A Plant Surface Oxidation Product of Endosulfan

Cassil, C. C.; Drummond, P. E.

doi:10.1093/jee/58.2.356

Cited by 19 publications

(6 citation statements)

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“…4 In the environment, the cyclic sulfite group of ES can be oxidized to the corresponding sulfate (ES sulfate) or hydrolyzed to form a less toxic diol (ES diol). Studies on the fate of ES in soils, [12][13][14][15][16][17] sediments, [18][19][20] and on crops 2,[21][22][23][24][25] indicate that oxidation readily occurs and suggest that formation of ES sulfate is due to biological processes. Many of these studies indicate that b-ES is the more persistent ES isomer; recent studies support these findings and report that a-ES is preferentially oxidized over b-ES by soil microorganisms, 26 plankton, 27 insects, 28 in sediments, 19 and on crops.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective degradation of aqueous endosulfan in modular estuarine mesocosms: formation of endosulfan γ-hydroxycarboxylate

2003

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Solutions of alpha-endosulfan, beta-endosulfan, and technical grade endosulfan (70alpha:30beta) were added to modular estuarine mesocosms; the kinetics and degradation products from each mesocosm are reported. The persistent product endosulfan sulfate was generated in all cases; however, its yield was approximately a factor of three higher from alpha-endosulfan relative to beta-endosulfan. Beta-endosulfan hydrolyzed faster than alpha-endosulfan to endosulfan diol, which then rapidly degraded to endosulfan ether, endosulfan alpha-hydroxyether (major product), and endosulfan lactone. The ring-opened form of the lactone, endosulfan gamma-hydroxycarboxylate, is reported for the first time; it appears to be a terminal product, at least over the timescale of the experiment. The equilibrium between endosulfan gamma-hydroxycarboxylate and endosulfan lactone is dependent on pH, as only the protonated form of the gamma-hydroxy acid undergoes ring-closure. The pKa of the gamma-hydroxy acid was determined to be 5.7, implying that the lactone will quickly open and deprontonate under environmentally relevant conditions.

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Section: Introductionmentioning

confidence: 99%

Stereoselective degradation of aqueous endosulfan in modular estuarine mesocosms: formation of endosulfan γ-hydroxycarboxylate

2003

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“…However, its chemical peculiarities and its physiological behavior in higher organisms make it uncomparable to the other cyclodiene insecticides (6). In residue and metabolism investigations carried out in the past (1,2,4,5,8), metabolites that originated through a stepwise oxidative degradation of the heterocyclic ring were found; according to Schuphan et al (8), these could also be formed by various strongly oxidizing chemical agents. These metabolites were the same as those described in the present work.…”

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Degradation of [8,9,-14C]endosulfan by soil microorganisms

Martens¹

1976

Appl Environ Microbiol

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Twenty-eight soil fungi, 49 soil bacteria, and 10 actinomycetes were tested as to their ability to degrade the insecticide endosulfan. Using 14C-labeled material, the qualitative as well as the quantitative formation of metabolities, as well as of 14CO2, could be followed. Sixteen fungi, 15 bacteria, and 3 actinomycetes were found capable of metabolizing more than 30% of the applied endosulfan. The major metabolities detected were endosulfate, formed by oxidation of the sulfite group, and endodiol, formed by hydrolysis of the ester bond. The majority of highly active fungi formed endosulfate as the major metabolite, whereas the majority of active bacteria formed endodiol. In addition to endosulfate and endodiol, individual cultures contained small quantities of endohydroxyether and two unidentified products. The very small quantities of 14CO2 evolved from cultures indicated that an extensive mineralization of the carbon skeleton of endosulfan did not occur.

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“…Volatile metabolites found under controlled conditions were the sulfate and the ether. Endosulfan sulfate was obtained as a residue component on leafy vegetables sprayed with endosulfan (Cassil and Drummond, 1965). They hypothesized that the mechanism for the oxidation of endosulfan was by active oxygen derived from growing plant tissue.…”

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Photodecomposition of endosulfan and related products in thin films by ultraviolet light irradiation

Archer¹,

Nazer²,

Crosby³

1972

J. Agric. Food Chem.

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hexahydro -6,9 -methano-2,4,3-benzodioxathiepin 3-oxide) isomers I and II in a thin film produced endosulfandiol as a major product. Endosulfan -hydroxy ether, lactone, ether, and an unknown No. 1 were additional photodecomposition products but in lesser amounts than the diol. Irradiation of endosulfandiol produced -hydroxy ether, unknowns No. 2 and 3. Irradiation of endosulfan ether gave the -hydroxy ether and the lactone. Irradiation of endosulfan a-hydroxy ether gave the ether and unknowns No. 2 and 3. Irradiation of endosulfan lactone resulted in less than 1 % each of the diol and the ether, but no -hydroxy ether was produced. The endosulfan sulfate was not a product from any of the irradiated compounds, and no degradation products were detected when it was irradiated with ultraviolet light. Derivatization of the diol and the -hydroxy ether by silylation and acetylation was necessary for the quantitation and identification of these two compounds within the photolysis mixtures. Photolysis of pesticides is important in the fate of these compounds in the environment and affects their toxicological characteristics. For example, Roburn (1963) found that grasses sprayed with dieldrin and exposed to sunlight under natural conditions for several months contained an unknown persistent compound. Dieldrin deposited as a film on glass plates and irradiated under a germicidal ultraviolet lamp (2537 A) was converted to some similar persistent compounds found on the grasses. The fact that strong

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A Plant Surface Oxidation Product of Endosulfan

Cited by 19 publications

References 0 publications

Stereoselective degradation of aqueous endosulfan in modular estuarine mesocosms: formation of endosulfan γ-hydroxycarboxylate

Stereoselective degradation of aqueous endosulfan in modular estuarine mesocosms: formation of endosulfan γ-hydroxycarboxylate

Degradation of [8,9,-14C]endosulfan by soil microorganisms

Photodecomposition of endosulfan and related products in thin films by ultraviolet light irradiation

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