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Butacarb

HCID 17564
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
2655-19-8
Standard-SMILES
CNC(=O)Oc1cc(C(C)(C)C)cc(C(C)(C)C)c1
InChIKey
SLZWBCGZQRRUNG-UHFFFAOYSA-N
Summenformel
C16H25NO2
Durchschnittliche Molmasse
263,37 g/mol
Monoisotopische Masse
263,18852904

Überblick

Butacarb is an alkylbenzene.

Namen und Bezeichner

Bevorzugter Name
Butacarb
IUPAC
(3,5-ditert-butylphenyl) N-methylcarbamate
Englischer Name
(3,5-ditert-butylphenyl) N-methylcarbamate
Summenformel
C16H25NO2
Molmasse
263.38

Namen und Synonyme

BUTACARBButacarbeCaswell No. 291B3,5-Di-tert-butylphenyl methylcarbamate2655-19-83,5-Di-tert-butylphenyl N-methylcarbamate3,5-Di-t-butylphenylmethylcarbamateBTS 14639RD 1463948SLE5Y1183,5-Bis(1,1-dimethylethyl)phenol methylcarbamateCarbamic acid, methyl-, 3,5-di-tert-butylphenyl ester
Weitere Namen anzeigen
RD14639BTS-14639Carbaryl Impurity 18(3,5-ditert-butylphenyl) N-methylcarbamatePhenol, 3,5-bis(1,1-dimethylethyl)-, 1-(N-methylcarbamate)N-Methylcarbamic acid 3,5-bis(1,1-dimethylethyl)phenyl ester
Phenol, 3,5-bis(1,1-dimethylethyl)-, methylcarbamateDTXSID0041690RefChem:121962DTXCID8021690Butacarb [ISO]Butacarbe [French]Butacarb [ISO:BSI]HSDB 2799

Datenbank-Bezeichner

CAS
2655-19-8
PubChem CID
17564

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,7
Polarare Oberfläche (TPSA)
38,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
19
Formalladung
0
Komplexität
290

Experimentelle und physikochemische Eigenschaften

PesticidesPesticides -> Carbamate Insecticides
LogPlog Kow = 4.99 /Estimated/
Color/FormWHITE CRYSTALLINE SOLID
Solubility · 2 Einträge

Sol in most org solvents; sparingly in petroleum ether

In water, 15 mg/L at 25 °C

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point97-99 °C
Vapor Pressure · 2 Einträge

0.0000888 [mmHg]

1.98X10-6 mm Hg at 20 °C

Henry's Law ConstantHenry's Law constant = 4.6X10-8 atm-cu m/mol at 25 °C /Estimated/
Physical DescriptionWhite solid; [HSDB]
Stability/Shelf LifeStable to light, heat and hydrolysis under normal conditions

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Gefahrenhinweise

Hazards SummarySee CARBAMATE INSECTICIDES.
Shipment Methods and Regulations · 3 Einträge

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Shipping Name/ Number DOT/UN/NA/IMO · 5 Einträge

IMO 6.1; Carbamate pesticides, solid, toxic, nos; carbamate pesticides, liquid, toxic, flammable, nos, flashpoint between 23 °C and 61 °C; carbamate pesticides, liquid, toxic, nos; carbamate pesticides, liquid, NOS

IMO 3.2; Carbamate pesticides, liquid, flammable, toxic, nos, flashpoint less than 23 °C

UN 2757; Carbamate pesticides, solid, toxic, nos; carbamate pesticides, liquid, nos

UN 2758; Carbamate pesticides, liquid, flammable, toxic, nos, flashpoint less than 23 °C

For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for BUTACARB (6 total), please visit the HSDB record page.

Skin, Eye, and Respiratory Irritations · 1 Eintrag

Carbamates produce slight to moderate skin and eye irritation, depending on the vehicle used, duration of contact, and on whether the substance is applied to the abraided or intact skin. From the available data, it cannot be excluded that some of the carbamates will have a slight to moderate sensitization potential. /Carbamate Pesticides/

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 3 Einträge

The carbamates alone weakly activated estrogen- or progesterone-responsive reporter genes in breast and endometrial cancer cells. All of the carbamates decreased estradiol- or progesterone-induced reporter gene activity in the breast and endometrial cancer cells. In whole cell competition binding assays, the carbamates demonstrated a limited capacity to displace radiolabeled estrogen or progesterone from /estrogen receptor/ or /progesterone receptor/. /Carbamates/

Carbamates are effective insecticides by virtue of their ability to inhibit acetylcholinesterase (AChE) in the nervous system. They also inhibit other esterases. The carbamylation of the enzyme is unstable, and the regeneration of AChE is relatively rapid compared with that from a phosphorylated enzyme. Thus, carbamate pesticides are less dangerous with regard to human exposure than organophosphorus pesticides. The ratio between the dose required to produce death and the dose required to produce minimum symptoms of poisoning is substantially larger for carbamate compounds than for organophosphorus compounds. /Carbamate Pesticides/

