Captafol is a

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, ...

.Captafol
from Extension Toxicology Network It is used to control almost all fungal diseases of plants except powdery mildews. It is believed to be a 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 ...

, and production for use as a fungicide in the United States stopped in 1987. Its continued use from existing stocks was allowed, but in 1999 the

Environmental Protection Agency Environmental Protection Agency may refer to the following government organizations: * Environmental Protection Agency (Queensland), Australia * Environmental Protection Agency (Ghana) * Environmental Protection Agency (Ireland) * Environmenta ...

banned its use on all crops except onions, potatoes, and tomatoes. In 2006 even these exceptions were disallowed, so currently its use on all crops is banned in the United States. Several other countries have followed suit since 2000, and as of 2010, no countries are known to allow the use of captafol on food crops. Currently, the

National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the List of United States federal agencies, United States federal agency responsible for conducting research and making recommendations for the prevention of work-related occ ...

established a

recommended exposure limit A recommended exposure limit (REL) is an occupational exposure limit that has been recommended by the United States National Institute for Occupational Safety and Health. The REL is a level that NIOSH believes would be protective of worker safety ...

of 0.1 mg/m³ for dermal exposures. Captafol was disclosed in US patent 3,178,447 (1965). Its synergistic mixture with

thiabendazole Tiabendazole (International Nonproprietary Name, INN, British Approved Name, BAN), also known as thiabendazole (Australian Approved Name, AAN, United States Adopted Name, USAN) or TBZ and the trade names Mintezol, Tresaderm, and Arbotect, is a pr ...

was described in US patent 4092422 (1978). International trade in captafol is regulated by the

Rotterdam Convention The Rotterdam Convention (formally, the Rotterdam Convention on the Prior Informed Consent Procedure for Certain Hazardous Chemicals and Pesticides in International Trade) is a multilateral treaty to promote shared responsibilities in relatio ...

Synthesis

Captafol can be obtained by reacting the sodium salt of

1,2,3,6-Tetrahydrophthalimide Onekama ( ) is a village in Manistee County in the U.S. state of Michigan. The population was 399 at the 2020 census. The village is located on the northeast shore of Portage Lake and is surrounded by Onekama Township. The town's name is derive ...

in benzene with 1,1,2,2-Tetrachloroethylsulfenyl chloride.Thomas A. Unger: Pesticide Synthesis Handbook. William Andrew, 1996, ISBN 0-8155-1853-6, p. 453 left, Synthesis of Captafol

Synthesis

References

Further reading