Daminozide

160.17

160.17

216-485-9

F6KF33M5UB

DTXSID9020370

WHITE CRYSTALLINE SOLID

29280000

69.6

-1.5 at pH 5

Succinic acid 2,2-dimethylhydrazide appears as odorless white crystals or powder. (NTP, 1992)

1.2751 (rough estimate)

154-155 °C

286.06°C (rough estimate)

153.1±28.4 °C

1.4500 (estimate)

H2O: 100 g/L

2-8°C

2X10-4 mm Hg at 23 deg C

Oral-Rat LD50: 8400 mg/kg; Oral-Mouse LD50: 6300 mg/kg

Combustion produces toxic nitrogen oxide gas

Faint amine like odor

3.8 (5% aq soln)

Henry's Law constant= 4.2X10-10 atm-cu m/mole at 25 °C /Estimated/

pKa = 4.68

Hydroxyl radical reaction rate constant: 1.2X10-11 cu cm/molec-sec at 25 °C /Estimated/

Slightly soluble in water.

Acids, Carboxylic

SUCCINIC ACID 2,2-DIMETHYLHYDRAZIDE may be heat sensitive. Incompatible with strong oxidizing agents, strong acids, and bases. Also incompatible with wetting agents, alkaline materials, oils and copper-containing compounds. May corrode metals (NTP, 1992). May generate toxic gases with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. May generate flammable gases with alkali metals. Explosive reactions can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName Required.UN2811 (toxic solid, organic, n.o.s.)

2

40

36/37-24/25

WM9625000

Xn

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

Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, strong acids, wetting agents, oils, copper-containing compounds.

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

H315

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Incompatible with wetting agents, alkaline materials, oils, and copper-containing compounds.

Bioassay of Daminozide for Possible Carcinogenicity (1978) Technical Rpt Series No. 83 DHEW Pub No. NTIS No. PB285073/AS, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014|Toth B; Teratogenic Hydrazines: A Review. In Vivo 7 (1): 101-10 (1993). The review summarizes the results of 30 hydrazines, which were studied in humans and in six animal species for teratogenic activities. Of these, 23 chemicals were found to induce physical defects in the developing embryos of animals. Six hydrazines failed to induce teratogenic abnormalities in animals under the experimental conditions. Three hydrazine analogs, some of which were given in combination with other drugs to pregnant women, gave ambiguous results concerning teratogenic effects. ...|Alar (Daminozide): Agricultural Applications and Public Safety. March 1985-October 1989 (Citations from the BioBusiness Database). Govt Reports Announcements & Index (GRA&I), Issue 04 (1990). This bibliography contains citations concerning agricultural usage of the pesticide and growth regulator Alar (Daminozide), and the developing concern over public safety threatened by treated food crops. ... Contains 82 citations fully indexed and including a title list.|WHO/IPCS; Pesticide Residues in Food - 1991. Part II - Toxicology (1992)|For more Special Reports (Complete) data for DAMINOZIDE (6 total), please visit the HSDB record page.

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 5 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|...Vinyl coated hand protection, natural or reclaimed rubber protection, rubber aprons, and plastic eye and face protection... used when working with small quantities. Where possibility of gross splashing exists, full protective clothing made of rubber, neoprene or vinyl-coated materials should be worn. For respiratory protection in situations where recommended tolerance limits... exceeded, respiratory protective equipment... must be used. /Hydrazine and derivatives/

nontoxic

LD50 Rat oral 8,400 mg/kg|LD50 Rabbit percutaneous > 5000 mg/kg|LD50 Mouse oral 6300 mg/kg|LD50 Mouse ip 1325 mg/kg|LC50 Rat inhalation >20 mg/L/hr

A bioassay of daminozide ... for possible carcinogenicity was conducted by admin the test chemical in the diet to Fischer 344 rats and B6C3F1 mice. Groups of 50 rats and 50 mice of each sex were admin daminozide at one of two doses, either 5,000 or 10,000 ppm, for 104 wk, then observed for an additional wk. Matched controls consisted of 20 untreated males and 20 untreated females of each species. All surviving rats and mice were /sacrificed/ at 105 wk. ... It is concluded that under the conditions of this bioassay, daminozide was not carcinogenic in the male Fischer 344 rats or in the female B6C3F1 mice. In male B6C3F1 mice, the induction of hepatocellular carcinomas may have been associated with admin of the test chemical. Daminozide was carcinogenic in female Fischer 344 rats, inducing adenocarcinomas of the endometrium of the uterus and leiomyosarcomas of the uterus. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Positive; Male Mice: Equivocal; Female Mice: Negative.

