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Propamocarb

Propamocarb structure

Propamocarb 

structure
  • CAS No:

    24579-73-5

  • Formula:

    C9H20N2O2

  • Chemical Name:

    Propamocarb

  • Synonyms:

    Carbamic acid,N-[3-(dimethylamino)propyl]-,propyl ester;Carbamic acid,[3-(dimethylamino)propyl]-,propyl ester;N-(γ-Dimethylaminopropyl)carbamic acid propyl ester;SN 39744;Propamocarb;Nor-Am 39744;Plantacur E;Plantacur;1135443-13-8

  • Categories:

    Agrochemicals  >  Fungicides

Description

Propamocarb is colourless liquid


Propamocarb is a carbamate ester that is the propyl ester of 3-(dimethylamino)propylcarbamic acid. It is a systemic fungicide, used (normally as the hydrochloride salt) for the control of soil, root and leaf diseases caused by oomycetes, particularly Phytophthora and Pythium species. It has a role as a xenobiotic, an environmental contaminant and an antifungal agrochemical. It is a carbamate ester, a tertiary amino compound and a carbamate fungicide. It derives from a propan-1-ol.

Propamocarb Basic Attributes

188.27

188.27

607-406-2

8HLL7N9UWO

DTXSID1040295

2924199090

Characteristics

41.6

1.80

1.0±0.1 g/cm3

45-55ºC

bp18mm 139-141°

>100 °C

1.456

4.78 M|In water, 9.0X10+5 mg/L at 20 °C, pH 7.0|In hexane >883, methanol >933, dichloromethane >937, toluene >852, acetone >921, ethyl acetate >856 (all in g/L, 20 °C)

APPROX 4°C

0.05 mmHg|5.48X10-2 mm Hg at 25 °C

1.48e-09 atm-m3/mole|Henry's Law constant = 1.48X10-9 atm-cu m/mol at 25 °C (1.5X10-4 Pa-cu m/mol)

pKa = 9.50 (strong base)

144.69 Ų [M+H]+

Colorless, fairly aromatic, hygroscopic crystals. MP: 64.2 °C. VP: 3.8X10-2 mPa at 20 °C. logP: -1.21 (pH 7). Henry's Law constant: <1.7X10-8 Pa-cu m/mol at 20 °C (est). Density: 1.085 g/mL at 20 °C, aqueous concentrate. Solubility in water: 0.500 g/L (pH 1.6-9.6, 20 °C). Solubility in methanol 656, dichloromethane >626, acetone 560.3, ethly acetate 4.34, toluene 0.4, hexane <0.01 (all in g/L at 20 °C). Stable to hydrolysis and photolysis. pKa 9.3 (20 °C. Surface tension pure substance 71.98 mN/m (20 °C) /Propamocarb hydrochloride/|Very soluble in water, ethanol, dichloroethane; sparingly soluble in toluene, hexane|Hydroylsis rate: 1.51X10-8/day. Photolysis rate: 0.0196/day in soil; 4.16/day in air; stable in water /Propamocarb hydrochloride/|Hydroxyl radical reaction rate constant = 9.88X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

2

22

EZ8857000

Xn

Stable. Incompatible with strong oxidizing agents.

P264, P270, P301+P312, P330, P501

H302

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. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Propamocarb Hydrochloride (Septmber 1995). 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 July 2, 2018: http://www.epa.gov/pesticides/reregistration/status.htm]

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 127 companies from 1 notifications to the ECHA C&L Inventory.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).|Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. 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 fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. 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: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. 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.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Normal measures for preventive fire protection.|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.

Propamocarb concentrations on 90 bouquets of the most commonly sold cut flowers in Belgium (50 bouquets of roses; 20 of gerberas, and 20 of chrysanthemums). Bouquets were collected from 50 florists located in the seven largest cities of Belgium (Antwerp, Brussels, Charleroi, Ghent, Leuven, Liege, and Namur) and from five supermarkets located in the different regions(1).[Table#8502]

