Aldrin, Dieldrin, and Endrin

Aldrin, Dieldrin, and Endrin (Aldrex, Dieldrex, Endrex) 

IUPAC name Aldrin not less than 95% of 1,2,3,4,10,10-hexachloro- 

Molecular formula Ci2H8Cl60 Molecular formula CnHsCU Toxicity class USEPA II WHO lb 

Uses Aldrin, dieldrin, and endrin are the common names of three insecticides that are powerful and closely related chemically. Technical aldrin is a light tan to brown solid or powder. Aldrin is readily converted to dieldrin in the environment, and both are considered as closely related compounds by regulatory bodies. Their toxicities do not differ significantly. Aldrin and dieldrin were widely used from the 1950s to the early 1970s.14 

Aldrin has been used as a soil insecticide to control root worms, beetles, and termites. Dieldrin has been used in agriculture for soil and seed treatment and in public health to control disease vectors such as mosquitoes and tsetse flies. Dieldrin also has had veterinary use as a sheep dip and has been used in the treatment of wood and mothproofing woolen products. Workers could be occupationally exposed to aldrin or dieldrin from inhalation and absorption through the skin. Most uses for aldrin and dieldrin were banned in 1975 since 1986, these compounds have not been produced or imported into the United States. 

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Convulsions occurred within two hours following occupational exposure to aldrin, dieldrin and endrin (Hoogendam et al. 1962, 1965). After removal from exposure, seizures subsided and complete recovery was achieved in 1-3 days. Abnormal electroencephalograms (EEGs) were usually observed in endrin-poisoned workers, and sometimes occurred without any clinical symptoms. Predominately bilateral synchronous theta waves, and synchronous spike and wave complexes were seen (Hoogendam et al. 

Deichmann WB, MacDonald WE, Blum E, et al. 1970. Tumorigenicity of aldrin, dieldrin and endrin in the albino rat. Industrial Medicine 39 37-45. 

Ottolenghi AD, Haseman JK, Suggs F. 1974. Teratogenic effects of aldrin, dieldrin, and endrin in hamsters and mice. Teratology 9 11-16. 

Ressang AA, Titus I, Andar RS, et al. 1959. Aldrin, dieldrin and endrin intoxication in cats. Communicationes Veterinariae 2 71-88. 

Ribbens PH. 1985. Mortality study of industrial workers exposed to aldrin, dieldrin and endrin. Int Arch Occup Environ Health 56 75-79. 

There are only 18 priority pollutants commonly classified as pesticides. Only two are still in production heptachlor and chlordane. Aldrin, dieldrin, and endrin aldehyde are suspected as reaction byproducts in the endrin process. Heptachlor epoxide occurs as a reaction byproduct in both chlordane and heptachlor manufacturing. DDD, DDE, and DDT can occur as a reaction byproduct in the manufacture of endosulfan. 

In contrast to animal studies, epidemiological studies of workers employed in the manufacture of aldrin provide no conclusive evidence of carcinogenicity in humans. " One study of a cohort having mixed exposure to aldrin, dieldrin, and endrin found 9 deaths from cancer versus 12 expected. The workers had been exposed to the pesticides for a mean of 11 years and followed a mean of 24 years. A more recent examination of 2384 manufacturing workers, employed between 1952 and 1982, with exposure to a number of pesticides including aldrin found no excess mortality rates attributable to occupational exposures. Similarly, a 2 3-year follow-up of 570 aldrin- and dieldrin-exposed workers found no increase in overall mortality rates or mortality from liver cancer."... 

Epidemiological studies examining cancer mortality in workers exposed to dieldrin showed no conclusive evidence of carcinogenicity in humans. A study of 870 men employed in the manufacture of aldrin, dieldrin, and endrin found no increase in mortality from all cancers there were apparent increases in mortality from cancers of the esophagus, rectum, and liver based on very small numbers. In another report, follow-up of 232 workers with similar exposures revealed 9 cancer deaths with 12 expected. Updated epidemiological studies of manufacturing workers have confirmed the earlier findings. A cohort... 

All the chlorinated hydrocarbons belonging to this second group of compounds, once used in large amounts, have been banned for use in the U.S. since 1974. They are made by the Diels-Alder reaction, named after two chemists who won the Nobel Prize in 1950 for the discovery of this important reaction. The synthesis of the important insecticides chlordane, heptachlor, aldrin, dieldrin, and endrin are summarized in Fig. 20.4. 

