4-Benzothienyl methylcarbamate

207.25

207.25

8M3AR1XD9I

DTXSID0042161

White, crystalline solid

66.6 Ų

log Kow = 2.17 (est)

1.2784

129 °C

330.5±24.0 °C(Predicted)

1.5250 (estimate)

In water, 565 mg/L at 25 °C (est)|Greater than 20% soluble in dimethylsulfoxide, acetone, methylethyl ketone, toluidine, triethylene glycol, acetonitrile, dioxane, and methylene chloride; greater than 10% soluble in ethanol, ethyl acetate, ethylene glycol, propanol, and methanol; greater than 5% soluble in benzene and isobutanol; greater than 1% soluble in carbon tetrachloride, glycerin, toluene, and xylene; less than 0.1% soluble in kerosene, heptane, and water

5.28X10-5 mm Hg at 25 °C (est)

LD50 orl-rat: 70 mg/kg TXAPA9 11,546,67

Odorless

12.13±0.46

Henry's Law constant = 1.70X10-9 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 3.47X10-11 cu-cm/molec sec at 25 °C (est)

III

6.1(b)

2757

It is stable to heat up to 100 °C. ... stable at neutral or slightly acid pH, but at pH 9 it is hydrolyzed to 4-hydroxybenzothiophene, methylamine, & carbon dioxide.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

Personal protective equipment should be issued to the workers engaged in the production of carbamates or in their agricultural use, in particular, eye protectors & respirators to those who spray crops.

Production equipment must be enclosed & provided with exhaust ventilation. ...Showers should be provided ...

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.

Mobam was among carbamates effective in protecting guinea pigs against soman poisoning. Mobam raised the LD50 of soman by a factor of about 8.|Insecticidal and acaricidal effect of 4-benzothienyl n-methylcarbamate was synergistically enhanced by piperonyl butoxide, sulfoxide or MGK 264.

LD50 Pigeon oral 273 mg/kg|LD50 Rat iv 24.8 mg/kg|LD50 Rat ip 40.8 mg/kg|LD50 Rat oral 70 mg/kg

/BIRDS and MAMMALS/ /Acute oral toxicity to birds had the following symptoms:/ asynergy, myasthenia, ataxia, imbalance, goose-stepping ataxia, stumbling or collapse, tremors, lacrimation, foamy salivation, diarrhea, tachypnea, dyspnea, loss of righting reflex, ataxia, tetany, tonic convulsions, clonic convulsions, wing-beat convulsions, and phonation.

Mobam's former production may have resulted in its release to the environment through various waste streams; its use as an insecticide(1) would have resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 195(SRC), determined from a structure estimation method(2), indicates that mobam is expected to have moderate mobility in soil(SRC). Volatilization of mobam from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Mobam is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.3X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Mobam had a reported half-life of one to three months in the surface six inches of soil(5).|TERRESTRIAL FATE: .. The half life ... on soil ... is about 30 days ... on a variety of crops the half life is 6-7 days ...|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 195(SRC), determined from a structure estimation method(2), indicates that mobam 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 1.7X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 13(SRC), from an estimated log Kow of 2.17(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Mobam was reported to be stable to hydrolysis at pH 2, have a half-life of 8 days at pH 7 and a half-life of 0.5 days at pH 9(8). After one month in a model aquatic ecosystem, mobam was reported to have a low degree of biodegradability(9).|AQUATIC FATE: A model aquatic ecosystem was constructed in a 15-gallon glass aquarium and consisted of white quartz sand, "standard" reference water, sorghum (Sorghum halpense), salt marsh caterpillar (Estigmene acrea), water flea (Daphnia magna), mosquito larvae (Culex pipiens quinquefasciatus), algae (Oedogonium cardiacum), Physa snails, and mosquito fish (Gambusia affinis)(1). Radio-labeled mobam was reported to have a low degree of biodegradability after 30 days of exposure. Residual and parent materials concentration in water was 8 ppb, in mosquito larvae 154,000 ppb, and in fish 1100 ppb. Mobam was highly toxic to snails(2).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), mobam, which has an estimated vapor pressure of 5.3X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase mobam 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 10 hours(SRC), calculated from its rate constant of 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase mobam may be removed from the air by wet or dry deposition(SRC). Mobam contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of mobam with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Mobam was reported to be stable to hydrolysis at pH 2, have a half-life of 8 days at pH 7 and a half-life of 0.5 days at pH 9(2). Mobam contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 13 was calculated in fish for mobam(SRC), using an estimated log Kow of 2.17(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of mobam can be estimated to be 195(SRC). According to a classification scheme(2), this estimated Koc value suggests that mobam is expected to have moderate mobility in soil.

The Henry's Law constant for mobam is estimated as 1.7X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that mobam is expected to be essentially nonvolatile from water and moist soil surfaces(2). Mobam is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.3X10-5 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to mobam may have occurred through inhalation and dermal contact with this compound at workplaces where mobam was produced or used. Mobam is not currently registered for use as an insecticide in the USA. (SRC)

... effective for the control of human lice when applied @ concentrations of 2 & 5% in pyrax powder either from a shaker can or from a power blower. /SRP: FORMER USE/

Within 24 hr after administration of (14)C-labeled MOBAM to a dairy cow ... 86% ... had been excreted in urine .... Approx 12% ... in the feces. In collected urines after administration of methyl and carbonyl labeled MOBAM, the sulfoxide, sulfoxide-4-sulfate, 4-sulfate and 4-glucuronide were identified.

