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Dimetilan

Dimetilan structure

Dimetilan 

structure
  • CAS No:

    644-64-4

  • Formula:

    C10H16N4O3

  • Chemical Name:

    Dimetilan

  • Synonyms:

    Carbamic acid,N,N-dimethyl-,1-[(dimethylamino)carbonyl]-5-methyl-1H-pyrazol-3-yl ester;Carbamic acid,dimethyl-,ester with 3-hydroxy-N,N,5-trimethylpyrazole-1-carboxamide;Carbamic acid,dimethyl-,1-[(dimethylamino)carbonyl]-5-methyl-1H-pyrazol-3-yl ester;Carbamic acid,dimethyl-,1-dimethylcarbamoyl-5-methylpyrazol-3-yl ester;Pyrazole-1-carboxamide,3-hydroxy-N,N,5-trimethyl-,dimethylcarbamate (ester);Geigy 22870;2-Dimethylcarbamoyl-3-methyl-5-pyrazolyl dimethylcarbamate;2-(N,N-Dimethylcarbamyl)-3-methylpyrazolyl-5 N,N-dimethylcarbamate;Snip Fly;2-Dimethylcarbamyl-3-methylpyrazol-5-yl dimethylcarbamate;1-Dimethylcarbamoyl-5-methyl-3-pyrazolyl dimethylcarbamate;Dimetilan;Dimetilane;1-(Dimethylcarbamoyl)-5-methyl-3-pyrazolyl N,N-dimethylcarbamate

  • Categories:

    Analytical Chemistry  >  Standard

Description

DIMETILAN is a colorless solid. The technical product is a yellow to reddish-brown solid. Used as an insecticide for insect control on livestock, especially housefly control. It is no longer produced commercially in the U.S. (EPA, 1998)


Dimetilan is a colorless solid. The technical product is a yellow to reddish-brown solid. Used as an insecticide for insect control on livestock, especially housefly control. It is no longer produced commercially in the U.S. (EPA, 1998)


Dimetilan is a colorless solid. The technical product is a yellow to reddish-brown solid. Used as an insecticide for insect control on livestock, especially housefly control. It is no longer produced commercially in the U.S. (EPA, 1998)

Dimetilan Basic Attributes

240.26

240.26

211-420-0

S53KQ82I35

2757

DTXSID2041880

Colorless solid

2933199011

Characteristics

67.7

0.27 (est)

Dimetilan is a colorless solid. The technical product is a yellow to reddish-brown solid. Used as an insecticide for insect control on livestock, especially housefly control. It is no longer produced commercially in the U.S. (EPA, 1998)

1.2g/cm3

68-71 °C

200-210 °C @ Press: 13 Torr

70 °F

1.547

In water, 2.1X10+5 mg/L at 25 deg C (est)

Storage: Prior to working with this chemical you should be trained on its proper handling and storage. Store in tightly closed containers in a cool, well-ventilated area.

9.7X10-5 mm Hg at 20 deg C

Oral-rat LD50: 25 mg/kg; Oral-Mouse LD50: 60 mg/kg

Thermal decomposition of toxic nitrogen oxide gas

Henry's Law constant = 4.14X10-11 atm-cu m/mol at 25 °C (est)

Hydrolyzed by acid and alkali.|UV light causes decomposition.|Hydroxyl radical reaction rate constant = 1.2X10-10 cu cm/molec-sec at 25 °C (est)

Readily soluble in water [Farm Chemicals Handbook].

Azo, Diazo, Azido, Hydrazine, and Azide Compounds

DIMETILAN is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Noncorrosive

Safety Information

II

6.1(a)

2757

3

21-25-50/53

36/37-45-60-61

EZ9084000

T,N

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

Hydrolyzed by acid and alkali

P273-P280-P301 + P310-P501

H301-H312-H410

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P191, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|Disposal Method Suggested: Alkali treatment followed by soil burial. Large amounts should be incinerated in a unit equipped with efficient gas scrubbing. In accordance with 40CFR165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your state pesticide or environmental control agency or by contacting your regional EPA office.

Hydrolyzed by acids and alkalis.

When heated to decomposition, it emits toxic fumes of nitrogen oxides. (Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) This material may burn but does not ignite readily. Container may explode in heat of fire. Hydrolyzed by acids and alkalis. (EPA, 1998)

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P280, P301+P310, P302+P352, P312, P321, P322, P330, P363, P391, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 194 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

(Non-Specific -- Carbamate Pesticide, Solid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind, keep out of low areas. Do not touch spilled material, or breathe the vapors, dusts, or fumes from burning materials. Do not handle broken packages without protective equipment. Wash away any material that may have contacted the body with soap and water. (EPA, 1998)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)|Protective clothing should be worn when working with the undiluted preparation.

