InChI=1S/C9H4Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-4H |
HKIOYBQGHSTUDB-UHFFFAOYSA-N |
ClC(Cl)(Cl)SN1C(=O)c2ccccc2C1=O |
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antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
fungicide
A substance used to destroy fungal pests.
(via dicarboximide fungicide )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via dicarboximide antifungal agent )
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antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
fungicide
A substance used to destroy fungal pests.
(via dicarboximide fungicide )
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View more via ChEBI Ontology
2-[(trichloromethyl)sulfanyl]-1H-isoindole-1,3(2H)-dione
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folpel
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ChemIDplus
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N-(Trichlor-methylthio)-phthalamid
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ChemIDplus
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N-(trichloromethanesulfenyl)phthalimide
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ChEBI
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N-(trichloromethanesulphenyl)phthalimide
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ChemIDplus
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N-(trichloromethylthio)phthalimide
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ChemIDplus
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trichloromethylthiophthalimide
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ChemIDplus
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Acryptan
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ChemIDplus
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Cosan I
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ChemIDplus
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Faltan
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ChemIDplus
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Faltex
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ChemIDplus
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Orthophaltan
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ChemIDplus
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Phthaltan
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ChemIDplus
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354
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PPDB
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C18860
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KEGG COMPOUND
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folpet
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Alan Wood's Pesticides
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HMDB0031792
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HMDB
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US2553770
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Patent
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View more database links |
133-07-3
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CAS Registry Number
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NIST Chemistry WebBook
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133-07-3
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CAS Registry Number
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ChemIDplus
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193373
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Reaxys Registry Number
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Reaxys
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Heredia-Ortiz R, Berthet A, Bouchard M (2013) Toxicokinetic modeling of folpet fungicide and its ring-biomarkers of exposure in humans. Journal of applied toxicology : JAT 33, 607-617 [PubMed:22180346] [show Abstract] A human in vivo toxicokinetic model was built to allow a better understanding of the toxicokinetics of folpet fungicide and its key ring biomarkers of exposure: phthalimide (PI), phthalamic acid (PAA) and phthalic acid (PA). Both PI and the sum of ring metabolites, expressed as PA equivalents (PAeq), may be used as biomarkers of exposure. The conceptual representation of the model was based on the analysis of the time course of these biomarkers in volunteers orally and dermally exposed to folpet. In the model, compartments were also used to represent the body burden of folpet and experimentally relevant PI, PAA and PA ring metabolites in blood and in key tissues as well as in excreta, hence urinary and feces. The time evolution of these biomarkers in each compartment of the model was then mathematically described by a system of coupled differential equations. The mathematical parameters of the model were then determined from best fits to the time