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HCID 15331Erstellt: 25. Oktober 2026

Daminozide

https://huagongshe.com/de/chemical/15331

Molekülstruktur von Daminozide

Identifikatoren & physikalische Daten

CAS No.1596-84-5
SummenformelC6H12N2O3
Durchschnittliche Molmasse160,17 g/mol
Monoisotopische Masse160,08479224 g/mol
SMILESCN(C)NC(=O)CCC(=O)O
InChIKeyNOQGZXFMHARMLW-UHFFFAOYSA-N
PubChem CID15331
ChEMBLCHEMBL2164243
ChEBICHEBI:4312
EC No.216-485-9
DTXSIDDTXSID9020370

Chemische & physikalische Eigenschaften

XLogP-3,1
Polarare Oberfläche (TPSA)69,6
H-Brücken-Donoren2
H-Brücken-Akzeptoren4
Frei drehbare Bindungen4
Schwere Atome11
Formalladung0
Komplexität156
pH3.8 (5% aq soln)
SpringerMaterials PropertiesFusion temperature
PestizidePesticide -> EPA IRISAgrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: ApprovedPesticides -> Plant Growth RegulatorsEnvironmental transformation -> Pesticides (parent, predecessor)
LogP (Verteilungskoeffizient)log Kow = -1.5 at pH 5,7, and 9 @ 21 °C
GeruchFaint amine like odor
Color/FormWHITE CRYSTALLINE SOLID
Löslichkeit1 to 10 mg/mL at 75 °F (NTP, 1992)25 g/kg acetone50 g/kg methanolit is insol in simple hydrocarbonsIn water, 1X10+5 mg/L at 25 °C
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Schmelzpunkt309 to 311 °F (NTP, 1992)154-155 °C
Dampfdruckless than 0.0000750 mmHg at 68 °F (NTP, 1992)0.0002 [mmHg]2X10-4 mm Hg at 23 °C

Sicherheit & Vorschriften

GHS-EinstufungWarningH351: 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.H315 (14.3%): Causes skin irritation [Warning Skin corrosion/irritation]
Regulatorische InformationenHazard Traits - CarcinogenicityDaminozide 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) 2018/1262Daminozide: Does not have an individual approval but may be used under an appropriate group standard
Weitere SicherheitsinformationenIMAP assessments - Butanedioic acid, mono(2,2-dimethylhydrazide): Environment tier I assessment
BrandgefahrenFlash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)
GesundheitsgefahrenSYMPTOMS: Symptoms of exposure to this compound may include convulsions, coma, liver and kidney damage and irritation to the gastrointestinal tract and respiratory tract.
GefahrenübersichtSymptoms 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.
Reaktive GruppeAcids, Carboxylic
Special ReportsBioassay 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 20014Toth BTeratogenic 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/IPCSPesticide Residues in Food - 1991. Part II - Toxicology (1992)For more Special Reports (Complete) data for DAMINOZIDE (6 total), please visit the HSDB record page.
FIFRA-AnforderungenAs 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: 0032Pesticide type: herbicide (growth regulator)Registration Standard Date: 06/30/84 PB87-104782Case Status: RED Approved 09/93OPP 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): daminozideAI 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.
Reactivity ProfileSUCCINIC 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.
Air and Water ReactionsSlightly soluble in water.
Hazard Classes and CategoriesSkin Irrit. 2 (14.3%)Carcinogenicity - Category 2Carc. 2
Hazardous Reactivities and IncompatibilitiesIncompatible with wetting agents, alkaline materials, oils, and copper-containing compounds.
BrandbekämpfungFires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Erste HilfeEYES: 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.
Freisetung ohne BrandSMALL 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.
EntsorgungsverfahrenSRP: 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
Personal Protective Equipment (PPE)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/
ÖkotoxizitätswerteLC50 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.
UmweltverhaltenTERRESTRIAL 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).
LebensmitteluntersuchungswerteDaminozide 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).
Unerwünschte WirkungenNeurotoxin - Other CNS neurotoxin
Ongoing Test StatusThe 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]
EPA IRIS InformationAlar1.5 x 10 ^-1 mg/kg-day
Soil Adsorption/MobilityThe 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).
Artificial Pollution SourcesDaminozide's production may result in its release to the environment through various waste streamsit'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).
Environmental BiodegradationN-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).
Carcinogen ClassificationDaminozideTR-083: Bioassay of Daminozide for Possible Carcinogenicity (CASRN 1596-84-5) (1978 )03/07/78No EvidenceClear EvidenceEquivocal Evidence
Environmental BioconcentrationAn 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).
Volatilization from Water/SoilThe 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).