КАПТАФОЛ

Химические свойства

Captafol is a white crystalline solid.

Использование

Captafol is used to control a wide range of fungal diseases on many crops.

Определение

ChEBI: A dicarboximide that captan in which the trichloromethyl group is replaced by a 1,1,2,2-tetrachloroethyl group. A broad-spectrum fungicide used to control diseases in fruit and potatoes, it is no longer approved for use in the European Community.

Общее описание

White crystalline solid with a slight, but pungent odor. Mp: 162°C. Practically insoluble in water. Only slightly soluble in organic solvents. Technical CAPTAFOL is a wettable light tan powder that is used as a fungicide. Inhaled dust irritates the respiratory tract. Irritates skin and damages eyes. Acute oral toxicity in humans is low. Not persistent in the environment (decomposes with a half-life of 11 days in the soil). Highly toxic to fish and other aquatic organisms.

Профиль реактивности

CAPTAFOL is non-flammable but, on heating, may decompose to generate toxic fumes, such as sulfur oxides, hydrogen sulfide, hydrochloric acid, and phosgene. Stable at room temperature when dry but readily hydrolysed, especially in an alkaline environment. CAPTAFOL and mixtures containing high concentrations of CAPTAFOL may react violently with alkali. Incompatible with acids, acid chlorides, acid anhydrides, and strong oxidizing agents. Sulfhydryl compounds such as glutathione and cysteine cause a rapid chemical decomposition.

Опасность

Absorbed by skin. Probable carcinogen.

Сельскохозяйственное использование

Fungicide: Captafol is a General Use Pesticide and used for the control of practically all forms of fungal diseases except powdery mildew. It is also used as a seed protectorant on cotton, rice and peanut crops. Not registered for use in the U.S. or in EU countries. There are 20 global suppliers.

Торговое название

CAPTATOL®; CAPTOFOL®; CRISFOLATAN®; DIFOLATAN®[C]; DIFOCAP®[C]; DIFOSAN®; FOLCID®; HAIPEN®; KENOFOL®; MERPAFOL®; ORTHO® 5865[C]; PILLARTAN®; SANSEAL®; SANSPOR®; SANTAR-SM®; SULFONIMIDE®; SULPHEIMIDE®

Контактные аллергены

Captafol is a pesticide, belonging to thiophthalimide group. Occupational contact dermatitis was reported in an agricultural worker who had multiple sensitizations

Профиль безопасности

Confirmed carcinogen with experimental carcinogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. A fungicide. When heated to decomposition it emits very toxic fumes of Cl-, NO,, and SOx

Возможный контакт

Captafol is a thiophthalimide fungicide. Those engaged in the manufacture, formulation, and application of this fungicide. Captafol is not currently registered for use on field crops or stored produce in the United States.

Канцерогенность

Captafol is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals and supporting data on mechanisms of carcinogenesis.

Экологическая судьба

The primary toxicity following captafol exposure probably occurs through a hypersensitivity mechanism. Most experiments suggest captafol to be DNA active.

Метаболический путь

Captafol contains an unstable tetrachloroethylthio (sulfenyl) moiety that has been shown to undergo rapid hydrolytic and metabolic degradation to tetrahydrophthalimide (2). By analogy with captan, presumably the tetrachloroethylthio moiety can be transferred to the sulfur atoms of thiols such as cysteine and glutathone. Thus in the presence of thiols such as glutathione, captafol is probably cleaved at the N-S bond to form thiophosgene (3) and other gaseous products such as hydrogen sulfide, hydrogen chloride and carbonyl sulfide. Thiophosgene is rapidly hydrolysed by water. The tetrachloroethylthio group and thiophosgene are believed to be intermediates in the formation of thiazolidine-2- thione-6carboxylic acid (4) which is an addition product with cysteine. A thiazolidine derivative of glutathione is also formed (5). Biotransformation of captafol in mammals generates primarily thiophosgene (3) and tetrahydrophthalimide (2). Tetrahydrophthalimide (2) and various of its derivatives are excreted in the urine. There were no reports of 2-thiazolidinethione-4-carboxylic acid (4) in the urine.

Перевозки

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN 2773 Phthalimide derivative pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Несовместимости

Reacts violently with bases, causing fire and explosion hazard. Not compatible with strong acids or acid vapor, oxidizers. Strong alkaline conditions contribute to instability. Attacks some metals.

Утилизация отходов

Hydrolysis.