5-[2-Chlor-4-(trifluormethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamid

White crystalline solid

White crystalline solid

Solubility at 25 °C (mg/mL): propylene glycol 631; octanol 12; ethyl decanoate 10 /Fomesafen sodium salt/

In water, 50 mg/L at 20 °C

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

Decomposed by light.

0.00000075 [mmHg]

<4X10-3 mPa /<3.0X10-8 mm Hg/ at 20 °C

Fomesafen is a white crystalline solid. Used as an herbicide.

Colorless or white solid; [HSDB]

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Warning

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

2002/2076

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.)

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 mild skin irritant; A mild to moderate eye irritant, based on animal studies; [HSDB] May cause irritation; [MSDSonline] See Fluthiacet-methyl.

Tolerances are established for residues of the herbicide fomesafen, including its metabolites and degradates, in or on the following commodities. Compliance with the tolerance levels specified in the following table below is to be determined by measuring only fomesafen, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide, in or on the commodity. [Table#6137]

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Fomesafen sodium is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 123802; Type of Pesticide: conventional - herbicide; Use Site: food use, trees, non-agricultural use; Year: 1987.

Acute Tox. 4 (100%)；Acute Tox. 4 (17.5%)；Acute Tox. 4 (49.1%)；Aquatic Acute 1 (13.2%)；Aquatic Chronic 1 (13.2%)

Acute toxicity - category 4

Carcinogens

Acute Tox. 4 *

Fomesafen is severely irritating to the eye and is moderately irritating to the skin.

Mild skin irritant; mild to moderate eye irritant (rabbits).

Use dry chemical, foam or CO2 extinguishing media. Wear full protective clothing and self-contained breathing apparatus. Evacuate nonessential personnel from the area to prevent human exposure to fire, smoke, fumes or products of combustion. Prevent use of contaminated buildings, area, and equipment until decontaminated. Water runoff can cause environmental damage. If water is used to fight fire, dike and collect runoff. /Reflex Herbicide/

Store above 32 °F in original containers only. If product freezes, return to room temperature and agitate to reconstitute. Keep container closed when not in use. Do not store near food or feed. /Reflex Herbicide/

Store the material in a well-ventilated, secure area out of reach of children and domestic animals. Do not store food, beverages or tobacco products in the storage area. Prevent eating, drinking, tobacco use, and cosmetic application in areas where there is a potential for exposure to the material. Wash thoroughly with soap and water after handling. /Reflex Herbicide/

Do not contaminate water when disposing of equipment washwater or rinsate. /Reflex Herbicide/

In case of spill or leak on floor or paved surfaces, soak up with sand, earth or synthetic absorbent. Remove to chemical waste area. /Reflex Herbicide/

Control the spill at its source. Contain the spill to prevent from spreading or contaminating soil or from entering sewage and drainage systems or any body of water. Clean up spills immediately, ... . Cover entire spill with absorbing material and place into compatible disposal container. Scrub area with hard water detergent (e.g. commercial products such as Tide, Joy, Spic and Span). Pick up wash liquid with additional absorbent and place into compatible disposal container. Once all material is cleaned up and placed in a disposal container, seal container and arrange for disposition. /Reflex Herbicide/

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /Reflex Herbicide/

Do not apply directly to water, or to areas where surface water is present, or to intertidal areas below the mean high water mark. /Reflex Herbicide/

Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application. /Reflex Herbicide/

For more Preventive Measures (Complete) data for FOMESAFEN (9 total), please visit the HSDB record page.

Tolerances are established for residues of the herbicide fomesafen, including its metabolites and degradates, in or on the following commodities. Compliance with the tolerance levels specified in the following table below is to be determined by measuring only fomesafen, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide, in or on the commodity. [Table#6136]

Applicators and other handlers must wear: Long-sleeved shirt and long pants; Chemical-resistant gloves such as barrier laminate or Viton; Shoes plus socks; Protective eyewear. /Reflex Herbicide/

... For aerial applications mixers and loaders handling more than 140 gallons of Reflex Herbicide in any single workday must wear: Dust/mist filtering NIOSH-approved respirator with any N, R, P, or HE filter. /Reflex Herbicide/

... Restricted entry interval (REI) of 24 hours. 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; Chemical-resistant gloves such as barrier laminate or Viton; Shoes plus socks; Protective eyewear. /Reflex Herbicide/

Chemical-resistant gloves. Protective eyewear.