The carbamate insecticides are reversible cholinesterase-inhibitors. They cause this effect by reversible carbamylation of the enzyme acetylcholinesterase, allowing accum of acetylcholine, as with the organophosphate insecticides. ... While the organophosphate insecticides cause irreversible inhibition of the cholinesterase enzymes, the carbamyl-enzyme complex is reversible & dissociates far more readily than the organophosphate complex. The clinical syndrome is more benign & of much shorter duration with the carbamate insecticides. /Carbamate insecticides/

Metabolism/Metabolites · 5 Einträge

When butacarb was incubated with mouse liver 10,000xg supernatant, eleven metabolites were detected. Hydrolysis produced only 6 phenols. One of these, the major metabolite, was identified as 3,5-di-tert-butylphenol. Other metabolites were characterized but not all were completely identified: two acid metabolites containing a carboxyl & carbamoyl group; two containing a carbamoyl & two hydroxy groups (but not dihydroxybenzenoid); a hydroxybutylphenol; one containing a carbamoyl & hydroxy group; two dihydroxybutylphenols; n-hydroxymethyl butacarb; & n-hydroxymethyl hydroxybutyl analog. Studies with housefly (musca domestica), blowfly (lucilia sericata) & grass grubs (costelytra zealandica) gave results quant similar to those with mouse liver enzymes.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
DTXSID
DTXSID0041690
ChEBI
CHEBI:82089
UNII
48SLE5Y118
Nikkaji
J7.642B
Other Experimental PropertiesHydroxyl radical reaction rate constant: 15X10-12 cu cm/molec-sec at 25 °C /Estimated/

Physikochemische Eigenschaften

Schmelzpunkt
102.9 °C · 102.9°C
Siedepunkt
406.62 °C · 406.62°C (rough estimate)
Dichte
0.9903 · 0.9903 (rough estimate)
Brechungsindex
1.4909 · 1.4909 (estimate)
pka
12.39 · 12.39±0.46(Predicted)
Wasserlöslichkeit
15 mg/L · 15mg/L(20 ºC)
Henry's Law Constant
2.2 · 2.2×102 mol/(m3Pa) at 25℃, HSDB (2015)
EPA chemische Informationen
Butacarb (2655-19-8)

Sicherheit und Schutzausrüstung

Exposure Control and Personal Protection · 1 Eintrag

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]

Storage ConditionsStore in cool, dry place away from feed and food.
Disposal Methods · 1 Eintrag

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 5 Einträge

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

The protective clothing should be kept in separate places where it cannot be contaminated with toxic chemicals. It should be forbidden to keep this clothing in living quarters. Protective clothing must be washed at least once a week and each time it is contaminated with pesticides. Before washing the clothing should be soaked for several hours in a calcium carbonate solution. /Pesticides/

Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/

Personal Protective Equipment (PPE)Approved respirator. chemical resistant footwear plus socks. Long-sleeved shirts and long pants. Waterproof gloves.

Toxikologische Informationen

Treatment · 1 Eintrag

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.

Interactions · 1 Eintrag

...Feature of insecticidal action of... carbamates is pronounced synergism shown by addition of methylenedioxy compound such as piperonyl butoxide, sesoxane, and propyl isome... these prevent in vivo detoxication of carbamates by inhibiting "mixed function oxidase" detoxification system. /Carbamates/

Health Effects · 1 Eintrag

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).

Ecotoxicity Values · 2 Einträge

LC50 Rasbora heteromorpha (Harlequinfish, red rasbora) 610 ug/L/24 hr; renewal /formulated product/

LC50 Rasbora heteromorpha (Harlequinfish, red rasbora) 580 ug/L/48 hr; renewal /formulated product/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 980(SRC), determined from a water solubility of 15 mg/L(2) and a regression-derived equation(3), indicates that butacarb is expected to have low mobility in soil(SRC). Volatilization of butacarb from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.6X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.98X10-6 mm Hg(4), and water solubility(2). Butacarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 980(SRC), determined from a water solubility of 15 mg/L(2) and a regression-derived equation(3), indicates that butacarb is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.57X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.98X10-6 mm Hg(4), and water solubility(2). According to a classification scheme(5), an estimated BCF of 130(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butacarb, which has a vapor pressure of 1.98X10-6 mm Hg at 25 °C(2) is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase butacarb is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 26 hours(SRC), calculated from its rate constant of 14X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase butacarb may be removed from the air by wet and dry deposition(SRC). Butacarb does not contain chromophores that absorb at wavelengths >290 nm and would not be expected to be susceptible to direct photolysis by sunlight(SRC).

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

Butacarb 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 Eintrag

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)

Soil Adsorption/Mobility · 1 Eintrag

The Koc of butacarb is estimated as 980(SRC), using a water solubility of 15 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that butacarb is expected to have low mobility in soil(SRC).

