Ethalfluralin

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Nitroaromatic

Pesticide (Ethalfluralin) -> USDA PDB

Pesticide

log Kow = 5.11

5.11

In acetone, acetonitrile, benzene, chloroform, dichloromethane, xylene >500, methanol 82-100 (all in g/L, 25 °C)

In water, 0.3 mg/L at 25 °C

0.0000878 [mmHg]

8.8X10-5 mm Hg at 25 °C

Warning

H315 (53.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 104 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

2008/934

Increased frequency of hepatocellular hyperplasia observed in 2-year feeding study of mice; Hemolytic anemia in 1-year feeding study of dogs; Developmental NOAEL much higher than maternal NOAEL in rats and rabbits; [HSDB] Irritating to skin and eyes of rabbits; May cause skin sensitization; Acute target organs are the liver, kidney, thyroid, and blood; Mutagenic effects with metabolic activation in vitro; Limited evidence of a carcinogenic effect. Mild reversible effects including lachrymation, burning sensation in the eyes, and headaches have been reported by workers in production facilities; [EFSA] A case of facial dermatitis following accidental direct exposure was reported in the California handler database; [Krieger, p. 770] In guinea pig skin sensitization studies, the modified Buehler method showed no sensitization, but the Magnusson and Kligman test was positive; Increased enzyme activity (SGPT and alkaline phosphatase) and increased liver weights observed in 3-month feeding study of mice; No systemic toxicity in dermal study of rabbits; Weakly or not mutagenic; Possible human carcinogen based on animal studies; [Reference #1]

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Ethafluralin EPA-738-R-95-001 (March 1995). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of June 14, 2007: http://www.epa.gov/pesticides/reregistration/status.htm]

Tolerances are established for residues of the herbicide ethalfluralin [N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-(trifluoromethyl)benzenamine] in or on the following raw agricultural commodities: [Table#7253]

Based on the reviews of the generic data for the active ingredients ethalfluralin, the Agency has sufficient information on the health effects of ethalfluralin and on its potential for causing adverse effects in fish and wildlife and the environment. Therefore, the Agency concludes that products containing ethalfluralin for all uses with the exception of the postemergence and posttransplant uses on cucurbits are eligible for reregistration. The Agency has determined that ethalfluralin products, labeled and used as specified in this Reregistration Eligibility Decision document, will not pose unreasonable risks or adverse effects to humans or the environment.

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. Ethalfluralin is found on List B. Case No: 2260; Pesticide type: Herbicide; Case Status: RED Approved (12/94, PB95-262101) - OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document; Active ingredient (AI): N-Ethyl-N(2-methyl-2-propenyl)-2,6-dinitor-4-(trifluoromethyl)benzemine; Data Call-in (DCI) Date(s): 12/31/90, 08/23/95; AI Status: RED Completed - OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Do not contaminate water, food or feed by storage ... Store in a cool, dry place. Store in original container. In case of leak or spill, contain material and dispose as waste. /Technical ethafluralin/

Store in container at >5 °C. Avoid freezing, poor weed control may result. Do not store near heat or open flame.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Pesticide Disposal: Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. Metal Drum Disposal: Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, or by other procedures approved by state and local authorities. Fiber Drum Disposal: Completely empty fiber drum by shaking and tapping sides and bottom to loosen clinging particles. Empty residue into manufacturing equipment Crush or puncture and dispose of in a sanitary landfill or by incineration if allowed by state and local authorities. /Technical ethafluralin/

This product is toxic to fish and aquatic invertebrates. Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance contact your State Water Board or Regional Office of the EPA. /Technical ethafluralin/

For several good reasons, all of the herbicides mentioned in this chapter /including ethafluralin/ should be handled and applied only with full attention to safety measures that minimize personal contact. Many formulations contain adjuvants (stabilizers, penetrants, surfactants) that may have significant irritating and toxic effects. A number of premixed formulations contain two or more active ingredients; the companion pesticides may be more toxic than the principal herbicide. Good hygienic practice should not be disregarded just because a pesticide is reported to have a high LD50 in laboratory rodents.

