309-00-2

Usage

Uses

Used in Agriculture:
ALDRIN was formerly used as an insecticide for soil insects and the control of termites around buildings. It was also employed in the control of various pests in agricultural settings.
Used in Industrial Applications:
Industrial exposures to ALDRIN occurred among groups involved in its manufacture, as well as in the handling and spraying of suspensions and emulsions of the compound.
Used as a Fumigant:
ALDRIN was also used as a fumigant in the past, but its manufacture and use have been discontinued in the U.S. due to its classification as a persistent organic pollutant.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

ALDRIN may be sensitive to prolonged exposure to light. ALDRIN is stable to heat and in the presence of inorganic and organic bases. ALDRIN is stable to hydrated metal chlorides and mild acids. ALDRIN is thermally stable up to 392° F and ALDRIN is stable between pH 4 and 8. ALDRIN reacts with concentrated acids and phenols in the presence of oxidizing agents. ALDRIN can be corrosive to metals. ALDRIN can react with acid catalysts, acid oxidizing agents and active metals.

Hazard

Toxic by skin absorption. Central nervous system impairment, and liver and kidney damage. Questionable carcinogen.

Health Hazard

Poisoning by aldrin usually involves convulsions due to its effects on the central nervous system. Reproductive effects and liver effects have also been reported. It is classified as an extremely toxic chemical. Probable oral lethal dose for humans is between 7 drops and one oz. for a 150 lb. adult human. Conflicting reports of carcinogenicity of ALDRIN remain an area of controversy. Similar chemically and toxicologically to dieldrin.

Health Hazard

Highly toxic to humans and animals by allroutes of exposure; absorbed through skin aswell; toxic symptoms — headache, dizziness,nausea, vomiting, tremor, ataxia, convulsions, central nervous system depression, andrespiratory failure; also causes renal damage; oral LD50 value 30–100 mg/kg in mosttest animals metabolizes to dieldrin; oraladministration in rats and mice increased theincidence of liver and lung cancer, carcinogenicity: animal and human evidence inadequate; exposure limit 0.25 mg/m3 (skin)(ACGIH); RCRA Waste Number P004.

Fire Hazard

When heated to decomposition, ALDRIN emits toxic fumes of chlorine containing compounds. Commercial solutions may contain flammable or combustible liquids. The dry powder will not burn. Container may explode in heat of fire. Avoid concentrated mineral acids, acid catalysts, acid oxidizing agents, phenols, or active metals.

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by ingestion, skin contact, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: excitement, tremors, and nausea or vomiting. An experimental teratogen. Other experimental reproductive effects. Continued acute exposure causes liver damage. Human mutation data reported. See also CHLORINATED HYDROCARBONS. When heated to decomposition it emits toxic fumes of Cl-.

Carcinogenicity

Rodent carcinogenicity evaluations of aldrin have been extensively reviewed, with the conclusion that the mouse-specific hepatocarcinogenic activity of aldrin occurs through a nongenotoxic mode of action involving promotion of spontaneously initiated liver cells.

Environmental Fate

Biological. Dieldrin is the major metabolite formed from the microbial degradation of aldrin via epoxidation (Lichtenstein and Schulz, 1959; Korte et al., 1962; Kearney and Kaufman, 1976). Microorganisms responsible for this reaction were identified as Aspergillus niger, Aspergillus flavus, Penicillium chrysogenum and Penicillium notatum (Korte et al., 1962). Dieldrin may further degrade to photodieldrin (Kearney and Kaufman, 1976). A pure culture of the marine alga namely Dunaliella sp. degraded aldrin to dieldrin andthe diol at yields of 23.2 and 5.2%, respectively (Patil et al., 1972). In four successive 7- day incubation periods, aldrin (5 and 10 mg/L) was recalcitrant to degradation in a settled domestic wastewater inoculum (Tabak et al., 1981). In a mixed microbial population under anaerobic conditions, nearly all aldrin (87%) degraded to two unidentified products in 4 days (Maule et al., 1987)Soil. Patil and Matsumura (1970) reported 13 of 20 soil microorganisms were able to degrade aldrin to dieldrin under laboratory conditions. Harris and Lichtenstein (1961) studied the volatilization of aldrin (4 ppm) in Plainfield sand and quartzAldrin was found to be very persistent in an agricultural soil. Fifteen years after application of aldrin (20 lb/acre), 5.8% of the applied dosage was recovered as dieldrin and 0.2% was recovered as photodieldrin (Lichtenstein et al., 1971).Plant. Photoaldrin and photodieldrin formed when aldrin was codeposited on bean leaves and exposed to sunlight (Ivie and Casida, 1971). Dieldrin and 1,2,3,4,7,8-hexachloro-1,4,4a,6,7,7a-hexahydro-1,4-endo-methyleneindene-5,7-dicarboxylic acid were identified in aldrin-treated soil on which potatoes were grown (Klein et al., 1973)Surface Water. Under oceanic conditions, aldrin may undergo dihydroxylation at the chlorine free double bond to produce aldrin diol (Verschueren, 1983). When raw water obtained from the Little Miami River in Ohio containing aldrin (10 μg/L) was p

Solubility in organics

50 g/L in alcohol at 25 °C (quoted, Meites, 1963); very soluble (>600 mg/L) in acetone, benzene, xylenes (Worthing and Hance, 1991), and many chlorinated hydrocarbons such as chloroform, carbon tetrachloride, etc.