Field studies were conducted in 1994 and 1995 in central and southern Illinois to compare several total postemergence weed control programs in soybean (Glycine max (L.) Merr.). Herbicide programs evaluated were imazethapyr (an acetolactate synthase (ALS) inhibiting herbicide) applied alone or in combination with lactofen and two non-acetolactate synthase herbicide programs consisting of combinations of bentazon, acifluorfen, and sethoxydima and combinations of fomesafen, fluazifop, and fenoxyprop. These treatments were applied early postemergence (EPOST, V-1 soybean-first trifoliate) and postemergence (POST, V-2 soybean-second trifoliate). Non-acetolactate synthase herbicide programs generally provide more effective weed control postemergence, while weed control with imazethapyr tended to be greater early postemergence. Non-acetolactate synthase herbicide programs applied postemergence provided weed control levels that were equal to imazethapyr in three out of four experiments. In 1994 at Brownstown, broadleaf weed control was poor with non-acetolactate synthase herbicide programs when weed growth stages were larger and environmental conditions more extreme than other experiments. Adding lactofen to imazethapyr increased broadleaf weed control in some instances but decreased giant foxtail (Setaria faberil L.) control. Imazethapyr plus lactofen tended to produce the greatest degree of soybean injury.

Broadleaf weed and yellow nutsedge control with herbicide programs containing pendimethalin and combinations of fomesafen, fluometuron, and norflurazon applied alone or with POST-directed applications of MSMA or fluometuron plus MSMA was evaluated. Soil-applied herbicide combination containing formesafen controlled yellow nutsedge better than combinations of norflurazon and fluometuron but did not provide better entireleaf, ivyleaf, pitted, and tall morningglory or sicklepod control. Fluometuron plus MSMA controlled morningglories and sicklepod more effectively than MSMA. Seed cotton yield was greater in one of two years when fomesafen was applied and was associated with better yellow nutsedge control.

The objective of on-farm herbicide screening experiment sin soybean was to assess the efficacy of new herbicides and herbicide combinations for weed control in two tillage systems in Lusaka Province, Zambia weed control treatments consisted of two control treatments (no-weeding and clean weeding with a hand hoe), two standard treatments (metribuzin + metolachlor and fomesafen + fluazifop-butyl) and seven test herbicides/herbicide combinations (oxadiazon, oxadiazon + metolachlor, imazethapyr, acifluorfen + fluazifop-butyl, bentazone + fluazifop-butyl, bentazone + fenoxaprop-ethyl and bentazone + acifluorfen). Loss of potential yield owing to uncontrolled weeds was 66% and 40% under conventional and minimum tillage, respectively. All herbicide treatments performed well wider conventional tillage, whereas none of the treatments was able to satisfactorily control weeds under minimum tillage, especially Euphorbia heterophylla and late weeds. Standard herbicide treatments performed well under both tillage systems.

Field studies were conducted to determine rhizomatous johnsongrass and barnyardgrass control with clethodim, quizalofop-P-ethyl, fluazifop-P, sethoxydim, fenoxaprop-ethyl, and quizalofop-P-tefuryl applied alone and with lactofen, imazaquin, chlorimuron, and fomesafen. Graminicides applied alone controlled johnsongrass and barnyardgrass 83 to 99%. Of the graminicides evaluated, clethodium was the most antagonistic of the broadleaf herbicides toward the activity of graminicides. Clethodim mixed with imazaquin reduced johnsongrass control as much as 64% and mixed with chlorimuron reduced barnyardgrass control as much as 52%. Quizalofop-P-tefuryl was least affected by broadleaf herbicides and fomesafen was least antagonistic in mixtures with graminicides.

