Oxyfluorfen

log Kow = 4.73

1.49 g/L

Density: 1.35 at 73 °C

Orange crystalline solid at room temperature

Orange to deep red brown crystalline solid

Readily soluble in most organic solvents, e.g. acetone 72.5, cyclohexanone, isophorone 61.5, dimethylformamide >50, chloroform 50-55, mesityl oxide 40-50 (all in g/100 g, 25 °C)

In water, 1.16X10-1 mg/L at 25 °C

358.2 °C

When heated to decomposition it emits toxic fumes of /hydrogen chloride, hydrogen fluoride, and nitrogen oxides/.

85-90 °C (tech., 65-84 °C)

0.00000025 [mmHg]

2X10-7 mm Hg at 25 °C

Oxyfluorfen is an orange crystalline solid. Non corrosive. Used as an herbicide.

Orange to dark red-brown solid; [HSDB]

2149.1；2166.5

2197；2198；2203.5；2210.4；2203.1；2187.7

172.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID7024241]

175.37 Ų [M]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]；174.76 Ų [M+H]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]

This chemical does not meet GHS hazard criteria for 1% (3 of 309) of reports.

Warning

H400 (98.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410 (98.1%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 309 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 3 of 309 reports by companies.；There are 13 notifications provided by 306 of 309 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard Traits - Environmental tox；Authoritative List - CWA 303(d)；Report - if used as a fragrance or flavor ingredient

Regulation (EC) No 1107/2009 (amended)

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

2008/934/EC, Reg. (EU) 2017/359, Reg. (EU) 2019/291, Reg. (EU) 2024/2781, Reg. (EU) No 798/2011

Oxyfluorfen: HSNO Approval: HSR003418 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

IMAP assessments - Benzene, 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)-: Environment tier I assessment；IMAP assessments - Benzene, 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)-: Human health tier I assessment

Class 9

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, Capacitor, asymmetric, be aware of possible short circuiting as this product is transported in a charged state. Polymeric beads, expandable (UN2211) may evolve flammable vapours. (ERG, 2024)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or asphyxiation. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

The protox inhibitor herbicides (Fomesafen, Oxadiazon, Lactofen, Sulfentrazone, Carfentrazone-ethyl, Oxyfluorofen and Bifenox) can disrupt porphyrin metabolism; It has been speculated that a transient form of porphyria variegate may occur following a massive exposure or long-term exposure to lower doses. A skin and eye irritant; Occasionally irritating to respiratory tract; Toxic to liver in animal studies; [HSDB] May cause irritation; [MSDSonline] See Fluthiacet-methyl.

Ethers；Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic；Fluorinated Organic Compounds；Aryl Halides

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision for Oxyfluorfen p.175. EPA738-R-02-014 (October 2002) When a pesticide is eligible for reregistration, EPA explains the basis for its decision in a Reregistration Eligibility Decision (RED) document.[Available from, as of February 20, 2007: http://www.epa.gov/pesticides/reregistration/status.htm]

Tolerances are established for residues of the herbicide oxyfluorfen [2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene] in or on the following food commodities: [Table#7181]

Tolerances with regional registration are established for residues of the herbicide oxyfluorfen [2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene] in or on the following food commodities: [Table#7182]

A trifluoromethyl diphenyl ether derivative.

Insoluble in water.

Aquatic Acute 1 (98.1%)；Aquatic Chronic 1 (98.1%)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；CAUTION: Fire involving Safety devices (UN3268) and Fire suppressant dispersing devices (UN3559) may have a delayed activation and a risk of hazardous projectiles. Extinguish the fire at a safe distance.；SMALL FIRE: Dry chemical, CO2, water spray or regular foam.；LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.；FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Refer to the "General First Aid" section. (ERG, 2024)

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. For Asbestos, avoid inhalation of dust. Cover spill with plastic sheet or tarp to minimize spreading. Do not clean up or dispose of, except under supervision of a specialist.；SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area.；SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal.；LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2024)

Do not discharge effluent into lakes, streams, ponds, estuaries, oceans, or public 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 sewage treatment plant authority. For guidance, contact your State Water Board or Regional Office of the EPA.

