Captan Structural Formula V
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Captan is a general use pesticide (GUP) that belongs to the phthalimide class of
fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...
s. It is a white solid, although commercial samples appear yellow or brownish.


Applications

Although it can be applied on its own, Captan is often added as a component of other
pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...
mixtures. It is used to control diseases on a number of
fruits In botany, a fruit is the seed-bearing structure in flowering plants (angiosperms) that is formed from the ovary after flowering. Fruits are the means by which angiosperms disseminate their seeds. Edible fruits in particular have long propaga ...
and
vegetables Vegetables are edible parts of plants that are consumed by humans or other animals as food. This original meaning is still commonly used, and is applied to plants collectively to refer to all edible plant matter, including flowers, fruits, ...
as well as
ornamental plant Ornamental plants or ''garden plants'' are plants that are primarily grown for their beauty but also for qualities such as scent or how they shape physical space. Many flowering plants and garden varieties tend to be specially bred cultivars th ...
s. 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 Damping off (or damping-off) is a horticultural disease or condition, caused by several different pathogens that kill or weaken seeds or seedlings before or after they germinate. It is most prevalent in wet and cool conditions. Symptoms There ar ...
.


Biodegradation

The compound biodegrades with half life of less than 1 day in soil.


Potential health effects

Captan was previously cited as Group B2, a probable human
carcinogen A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...
by the US Environmental Protection Agency (EPA), but was reclassified in 2004. Since the mode of action has been established as a proliferative response (in
mice A mouse (: mice) is a small rodent. Characteristically, mice are known to have a pointed snout, small rounded ears, a body-length scaly tail, and a high breeding rate. The best known mouse species is the common house mouse (''Mus musculus' ...
only) after intestinal villi are disrupted, captan has been deemed not likely to cause
tumor A neoplasm () is a type of abnormal and excessive growth of tissue. The process that occurs to form or produce a neoplasm is called neoplasia. The growth of a neoplasm is uncoordinated with that of the normal surrounding tissue, and persists ...
s 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 Hyperplasia (from ancient Greek ὑπέρ ''huper'' 'over' + πλάσις ''plasis'' 'formation'), or hypergenesis, is an enlargement of an organ or tissue caused by an increase in the amount of Tissue (biology), organic tissue that results from ...
. 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 Cancer is a group of diseases involving Cell growth#Disorders, abnormal cell growth with the potential to Invasion (cancer), invade or Metastasis, spread to other parts of the body. These contrast with benign tumors, which do not spread. Po ...
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
fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...
s are not mutagenic in the animal ( in vivo).Gordon, E. B. 2010b. Captan and Folpet. In: R. Krieger, ed. Hayes Handbook of Pesticide Toxicology pp. 1915-1949. Elsevier, New York


Production

It is the product of the reaction trichloromethylsulfenyl chloride with sodium salt of tetrahydrophthalamide, which is derived from tetrahydrophthalic anhydride.


References


External links


Captan Technical Fact Sheet - National Pesticide Information CenterCaptan General Fact Sheet - National Pesticide Information Center
* ttps://web.archive.org/web/20061006123222/http://www.epa.gov/oppsrrd1/REDs/factsheets/0120fact.pdf EPA Captan Reregistration Eligibility Decision Factsbr>CDC - NIOSH Pocket Guide to Chemical Hazards - Captan
{{Authority control Aldehyde dehydrogenase inhibitors Fungicides Pesticides Sulfenamides Imides Trichloromethyl compounds Isoindoles