Basic information
- CAS
672-04-8- Standard SMILES
CCC(CC)c1cccc(OC(=O)NC)c1- InChIKey
SMSFWBAOKCZZBF-UHFFFAOYSA-N- Molecular formula
- C13H19NO2
- Average molar mass
- 221.29 g/mol
- Monoisotopic mass
- 221.14157885
Overview
3-(1-Ethylpropyl)phenyl methylcarbamate is a component of Bufencarb, 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
- M-(1-Ethylpropyl)phenyl methylcarbamate
- IUPAC
- (3-pentan-3-ylphenyl) N-methylcarbamate
- English name
- 3-(1-Ethylpropyl)phenyl MethylcarbaMate
- Molecular formula
- C13H19NO2
- Molecular weight
- 221.3
Names & synonyms
672-04-8M-(1-ETHYLPROPYL)PHENYL METHYLCARBAMATE3-(1-Ethylpropyl)phenyl Methylcarbamate(3-pentan-3-ylphenyl) N-methylcarbamateXKB1UJJ0WL3-(pentan-3-yl)phenyl N-methylcarbamateCarbamic acid, methyl-, m-(1-ethylpropyl)phenyl esterPhenol, m-(1-ethylpropyl)-, methylcarbamateUNII-XKB1UJJ0WLHSDB 25893-(1-Ethylpropyl)phenol 1-(N-Methylcarbamate); Methylcarbamic Acid m-(1-Ethylpropyl)phenyl Ester; m-(1-Ethylpropyl)phenol Methylcarbamate; m-(1-Ethylpropyl)phenyl Methylcarbamate;Phenol, 3-(1-ethylpropyl)-, methylcarbamate
Show more names
3-(3-Pentanyl)phenyl methylcarbamatePhenol, 3-(1-ethylpropyl)-, 1-(N-methylcarbamate)
SCHEMBL5933894DTXSID1042102SCHEMBL305198443-(pentan-3-yl)phenyl methylcarbamate3-(1-ethylpropyl) phenylmethyl carbamateDB-303681NS00005303M-(1-ETHYLPROPYL)PHENYL METHYLCARBAMATE [HSDB]
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 38.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 214
Experimental & physicochemical properties
PesticidesPesticides -> Carbamate Insecticides
Stability/Shelf Life
It is stable in neutral or acid soln, but the rate of hydrolysis incr with rise in either pH or temp. /bufencarb/
May decomp when exposed to sunlight; moderate to low volatility /bufencarb/
Other Experimental Properties
Colorless, low melting solid; MP: 40-45 °C; density: 1.031 at 25 °C; BP: 125-130 °C at 0.1 mm Hg; moderate to low volatility; solubility in water is less than 0.01%; soluble in most solvents but less in aliphatic hydrocarbons /bufencarb/
A low melting solid, yellow to amber in color; MP: 26-39 °C; vapor pressure: 3x10-5 mm Hg at 30 °C; BP: about 125 °C at 0.04 mm Hg; density: 1.024 at 26 °C /bufencarb, technical product/
Physicochemical properties
- FDA UNII
- 1 UJJ0WL · XKB1UJJ0WL
- EPA Substance Registry System
- m-(1-Ethylpropyl)phenyl methylcarbamate (672-04-8)
- Hazardous Substances Data
- 672 · 672-04-8(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards SummaryA cholinesterase inhibitor; Toxic if ingested or absorbed through the skin; [HSDB] See m-(1-Methylbutyl)phenyl methylcarbamate. See CARBAMATE INSECTICIDES.
Safety & protection
Exposure Control and Personal Protection
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
Toxicology
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.
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. (A15321)
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
Uses
Formerly used as a soil insecticide; A major component of Bufencarb; Bufencarb, trade name BUX, is a 3:1 mixture with 65% m-(1-Methylbutyl)phenyl methylcarbamate and m-(1-Ethylpropyl)phenyl methylcarbamate plus 35% structurally related inactive isomers; No longer commercially produced in the US; [HSDB]
Farming (Pesticides) [Category: Industry]
FORMERLY IN SOIL INSECTICIDE BUX FOR CORN ROOTWORMS, WATER WEEVILS, & ON OTHER FIELD CROPS
3-(1-Ethylpropyl)phenyl methylcarbamate is a component of Bufencarb, a widely used insecticide or pesticide in homes, gardens and agricultural applications.
U.S. Exports
(1972) No Data
(1975) No Data
U.S. Imports
(1972) No Data
(1975) No Data
U.S. Production(1975) NONE
Consumption Patterns(BUX, A 1:3 MIXTURE OF M-(1-ETHYLPROPYL)PHENYLMETHYLCARBAMATE WITH M-(1-METHYLBUTYL)PHENYL METHYLCARBAMATE): FORMERLY, 99% AS A SOIL INSECTICIDE FOR CORN ROOTWORMS ON CORN; 1% ON RICE FOR RICE WATER WEEVILS & ON OTHER FIELD CROPS (1971)
Methods of ManufacturingFORMERLY BY REACTION OF M-(1-ETHYLPROPYL)PHENOL WITH METHYL ISOCYANATE
Formulations/Preparations
ORTHO RE-5353; BUFENCARB; BUX; BUX TEN
Bux Ten Granular, granules (100 mg ai/kg); Bux 2 Emulsive, emulsifiable concentrate (240 g/L); Bux 360 Emulsive, emulsifiable concentrate (360 g/L); dusts (20 and 40 g/kg) /bufencarb/
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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