Napropamide

271.35

271.35

239-333-3

DTXSID5024211

Colorless crystals; (tech., brown solid)|Brown solid|Light brown solid from n-pentane.|White crystals when pure

29242990

29.5

3.36

Brown Solid

1.0288 (rough estimate)

75 °C

414.44°C (rough estimate)

214.0±24.0 °C

1.5675 (estimate)

In water, 73 mg/l @ 20 deg C

0-6°C

1.72X10-7 mm Hg @ 25 deg C

5.8X10-5 mg/l @ 25 deg C

Oral-Rat LD50: 5000 mg/kg; Oral-Mouse LD50: 5000 mg/kg

Combustion produces toxic nitrogen oxide gas

No decomposition occurs over 16 h at 100 °C. Decomposed by sunlight. Stable to hydrolysis between pH 4 and 10 at 40 °C.

UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name RequiredUN3082 (liquid)

2

UE3600000

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

P264, P273, P280, P305+P351+P338, P337+P313, P391, P501

H319

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.

|Warning|H319 (99.37%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P273, P280, P305+P351+P338, P337+P313, P391, and P501|Aggregated GHS information provided by 163 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

URBAN/SUBURBAN: Napropamide was detected in ambient air samples from Kitakyushu City, Japan at a concentration of 0.17 ng/cu m in July, 1991, and 0.12 ng/cu m in April, 1992(1), the slightly higher summer level being attributed to use of pesticides in rice field water(1).|RURAL/REMOTE: Air samples collected over the Mississippi River from New Orleans, LA to St. Paul, MN during the first 10 days in June, 1994 were not found to contain napropamide, detection limit equaling 0.15 ng/cu m, which is used on cropland within 40 km of the river(1).

practically nontoxic

LD50 Rat acute oral >5,000 mg/kg

Napropamide's production and use as a herbicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values for napropamide ranging from 218 to 700(2,3,6) indicate that napropamide is expected to have low to moderate mobility in soil(SRC). Volatilization of napropamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.4X10-10 atm-cu m/mole(SRC), calculated from its vapor pressue, 1.72X10-7(4), and water solubility, 73 mg/l(5). Napropamide is not expected to volatilize from dry soil surfaces(SRC) based upon a its vapor pressure(4). Field studies have shown that the half-life of napropamide ranges from 34 days to over 2 yrs depending on the field conditions, with biodegadation and photolysis as the primary processes(7).|AQUATIC FATE: Based on a classification scheme(1), Koc values for napropamide ranging from 218 to 700(2,3,8) indicate that napropamide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 8.4X10-10 atm-cu m/mole(SRC), calculated from its vapor pressure, 1.72X10-7 mm Hg(4), and water solubility, 73 mg/l(7). According to a classification scheme(5), an estimated BCF of 77(SRC), from an estimated log Kow of 3.36(9) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Direct photolysis in sunlit surface waters may be an important environmental fate process based on a photolysis half-life of 5.7 minutes using a buffered solution in laboratory experiments(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), napropamide, which has a vapor pressure of 1.72X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase napropamide 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 2 hrs(SRC), calculated from its rate constant of 2.3X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase napropamide may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of napropamide with photochemically-produced hydroxyl radicals has been estimated as 2.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Napropamide is resistant to hydrolysis in the environment; more than 97% of the initial 1 mg/kg was recovered after incubation at 20 °C in a sterilized water buffer at pH 7.0 for 3-5 months(3). Napropamide is subject to photodecomposition in soil(4). The first-order half-lives for photodegradation on nine soils incubated at 20 °C varied from 72 to 150 days(5). This rate can be affected by the rate of transport by evaporation of water-soluble napropamide to the sunlight-irradiated zone in soil(6). In aqueous solution at 25 °C buffered at pH 7, the pseudo-first-order photolysis half-life and rate constant were 5.7 minutes and 1.2X10-1/min, respectively, using radiation from a xenon arc lamp(7).

An estimated BCF of 77 was calculated for napropamide(SRC), using a log Kow of 3.36(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, due to rapid aqueous photolysis(4), bioconcentration is not likely to be an important environmental process(SRC).