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.

Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

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.

/For/ ... agricultural handlers, EPA has determined that the following mitigation measures are necessary, reasonable, and cost-effective: closed mixing/loading systems to support applications to corn, cotton, soybeans, and aerial applications to fallow land; enclosed cab for applications to corn, and closed cockpit aircraft for applications to fallow land; and double layer PPE for all other mixers, loaders, and applicators.

A 25 ft. vegetative buffer strip must be maintained between all areas treated with this product and lakes, reservoirs, rivers, permanent streams, marshes or natural ponds, estuaries and commercial fish farm ponds. Do not allow spray to drift from the application site and contact people, structures people occupy at any time and the associated property, parks and recreation areas, nontarget crops, aquatic and wetland areas, woodlands, pastures, rangelands, or animals. ... Do not allow people or pets to enter treated area until sprays have dried.

Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet. Users should remove clothing/PPE immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Users should 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.

Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.

Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.；SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Tolerances are established for residues of the herbicide oxyfluorfen [2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene] in or on the following food commodities: [Table#7179]

Tolerances with regional registration are established for residues of the herbicide oxyfluorfen [2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene] in or on the following food commodities: [Table#7180]

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024)

PPE Requirements Established by the RED for liquid products. Mixers, loaders and applicators using engineering controls ... , must wear: Long-sleeved shirt and long pants, shoes plus socks, chemical-resistant gloves when mixing and loading, chemical-resistant apron when mixing and loading. All other mixers, loaders, applicators and other handlers must wear: Coveralls over long-sleeved shirt and long pants, chemical-resistant footwear plus socks, chemical-resistant gloves, chemical-resistant headgear when exposed overhead, chemical-resistant apron when exposed to the concentrate.

PPE Requirements Established by the RED for Granular product formulations. Mixers, loaders, applicators and other handlers must wear: Coveralls over long-sleeved shirt and long pants, chemical-resistant footwear plus socks, chemical-resistant gloves, chemical-resistant apron for mixers and loaders.

Engineering Controls Established by the RED for liquid products. Mixers and loaders supporting aerial applications to fallow land or ground applications to corn, cotton, or soybeans must use a closed system that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides [40 CFR 170.240(d)(4)], and must: -- wear the personal protective equipment required for mixers/loaders using engineering controls, -- wear protective eyewear if the system operates under pressure, and -- be provided and have immediately available for use in an emergency, such as a broken package, spill, or equipment breakdown: coveralls, and chemical-resistant footwear. "Handlers performing applications to corn must use an enclosed cab that meets the definition in the Worker Protection Standard for Agricultural Pesticides [40 CFR 170.240(d)(5)] for dermal protection. In addition, such applicators must: -- wear the personal protective equipment required for applicators using engineering controls, -- be provided and must have immediately available for use in an emergency when they must exit the cab in the treated area: coveralls, chemical-resistant gloves, chemical-resistant footwear, and chemical-resistant headgear, if overhead exposure, -- take off any PPE that was worn in the treated area before reentering the cab, and -- store all such PPE in a chemical-resistant container, such as a plastic bag, to prevent contamination of the inside of the cab". "Pilots must use an enclosed cockpit in a manner that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides [40 CFR 170.240(d)(6)]; When handlers use closed systems or enclosed cabs 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."

Engineering Controls Established by the RED for Granular Formulations. When handlers use closed systems or enclosed cabs 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.

