Metabolism of Chlorinated Hydrocarbon Insecticides

Woodard, Geoffrey E.; Davidow, Bernard; Lehman, A. J.

doi:10.1021/ie50460a032

Cited by 22 publications

(10 citation statements)

References 3 publications

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“…If this resistance has its basis in a detoxication mechanism we must assume that the methoxychlor strain attacks the molecule at some point other than the trichlorethane end which is common to DDT and methoxychlor. It is possible that metabolism of the methoxy groups of methoxychlor is involved, and in this connexion it may be significant that the fates of methoxychlor and DDT in the rabbit are different (Prickett & Laug, 1953;Woodward, Davidow & Lehman, 1948). The suggestion in this work is that demethylation and conjugation of the hydroxyl is involved but no details have been published.…”

Section: XLIVmentioning

confidence: 90%

Detoxication Mechanisms in Insects

Smith

1955

Biological Reviews

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SUMMARY Information relating to the metabolic alteration, in insects, of foreign organic compounds has been reviewed and is summarized in Table i. The convenient term ‘detoxication mechanisms’ has been retained to describe the reactions involved, although these do not necessarily reduce the toxicity of absorbed substances, and may in some cases produce extremely toxic metabolites. Some of these reactions, however, particularly those which involve conjugations, almost always yield nontoxic products. Although much of the evidence is still unsatisfactory from a chemical standpoint it has become clear that a number of detoxication mechanisms are common to both insects and vertebrates. Nevertheless, the extent to which they occur in different species may vary. One important conjugation mechanism is different in insects and vertebrates, as it has been found that phenols are converted to their ‐glucosides in insects. To this extent insects are more like plants than like vertebrates, in which phenols are detoxified by condensation with glucuronic acid. Other conjugations, in which phenols are transformed into ester sulphates, aromatic amino groups are acetylated, aromatic acids condensed with glycine and heterocyclic ring nitrogens methylated, are found in both vertebrates and insects. Very few definite data are available on oxidations of foreign organic compounds in insects, and it is not possible to say whether the mechanisms involved are always the same in insects and vertebrates. What is known of the intermediary metabolism of tryptophan and tyrosine does suggest, however, that there may be a common path for some aromatic hydroxylations. The products of metabolic oxidation of the thiophosphate and phosphoramide insecticides in vertebrates and insects have been shown to be the same, and these products are much more toxic than the original material. The data available on the metabolism of DDT (XXXVII) and some related compounds have been summarized. In most insects it is believed that DDT is dehydrochlorinated to an ethylenic compound, DDE (XXXVIII). No evidence has been found that insects form any DDA (XXXIX), the metabolite found in vertebrates, but evidence is accumulating that one or more, as yet unidentified, metabolites of DDT are produced. One of these is very probably some form of conjugate. In addition to the mechanisms of conjugation, oxidation and dehydrochlorination, several minor processes have been observed in a single species. Aromatic nitro groups are reduced to amino groups, thiocyanate is formed from cyanide and heavy metals may be inactivated by conversion to their insoluble sulphides. I am grateful to Professor R. T. Williams for discussions and criticisms of the manuscript.

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Section: XLIVmentioning

confidence: 90%

Detoxication Mechanisms in Insects

Smith

1955

Biological Reviews

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“…At a constant daily dosage, the storage of DDT in fat increases steadily for a while, but eventually reaches a maximum or plateau in the rat (39)(40)(41)(42), in the monkey (43), in cattle (44), and in man (22,45). A steady state is also HAYES reached in the concentration of DDT in the milk of cows (46,47) and in the eggs of chickens (48).…”

Section: Storagementioning

confidence: 99%

“…The time necessary for the rat to reach a steady state in the storage of DDT has been estimated at as little as 7 weeks (39,40) and as much as 19 to 23 weeks (41,42). The most likely value is considered to be 17 weeks (43).…”

Section: Storagementioning

confidence: 99%

Review of the Metabolism of Chlorinated Hydrocarbon Insecticides Especially in Mammals

Wj¹

1965

Annu. Rev. Pharmacol.

119

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This review discusses the absorption, storage, biotransformation, and excretion of chlorinated hydrocarbon insecticides; thus, it emphasizes those aspects of physiology that can be studied by the methods of analytical or ganic chemistry. The broader aspects of toxicity, as they relate to the me tabolism of these materials, were discussed by Winteringham & Barnes (1).This review emphasizes mammalian metabolism of the compounds, but con tains some information on their metaboli sm by other organisms, a subject that has already been reviewed by Perry (2). In relation to mammals, great est interest centers in numerous repeated doses that produce no obvious in jury and that are so small that they might be encountered under practical conditions in the use of insecticides. For this reason, DDT and related re sidual insecticides are emphasized, but some information is given on the chlorinated hydrocarbon fumigants.

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“…) Chlordane is absorbed by the animal but its fate and whether or not the chemical is excreted in the urine is unknown. -Woodward et al ( 509 ) No harm resulted to rats, mice, or guinea pigs when they were subjected for 45 minutes on each of 38 days to air bearing aerosols containing chlordane with methylene dichloride or dimethyl phthalate as solvents, the average initial concentration of chlordane being approximately 1.9 mg. per liter. When aerosols with either kerosene, methylene dichloride, or dimethyl phthalate as a solvent were introduced into the chamber at intervals of 10 minutes over an hour in an initial concentration of 10 mg. of chlordane per liter, and this procedure was repeated three times on each of four successive days, many of the animals exhibited typical signs of poisoning by chlordane.…”

Section: Chlordanementioning

confidence: 99%

A digest of information on chlordane

Roark¹

1951

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Metabolism of Chlorinated Hydrocarbon Insecticides

Cited by 22 publications

References 3 publications

Detoxication Mechanisms in Insects

Detoxication Mechanisms in Insects

Review of the Metabolism of Chlorinated Hydrocarbon Insecticides Especially in Mammals

A digest of information on chlordane

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