Dipropyl isocinchomeronate
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Dipropyl isocinchomeronate
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CAS No:
136-45-8
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Formula:
C13H17NO4
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Chemical Name:
Dipropyl isocinchomeronate
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Synonyms:
2,5-Pyridinedicarboxylic acid,2,5-dipropyl ester;2,5-Pyridinedicarboxylic acid,dipropyl ester;R 326;Dipropyl isocinchomeronate;Di-n-propyl isocinchomeronate;Di-n-propyl 2,5-pyridinedicarboxylate;Dipropyl 2,5-pyridinedicarboxylate;Isocinchomeronic acid dipropyl ester;MGK-R 326;MGK Repellent 326;MGK 326;Repel 333;ENT 17595;NSC 22364;Quyingding;114308-72-4
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CAS No:
Description
DIPROPYL ISOCINCHOMERONATE is a solid.
Dipropyl isocinchomeronate appears as a solid.
Dipropyl isocinchomeronate appears as a solid.
Dipropyl isocinchomeronate Basic Attributes
251.28
251.28
205-245-9
O572Q51ABJ
22364
3082
DTXSID8032544
Amber liquid
2933399028
Characteristics
65.49000
2.21520
Dipropyl isocinchomeronate appears as a solid.
1.12
Liquid at room temperature
175 °C / 5mmHg
93.4 °C
Miscible with ethanol, kerosene, methanol, isopropanol
0-6°C
4.92X10-7 mm Hg at 25 deg C (est)
Mild aromatic odor
Henry's Law constant = 9.1X10-10 atm-cu m/mole at 25 °C (est)
pKa = 0.31 (est)
Technical product is a liquid at room temperature|Decomposed by sunlight and hydrolyzed by alkali. Lacks persistence at high humidity, a defect overcome by the addition 7-hydroxy-4-methylcoumarin|Hydroxyl radical reaction rate constant = 6.3X10-12 cu cm/molec-sec at 25 deg C (est)
No rapid reaction with air. No rapid reaction with water.
Amines, Phosphines, and Pyridines
Safety Information
UN 3082 9 / PGIII
US8000000
Stable under recommended storage conditions.
P273, P391, P501
H400
SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.
Incompatible materials: Strong oxidizing agents.
USEPA; Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) for Di-n-propyl isocinchomeronate (MGK Repellent 326) EPA738-R-03-003 (September 2003, Revised March 2005). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of April 20, 2017: http://www.epa.gov/pesticides/reregistration/status.htm]
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)
|Warning|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 46 companies from 2 notifications to the ECHA C&L Inventory.|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK (EU EN 14387) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Keep in suitable, closed containers for disposal.
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Because MGK Repellent 326 is not irritating to the eyes or the skin, it is in Toxicity Categories III and IV, respectively. Also, it is not a dermal sensitizer.
Dipropyl isocinchomeronate occurs as an active ingredient in various commercial insect repellent products intended for use on humans and animals. The maximum concentration of dipropyl isocinchomeronate allowed in end-use products intended for humans is 2.5% of active ingredient. Dipropyl isocinchomeronate is never used as the sole active ingredient, and is commonly formulated with DEET (N,N-diethyl-m-toluamide) and other active insect repellent ingredients. Concentration of dipropyl isocinchomeronate in aerosol products range from 1.0 to 2.5% active ingredient. Products used for dip applications to dogs and cats contain 4.0% and spray and towelette products with 0.2% and 1.0% active ingredient, respectively, are applied to horses. Concentrate products contain a maximum of 5.0% active ingredient for use as surface sprays to the interior of kennels, barns and other animal premises(1).
Toxicity
IDENTIFICATION AND USE: Dipropyl isocinchomeronate is an insect repellent. It is used on cats, dogs, human body and clothing, horses and pet living/sleeping quarters. HUMAN STUDIES: Dipropyl isocinchomeronate is a probable human carcinogen. ANIMAL STUDIES: Dipropyl isocinchomeronate was fed in diet to mice at 0, 125, 250, 500, 1000 or 2000 mg/kg/day for 13 weeks. Both sexes showed increased relative liver and brain weights. Males showed decreased kidney weights. In rats fed for 104 weeks, increased incidence in hepatocellular and renal cell adenomas and carcinomas, uterine polyps and testicular interstitial cell tumors were observed at 1000 mg/kg. In mice fed for 80 weeks, hepatocellular adenomas (females) and carcinomas in both sexes and alveolar bronchiolar adenomas (males) were observed at 2000 mg/kg. In rat developmental studies, reduced body weight in both sexes at 1000 mg/kg and mild proliferation of portal bile ducts with increased incidence of trace mononuclear cell infiltrate in the portal areas was observed in F0 females and both sexes of F1 at 1000 mg/kg/day. Dipropyl isocinchomeronate was negative for genotoxicity in Salmonella strains TA1535, TA1537, TA1538, TA98 and TA100 with and without metabolic activation.