MOBAM, (14)C-labeled in the ring, carbonyl or methyl position, was incubated with rumen bacterial cultures. Strains of genera Anaerovibrio, Bacteroides, Butyrivibrio, Eubacterium, Lachnospira & Ruminococcus were demonstrated to degrade MOBAM. MOBAM was metabolized to 4-hydro-benzothiophene /and CO2/.|(14)C-MOBAM was administered to dairy goats and a lactating cow/. Of carbonyl-(14)C & 38% of methyl-(14)C were exhaled as (14)CO within 24 hr.|Groups of male rats were administered labeled MOBAM by stomach tube. Urine & feces were collected daily. Hydroxybenzothiophene was recovered as the glucuronide & as the sulfate. Other metabolites were found but not identified. After administration of (14)C-MOBAM to dairy goats and a lactating cow, 2 metabolites were found in urine: 4-benzothienyl sulfate & 4-benzothienyl sulfate-1-oxide. These accounted for about 90% of the (14)C excreted in the urine.|In rats dosed with (14)C-ring labeled MOBAM, 76-87% of the label was excreted in 24 hr in urine. Benzenethienyl sulfate & glucuronide accounted for 83-87% of excreted (14)C. Within 24 hr after administration of methyl & carbonyl labeled MOBAM /to a dairy cow and a goat/, the sulfoxide, sulfoxide-4-sulfate, 4-sulfate & 4-glucuronide were identified.|For more Metabolism/Metabolites (Complete) data for MOBAM (7 total), please visit the HSDB record page.

Airway protection. Ensure that a clear airway exists. Intubate the patient and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /N-methyl carbamate insecticides/|Atropine. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access is difficult to obtain. Carbamates usually reverse with much smaller dosages of atropine than those required to reverse organophosphates. The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. Atropine does not reactivate the cholinesterase enzyme or accelerate excretion or breakdown of carbamate. Recrudescence of poisoning may occur if tissue concentrations of toxicant remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but is ineffective against nicotinic actions, specifically, muscle weakness and twitching and respiratory depression. Despite these limitations, atropine is often a life-saving agent in N-methyl carbamate poisonings. Favorable response to a test dose of atropine ... given intravenously can help differentiate poisoning by anticholinesterase agents from other conditions such as cardiogenic pulmonary edema and hydrocarbon ingestion. However, lack of response to the test dose, indicating no atropinization (atropine refractoriness), is characteristic of moderately severe to severe poisoning and indicates a need for further atropine. If the test dose does not result in mydriasis and drying of secretions, the patient can be considered atropine refractory. /N-methyl carbamate insecticides/|Skin decontamination. In patients with contaminated skin, clothing, hair, and/or eyes, decontamination must proceed concurrently with what ever resuscitative and antidotal measures are needed to preserve life. Flush the chemical from eyes with copious amounts of clean water. For asymptomatic individuals who are alert and physically able, a prompt shower and shampoo may be appropriate for thorough skin decontamination, provided the patient is carefully observed to insure against sudden appearance of poisoning. If there are any indications of weakness ataxia or other neurologic impairment, clothing should be removed and a complete bath and shampoo given while the victim is recumbent, using copious amounts of soap and water. Attendants should wear rubber gloves as vinyl provides no protection against skin absorption. Wash the chemical from skin folds and from under fingernails. Contaminated clothing should be promptly removed, bagged, and laundered before returning. Contaminated leather shoes should be discarded. Note that the pesticide can contaminate the inside surfaces of gloves, boot, and headgear. /N-methyl carbamate insecticides/|Gastrointestinal decontamination. If N-methyl carbamate has been ingested in a quantity probably sufficient to cause poisoning, consideration should be given to gastrointestinal decontamination ... . If the patient has presented with a recent ingestion and is still asymptomatic, adsorption of poison with activated charcoal may be beneficial. In significant ingestions, diarrhea, and/or vomiting are so constant that charcoal adsorption and catharsis are not indicated. Attention should be given to oxygen, airway management, and atropine. /N-methyl carbamate insecticides/|For more Antidote and Emergency Treatment (Complete) data for MOBAM (16 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ 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 resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi, and hypertension. ... jerky movements, incontinence, convulsions and coma. Death ... due to resp arrest of central origin, paralysis of resp muscles, intense bronchoconstriction or all three. /Carbaryl/|/CASE REPORTS/ ... Some spraymen /working with MOBAM/ complained of skin irritation and other subjective symptoms that did not prevent continued work, and no rash or other signs were observed.

... available as 50 and 80% wettable powders; 2, 5, and 50% dusts; 10% granular formulations; and 48% oil concentrates.|MCA-600|MOS-708|MCA 600|OMS-708

Experimental contact insecticide. Not actively marketed by Mobil Chemical Company.|Effective against cockroaches, flies, mosquitoes, aphids ... and a variety of crop insects. /SRP: former use/

Analysis: ultraviolet absorption and methyl amine evolution determination.|Residue is determined by Gas Chromatographic method.|Colorimetric method for the determination of 8 carbamate insecticide residues is described.|Determinations of pesticide residues by electron capture gas-liquid chromatography.