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Home > Encyclopedia > Methyl N-(3,4-dichlorophenyl)carbamate

Methyl N-(3,4-dichlorophenyl)carbamate

Methyl N-(3,4-dichlorophenyl)carbamate structure

Methyl N-(3,4-dichlorophenyl)carbamate 

structure
  • CAS No:

    1918-18-9

  • Formula:

    C8H7Cl2NO2

  • Chemical Name:

    Methyl N-(3,4-dichlorophenyl)carbamate

  • Synonyms:

    Carbamic acid,N-(3,4-dichlorophenyl)-,methyl ester;Carbanilic acid,3,4-dichloro-,methyl ester;Carbamic acid,(3,4-dichlorophenyl)-,methyl ester;NIA 2995;MCC (herbicide);Methyl 3,4-dichlorocarbanilate;Methyl N-(3,4-dichlorophenyl)carbamate;Swep;Methyl 3,4-dichlorophenylcarbamate;MCC;3,4-Dichlorophenylcarbamic acid methyl ester

  • Categories:

    Agrochemicals  >  Herbicides

Description

SWEP is a carbamate ester.

Methyl N-(3,4-dichlorophenyl)carbamate Basic Attributes

220.05

220.05

6A0988TW71

DTXSID7042437

WHITE CRYSTALS

2924299036

Characteristics

38.33000

3.41

1.4±0.1 g/cm3

112-114 °C

252.3±30.0 °C at 760 mmHg

106.4±24.6 °C

1.597

In water, 50 mg/L at 25 deg C /Estimated/

0-6°C

1.4X10-3 mm Hg at 25 deg C /Estimated/

Oral-Rat  LD50: 522 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

Henry's Law constant = 1.2X10-8 atm cu m/mol at 25 °C /Estimated/

Hydroxyl radical reaction rate constant = 9.4X10-12 cu cm/molec sec at 25 °C /Estimated/

Safety Information

NONH for all modes of transport

22

FD8750000

Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Volatility 30% dissipation after 24 hr at 40 deg C

P264, P270, P301+P312, P330, P501

H302

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.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, nec, liquid)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec); Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

Extinguish fire using agent suitable for type of surrounding fire. Material itself does not burn or burns with difficulty. /Carbaryl (agricultural insecticides, nec, liquid); Carbaryl (agricultural insecticides, nec, other than liquid); Carbaryl (insecticides, other than agricultural, nec/|If material /is/ on fire or involved in /a/ fire do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, liquid, nos, (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec/|Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, liquid nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

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.

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/

Toxicity

moderately

LD50 Rat oral 522 mg/kg|LD50 Rabbit dermal 2480 mg/kg|LD50 Rat oral 4197 mg/kg /Technical/

/BIRDS and MAMMALS/ As a rule, birds are not very sensitive to carbamates. /Carbamate pesticides/|/OTHER TERRESTRIAL SPECIES/ bees are extremely sensitive. /Carbamate pesticides/

Swep's former production and use as a herbicide(1) may have resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 65(SRC), determined from a log Kow of 3.32(2) and a regression-derived equation(3), indicates that swep is expected to have high mobility in soil(SRC). Volatilization of swep from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Swep is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-3 mm Hg(SRC), determined from a fragment constant method(5). A 50% degradation after 10 and 7 days when incubated in soils under nonflooded and flooded conditions, respectively(6), indicates that biodegradation may be of moderate importance in the terrestrial environment; however, swep has been shown to inhibit CO2 evolution in soil(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 65(SRC), determined from a log Kow of 3.32(2) and a regression-derived equation(3), indicates that swep is not 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 1.2X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 72(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). A 50% degradation after 10 and 7 days when incubated in soils under nonflooded and flooded conditions, respectively(7), indicates that biodegradation may be an important fate process in the aquatic environment; however, swep has been shown to inhibit CO2 evolution in soil(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), swep, which has an estimated vapor pressure of 1.4X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase swep 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 2 days(SRC), calculated from its rate constant of 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of swep with photochemically-produced hydroxyl radicals has been estimated as 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Swep is not expected to undergo hydrolysis in the environment due to the lack of readily hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

An estimated BCF of 72 was calculated for swep(SRC), using a log Kow of 3.32(1) and a regression-derived equation. According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

549.54 L/kg|The Koc of swep is estimated as 65(SRC), using a log Kow of 3.32(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that swep is expected to have high mobility in soil.

The Henry's Law constant for swep is estimated as 1.20X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that swep is expected to be essentially nonvolatile from water surfaces(2). Swep is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-3 mm Hg(SRC) determined from a fragment constant method(3).

DRINKING WATER: A 1991 US EPA study of the well water in the lower 48 states found no swep in the 178 wells tested for the herbicide(1). In a similar study of wells in California conducted in 1991, 166 wells were sampled and swep was not detected in any test well(2).