Wash thoroughly with soap and water after handling. Remove contaminated clothing and wash clothing before reuse. This material will cause intense staining. /Technical ethafluralin/

Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them. Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Sonalan HFP/

User Safety Recommendations. Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Sonalan HFP/

For more Preventive Measures (Complete) data for ETHALFLURALIN (7 total), please visit the HSDB record page.

/Agricultural Use/ Applicators and other handlers must wear: Coveralls worn over long-sleeved shirt and long pants; Chemical-resistant gloves such as Barrier Laminate or Viton; Chemical-resistant footwear plus socks; Protective eyewear; Chemical-resistant headgear for overhead exposure; Chemical-resistant apron when cleaning equipment, mixing, or loading /Sonalan HFP/

/Agricultural Use/ Engineering Controls: When handlers use closed systems, enclosed cabs, or aircraft in a manner that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides, 40 CFR 170.240(d)(4-6), the handler PPE requirements may be reduced or modified as specified in the WPS. /Sonalan HFP/

Agricultural Use Requirements. Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. ... The requirements in this /entry/ only apply to uses of this product that are covered by the Worker Protection Standard. Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 24 hours. Exception: If the product is soil-injected or soil-incorporated, the Worker Protection Standard, under certain circumstances, allows workers to enter the treated area if there will be no contact with anything that has been treated. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, is: Coveralls over short-sleeved shirt and short pants Chemical-resistant gloves such as Barrier Laminate or Viton Chemical-resistant footwear plus socks Protective eyewear Chemical-resistant headgear for overhead exposure. /Sonalan HFP/

Wear protective eyewear (goggles or face shield) and protective clothing such as coveralls, a long- sleeved shirt and Impermeable gloves when handling this product. /Technical ethafluralin/

Chemical-resistant gloves. Coveralls over long sleeved shirt and long pants.

LC50; Species: Anas platyrhynchos (Mallard duck, age 10 days) dietary >5000 ppm for 8 days

LC50; Species: Colinus virginianus (Northern bobwhite) dietary >5000 ppm for 8 days

LD50; Species: Colinus virginianus (Northern bobwhite, age 15 months) oral >2000 mg/kg for 14 days

LD50; Species: Apis mellifera (Honey bee, worker) topical 51 ug/bee for 48 hr

For more Ecotoxicity Values (Complete) data for ETHALFLURALIN (15 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 4100-8400 measured in 4 soils(2), indicate that ethalfluralin is expected to have slight to no mobility in soil(SRC). Volatilization of ethalfluralin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 8.8X10-5 mm Hg(3) and water solubility of 0.3 mg/L(3); however, adsorption may attenuate this process(SRC). Volatilization from dry soil surfaces is not expected(SRC) based on the vapor pressure of this compound(3). The volatility of ethalfluralin was studied following the unincorporated surface application (1.1 kg/ha applied in late May) of the granular formulation to a field (69% clay, 19% silt, 12% sand) located in Canada(4). Approximately 14% volatilization was observed over the course of a 24 day study period(4). Volatility losses were associated with rainfall events, and little volatilization was observed when the soil was dry. Ethalfluralin applied to a sandy loam soil at 3 mg/kg had a half-life of 46 days under aerobic conditions and 13.8 days under anaerobic conditions(5). The photodegradation half-life of ethalfluralin applied to a sandy loam soil was 14.23 days(5).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 4100-8400 measured in soil(2), indicate that ethalfluralin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 8.8X10-5 mm Hg(4) and water solubility of 0.3 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 10 hours and 11 days, respectively; however, adsorption may attenuate volatilization(SRC). The volatilization half-life from a model pond was estimated as 137 days when adsorption was considered(5). According to a classification scheme(6), a whole-body BCF value of 1180 measured in rainbow trout(7), suggests bioconcentration in aquatic organisms is very high(SRC). Ethalfluralin in pH 5 buffer solution had a photodegradation half-life of 6.3 hours(7). Ethalfluralin applied at a concentration of 0.166 mg/L degraded with a half-life of approximately 2 days in an outdoor pond(8). The anaerobic aquatic degradation half-life of ethalfluralin applied (0.12 mg/kg) to a sediment/water system obtained from a Mississippi pond was approximately 38 hours(2,7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethalfluralin, which has a vapor pressure of 8.8X10-5 mm Hg at 25 °C(1) is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase ethalfluralin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC). The half-life for this reaction in air is estimated to be 6 hours for hydroxyl radicals and 23 hours for ozone(SRC), calculated from their respective rate constants of 6.9X10-11 cu cm/molecule-sec and 1.2X10-17 cu cm/molecule-sec at and 25 °C(SRC) that were derived using a structure estimation method(3). Particulate-phase ethalfluralin may be removed from the air by wet or dry deposition(SRC). Ethalfluralin at a concentration of 9.8 ug/cu m was degraded quickly in a laboratory chamber upon exposure to simulated summer sunlight at 34 °C, with a calculated half-life of about 2 hours(4).

