(1R,4S,4aS,5R,6R,7S,8S,8aR)1,2,3,-4,10,10-Hexachlor-6,7-epoxy-1,4,-4a,5,6,7,8,8a-octahydro-1,4:5,8-dimethanonaphthalin

Bezeichnung:(1R,4S,4aS,5R,6R,7S,8S,8aR)1,2,3,-4,10,10-Hexachlor-6,7-epoxy-1,4,-4a,5,6,7,8,8a-octahydro-1,4:5,8-dimethanonaphthalin

CAS-Nr60-57-1

Englisch Name:DIELDRIN

CBNumberCB6108911

SummenformelC12H8Cl6O

Molgewicht380.91

MOL-Datei60-57-1.mol

Synonyma

Dieldrin

(1R,4S,4aS,5R,6R,7S,8S,8aR)1,2,3,-4,10,10-Hexachlor-6,7-epoxy-1,4,-4a,5,6,7,8,8a-octahydro-1,4:5,8-dimethanonaphthalin

1,2,3,4,10,10-Hexachlor-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-endo-1,4-exo- 5,8-dimethanonaphthalin

(1R,4S,4aS,5R,6R,7S,8S,8aR)1,2,3,-4,10,10-Hexachlor-6,7-epoxy-1,4,-4a,5,6,7,8,8a-octahydro-1,4:5,8-dimethanonaphthalin physikalisch-chemischer Eigenschaften

Schmelzpunkt	143-144 °C(lit.)
Siedepunkt	496.11°C (rough estimate)
Dichte	1.75 g/cm3
Dampfdichte	13.2 (vs air)
Dampfdruck	30.7 and 58.5 at 20 and 25 °C, respectively (gas saturation-GC, Grayson and Fosbraey, 1982)
Brechungsindex	1.5550 (estimate)
Flammpunkt	2 °C
storage temp.	APPROX 4°C
Löslichkeit	Soluble in ethanol and benzene (Weast, 1986)
Wasserlöslichkeit	195ug/L(25 ºC)
Merck	3103
BRN	91396
Henry's Law Constant	27.6 at 5 °C, 63.2 at 15 °C, 82.9 at 20 °C, 97.7 at 25 °C, 217 at 35 °C:in 3% NaCl solution: 66.1 at 5 °C, 158 at 15 °C, 395 at 25 °C, 507 at 35 °C (gas stripping-GC, Cetin et al., 2006)
Expositionsgrenzwerte	NIOSH REL: TWA 0.25 mg/m3, IDLH 50 mg/m3; OSHA PEL: TWA 0.25 mg/m3; ACGIH TLV: TWA 0.25 mg/m3.
Stabilität	Stable. Breakdown product of aldrin in the environment. Incompatible with acids, active metals and strong oxidizing agents.
IARC	2A (Vol. 5, Sup 7, 117) 2019
EPA chemische Informationen	Dieldrin (60-57-1)

Sicherheit

Kennzeichnung gefährlicher	T+,N,Xn,F,T,Xi
R-Sätze:	25-27-40-48/25-50/53-36-20/21/22-11-39/23/24/25-23/24/25-67-65-38-51/53-52/53
S-Sätze:	22-36/37-45-60-61-36-26-16-62-7
RIDADR	UN 2811 6.1/PG 1
OEB	C
OEL	TWA: 0.25 mg/m3 [skin]
WGK Germany	3
RTECS-Nr.	IO1750000
HazardClass	6.1(a)
PackingGroup	II
HS Code	29104000
Giftige Stoffe Daten	60-57-1(Hazardous Substances Data)
Toxizität	LD50 orally in rats: 46 mg/kg (Gaines)
IDLA	50 mg/m3

Gefahreninformationscode (GHS)

