Chlorinated aldrin

Polychlorinated Pesticides. A once substantial but now diminished use for DCPD is in the preparation of chlorinated derivatives for further use or synthesis into pesticide compounds (see Insectcontrol technology). Soil permanence and solubiUty of the products in human fatty tissues have considerably restricted the use of these compounds. The more prominent chlorinated pesticides were aldrin, dieldrin, chlordane, and heptachlor, all of which use hexachorocyclopentadiene as a starting material. Aldrin and dieldrin are no longer used in the U.S. Chlordane and heptachlor are stiU produced, but only for export use. 

Aldrin, a chlorinated insecticide now banned for use in the United States, can be made by Diels-Alder reaction of hexachloro-l,3-cyclopentadiene with norbomadicne. What is the structure of aldrin ... 

Halogen-containing substances e. g. chlorine-containing insecticides [1, 7] such as aldrin, dieldrin, DDT, perthane,... 

Aspila et al. [338] reported the results of an interlaboratory quality control study in five laboratories on the electron capture gas chromatographic determination of ten chlorinated insecticides in standards and spiked and unspiked seawater samples (lindane, heptachlor, aldrin, 5-chlordane, a-chlordane, dield-rin, endrin, p, p -DDT, methoxychlor, and mirex). The methods of analyses used by these workers were not discussed, although it is mentioned that the methods were quite similar to those described in the water quality Branch Analytical Methods Manual [339]. Both hexane and benzene were used for the initial extraction of the water samples. 

Rachel Carson s book Silent Spring that was published in 1962, was the first popular work to bring the uncontrolled environmental contamination by pesticides to public attention. Well-publicized and well-organized campaigns were mounted in several countries to prohibit the use of DDT and other persistent chlorinated insecticides such as Aldrin and heptachlor. Governments in many developed countries like USA,... 

Terrence Collins is the Thomas Lord Professor of Chemistry at Carnegie Mellon University who contends that the dangers of chlorine chemistry are not adequately addressed by either academe or industry, and alternatives to chlorine and chlorine processors must be pursued. He notes, Many serious pollution episodes are attributable to chlorine products and processes. This information also belongs in chemistry courses to help avoid related mistakes. Examples include dioxin-contaminated 2,4,5-T, extensively used as a peacetime herbicide and as a component of the Vietnam War s agent orange chlorofluorocarbons (CFCs) polychlorinated biphenyls (PCBs the pesticides aldrin, chlordane, dieldrin, DDT, endrin, heptachlor, hexachlorobenzene, lindane, mirex, and toxaphene pentachlorophe-... 

Novikova [21] has reviewed the literature (209 references) covering the extraction, clean-up and analysis of organochlorine (and organophosphorus) insecticides in soil. Johnson and Starr [22] and Chiba and Morley [4] have studied factors affecting the extraction of Dieldrin and Aldrin from different soil types ultrasonic extraction was recommended by these workers. Lopez-Avila et al. [23] used microwave assisted extraction to extract chlorinated insecticides from soils. 

Using the gas chromatography methods Sackmayereva et al. [30] obtained from spiked samples the four BHC isomers at 93-103.5% recovery. Both DDT and DDE were yielded in 85.6-94%, 90-93.2%, 90-102.4% and 92-105.8% from sediment. Purification on a Florisil column was used in determining chlorinated insecticides unstable at low pH (Aldrin, Dieldrin). The type and activity of Florisil influence the yield and accuracy of the method. Therefore, the activity of this adsorbent had to be verified and adjusted [36, 37],... 

The procedure described by Suzuki et al. [11, 12], discussed in section 9.1.1.1 for the determination of chlorinated insecticides in soils has also been applied to hexane extracts of river sediments using high-resolution gas chromatography with glass capillary columns. Minimum detectable levels of a-BHC, fs-BHC, -BHC, P-BHC, Heptachlor, Heptachlor epoxide, Aldrin, Dieldrin, Endrin, p,p -DDE, p,p -TDE and p,p -DDT in lOOg samples of bottom sediment were 0.0005, 0.0032, 0.0014, 0.0040, 0.0012, 0.0020, 0.0014, 0.0020, 0.0056, 0.0032, 0.0080 and 0.0120mg kgr1 respectively. 

