DIELDRIN

CASRN: 60-57-1; DOT: 2761; DOT label: Poison; molecular formula: C12H8Cl6O; FW: 380.91; RTECS: IO1750000; Merck Index: 12, 3152 Physical state, color, and odor: 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). Melting point (°C): 175-176 (Weast, 1986) 143-144 (technical grade ≈ 90%, Aldrich, 1990) Boiling point (°C): Decomposes (Weast, 1986) Density (g/cm3): 1.75 at 20 °C (Weiss, 1986) Diffusivity in water (x 10-5 cm2/sec): 0.44 at 20 °C using method of Hayduk and Laudie (1974) Flash point (°C): Nonflammable (Weiss, 1986) Henry’s law constant (x 10-7 atm⋅m3/mol): 2 (Eisenreich et al., 1981) 580 at 25 °C (gas stripping-GC, Warner et al., 1987) 290 at 20 °C (Slater and Spedding, 1981) 100 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) 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) Bioconcentration factor, log BCF: 2.95 African catfish (Clarias gariepinus) (Lamai et al., 1999) 3.53 (B. subtilis, Grimes and Morrison, 1975) 4.25 (activated sludge), 3.36 (algae), 3.48 (golden ide) (Freitag et al., 1985)

3.46 Crassostrea virginica (quoted, Verschueren, 1983) 3.55 freshwater clam (Corbicula manilensis) (Hartley and Johnston, 1983) 3.65 (Pseudorosbora parva, Devillers et al., 1996) Soil organic carbon/water partition coefficient, log Koc: 4.11 (Batcombe silt loam, Briggs, 1981) 4.15 (clay loam, Travis and Arms, 1988) 4.73 (Taichung soil: pH 6.8, % sand: 25, % silt: 40, % clay: 35) (Ding and Wu, 1995) 4.37 (Beverly sandy loam), 4.42 (Plainfield sand), 4.44 (Big Creek sediment) (Sharom et al.,

1980a) Octanol/water partition coefficient, log Kow: 5.16 (Kishi et al., 1990) 6.2 at 20 °C (TLC retention time correlation, Briggs, 1981) 5.48 (Mackay, 1982) 4.49, 4.51, 4.55, 4.66 (shake flask-HPLC, Brooke et al., 1986) 3.692 (Rao and Davidson, 1980) 5.401 at 25 °C (shake flask-GLC, de Bruijn et al., 1989) 5.30 (estimated from HPLC capacity factors, Hammers et al., 1982) Solubility in organics: Soluble in ethanol and benzene (Weast, 1986) Solubility in water (µg/L): 200 at 20 °C (extraction-GLC, Weil et al., 1974) 186 at 25-29 °C (Park and Bruce, 1968) 200 at 26.5 °C (Bhavnagary and Jayaram, 1974) 90, 195, 400, and 600 at 15, 25, 35, and 45 °C, respectively (particle size ≤5 µm, Biggar and

Riggs, 1974) At 20-25 °C: 180 (particle size ≤5 µm), 140 (particle size ≤0.04 µm) (Robeck et al., 1965) 50 (Gile and Gillett, 1979) 250 at 20-25 °C (sand column-GC, Herzel and Murty, 1984) Vapor density (ng/L): 54 at 20 °C, 202 at 30 °C, 676 at 40 °C (gas saturation-GC, Spencer and Cliath, 1969) Vapor pressure (x 10-7 mmHg): 28 at 20 °C (gas saturation-GC, Spencer and Cliath, 1969) 100 at 30 °C (Tinsley, 1979) 7.78 at 20.25 °C (Gile and Gillett, 1979) 30.7 and 58.5 at 20 and 25 °C, respectively (gas saturation-GC, Grayson and Fosbraey, 1982) Environmental fate: Biological. Identified metabolites of dieldrin from solution cultures containing Pseudomonas sp. in soils include aldrin and dihydroxydihydroaldrin. Other unidentified by-products 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 dieldrin 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