Solubility in water

50 g/L in alcohol at 25 °C (quoted, Meites, 1963); very soluble (>600 mg/L) in acetone, benzene, xylenes (Worthing and Hance, 1991), and many chlorinated hydrocarbons such as chloroform, carbon tetrachloride, etc.

Toxicity evaluation

Consistent with its intended use on insects in soil, aldrin is not very water soluble. It binds to sediment, but rarely leaches into deeper soil layers and groundwater. Aldrin is volatile and readily degrades to dieldrin in the environment. When aldrin is applied to silty loam soil, the amount detectable in 1.7 years will have declined by 25% of the amount applied. Aldrin is estimated to have a half-life in soil of 1.5–5.2 years, depending on the composition of the soil.Persistence is defined in terms of the half-life of a substance in the soil. For aldrin, this has been determined to be 2–15 years. Aldrin is largely converted via biological or abiotic mechanisms to dieldrin, which is significantly more persistent. Both aldrin and dieldrin are absorbed into the food chain. Residues may remain in the soil for a long period, if contaminated plant and animal materials are added to the topsoil. Aldrin and dieldrin are retained in the fatty materials of sewage sludge, and in fish emulsions used as fertilizers. Topical soil application of these materials makes these compounds available to grazing animals, which ingest some soil when they crop grass. Aldrin may be volatilized from sediment, and redistributed by air currents, contaminating distant areas. Nationally, levels of aldrin have declined since agricultural uses were discontinued.

InChI:InChI=1/C12H8Cl6/c13-8-9(14)11(16)7-5-2-1-4(3-5)6(7)10(8,15)12(11,17)18/h1-2,4-7H,3H2/t4-,5+,6+,7-,10+,11-

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 74-86-2 acetylene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 77-47-4 hexachlorocyclopentadiene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 25578-04-5 (1α,4α,4aα,9β,9aα,10β)-1,4,4a,9,9a,10-hexahydro-1,4:9,10-dimethanoanthracen-12-one 

Downstream Products

• 5103-66-2 4.5.6.7.8.8.-Hexachlor-4,7-methano-3a,4,7,7a-tetrahydro-indan-dicarbonsaeure-(1,3) 
• 74415-96-6 endo-6-Chlor-exo-7-trichlormethyl-6,7-dihydro-aldrin 
• 74415-97-7 C₂₀H₁₂Cl₆O₄ 
• 60-57-1 dieldrin 
• 2387-13-5 dihydroaldrin 
• 15914-95-1 exo-endo-tetracyclo<6.2.1.1^3,6.0^2,7>dodecane 
• 22398-50-1 endo,exo-3,4,5,6-tetrachlorotetracyclo<6.2.1.1^3,6.0^2,7>dodeca-4,9-diene 
• 23421-66-1 1,1,2,3,3a,7a-hexachloro-2,3,3a,3b,4,6a,7,7a-octahydro-2,4,7-metheno-1H-cyclopenta[a]pentalene 

Relevant academic research and scientific papers

CYCLOADDITIONS OF HEXACHLOROCYCLOPENTADIENE TO 7-SUBSTITUTED NORBORNADIENES: REMOTE SUBSTITUENT EFFECTS ON REACTIVITY AND STEREOSELECTIVITY

The rates and stereoselectivities of the cycloadditions of hexachlorocyclopentadiene to norbornadienes substituted at the 7-position by tert-butyl, trimethylsilyl, methoxy, acetoxy, hydroxy, methoxymethyl, and methoxycarbonyl groups have been measured.The rates correlate with substituent electronegativities.

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

Physical, chemical, and isotopic (atomic) labels

Chemical or isotopic labels are added to, e.g., a potentially lethal drug formulation, to generate a unique chemical fingerprint. Combinations of chemical additives are mixed with the drug to aid in their isolation and identification, especially when such drugs are used for illicit purposes. When stable isotopes are incorporated into lethal drugs, the labeling process conveys a very unique internal chemical signature and greatly aids in the identification of the parent drug in body fluids and tissues. When heath-care providers become aware that certain drugs can now be easily tracked and identified in a victim, individuals may be reluctant to utilize these agents for ill purposes.

Transannular orbital interaction between ketone and olefin chromophores detected by circular dichroism and13C-NMR spectroscopy. Dimethanonaphthalenones and trimethanoanthracenones

A series of δ,ε-unsaturated ketones and their saturated ketone analogs were synthesized on the dimethanonaphthalene skeleton with endo-endo (1), endo-exo (2), and exo-exo (3) configurations. The corresponding norbornylogs (trimethanoanthracenes) with ζ,η-unsaturated ketones (4, 5, and 6) and their saturated analogs were also synthesized. Their 13C-NMR and circular dichroism (CD) spectra were measured in order to examine transannular orbital interactions. Transannular orbital interaction was detected by a relatively more shielded 13C=O resonance in the unsaturated ketones. The shielding was largest when the C=O and C=C chromophores could interact through ρ-pp orbital overlap, as in 1. That is, orbital interaction through space is an important component of the ground state of 1. In the CD spectra, the ketone n-π* Δεmax values were typically larger for the unsaturated ketones, as compared with their saturated ketone analogs. The n-π* Δεmax enhancements fall off with increasing interchromophoric distance, as seen in the trimethanoanthracenes. The presence of "charge-transfer" CD bands near 230 nm in the unsaturated ketones suggests a component of "through-space" orbital interaction. The intensity of the CD charge-transfer bands is greatest when the chromophores are oriented for ρ-pp orbital interaction. Orbital interaction through space appears to be an important component of the excited state of 1 and 2, and even 4, but it appears to play a less important role in 3, 5, and 6.