DIELDRIN Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE KRISTALLE.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen unter Bildung giftiger Rauche mit Chlorwasserstoff. Reagiert mit Oxidationsmitteln und Säuren. Greift Metall an aufgrund der langsamen Bildung von Chlorwasserstoff bei Lagerung.
ARBEITSPLATZGRENZWERTE
TLV: 0,25 mg/m?(als TWA); Hautresorption; Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK: 0,25 mg/m?(Einatembare Fraktion), Spitzenbegrenzung: überschreitungsfaktor II(8); Hautresorption; (DFG 2007).
AUFNAHMEWEGE
Aufnahme in den Körper über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch beim Versprühen schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Möglich sind Auswirkungen auf das Zentralnervensystem mit nachfolgenden Krämpfen. ärztliche Beobachtung notwendig.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Die Substanz reichert sich im Körper an. Kumulative Wirkungen sind möglich: siehe AKUTE GEFAHREN/SYMPTOME.
LECKAGE
NICHT in die Kanalisation spülen. Verschüttetes Material in abdichtbaren Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. Persönliche Schutzausrüstung: Chemikalienschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät.
R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R27:Sehr giftig bei Berührung mit der Haut.
R40:Verdacht auf krebserzeugende Wirkung.
R48/25:Giftig: Gefahr ernster Gesundheitsschäden bei längerer Exposition durch Verschlucken.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R36:Reizt die Augen.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R11:Leichtentzündlich.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R67:Dämpfe können Schläfrigkeit und Benommenheit verursachen.
R65:Gesundheitsschädlich: kann beim Verschlucken Lungenschäden verursachen.
R38:Reizt die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S62:Bei Verschlucken kein Erbrechen herbeiführen. Sofort ärztlichen Rat einholen und Verpackung oder dieses Etikett vorzeigen.
S7:Behälter dicht geschlossen halten.
Beschreibung
Dieldrin is a colorless to light tan solid with amild chemical odor. The odor threshold in water is0.04 mg/L. Molecular weight=380.90; Boiling point =(decomposes); Freezing/Melting point=176.1℃; Vaporpressure=8 3 10 2 7 mmHg at 25℃. Hazard Identification(based on NFPA-704 M Rating System): Health 3,Flammability 0, Reactivity 0. Practically insoluble in water;solubility=0.02%.
Chemische Eigenschaften
Dieldrin is a colorless to light tan solid with a mild chemical odor. The Odor Threshold in water is 0.04 mg/L
Chemische Eigenschaften
white or light brown powder or crystals
Physikalische Eigenschaften
White crystals to pale tan flakes with an odorless to mild chemical odor. Odor threshold concentration is 41 μg/L (quoted, Keith and Walters, 1992).
Verwenden
Dieldrin was first used by cotton growers in the 1950s; it has subsequently been used on other crops for the control of vectorborne diseases and for mothproofing woolen goods. Dieldrin, as well as other cyclodiene insecticides, is uniquely suited for the control of termites. In 1974, the U.S. registration of products containing aldrin and dieldrin was canceled. As a result of worldwide concerns regarding the potential human health and environmental impacts of dieldrin, its manufacture ceased by the early 1990s.
Occupational exposures have occurred among all groups that have been involved in the manufacture or handling of the compound, and in the spraying of dieldrin suspensions and emulsions. Overexposure, resulting in acute intoxication, occurred primarily in the early days of dieldrin, aldrin, and endrin manufacture and in spraying operations with these compounds in Kenya, India, Iran, and other malariainfested countries.
Verwenden
Stereoisomer of Endrin. Used as an insecticide. Potential occupational carcinogen.
Verwenden
Formerly as insecticide.
Definition
ChEBI: Dieldrin is an organochlorine compound resulting from the epoxidation of the double bond of aldrin. It is the active metabolite of the proinsecticde aldrin. It has a role as a xenobiotic and a carcinogenic agent. It is an organochlorine insecticide, an organochlorine compound and an epoxide. It is functionally related to an aldrin.
Allgemeine Beschreibung
DIELDRIN is a light-tan flaked solid. DIELDRIN is insoluble in water. DIELDRIN is toxic by inhalation, skin absorption and ingestion. DIELDRIN can penetrate intact skin. DIELDRIN is used as an insecticide.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