/BIRDS and MAMMALS/ Technical ethalfluralin (94.5%) is considered to be practically nontoxic to bobwhite quail with an acute oral LD50 greater than 2,000 ppm. On a subacute dietary basis, ethalfluralin (94.5%) is considered to be practically nontoxic to bobwhite quail and mallard ducks with dietary LC 's of greater than 5,000 ppm. In two avian reproduction studies, there were no adverse effects at 1,000 ppm, the highest dietary intake tested, from ethalfluralin (93.5%) in the bobwhite quail or the mallard duck. A Lowest Observed Effect Level (LOEL) could not be determined.

/AQUATIC SPECIES/ The formulated product of ethalfluralin (36.5%) is considered to be highly toxic to bluegill sunfish with a product LC50 of 210 ppb. An acute toxicity sediment study was submitted, because ethalfluralin persists in soils and is very highly toxic to fish. Ethalfluralin (29.9%) was mixed in soil at 1, 10, and 100 ppm; 15-g and 50-g soil samples from each concentration were added to separate 15-L water chambers in which 20 bluegill sunfish (2 replicates of 10 fish each) were exposed. Fifteen grams of soil in 15 liters of water was used to represent an amount that could conceivably erode from a treated field; 50 g in 15 l of water provided a limit of turbidity that still permitted observations of the test fish. The concentration of ethalfluralin in the water was measured when fish were added to the chambers and after 96 hours. ... These data indicate that ethalfluralin released from soil sediments can be lethal to sunfish (0-55% mortality) when concentrations in the aqueous phase reach approximately between 17 and 58 ppb. A Fish Early Life Cyle Toxicity /test was conducted in Rainbow trout using 95.6% a.i./ The NOEL = 0.4 ug/L, the LOEL = 1.4ug/L, and the Maximum Allowable Toxic Concentration = 0.7 ug/L. The most sensitive parameters affected in trout were larval length and weight.

/AQUATIC SPECIES/ Technical ethalfluralin (94%) is considered to be very highly toxic to Daphnia magna with an EC of 60 ppb. The formulated product with ethalfluralin (36.5%) is considered to be slightly toxic to Daphnia magna with a product EC of 18.1 ppm. In a chronic toxicity study of Daphnids reproduction was the most sensitive parameter affected.

/AQUATIC SPECIES/ Acute toxicity testing with marine/estuarine organisms is required for ethalfluralin because of the soybean use pattern. The acute toxicity studies for marine/estuarine organisms are summarized /as follows/: Sheeps-head, technical product with 95.46 a.i, LC50 = 240 ppb. Highly toxic. Eastern oyster, technical products with 95.46 and 95.93% a.i., LC50 100 and 170 ppb, respectively. Highly toxic. Mysid shrimp, technical product with 95.46% a.i., LC50 230 ppb. Highly toxic.

