3,5-Xylyl methylcarbamate

179.22

179.22

607-955-8

S0Z6GJ0V0R

35375

DTXSID7058042

Colorless crystalline solid /Technical grade, 97% pure/

29224999

38.3

2.23

Solid

0.54 g/cm³

99 °C

265.1ºC at 760mmHg

114.2ºC

1.515

470 mg l -1 (20 °C)

0-6°C

6.8 x 10 -3 Pa (25 °C)

Oral-Rat  LD50: 542 mg/kg; Oral-Mouse LD50: 245 mg/kg

Combustion produces toxic nitrogen oxide gas

Henry's Law constant= 3.91X10-8 atm-cu m/mole (est)

Non-corrosive

22

Xn

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

Rapidly hydrolyzed in alkaline media. Relatively stable to neutral and weakly acidic aqueous solutions. Stable to light and to temperatures up to 90 deg C.

P264, P270, P301+P312, P330, P501

H302

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Danger|P260, P264, P270, P301+P312, P307+P311, P321, P330, P405, and P501

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.

highly toxic

LD50 Rat oral 542 mg/kg|LD50 Rabbit oral 445 mg/kg|LD50 Mice oral 245 mg/kg|LD50 Mice oral 280 mg/kg

Since 3,5-xylyl methylcarbamate has been commercially produced for use as an insecticide(1), may have entered the environment during its production and particularly during its use(SRC).

Terrestrial fate: in soil, hydrolyzed to 3,5-xylenol and N-methylcarbamic acid.|TERRESTRIAL FATE: 3,5-xylyl methylcarbamate degrades in soil both by biological and abiotic hydrolysis of the carbamate linkage, producing carbon dioxide and the corresponding phenol(1-2). The rate of hydrolysis is dependent both on the nature of soil and soil pH(1-2). The half-life of 3,5-xylyl methylcarbamate has been estimated to 12.8 days in a silt soil of pH 7.85 and 750 days in a peat soil of pH 5.90(2). Since the compound is stable towards sunlight(6), photolysis in soil should not be important. The estimated Koc value of 389(3,SRC) suggests that the insecticide will be moderately adsorbed onto soil(4). However, adsorption of 3,5-xylyl methylcarbamate onto soil has been experimentally found to be stronger than would be expected from the estimated Koc value(1). It has been postulated that 3,5-xylyl methylcarbamate forms a complex with humus materials in soil and the complex remains irreversibly adsorbed in soil(1). Therefore, leaching of the compound will become less and less important as the carbon content of the soil increases. Based on an estimated Henry's Law constant (H) of 3.91X10-8 atm-cu m/mole(5) and the relationship between H and volatility(3), volatilization of 3,5-xylyl methylcarbamate from moist soil will not be important(SRC).|AQUATIC FATE: As in the case of soil, both biotic and abiotic hydrolysis are expected to degrade 3,5-xylyl methylcarbamate in water, but no quantitative data on the rate of hydrolytic degradation are available. Due to its ability to bind strongly with humus materials(1-2), 3,5-xylyl methylcarbamate is expected to be present predominantly adsorbed onto suspended solids and sediment in water. Because 3,5-xylyl methylcarbamate is stable to sunlight(5), photodegradation is not important in water. Based on its estimated value of the Henry's Law constant(4), volatilization of 3,5-xylyl methylcarbamate from water may be unimportant(3,SRC). The bioconcentration factors for 3,5-xylyl methylcarbamate in catfish (Ictalurus punctatus), crayfish (Procambaru sp.) and snail (Physa sp.) have been determined to be 550, 104 and 260(2).|ATMOSPHERIC FATE: 3,5-Xylyl methylcarbamate in the vapor phase may react with photochemically produced hydroxyl radicals with an estimated half-life of 5.6 hrs(1,SRC). Particle-bound 3,5-xylyl methylcarbamate is likely to be removed from the atmosphere by dry deposition(SRC).

3,5-Xylyl methylcarbamate is stable towards sunlight(1). The estimated rate constant for the reaction of 3,5-xylyl methylcarbamate with photochemically produced OH radicals is 6.853X10-11 cu cm/molecule-sec(2). Based on an atmospheric OH radical concn of 5X10+5/cu cm, the half-life of 3,5-xylyl methylcarbamate due to this reaction is 5.6hrs(1,SRC).

2.51|In an aquatic model ecosystem study, the bioconcentration factors for 3,5-xylyl methylcarbamate in algae (Oedogonium cardiacum), duckweed (Lemna minor), catfish (Ictalurus punctatus), crayfish (Procambaru sp.) and snail (Physa sp.) have been determined to be 3050, 2300, 550, 104 and 260, respectively(1).

51.29 L/kg|Based on a log Kow of 2.23(1) and a regression equation(2), the Koc value for 3,5-xylyl methylcarbamate has been estimated to be 389(SRC). This Koc value suggests that the insecticide will be moderately adsorbed to soils(3). However, due to formation of strong complexes with humic matter in soils, 3,5-xylyl methylcarbamate has been found to remain strongly adsorbed onto soils(4-5).

Based on an estimated Henry's Law constant of 3.91X10-8 atm-cu m/mole(1), the volatilization of 3,5-xylyl methylcarbamate from water or wet soil is not expected to be important(3,SRC). Based on this value of Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing at 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be over 1000 days(2,SRC).