courses of PI and PAeq in blood and urine of five volunteers administered orally 1 mg kg(-1) and dermally 10 mg kg(-1) of folpet. In the case of oral administration, the mean elimination half-life of PI from blood (through feces, urine or metabolism) was found to be 39.9 h as compared with 28.0 h for PAeq. In the case of a dermal application, mean elimination half-life of PI and PAeq was estimated to be 34.3 and 29.3 h, respectively. The average final fractions of administered dose recovered in urine as PI over the 0-96 h period were 0.030 and 0.002%, for oral and dermal exposure, respectively. Corresponding values for PAeq were 24.5 and 1.83%, respectively. Finally, the average clearance rate of PI from blood calculated from the oral and dermal data was 0.09 ± 0.03 and 0.13 ± 0.05 ml h(-1) while the volume of distribution was 4.30 ± 1.12 and 6.05 ± 2.22 l, respectively. It was not possible to obtain the corresponding values from PAeq data owing to the lack of blood time course data. | Berthet A, Bouchard M, Vernez D (2012) Toxicokinetics of captan and folpet biomarkers in dermally exposed volunteers. Journal of applied toxicology : JAT 32, 202-209 [PubMed:21381058] [show Abstract] To better assess biomonitoring data in workers exposed to captan and folpet, the kinetics of ring metabolites [tetrahydrophthalimide (THPI), phthalimide (PI) and phthalic acid] were determined in urine and plasma of dermally exposed volunteers. A 10 mg kg(-1) dose of each fungicide was applied on 80 cm(2) of the forearm and left without occlusion or washing for 24 h. Blood samples were withdrawn at fixed time periods over the 72 h following application and complete urine voids were collected over 96 h post-dosing, for metabolite analysis. In the hours following treatment, a progressive increase in plasma levels of THPI and PI was observed, with peak levels being reached at 24 h for THPI and 10 h for PI. The ensuing elimination phase appeared monophasic with a mean elimination half-life (t(½) ) of 24.7 and 29.7 h for THPI and PI, respectively. In urine, time courses PI and phthalic acid excretion rate rapidly evolved in parallel, and a mean elimination t(½) of 28.8 and 29.6 h, respectively, was calculated from these curves. THPI was eliminated slightly faster, with a mean t(½) of 18.7 h. Over the 96 h period post-application, metabolites were almost completely excreted, and on average 0.02% of captan dose was recovered in urine as THPI while 1.8% of the folpet dose was excreted as phthalic acid and 0.002% as PI, suggesting a low dermal absorption fraction for both fungicides. This study showed the potential use of THPI, PI and phthalic acid as key biomarkers of exposure to captan and folpet. | Berthet A, Bouchard M, Danuser B (2012) Toxicokinetics of captan and folpet biomarkers in orally exposed volunteers. Journal of applied toxicology : JAT 32, 194-201 [PubMed:21381057] [show Abstract] The time courses of key biomarkers of exposure to captan and folpet was assessed in accessible biological matrices of orally exposed volunteers. Ten volunteers ingested 1 mg kg(-1) body weight of captan or folpet. Blood samples were withdrawn at fixed time periods over the 72 h following ingestion and complete urine voids were collected over 96 h post-dosing. The tetrahydrophthalimide (THPI) metabolite of captan along with the phthalimide (PI) and phthalic acid metabolites of folpet were then quantified in these samples. Plasma levels of THPI and PI increased progressively after ingestion, reaching peak values ~10 and 6 h post-dosing, respectively; subsequent elimination phase appeared monophasic with a mean elimination half-life (t(½) ) of 15.7 and 31.5 h, respectively. In urine, elimination rate time courses of PI and phthalic acid evolved in parallel, with respective t(½) of 27.3 and 27.6 h; relatively faster elimination was found for THPI, with mean t(½) of 11.7 h. However, phthalic acid was present in urine in 1000-fold higher amounts than PI. In the 96 h period post-treatment, on average 25% of folpet dose was excreted in urine as phthalic acid as compared with only 0.02% as PI. The corresponding value for THPI was 3.5%. Overall, THPI and PI appear as interesting biomarkers of recent exposure, with relatively short half-lives; their sensitivity to assess exposure in field studies should be further verified. Although not a metabolite specific to folpet, the concomitant use of phthalic acid as a major biomarker of exposure to folpet should also be considered. | Arce GT, Gordon EB, Cohen SM, Singh P (2010) Genetic toxicology of folpet and captan. Critical reviews in toxicology 40, 546-574 [PubMed:20569196] [show Abstract] Folpet and captan are fungicides whose genotoxicity depends on their chemical reaction with thiols. Multiple mutagenicity tests have been conducted on these compounds due to their positive activity in vitro