Insecticides endosulfan

Uses. Butanediol is used to manufacture the insecticide Endosulfan, other agricultural chemicals, and pyridoxine (vitamin B ) (see Vitamins) (116). Small amounts are consumed as a diol by the polymer industry. 

Coutselinis A, Kentarchou P, Boukis D. 1976. Separation and identification of the insecticide "endosulfan" from biological materials. Forensic Sci 8 251-254. 

Flodstrom S, Warngard L, Hemming H, et al. 1988. Tumor promotion related effects by the cyclodiene insecticide endosulfan studied in vitro and in vivo. Pharmacol Toxicol 62 230-235. 

Fransson-Steen R, Rodstrom S, Warngard L. 1992. The insecticide endosulfan and its two stereoisomers promote the growth of altered hepatic foci in rats. Carcinogenesis 13(12) 2299-2303. 

Goebel H, Gorbach S, Knauf W, et al. 1982. Properties, effects, residues, and analytics of the insecticide endosulfan. Residue Rev 83 1-165. 

Guerin TF, Feeder JF. 1998. Potential environmental endocrine disruption implications from the widespread use of the commonly used insecticide endosulfan. Am Chem Soc Abstr Pap 1-3 102. 

Hack R, Ebert E, Leist KH. 1995. Chronic toxicity and carcinogenicity studies with the insecticide endosulfan in rats and mice. Eood Chem Toxicol 33(11) 941-50. 

Velazquez A, Creus A, Xamena N, et al. 1984. Mutagenicity of the insecticide endosulfan in Drospholia melanogaster. Mutat Res 136 115-118. 

An example of a sulfite ester made from thionyl chloride is the commercial insecticide endosulfan [115-29-7]. A stepwise reaction of thionyl chloride with two different alcohols yields the commercial miticide, propaigite [2512-55-8] (189). Thionyl chloride also has applications as a co-reactant in sulfonations and chlorosulfonations. A patent describes the use of thionyl chloride in the preparation of a key intermediate, bis(4-chlorophenyl) sulfone [80-07-9], which is used to make a commercial polysulfone engineering thermoplastic (see Polymers containing sulfur, polysulfone) (190). The sulfone group is derived from chlorosulfonic acid the thionyl chloride may be considered a co-reactant which removes water (see Sulfolanes and sulfones). 

Two different types of immunoassays, a competitive-type and an inhibition-type, were developed and compared for the insecticide, endosulfan. The detection range of both assay types was similar, 3-500 ng/ml for the competitive-type and 5-500 ng/ml for the inhibition-type assay. Metabolites of endosulfan and other insecticidal chloro-hydrocarbons possessing a hexachlorocyclopentene structure exhibited considerable crossreaction in both assays, so these immunoassays could be used for detection of class-specific compounds. The inhibition-type immunoassay showed less susceptibility to interfering factors and, therefore, seemed to be more suitable for environmental analysis. 

Conventional analyses for the insecticide, endosulfan, in environmental samples requires time-consuming multistep cleanup procedures prior to the final quantification by gas chromatography (l). For this reason, a sensitive and rapid ELISA could be of great value if large numbers of samples have to be analyzed. The advantages of immunoassays for residue analysis have been described by Hammock and Mumma (2). 

Table IV lists the insecticidal activity of cyclic sulfites In this case, the exo cyclic sulfites of 5,6-bis(hydroxymethyl)-7-isopropylidenebicyclo[2.2 l]hept-2-ene [20] was active whereas the corresponding endo Isomer [18] was inactive Monoepoxldation [21 and 22] and diepoxidation [23] of the exo cyclic sulfite resulted in a slight increase in activity Compound 15 was the most active among this series of compounds The LD q value of this compound was estimated to be about 1 pg/fly when topically applied to houseflies without any synergists (data not shown) The C-7 isopropylidene group proved to be unnecessary for high activity by comparison with compound 18. The activity decreased after epoxidation [16] or hydrogenation [17] of the endocyclic double bond The cyclodiene insecticide endosulfan was about 10 times as active as [15] ...

Separation and Identification of the Insecticide "Endosulfan" from Biological Materials... 

Lindane is one of eight different hexachlorocyclohexane (HCH), C H Cl, isomers and its Chemical Abstract n.2cniQ is la, 2a 3P, 4a, 5a 6P-hexachlorocyclohexane [58-89-9] (y-HCH or y-BHC, ben2ene hexachloride) (80). Commercial products containing lindane are marketed as either a mixture of isomers or as the pure y-BHC isomer. Not unexpectedly, lindane is a highly stable lipophilic compound and it has been used extensively worldwide as an insecticide. In contrast, hexachloropentadiene, C Cl, is an extremely reactive industrial intermediate used as a chemical intermediate in the synthesis of a broad range of cyclodiene-derived pesticides, which include endosulfan, endrin, heptachlor, and several different organohalogen flame retardants (81). 

