methyl N-(3,4-dichlorophenyl)carbamate

log Kow = 3.32

3.09

INSOL IN WATER; INSOL IN KEROSENE; IN ACETONE 46% & DIISOBUTYL KETONE 19%; IN DIMETHYLFORMAMIDE 64% & ISOPHORONE 33%; IN XYLENE LESS THAN 2.5%

Insoluble in water and kerosene; soluble in acetone and dimethylformamide

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

0.00139 [mmHg]

1.4X10-3 mm Hg at 25 °C /Estimated/

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 4 *

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 SWEP (6 total), please visit the HSDB record page.

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/

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 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.

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.

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)/

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.

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).

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).

Swep 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.

/BIRDS and MAMMALS/ As a rule, birds are not very sensitive to carbamates. /Carbamate pesticides/

/OTHER TERRESTRIAL SPECIES/ bees are extremely sensitive. /Carbamate pesticides/

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)

AEROBIC: Under upland soil conditions, 50% of swep applied at 15 to 35 ppm disappeared after 10 days, with a 90% loss occurring after 40 days(1). The degradation rate is dependent on temperature and not dependent on pH(1). Swep was added at a concentration of 500 ppm to a Nixon sandy loam soil at 60% water holding capacity; most remained unaltered, however, degradation products identified over a 40 day incubation period were 3,4-dichloroaniline and 3,3',4,4'-tetrachloroazobenzene(2). The half-life of swep in soil is 2-6 weeks, based on field observations(3).

ANAEROBIC: A study conducted in India found that in flooded soils treated at 150 and 1500 ppm, Swep concentrations were 50% decreased after 7 days and 90% decreased after 50 days(1).

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.

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

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.

Formerly used as a herbicide to control seedlings of annual weeds and grasses in rice, potatoes, cotton, corn, peas, peanuts, and sorghum; [HSDB]

No longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For SWEP (USEPA/OPP Pesticide Code: 084601) 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./

Herbicide

Swep is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

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.