Restricted Entry Intervals (REIs) for Oxyfluorfen: Bulb vegetables 2 days; conifer seedlings 3 days; Conifer trees 6 days; All other crops 24 hours. Scouting is a handler activity under the Worker Protection Standard (WPS), so anyone performing this activity may legally enter the treated field during the REI provided they use the handler personal protective equipment (PPE) specified on the label. In addition, if the scout is a certified crop advisor as defined in the WPS [40 CFR 170.204(b)], the individual can determine the appropriate PPE to be used. For many of these crops, irrigation equipment is not routinely moved by hand. For these methods, the primary activity involves entering the field to turn the watering equipment on and off. This activity is allowed during the REI under the no contact exception to WPS [40 CFR 170.112(b)]. Should irrigation equipment need unexpected repairs during the REI, WPS allows workers to enter a treated field provided early entry PPE is used [40 CFR 170.112(c)]. This exception also usually applies to mechanical harvesting and tree shaking for nut crops in enclosed cabs.

Hepatic

LC50; Species: Anas platyrhynchos (Mallard duck, age 5-7 days) diet >4000 ppm/8 days

LC50; Species: Colinus virginianus (Northern bobwhite, juvenile) diet 390 ppm/8 days

LD50; Species: Colinus virginianus (Northern bobwhite) oral >5000 mg/kg

LC50; Species: Ictalurus punctatus (Channel catfish, juvenile); Conditions: freshwater; flow through; Concentration: 400 ug/L for 96 hr (95% confidence interval: 360-450 ug/L) /74% purity/

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

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8900(SRC), determined from a log Kow of 4.73(2) and a regression-derived equation(3), indicates that oxyfluorfen is expected to be immobile in soil(SRC). Volatilization of oxyfluorfen from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.2X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 2.0X10-7 mm Hg(4), and water solubility, 0.116 mg/L(5). Oxyfluorfen is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). A half-life of 7 days in estuarine sediment(6) indicates that biodegadation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8900(SRC), determined from a log Kow of 4.73(2) and a regression-derived equation(3), indicates that oxyfluorfen is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.2X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 2.0X10-7 mm Hg(4), and water solubility, 0.116 mg/L(5). According to a classification scheme(6), an estimated BCF of 880(SRC), from its log Kow of 4.73(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). A half-life of 7 days in estuarine sediment(8) indicates that biodegadation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), oxyfluorfen, which has a vapor pressure of 2.0X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase oxyfluorfen 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 33 hours(SRC), calculated from its rate constant of 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase oxyfluorfen may be removed from the air by wet or dry deposition(SRC).

Oxyfluorfen was not detected in apples, broccoli, cabbage, carrots, celery, cucumbers, grapefruit, grapes, greens, lemons, lettuce, limes, melons, mushrooms, nectarines, onions, oranges, peppers, plums, potatoes, radishes, squash, turnips(1). Oxyfluorfen was not detected in green beans or sweet potatoes(2). Oxyfluorfen was not detected in peaches, spinach, or strawberries(1-2). Oxyfluorfen was not detected in pears or tomatoes(1-3). Oxyfluorfen was not detected on grapes 4 days after application(4). Oxyfluorfen concentrations of onions were <0.05 mg/kg 4-11 days after applications of 60-240 g/h in test conducted 1985-88(5).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

/AQUATIC SPECIES/ The alterations of the AChE activity in the brains of two fresh water fishes; Oreochromis niloticus and Gambusia affinis were measured after exposure to acute, sub-acute and chronic concentrations from the widely used herbicide; oxyfluorfen. Bioassays were conducted under controlled laboratory conditions. The used concentrations were acute: LC50 for 6 days, sub-acute 1/3 LC50 for 15 days and chronic 1/10 LC50 for 30 days. The obtained results showed marked inhibitory effects of the herbicide on the activity of AChE in both fishes. However, these effects were more pronounced in O. niloticus where the decline in the enzyme activity ranged from 19.7 to 81.28% while in case of G. affinis it ranged from 5.7 to 36.7%. These findings demonstrate that G. affinis is most tolerant to oxyfluorfen toxicity compared with O. niloticus.

