This article is about the fungicide. It is not to be confused with ethyl mercaptan, which is used as an odorant for liquefied petroleum gas or kapton, a type of plastic film.
Although it can be applied on its own, Captan is often added as a component of other pesticide mixtures. It is used to control diseases on a number of fruits[4] and vegetables as well as ornamental plants. It also improves the outward appearance of many fruits, making them brighter and healthier-looking. Captan is utilized by both home and agricultural growers and is often applied during apple production. It is also active against certain oomycetes, such as Pythium, making it useful for controlling damping off.[5]
BiodegradationEdit
The compound biodegrades with half life of less than 1 day in soil.[3]
Potential health effectsEdit
Captan was previously cited as Group B2, a probable human carcinogen by the US Environmental Protection Agency (EPA),[6] but was reclassified in 2004. Since the mode of action has been established as a proliferative response (in mice only) after intestinal villi are disrupted, captan has been deemed not likely to cause tumors at doses that do not irritate the intestine. The EPA now states, "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. Therefore, captan is not likely to be a human carcinogen nor pose cancer risks of concern when used in accordance with approved product labels.[7] A similar reclassification has been made for folpet, a structurally related fungicide, which shares a common mechanism of toxicity.[8][9] A key finding for captan (and folpet) is these fungicides are not mutagenic in the animal (in vivo).[10][11][12]
ProductionEdit
It is the product of the reaction trichloromethylsulfenyl chloride with sodium salt of tetrahydrophthalamide.[3]
^ abcFranz Müller; Peter Ackermann; Paul Margot (2012). "Fungicides, Agricultural, 2. Individual Fungicides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o12_o06. ISBN978-3527306732.
^Dowling, Madeline; Peres, Natalia; Villani, Sara; Schnabel, Guido (2020). "Managing Colletotrichum on Fruit Crops: A "Complex" Challenge". Plant Disease. 104 (9): 2301–2316. doi:10.1094/PDIS-11-19-2378-FE. ISSN 0191-2917. PMID 32689886. S2CID 219479598.
^Review of Fungicides for Control of Phytophthora and Pythium Diseases on Potted Ornamentals
^EPA Captan Reregistration Eligibility Decision Facts October 6, 2006, at the Wayback Machine
^US EPA. 2004. Captan: Cancer Reclassification; Amendment of Reregistration Eligibility Decision; Notice of Availability. Federal Register 69: 68357-68360
^Bernard, B. K., and Gordon, E. B. 2000. An evaluation of the common mechanism approach to the Food Quality Protection Act: Captan and four related fungicides, a practical example. Int J Toxicol 19: (1): 43-61.
^Kidwell, J. (2010). Cancer Assessment Document. Second Evaluation of the Carcinogenic Potential of Folpet. PC Code 081601. Cancer Assessment Review Committee, Health Effects Division, Office of Pesticide Programs, U.S. Environmental Protection Agency, USA. Folpet Cancer Assessment Document Final. Memorandum to Abdallah Khasawinah, RAB IV, Health Effect Division (7505P) and Tony Kish, Product Manager, Team 22, Fungicide Branch, Registration Division (7505P), through Mary Manibusan and Jess Rowland, Co-Chairs Cancer Assessment Review Committee, Health Effects Division (7509P), 53 Pages, October 13, 2010.
^Cohen, S. M., Gordon, E. B., Singh, P., Arce, G. T., and Nyska, A. 2010. Carcinogenic Mode of Action of Folpet in Mice and Evaluation of Its Relevance to Humans. Critical Reviews in Toxicology 40: (6): 531-545.
^Arce, G. T., Gordon, E. B., Cohen, S. M., and Singh, P. 2010. Genetic Toxicology of Folpet and Captan. Critical Reviews in Toxicology 40: (6): 546-574.
^Gordon, E. B. 2010b. Captan and Folpet. In: R. Krieger, ed. Hayes Handbook of Pesticide Toxicology pp. 1915-1949. Elsevier, New York
External linksEdit
Captan Technical Fact Sheet - National Pesticide Information Center
Captan General Fact Sheet - National Pesticide Information Center
Captan Pesticide Information Profile - Extension Toxicology Network
CDC - NIOSH Pocket Guide to Chemical Hazards - Captan
October 17, 2023
captan, this, article, about, fungicide, confused, with, ethyl, mercaptan, which, used, odorant, liquefied, petroleum, kapton, type, plastic, film, general, pesticide, that, belongs, phthalimide, class, fungicides, white, solid, although, commercial, samples, . This article is about the fungicide It is not to be confused with ethyl mercaptan which is used as an odorant for liquefied petroleum gas or kapton a type of plastic film Captan is a general use pesticide GUP that belongs to the phthalimide class of fungicides It is a white solid although commercial samples appear yellow or brownish 3 Captan NamesIUPAC name 3aR 7aS 2 Trichloromethyl sulfanyl 3a 4 7 7a tetrahydro 1H isoindole 1 3 2H dioneIdentifiersCAS Number 133 06 2 Y3D model JSmol Interactive imageInteractive imageChEBI CHEBI 34608 NChEMBL ChEMBL388676 YChemSpider 8287 YECHA InfoCard 100 004 626KEGG C14438 YPubChem CID 8606UNII EOL5G26Q9F YCompTox Dashboard EPA DTXSID9020243InChI InChI 1S C9H8Cl3NO2S