Early studies of cyclodienes revealed reproductive effects on mice, rats, and dogs associated with changes in the estrus cycle (ref. 100, p. 154). Ottolenghi et al. (ref. 105) observed teratogenic effects on mice and hamsters at 1/2 LD q doses of aldrin, dieldrin and endrin. In addition to the anomalies observed (cleft palate, webbed feet and open eyes), growth retardation and fetal deaths occurred. Effects on the dams were not reported, but none of the expected overt toxic symptoms associated with chlorinated cycloalkenes was in evidence (ref. 105) ... 

Animal Care. Tests indef Dieldrin Animal-positive Aldrin Animal-Indefinite. E.J. Fairchild (Ed.), US-DHEW/PHS/CDC/NIOSH Cincinnati, OH 45226 (1977)-Ottolenghi, A.D., J.K. Haseman and F. Suggs, "Teratogenic Effects of Aldrin, Dieldrin and Endrin in Hamsters and Mice," Teratology. 9. 11-16 (Feb. 197 0-... 

The sensitivity range of these confirmatory chemical tests for aldrin, dieldrin, and endrin is 0.01 to 0.05 ppm in terms of the parent pesticides in field-treated samples (Table I). 

Ditraglia et al (61) also studied mortality experience in workers from the two plants involved in the study by Wang and MacMahon as well as two additional plants, one of which had manufactured aldrin, dieldrin and endrin. The other, discussed above, had manufactured only DDT. Mortality from all malignant neoplasms was less than expected, with SMR s from 0.73 to 0.91 for the three plants which had not manufactured DDT. Although... 

Aldrin and dieldrin in aqueous solutions were chemically oxidized in the presence of ozone or air (292). Aldrin, dieldrin, and endrin were catalytically decomposed when mixed with acid clays but not by neutral clays (287) aldrin was oxidized to dieldrin in soil systems (248, 249, 250). Barlow and Hadaway (275) found that dieldrin was not decomposed when it was applied to dried mud blocks. 

Toxaphene, lindane, chlordan, and heptachlor were adsorbed by soil particulate matter (158, 216, 255, 261, 268, 279, 291, 295, 299, 301, 302, 303, 304, 305) and volatilized from aqueous (292, 297) and soil (255, 264, 275, 280, 283, 293, 306) systems in a way analogous to that of aldrin, dieldrin, and endrin. Adsorption of the pesticides was most highly related to the organic matter content of soils and aquatic systems and probably occurred through weak physical intermolecular forces at lipophilic sites. Adsorbing and volatizing processes were involved in the fate of these compounds in aquatic and soil systems. Lindane was much more mobile in soil systems than the others (246, 255), probably because of its greater solubility (Table VI), and lindane and heptachlor volatilized much more readily from soils and aquatic systems (290, 292, 293, 296, 306). 

Sites contaminated by chlorinated pesticides (e.g. dichlorodiphenyltrichloroethane (DDT), aldrin, dieldrin, and endrin) and herbicides (e.g. atrazine, molinate and bentazone) due to agricultural activities and accidental spills have received little attention (Chapters 11 and 12). These contaminants are nonpolar in characteristics and sorb strongly to the soil. Similar to other hydrophobic organic compounds, desorption using solubilizing agents such as surfactants and cosolvents as well as... 

B. Skin absorption is a significant route of exposure, especially with aldrin, dieldrin, and endrin. Extensive or repeated (as little as 2 applications on 2 successive days) whole-body application of lindane to infants has resulted in seizures and death. 

The cyclodienes, particularly aldrin, dieldrin, and endrin, are considered unsafe for any kind of use. Lindane, on the other hand, has high selectivity in favour of Man. It is included in the World s principal pharmacopoeias as an insecticide, acaricide, and larvicide. A 0.2% alcoholic solution is applied topically for head lice and a 1 % emulsion is employed in the treatment of scabies, in humans. The use of DDT in human medicine, for similar purposes, has greatly diminished in the last decade. It must, however, be pointed out that it has a high safety record in Man, and that government bans on its use are concerned with its accumulation in the food chains of birds and fish where it interferes with the calcium metabolism of shells and bones, respectively (see p. 96). In 1956, Hayes, Durham and Cueto, of the USA Public Health Service, fed 35 mg of DDT per man per day (i.e. 200 times the highest average dietary intake of that time in the USA) to human volunteers for 18 months. None of the subjects developed any symptom related to this chemical. 

The lARC classified aldrin, dieldrin and endrin as Group 3 chemicals not classifiable as to their carcinogenicity to humans, but all the other chlorinated hydrocarbons (chlordane, heptachlor, mirex, toxaphene, hexachlorobenzene, pentachlorophenol and... 

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