Biological half-lives were significantly different among the three acetylation phenotypes (analysis of variance, P < 0.05): 3.94+/-1.70 hours for slow acetylators, 2.25+/-0.37 hours for intermediate acetylators, and 1.86+/-0.67 hours for rapid acetylators. /Hydrazine/

Daminozide's production may result in its release to the environment through various waste streams; it's use as a plant growth regulator(1,2) will result in its direct release to the environment(SRC). Prior use to improve the yield and quality of apples, cherries, and other fruits and vegetables has largely been curtailed because of perceived risks to children and other consumers(3). Owing to its use in greenhouses, nurseries, and other applications, daminozide is still one of the most heavily used plant growth regulators in the US(3).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a log Kow of -1.5(2) and a regression-derived equation(3), indicates that daminozide is expected to have very high mobility in soil(SRC). The pKa of daminozide is 4.68(2), suggesting that this compound will exist primarily as an anion in moist soil surfaces, and anions will not volatilize(SRC). Volatilization from dry soil surfaces is not expected(SRC) based upon a vapor pressure of 2X10-4 mm Hg(4). Daminozide is degraded in soil with a major degradation product of being unsymmetrical 1,1-dimethylhydrazide(5). In greenhouse studies, the persistence half-life of daminozide was found to range from 3 to 4 days in four different soils(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a log Kow of -1.5(2) and a regression-derived equation(3), indicates that daminozide is not expected to adsorb to suspended solids and sediment(SRC). The pKa of daminozide is 4.68(2), which suggests that this compound exists primarily as an anion in water surfaces and anions will not volatilize(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Soil studies under aerobic conditions suggest that this compound biodegrades rapidly(6,7), suggesting biodegradation under aerobic conditions in water may also be an important environmental fate process(SRC). No measurable hydrolysis of daminozide was noted at pH 5, 7, and 9(7), but sensitized photolysis was observed(8), suggesting that photolysis in sunlit surface waters may occur(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), daminozide, which has a vapor pressure of 2X10-4 mm Hg at 23 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase daminozide 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 32 hours(SRC), calculated from its rate constant of 1.2X10-11 cu cm/molecule-sec at 25 °C (SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor phase reaction of daminozide with photochemically produced hydroxyl radicals has been estimated to be 1.2X10-11 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 32 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). Daminozide was found to undergo a sensitized photooxidation via singlet oxygen(2); humic acid, red pigment isolated from apple peel, and rose bengal were found to be photosensitizers(2); in methanol solution, the photooxidation yielded succinic anhydride and N,N-dimethylnitrosamine(2); although photodegradation occurs, the importance of photooxidation via singlet oxygen in the environment is uncertain(2). No measurable hydrolysis was noted at pH 5,7, and 9 over 30 days, but it was shown that this compound degraded slowly (half-life >30 days) at pH 1, with 1,1-dimethylhydrazine produced as a degradation byproduct(3).

An estimated BCF of 3 was calculated for daminozide(SRC), using a log Kow of -1.5(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).

8.91 L/kg|The Koc of daminozide is estimated as 4(SRC), using a log Kow of -1.5(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that daminozide is expected to have very high mobility in soil(SRC).

The pKa of daminozide is 4.68(1), which indicates this compound will exist primarily as an anion in water and moist soil surfaces and anions will not volatilize. Daminozide is not expected to volatilize from dry soil surfaces based on its vapor pressure of 2X10-4 mm Hg at 23 °C(2).

Daminozide has been detected, by FDA's Pesticide Residue Monitoring Program, in U.S. foods during fiscal years 1978-1990(1-4); however, the concns and the frequencies of occurrence were not reported(1-4). The US Food and Drug Administration conducted a survey in 1986 to determine whether samples of fruits and fruit products contained residues of daminozide(5); max residue levels detected were as follows(5): 0.6 ppm in stored fresh apples, 0.8 ppm in applesauce, 1.1 ppm in apple juice, 3.6 ppm in frozen cherries, and 5.9 ppm in canned cherries(5); no detections (detection limit of 0.2 ppm) were found in grape juice samples(5).

Occupational exposure to daminozide occurs through dermal contact and inhalation of sprays, especially to workers using the compound as a plant growth regulator(1). Since daminozide has been detected in U.S. foods(2-3), exposure to the general population may occur through consumption of foods containing daminozide residues(SRC). Exposure to daminozide (and its degradation product 1,1-dimethylhydrazide) may have occurred via consumption of raw and processed agricultural commodities treated with daminozide(4).

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)|Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins. (See all compounds classified as Plant Growth Regulators.)