/AQUATIC SPECIES/ This paper deals with the expression of the biomarker hsp70 in the liver and kidney of the freshwater fish Oreochromis niloticus following exposure to the herbicide oxyfluorfen (Goal). Fishes were exposed to three concentrations, the 96-hr LC50 (3 mg/L), the 96-hr (1/2) LC50 (1.5 mg/L), and the 96-hr (1/4) LC50 (0.75 mg/L) of oxyfluorfen for 6, 15, and 24 days, respectively, and samples were taken at three different time periods for each concentration. The livers responded to the herbicide by an induction of the expression of both the constitutive (hsp75; Mr 75 kDa) and the inducible (hsp73; Mr 73 kDa) hsp70 proteins. In kidney, the herbicide induced a time-dependent increase in the expression of the constitutive hsp70 (hsp75) as well, but the inducible hsp70 (hsp73) required much longer incubation periods to reach maximal levels (15 and 24 days).

/AQUATIC SPECIES/ The effect of oxyfluorfen was investigated when alga Scenedesmus obliquus has been exposed to different concentrations (7.5, 15, and 22.5 ug/L at 12, 24, and 48 hours of exposure. Toxicity test was done by using 13 biomarkers concerning growth rate, chlorophyll content and indicators of photosynthetic and antioxidant enzyme activities. The change of the 13 parameters showed a great variation of sensitivity indicating differences in parameters' suitability to be used as biomarkers when alga culture was exposed to oxyfluorfen toxicity. The order of sensitivity between those biomarkers was: Antenna size (ABS/RC) > Chlorophyll content > Catalase (CAT) > Operational PSII quantum yield (phiS(PSII)) > Glutathione S-transferase (GST) > Functional plastoquinone pool (Q(PQ)) > Glutathione reductase (GR) > Growth rate > Nonphotochemical quenching (QN) > Proton gradient quenching (Q(Emax)) > Ascorbate peroxidase (APX) > Photochemical quenching (Q(p)) > Maximum PSII quantum yield (Phi(PSII)).

/ACCIDENTAL POISONINGS/ On August 22, 2000, Fifteen Mile Creek near the Dalles Dam in Oregon was the site of an oxyfluorfen spill. A truck carrying formulated oxyfluorfen (Goal 2XL) crashed on a bridge spilling approximately 20,000 gallons of herbicide into the creek yards from where the creek enters the Columbia River. Two weeks after the spill, samples of filtered and unfiltered water near the spill site contained an average of 32 :g/L and 340 :g/L, respectively. This spill was estimated to cause a 35% decrease in the numbers of adult chinook salmon and a 26% decrease in the numbers of steelhead passing over the Dalles Dam the day immediately following the spill, relative to the day prior to the spill. The spill was also reported to kill thousands of young lampreys.

Oxyfluorfen

Hepatic

3 x 10 ^-3 mg/kg-day

The Koc of oxyfluorfen is estimated as 8900(SRC), using a log Kow of 4.73(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that oxyfluorfen is expected to be immobile in soil(SRC). Oxyfluorfen is strongly absorbed to organic soils and only minimally leached(10). Oxyfluorfen had reported Kd values of 52-755 and 111-829 at 25 and 37 °C, respectively in 6 different soils with moisture contents of 30-90%(4). Oxyfluorfen stayed in the top 0-10 cm of soil 28 days after application(5). Oxyfluorfen remained in the top 0-5 cm in a 1992 and 1993 study with an application rate of 1.2 kg ai/ha(6). Oxyfluorfen penetrated to 5.41-8.89 cm with 3.2-12.8 cm of rain and had a half-life in the soil of 35 days(7). Soil half-lives of 30-103 days were calculated for oxyfluorfen at different application rates and rainfall amounts(8). Oxyfluorfen has been noted as persistent and immobile in soil(9).

/CASE REPORTS/ A total of 66 incidents connected with oxyfluorfen were reported in the OPP Incident Data System (IDS) from 1994 to 2000. Most of these incidents involved irritant effects to the eyes, skin and occasionally respiratory passages. There were 25 cases reported in the California Pesticide Illness Surveillance Program and the majority of these cases involved minor symptoms of systemic illness such as headache, dizziness and nausea. During one of these incidents, nine of 15 field workers developed symptoms while transplanting cauliflower plants in a field that was sprayed about 30 minutes earlier. The reentry interval required on the label was 24 hours. These illnesses included symptoms of chemical conjunctivitis, eye irritation, tingling and itching of the skin, nausea, dizziness, headache, and vomiting.

