Lactofen

461.77

461.77

616-466-9

3077

DTXSID7024160

Dark brown to tan

2918990025

108

4.81

Technical lactofen is a white crystalline solid (205), although it may appear brown or tan in formulation (223, 1).

1.391 at 25 deg C

44-46 deg C

494.0±45.0 °C at 760 mmHg

252.6±28.7 °C

1.535

In water, 0.1 mg/L at 25 deg C

0-6°C

7X10-8 mm Hg at 25 deg C

Oral-Rat LD50: 5000 mg/kg

Flammable; burning produces toxic nitrogen oxide, fluoride and chloride gases

Henry's Law constant = 4.24X10-7 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 3.2X10-12 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

LACTOFEN is a diphenyl ether derivative.

UN30779/PG3

2

21-51/53

36/37-61

DG5643120

Xn,N

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

P273-P280

H312-H411

Do not contaminate water, food or feed by disposal or cleaning of equipment. Open dumping is prohibited. ... If these wastes cannot be disposed of by use according to label instructions, contact your State Pesticide or ENvironmental COntrol Agency, or the Hazardous Waste representative at the nearest EPA Regional Office for guidance.|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 Elinination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containigng 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.|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.

USEPA/Office of Pesticide Programs; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Lactofen EPA 738-R-04-002 (September 2003). EPA issues a TRED for a pesticide that requires tolerance reassessment decisions, but does not require a reregistration eligibility decision at present because: the pesticide was initially registered after November 1, 1984, and by law is not included within the scope of the reregistration program; EPA completed a RED for the pesticide before FQPA was enacted on August 3, 1996; or the pesticide is not registered for use in the U.S. but tolerances are established that allow crops treated with the pesticide to be imported from other countries.[Available from, as of February 28, 2007: http://www.epa.gov/pesticides/reregistration/status.htm]|EPA/Prevention, Pesticides and Toxic Substances; Lactofen TRED Facts. 4 p. EPA 738-F-04-002 (September 2003). Available at http://www.epa.gov/oppsrrd1/REDs/factsheets/lactofen_tred_fs.pdf as of February 22, 2007

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, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H302 (47.22%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P312, P322, P330, P363, P391, and P501|Aggregated GHS information provided by 72 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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. Move containers from fire area if you can do it without risk. Dike fire-control water 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 engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an 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, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck 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, 2016)

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. Avoid inhalation of asbestos dust. 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, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Avoid contact with eyes, skin or clothing. Avoid breathing vapor or spray mist. Wash thoroughly with soap and water after handling. Wear long sleeved shirt and long pants, socks, shoes, and chemical resistant (such as nitrile or butyl) gloves when handling. Remove contaminated clothing and wash before reuse. /Lactofen technical/|First Aid: If in eyes: hold eye open and rinse slowly and gently with water for 15-20 minutes. Remove contact lenses, if present, after the first 5 minutes, then continue rinsing eye. Call a poison control center or doctor for treatment advice. If on skin or clothing: Take off contaminated clothing. Rinse skin immediately with plenty of water for 15-20 minutes. Call a poison control center or doctor for treatment advice. If swallowed: Call poison control center or doctor immediately for treatment advice. Have person sip a glass of water if able to swallow. Do not induce vomiting unless told to do so by the poison control center or doctor. Do not give anything by mouth to an unconscious person. If inhaled: Move person to fresh air. If person is not breathing, call 911 or an ambulance, then give artificial respiration ... Call a poison control center or doctor for treatment advice. /Lactofen technical/

... Causes mild skin irritation ... The manufacturing use product is a moderate eye irritant.

practically nontoxic

LD50 Rat oral >5000 mg/kg|LD50 Rat percutaneous 2000 mg/kg

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

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 10,000(2), indicates that lactofen is expected to be immobile in soil(SRC). Volatilization of lactofen from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.2X10-7 atm-cu m/mole(SRC), calculated from its vapor pressure of 7X10-8 mm Hg(3) and water solubility of 0.1 mg/L(2). Lactofen is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. The field half-life of lactofen in soil was reported as 3 days(5). Others have reported the half-life of lactofen in soil to range from 1-7 days(6).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 10,000(2), indicates that lactofen 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 4.2X10-7 atm-cu m/mole(SRC), calculated from its vapor pressure of 7X10-8 mm Hg(4) and water solubility of 0.1 mg/L(2). According to a classification scheme(5), a whole body BCF value of 380 measured in fish(6), suggest bioconcentration in aquatic organism is high(SRC). A base-catalyzed second-order hydrolysis rate constant of 0.21 L/mole-sec(SRC) was estimated using a structure estimation method(7); this corresponds to half-lives of 1 year and 37 days at pH values of 7 and 8, respectively(7). No biodegradation data were located for lactofen in water; however, this compound readily biodegrades in soil with reported half-lives of 1-7 days(8), which suggests that biodegradation in water will also occur(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), lactofen, which has a vapor pressure of7X10-8 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase lactofen 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 5 days(SRC), calculated from its rate constant of 3.2X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Lactofen absorbs light in the environmental UV spectrum and may undergo photolysis; the photodegradation half-life of lactofen was reported as 24 days(4).

The rate constant for the vapor-phase reaction of lactofen with photochemically-produced hydroxyl radicals has been estimated as 3.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.21 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 1 year and 37 days at pH values of 7 and 8, respectively(2). Lactofen absorbs light in the environmental UV spectrum and may undergo photolysis, but the rate of this reaction is slow compared to biotic degradation(3,4). The photodegradation half-life of lactofen was reported as 24 days(5).

The BCF value of lactofen was 52, 380, and 830 in the edible, whole body, and viscera of bluegills exposed to 0.01 mg/L of lactofen in a flow through aquarium over the course of a 14 day exposure period(1). According to a classification scheme(2), these BCF data suggest bioconcentration in aquatic organisms is high(SRC).