Fire Extinguishing: Extinguish fire using agent suitable for types of surrounding fire, as the material itself burns with difficulty. Use water in flooding quantities as a fog. Wear positive pressure breathing apparatus and special protective clothing. Move container from fire area. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. Poisonous gases are produced in fire. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.

Spill Handling: Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

Skin contact and inhalation of fumes should be avoided.

Carbamate pesticides, solid, toxic, n.o.s. are in Hazard Class 6.1 and Dimetilan is in Packing Group II. It requires a "Poison" label.

P191; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Dimetilan is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .|Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

P191; As stipulated in 40 CFR 261.33, when dimetilan, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Toxicity

most toxic

.../In/ insecticidal action of these carbamates /there/ is pronounced synergism shown by addition of methylenedioxy compounds such as piperonyl butoxide, sesoxane, and propyl isome... These prevent in vivo detoxication of carbamates by inhibiting the "mixed function oxidase" detoxication system. /Carbamates/|The phenyl 2-propynyl ethers strongly synergized carbamate insecticides such as dimetilan against the housefly, Musca domestica. The phenyl 2-propynyl ethers were 2-5 times more active than the methylenedioxyphenyl synergists.

LD50 Rat oral 25 mg/kg|LD50 Rat dermal 600-700 mg/kg|LD50 Rat oral >50 mg/kg /Technical/|LD50 Guinea pig oral 63 mg/kg|For more Non-Human Toxicity Values (Complete) data for DIMETILAN (7 total), please visit the HSDB record page.

Dimetilan's former production and use as an insecticide(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 12(SRC), determined from a structure estimation method(2), indicates that dimetilan is expected to have very high mobility in soil(SRC). Volatilization of dimetilan from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.1X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dimetilan is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.7X10-5 mm Hg(4). Biodegradation data are not available(SRC, 2007).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that dimetilan 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 4.1X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.27(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Natural sunlight caused decomposition of dimetilan(8). Biodegradation data are not available(SRC, 2007).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimetilan, which has a vapor pressure of 9.7X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dimetilan 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 3 hrs(SRC), calculated from its rate constant of 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dimetilan may be removed from the air by wet or dry deposition(SRC). Natural sunlight caused decomposition of dimetilan(4).

EXPOSURE OF DIMETILAN TO UV RADIATION GAVE RISE TO 3 DEGRADATION PRODUCTS, 1 OF WHICH WAS IDENTIFIED AS MONOMETHYL CMPD 3-METHYL-5-HYDROXY-PYRAZOL-5-DIMETHYLCARBAMATE...|The rate constant for the vapor-phase reaction of dimetilan with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Dimetilan was found to be stable towards hydrolysis in the pH range of 6.0 to 10.0(2,4). It is hydrolyzed by acids and alkalis(3). Natural sunlight caused decomposition of dimetilan(5).

An estimated BCF of 3 was calculated in fish for dimetilan(SRC), using an estimated log Kow of 0.27(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 dimetilan can be estimated to be 12(SRC). According to a classification scheme(2), this estimated Koc value suggests that dimetilan is expected to have very high mobility in soil. Dimetilan showed low levels of adsorption on Kaolinite and Bentonite clays(3).

The Henry's Law constant for dimetilan is estimated as 4.1X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimetilan is expected to be essentially nonvolatile from water surfaces(2). Dimetilan is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.7X10-5 mm Hg(3).

Occupational exposure to dimetilan may have occured through inhalation and dermal contact with this compound at workplaces where dimetilan was produced or used. (SRC)

Drug Information

Harmful Effects and Symptoms Short Term Exposure: Very toxic; probable oral lethal dose for humans is 50-500 mg/kg or between 1 teaspoon and 1 oz for a 70 kg (150 lb) person. Dimetilan is highly toxic by ingestion and moderately toxic by contact with the skin. Death is primarily due to respiratory arrest of central origin, paralysis off the respiratory muscles, intense bronchoconstriction, or all three. This compound is a cholinesterase inhibitor. Symptoms are similar to carbaryl poisoning: nausea, vomiting, abdominal cramps, diarrhea, pinpoint pupils, excessive salivation, and sweating are common symptoms. Running nose and tightness in chest are common in inhalation exposures. Difficulty in breathing, raspy breathing, and loss of muscle coordination may also be seen. Exposure may also result in random jerky movements, incontinence, convulsions, and coma and death. Long Term Exposure: Many carbamates affect the central nervous system.|4-5. 4= Very toxic: probable oral lethal dose (human) 50-500 mg/kg, between 1 teaspoonful and 1 ounce for 70 kg person (150 lb). 5= Extremely toxic: probable oral lethal dose (human) 5-50 mg/kg, between 7 drops and 1 teaspoon for 70 kg person (150 lb).

