SPECTRUM

Chemical Fact Sheet

Chemical Abstract Number (CAS #) 2425061
CASRN 2425-06-1
SynonymsCaptafol
Difolatan
4-Cyclohexene-1,2-dicarboximide N-((1,1,2,2-tetrachloro-ethyl)thio)-
Analytical Method EPA Method 8081
Molecular FormulaC10H9Cl4NO2S

Link to the National Library of Medicine's Hazardous Substances
Database for more details on this compound.

Use FUNGICIDE ON APPLES, VEGETABLES, POTATOES, FIELD CROPS, SEED TREATMENT /IT IS USED AS PROTECTANT-ERADICANT FUNGICIDE ON PEANUTS, CITRUS, CRANBERRIES PINEAPPLES, MACADAMIA NUTS, TARO, ONIONS, TOMATOES SWEET CORN (FL), CUCUMBERS, SOUR CHERRIES, BLUEBERRIES, PRUNES SEED PROTECTANT ON RICE, COTTON, PEANUTS. It is widely used to control foliage and fruit disease of tomatoes, coffee berry disease, potato blight, tapping panel disease of rubber and many other diseases. It is also used in the lumber and timber industries to reduce losses from wood rot fungi in logs and wood products. Control of scab of pome fruit; shot-hole of stone fruit; peach leaf curl; downy mildew and black rot of vines; early and late blights of potatoes; Alternaria and mildew of carrots; celery leaf spot; Septoria of wheat; Rhynchosporium of barley; and various diseases of tomatoes, coffee, groundnuts, citrus fruit, pineapples, macadamia nuts, onions, cucurbits, maize, sorghum, etc. Used as a seed treatment for control of Pythium and Phoma species and other emergence diseases of beet, cotton, groundnuts, and rice. Also used as a wound protectant for grafting and pruning wounds and cankers on trees; and in the timber industry as a wood preservative. /IT IS RECOMMENDED FOR USE ON MELONS AND STONE FRUITS FOR CONTROL OF LEAF SPOT, MILDEW, SHOT HOLE, ANTHRACNOSE, GRAY MOLD & OTHERS.
Consumption Patterns APPROX 29% AS A FUNGICIDE ON APPLES; APPROX 29% AS A FUNGICIDE ON VEGETABLES; APPROX 24% AS A FUNGICIDE ON POTATOES; APPROX 18% AS FUNGICIDE FOR SEED TREATMENT & FIELD CROPS (1975)
Apparent Color White, solid ; Colorless crystalline solid ; Pale yellow crystals
Melting Point 160-161 DEG C
Molecular Weight 349.06
Sensitivity Data Skin and respiratory sensitization and irritation.
Environmental Impact Difolatan is a non-systemic fungicide used primarily on foliage for the control of fungal disease. It is also used in the lumber and timber industry against wood rot fungi. The release of difolatan to the environment occurs from these uses. Difolatan strongly adsorbs to soil and should therefore remain in the upper layers of soil. In soil, difolatan is transformed by biodegradation and hydrolysis. The half-life of difolatan in soil is about 11 days. Both biodegradation and hydrolysis are expected to be the major pathways for the loss of difolatan in water. The half-life of difolatan in a river water was estimated to be 0.3 day. Volatilization from water or soil should be negligible. The bioconcentration of difolatan in aquatic organisms should not be important. Reaction of difolatan with photochemically produced hydroxyl radicals and ozone will be the important loss processes in the atmosphere. The half-life of difolatan in air can be estimated to be less than 1.4 hrs. Partial removal of difolatan will also occur as a result of dry and wet deposition. Difolatan has rarely been detected in surface water and groundwater in the U.S. It has been detected at very low levels in some foods. The applicators of the fungicide and farm workers are the most likely people for exposure to difolatan by inhalation and dermal routes.
Environmental Fate IT IS PERSISTENT ON PLANT SURFACES FOR 7-10 DAYS. TERRESTRIAL FATE: Both biodegradation and hydrolysis may be the major processes for the loss of difolatan from most soils(1-2,SRC). In a laboratory experiment, the biodegradation half-life of difolatan in three soils was estimated to be in the range 23-55 days . The overall half-life of difolatan in soil is about 11 days and the degradation rate is independent of initial concn . A log Koc value in the range 3.32-3.33(4-5) indicates difolatan will strongly sorb to soil and therefore, leaching of difolatan from soils should not be an important fate process(6,SRC). Because of its negligible vapor pressure(7) and very low estimated Henry's Law constant(8), the volatilization of difolatan from dry and moist soil should be negligible. AQUATIC FATE: The two processes that control the fate of difolatan in water are hydrolysis and biodegradation(1-2). The estimated half-life of difolatan in a river is 0.3 day primarily due to biodegradation . Based on an estimated value of 2.155X10-9 atm-cu m/mole for Henry's Law constant, the rate of volatilization of difolatan from water will be negligibly small(4,SRC). A log Koc value in the range 3.32-3.33(6-7) suggests that difolatan may remain strongly sorbed to suspended solids and sediment in water(8,SRC). The estimated BCF values in the range 48-512(4,SRC) and the ability of fish to eliminate difolatan from the body indicates that bioconcentration of difolatan in aquatic organisms should not be important. ATMOSPHERIC FATE: Vapor phase difolatan reacts with photochemically produced hydroxyl radicals and ozone in the atmosphere. The estimated half-lives of difolatan in the atmosphere as a result of these reactions are 2.9 hr and 1.4 hr, respectively(1-3).
Drinking Water Impact SURFACE WATER: Following an accidental spill, the estimated concn of difolatan in Rhine River water at Schweizerhalle, Switzerland was 0.2-1 ug/l . GROUNDWATER: During a 1986-1987 survey, no difolatan was detected (detection limit 0.5 ug/l) in water from 4 farm wells in Ontario, Canada where the fungicide had been used .

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