DIELDRIN is sensitive to mineral acids, acid catalysts, acid oxidizing agents and active metals. DIELDRIN reacts with phenols. DIELDRIN is also slightly corrosive to metals. DIELDRIN may react vigorously with strong oxidizers such as chlorine and permanganates and strong acids such as sulfuric or nitric.
Health Hazard
Inhalation, ingestion, or skin contact causes irritability, convulsions and/or coma, nausea, vomiting, headache, fainting, tremors. Contact with eyes causes irritation.
Health Hazard
Highly toxic; toxic symptoms similar to theseof aldrin; affects central nervous system,liver, kidneys, and skin; causes headache,dizziness, nausea, vomiting, tremor, ataxia,clonic and tonic convulsions, and respiratoryfailure; oral LD50 value (mice): 38 mg/kg;causes liver cancers in animals; inadequateevidence in humans; RCRA Waste Number P037.
Exposure to many organochlorine pesticides has been linked to an increasedrisk of Parkinson’s disease. In this context,dieldrin has been the most implicated ofall. Dieldrin has been found, during postmortem, in the brain tissues of humanswith Parkinson’s disease, indicating that itpromotes dopaminergic degeneration. Various neurotoxic studies following exposure todieldrin have been conducted in both cellcultures and animal models. Such studiesindicated that dieldrin-induced neurotoxicity via mechanisms associated with dopaminergic degeneration including oxidative stress,mitochondrial dysfunction, protein aggregation, and apoptosis. Such effects cancause neuronal cell death and neurodegenerative diseases including Parkinson’s disease.Kanthasamy et al. (2005) have revieweddieldrin-induced neurotoxicity..
Brandgefahr
Special Hazards of Combustion Products: Toxic and irritating hydrogen chloride fumes may form in fire.
Landwirtschaftliche Anwendung
Insecticide: Manufacture in the United States prohibited since 1974. In 1987, EPA banned all uses. Banned for use in EU (also for export) All uses of dieldrin (and Aldrin) were canceled in 1974, except for subsurface ground insertion for termite control, dipping of non-food roots and tops, and moth-proofing by manufacturing processes in a closed system (EPA 1974). In 1987, these final three uses were voluntarily canceled by the sole manufacturer. Currently there are more than 25 global suppliers
Handelsname
ALVIT®; BELCO®[C]; COMPOUND 497®; D-31®; DIELDREX®; DIELDRITE®; ILLOXOL®; KILLGERM DETHLAC INSECTICIDAL LAQUER®; OCTALOX®; OXRALOX®; PANORAM®; PANORAM D-31®; PRENTOX®[C]; QUINTOX®; ROYAL BRAND®[C]; SD 3417®
Sicherheitsprofil
A human poison by ingestion and possibly other routes. Poison experimentally by inhalation, ingestion, skin contact, intravenous, and intraperitoneal routes. Experimental teratogenic and reproductive data. Absorbed readily through the skin and by other routes. It is a central nervous system stimulant. Questionable carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Human mutation data reported. An insecticide. Dieldrin is considerably more toxic than DDT by ingestion and skin contact. Dieldrin or its derivatives may accumulate in the body from chronic low dosages. When heated to decomposition it emits toxic fumes of Cl-. See also ALDRIN.
mögliche Exposition
Aldrin belongs to the group of cyclodiene insecticides. They are a subgroup of the chlorinated cyclic hydrocarbon insecticides which include DDT, BHC, etc. They were manufactured in the United States by Shell Chemical Co. until the United States Environmental Protection Agency prohibited their manufacture in 1974 under the Federal Insecticide, Fungicide, and Rodenticide Act. The primary use of the chemicals in the past was for control of corn pests, although they were also used by the citrus industry. Dieldrin’s persistence in the environment is due to its extremely low volatility (i.e., a vapor pressure of 1.78 3 1027 mmHg @ 20°C), and low solubility in water (186 μg/L @ 25°C29°C). In addition, dieldrin is extremely apolar, resulting in a high affinity for fat which accounts for its retention in animal fats, plant waxes; andother such organic matter in the environment. The fat solubility of dieldrin results in the progressive accumulation in the food chain which may result in a concentration in an organism which would exceed the lethal limit for a consumer.
Erste Hilfe
