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N-メチルカルバミン酸3-SEC-アミルフェニル

m-(1-Methylbutyl)phenyl methylcarbamate

HCID 16787
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
2282-34-0
標準SMILES
CCCC(C)c1cccc(OC(=O)NC)c1
InChIKey
LHTOXQCYXYXXEZ-UHFFFAOYSA-N
分子式
C13H19NO2
平均分子量
221.29 g/mol
単同位体質量
221.14157885

概要

3-(1-Methylbutyl)phenyl N-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)

名称と識別子

優先名称
m-(1-Methylbutyl)phenyl methylcarbamate
IUPAC
(3-pentan-2-ylphenyl) N-methylcarbamate
現地名
N-メチルカルバミン酸3-SEC-アミルフェニル
英語名
3-sec-AMylphenyl N-MethylcarbaMate
分子式
C13H19NO2
分子量
221.29546

名称と別名

2282-34-03-sec-Amylphenyl N-methylcarbamateM-(1-METHYLBUTYL)PHENYL METHYLCARBAMATEChevron RE 5353Ortho 5,353Compound 5353Ortho RE-53533-(1-Methylbutyl)phenyl methylcarbamatem-sec-Amylphenyl N-methyl carbamateENT 27,127RE-5353OMS 227
名称をさらに表示
N-メチルカルバミン酸3-SEC-アミルフェニル3-(ペンタン-2-イル)フェニル N-メチルカルバマートメチルカルバミン酸3-(1-メチルブチル)フェニルN-メチルカルバミド酸3-(1-メチルブチル)フェニルPhenol, 3-(1-methylbutyl)-, 1-(N-methylcarbamate)
Phenol, 3-(1-methylbutyl)-, methylcarbamatePhenol, m-sec-pentyl-, methylcarbamateHSDB 2601Carbamic acid, methyl-, m-(1-methylbutyl)phenyl esterPhenol, m-(1-methylbutyl)-, methylcarbamateZV1MM336WBEPA Pesticide Chemical Code 059302BRN 2275572

データベース識別子

CAS
2282-34-0
PubChem CID
16787
DTXSID
DTXSID6042103
UNII
ZV1MM336WB

物性

構造計算による物性

XLogP
3.7
極性表面積
38.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
5
重原子数
16
形式電荷
0
複雑度
218

実験および物理化学的性質

PesticidesPesticides -> Carbamate Insecticides
Stability/Shelf Life · 2 件

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 · 2 件

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/

物理化学的性質

沸点
362.36 °C · 362.36°C (rough estimate)
比重(密度)
1.0451 · 1.0451 (rough estimate)
屈折率
1.5175 · 1.5175 (estimate)
溶解性
DMSO (Slightly), Methanol (Slightly)
外見
Solid
色
White to Off-White
EPAの化学物質情報
m-(1-Methylbutyl)phenyl methylcarbamate (2282-34-0)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

危険有害性情報

Hazards Summary · 1 件

A cholinesterase inhibitor; Toxic if ingested or absorbed through the skin; [HSDB] Effects in high-dose animal studies include convulsions and spastic paralysis; [RTECS] See m-(1-Ethylpropyl)phenyl methylcarbamate. See CARBAMATE INSECTICIDES.

安全と保護具

Exposure Control and Personal Protection · 1 件

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]

毒性情報

Treatment · 1 件

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 件

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)

化学と産業

薬理情報

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

用途と製造

Uses · 4 件

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; [HSDB]

Farming (Pesticides) [Category: Industry]

FORMERLY IN SOIL INSECTICIDE BUX FOR CORN ROOTWORMS, RICE WATER WEEVILS, & ON OTHER FIELD CROPS

3-(1-Methylbutyl)phenyl N-methylcarbamate is a component of Bufencarb, a widely used insecticide or pesticide in homes, gardens and agricultural applications.

U.S. Exports · 2 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production(1975) NONE
Consumption Patterns(BUX, A 3:1 MIXTURE OF M-(1-METHYLBUTYL)PHENYL METHYLCARBAMATE WITH M-(1-ETHYLPROPYL)PHENYL METHYLCARBAMATE): FORMERLY, 99% AS A SOIL INSECTICIDE FOR CORN ROOTWORMS ON CORN; 1% ON RICE FOR RICE WATER WEEVILS AND ON OTHER FIELD CROPS (1971)
Methods of ManufacturingFORMERLY BY THE REACTION OF 3-(1-METHYLBUTYL)PHENOL WITH METHYL ISOCYANATE
Formulations/Preparations · 3 件

CHEVRON RE 5353; ENT 27,127; OMS 227; ORTHO 5,353; RE 5353

ORTHO RE-5353; BUFENCARB; BUX; BUX TEN

Bux Ten Granular, granules (100 mg ai/kg); Bux 2 Emulsive, ec (240 g/L); Bux 360 Emulsive, ec (360 g/L); dusts (20 and 40 g/kg) /bufencarb/

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
Nikkaji
J42.909K
Ecotoxicity Values · 5 件