Since 3,5-xylyl methylcarbamate is a solid(1), workers may be exposed to this insecticide both by inhalation and dermal route during manufacture. Dermal exposure is the most likely route for workers during spraying the wet or emulsified insecticide in the field(1,SRC).

These compounds are rapidly metabolized, 80% of the dose being eliminated in the urine within 24 hours, 0.5-15% in the feces and 0.1-1.0% in the milk. /Carbamate insecticides/|Carbamate pesticides are absorbed from the skin, lungs, and GI tract and distributed throughout the body. They do not accumulate in any particular tissue. ... /Carbamate pesticides/

XMC was applied to the green rice leafhopper (Nephotettix cincticeps Uhler) and the smaller brown planthopper (Laodelphax striatellus Fallen). Penetration into the insect was rapid and about 10-12 metabolites were formed. Only the N-hydroxymethyl metabolite was identified.|In insects, metabolism mainly involves hydroxylation of the benzene ring and the ring methyl substituents.|... Blood esterases would tend to inactivate a portion of the circulating carbamates. Liver microsomal enzymes break down the compounds within hours of exposure. Carbamates do not require activation by liver enzymes and therefore may be more hazardous for very young animals, in which hepatic degradative enzymes are deficient. Carbamates cross the rat placenta, depress fetal acetylcholinesterase, and are not readily metabolized in the fetus. ... /Carbamate pesticides/

Carbamates are reversible inhibitors of cholinesterase. The reversal means that the use of blood cholinesterase activity measurements for diagnostic purposes in animals suspected to be suffering from carbamate poisoning can produce normal or near normal assay results which are likely to be misleading. /Carbamate insecticides/|Acute toxicosis is due to inhibition of acetylcholinesterase, just as with the organophosphates. The carbamate insecticides occupy both the anionic and esteratic sites of acetylcholinesterase, the esteratic site being carbamylated rather than phosphorylated with the organophosphates. Acetylcholinesterase is able to hydrolyze carbamate insecticides, although the rate of hydrolysis is not as fast for the natural substrate acetylcholine. Thus carbamate insecticides are reversible inhibitors of acetylcholinestrase. Toxicosis develops when the amount of pesticide in the body is so large that the rate of carbamylation of acetylcholinesterase exceeds the rate of hydrolysis of pesticide by the enzyme. Acetylcholine then accumulares in neuroeffector and synaptic regions, resulting in clinical signs similar to those of organophosphates. /Carbamate insecticides/|Insecticide with predominantly contact action. Cholinesterase inhibitor.

The clinical approach to carbamate toxicity is similar to that for organophosphate poisoning; the major exception is that pralidoxime usually is not recommended. In carbaryl poisoning, pralidoxime may increase acetylcholinesterase inactivation. /Carbamates/|Assess the adequacy of the airway and ventilation and use oxygen, suction, intubation, artificial ventilation, intravenous lines, and cardiac monitors as needed. /Carbamates/|The usual measures of decontamination (ipecac/lavage, charcoal, cathartics) may be used when the patient presents within 2-4 hours of exposure. Container identification is important to determine appropriate therapeutic measures, since the vehicle (eg, hydrocarbon, methanol) may be as toxic as the insecticide. When syrup of ipecac is used, the patient must be observed closely to prevent aspiration. In experimental animals, carbaryl was not well absorbed by activated charcoal, but use of activated charcoal is still recommended because of its freedom from side effects. Be sure to remove contaminated clothing and wash the contaminated skin, as in organophosphate treatment. /Carbamates/|Atropine is the antidote of choice as in organophosphate poisoning. Although the total amount of atropine required usually is less, the same initial doses are recommended. Pralidoxime usually is unnecessary and may reduce the effectiveness of atropine (especially with carbaryl) In studies on mice the preadministration of pyridinium oximes (toxigonin, pralidoxime) reduces the LD50 several organophosphate compounds, except carbaryl. Patients require approximately 6-12 hours of atropine treatment, but all significantly poisoned patients should be observed at least 24 hours after the last atropine dose. /Carbamates/|For more Antidote and Emergency Treatment (Complete) data for 3,5-XYLYL METHYLCARBAMATE (8 total), please visit the HSDB record page.

With carbamate poisoning, plasma and red blood cell cholinesterase may be depressed, but usually return to normal within a few hours after exposure. /Carbamate poisoning/|Symptoms and signs of carbamate poisoning: Constriction of pupils; Salivation; Profuse sweating; Lassitude; Muscle incoordination; Nausea; Vomiting; Diarrhea; Epigastric pain; Tightness in chest. /Carbamates; from table/

3,5-xylyl methylcarbamate

Emulsifiable concentrate (200 g ai/l), wettable powder (500 g/kg), dustable powder (20 g/kg), microgranule (30 g/kg)|Mixed formulations: (XMC +) carbaryl; malathion; fenthion; edifenphos; diazinon; kasugamycin.

Product analysis is by hydrolysis to 3,5-xylenol, which is measured by ultraviolet spectroscopy. Residues may be determined by hydrolysis to 3,5-xylenol a derivative which is measured by gas liquid chromatography.