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 12 h afteroverexposure.
Carcinogenicity
Accumulating evidence suggests that dieldrin is “not a likely human carcinogen” and that it acts as a species-specific hepatocarcinogen in mice through nongenotoxic mechanisms.
The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for dieldrin is 0.25mg/m3 with a notation for skin absorption.
Environmental Fate
Biological. Identified metabolites of dieldrin from solution cultures containing Pseudomonas sp. in soils include aldrin and dihydroxydihydroaldrin. Other unidentified byproducts included a ketone, an aldehyde and an acid (Matsumura et al., 1968; Kearney and Kaufman, 1976). A pure culture of the marine alga, namely Dunaliella sp., degraded dieldrin to photodieldrin and an unknown metabolite at yields of 8.5 and 3.2%, respectively.
Photodieldrin and the diol were also identified as metabolites in field-collected samples of marine water, sediments and associated biological materials (Patil et al., 1972). At least 10 different types of bacteria comprising a mixed anaerobic population
Chacko et al. (1966) reported that cultures of six actinomycetes (Norcardia sp., Streptomyces albus, Streptomyces antibioticus, Streptomyces auerofaciens, Streptomyces cinnamoneus, Streptomyces viridochromogenes) and 8 fungi had no effect on the degradati
The percentage of dieldrin remaining in a Congaree sandy loam soil after 7 years was 50% (Nash and Woolson, 1967). Soil. Dieldrin is very persistent in soil under both aerobic and anaerobic conditions (Castro and Yoshida, 1971; Sanborn and Yu, 1973). Reported half-lives in soil ranged from 175 days to 3 years (Howard et al., 1991).75 days to 3 years (Howard et al., 1991). Groundwater. According to the U.S. EPA (1986) dieldrin has a high potential to leach to groundwater.
Photolytic. Photolysis of an aqueous solution by sunlight for 3 months resulted in a 70% yield of photodieldrin (Henderson and Crosby, 1968). A solid ?lm of dieldrin exposed to sunlight for 2 months resulted in a 25% yield of photodieldrin (Benso
Lager
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with dieldrinyou should be trained on its proper handling and storage.Dieldrin must be stored to avoid contact with oxidizers(such as perchlorates, peroxides, permanganates, chloratesand nitrates); strong acids (such as hydrochloric, sulfuric,and nitric); chemically active metals (such as potassium,sodium, magnesium, and zinc) since violent reactions occur.A regulated, marked area should be established where thischemical is handled, used, or stored in compliance withOSHA Standard 1910.1045.
Versand/Shipping
UN2761 Organochlorine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Toxicity evaluation
Consistent with its intended use on insects in soil, dieldrin is not very water soluble. However, dieldrin readily binds to sediment, but rarely leaches into deeper soil layers and groundwater. It takes decades to break down in the environment, and past agricultural uses of dieldrin have resulted in persisting soil residues and uptake in a wide range of crops.
The half-life of dieldrin in temperate soils is approximately 5 years, while it degrades faster (up to 90% in 1 month) from tropical soils.
Dieldrin may be volatilized from sediment and redistributed by air currents, contaminating areas far from their sources. Nationally, levels of dieldrin have declined since agricultural uses were discontinued.
Dieldrin readily bioaccumulates in terrestrial and aquatic organisms. Biomagnification factors ranging from 2.2 (in rainbow trout) to 16 (in herring gulls) have been reported for dieldrin. Bioconcentration factors for dieldrin in various aquatic organisms range from 400 to 68 000, indicating that dieldrin shows moderate to significant bioaccumulation in various aquatic species.
Inkompatibilitäten
Incompatible with strong acids: concentrated mineral acids; acid catalysts; phenols, strong oxidizers, active metals; like sodium, potassium, magnesium, and zinc. Keep away from copper, iron, and their salts.
Waste disposal
Incineration (816C, 0.5 second minimum for primary combustion; 1760C, 1.0 second for secondary combustion) with adequate scrubbing and ash disposal facilities. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≧100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal

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