c10 9 11 12 16 13 7 14 5 3 1 2 4 6 5 8 13 15 h1 2 5 6H 3 4H2 YKey LDVVMCZRFWMZSG UHFFFAOYSA N YInChI 1 C17H19ClN2O3 c18 13 7 3 4 8 14 13 19 15 21 9 10 20 16 22 11 5 1 2 6 12 11 17 20 23 h3 4 7 8 11 12H 1 2 5 6 9 10H2 H 19 21 t11 12 m1 s1Key PIBUBEBGJVBNLY VXGBXAGGBJInChI 1 C9H8Cl3NO2S c10 9 11 12 16 13 7 14 5 3 1 2 4 6 5 8 13 15 h1 2 5 6H 3 4H2Key LDVVMCZRFWMZSG UHFFFAOYABSMILES C1C CC C H 2 C H 1C O N C2 O SC Cl Cl ClClC Cl Cl SN1C O C2C C C CC2C1 OPropertiesChemical formula C 9H 8Cl 3N O 2SMolar mass 300 58 g mol 1Appearance white solid yellow powder commercial 1 Density 1 74 g cm3 2 Melting point 178 C 352 F 451 K decomposes Boiling point N AHazardsOccupational safety and health OHS OSH Main hazards combustible potential occupational carcinogen 1 NIOSH US health exposure limits PEL Permissible none 1 REL Recommended Ca TWA 5 mg m3 1 IDLH Immediate danger N D 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Applications 2 Biodegradation 3 Potential health effects 4 Production 5 References 6 External linksApplications EditAlthough it can be applied on its own Captan is often added as a component of other pesticide mixtures It is used to control diseases on a number of fruits 4 and vegetables as well as ornamental plants It also improves the outward appearance of many fruits making them brighter and healthier looking Captan is utilized by both home and agricultural growers and is often applied during apple production It is also active against certain oomycetes such as Pythium making it useful for controlling damping off 5 Biodegradation EditThe compound biodegrades with half life of less than 1 day in soil 3 Potential health effects EditCaptan was previously cited as Group B2 a probable human carcinogen by the US Environmental Protection Agency EPA 6 but was reclassified in 2004 Since the mode of action has been established as a proliferative response in mice only after intestinal villi are disrupted captan has been deemed not likely to cause tumors at doses that do not irritate the intestine The EPA now states 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 Therefore captan is not likely to be a human carcinogen nor pose cancer risks of concern when used in accordance with approved product labels 7 A similar reclassification has been made for folpet a structurally related fungicide which shares a common mechanism of toxicity 8 9 A key finding for captan and folpet is these fungicides are not mutagenic in the animal in vivo 10 11 12 Production EditIt is the product of the reaction trichloromethylsulfenyl chloride with sodium salt of tetrahydrophthalamide 3 References Edit a b c d e NIOSH Pocket Guide to Chemical Hazards 0099 National Institute for Occupational Safety and Health NIOSH Captan Icsc a b c Franz Muller Peter Ackermann Paul Margot 2012 Fungicides Agricultural 2 Individual Fungicides Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 o12 o06 ISBN 978 3527306732 Dowling Madeline Peres Natalia Villani Sara Schnabel Guido 2020 Managing Colletotrichum on Fruit Crops A Complex Challenge Plant Disease 104 9 2301 2316 doi 10 1094 PDIS 11 19 2378 FE ISSN 0191 2917 PMID 32689886 S2CID 219479598 Review of Fungicides for Control of Phytophthora and Pythium Diseases on Potted Ornamentals EPA Captan Reregistration Eligibility Decision Facts Archived October 6 2006 at the Wayback Machine US EPA 2004 Captan Cancer Reclassification Amendment of Reregistration Eligibility Decision Notice of Availability Federal Register 69 68357 68360 Bernard B K and Gordon E B 2000 An evaluation of the common mechanism approach to the Food Quality Protection Act Captan and four related fungicides a practical example Int J Toxicol 19 1 43 61 Kidwell J 2010 Cancer Assessment Document Second Evaluation of the Carcinogenic Potential of Folpet PC Code 081601 Cancer Assessment Review Committee Health Effects Division Office of Pesticide Programs U S Environmental Protection Agency USA Folpet Cancer Assessment Document Final Memorandum to Abdallah Khasawinah RAB IV Health Effect Division 7505P and Tony Kish Product Manager Team 22 Fungicide Branch Registration Division 7505P through Mary Manibusan and Jess Rowland Co Chairs Cancer Assessment Review Committee Health Effects Division 7509P 53 Pages October 13 2010 Cohen S M Gordon E B Singh P Arce G T and Nyska A 2010 Carcinogenic Mode of Action of Folpet in Mice and Evaluation of Its Relevance to Humans Critical Reviews in Toxicology 40 6 531 545 Arce G T Gordon E B Cohen S M and Singh P 2010 Genetic Toxicology of Folpet and Captan Critical Reviews in Toxicology 40 6 546 574 Gordon E B 2010b Captan and Folpet In R Krieger ed Hayes Handbook of Pesticide Toxicology pp 1915 1949 Elsevier New YorkExternal links EditCaptan Technical Fact Sheet National Pesticide Information Center Captan General Fact Sheet National Pesticide Information Center Captan Pesticide Information Profile Extension Toxicology Network EPA Captan Reregistration Eligibility Decision Facts CDC NIOSH Pocket Guide to Chemical Hazards Captan Retrieved from https en wikipedia org w index php title Captan amp oldid 1160031793, wikipedia, wiki, book, books, library,