Human Toxicity Excerpts · 2 Einträge

/SIGNS AND SYMPTOMS/ Symptomatology: Nausea, vomiting, abdominal cramps, diarrhea & excessive salivation... sweating. Lassitude & weakness. Rhinorrhea and sensation of tightness in chest may occur with inhalation exposure. 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 ... Loss of muscle coordination, slurring of speech, fasciculation & twitching of muscles. Difficulty in breathing, excessive secretions of saliva and of respiratory tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi, and hypertension. ... Jerky movements, incontinence, convulsions and coma. Death ... due to respiratory arrest of central origin, paralysis of respiratory muscles, intense bronchoconstriction or all three.

/SIGNS AND SYMPTOMS/ The clinical picture of carbamates intoxication results from accumulation of ACh at nerve endings. ...The signs and symptoms can be categorized into the following 3 groups: (a) Muscarinic manifestations - increased bronchial secretion, excessive sweating, salivation, and lachrymation; pinpoint pupils, bronchoconstriction, abdominal cramps (vomiting and diarrhea); and bradycardia. (b) Nicotinic manifestations - fasciculation of fine muscles (in severe cases, diaphragm and respiratory muscles also involved); and tachycardia. (c) Central nervous system manifestations- headache, dizziness, anxiety, mental confusion, convulsions, and coma; and depression of respiratory center. All these signs and symptoms can occur in different combinations and can vary in onset and sequence, depending on the chemical, dose, and route of exposure. The duration of symptoms is usually shorter than that observed in organophosphorus poisoning. Mild poisoning might include muscarinic and nicotinic signs only. Severe cases always show central nervous system involvement; the clinical picture is dominated by the respiratory failure sometimes leading to pulmonary edema due to the combination of the above mentioned symptoms. /Carbamate pesticides/

Artificial Pollution SourcesButacarb's former production may have resulted in its release to the environment through various waste streams; its former use as a cholinesterase inhibitor insecticide(1) resulted in its direct release to the environment.

Sicherheitsdaten

Giftige Stoffe Daten
2655-19-8(Hazardous Substances Data)

...Butacarb.../is/ cleaved to phenolic products by enzyme system in liver microsomes, which requires nadph & is inhibited by carbon monoxide...it is likely that this...microsomal mono-oxygenation is very important in 'hydrolysis' of carbamates.

The principal route of metabolism of insecticidal carbamate esters is oxidative and is generally associated with the mixed-function oxidase (MFO) enzymes, which are present in several tissues. /Carbamate pesticides/

The metabolism of 3,5-di-tert-butylphenyl-N-methylcarbamate (butacarb) was studied in insects and mouse liver enzymes. Tritium (H-3) labeled butacarb was incubated with 10,000 times the force of gravity supernatants from mouse liver or housefly and blowfly enzyme preparations, obtained from their abdomens. The reaction mixtures were analyzed for metabolites. Eleven oxidation products were detected in each species. In-vivo, adult houseflies and blowflies were dosed topically with H-3 labeled butacarb. The insects were then extracted by grinding them with sand and ether. Ether extracts were examined for metabolites. The water soluble fraction was also examined. Both fractions consisted of complex mixtures. The ether fraction was hydrolyzed with sodium-hydroxide, and the water soluble portion was analyzed. Six phenolic metabolites were detected. The major phenolic product was 3,5-di-tert-butylphenol, which accounted for more than half of the dose.

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

Absorption, Distribution and Excretion · 2 Einträge

In vivo studies have shown that carbamates are almost completely absorbed during normal transit through the gastrointestinal tract. ...In mice, all carbamates were rapidly distributed to the tissues and organs. The half-life values of penetration ranged from 8-17 min for carbamates. ...In animals, oxidation of carbamates often, but not always, results in detoxification. Oxidative metabolism generally leads to products of greater polarity and water solubility, and these can be more readily eliminated through the urine and feces than the parent compound. /Carbamate pesticides/

Little information is available on the distribution of carbamates in the various organs and tissues in mammals following exposure by inhalation or the oral route. The organs in which residues have been reported are the liver, kidneys, brain, fat, and muscle. The half-life in the rat is of the order of 3-8 hr. It seems that the excretion of carbamates via urine is also rapid in man, and that the metabolic pathways in man are the same as those in the rat. /Carbamate pesticides/

Verwendung und Herstellung

Uses · 6 Einträge

Used as insecticide and to control blowfly larvae in sheep; Not marketed in the US; [HSDB]

Not currently registered with the EPA for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For butacarb (USEPA/OPP Pesticide Code: 291300) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Insecticide

... Mixture with gamma-HCH against animal ectoparasites.

Formulations/PreparationsEmulsifiable concentrate, granules
General Manufacturing Information · 5 Einträge

Very effective against larval stages of sheep blow fly. In sheep dips at 50 g ai/100 l gives protection from blow fly strike 10 to 12 weeks.

Compatible with most other pesticides

Not marketed in /United States/

FRASER, HARRISON, BRITISH PATENT 987,254 (1965 TO BOOTS PURE DRUG); KAEDING ET AL, J AGR FOOD CHEM 13, 215 (1965).

Discontinued by The Boots Co Ltd

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