and their association with gastrointestinal tumors in mice. A review of the collective data shows that these compounds have in vitro mutagenic activity but are not genotoxic in vivo. This dichotomy is primarily due to the rapid degradation of folpet and captan in the presence of thiol-rich matrices typically found in vivo. Genotoxicity has not been found in the duodenum, the mouse tumor target tissue. It is concluded that folpet like captan presents an unlikely risk of genotoxic effects in humans. | Zainal H, Que Hee SS (2003) Folpet permeation through nitrile gloves. Applied occupational and environmental hygiene 18, 658-668 [PubMed:12909534] [show Abstract] The aim of this study was to investigate whether two different brands of unsupported and unlined nitrile gloves protected against aqueous emulsions of a Folpet wettable powder (50% Folpet) using an ASTM type-I-PTC 600 permeation cell at 30.0 +/- 0.1 degrees C held in a shaking water bath. An analytical method to determine Folpet using the internal standard method was first developed based on gas chromatography-mass spectrometry (GC-MS), and gas chromatography-electron capture detection (GC-ECD). A novel pyrolysis GC-ECD technique that quantified the thermal degradation product phthalimide had pg sensitivity suitable to detect the trace amounts of Folpet that permeated. The on-column conversion was (68.0 +/- 9.5) percent at 170 degrees C over the folpet injected mass range of 3 to 148 pg. The challenge solution in the permeation cell was 1.4 mg/mL aqueous emulsion of Folpet wettable powder, and 2-propanol was the collection solvent. After evaporation of the collection solvent, the time weighted average rate of permeation of Folpet through SafeSkin nitrile (an exams type of glove) after 8 hours was (42.1 +/- 2.9) ng/cm(2)/min compared with (2.04 +/- 0.69) ng/cm(2)/min for the Sol-Vex nitrile (industrial chemical resistant), the latter being about 21 times more protective and also near the limits of detection. The respective values after 4 hours of exposure were (28.4 +/- 1.2) and (0.65 +/- 0.36) ng/cm(2)/min. Diagnostic reflectance infrared minima of both challenge and collection sides of the gloves showed small changes in wave number and intensity values after 8 hours of exposure, with Folpet being detected in dried spots on the challenge side. GC-ECD-based permeation and IR reflectance data indicated high chemical resistance of the Sol-Vex gloves to an aqueous emulsion of Folpet. | Cabras P, Angioni A, Caboni P, Garau VL, Melis M, Pirisi FM, Cabitza F (2000) Distribution of folpet on the grape surface after treatment. Journal of agricultural and food chemistry 48, 915-916 [PubMed:10725173] [show Abstract] Field trials were carried out to evaluate whether folpet sprayed on grapevines penetrated the epicuticular wax and cell walls of grapes. Folpet showed poor penetration into the epicuticular wax; it was found almost totally on the surface. Despite its low solubility in water, perhaps due to the presence of adjuvants, its residues showed such a high resistance to washing that the action of rain was negligible in decreasing residues. | Gilvydis DM, Walters SM, Spivak ES, Hedblad RK (1986) Residues of captan and folpet in strawberries and grapes. Journal - Association of Official Analytical Chemists 69, 803-806 [PubMed:3771451] [show Abstract] Fresh strawberries and grapes grown in Michigan and Indiana were surveyed for residues of captan and folpet, 2 fungicides commonly used on these crops. The fungicides were reportedly applied to the crops by overhead irrigation, tractor sprayer, or aerial spraying, in amounts ranging from 0.5 to 6 lb formulation/acre for captan and from 1 to 4 lb formulation/acre for folpet. Reported dates of last application ranged from just 2 days to nearly 5 months before samples were collected. Twenty-eight strawberry samples and 24 grape samples were collected of crops field-treated with one or both of these fungicides. Samples were analyzed by previously described methodology. Captan residues were found in all strawberry samples, ranging from less than 0.01 to 1.5 ppm. Folpet was found in only one strawberry sample at 0.041 ppm. Captan residues were found in only 6 grape samples, ranging from less than 0.01 to 0.082 ppm. Folpet residues were found in 12 grape samples, ranging from less than 0.01 to 0.50 ppm. All residues were well below the current tolerances of 25 ppm for both captan and folpet in strawberries and 50 ppm for captan and 25 ppm for folpet in grapes. Residue levels of these surface-applied, nonsystemic fungicides were inconsistent with amounts and dates of application, most likely because of variations in weather conditions, especially rainfall. Residues were quite stable in frozen sample homogenates, declining only 5-10% after 2 months. |
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