Каптан: Свойства, применение и оценка рисков

chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 415310696
| Name = Captan
| ImageFile = Captan Structural Formula V.1. svg
| ImageName = Captan
| ImageFile1 = Captan from xtal 1981 CM 3D balls. png
| IUPACName = (3aR,7aS) 2 [(Trichloromethyl)sulfanyl] 3a,4,7,7a tetrahydro 1H isoindole 1,3(2H) dione
|Section1=
|Section2=Chembox Properties
| C=9 | H=8 | Cl=3 | N=1 | O=2 | S=1
| Density = 1.74 g/cm3
| MeltingPtC = 178
| MeltingPt notes = (decomposes)
| BoilingPt = N/A
| Appearance = white solid; yellow powder (commercial)
| MainHazards = combustible, potential occupational carcinogen

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 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.

The compound biodegrades with half life of less than 1 day in soil. 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. A similar reclassification has been made for folpet, a structurally related fungicide, which shares a common mechanism of toxicity. A key finding for captan (and folpet) is these fungicides are not mutagenic in the animal (in vivo).

It is the product of the reaction trichloromethylsulfenyl chloride with sodium salt of tetrahydrophthalamide.