1.00e+04 L/kg|The Koc of lactofen is 10,000(1). According to a classification scheme(2), this estimated Koc value suggests that lactofen is expected to be immobile in soil(SRC).

The Henry's Law constant for lactofen is estimated as 4.2X10-7 atm-cu m/mole(SRC) from its vapor pressure of 7X10-8 mm Hg at 20 °C(1) and water solubility of 0.1 mg/L(2). This Henry's Law constant indicates that lactofen is expected to be essentially nonvolatile from water surfaces(3). Lactofen is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to lactofen may occur through inhalation and dermal contact with this compound at workplaces where lactofen is produced or used. (SRC)

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

Lactofen belongs to the diphenylether class of herbicides, which targets protoporphyrinogen oxidase, which in turn causes singlet oxygen generation. In tolerant plants like soybean (Glycine max), the chemical nonetheless causes necrotic patches called "bronzing" in contact areas. Here it is shown that such bronzing is accompanied by cell death, which was quantified from digital microscopic images using Assess Software. Cellular autofluorescence accompanied cell death, and a homolog of the cell death marker gene, Hsr203j, was induced by lactofen in treated soybean tissues. Thus, this form of chemically induced cell death shares some hallmarks of certain types of programmed cell death. In addition to the cell death phenotype, lactofen caused enhanced expressions of chalcone synthase and chalcone reductase genes, mainly in the exposed and immediately adjacent (proximal) cells. Furthermore, isoflavone synthase genes, which are wound inducible in soybean, were up-regulated by lactofen in both proximal and distal cell zones in minimally wounded cotyledons and further enhanced in wounded tissues. Moreover, if the wall glucan elicitor from Phytophthora sojae was present during lactofen treatment, the induction of isoflavone synthase was even more rapid. These results are consistent with the fact that lactofen triggers massive isoflavone accumulations and activates the capacity for glyceollin elicitation competency. In addition, lactofen induces late expression of a selective set of pathogenesis-related (PR) protein genes, including PR-1a, PR-5, and PR-10, mainly in treated proximal tissues. These various results are discussed in the context of singlet oxygen-induced responses and lactofen's potential as a disease resistance-inducing agent.|A technical grade of lactofen (1'[carboethoxy]ethyl 5-[2-chloro-4-[trifluoro-methyl] phenoxy]-2-nitrobenzoate) has been shown to induce liver tumors in mice. To determine a possible mechanism of action, the effect of exposure for 7 weeks to dietary concentrations of 2, 10, 50, and 250 ppm technical grade lactofen and 250 ppm of pure lactofen was studied for various liver parameters in groups of male and female CD-1 mice. Liver-weight to body-weight ratio, liver catalase, liver acyl-CoA oxidase, liver cell cytoplasmic eosinophilia, nuclear and cellular size, and peroxisomal staining were increased by the tumorigenic dose of lactofen, i.e., 250 ppm, in a fashion similar to the comparison chemical nafenopin (500 ppm), which is a peroxisome proliferator. Lower doses of lactofen that were reported as nontumorigenic had little or no effect on these parameters.|Based on the weight-of-the-evidence of the toxicity database, there are sufficient data to classify lactofen as a non-genotoxic hepatocarcinogen in rodents with peroxisome proliferation being a plausible mode of action. Studies with transgenic mouse confirmed that essentially all of the of the effects of PPs in rodent liver are mediated by PPAR .

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 suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)

/SIGNS AND SYMPTOMS/ Lactofen has low acute toxicity via the oral, dermal, and inhalation routes of exposure; causes mild skin irritation; and is not a dermal sensitizer. The manufacturing use product is a moderate eye irritant.

1'-(carboethoxy)ethyl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoate

Approximately 235,000 pounds of lactofen ai are applied annually to nearly 2.2 million acres. Lactofen's largest markets in terms of total pounds of ai applied annually are soybeans (85%) and cotton (12%). The remaining use is primarily on fresh beans.|(1992) 355,415 pounds

USEPA/OPP Pesticide Code 128888; Trade Names: PPG-844, Cobra herbicide.|COBRA HERBICIDE Active Ingredient 24.0% Lactofen|LACTOFEN MANUFACTURING CONCENTRATE Active Ingredient 60.0% Lactofen|STELLAR HERBICIDE Active Ingredient 7.6% Flumiclorac pentyl ester, 26.6% Lactofen|For more Formulations/Preparations (Complete) data for LACTOFEN (7 total), please visit the HSDB record page.

Lactofen may be applied by aerial and ground application; band treatment, broadcast, directed spray, low volume spray, soil broadcast treatment, and soil incorporation. It is generally applied at a rate of 1 lb active ingredient (ai) per acre (A) or less per application. No more than 1 lb ai/A lactofen may be applied to a site in a single year.|This product is for use in further preparation of herbicide products; for formulation use only. /Lactofen technical/|V-10086 Herbicide is a selective, broad specturm herbicide for preemergence and postemergence control of susceptible broadleaf weeds. V019986 is formulated as an emulsifiable concentrate containing 2 lbs of ai per gallon. ... V-10086 works primarily through contact action.

EPA Method PMD-LTF-LC1. Determination of Lactofen in Technical and EC Formulated Materials by High Performance Liquid Chromatography.|EPA Method PMD-LTF-LC2. Determination of Lactofen in Technical and EC Formulated Materials by Internal Standard High Performance Liquid Chromatography.|FDA Method 211.1. Organochlorine Residues (Nonionic) General Method for Fatty Foods Including Extraction of Fat, Acetonitrile Partition, Florisil Column Cleanup, Partition Chromatography Cleanup, and Supplemental Cleanup.