Labeled dimetilan was administered orally to rats. Within 4 hr after treatment the urine contained 10% of the administered radioactivity and an additional 3% within the next 18 hr. ... Some production of carbon dioxide was observed. ... /in houseflies, American cockroaches, and German cockroaches/...13% of the injected dose was liberated as (14)CO2 within 1 hr...|...Carbamate insecticides...are rapidly...eliminated in rats. Within 49 hr after ip injection of carbonyl (14)C-labeled carbamate 89% of radioactivity was eliminated. Part appeared as CO2 (25-77%), products in urine (12-65%), and products in feces (1-6%), with 2-12%...remaining in body. /Carbamates/|Carbamates penetrate rapidly into insects, from 40-80% of topical dosage of 1 ug per housefly, penetrating within 4-8 hr. ... In mammals...carbamates are not accumulated in body or excreted in milk. /Carbamates/|.../Carbamate insecticides/ are rapidly... excreted in urine. /Carbamates/

Labeled dimetilan was administered orally to rats. ... 2 metabolites were recovered but not identified. ...other studies have shown a microsomal system, requiring TPNH and oxygen, that acts on n,n-dialkyl carbamates. Dealkylation occurs with formation of formaldehyde from n,n-dimethylcarbamates but not from n-methylcarbamates. Dimetilan was degraded by this system; and 2-methylcarbamoyl-3-methyl-5-pyrazolyl dimethyl carbamate + 2 unidentified compounds were observed. /in houseflies, American and German cockroaches/...hydrolysis of the carbamate ester group accounted for some metabolism, since 13% of the injected dose was liberated as (14)CO2...the metabolite formed first and the major product was probably 2-dimethylcarbamoyl-3-methyl-5-pyrazolyl n-hydroxymethyl n-methylcarbamate. ... A third metabolite found in all 3 insects co-chromatographed with 2-n-methylcarbamoyl-3-methyl-5-pyrazolyl dimethylcarbamate and exhibited the same biological activity.|... The metabolism of dimetilan in Aspergillus niger van Tieghem /was studied/. Together with hydrolysis, oxidation of the alkyl side chain appeared the most important modification (detoxification) process.|N-methyl hydroxylation appears to be major factor in detoxication in insects.

Dimetilan had half-life in houseflies... American cockroach... and German cockroach... of <0.5 hr.

... cholinesterase inhibitor. ...

Very toxic; probable oral lethal dose for humans is 50-500 mg/kg or between 1 teaspoon and 1 oz. for a 70 kg (150 lb.) person. Dimetilan is highly toxic by ingestion and moderately toxic by contact with the skin. Death is primarily due to respiratory arrest of central origin, paralysis of the respiratory muscles, intense bronchoconstriction, or all three. This compound is a cholinesterase inhibitor. (EPA, 1998)

Note: Dimetilan is a cholinesterase inhibitor. Signs and Symptoms of Dimetilan Exposure: Acute exposure to dimetilan usually leads to a cholinergic crisis, with signs and symptoms that may include increased salivation, profuse sweating, lacrimation (tearing), runny nose and spontaneous defecation and urination. Pinpoint pupils, blurred vision, headache, tremor, muscle twitching, tightness in chest, malaise, mental confusion, convulsions, and coma may also occur. Gastrointestinal effects include nausea, vomiting, diarrhea, and abdominal pain. Bradycardia (slow heart rate) occurs frequently. Pulmonary edema, dyspnea (shortness of breath), respiratory depression, or respiratory arrest may also occur. Emergency Life-Support Procedures: Acute exposure to dimetilan exposure may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to dimetilan. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to dimetilan. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas twice with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of dimetilan is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step 4. Ipecac should not be administered to children under 6 months of age.Warning: Ingestion of dimetilan may result in sudden onset of seizures or loss of consciousness. Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step 4.The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3- 1/2 oz) is recommended for adults. 6. Transport to a health care facility. (EPA, 1998)

INHALATION EXPOSURE: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to dimetilan. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Transport to a health care facility.|DERMAL/EYE EXPOSURE: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to dimetilan. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. DIMETILAN 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas twice with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Transport to a health care facility.|INGESTION EXPOSURE: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. ... 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with DIMETILAN 125 to 250 mL (1/2 to 1 cup) of water. ...|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Carbamates and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive=pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Administer atropine. Correct hypoxia before administration ... . In severely poisoned patients, administer pralidoxime chloride (2 PAM). DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. In rare cases diazepam or lorazepam may be necessary ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Carbamates and related compounds/

