Pentachloroaniline

log Kow= 5.08

4.59

Danger

H301 (91.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 41,687(2), indicates that pentachloroaniline is expected to be immobile in soil(SRC). Volatilization of pentachloroaniline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.25X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Pentachloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-6 mm Hg(SRC), determined from a fragment constant method(5). Anilines (aromatic amines) are expected to bind strongly to humus or organic matter in soils(6,7) due to the high reactivity of the aromatic amino group(SRC). After 2 weeks of exposure to various bacterial cultures from soil incubated at 25 °C under aerobic conditions, pentachloroaniline did not degrade(8).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 41,687(2) indicates that pentachloroaniline is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.25X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), a BCF of 363(6) suggests bioconcentration in aquatic organisms is high. Pentachloroaniline degrades through preferential ortho chlorine removal displaying a rate constant of 0.017 day-1 (half-life of 40 days) under anaerobic, sulfate-reducing sediment conditions(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pentachloroaniline, which has an estimated vapor pressure of 3.5X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phase in the ambient atmosphere. Vapor-phase pentachloroaniline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 12 days(SRC) from its estimated rate constant of 1.33X10-12 cu cm/ molecule sec(3). Particulate-phase pentachloroaniline may be removed from the air by wet and dry deposition(SRC). Aniline compounds structurally similar to pentachloroaniline have been found to photolyze in the ambient environment suggesting that pentachloroaniline may photolyze when exposed to environmental UV radiation(SRC).

FDA total diet samples - average concn of pentachloroaniline in ppm (daily intake, ug/day): 1978-1979 U.S. infant and toddler diets 0.0087 (0.177)(1); 1979-1980 U.S. infant and toddler diets 0.0050 (0.102)(2); 1979-1980 U.S. adult diet in garden fruit 0.0001 (0.0109), oils and fats 0.0083 (0.585) and sugar and adjuncts 0.0004 (0.0320)(3); 1978-1979 U.S. adult diet in potatoes 0.0002 (0.0399), garden fruits 0.0001 (0.0107) and oils and fats 0.017 (0.123)(4); 1980-1982 U.S. infant and toddler diets 0.0037 (0.0752)(5); 1980-1982 U.S. adult diet in root vegetable 0.0001 (0.0024), garden fruits <0.0001 (0.0026), oil and fats 0.0034 (0.246) and sugar and adjuncts 0.0001 (0.0112)(6).

1981-1986 Pentachloroaniline was detected in one U.S. food sample of 20,000 (range 0.1-0.5 ppm)(1); 1972-1973 in U.S. food avg concn 0.003 ppm (range 0.003-0.032 ppm)(2); 1974-1975 in food avg concn 0.002 ppm (range 0.003-0.035 ppm)(3); 1982-1986 in 11 of 19,851 samples (range 0.05-0.50 ppm)(4); 1971-1972 in U.S. foods (range 0.005-0.023 ppm) in oils, fats and shortening(5); 1973-1974 in U.S. foods avg concn 0.004 ppm (range 0.004-0.050 ppm)(6); 1976-1977 in U.S. infant and toddler diets range 0.004-0.022 ppm (infants) and range 0.002-0.025 ppm (toddlers) in oils and fats(7); 1975-1976 in U.S. adult diets (range 0.007-0.018 ppm) in oils, fats and shortening(8); 1977-1978 in U.S. adult diet (range 0.001-0.024 ppm) in leaf foods(9); 1977-1978 in U.S. infant and toddler diets range 0.005-0.029 ppm (infant) and range 0.002-0.018 ppm (toddler)(10).

Pentachloroaniline appears to be a metabolite of quintozene, a fungicide no longer registered in the U.S., and has been found in both carrots and potatoes(1). Pentachloroaniline was detected in leaf and stem vegetables between 1975-76 in 69 of 5,631 samples, 1 of 3,262 samples in fish and shellfish, 3 of 3,857 samples in root vegetables, and 1 of 7,071 samples in vine and ear vegetables(concentration not specified)(2). Of 27,065 samples of food collected and analyzed in 10 state food laboratories between 1988-1989, pentachloroaniline was found in 1 sample (concn not specified)(3). Pentachloroaniline was detected in foods representative of the total diet of the U.S. population (concn not specified) from 1982-1991(4-6). Residues have been found within peanut butter samples; avg concn 42 ppb (range 3.4-140 ppb)(7).