Toxicity

IDENTIFICATION AND USE: Propamocarb is a fungicide used as a soil and seed treatment, a dip treatment for bulbs and tubers, and a foliar fungicide. It should be used preventatively. Its spectrum of activity is confined to Oomycetes. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: In mice treated with single iv dose of propamocarb hydrochloride 30 mg/kg b.w. it caused restlessness and increased motor activity. After 100 mg/kg b.w., additional symptoms such as irregular breathing and exophthalmos appeared. Death occurred at 175 mg/kg b.w. and above consequent to the development of clonic convulsions. No clinical signs of toxicity or abnormalities in normal reflexes and autonomic function were seen at 10 mg/kg b.w. or below. Dogs were fed the free base of propamocarb hydrochloride in the diet at 0, 50, 100, 500 or 1000 ppm for 90 days with the top dosage level being raised to 2000 ppm at week 7. Assay of plasma, erythrocyte and brain cholinesterase revealed no significant inhibition. Rabbits with skin sites exposed to propamocarb hydrochloride five hours/day for 28 consecutive days, had signs of local irritation including reddening, scabbing and thickening of the epithelium. Additionally, the abraded sites showed reactions such as swelling and induration. In rats the neoplastic changes demonstrated in males included increased occurrence of subcutaneous fibrosarcoma in the treated groups. The difference from concurrent controls was statistically significant at 40 ppm and 1000 ppm. In rabbits fetal weight was depressed at both 0.4 and 0.8 mL/kg b.w. In rats, retarded fetal development noted at and above 1 mL/kg b.w. A dosage level of 3 mL/kg b.w. was toxic to both mothers and fetuses in rats. In mice, propamocarb did not increase the frequency of micronucleated erythrocytes, but decreased the polychromatic/normochromatic erythrocytes ratio. Propamocarb increased only gaps in total chromosome aberrations, but when gaps were excluded, there were no significant differences in total aberrations.

Twenty-four pesticides were tested for interactions with the estrogen receptor (ER) and the androgen receptor (AR) in transactivation assays. Estrogen-like effects on MCF-7 cell proliferation and effects on CYP19 aromatase activity in human placental microsomes were also investigated. Pesticides (endosulfan, methiocarb, methomyl, pirimicarb, propamocarb, deltamethrin, fenpropathrin, dimethoate, chlorpyriphos, dichlorvos, tolchlofos-methyl, vinclozolin, iprodion, fenarimol, prochloraz, fosetyl-aluminum, chlorothalonil, daminozid, paclobutrazol, chlormequat chlorid, and ethephon) were selected according to their frequent use in Danish greenhouses. In addition, the metabolite mercaptodimethur sulfoxide, the herbicide tribenuron-methyl, and the organochlorine dieldrin, were included. Several of the pesticides, dieldrin, endosulfan, methiocarb, and fenarimol, acted both as estrogen agonists and androgen antagonists. Prochloraz reacted as both an estrogen and an androgen antagonist. Furthermore, fenarimol and prochloraz were potent aromatase inhibitors while endosulfan was a weak inhibitor. Hence, these three pesticides possess at least three different ways to potentially disturb sex hormone actions. In addition, chlorpyrifos, deltamethrin, tolclofos-methyl, and tribenuron-methyl induced weak responses in one or both estrogenicity assays. Upon cotreatment with 17beta-estradiol, the response was potentiated by endosulfan in the proliferation assay and by pirimicarb, propamocarb, and daminozid in the ER transactivation assay. Vinclozolin reacted as a potent AR antagonist and dichlorvos as a very weak one. Methomyl, pirimicarb, propamocarb, and iprodion weakly stimulated aromatase activity. Although the potencies of the pesticides to react as hormone agonists or antagonists are low compared to the natural ligands, the integrated response in the organism might be amplified by the ability of the pesticides to act via several mechanism and the frequent simultaneous exposure to several pesticides.

LD50 Mouse oral 1600 to >2858 mg/kg /Propamocarb hydrochloride/|LD50 Mouse (male) sc 1710 mg/kg /Propamocarb hydrochloride/|LD50 Mouse (female) sc 1870 mg/kg /Propamocarb hydrochloride/|LD50 Mouse (male) ip 457 mg/kg /Propamocarb hydrochloride/|For more Non-Human Toxicity Values (Complete) data for Propamocarb (13 total), please visit the HSDB record page.

