Napropamid

Pesticide -> EPA IRIS

Herbicides

Active substance -> EU Pesticides database: Approved

Pesticides -> Herbicides, Other

Herbicides

Environmental transformation -> Pesticides (parent, predecessor)

log Kow= 3.36

3.3

Colorless crystals; (tech., brown solid)

Brown solid

Light brown solid from n-pentane.

White crystals when pure

/Solubility/ in acetone, ethanol >1000, xylene 505, kerosene 62, hexane 15 (all in g/l, 20 °C); miscible with acetone, ethanol, methyl isobutyl ketone.

Acetone: >100; ethanol: >100; n-hexane: 1.5; 4-methylpentan-2- one: soluble; kerossene: 6.2; xylene: 50.5 g/100 ml @ 20 °C

In water, 73 mg/l @ 20 °C

75 °C

Melting point: 74.8-75.5 °C when pure (technical is 68-70 °C)

0.00000017 [mmHg]

1.72X10-7 mm Hg @ 25 °C

This chemical does not meet GHS hazard criteria for 9.5% (4 of 42) of reports.

Warning

H319 (83.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Commission Regulation (EC) No 1490/2002

Napropamide is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2010/83/EU, Reg. (EU) 2018/670, Reg. (EU) 2023/2592, Reg. (EU) No 540/2011

Propanamide, N,N-diethyl-2-(1-naphthalenyloxy)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Napropamide is found on List B. Case No: 2450; Pesticide type: herbicide; Case Status: PreRED - OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): n,n-diethyl-2-(1-naphthalenyloxy)propionamide; Data Call-in (DCI) Date(s): 2/13/1991, 2/28/1994, and 10/13/1995; AI Status: Supported - The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Tolerances are established for negligible residues (N) of the herbicide N,N-Diethyl-2-(1-napthalenyloxy)propionamide in or on the following raw agricultural commodities: almond, hulls; artichokes; asparagus; avocados; basil; brassica (cole) leafy vegetables; coffee beans; cucurbits vegetables; figs; fruits, citrus; fruits, pome; fruits, small; fruits, stone; kiwifruit; marjoram; mint; nuts; olives; persimmons; pistachio nuts; rhubarb; rosemary; savory, summer; savory, winter; sweet potato, and vegetables, fruiting.

Tolerances with regional registration are established for residues of the herbicide N,N-Diethyl-2-(1-napthalenyloxy)propionamide in or on the following raw agricultural commodities: pomegranates.

(FL) FLORIDA 700 ug/l

(ME) MAINE 840 ug/L

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.

Tolerances are established for negligible residues (N) of the herbicide N,N-Diethyl-2-(1-napthalenyloxy)propionamide in or on the following raw agricultural commodities: almond, hulls, 0.1(N) ppm; artichokes, 0.1 ppm; asparagus, 0.1 ppm; avocados, 0.1 ppm; basil, 0.1 ppm; brassica (cole) leafy vegetables, 0.1 ppm; coffee beans, 0.1(N) ppm; cucurbits vegetables, 0.1 ppm; figs, 0.1(N) ppm; fruits, citrus, 0.1(N) ppm; fruits, pome, 0.1(N) ppm; fruits, small, 0.1(N) ppm; fruits, stone, 0.1(N) ppm; kiwifruit, 0.1 ppm; marjoram, 0.1 ppm; mint, 0.1 ppm; nuts, 0.1(N) ppm; olives, 0.1 ppm; persimmons, 0.1 ppm; pistachio nuts, 0.1 ppm; rhubarb, 0.1 ppm; rosemary, 0.1 ppm; savory, summer, 0.1 ppm; savory, winter, 0.1 ppm; sweet potato, 0.1 ppm and vegetables, fruiting, 0.1(N) ppm.

Tolerances with regional registration are established for residues of the herbicide N,N-Diethyl-2-(1-napthalenyloxy)propionamide in or on the following raw agricultural commodities: pomegranates, 0.1 ppm.

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).

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).

Napropamide

Reproductive

1 x 10 ^-1 mg/kg-day

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).

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).

AEROBIC: Napropamide degradation may be dependent on concentration(1). Following acclimation at 25 °C, napropamide half-lives in soil were observed to range from 34 to 217 days at 4 ug/g and from 156 to 436 days at 16 ug/g in Gilat soil; half-lives ranged from 108 to 507 days at 4 ug/g and 150-923 days at 16 ug/g in Neve Yaar soil, both samples from Israel(1). The rate generally decreased as soil moisture content decreased(1). Similar results were obtained using soil samples from Great Britain(2). These results indicate that this compound biodegrades slowly(1). These rates were positively correlated with the extent of napropamide adsorption and soil clay content and negatively correlated with soil pH(3). Napropamide applied at 1.12 and 2.24 kg/ha in the spring adversely affected fall growth of rye, the latter by 84%, in a field study using sandy loam soil, indicating slow degradation in the environment(4). 50% loss times of 25, 45, and 75 days at 25, 15, and 5 °C were noted in soil; when treated a second time, 50% loss times decreased to 4, 7, and 15 days at the same temperatures, irrespective of the temperature of the first incubation(5).

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).

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).

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Napropamide is found on List B. Case No: 2450; Pesticide type: herbicide; Case Status: PreRED - OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): n,n-diethyl-2-(1-naphthalenyloxy)propionamide; Data Call-in (DCI) Date(s): 2/13/1991, 2/28/1994, and 10/13/1995; AI Status: Supported - The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Tolerances are established for negligible residues (N) of the herbicide N,N-Diethyl-2-(1-napthalenyloxy)propionamide in or on the following raw agricultural commodities: almond, hulls; artichokes; asparagus; avocados; basil; brassica (cole) leafy vegetables; coffee beans; cucurbits vegetables; figs; fruits, citrus; fruits, pome; fruits, small; fruits, stone; kiwifruit; marjoram; mint; nuts; olives; persimmons; pistachio nuts; rhubarb; rosemary; savory, summer; savory, winter; sweet potato, and vegetables, fruiting.

Tolerances with regional registration are established for residues of the herbicide N,N-Diethyl-2-(1-napthalenyloxy)propionamide in or on the following raw agricultural commodities: pomegranates.

(FL) FLORIDA 700 ug/l

(ME) MAINE 840 ug/L

Used as herbicide; [Merck Index]

Farming (Pesticides) [Category: Industry]

For napropamide (USEPA/OPP Pesticide Code: 103001) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Selective herbicide

This is a man-made compound that is used as a pesticide.

Prepn: H. Files et al., U.S. pat 3,480,671 (1969 to Stauffer).

/Napropamide/ ... is obtained by the reaction of 1-naphthol and N,N-diethyl-alpha-bromopropionamide in MeOH-NaOMe at reflux.

alpha-naphthol + alpha-chloropropionic acid + diethylamine (ether formation/amide formation)

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

Herbicides

Environmental transformation -> Pesticides (parent, predecessor)