After treating lettuce with quintozene, pentachloroaniline was detected ranging from 0.14 to 1.52 ppm within lettuce samples. Pentachloroaniline is assumed to reside in lettuce through degradation of quintozene occurring within the plant itself or from degradation of quintozene in the soil and uptake of pentachloroaniline through the root system or a combination of the 2 processes(1).

The Koc of pentachloroaniline is 41,687(1) in soil. According to a classification scheme(2), this Koc value suggests that pentachloroaniline is expected to be immobile in soil. Anilines (aromatic amines) are expected to bind strongly to humus or organic matter in soils(3,4) due to the high reactivity of the aromatic amino group(SRC).

AEROBIC: After 2 weeks of exposure to different bacterial cultures incubated at 25 °C in both moist and submerged soil, pentachloroaniline did not degrade(1). ANAEROBIC: Using a sulfate reducing sediment taken from the Tsurumi river Japan, pentachloroaniline degraded step wise from 2,3,4,5-tetrachloroaniline, 2,3,5-trichloroaniline, 3,5-dichloroaniline, 3-chloroaniline to aniline. Pentachloroaniline degrades through preferential ortho chlorine removal displaying a rate constant of 0.017 day-1 with a half-life of 40 days(2).

SOIL: Pentachloroaniline was detected in soil samples from a field previously sprayed with quintozene ranging from 0.1 ppm to 3.75 ppm(1). From a soil in which quintozene had been extensively used, pentachloroaniline was detected at 10.1 ppm(2). In Belgium, soil from a lettuce field contained 0.85 ppm of pentachloroaniline while soil from a chicory field contained 2.5 ppm. In Denmark, a field soil sample contained 1.8 ppm while soil from a greenhouse field in the Netherlands contained trace amounts of pentachloroaniline(3).

A BCF of 363(1) and 6026(2) were reported for pentachloroaniline using guppies over a 10 day period in a flow through system and a static system, respectively. According to a classification scheme(3), this range of BCF for pentachloroaniline suggests the potential for bioconcentration in aquatic organisms ranges from high to very high.

The Henry's Law constant for pentachloroaniline is estimated as 4.25X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that pentachloroaniline is expected to be essentially nonvolatile from water surfaces(2). Pentachloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-6 mm Hg(SRC), determined from a fragment constant method(3).

The rate constant for the vapor-phase reaction of pentachloroaniline with photochemically-produced hydroxyl radicals has been estimated as 1.33X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Pentachloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Aniline compounds structurally similar to pentachloroaniline have been found to photolyze in the ambient environment suggesting that pentachloroaniline may photolyze when exposed to environmental UV radiation(SRC).

PENTACHLOROANILINE IS A METABOLITE OF THE PESTICIDE PENTACHLORONITROBENZENE (QUINTOZENE) IN ANIMALS, PLANTS, SOIL, ETC.

PENTACHLOROANILINE LEVELS IN URINE WERE MEASURED & CORRELATED TO THE TYPE OF PCNB FORMULATION USED.

PURE PENTACHLORONITROBENZENE WAS ADMIN TO RHESUS MONKEYS AS SINGLE ORAL DOSES OF 0.5, 2, OR 91 MG/KG & IN A 70-DAY FEEDING STUDY @ LEVEL OF 2 PPM IN DAILY DIET. PENTACHLOROANILINE WAS A MAJOR METABOLITE.

PENTACHLORONITROBENZENE WAS ADMIN TO RATS AND BEAGLE DOGS, IN THE DIET, AND TO COWS. PENTACHLOROANILINE WAS FOUND IN TISSUE OF TREATED ANIMALS OF ALL 3 SPECIES.

For more Metabolism/Metabolites (Complete) data for PENTACHLOROANILINE (8 total), please visit the HSDB record page.

An environmental degradation product of the fungicide quintozene; No longer registered for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]