575.44 L/kg|Koc values for napropamide have been reported to range from 218 to 700(1,2). Kocs for napropamide on several Israeli soils ranged from 249 to 450(3). A Koc of 500 ml/g was calculated from measured Freundlich isotherm parameters in a sorption study using Casa Grande sandy loam from the Maricopa Agricultural Center in central Arizona(4). According to a classification scheme(5), these estimated Koc values suggest that napropamide is expected to have low to moderate mobility in soil.|No observed leaching was noted in field studies using Ockley silt loam nor Bloomsfield loamy sand samples from Lafayette, IN and Johnson, IN, respectively(1). Using the A horizon of 2 Brazilian latosols, napropamide presented high adsorption and low leaching(2). Napropamide did not travel appreciably in 24 hrs from a point source in field studies using Israeli Gilat and Neve Yaar soils(3). Following 2 weeks of leaching with 23 cm net applied water, 73% of the applied napropamide was found in the top 0-19 cm layer in a field study using Tujunga loamy sand in Etiwanda, CA; however, over 1% was found to a depth of 150 cm(4).|Dissolved organic matter has been shown to form a stable complex with this compound(1-3). Napropamide in a 3.5 ml solution with dissolved organic matter at 25 °C for 48 hrs(1) showed a negative linear correlation between the log of the solubility and the log of the association coefficient with dissolved humic acid extracted from Texas peat, fulvic acid obtained from Greenfield sandy loam, Suwannee stream reference fulvic acid, Tujunga loamy sand, and Bermeo clay(1). Using a sludge-amended silt loam soil, it was observed that the water-soluble dissolved organic matter in the soil facilitated napropamide movement, exhibiting a strong positive relationship(4). In laboratory and soil column studies, napropamide was found to bind strongly to dissolved organic matter in sewage sludge and thus migrate through the column(1).

The Henry's Law constant for napropamide is estimated as 8.41X10-10 atm-cu m/mole(SRC) calculated from its vapor pressure, 1.72X10-7 mm Hg(1), and water solubility, 73 mg/l(2). This Henry's Law constant indicates that napropamide is expected to be essentially nonvolatile from water surfaces(3). Napropamide is not expected to volatilize from dry soil surfaces(SRC) based upon it's vapor pressure(1).

GROUNDWATER: Napropamide was not detected in 8 well water samples from 5 counties in a well inventory study in California conducted from July 1, 1994 through June 30, 1995(1).|DRINKING WATER: Napropamide was not detected in finished drinking water in Florence, Italy, using water from the Arno River, surveyed from 1992-1995(1).|SURFACE WATER: Napropamide was not detected in stormwater runoff within the Sacramento River Basin, California during a storm in January 1994(1). Napropamide was not detected in Arno River water samples entering the drinking water treatment plant in Florence, Italy, collected from 1992 through 1995(2). Pesticides adsorbed on soil particulates in runoff can enhance the movement of pesticides from a field(5). In a study conducted from April 1993 through April 1994, napropamide was detected in water samples from two tributary streams of the South Platte River, a small agricultural area in the Lonetree Creek Basin at a median concentration of <0.01 ug/l, but not detected in a small urban area in the Cherry Creek Basin in Colorado(3). Napropamide was not detected in ten water runoff samples from nine golf courses around Singapore(4).

In a 1993-94 US FDA monitoring program of domestic and imported apples and rice, napropamide was detected in 2 of 796 domestic apple samples at a concentration of 0.09 ppm and in 1 of 1062 imported apple samples at a concentration of 0.06 ppm(1).

Occupational exposure to napropamide may occur through inhalation and dermal contact with this compound at workplaces where napropamide is produced or used(SRC). Napropamide was not detected in a year-long conifer nurseryworker pesticide exposure study conducted in March, 1986 using samples from nurseries in Brooklyn, MI, Coeur d'Alene, ID, Elkton, OR, Medford, OR, and Watersmeet, MI(1).

devrinol

(1989) 699,000 lbs active ingredient; (1982) 147,000 lbs active ingredient

USEPA/OPP Pesticide Code 103001; Trade Names: Devrinol; Waylay; R-7165; Napromide; Napropamid; R 7465; R-7475.|Technical grade is 92-96% pure|Emulsifiable concentrate, granules, wettable powder

Product analysis by GLC. Residues in crops and soil determined by GLC. In drinking water by GC with FID.|AOAC Method 991.07. Nitrogen and Phosphorus Containing Pesticides in Finished Drinking Water by Gas Chromatographic Method. Capillary gas chromatography with nitrogen-phosphorus detector.|EMSLC Method 632.1. The Determination of Carbamate and Amide Pesticides in Municipal and Industrial Wastewater by High-Performance Liquid Chromatography. Method detection limit= 0.310 ug/l.|FDA Method 242.2. Method for N-Methylcarbamate Residues. HPLC with fluorescence detector.

Agrochemicals -> Herbicides|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)

Napropamide has known environmental transformation products that include alpha-naphthoxy propionic acid.|Napropamide has known environmental transformation products that include 1-Napthol, DE-NPAM, NOPA, NQ, Napropamide Isomer 2, and Phthalic acid.