to give syn-and anti-monodechlorodieldrin. Three isolates, Clostridium bifermentans, Clostridium glycolium, and Clostridium sp., were capable of dieldrin dechlorination but the rate was much lower than that of the mixed population (Maule et al., 1987). Using settled domestic wastewater inoculum, dieldrin (5 and 10 mg/L) did not degrade after 28 d of incubation at 25 °C in four successive 7-d incubation periods (Tabak et al., 1981). 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 degradation of dieldrin. Matsumura et al. (1970) reported microorganisms isolated from soil and Lake Michigan water converted dieldrin to photodieldrin. The percentage of dieldrin remaining in a Congaree sandy loam soil after 7 yr 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). Half-lives in soil ranged from 175 d to 3 yr (Howard et al., 1991; Jury et al., 1987). Groundwater. Dieldrin has a high potential to leach to groundwater (U.S. EPA, 1986). Surface Water. Mackay and Wolkoff (1973) estimated an evaporation half-life of 723 d from a surface water body that is 25 °C and 1 m deep. Hargrave et al. (2000) calculated BAFs as the ratio of the compound tissue concentration [wet and lipid weight basis (ng/g)] to the concentration of the compound dissolved in seawater (ng/mL). Average log BAF values for dieldrin in ice algae and phytoplankton collected from the Barrow Strait in the Canadian Archipelago were 4.99 and 5.24, respectively. Photolytic. Photolysis of a saturated aqueous solution of dieldrin by sunlight for 3 months resulted in a 70% yield of photodieldrin. The direct photolytic half-life under these conditions ranged from 1.8 to 2.1 months (Henderson and Crosby, 1968). A solid film of dieldrin exposed to sunlight for 2 months resulted in a 25% yield of photodieldrin (Benson, 1971). In addition to sunlight, UV light converts dieldrin to photodieldrin (Georgacakis and Khan, 1971). Solid dieldrin exposed to UV light (λ <300 nm) under a stream of oxygen yielded small amounts of photodieldrin (Gäb et al., 1974). Many other investigators reported photodieldrin as a photolysis product of dieldrin under various conditions (Crosby and Moilanen, 1974; Ivie and Casida, 1970, 1971, 1971a; Rosen and Carey, 1968; Robinson et al., 1976; Rosen et al., 1966). One of the photoproducts identified in addition to photodieldrin was photoaldrin chlorohydrin [1,1,2,3,-3a,5(or 6),7a-heptachloro-6-(or 5)-hydroxydecahydro-2,4,7-metheno-1H-cyclopenta[a]pentalene] (Lombardo et al., 1972). After a 1 h exposure to sunlight, dieldrin was converted to photodieldrin. Photodecomposition was accelerated by a number of photosensitizing agents (Ivie and Casida, 1971). When an aqueous solution containing dieldrin was photooxidized by UV light at 90-95 °C, 25, 50, and 75% degraded to carbon dioxide after 2.9, 4.8, and 12.5 h, respectively (Knoevenagel and Himmelreich, 1976). Chemical/Physical. The hydrolysis rate constant for dieldrin at pH 7 and 25 °C was determined to be 7.5 x 10-6/h, resulting in a half-life of 10.5 yr (Ellington et al., 1987). The epoxide moiety undergoes nucleophilic substitution with water forming dieldrin diol (Kollig, 1993). At higher temperatures, the hydrolysis half-lives decreased significantly. At 69 °C and pH values of 3.13, 7.22, and 10.45, the calculated hydrolysis half-lives were 19.5, 39.5, and 29.2 d, respectively (Ellington et al., 1986). Products reported from the combustion of dieldrin at 900 °C include carbon monoxide, carbon dioxide, HCl, chlorine, and unidentified compounds (Kennedy et al., 1972). At 33 °C, 35% relative humidity and a 2 mile/h wind speed, the volatility losses of dieldrin as a thick film, droplets on glass, droplets on leaves, and formulation film on glass after 48 h were 78.6, 70.3, 53.5, and 12.5%, respectively (Que Hee et al., 1975).