/ALTERNATIVE and IN VITRO TESTS/ ... Human erythroblastic progenitors (BFU-E/CFU-E: Burst Forming Unit-Erythroid and Colony Forming Unit-Erythroid) were exposed to oxyfluorfen, a diphenyl-ether herbicide in the presence of erythropoietin, and the hematoxicity evaluated in vitro by scoring the development of BFU-E/CFU-E colonies after 7 and 14 days of culture. The toxic effect on differentiation has been evaluated using four criteria: morphology, total protein, total porphyrin, and hemoglobin content. The study of BFU-E/CFU-E proliferation and differentiation showed a cytotoxic effect of oxyfluorfen only at very high concentrations. In contrast, hemoglobin synthesis can be inhibited by concentration of oxyfluorfen (10-4 M) that have no adverse effect on cellular proliferation.[Rio B et al; Hum Exp Toxicol 16 (2): 115-22 (1997)]

Oxyfluorfen's production may result in its release to the environment through various waste streams; its use as an herbicide(1) will result in its direct release to the environment(SRC).

AEROBIC: Oxyfluorfen biodegradation rate constant in non-sterile sediment was much greater (p=0.01) than sterile sediment rate constant(1). Biodegradation half-lives were given for oxyfluorfen in non-sterile estuarine sediment as 17 days and non-sterile estuarine water as 27.5 days(2). In a field study, oxyfluorfen had a half-life of 12 days in soil (20.7% sand, 32.8% silt, 46.5% clay, 7.1 pH, 5.84 g/kg organic content) with an application rate of 0.12 kg ai/ha(3).

AEROBIC: Oxyfluorfen was >60% biodegraded in 7 days when incubated at 28 °C using Azotobacter chroococcum, a soil borne bacteria(1).

SEDIMENT: Oxyfluorfen sediment concentrations reached a maximum 3 days after treatment at 0.35 mg/kg in a runoff water containment pond(1).

Hazard Traits - Environmental tox；Authoritative List - CWA 303(d)；Report - if used as a fragrance or flavor ingredient

Regulation (EC) No 1107/2009 (amended)

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

2008/934/EC, Reg. (EU) 2017/359, Reg. (EU) 2019/291, Reg. (EU) 2024/2781, Reg. (EU) No 798/2011

Oxyfluorfen: HSNO Approval: HSR003418 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Tolerances are established for residues of the herbicide oxyfluorfen [2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene] in or on the following food commodities: [Table#7181]

Tolerances with regional registration are established for residues of the herbicide oxyfluorfen [2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene] in or on the following food commodities: [Table#7182]

Diphenylether-type herbicides are extremely potent inhibitors of protoporphyrinogen oxidase, a membrane-bound enzyme involved in the heme and chlorophyll biosynthesis pathways.

The diphenyl-ether herbicides exert their phytotoxic activity /in plants/ by preventing chlorophyll formation ... as a result of inhibition of protoporphyrinogen oxidase. This enzyme is the last step of the common pathway for chlorophyll and heme biosynthesis.

Used as broad spectrum pre- and post-emergence herbicide for tree, fruit, nut, vine, and field crops; Also used for non-agricultural, residential, and forestry applications; [HSDB] Used as food additive; [Hawley]

Farming (Pesticides) [Category: Industry]

For oxyfluorfen (USEPA/OPP Pesticide Code: 111601) 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./

Broad spectrum pre- and post-emergent control of annual broadleaf and grassy weeds in a variety of tree, fruit, nut, vine, and field crops. There are also nonagricultural and forestry uses ... also used for /spot-treatment/ weed control in landscapes, patios, driveways, and similar residential uses.

