Biological and Chemical Behavior of Perhalogenmethylmercapto Fungicides: Metabolism and in Vitro Reactions of Dichlofluanid in Comparison with Captan

Schuphan, Ingolf; Westphal, D.; Haque, A.; Ebing, W.

doi:10.1021/bk-1981-0158.ch006

Cited by 11 publications

(7 citation statements)

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“…Captan and folpet have a Common Mechanism of Toxicity (CMT) resulting in a common Mode of Action (MOA) (Bernard and Gordon, 2000); however, captan and captafol are distinct molecules with different chemistry and different modes of action (Schuphan et al, 1981). In particular, captafol has a two-carbon side chain that is qualitatively different from the one carbon trichloromethylthio side chain of captan.…”

Section: Captan Is a Rat Carcinogenmentioning

confidence: 99%

Captan: Transition from ‘B2’ to ‘not likely’. How pesticide registrants affected the EPA Cancer Classification Update

Gordon¹

2007

J of Applied Toxicology

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On 24 November 2004 EPA changed the cancer classification of captan from a 'probable human carcinogen' (Category B2) to 'not likely' when used according to label directions. The new cancer classification considers captan to be a potential carcinogen at prolonged high doses that cause cytotoxicity and regenerative cell hyperplasia. These high doses of captan are many orders of magnitude above those likely to be consumed in the diet, or encountered by individuals in occupational or residential settings. This revised cancer classification reflects EPA's implementation of their new cancer guidelines. The procedures involved in the reclassification effort were agreed upon with EPA and involved an Independent Transparent Review as it related to four components that formed the basis of the original 1986 B2 classification: mouse tumors; rat tumors; mutagenicity; and structural similarity to other carcinogens. A Peer Review Panel organized and administered by Toxicology Excellence for Risk Assessment (TERA) met on 2-3 September 2003. The Panel concluded that captan acted through a non-mutagenic threshold mode of action that required prolonged irritation of the duodenal villi as the initial key event. EPA's Cancer Assessment Review Committee (CARC) met on 9 June 2004 and endorsed the Peer Review findings. EPA intended to have the FIFRA Scientific Advisory Panel (SAP) consider the basis for this reclassification but found the science was robust and judged that a SAP review was not warranted. Using the revised classification, the margin of exposure is approximately 1,200,000, supporting the 'not likely' characterization.

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Section: Captan Is a Rat Carcinogenmentioning

confidence: 99%

Captan: Transition from ‘B2’ to ‘not likely’. How pesticide registrants affected the EPA Cancer Classification Update

Gordon¹

2007

J of Applied Toxicology

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“…3. Conjugation at non-carbon sites: In plants, reactions with non-carbon sites have scarcely been described, for example, as been reported for diclofluanid (Schupahn et al, 1981), but they may still be significant.…”

Section: Facts On Glutathione Transfermentioning

confidence: 99%

Conjugating Enzymes Involved in Xenobiotic Metabolism of Organic Xenobiotics in Plants

Schröder

Collins

2002

International Journal of Phytoremediation

123

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“…A fungicide dichlofluanid is metabolized to a toxic metabolite thiophosgene derivative in a process that appears to involve two GSH conjugation steps (Schuphan et al, 1981).…”

Section: Detoxification and Toxification Reactions Of Gsts With Xenobmentioning

confidence: 99%

A Tale of Plant Glutathione S-Transferases: Since 1970

Öztetik

2008

Bot. Rev

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Ubiquitously distributed multifunctional superfamily of Glutathione Stransferases (GST) generally constitute a dimeric enzymes and catalyse the conjugation of the thiol group of the glutathione (GSH) to diverse electrophilic centres on lipophilic molecules with the formation of rather less active end products. Besides their well investigated conjugation reaction for the detoxification of endogenous and xenobiotic compounds, they can also be involved in both GSH dependent peroxidation or isomerization reactions, and several other non-catalytic functions, like binding of non-substrate ligands, stress-induced signalling processes and preventing of apoptosis. Plant GSTs have been a focus of attention because of their roles in herbicide detoxification and today seven distinct classes of soluble (cytosolic) GSTs are presented as Phi, Tau, Theta, Zeta, Lambda, Dehydroascorbate reductases (DHARs) and Tetrachlorohydroquinone dehalogenase (TCHQD). While GSTs show overall sequence diversification within and between classes, they retain a high level of three-dimensional structure conservation over long evolutionary periods. In this review mainly the soluble plant GSTs will be considered by giving attention to their structures, subcellular localizations, genomic organizations, catalytic/noncatalytic functions, and comparisons given with respect to their mammalian counterparts where necessary.

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Biological and Chemical Behavior of Perhalogenmethylmercapto Fungicides: Metabolism and in Vitro Reactions of Dichlofluanid in Comparison with Captan

Cited by 11 publications

References 0 publications

Captan: Transition from ‘B2’ to ‘not likely’. How pesticide registrants affected the EPA Cancer Classification Update

Captan: Transition from ‘B2’ to ‘not likely’. How pesticide registrants affected the EPA Cancer Classification Update

Conjugating Enzymes Involved in Xenobiotic Metabolism of Organic Xenobiotics in Plants

A Tale of Plant Glutathione S-Transferases: Since 1970

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