For more Interactions (Complete) data for FOMESAFEN (7 total), please visit the HSDB record page.

LD50; Species: Anas platyrhynchos (Mallard duck) oral >5000 mg/kg

LC50; Species: Anas platyrhynchos (Mallard Duck, age 11 days) diet >20000 ppm for 8 days

LC50; Species: Colinus virginianus (Northern Bobwhite Quail, age 14 days) diet >20000 ppm for 8 days

LD50; Species: Apis mellifera (Honey Bee, worker) topical >100 ug/bee for 48 hr

For more Ecotoxicity Values (Complete) data for FOMESAFEN (14 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 34 to 1200(2-4), indicate that fomesafen is expected to have very high to low mobility depending on the soil(SRC). The pKa of fomesafen is 2.83(2), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of fomesafen from moist soil surfaces is not expected to be an important fate process(SRC) given its pKa. Fomesafen is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of <3.0X10-8 mm Hg at 20 °C(2). Fomesafen has reported biodegradation half-lives of 6 to >12 months under aerobic conditions depending on soil type, and an anaerobic half-life of <3 weeks in soil(6).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 34 to 1200(2-4), indicate that fomesafen is expected to adsorb to suspended solids and sediment(SRC). A pKa of 2.83(2) indicates fomesafen will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(5), a BCF of 6 reported in bluegill(6), suggests bioconcentration in aquatic organisms is low(SRC). Fomesafen is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). Fomesafen may biodegrade in aquatic environments based on anaerobic soil studies reporting a half-life of <3 weeks(8). Fomesafen will photodecompose readily under relatively low intensities of sunlight(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fomesafen, which has a vapor pressure of <3.0X10-8 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase fomesafen may be removed from the air by wet or dry deposition(SRC). Fomesafen contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

/AQUATIC SPECIES/ ...Statistically significant increases in production of reactive oxygen species (ROS) in snails exposed to water concentrations of fomesafen > or =10 ug/L /were noted/. Cellular membrane permeability was increased at exposure concentrations of > or =10 ug/L. Increased cellular permeability may lead to higher percentages of apoptotic and necrotic cells in the population of circulating hemocytes in the snails, but these cells do not necessarily proceed to death. Responses vary across the time course of exposure (24-504 hours) with a lower response generally noted at 504 hours. It is unclear... whether the reduced response is due to a compensatory response by the cells, or overwhelming of cellular processes following extended exposure. At concentrations of < or =270 ug/L for durations < or =504 hours (21 days) there was no observable abnormal behavior, mortality, or reduction of hemocyte cell viability in the snails. It appears that fomesafen induces an immune response in freshwater snails at concentrations that may occur in the environment.

/AQUATIC SPECIES/ The influence of nonylphenol polyethoxylates (NPEO), formulated as the adjuvant Agral 90, on the effects of the diphenyl ether herbicide fomesafen in the pond snail Lymnaea stagnalis was investigated, with particular attention to the reproductive performances and underlying energetic and hormonal processes. Separate short-term exposures to low concentrations of fomesafen and fomesafen-Agral mixture were performed in the laboratory. Outdoor experimental ponds (mesocosms) were used for long-term exposures to higher chemical concentrations. At the concentrations used in the studies, NPEO were known as nontoxic in L stagnalis. Fomesafen was mixed with the adjuvant in the 3:7 ratio recommended for agricultural uses (nominal herbicide concentrations of 22 and 40 ug/L in laboratory and mesocosm, respectively). In mesocosms, multiple application of fomesafen, leading to maximal herbicide concentrations of 60.33 +/- 2.68 ug/L in water, resulted in reduced number of egg masses and altered glycogen metabolism in contaminated snails. These changes, as well as affected steroid-like levels in fomesafen-exposed snails, support the hypothesis of impaired neuroendocrine functions. When Agral 90 was added to the herbicide, results obtained in mesocosms showed that the adjuvant softened the impact of fomesafen. In mesocosms treated with the fomesafen-Agral mixture, significantly lower herbicide levels were found in the water (30.33 +/- 14.91 ug/L at the end of the contamination period). Consequently, internal exposure of the snails to fomesafen was reduced when the herbicide was mixed with the adjuvant.

