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Common name captan (BSI, E-ISO, JMAF); captane ((m) F-ISO); captab (Republic of South Africa)
IUPAC name N-(trichloromethylthio)cyclohex-4-ene-1,2-dicarboximide
Chemical Abstracts name 3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione
CAS RN [133-06-2]
PHYSICAL CHEMISTRY
Composition Tech. is 90-95% pure. Mol. wt. 300.6 M.f. C9H8Cl3NO2S Form Colourless crystals; (tech. is a colourless to beige amorphous solid, with a pungent odour). M.p. 178 ºC (tech., 175-178 ºC) V.p. <1.3 mPa (25 ºC) KOW logP = 2.8 (25 ºC) Henry <1.18 ´ 10-1 Pa m3 mol-1 (calc.) S.g./density 1.74 (26 °C) Solubility In water 3.3 mg/l (25 ºC). In xylene 20, chloroform 70, acetone 21, cyclohexanone 23, dioxane 47, benzene 21, toluene 6.9, isopropanol 1.7, ethanol 2.9, diethyl ether 2.5 (all in g/kg, 26 ºC). Insoluble in petroleum oils. Stability Hydrolysed slowly at neutral pH, rapidly in alkali. Thermal DT50 >4 y (80 ºC), 14.2 d (120 ºC).
APPLICATIONS
Biochemistry Non-specific thiol reactant, inhibiting respiration.
Mode of action Fungicide with protective and curative action.
Uses Control of a wide range of fungal diseases, e.g. scab, Gloeosporium and other rots of pome fruit; shot-hole of stone fruit; peach leaf curl; brown rots of cherries, apricots, peaches, plums, and citrus fruit; downy mildew and black rot of vines; early and late blights of potatoes and tomatoes; Alternaria blight and leaf spot of carrots; anthracnose and downy mildew of cucurbits; leaf spot diseases of ornamentals; anthracnose and leaf spot diseases of tomatoes; brown patch on turf; Botrytis spp. on many crops; etc. Used on a large number of other crops. Used as a seed treatment or root dip for control of Pythium, Phoma, Rhizoctonia spp., etc. on maize, ornamentals, vegetables, oilseed rape, and other crops.
Phytotoxicity Non-phytotoxic if used as directed, but some varieties of apple (e.g. Red Delicious, Winesap) and pear (e.g. D'Anjou, Bosc) may be injured, as also may lettuce seeds and, at higher dosages, celery and tomato seeds.