Enhancement of Photoalteration of Cyclodiene Insecticide Chemical Residues by Rotenone

Ivie, Glen W.; Casida, John E.

doi:10.1126/science.167.3925.1620

Cited by 30 publications

(14 citation statements)

References 7 publications

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“…49 -50 Their conclusion was that the C and D rings in these molecules (see above) are most critical for activity and that the structural requirements for this photosensitizer activity are met by compounds containing the moiety shown in heavy lines, with aliphatic or aromatic substituents at the positions 6a or 12a, or both. 49 Hydroxylation at position 11 results in loss of potency. Compounds with a double bond between the positions 6a and 12a have greatly diminished activity.…”

Section: Rotenonementioning

confidence: 99%

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Mechanisms in sensitized photochemistry of environmental chemicals

Choudhry

Roof

Hutzinger

1979

Toxicological & Environmental Chemistry Reviews

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This review consists of three main parts. After a short discussion of the theory of photochemistry, the three major mechanisms (radiative, short range and long range) for the transfer of electronic excitation energy from sensitizers (donors) to substrates (acceptors) are described. Criteria for the selection of. sensitizers are a high efficiency of intersystem crossing (in the case of triplet sensitization) and energy transfer, and strong absorption at wavelengths longer than those at which the acceptor absorbs. Two mechanisms of sensitized photooxygenation, viz. the radical and singlet oxygen type, are discussed.The second part of this review deals with photosensitizers, with a strong emphasis on compounds of importance in environmental photochemistry on the one hand and those interesting from a mechanistic point of view on the other.The third part describes photo-inducers and their role in photoreactions. Additional literature references (to January 1978) are presented at the end of this review.

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Section: Rotenonementioning

confidence: 99%

“…49 The photosensitizing activity of rotenone in. catalyzing the photoconversion of dieldrin (77) is greater on glass surface than on bean leaves.…”

Section: Rotenone Bean Leaves •16+18mentioning

confidence: 99%

Mechanisms in sensitized photochemistry of environmental chemicals

Choudhry

Roof

Hutzinger

1979

Toxicological & Environmental Chemistry Reviews

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“…Degradation of pesticide residues on leaf surfaces may be enhanced by adding photosensitizers such as triphenylamine to DDT (Figure 2A) or rotenone to dieldrin (Figure 2B), but this results in the formation of bioactive and persistent photoproducts (Ivie and Casida 1970, 1971; Lawrence and Casida 1984). Furthermore, photosensitizers such as rotenone decompose (Cheng et al 1972) and may have to be reapplied.…”

Section: Ecochemistrymentioning

confidence: 99%

The Greening of Pesticide–Environment Interactions: Some Personal Observations

Casida

2012

Environ Health Perspect

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Background: Pesticide–environment interactions are bidirectional. The environment alters pesticides by metabolism and photodegradation, and pesticides in turn change the environment through nontarget or secondary effects.Objectives: Approximately 900 currently used commercial pesticides of widely diverse structures act by nearly a hundred mechanisms to control insects, weeds, and fungi, usually with minimal disruption of nature’s equilibrium. Here I consider some aspects of the discovery, development, and use of ecofriendly or green pesticides (i.e., pesticides that are safe, effective, and biodegradable with minimal adverse secondary effects on the environment). Emphasis is given to research in my laboratory.Discussion: The need for understanding and improving pesticide–environment interactions began with production of the first major insecticide approximately 150 years ago: The arsenical poison Paris Green was green in color but definitely not ecofriendly. Development and use of other pesticides has led to a variety of problems. Topics considered here include the need for high purity [e.g., hexachlorocyclohexane and polychloroborane isomers and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T)], environmental degradation and the bioactivity of resulting photoproducts and metabolites, pesticide photochemistry (including the use of structural optimization, photostabilizers, and photosensitizers to achieve suitable persistence), the presence of multiple active ingredients in botanical insecticides, the need to consider compounds with common mechanisms of action, issues related to primary and secondary targets, and chemically induced or genetically modified changes in plant biochemistry. Many insecticides are bird, fish, and honeybee toxicants, whereas herbicides and fungicides pose fewer environmental problems.Conclusion: Six factors have contributed to the greening of pesticide–environment interactions: advances in pesticide chemistry and toxicology, banning of many chlorinated hydrocarbons, the development of new biochemical targets, increased reliance on genetically modified crops that reduce the amount and variety of pesticides applied, emphasis on biodegradability and environmental protection, and integrated pest- and pesticide-management systems.

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“…photodecomposition products are less active than rotenone or are inactive as photosensitizers (1); thus the effective sensitizing period resulting from rotenone applications is expected to be a short one.…”

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confidence: 99%

“…Since each of these 8-substituted xanthines has also been obtained in vitro by reactions of 3-acetoxyxanthine with chloride ion or methionine, their production in vivo can be explained as resulting through the metabolic formation of an activated ester with a reactivity similar to that of the chemical model. 1 include measurements of the previously identified urinary metabolites of 3-hydroxyxanthine: allantoin, 3-hydroxyuric acid, uric acid, and xanthine, which result from the reducing or oxidizing actions of xanthine oxidase (3,4), and which, with unaltered 3-hydroxyxanthine, account for more than 90 percent of the radioactivity in the urine. An analogous series of metabolites formed by xanthine oxidase has been shown to result from guanine 3-N-oxide (5).…”

mentioning

confidence: 99%

Oncogenic Purine Derivatives: Evidence for a Possible Proximate Oncogen

Stöhrer

Brown

1970

Science

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Two additional urinary metabolites of the chemical oncogen 3-hydroxyxanthine are now identified as 8-chloroxanthine and 8-methylmercaptoxanthine. Such products are thought to be derived from a reactive intermediate which can be tentatively considered to be a proximate oncogen. Since each of these 8-substituted xanthines has also been obtained in vitro by reactions of 3-acetoxyxanthine with chloride ion or methionine, their production in vivo can be explained as resulting through the metabolic formation of an activated ester with a reactivity similar to that of the chemical model.

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Enhancement of Photoalteration of Cyclodiene Insecticide Chemical Residues by Rotenone

Cited by 30 publications

References 7 publications

Mechanisms in sensitized photochemistry of environmental chemicals

Mechanisms in sensitized photochemistry of environmental chemicals

The Greening of Pesticide–Environment Interactions: Some Personal Observations

Oncogenic Purine Derivatives: Evidence for a Possible Proximate Oncogen

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