/AQUATIC SPECIES/ Responses of circulating hemocytes were studied in Lymnaea stagnalis exposed to 10, 30, 90, and 270 ug/L fomesafen for 24 and 504 hr. Flow cytometry was used to quantify fomesafen-induced production of reactive oxygen species (ROS), phagocytic activity on Escherichia coli, and oxidative burst when hemocytes were challenged by E. coli or phorbol 12-myristate-13-acetate (PMA). Lysosomal membrane damage was assessed, using the neutral-red retention time (NRRT) assay. Exposure to fomesafen for 24 h resulted in increase in ROS levels and decreases in phagocytosis and the oxidative burst in PMA-stimulated hemocytes. After 504 h, intracellular levels of ROS returned to normal, but phagocytosis of E. coli was still inhibited and the associated oxidative burst significantly reduced. After both durations of exposure, decreases of NRRT indicated that lysosome membrane fragility increased with fomesafen concentration.

/AQUATIC SPECIES/ Ecotoxicological effects of the diphenyl ether herbicide fomesafen, applied alone or in combination with the adjuvant Agral 90 (mixture of polyethoxylated derivatives of nonylphenol), were assessed on planktonic communities in 18-cu m outdoor mesocosms during a nine-month study. Four mesocosms were treated with fomesafen only (nominal concentration: 40 ug/L), four were treated with the mixture fomesafen-Agral 90 (nominal concentration: 40 ug/L and 90 ug/L, respectively), and four were kept as the controls. Five treatments were performed every three weeks from April 18, 2000. Mean (+/- standard error [SE]) values of fomesafen concentration in water of 62.5 (+/-5.3) and 19.4 (+/-7.6) ug/L were measured at the end of the treatment period in fomesafen- and mixture-treated mesocosms, respectively. Fomesafen, either alone or in mixture with Agral 90, had a significant positive effect on the abundance and biovolume of Cyanobacteria, Cryptophyceae, Dinophyceae, and Bacillariophyceae. Chlorophyceae were inhibited by the herbicide and laboratory toxicity tests confirmed that green algae were more sensitive toward fomesafen than other algal classes. A positive effect of treatments on phytoplankton taxonomic diversity also was observed, indicating that, like natural disturbances of intermediate strength, xenobiotics sometimes may enhance the diversity of algal communities. Fomesafen alone did not have any clear effect on zooplankton. Abundance of calanoid copepods was reduced significantly in the mixture-treated ponds, suggesting either a direct effect of the adjuvant and/or an enhancement of herbicide toxicity by Agral 90. The abundance of other zooplanktonic herbivorous groups increased due to a reduced competition for food for herbivorous species and a higher availability of preys for predators. No algal bloom was observed in the treated ponds, presumably because of grazing pressure and the low availability of nutrients.

For more Ecotoxicity Excerpts (Complete) data for FOMESAFEN (6 total), please visit the HSDB record page.

Fomesafen

Hepatic

Kom values of 86 and 700 were determined for fomesafen in Drummer silt loam and Norfolk sandy loam, respectively(1). These values correspond to Koc values of 150 and 1200, respectively(2). Koc values of 34 to 164(3) and 60(4) were also reported. According to a classification scheme(5), these Koc values suggest that fomesafen is expected to have very high to low mobility in soil(SRC). Sorption of fomesafen by both soils increased as pH decreased: on the Drummer soil sorption increased from 14% at pH 6.3 to 42% at pH 4.7 and 95% at pH 2.0; on the Norfolk soil, fomesafen sorption increased from 5% at pH 5.3 to 15% at pH 4.0 and 55% at pH 2.0(1). The pKa of fomesafen is 2.83(3), indicating that this compound will exist almost entirely in anion form in the environment (pH 5 to 9) and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). In laboratory soil studies, fomesafen was moderately mobile(7). Fomesafen had a mean reported Kd of 4.52 in 5 soil types(8).