Propamocarb's production may result in its release to the environment through various waste streams; its use as a fungicide(1) for turf in the US(2) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 100(SRC), determined from a structure estimation method(2), indicates that propamocarb is expected to have high mobility in soil(SRC). Volatilization of propamocarb from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.48X10-9 atm-cu m/mole(3). Propamocarb is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.48X10-2 mm Hg at 25 °C(3). Propamocarb was not biodegraded in pure culture tests(4).|FIELD STUDY: Dissipation kinetics of two systemic fungicides, namely fluopicolide and propamocarb used as a combination formulation (Infinito 68.75 SC), were studied on tomato at four different locations by the All India Network Project on Pesticide Residues to recommend their pre-harvest interval (PHI) and to propose the maximum residue limits (MRL) for the two fungicides based on chronic hazard exposure assessment. The combination fungicide was sprayed thrice at the recommended dosage of 93.75 g a.i./ha fluopicolide and 937.50 g a.i./ha propamocarb as well as at double the recommended dosage of 187.50 g a.i./ha fluopicolide and 1875.0 g a.i./ha propamocarb on tomato crops and the residues were monitored periodically by GC-MS. The fungicides dissipated to below the limit of quantification (LOQ) within 10 to 15 days, with a half-life of 2-4 days for fluopicolide and 1-2 days for propamocarb. ...|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 100(SRC), determined from a structure estimation method(2), indicates that propamocarb is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.48X10-9 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 2.5(SRC), from its log Kow of 1.12(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Propamocarb was not biodegraded in pure culture tests(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), propamocarb, which has a vapor pressure of 5.48X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase propamocarb 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 4 hours(SRC), calculated from its rate constant of 9.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Propamocarb is stable to photolysis(2).

The rate constant for the vapor-phase reaction of propamocarb with photochemically-produced hydroxyl radicals has been estimated as 9.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 4.9X10-6 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 4.5X10+4 and 4500 yrs at pH values of 7 and 8, respectively(1). Propamocarb is stable to hydrolysis in the environmen(2). Propamocarb is stable to photolysys(2).

An estimated BCF of 2.5 was calculated in fish for propamocarbl(SRC), using a log Kow of 1.12(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 propamocarb can be estimated to be 100(SRC). According to a classification scheme(2), this estimated Koc value suggests that propamocarb is expected to have high mobility in soil(SRC). A Koc of 309 was reported for propamocarb hydrochloride(3).

The Henry's Law constant for propamocarb is 1.48X10-9 atm-cu m/mole(1). This Henry's Law constant indicates that propamocarb is expected to be essentially nonvolatile from water and moist soil surfaces(2). Propamocarb is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.48X10-2 mm Hg(1).

No reports of surface water or ground water monitoring studies that included propamocarb were found in searches of the United States Geological Survey (USGS) online National Water Quality Assessment Data Warehouse (NAWQA) database, nor the EPA publication, EPA Pesticides in Ground Water, A Compilation of Monitoring Studies 1971-1991 National Summary(1).

Propamocarb was tested for in 14 vegetables, 22 vegetables and 7 other food commodities over two years from April 1991-March 1993 as part of a total diet study conducted in Belgium(1):[Table#8499]

Occupational exposure to propamocarb may occur through inhalation and dermal contact with this compound at workplaces where propamocarb hydrochloride is produced or used. Limited monitoring data indicate that the general population may be exposed to propamocarb via ingestion of contaminated food. (SRC)|In order to assess the prevalence of pesticide contamination and the risk of florists' exposure when handling cut flowers, sampling and analysis of 90 bouquets of the most commonly sold cut flowers in Belgium (50 bouquets of roses; 20 of gerberas, and 20 of chrysanthemums) were carried out. The bouquets were collected from 50 florists located in the seven largest cities of Belgium (Antwerp, Brussels, Charleroi, Ghent, Leuven, Liege, and Namur) and from five supermarkets located in the different regions. To have a better understanding of the route of exposure and professional practices a questionnaire was also addressed to a group of 25 florists who volunteered to take part in the survey. All florists were interviewed individually when collecting the questionnaire. The residual pesticide deposit values on cut flowers were determined in an accredited laboratory using a multi-residue (QuEChERS Quick Easy Cheap Effective Rugged Safe) method and a combination of gas chromatography (GC) and liquid chormatograhphy (LC) analysis. A total of 107 active substances were detected from all samples; i.e., an average of about 10 active substances per bouquet. The most severely contaminated bouquet accumulated a total concentration of residues up to 97 mg/kg. Results show that roses are the most contaminated cut flowers; with an average of 14 substances detected per sample and a total concentration per rose sample of 26 mg/kg. Some active substances present an acute toxicity (acephate, methiocarb, monocrotophos, methomyl, deltamethrin, etc.) and exposure can generate a direct effect on the nervous system of florists. Nevertheless, fungicides (dodemorph, propamocarb, and procymidone) were the most frequently detected in samples and had the highest maximum concentrations out of all the active substances analysed. Dodemorph was the most frequently detected substance with the highest maximum concentration (41.9 mg/kg) measured in the rose samples. It appears from the survey that, despite being exposed to high deposits of residues, florists usually do not protect themselves from contact with residues even if they spend several hours handling cut flowers and preparing bouquets (from 2 to 6 h/day, depending on the time of year and/or selling periods) daily. Bad habits (eating, drinking, or smoking at work) and absence of personal protective equipment of most florists also increase the risk of contact with pesticide residues.