Estimated half-lives for chlorinated hydrocarbon pesticides vary widely [16, 22] Aldrin, 1-9 Dieldrin, 3-7 Chlordane, 1-8 Heptachlor, 1-4 and DDT, 3-10 years. Half-lives for PCBs range from one year to 16 years [23]. Other types of pesticides, e.g. organophosphates, triazines, carbamates and ureas, are generally less persistent [16, 24],... 

Very little recent information on concentrations of endrin in water could be found in the available literature. Unlike DDT, chlordane, aldrin/dieldrin, and a variety of other chlorinated pesticides, endrin was never used extensively in urban areas. This is reflected in the results from EPA s Nationwide Urban Runoff Program, which showed no detections in 86 high-flow water samples from 51 urbanized watersheds from 19 cities (Cole et al. 1984). Analysis of EPA STORET monitoring information from ambient surface water showed a significant percentage of detections for endrin (32% of 8,789 samples), but most were near the detection limits, with a national median concentration of 0.001 ppb (Staples et al. 1985). A similar analysis of STORET data for endrin aldehyde showed that this compound was not found in 770 samples of ambient surface water. More recently, endrin was not detected (detection limit 49 ng/L [0.045 ppb]) in surface water from the Yakima River Basin, Washington (Foster et al. 1993). However, in... 

A drin and Dieldrin Metabolism.— The in vivo metabolism of the chlorinated alicyclic insecticides, aldrin and dieldrin, has been measured. Fish were exposed to l c-labelled aldrin or dieldrin for 6 hours. The metabolism of each compound was monitored by thin layer chromatography of hexane and chloroform-methanol extracts of liver homogenates, followed by liquid scintillation counting of the spots (5,15,16). 

Hepatic mixed-function oxidase activities demonstrated seasonal trends, with higher specific activities in the cold weather months in both populations with few differences in enzyme activities or cytochrome levels between the two populations. Metabolism of aldrin, dieldrin and DDT was similar between the two populations. R fish have larger relative liver size and, therefore, a greater potential for xenobiotic metabolism. However, biotransformation appears to be of minor importance in chlorinated alicyclic insecticide resistance in mosquitofish barriers to penetration appear to be of greater importance and an implied target site insensitivity appears to be the most important factor in resistance. 

Dieldrin—which belongs to the 12 POPs banned by the Stockholm convention and is in the same class of other pesticides named drins, such as aldrin and endrin—possesses six aliphatic chlorine atoms on a polycyclic skeleton. The multiphasic dechlorination, in the presence of A336, isooctane, aqueous KOH, Pd/C, and hydrogen, proceeded with a different selectivity and degree of dechlorination, depending on the choice of catalyst system, and base concentration. It always required the base and was favored by the presence of A336. It produced a mixture of products derived from the subsequent removal of chlorines, up to a small percentage of monochlorinated derivative. ... 

Aldrin org chem CijHgCI Trade name for a water-insoluble, white, crystalline compound, consisting mainly of chlorinated dimethanonaphthalene used as a pesticide. al-dron ... 

Surface Water. Under oceanic conditions, aldrin may undergo dihydroxylation at the chlorine free double bond to produce aldrin diol (quoted, Verschueren, 1983). In a river die-away test using raw water from the Little Miami River in Ohio, 26, 60, and 80% of aldrin present degraded after 2, 4, and 6 wk, respectively (Eichelberger and Lichtenberg, 1971). 

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. 

Organic compounds, aromatic solvents (benzene, toluene, nitrobenzenes, and xylene), chlorinated aromatics (PCBs, chlorobenzenes, chloronaphthalene, endrin, and toxaphene), phenols and chlorophenols (cresol, resorcinol, and nitrophe-nols), polynuclear aromatics (acenaphthene, benzopyrenes, naphthalene, and biphenyl), pesticides and herbicides (DDT, aldrin, chlordane, BHCs, heptachlor, carbofuran, atrazine, simazine, alachlor, and aldicarb), chlorinated... 

Several widely used pesticides are highly chlorinated polycyclic compounds derived from hexachloropentadiene. They include Aldrin, Dieldrin, and Chlordane. Use of these substances is to be curtailed greatly because of undesirable environmental effects. 

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