LD50 Rabbit dermal 9500 mg/kg|LD50 Mouse ip 330 mg/kg|LD50 Mouse oral 1600 mg/kg|LD50 Rat dermal 9400 mg/kg|LD50 Rat oral 5230 mg/kg
Dipropyl isocinchomeronate's production and use as an insect repellent for use on both humans and animals(1) may result in its release to the environment through various waste streams(SRC). Commonly used spray and aerosol application of insect repellents containing dipropyl isocinchomeronate will release the compound directly to the environment(SRC). Dipropyl isocinchomeronate is never used as the sole active ingredient, and is commonly formulated with DEET (N,N-diethyl-m-toluamide) and other active insect repellent ingredients(1). Dipropyl isocinchomeronate improves the performance of DEET by slowing its evaporation and doing a better job of repelling various insects such as horse flies, stable flies and specific mosquitoes(2). Personal repellent products are washed off the human body and released in household wastewater into a treatment plant(1). Similarly, those products that are used as surface sprays of animal premises and pet dips would be discharged as wastewater, often to septic systems or sewage treatment plants(1).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 168(SRC), determined from a structure estimation method(2), indicates that dipropyl isocinchomeronate is expected to have moderate mobility in soil(SRC). Volatilization of dipropyl isocinchomeronate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Dipropyl isocinchomeronate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.92X10-7 mm Hg at 25 °C(3). Dipropyl isocinchomeronate is expected to hydrolyze in moist neutral and alkaline soils(SRC) based on aqueous hydrolysis half-lives of 17 days and 14 hours at pH 7 and pH 9 respectively(3). Biodegradation data in soil were not available(SRC, 2017). Photodegradation may occur on surfaces exposed to sunlight(SRC) since dipropyl isocinchomeronate is decomposed by sunlight(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 168(SRC), determined from a structure estimation method(2), indicates that dipropyl isocinchomeronate may adsorb moderately to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.1X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 100(SRC), from a log Kow of 3.57(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Dipropyl isocinchomeronate is stable to hydrolysis at pH 5; however, it does hydrolyze in neutral (pH 7) and alkaline (pH 9) water with half-lives of 17 days and 14 hours, respectively(6). Utilizing the Japanese MITI test, 1% of the Theoretical BOD was reached in 4 weeks indicating the compound is not readily biodegradable, however, the dipropyl isocinchomeronate hydrolyzed during the test forming pyridine-2,5-dicarboxylic acid and the ThBOD applies to the acid(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dipropyl isocinchomeronate, which has a vapor pressure of 4.92X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dipropyl isocinchomeronate 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 2.5 days(SRC), calculated from its rate constant of 6.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dipropyl isocinchomeronate may be removed from the air by wet and dry deposition(SRC). Dipropyl isocinchomeronate is decomposed by sunlight(4).
The rate constant for the vapor-phase reaction of dipropyl isocinchomeronate with photochemically-produced hydroxyl radicals has been estimated as 6.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Dipropyl isocinchomeronate remains stable under acidic conditions (pH 5) where no degradation was observed during 30 days of a hydrolysis study conducted for USEPA pesticide registration(2). However, dipropyl isocinchomeronate did hydrolyze in neutral (pH 7) and alkaline (pH 9) environments with half-lives of 17 days and 14 hours, respectively(2). In biodegradation studies using the Japanese MITI test protocol, dipropyl isocinchomeronate hydrolyzed to form pyridine-2,5-dicarboxylic acid(3). Dipropyl isocinchomeronate is reported to lack persistence at high humidity(4). Dipropyl isocinchomeronate is also reportedly decomposed by sunlight(4).
An estimated BCF of 100 was calculated in fish for dipropyl isocinchomeronate(SRC), using a log Kow of 3.57(1) and a regression-derived equation(2). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate to high(SRC), provided the compound is not metabolized by the organism(SRC). Although stable to aqueous hydrolysis at pH 5, dipropyl isocinchomeronate has hydrolysis half-lives of 17 days and 14 hours at pH7 and pH9, respectively(3), which will attenuate bioconcentration(SRC). In biodegradation studies using the Japanese MITI test protocol, dipropyl isocinchomeronate hydrolyzed to pyridine-2,5-dicarboxylic acid, and resulting bioconcentration tests using carp (Cyprinus carpio) which were exposed over an 6-week period determined BCF values of 0.3-8.6 for the pyridine-2,5-dicarboxylic acid(4).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of dipropyl isocinchomeronate can be estimated to be 168(SRC). According to a classification scheme(2), this estimated Koc value suggests that dipropyl isocinchomeronate is expected to have moderate mobility in soil.
