Daminozide

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticides -> Plant Growth Regulators

Environmental transformation -> Pesticides (parent, predecessor)

1 to 10 mg/mL at 75 °F (NTP, 1992)

25 g/kg acetone; 50 g/kg methanol; it is insol in simple hydrocarbons

In water, 1X10+5 mg/L at 25 °C

309 to 311 °F (NTP, 1992)

154-155 °C

less than 0.0000750 mmHg at 68 °F (NTP, 1992)

0.0002 [mmHg]

2X10-4 mm Hg at 23 °C

Warning

H351: Suspected of causing cancer [Warning Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 2.9% (1 of 35) of reports.

Warning

H315 (14.3%): Causes skin irritation [Warning Skin corrosion/irritation]

Hazard Traits - Carcinogenicity

Daminozide is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

05/53/EC, Reg. (EU) 2017/1511, Reg. (EU) 2019/1589, Reg. (EU) 2020/1511, Reg. (EU) 2021/1449, Reg. (EU) 2022/1480, Reg. (EU) 2023/1757, Reg. (EU) 2025/1489, Reg. (EU) 2026/1826, Reg. (EU) No 533/2013, Reg. (EU) No 540/2011, Reg.(EU) 2018/1262

Daminozide: Does not have an individual approval but may be used under an appropriate group standard

Symptoms of exposure to this compound may include convulsions, coma, liver and kidney damage and irritation to the gastrointestinal tract and respiratory tract. [CAMEO] May cause irritation; [MSDSonline] Unsymmetrical dimethylhydrazine is a metabolite in the body; [Reference #1] See 1,1-Dimethylhydrazine.

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.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Daminozide is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0032; Pesticide type: herbicide (growth regulator); Registration Standard Date: 06/30/84 PB87-104782; Case Status: RED Approved 09/93; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): daminozide; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Based on reviews of the generic data for the active ingredient daminozide, the Agency has sufficient information on the health effects of daminozide and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency concludes that products containing daminozide for use in enclosed commercial structures such as greenhouses, shadehouses and interiorscapes are eligible for reregistration. The Agency has determined that daminozide products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment.

Criteria of Concern: Oncogenicity. Action/Use Affected: Cancelled, all daminozide products, for food uses. Remaining registrations for nonfood uses include cut chrysanthemums and bedding plants. Special review of nonfood uses continued, pending an evaluation of the cancer studies in rats and mice with unsymmetrical dimethyl hydrazine, a degradate and metabolite of daminozide.

Existing Stocks Provisions: The sale, distribution, shipment, and use of existing stocks of daminozide for food uses is prohibited in the USA.

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.

Skin Irrit. 2 (14.3%)

Carcinogenicity - Category 2

Carc. 2

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.

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.

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.

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/

LC50 Rainbow trout 149 mg/L/96 hr /Conditions of bioassay not specified/

LC50 Bluegill sunfish 423 mg/L/96 hr /Conditions of bioassay not specified/

LD50 Mallard duck oral >2250 mg/kg /Technical daminozide/

LC50 Mallard duck dietary >10000 ppm duration of 8 days /technical daminozide/

For more Ecotoxicity Values (Complete) data for DAMINOZIDE (8 total), please visit the HSDB record page.

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).

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).

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=1596-84-5]

Alar

1.5 x 10 ^-1 mg/kg-day

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).

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).

N-METHYL-(14)C-LABELED ALAR ... APPLIED TO 4 SOILS UNDER GREENHOUSE CONDITIONS. ... MICROBIAL DEGRADATION ... MAJOR ROUTE OF ... DISSIPATION FROM SOIL. ... HALF LIFE OF ALAR WAS 3 TO 4 DAYS ON ALL SOILS & MAJOR DEGRADATION PRODUCT WAS (14)CO2. IN 14 DAYS, ABOUT 84% OF LABEL ... RECOVERED AS (14)CO2 ... REMAINDER ... ASSOC WITH SOIL ORG MATTER.

In soil incubation studies using a sterile and non-sterile sandy loam soil, (14)C labelled daminozide degraded much more rapidly in the non-sterile soil indicating that microbial degradation was the major route of dissipation in the soil(1); in the sterile soil, only 0.2% of applied daminozide was recovered as (14)CO2 after 10 days of incubation while in the non-sterile soil, 75.4% was recovered as (14)CO2 after 14 days(1). The half-life of daminozide in soil under aerobic conditions was reported as 9.5 hours with formaldehyde detected as the only identifiable degradate(2).

Daminozide

TR-083: Bioassay of Daminozide for Possible Carcinogenicity (CASRN 1596-84-5) (1978 )

03/07/78

No Evidence

Clear Evidence

Equivocal Evidence

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).

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).

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Daminozide is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0032; Pesticide type: herbicide (growth regulator); Registration Standard Date: 06/30/84 PB87-104782; Case Status: RED Approved 09/93; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): daminozide; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Based on reviews of the generic data for the active ingredient daminozide, the Agency has sufficient information on the health effects of daminozide and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency concludes that products containing daminozide for use in enclosed commercial structures such as greenhouses, shadehouses and interiorscapes are eligible for reregistration. The Agency has determined that daminozide products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment.

Criteria of Concern: Oncogenicity. Action/Use Affected: Cancelled, all daminozide products, for food uses. Remaining registrations for nonfood uses include cut chrysanthemums and bedding plants. Special review of nonfood uses continued, pending an evaluation of the cancer studies in rats and mice with unsymmetrical dimethyl hydrazine, a degradate and metabolite of daminozide.

Existing Stocks Provisions: The sale, distribution, shipment, and use of existing stocks of daminozide for food uses is prohibited in the USA.

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

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.

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.

Used as a systemic plant growth regulator on ornamentals and bedding plants in enclosed structures such as greenhouses, shadehouses, and interiorscapes; [HSDB] Registered for use on ornamentals in greenhouses; [Reference #1]

All food uses voluntarily cancelled in 1989; [Reference #1]

Farming (Pesticides) [Category: Industry]

For daminozide (USEPA/OPP Pesticide Code: 035101) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Daminozide is a systemic growth regulator registered for use on ornamentals, including potted chrysanthemums and poinsettias, and bedding plants in enclosed structures such as greenhouses, shadehouses and interiorscapes.

A plant growth regulating agent used in orchard crops and ornamentals.

... 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.

Pharmaceuticals

Environmental transformation -> Pesticides (parent, predecessor)

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.