Daminozide has been studied in minipigs chosen because of the similar stomach conditions to the human. They were given oral doses of radio-labelled test material at 5 mg/kg bw. It was found to be rapidly excreted with approximately 60% excreted by 48 hours. The metabolite (UDMH) was found in urine at up to 2.8 ppm; lesser amounts were found in the feces. Radio-labelled 1,1-dimethylnitrosamine at levels of 0.69 ppm... were also found in the urine of the test animals. A second study was performed with a dermal application of radio-labelled daminozide covering dermal surfaces with concentrations of 0.5, 0.05, or 0.005 mg/cu cm for periods up to 24 hours. As much as 1.8% of the dose was absorbed and excreted by the test animals in 24 hours.|Distribution and metabolic fate of (14)C daminozide in Silver maple and American sycamore seedlings were studied by auto radiography. Radioactivity was detected in all parts of plant. (14)C concentrated in meristematic regions of leaves.|Analysis of extracts from red oak (Quercus rubra) administered (14)C-labeled maleic hydrazide or daminozide indicated that both growth inhibitors were distributed acropetally as well as basipetally over a 22 day period.|When leaves of 3 yr old apple trees, CV Cox's orange pippin, were painted with (14)C-labeled daminozide, over half of radioactivity accumulated in fruits.

Metabolites /in plants/ include 1,1-dimethylhydrazine.

The commercial product is contaminated with 0.005% /unsymmetrical dimethylhydrazine/.

SYMPTOMS: Symptoms of exposure to this compound may include convulsions, coma, liver and kidney damage and irritation to the gastrointestinal tract and respiratory tract. ACUTE/CHRONIC HAZARDS: This compound is harmful if swallowed, inhaled or absorbed through the skin. It may cause irritation to the gastrointestinal tract and respiratory tract. When heated to decomposition it may emit toxic fumes of carbon monoxide, carbon dioxide and NOx. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

Basic treatment: Establish a patent airway. 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 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 normal saline 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 ... . Cover skin burns with dry, sterile dressings after decontamination ... . /Hydrazine 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 respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam ... . Monitor for signs of hypoglycemia (decreased level of consciousness, tachycardia, pallor, dilated pupils, diaphoresis, and/or a dextrose strip or glucometer reading less than 50 mg/dl) and administer 50% dextrose if necessary. Draw blood sample before administration ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Hydrazine and Related Compounds/

Alar-85

... B-Nine (Uniroyal) is a special 5% active liquid formulation for ornamentals; rates of 1000-7500 ppm are recommended. Alar (Uniroyal) is an 85% active water-sol powder. Rates of 500-5000 ppm are recommended. Do not mix with other pesticides.|Water soluble powder.

Former use as a plant growth regulating agent used in orchard crops. The registrant, Uniroyal Chemical Company, voluntarily cancelled all food use registrations of daminozide on November 14, 1989 and EPA revoked the tolerances for food uses in March 1990.|/SRP: Former use/ recommended for use on many ornamentals and fruits. Dicots respond better than monocots.|Prior use to improve the yield and quality of apples, cherries, and other fruits and vegetables has largely been curtailed because of perceived risks to children and other consumers. Owing to its use in greenhouses, nurseries, and other applications, daminozide is still one of the most heavily used plant growth regulators in the US.

PRODUCT ANALYSIS IS BY BROMIDE/BROMIDE TITRATION. RESIDUES MAY BE DETERMINED BY GLC OF A DERIVATIVE OR BY ALKALINE HYDROLYSIS TO LIBERATE 1,1-DIMETHYLHYDRAZINE WHICH IS DETERMINED COLORIMETRICALLY.|ASSAY: DETERMINED BY NEUTRALIZATION EQUIVALENT AND MELTING POINT RANGE.|RESIDUE: COLORIMETRIC METHOD FOR DIMETHYL HYDRAZINE, AFTER HYDROLYSIS OF ALAR.|DAMINOZIDE IN FOOD WAS DETERMINED BY GLC AFTER ALKALINE HYDROLYSIS TO DIMETHYLHYDRAZINE. RECOVERIES FROM SAMPLES SPIKED WITH 0.10-40 PPM WERE GREATER THAN 80%. 1,1-DIMETHYLHYDRAZINE WAS DETERMINED IN APPLES. DAMINOZIDE DECOMP TO DIMETHYLHYDRAZINE WHEN BOILED IN APPLE HOMOGENATE.|Analysis for daminozide in apple juice by anion exchange chromatography/particle beam MS.

Agrochemicals -> Plant Growth Regulators|Pharmaceuticals|Environmental transformation -> Pesticides (parent, predecessor)

Daminozide has known environmental transformation products that include formaldehyde.