LC50 Japanese quail oral more than 5000 ppm in 5-day diet (8% mortality at 2236 ppm, 42% at 5000 ppm) /bux/

LC50 Ring-necked pheasants oral more than 5000 ppm in 5-day diet (no mortality to 5000 ppm) /bux/

LC50 Mallards oral more than 5000 ppm in 5-day diet (12% mortality at 1000 ppm, 38% at 5000 ppm) /bux/

LD50 Mallards oral 10.5 mg/kg, 3-4 month old females (95% confidence limit 8.84-12.5 mg/kg) /68.9%, bufencarb/

For more Ecotoxicity Values (Complete) data for M-(1-METHYLBUTYL)PHENYL METHYLCARBAMATE (10 total), please visit the HSDB record page.

Environmental Fate · 2 件

TERRESTRIAL FATE: IT IS UNLIKELY THAT BUX WILL CAUSE LONG-TERM ENVIRONMENTAL CONTAMINATION.

Terrestrial fate: It is degraded fairly rapidly in soil and no carry-over would be expected from one season to the next with granules. /bufencarb/

Adverse EffectsOther Poison - Carbamate
Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 件

3-(1-Methylbutyl)phenyl N-methylcarbamate 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 件

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)

Human Toxicity Excerpts · 2 件

Symptomatology: 1. Nausea, vomiting, abdominal cramps, diarrhea & excessive salivation...sweating. 2. Lassitude & weakness. 3. Rhinorrhea and sensation of tightness in chest may occur with inhalation exposure. 4. Blurring or dimness of vision. Miosis...tearing, ciliary muscle spasm, loss of accommodation and ocular pain. None of these...signs...is dependable for diagnosis. Mydriasis may be seen... 5. Loss of muscle coordination, slurring of speech, fasciculation & twitching of muscles. 6. Difficulty in breathing, excessive secretions of saliva and of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi, and hypertension. 7. ...jerky movements, incontinence, convulsions and coma. 8. Death...due to resp arrest of central origin, paralysis of resp muscles, intense bronchoconstriction or all three. /Carbaryl/

Four spraymen and one mixer applied 6 to 7 pump charges of bufencarb during the first day and 9 to 10 pump charges during the second day... One sprayman complained of "hunger cramps" in his stomach...the same sprayman and another one reported that they had vomited... Cholinesterase activity was depressed to about 50% of normal... During the second day one sprayman vomited while at work... His pulse rate was 52 per min and he experienced some sweating, dizziness, and pupillary change. /bufencarb/

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 4 件

Toxic if ingested or absorbed through the skin, it inhibits cholinesterase activity in red blood cells. /bufencarb/

Very toxic to fish. Causes a variety of teratogenic effects in chick eggs when injected into the yolk sac. /bufencarb/

/Acute oral toxicity in birds/ Ataxia, dyspnea, wing-drop, tremors, regurgitation, ptosis, and wing-beat convulsions or tetany. Signs appeared as soon as 15 min and mortalities usually occurred between 20 min and 1 hr after treatment. /bufencarb/

NITROSO DERIV OF THE TESTED METHYL CARBAMATE INSECTICIDES, INCL BUX-TEN, ARE POTENT MUTAGENS, BUT PARENT INSECTICIDES ARE NON-MUTAGENIC.

Environmental Abiotic Degradation · 2 件

May decomp when exposed to sunlight. /bufencarb/

M-(1-METHYLBUTYL)-PHENYL METHYLCARBAMATE RAPIDLY DEGRADED IN WATER. MOST OF METABOLITES WERE PRESENT AS CONJUGATES OR OTHER POLAR METABOLITES.

安全データ

毒性
LD50 orl-rat: 87 mg/kg 28ZEAL 5,31,76
有毒物質データの
2282-34-0(Hazardous Substances Data)
General Manufacturing Information · 4 件

The common name bufencarb is...for a reaction product... The insecticidally active components of the product...are: 3-(1-methylbutyl)phenyl methylcarbamate...and...3-(1-ethylpropyl)phenyl methylcarbamate... /bufencarb/

The technical product consists of approx 65% of a 3:1 mixture of 3-(1-methylbutyl)phenyl methylcarbamate and 3-(1-ethylpropyl)phenyl methylcarbamate and 35% of structurally related inactive material comprised mainly of p and o isomers. /bufencarb/

Bufencarb has been suggested as a common name for the mixture for which BUX long has been a trade name. /bufencarb/

BUFENCARB IS ACTIVE, AT RATES OF 0.5-2.0 KG AI/HA, AGAINST A RANGE OF SOIL & FOILAGE INSECTS, PARTICULARLY...CORN ROOTWORM LARVAE, RICE STEM BORERS, RICE GREEN LEAFHOPPER, RICE WATER WEEVIL, RICE PLANTHOPPERS & PINEAPPLE ROOT MEALBUG. /BUFENCARB/

応用分野

使用3-sec-Amylphenyl N-Methylcarbamate is a component of the carbamate insecticide Bufencarb (B689385).

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