Drug Information

After a single oral dose of 0.5 mg/kg b.w. of (14)C-propamocarb hydrochloride, female rats excreted approximately 90% of the administered radioactivity within 24 hours of dosing via the urine (87%), feces (2.5%) and expired air (<0.3%). Similar rapid elimination of (14)C-propamocarb hydrochloride by female rats was also observed following oral administration of 0.5 mg (14)C-propamocarb hydrochloride/kg b.w./day for 21 days. During the 21-day dosing period, an average of 83% and 3.2% of the daily administered dose was recovered respectively in the urine and the feces. At sacrifice, 24 hours after acute or subacute oral dosing, total (14)C residues detected in the 19 tissues analyzed including, among others liver, kidney, lung, spleen, heart, adipose tissue, skin and skeletal muscle (but excluding the alimentary tract) accounted for 1.7% of the single dose and approximately 0.3% of the total dose given over a 21 day dosing period (equivalent to approximately 7% of the last daily dose). Female rats with "Acute biliary - and urethra fistula" treated with a single intraduodenal dose of 0.5 mg/kg b.w. of (14)C-propamocarb hydrochloride eliminated 81% of the administered radio-activity in the urine as early as six hours after dosing. By 24 hours post- administration, a total of 92% of the (14)C was recovered in the urine as compared to only 1.8% in the bile /Propamocarb hydrochloride/

/SRP:/ Immediate first aid: Remove patient from contact with the material. 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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Dithiocarbamates and Related Compounds/|/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 necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. 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. Administer activated charcoal ... . /Dithiocarbamates and Related Compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or is in severe respiratory distress. Use moderate hyperventilation (rate of 20 respirations per minute) if signs of cerebral edema are present. 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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Dithiocarbamates and Related Compounds/|Decontaminate skin promptly by washing with soap and water. Treat contamination of the eyes immediately by prolonged flushing with copious amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other herbicides/|For more Antidote and Emergency Treatment (Complete) data for Propamocarb (7 total), please visit the HSDB record page.

Previcur

Propamocarb Use and Manufacturing

Methods of Manufacturing

Add acrylonitrile in a three-necked flask, heat the water bath to an appropriate temperature, pass dimethylamine gas, and react for 1h to obtain β-dimethylaminopropionitrile. Then add β-dimethylaminopropionitrile, catalyst, and solvent to the autoclave, vent the air with nitrogen, vent hydrogen at a suitable temperature, and the autoclave pressure is 5MPa, until the autoclave pressure does not drop to the end, cool, decompress the solvent, collect 73 ~75℃/9×103Pa fraction to obtain N, N-dimethyl-1, 3-dipropylamine. Finally, the product of the previous step is mixed with the solvent and the acid binding agent in a three-necked bottle, n-propyl chloroformate is added dropwise under cooling, the reaction temperature is 30-40°C, and the reaction is continued for 1 hour after the drop, filtration, washing, collecting the filtrate and washing liquid The product can be obtained by desolvation by pressure. The yield is 66%~67%, and the content is over 90%.

Uses

Carbamate fungicide used in the agriculture industry

Advan Propamocarb (Advan LLC): Active ingredient: propamocarb hydrochloride 66.8%. /Propamocarb hydrochloride/|Proplant MUP (Arysta Lifescience Benelux): Active ingredient: propamocarb hydrochloride 66.8%. /Propamocarb hydrochloride/|Proplant Turf and Ornamental Fungicide (Arysta Lifescience Benelux): Active ingredient: propamocarb hydrochloride 66.8%. /Propamocarb hydrochloride/|Promess Fungicide (Arysta Lifescience Benelux): Active ingredient: propamocarb hydrochloride 66.8%. /Propamocarb hydrochloride/|For more Formulations/Preparations (Complete) data for Propamocarb (10 total), please visit the HSDB record page.

Registration Notes: Outside USA: Previcur N for horticultural use. /Propamocarb hydrochloride/

A gas chromatography/nitrogen-phosphorus detection (GC/NPD) method is available for the enforcement of residues of propamocarb in plant commodities. ... An adequate liquid chromatography with mass spectrometry (LC/MS/MS) for the enforcement of residues of propamocarb and its metabolites in livestock commodities has be submitted to the Agency.|GC determination in food products.

Agrochemicals -> Fungicides|Fungicides

Computed Properties

Molecular Weight:188.27
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:188.152477885
Monoisotopic Mass:188.152477885
Topological Polar Surface Area:41.6
Heavy Atom Count:13
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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