Occupational exposure and general population exposure should be low or non-existent since swep is no longer produced or used in the US (May, 2005). In the past, swep was applied directly to the soil as a herbicide and exposure to this compound was primarily in the workplace where swep was produced or in the fields where it was applied. (SRC)

Drug Information

Mice were orally administered 420 mg of phenyl-(14)C-labeled carbanilate/kg to 5-week-old male STD-DDY mice. Feces & urine were collected daily for 5 days. Swep was swiftly distributed throughout the mouse body & was almost completely excreted within 48 hr in urine & feces, especially urine. In feces swep was excreted unchanged.|... Swep was found ... resistant to hydrolysis by rice plants. ... There was not a large incorporation of 3,4-dichloroaniline moiety of Swep into the insoluble lignin complex. Instead, intact herbicide incorporated directly.|The metabolism of methyl 3,4-dichlorocarbanilate (Swep) in the mouse was studied by orally administering 420 mg of phenyl-14C-labeled carbanilate/kg to 5-week-old male STD-ddy mice. Following herbicide administration their urine and feces were collected daily for 5 days to determine the radioactivity, and the organs of untreated control mice mouse were analyzed as well as the whole-body autoradiographs. It was shown that the orally administered swep was swiftly distributed throughout the mouse body and was almost completely excreted within 48 hr in urine and feces, especially urine.

In studies on the mouse, it was determined that in mouse urine, Swep was metabolized into water-soluble substances conjugated with glucuronic acid and sulfuric acid.|In soil ... Swep was transformed to 3,4-dichloroaniline, 3,3',4,4'-tetrachloroazobenzene ... & other unidentified compd. ... The nature of microflora responsible for biodegradation ... was not known.|In greenhouse studies Swep was applied to rice, carrots, oats, wheat, corn, & barnyard grass. There were indications that trace amounts of Swep were hydrolyzed in soil to 3,4-dichloroaniline. However ... most of the herbicide was immobilized & bound as a lignin complex...|... In feces swep was excreted virtually unchanged, however, in urine it was metabolized into water-soluble substances conjugated with glucuronic acid and sulfuric acid.

Skin contamination should be treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other Herbicides/|If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and and fluid balance and administer intravenous infusions of glucose, normal saline ringer's solution, or ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. Fluids serve to support excretion of the toxicants. Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides. /Other Herbicides/

methyl 3,4-dichlorocarbanilate

Methyl N-(3,4-dichlorophenyl)carbamate Use and Manufacturing

Methods of Manufacturing

Preparation method 1: Using benzene as a solvent, 3,4-dichloroaniline is reacted with methyl chloroformate to prepare metronidazole. Preparation method Two, 3,4-dichlorophenyl isocyanate and methanol are added to prepare the dimethalin.

Uses

Can be used before and after buds to control annual weeds in rice and large seed legumes

Emulsifiable concentrate 2 lb/US gallon active ingredient. Wettable powder for rice application. Granules of Swep and MCP for use on paddy rice.

Swep was among some phenylurea herbicides investigated in order to detect and estimate impurities with toxicological or ecotoxicological danger.|/SRP 2005: Former use/ For soil treatment and foliage contact. Used for paddy and upland rice, rice seeding bed, corn, pea, and peanut.|/SRP 2005: Former use/ Pre- and post-emergent herbicide for control of seedlings of annual weeds and grasses. Recommended for use on carrots, potatoes, cotton, rice and sorghum.

SEPARATION & IDENTIFICATION OF SWEP WAS ACCOMPLISHED BY COLUMN, THIN-LAYER, GLC WITH ELECTRON CAPTURE & FLAME IONIZATION.|SWEP WAS AMONG THE HERBICIDES ANALYZED BY THIN LAYER CHROMATOGRAPHY AND FLUORIMETRY. THE HERBICIDES COULD BE DETERMINED IN WATER AT PPB LEVELS WITH HIGH RECOVERIES, AND WITHOUT CLEANUP.|THE DETERMINATION OF THE HERBICIDE RESIDUES IS BASED ON HYDROLYSIS WITH METHANOLIC POTASSIUM HYDROXIDE TO ANILINES. AFTER EXTRACTION WITH ORGANIC SOLVENTS, THE EXTRACT IS USED DIRECTLY FOR HYDROLYSIS AT THE START POINT OF THIN LAYER CHROMATOGRAPHIC PLATE, AFTER WHICH THE PLATE IS DEVELOPED & THEN SPRAYED WITH FLUORESCAMINE SOLUTION (0.1 MG/ML ACETONE).|Method: AOAC 992.14; Procedure: liquid chromatographic method with ultraviolet detector; Analyte: SWEP; Matrix: finished drinking water; Detection Limit: low-mid ppb (ng/mL) range.

Computed Properties

Molecular Weight:220.05
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:218.9853839
Monoisotopic Mass:218.9853839
Topological Polar Surface Area:38.3
Heavy Atom Count:13
Complexity:189
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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