/SIGNS AND SYMPTOMS/ Dimetilan is a cholinesterase inhibitor. Acute exposure to dimetilan usually leads to a cholinergic crisis, with signs and symptoms that may include increased salivation, profuse sweating, lacrimation (tearing), runny nose and spontaneous defecation and urination. Pinpoint pupils, blurred vision, headache, tremor, muscle twitching, tightness in chest, malaise, mental confusion, convulsions, and coma may also occur. DIMETILAN Gastrointestinal effects include nausea, vomiting, diarrhea, and abdominal pain. Bradycardia (slow heart rate) occurs frequently. Pulmonary edema, dyspnea (shortness of breath), respiratory depression, or respiratory arrest may also occur.|/SIGNS AND SYMPTOMS/ Harmful Effects and Symptoms Short Term Exposure: Very toxic; probable oral lethal dose for humans is 50-500 mg/kg or between 1 teaspoon and 1 oz for a 70 kg (150 lb) person. Dimetilan is highly toxic by ingestion and moderately toxic by contact with the skin. Death is primarily due to respiratory arrest of central origin, paralysis off the respiratory muscles, intense bronchoconstriction, or all three. This compound is a cholinesterase inhibitor. Symptoms are similar to carbaryl poisoning: nausea, vomiting, abdominal cramps, diarrhea, pinpoint pupils, excessive salivation, and sweating are common symptoms. Running nose and tightness in chest are common in inhalation exposures. Difficulty in breathing, raspy breathing, and loss of muscle coordination may also be seen. Exposure may also result in random jerky movements, incontinence, convulsions, and coma and death. Long Term Exposure: Many carbamates affect the central nervous system.

dimetilan

Dimetilan Use and Manufacturing

Methods of Manufacturing

Reaction of 3-methylpyrazol-5-one with dimethylcarbamoyl chloride.|Dimetilan may be produced by the reaction of methylpyrazolone with two equivalents of dimethyl carbamoyl chloride.

Uses

Insecticide.

Production

(1972) LESS THAN 4.54X10+5 GRAMS (USE)|(1975) NONE

Aqueous solution.|Bait.|Emulsifiable concentrate.

The WHO Recommended Classification of Pesticides by Hazard identifies Dimetilan (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|GRAUER, URWYLER, US PATENT 3,452,043 (1969 TO GEIGY).|SWISS PATENT 281,946; BRITISH PATENT 618,376; US PATENT 2,681,879.|It is a stomach insecticide mainly used in public hygiene for the control of flies; it is applied as a bait spray containing 0.5% ai.

PRODUCT ANALYSIS: ...BY GLC WITH INTERNAL STANDARD. RESIDUES MAY BE DETERMINED BY GLC WITH MICROCOULOMETRIC DETECTION OR BY TLC. DETAILS OF UNPUBLISHED METHODS ARE AVAILABLE FROM CIBA-GEIGY AG. SEE ALSO: A MARGOT & K STAMMBACH, ANAL METHODS PESTIC PLANT GROWTH REGUL FOOD ADDIT 1964, 2, 183; ANAL METHODS PESTIC PLANT GROWTH REGUL, 1972, 6, 376.|AN HPLC METHOD FOR SIMULTANEOUS DETERMINATION OF CARBAMATE RESIDUES INCLUDING DIMETILAN IN FRUITS AND VEGETABLES IS DESCRIBED.|A PROCEDURE COUPLING HPLC WITH A CHOLINESTERASE INHIBITION AUTOANALYZER FOR THE DETERMINATION OF ORGANOPHOSPHATE & CARBAMATE INSECTICIDE RESIDUES IN AQ SAMPLES IS DISCUSSED. COMPOUNDS INCLUDED DIMETILAN.|Product analysis by: hydrolysis in acid, and distillation of the dimethylamine into standard boric acid (Suter, R et al. Z Analyt Chem, 1955, 147, 173) or GLC with internal standard. Residues may be determined by GLC with Coulson electrolytic conductivity detection or TLC; hydrolysis to dimethylamine which is reacted with carbon disulphide in the presence of cupric ions (Hall, SA et al, Analyt Chem, 1951, 23, 1866).|For more Analytic Laboratory Methods (Complete) data for DIMETILAN (6 total), please visit the HSDB record page.

Computed Properties

Molecular Weight:240.26
XLogP3:0.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:240.12224039
Monoisotopic Mass:240.12224039
Topological Polar Surface Area:67.7
Heavy Atom Count:17
Complexity:306
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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