/GENOTOXICITY/ In a mammalian cell cytogenetics assay (chromosomal aberrations), human lymphocytes (obtained from one male and one female donor) in culture were exposed to fomesafen (96.7% a.i.) in dimethyl sulfoxide (DMSO) at concentrations of 0, 150, 500, and 1000 ug/ml in the absence of S9-mix and 75, 150, and 250 ug/mL in the presence of S9 mix for 3-3.5 hours and harvested 72 hours after the beginning of treatment. Two-hundred cells (100 per duplicate coded slide) were evaluated for metaphases with structural aberrations. The S9-fraction was obtained from Aroclor 1254 induced male Sprague Dawley rat liver. Fomesafen was tested at concentrations ranging from 150-1000 ug/mL (/without/ S9) and 75-250 ug/mL (+S9). A significant increase in chromosome fragments was observed in lymphocytes from donor 1 at 1000 ug/mL (/without/ S9). However, the clastogenic response is most likely secondary to cytotoxicity as the MI was reduced by 57% in these cells. In the repeat experiment (/without/ S9, donor 1), the MI decreased by 56% and clastogenicity was not observed. Proper experimental protocol was followed and the solvent and positive control values were appropriate. There was no evidence of chromosome aberrations induced over background.

/GENOTOXICITY/ In an in vitro mammalian cell cytogenetics assay (Chromosomal aberrations), human lymphocytes (obtained from 1 male donor) in culture were exposed to fomesafen (97.5% ai) in dimethyl sulfoxide (DMSO) at concentrations of 0, 10, 100, and 1000 ug/ml in the absence and presence of metabolic activation for 3 hours and harvested 26 hours after the beginning of treatment. One-hundred cells (duplicate slides) were evaluated for metaphases with structural aberrations. The S9-fraction was obtained from Aroclor 1254 induced male Sprague Dawley rat liver. Fomesafen was tested up to a cytotoxic concentration for this assay. Cytotoxicity was observed at 1000 ug/ml with and without S-9 mix. No statistically or biologically significant increases in chromosomal damage were observed at any of the dose levels either in the presence or absence of metabolic activation. The solvent and positive controls induced the appropriate response. There was no evidence of chromosome aberrations induced over background.

AEROBIC: In laboratory soil studies under aerobic conditions, half-lives range from about 6 months to >12 months depending on soil type(1).

ANAEROBIC: In soil, fomesafen is rapidly decomposed under anaerobic conditions, with a half-life of <3 weeks(1).

A measured BCF of 6 was reported for fomesafen in bluegill (Lepomis macrochirus) which were exposed over a 28 day period(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

A pKa of 2.83(1) indicates fomesafen will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water and moist soil surfaces is not expected to be an important fate process(SRC). Fomesafen is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of <3.0X10-8 mm Hg(1).

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

2002/2076

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 fomesafen, including its metabolites and degradates, in or on the following commodities. Compliance with the tolerance levels specified in the following table below is to be determined by measuring only fomesafen, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide, in or on the commodity. [Table#6137]

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Fomesafen sodium is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 123802; Type of Pesticide: conventional - herbicide; Use Site: food use, trees, non-agricultural use; Year: 1987.