For more Ecotoxicity Excerpts (Complete) data for ETHALFLURALIN (7 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Corrosive: causes skin burns and irreversible eye damage. Harmful if swallowed or inhaled. Prolonged or frequently repeated skin contact may cause allergic reactions In some individuals /Sonalan HFP/

/SIGNS AND SYMPTOMS/ Causes substantial but temporaiy eye irritation and skin irritation. Harmful if inhaled. Prolonged or frequently repeated skin contact may cause allergic reactions In some individuals. /Technical ethalfuralin/

Ethalfluralin's production may result in its release to the environment through various waste streams; it's use as a selective herbicide for the preemergence control of annual grasses and broadleaf weeds(1) will result in its direct release to the environment(SRC).

AEROBIC: Ethalfluralin applied to a sandy loam soil at 3 mg/kg had a half-life of 46 days under aerobic conditions(1). The concentration of ethalfluralin decreased from 84.4% immediately posttreatment, to 49% at 0.9 months and finally to 1.3% of the applied amount at 9 months post application(1). Ethalfluralin applied at a concentration of 0.166 mg/L degraded with a half-life of approximately 2 days in an outdoor pond(2). Ethalfluralin applied to a bare ground uncropped silty clay field in Illinois, dissipated with a half-life of 23 days(1). Ethalfluralin applied to an uncropped sandy loam field in Georgia, dissipated with a field half-life of 28 days(1).

ANAEROBIC: Ethalfluralin applied to a sandy loam soil at 3 mg/kg had a half-life of 13.8 days under anaerobic conditions(1). The anaerobic aquatic degradation half-life of ethalfluralin applied (0.12 mg/kg) to a sediment/water system obtained from a Mississippi pond was approximately 38 hours(1,2).

Tolerances are established for residues of the herbicide ethalfluralin [N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-(trifluoromethyl)benzenamine] in or on the following raw agricultural commodities: [Table#7253]

Based on the reviews of the generic data for the active ingredients ethalfluralin, the Agency has sufficient information on the health effects of ethalfluralin and on its potential for causing adverse effects in fish and wildlife and the environment. Therefore, the Agency concludes that products containing ethalfluralin for all uses with the exception of the postemergence and posttransplant uses on cucurbits are eligible for reregistration. The Agency has determined that ethalfluralin products, labeled and used as specified in this Reregistration Eligibility Decision document, will not pose unreasonable risks or adverse effects to humans or the environment.

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. Ethalfluralin is found on List B. Case No: 2260; Pesticide type: Herbicide; Case Status: RED Approved (12/94, PB95-262101) - OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document; Active ingredient (AI): N-Ethyl-N(2-methyl-2-propenyl)-2,6-dinitor-4-(trifluoromethyl)benzemine; Data Call-in (DCI) Date(s): 12/31/90, 08/23/95; AI Status: RED Completed - OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

In the ruminant metabolism study, a lactating dairy cow was dosed with uniformly ring-labeled [14C]ethalfluralin at 10 ppm in the diet (about 14 200x the maximum theoretical dietary burden) for three consecutive days. The total radioactive residues were 0.011 ppm in fat, 0.050 ppm in kidney, 0.104 ppm in liver, 0.002 ppm in muscle, and up to 0.006 ppm in milk. Ethalfluralin was identified in milk and fat; neither parent nor metabolites were identified in kidney or liver.