Herbicide

Based on available pesticide survey usage information for the years 1990 through 1999, an annual estimate of oxyfluorfen's total domestic usage averaged approximately 761,000 pounds a.i. for 1,167,000 acres treated. Use of oxyfluorfen is increasing. From 1992 to 1997 the use of oxyfluorfen increased by 54%, from an estimated 458,000 pounds active ingredient in 1992 to an estimated 705,000 lbs active ingredient in 1997.

Oxyfluorfen is manufactured by reaction of 3,4-dichlorobenzotrifluoride with resorcinol; the resulting product is then treated with ethanol in the presence of potassium hydroxide.

Preparation: NL 7303590; H.O. Bayer et al., US 3798276 (1973, 1974 both to Rohm & Haas)

CHIEF 3SC HERBICIDE Active Ingredient 14.2% Glyphosate, isopropylamine salt, 21.1% Oxyfluorfen

DOUBLE O G-PRO Active Ingredient 1.0% Oryzalin, 2.0% Oxyfluorfen

END ZONE HERBICIDE Active Ingredient 22.2% Oxyfluorfen

GALIGAN 2E Active Ingredient 22.2% oxyfluorfen

For more Formulations/Preparations (Complete) data for OXYFLUOROFEN (23 total), please visit the HSDB record page.

Information on 7 consumer products that contain Oxyfluorfen in the following categories is provided:；• Pesticides

Pharmaceuticals

The WHO Recommended Classification of Pesticides by Hazard identifies Oxyfluorfen (technical grade) as unlikely to present an acute hazard in normal use; Main Use: herbicide.

Oxyfluorfen is a diphenyl ether herbicide structurally related to lactofen, fomesafen and acifluorfen. ... Mode of Action: Oxyfluorfen targets a specific enzyme, protoporphyrinogen oxidase, in the chlorophyll biosynthetic pathway. Inhibiting protoporphyringen oxidase in plants leads to an accumulation of phototoxic chlorophyll precursors which, in the presence of light, produce activated oxygen species which rapidly disrupt cell membrane integrity. Oxyfluorfen must contact plant foliage to cause effects. Plants that are actively growing are most susceptible to oxyfluorfen. By forming a chemical barrier on the soil surface, oxyfluorfen affects plants at emergence. ... Because of the length of oxyfluorfen soil half-life, this barrier may last up to three months.

Oxyfluorfen is formulated for agricultural uses as an emulsifiable liquid concentrate containing 0.2 to 4 pounds active ingredient (ai) per gallon and as a granular product containing 2% oxyfluorfen by weight. Oxyfluorfen is most frequently used in a liquid formulation for food crops and as a granular formulation for ornamental nursery crops. There are also several ready-to-use products and a liquid concentrate available for residential use. Residential formulations contain 0.25% to 0.70% oxyfluorfen by volume and are packaged in a ready-to-use (RTU) sprinkler jug, a RTU trigger sprayer or as a liquid to be mixed in a sprinkler can or tank sprayer. Agricultural liquid formulations of oxyfluorfen are applied using large, small or ATV groundboom rigs. Aerial application is used mainly for fallow fields and bulb vegetables. Backpack sprayers can be used in Christmas tree plantations and right-of-way areas. Chemigation is used for over the top application to bulb vegetables and for drip application to some orchard trees, however, chemigation is often prohibited per the product labels. Right-of-way sprayers are used in right-of-way areas. Granular oxyfluorfen is applied to field- and container-grown ornamentals with broadcast spreaders

Oxyfluorfen was first registered in the United States in 1979 ... Based on current use patterns, handlers (mixers, loaders, and applicators) may be exposed to oxyfluorfen during and after normal use of liquid and granular formulations in agricultural and other settings. Oxyfluorfen is used in the residential environment by homeowners to kill weeds on patios, driveways and similar surfaces. Oxyfluorfen homeowner products are intended solely for spot treatment; they are not used for broadcast treatment of lawns because they kill grass.