The Henry's Law constant for dipropyl isocinchomeronate is estimated as 9.1X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dipropyl isocinchomeronate is expected to be essentially nonvolatile from water surfaces(2). Dipropyl isocinchomeronate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Dipropyl isocinchomeronate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.92X10-7 mm Hg(3).
Occupational exposure to dipropyl isocinchomeronate may occur through dermal contact with this compound at workplaces where dipropyl isocinchomeronate is produced or used. Use data indicate that the general population may be exposed to dipropyl isocinchomeronate via dermal contact with consumer products containing dipropyl isocinchomeronate(SRC). Dipropyl isocinchomeronate is used in various formulations applied to the skin as an insect repellent(1).
Drug Information
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ 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. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /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 ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Dipropyl isocinchomeronate Use and Manufacturing
The National Pesticide Information Retrieval System (NPIRS) identifies 17 companies with active labels for products containing the chemical MGK 326. To view the complete list of companies, product names and percent MGK 326 in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.|Farnam Wipe Original Formula Fly Protectant (Farnam Companies, Inc.): Active ingredient: MGK 326 1%; stabilene 20%; piperonyl butoxide 0.5%; and pyrethrins 0.2%.|Farnam Rol on Fly Repellent for Horses, Ponies & Dogs (Farnam Companies, Inc.): Active ingredient: MGK 326 1%; MGK 264 0.4%; piperonyl butoxide 1%; and pyrethrins 0.4%.|Spraypak Insect Repellent (Chase Products Company): Active ingredient: MGK 326 2.5%; MGK 264 5%; and diethyl toluamide 25%.|For more Formulations/Preparations (Complete) data for Dipropyl isocinchomeronate (29 total), please visit the HSDB record page.
Computed Properties
Molecular Weight:251.28
XLogP3:2.7
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:8
Exact Mass:251.11575802
Monoisotopic Mass:251.11575802
Topological Polar Surface Area:65.5
Heavy Atom Count:18
Complexity:280
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of Dipropyl isocinchomeronate
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CN
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Business licensedTrader Supplier of 3,5-Dinitrobenzoic acid,3,5-Din itrobenzoyl chloride,Sodium diatrizoate hydrate,Zinc-5-nitroisophthalate,3-Nitrophthalonitrile,4-Nitrophthalonitrile,Luminol (3-Aminophthalic hydrazide),3-Methyl-4-nitrobenzoic acid,3-Nitrophthalic acid,3-Nitrophthalimide,3-Nitrophthalic anhydride,Dimethyl 3-nitrophthalate,2-Methyl-6-nitro aniline,3-Nitrophthalhydrazide,4-Nitrophthalimide,4-Nitrophthalic acid,4-Nitrophthalic anhydride,4-Nitrosophenol,p-Benzoquinone dioxime,4-Methyl-3-nitrobenzoic acid,4-Chloro-3,5-dinitrobenzoic acid,Isobutyl 4-chloro-3,5-dinitrobenzoate,5-Nitroisophthalic acid,5-Aminoisophthalic acid,3,5-Diaminobenzoic acid,2-Chloro-5-nitrobenzoic acid,4-Chloro-3-nitrobenzoic acid,4-Nitro-N-methylphthalimide,Dimethyl 5-nitroisophthalate,Dimethyl 5-aminoisophthalate,3-Aminophthalimide,3-Methyl-2-nitrobenzoic acid,2-Amino-3-methylbenzoic acid,2-(4-Chloro-3-nitrobenzoyl) benzoic acid,2-(3-Amino-4-chlorobenzoyl)benzoic acid,3-Aminophthalic acid,4-Aminophthalic acid,3-Amino-4-methylbenzoic acid,4-Methyl-3-nitrobenzoate,Methyl 3-amino-4-methylbenzoate,Methyl 3-methyl-2-nitrobenzoate,3,5-Dinitrobenzonitrile,4-Aminophthalimide,4-Amino-N-methylphthalimide,3,5-DinitrobenzamideInquiryCAS No.: 136-45-8Grade: Pharmaceutical GradeContent: 98%
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