2-Thiazolidinethione-4-Carboxylic Acid from the Reaction of Captan with Cysteine

Lukens, Raymond J.; Sisler, H. D.

doi:10.1126/science.127.3299.650

Cited by 33 publications

(18 citation statements)

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“…In addition, it is used to prevent russetting of fruits (Gildemacher et al, 2006). It is considered to be a nonspecific thiol reactant that interferes with accessible sulfhydryl groups of cysteines by the formation of intermediate thiophosgene (Lukens & Sisler, 1958). Besides its antifungal effects, captan seems also to interfere with insect growth and development in a way that resembles the classical chitin synthesis inhibitors.…”

Section: Thiophthalimides: Captanmentioning

confidence: 99%

Chitin synthesis inhibitors: old molecules and new developments

2012

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Chitin is the most abundant natural aminopolysaccharide and serves as a structural component of extracellular matrices. It is found in fungal septa, spores, and cell walls, and in arthropod cuticles and peritrophic matrices, squid pens, mollusk shells, nematode egg shells, and some protozoan cyst walls. As prokaryotes, plants and vertebrates including humans do not produce chitin, its synthesis is considered as an attractive target site for fungicides, insecticides, and acaricides. Although no chitin synthesis inhibitor has been developed into a therapeutic drug to treat fungal infections in humans, a larger number of compounds have been successfully launched worldwide to combat arthropod pests in agriculture and forestry. This review summarizes the latest advances on the mode of action of chitin synthesis inhibitors with a special focus on those molecules that act on a postcatalytic step of chitin synthesis.

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Section: Thiophthalimides: Captanmentioning

confidence: 99%

Chitin synthesis inhibitors: old molecules and new developments

2012

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“…Compound 1 inhibited the activity of the alcohol dehydrogenase. These fungitoxic and enzyme inhibiting properties were similar to those of the SHinhibiting fungicides such as captan and chlorthalonil (4,5). The results strongly suggested that the primary mode of action of compound 1 is the inhibition of the SHenzyme (2).…”

Section: Structure-activity Analyses Of Fungicidal a 3 -L24-thiadiamentioning

confidence: 52%

Quantitative Structure—Activity and Molecular Modeling Studies of Novel Fungicides and Herbicides Having 1,2,4-Thiadiazoline Structures

Nakayama

Hagiwara

Hashimoto

et al. 1995

ACS Symposium Series

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Structure-activity analyses of bioactive 1,2,4-thiadiazolines were studied. With the procedure of the traditional quantitative structure--activity analyses, the fungicidal activity of a series of ∆ 3 -1,2,4-thiadiazoline derivatives against the cucumber downy mildew was examined using a parameter for the reactivity of molecules defined by quantum-chemical indices. The result suggested that a suitable range of the reactivity is required for this series of compounds to control the plant disease through the inhibition of SH-enzymes. A series of the Δ 2 -1,2,4-thiadiazolines exhibited a light-dependent herbicidal activity similar to that induced by cyclic imide herbicides. The structure -activity analyses of the light-dependent compounds were made by using theoretically estimated steric and electrostatic features of the molecule. Similarity indices among these compounds rationalized their structure-activity patterns stereoelectronically. The structural requirements for light-dependent herbicides were hypothesized on the basis of the molecular similarity indices.1,2,4-Thiadiazolines have been attractive candidates of new drugs and agrochemicals since their biological activities have scarcely been reported. There are three isomeric forms, i.e. y Δ 2 , Δ 3 and Δ 4 , in the 1,2,4-thiadiazolines according to the position of the double bond as shown in Figure 1. The syntheses of derivatives have also been interesting subjects in synthetic chemistry. We have synthesized a number of derivatives of these isomeric thiadiazolines and screened them for their biological activities to develop new pesticides. The derivatives have been shown to exhibit various pesticidal activities. For example, a series of Δ 2 -1,2,4-thiadiazolines having a fused ring system (I) show a herbicidal activity (7), and the 5-phenylimino-A 3 -1,2,4-thiadiazolines (II) exhibit a fungicidal activity to control a plant diseases (2). Furthermore, the A 4 -l,2,4-thiadiazoline derivatives (III) are insecticidal (3). This chapter describes the structure-activity studies of the Δ 3 -and Δ 2 -1,2,4-thiadiazolines based on the traditional Hansch-type quantitative structure-activity analyses (QSAR) and molecular modeling studies, respectively.

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“…Previous studies have shown that captan (Ntrichloromethylthio-4--cyclohexene-1,2-dicarboximide), a widely used fungicide, is decomposed by reaction with thiols of fungi (Lukens and Sisler, 1958;Richmond and Somers, 1966) and also with sulfite and thiosulfate ions (DeBaun et al, 1974)According to the studies reported by Moriya et al (1978), this fungicide is rapidly detoxified after incubation with S-9 factor of rat liver homogenate, cysteine or rat blood. Acute toxicity of captan is relatively low in rats due to its degradation in the gastrointestinal tract (oral LD5O, 15 g/kg); however, it is a highly toxic compound if administered intraperitoneally (i.p.…”

Section: Introdtjctiokmentioning

confidence: 69%

Involvement of glutathione in the reduction of captan-induced in vivo inhibition of monooxygenases and liver toxicity in the rat

Rr¹

1988

J. of Env. Sc. & Hlth., Part B

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If given orally captan is relatively nontoxic, but it can be extremely toxic after parenteral exposure. Therefore, a single i.p. dose of captan (20 mg/kg) was given to male Sprague-Dawley rats and its effect on liver microsomal mixed function oxidases and certain serum enzymes (SDH, SGPT and SGOT) was studied. The single dose of captan caused marked depression of microsomal cytochrome P-450 and the activity of benzphetamine N-demethylase and aniline hydroxylase, and moderate elevation of the serum enzymes indicative of liver damage. However, reduced glutathione (100 mg/kg, i.p.) given prior to captan, appears to decrease the liver toxicity as measured by reduced inhibition of the microsomal enzymes and elevation of serum enzymes activity. The results suggest that glutathione and other compounds containing sulfhydryl groups may protect the subjects from captan-induced liver toxicity.

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2-Thiazolidinethione-4-Carboxylic Acid from the Reaction of Captan with Cysteine

Cited by 33 publications

References 1 publication

Chitin synthesis inhibitors: old molecules and new developments

Chitin synthesis inhibitors: old molecules and new developments

Quantitative Structure—Activity and Molecular Modeling Studies of Novel Fungicides and Herbicides Having 1,2,4-Thiadiazoline Structures

Involvement of glutathione in the reduction of captan-induced in vivo inhibition of monooxygenases and liver toxicity in the rat

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