The reagent sequence is specific for endosulfan and phosphamidon. Other insecticides, e.g. organochlorine insecticides, such as endrin, aldrin, dieldrin, DDT and BHC, organophosphorus insecticides, such as malathion, parathion, dimethoate, quinalphos, phorate and fenitrothion, or carbamate insecticides, such as baygon, car-baryl and carbofuran do not react. Neither is there interference from amino acids, peptides or proteins which might be extracted from the biological material together with the pesticides. 

Dr. John E. Casida from the University of California Berkeley is inveshgating the fundamental basis for the selective toxicity of insecticides, including endosulfan, acting at the gamma-aminobutyric acid (GABA) receptor of mammals and insects. The research is sponsored by the National Institute of Environmental Health Sciences. 

Endosulfan is released to the environment mainly as the result of its use as an insecticide. Significant contamination is limited to areas where endosulfan is manufactured, formulated, applied, or disposed of. The compound partitions to the atmosphere and to soils and sediments. Endosulfan can be transported over long distances in the atmosphere, but the compound is relatively immobile in soils. It is transformed by hydrolysis to the diol and by microorganisms to a number of different metabolites. It is bioconcentrated only to low levels and does not biomagnify in terrestrial or aquatic food chains. 

Endosulfan has been released to the environment mainly as a result of its use as an insecticide. There are no known natural sources of the compound. Endosulfan and endosulfan sulfate are not contained in the list of chemicals for which releases are required to be reported to EPA for the SARA Section 313 Toxic Release Inventory (TRI) (EPA 1997a). 

As a result of its use as an insecticide on fruit trees, vegetables, and other crops, endosulfan is released directly to the atmosphere during application. The compound is applied principally by air-blast equipment or boom sprayers (WHO 1984). No information was found in the available literature regarding atmospheric releases from manufacturing or formulation operations, or occurrence of the compound in air samples collected at NPL sites. 

Production, Import/Export, Use, Release, and Disposal. Endosulfan is distributed in the environment as a result of its use as an insecticide (Gregor and Gummer 1989 NRCC 1975 Strachan et al. 1980). Humans may be exposed through the ingestion or use of contaminated food (Gartrell et al. 1986 Podrebarac 1984a) or tobacco products (EPA 1982a), contact with media from contaminated hazardous waste sites (principally soils), or insecticide apphcafion (Oudbier et al. 1974 Wolfe et al. 1972). 

Although endosulfan is currently produced for use as an insecticide, information on the current production, import, and export of endosulfan by the United States is limited. Annual production volumes in the United States were 3 million pounds in 1980 (Sitfig 1980), and 10,000 metric tons (approximately 22 million pounds) worldwide were reported in 1984 (WHO 1984). However, as of 1982, endosulfan was no longer produced in the United States (HSDB 1999). Although U.S. imports of endosulfan are reportedly substantial, the most recent import information (182,000 kg) was for the year 1982 (HSDB 1999). Additional information on the producfion/formulation, import, and export volumes for endosulfan would be useful in assessing the extent to which, and conditions under which, humans may be exposed to endosulfan or endosulfan sulfate. 

Bioavailability from Environmental Media. Endosulfan can be absorbed following inhalation of contaminated workplace air and ingestion of insecticide-contaminated food (Ely et al. 1967). Dermal contact with or ingestion of endosulfan that is tightly bound to soil particles is an exposure route of... 

ChanJ. 1995. Acute tubular necrosis following endosulfan insecticide poisoning Author s reply. Clin Toxicol 33(4) 377-378. 

Das N, Srivastava N, Srivastava LM. 1988. Activation of serum complement by organochlorine insecticides, DDT and endosulfan. Curr Sci 57 524-526. 

DurejaP, Mukerjee SK. 1982. Photoinduced reactions Part IV. Studies on the photochemical fate of 6,7,8,9,10,10-hexachloro-l,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzo(e)dioxathiepin-3-oxide (endosulfan), an important insecticide. Indian J Chem 21B 411-413. 

Naqvi SM, Vaishnavi C. 1993. Mini Review. Bioaccumulative potential and toxicity of endosulfan insecticide to non-target animals. Comp Biochem Physiol C 105(3) 347-61. 

Raizada RB, Srivastava MK, Dikshith TSS. 1991. Lack of estrogenic effects of endosulfan An organochlorine insecticide in rat. Nat Acad Sci Lett 14(2) 103-107. 

The cyclodiene insecticides aldrin, dieldrin, endrin, heptachlor, endosulfan, and others were introduced in the early 1950s. They were used to control a variety of pests, parasites, and, in developing countries, certain vectors of disease such as the tsetse fly. However, some of them (e.g., dieldrin) combined high toxicity to vertebrates with marked persistence and were soon found to have serious side effects in the field, notably in Western European countries where they were extensively used. During the 1960s, severe restrictions were placed on cyclodienes so that few uses remained by the 1980s. 

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