPHENOL METHYLCARBAMATEV 17004
Show more names
MPCMs1042MEOBARS-1046v17004
S 10422999840EDWCarbamic acid, N-methyl-, (3,4-dimethylphenyl) esterDTXSID3058032CHEBI:350483,4-dimethylphenylmethylcarbamateRefChem:904652DTXCID9031800

Database identifiers

CAS
2425-10-7
PubChem CID
17040
DTXSID
DTXSID3058032
ChEBI
CHEBI:35048
UNII
2999840EDW
EC Number
219-364-9
Nikkaji
J3.027I

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
38.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
13

Experimental & physicochemical properties

SpringerMaterials PropertiesFusion temperature
LogP2.25

Physicochemical properties

Melting point
79.1 °C · 79.1°C
Boiling point
311.75 °C · 311.75°C (rough estimate)
Density
1.1248 · 1.1248 (rough estimate)
vapor pressure
70 x · 70 x 10-3 Pa (20 °C)
refractive index
1.515 · 1.5150 (estimate)
Water Solubility
580 mg · 580 mg l-1 (20 °C)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Hazard information

Hazard Classes and Categories · 4 items

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 3

Acute Tox. 4 *

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 RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Xylylcarb 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

tsca
TSCA listed
Toxicity
LD50 oral in rat: 290mg/kg
risk_code
22-50/53
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn,N

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

UsesXylylcarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
General Manufacturing InformationPhenol, 3,4-dimethyl-, 1-(N-methylcarbamate): INACTIVE

Applications

DescriptionXylylcarb (MPMC) is a colorless solid, which is sparingly soluble in water and is fairly soluble in acetonitrile, cyclohexane, and xylene.

UsesXylylcarb is a non-systemic insecticide. It is mainly used to control hoppers and other sucking pests on rice, and leafhoppers, planthoppers and scale insects on fruit.

Suppliers11 total

上海稳同科技有限公司02151600108 13062666369 · [email protected]
河北贞佳新材料有限公司0319-5925599 13315915972
山东小野化学股份有限公司0539-6362799 20)
山东辉璟生物医药科技有限公司15192151674 · [email protected]
常州阿桑奇科技有限公司18961267976 · [email protected]

Additional notes

DefinitionChEBI: Xylylcarb is a carbamate ester. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide and an agrochemical. It is functionally related to a methylcarbamic acid and a 3,4-xylenol.

Related reactions

1 records

Linked notes

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