Using extracts from suspension-cultured cells of soybean (Glycine max cv. Mandarin) as a source of active enzymes, the activities of glutathione transferases (GSTs) catalyzing the conjugation of 1-chloro-2,4-dinitrobenzene (CDNB) and selective herbicides were determined to be in the order in the order CDNB > fomesafen > metolachlor = acifluorfen > chlorimuron-ethyl. Glutathione transferase activities showed a thiol dependence in a substrate-specific manner. Thus, glutathione transferase activities toward acifluorfen and fomesafen were greater when homoglutathione (hGSH), the endogenously occurring thiol in soybean, was used as the co-substrate rather than glutathione (GSH). Compared with glutathione, homoglutathione addition either reduced or had no effect on glutathione transferase activities toward other substrates. In the absence of enzyme, the rates of homoglutathione conjugation with acifluorfen, chlorimuron-ethyl and fomesafen were negligible, suggesting that rapid homoglutathione conjugation in soybean must be catalyzed by glutathione transferases. glutathione transferase activities were subsequently determined in 14-day-old plants of soybean and a number of annual grass and broadleaf weeds. glutathione transferase activities of the plants were then related to observed sensitivities to post-emergence applications of the four herbicides. When enzyme activity was expressed on a mg-1 protein basis, all grass weeds and Abutilon theophrasti contained considerably higher glutathione transferase activity toward CDNB than soybean. With fomesafen as the substrate, glutathione transferase activities were determined to be in the order soybean Digitaria sanguinalis > Sorghum halepense = Setaria faberi with none of the broadleaf weeds showing any activity. This order related well to the observed selectivity of fomesafen, with the exception of A. theophrasti, which was partially tolerant to the herbicide. Using metolachlor as the substrate the order of the glutathione tran

Metabolism of fomesafen was accompanied by a transient accumulation of a metabolite identified as (N-(4-(4-(trifluoromethyl)phenoxy)-2-methanamidephenyl)acetamide) using liquid chromatography-mass spectrometry, thus indicating a metabolic pathway involving /of the nitro group and acetylation of the resultant amino group/.

Used as post-emergence herbicide for control of broad-leaved weeds in soy beans and other legumes; [Merck Index]

Farming (Pesticides) [Category: Industry]

For fomesafen sodium (USEPA/OPP Pesticide Code: 123802) 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./ /Fomesafen sodium/

Postemergence herbicide, over the top, on soybeans

Field experiments were conducted from 1991 to 1993 to evaluate eclipta, Eclipta prostrate L., control and peanut, Arachis hypogaea L., response to herbicide treatments. Formesafen (5-(2-chloro-4-(trifluoromethyl)phenoxy)-N-(methylsulfonyl)-2-nitrobenzamide) applied at cracking was the only preemergence-applied herbicide which provided season-long control (>84%). Herbicides applied postemergence were more effective when the eclipta was less than 5 cm in height. Minor peanut injury was observed at the early season rating from several herbicides; however, all injury had disappeared by the late season rating. Eclipta control did not consistently improve peanut pod yield.

Fomesafen is manufactured by reaction of 2-chloro-4-trifluoromethylphenolate with 4-chloro-N-methylsulfonyl-2-nitrobenzamide.

Acifluorfen + ammonia + methanesulfonyl chloride (amide formation/sulfonamide formation).

Aqueous concentration, liquid concentration.

Premix Partners: S-Metolachlor; Fenoxaprop-P-ethyl; Fluazifop-P-butyl; Glyphosate.

Basagran Herbicide (BASF Corporation) Sodium bentazon 44% /Formesafen sodium/

Basagran M-60 Herbicide (BASF Corporation) MCPA, dimethylamine salt 6.2%, Sodium bentazon 37% /Formesafen sodium/

For more Formulations/Preparations (Complete) data for FOMESAFEN (12 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies fomesafen (technical grade) as Class II: moderately hazardous; Main Use: herbicide.

Fomesafen was used on the following crops during the 1990 to 1993 crop years (from federal and state pesticide use surveys), by crop (State, % of crop acreage treated based on estimates of the crop's 1992 planted acreage): green beans (AR, 70%; IL, 50%) and soybeans (AL, 10%; AR, 13%; FL, 2%; GA, 2%; IL, 2%; IN, 2%; KY, 16%; LA, 15%; MI, 3%; MS, 10%; MO, 2%; NC, 6%; OH, 3%; SC, 6%; and TN, 9%).