In the poultry metabolism study, laying hens were dosed with uniformly ring-labeled [14C]ethalfluralin at 10 ppm in the diet (about 200x the 14 maximum theoretical dietary burden) for ten consecutive days. The maximum total radioactive residues were 0.169 ppm in eggs, 0.697 ppm in liver, 0.070 ppm in muscle, and 0.194 ppm in skin. The parent compound, ethalfluralin, was the major compound identified in skin, but was a minor component in eggs, liver, and muscle. Four other metabolites, 2,6-dinitro-4-(trifluoromethyl)phenol, N-ethyl-2,6-dinitro-4- (trifluoromethyl)benzenamine, N-(2-methyl-2-propenyl)-2,6-dinitro-4- (trifluoromethyl)benzenamine, and 2,6-dinitro-4- (trifluoromethyl)benzenamine, were identified; each identified metabolite was present at >/=0.05 ppm.

In the poultry metabolism study, laying hens were dosed with uniformly ring-labeled [14C]ethalfluralin at 10 ppm in the diet (about 200x the 14 maximum theoretical dietary burden) for ten consecutive days. The maximum total radioactive residues were 0.169 ppm in eggs, 0.697 ppm in liver, 0.070 ppm in muscle, and 0.194 ppm in skin. The parent compound, ethalfluralin, was the major compound identified in skin, but was a minor component in eggs, liver, and muscle. Four other metabolites, 2,6-dinitro-4-(trifluoromethyl)phenol, N-ethyl-2,6-dinitro-4- (trifluoromethyl)benzenamine, N-(2-methyl-2-propenyl)-2,6-dinitro-4- (trifluoromethyl)benzenamine, and 2,6-dinitro-4- (trifluoromethyl)benzenamine, were identified; each identified metabolite was present at >/=0.05 ppm.

A study with Rhesus monkeys indicated that 2.8% of a dermal dose was absorbed through the skin.

Fischer 344 rats were treated orally with a single low dose, a single high dose, or repeated low doses of radiolabeled ethalfluralin. Absorption of ethalfluralin was estimated at 79-87% of the dose for all dose levels. Ethalfluralin was rapidly and extensively metabolized, and 95% of the chemical was excreted in urine and feces by seven days. The major route of elimination for the radiolabel was in the feces, 50.9-63.2%, and the levels remaining in the tissues after 72 hours were negligible. ...

Used as selective pre-emergence herbicide for various grain, seed, and cucurbit crops; Primarily used on soybeans, dry beans, and sunflower seeds; [Reference #1]

Farming (Pesticides) [Category: Industry]

For ethalfluralin (USEPA/OPP Pesticide Code: 113101) 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./

Herbicide

For formulation into an end-use herbicide only for use on the following crops: dry beans, dry peas, cucurbits, peanuts, soybeans and sunflowers. /Technical ethafluralin/

Ethafluralin is used on beans, watermelons, sunflowers, cantaloupes, and cucumbers.

The annual use of ethalfluralin from 1989-1991 was 2300-4200 lbs a.i.

Based on figures reported between 1989 and 1993, EPA estimated that annual U.S. Usage of ethalfluralin was 3,07305,667 acres treated with 2,300-4,200 lb of active ingredient.

Ethalfluralin is produced by reaction of 2,6-dinitro-4-trifluoromethylchlorobenzene with N-ethylmethylallylamine.

Prepn: H.D. Porter, DE 2511897; idem, GB 1505249 (1975, 1978 both to Eli Lilly).

ETHALFLURALIN TECHNICAL Active Ingredient 96.0% ethalfluralin; SONALAN 10G Active Ingredient 10.0% ethalfluralin; SONALAN HFP Active Ingredient 31.5% ethalfluralin

CLEAN CROP CURBIT EC HERBICIDE Active Ingredient 31.5% Ethalfluralin; STRATEGY Active Ingredients 18.2% Ethalfluralin and 5.60% Clomazone

The ethalfluralin formulations registered for use on crops include the granular (G), the dry flowable (DF), and the emulsifiable concentrate (EC). These formulations may be applied preplant, postplant prior to emergence, postemergence, or post-transplant as a soil incorporated, band, or broadcast application using ground equipment.

Two technical grade products are currently available: Registration numbers 62719-132; 68156-2