Flufenacet

White to tan solid

White solid

Solubility in organic solvents (g/L at 20 °C): n-hexane - 8.7; toluene - >200; dichloromethane - >200; 2-propanol - 170; 1-octanol - 88; polyethylene glycol - 74; acetone - >200; dimethylformamide - >200; acetonitrile - >200; dimethylsulfoxide - >200

In water, 56 mg/L (pH 4) at 25 °C; 56 mg/L (pH 7) at 25 °C; 54 mg/L (pH 9) at 25 °C

0.00000067 [mmHg]

6.75X10-7 mm Hg at 20 °C (6.0X10-2 mPa at 20 °C)

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]；H317: May cause an allergic skin reaction [Warning Sensitization, Skin]；H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P319, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

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

03/84/EC, Reg. (EU) 2016/950, Reg. (EU) 2017/1511, Reg. (EU) 2018/1262, Reg. (EU) 2019/1589, Reg. (EU) 2020/1511, Reg. (EU) 2021/1449, Reg. (EU) 2022/1480, Reg. (EU) 2023/1757, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012

Tolerances are established for the combined residues of the herbicide flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety in or on the following commodities.[Table#6615]

Tolerances are established for combined residues of flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide, and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety, with regional registration.[Table#6616]

Tolerances are established for indirect or inadvertent residues of the herbicide flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety in or on the following raw agricultural commodities when present therein as a result of application of flufenacet to the growing crops in paragraph (a) of this section.[Table#6617]

Acute Tox. 4 (100%)；Skin Sens. 1 (100%)；STOT RE 2 (100%)；Aquatic Acute 1 (100%)；Aquatic Chronic 1 (100%)

Acute toxicity - category 4；Specific target organ toxicity (repeated exposure) - category 2；Skin sensitisation - category 1；Hazardous to the aquatic environment (acute) - category 1；Hazardous to the aquatic environment (chronic) - category 1

Hazardous to the aquatic environment (Acute) - Category 1；Hazardous to the aquatic environment (Long-term) - Category 1

Acute toxicity (Oral) - Category 4；Skin sensitization - Category 1B；Specific target organ toxicity - Single exposure - Category 1 (nervous system)；Specific target organ toxicity - Repeated exposure - Category 2 (nervous system, eye, blood system, liver, kidney)

Acute Tox. 4 *；STOT RE 2 *；Skin Sens. 1；Aquatic Acute 1；Aquatic Chronic 1

Suitable Extinguishing Media: water, carbon dioxide (CO2), dry chemical, foam. /Axiom DF Herbicide/

Fire Fighting Instructions: Dike area to prevent runoff and contamination of water sources. Avoid contact with spilled product or contaminated surfaces. Keep out of smoke. Cool closed containers exposed to fire with water spray. Fight fire from upwind position. Collect contaminated fire extinguishing water separately. This must not be discharged into drains. Firefighters should wear NIOSH approved self-contained breathing apparatus and full protective clothing. /Axiom DF Herbicide/

Store in cool dry place. Storage above 100 °F results in loss of active ingredient.

Store in a cool, dry place and in such a manner as to prevent cross contamination with other pesticides, fertilizers, food, and feed. Store in original container and out of the reach of children, preferably in a locked storage area. /Axiom DF 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.

Container Disposal: Non-refillable container. Do not reuse or refill this container. Offer for recycling, if available. Completely empty bag into application equipment. Then dispose of empty bag in a sanitary landfill or by incineration, or if allowed by State and local authorities, by burning. If burned, stay out of smoke.. /Axiom DF Herbicide/

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.

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

User should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet; Remove clothing/PPE 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. /Axiom DF Herbicide/

Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry. /Axiom DF 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.. /Axiom DF Herbicide/

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

Tolerances are established for the combined residues of the herbicide flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety in or on the following commodities.[Table#6610]

Tolerances are established for combined residues of flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide, and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety, with regional registration.[Table#6611]

Tolerances are established for indirect or inadvertent residues of the herbicide flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety in or on the following raw agricultural commodities when present therein as a result of application of flufenacet to the growing crops in paragraph (a) of this section.[Table#6612]

Applicators and other handlers must wear: long-sleeved shirt and long pants, chemical-resistant gloves made of any waterproof material such as polyethylene or polyvinyl chloride, shoes plus socks. /Axiom DF Herbicide/

Restricted entry interval (REI) of 12 hours following application. ... 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 made of any waterproof material, shoes plus socks. /Axiom DF Herbicide/

LD50; Species: /Colinus virginianus/ (Bobwhite quail) 1608 mg/kg /Conditions of bioassay not specified./

LC50; Species: /Colinus virginianus/ (Bobwhite quail) diet >5317 ppm for 5 days

LC50; Species: /Anas platyrhynchos/ (Mallard duck) diet >4970 ppm for 5 days

LD50; Species: Apis mellifera (Honey Bee) worker; topical, general >25 ug/bee for 48 hr

For more Ecotoxicity Values (Complete) data for FLUFENACET (17 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 113 to 4602(2-3), indicate that flufenacet is expected to have high to slight mobility in soil(SRC). However, various field studies have shown that flufenacet does not leach below 15 cm of the top soil(4-5). Volatilization of flufenacet from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-9 atm-cu m/mole(SRC), based upon its vapor pressure, 6.75X10-7 mm Hg(6), and water solubility, 56 mg/L(6). Half-lives for aerobic microbial degradation of flufenacet range from 10 to 34 days in varying soil types at approximately 1.0 ppm at 20-21 °C(2). Under anaerobic conditions (flooded soil) for a 6 month incubation period, flufenacet had a half-life of 240 days; however, most of the flufenacet dissipated by binding to the soil matrix(7). Flufenacet is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). In sandy loam soil surface tests, using a flufenacet concentration of 6.2 ppm at 25 °C and artificial sunlight, the photodegradation half-life was observed as >30 days(2).

TERRESTRIAL FATE: Dissipation of flufenacet was studied under laboratory conditions in three types of soil at different concentrations and soil moisture content(1). Flufenacet half-lives were reported as 10.1 to 22.3 days in Delhi soil (0.864% organic matter, pH 7.69, 77.5% sand, 17.5% silt, 5.0% clay), 10.5 to 24.1 days in Ranchi soil (0.072% organic matter, pH 5.54, 60.0% sand, 8.7% silt, 31.3% clay), and 29.2 to 31.0 days in Nagpur soil (0.688% organic matter, pH 8.25, 40.0% sand, 16.3% silt, 43.7% clay)(1).

TERRESTRIAL FATE: Distribution of radioactive flufenacet residues from Fresno topsoil (0-3 cm). Degradates include flufenacet alcohol, flufenacet oxalate, flufenacet sulfonic acid, and others that were not identified(1).[Table#6613]

TERRESTRIAL FATE: Distribution of radioactive flufenacet residues from Chualar topsoil (0-3 cm). Degradates include flufenacet alcohol, flufenacet oxalate, flufenacet sulfonic acid, and others that were not identified(1).[Table#6614]

For more Environmental Fate (Complete) data for FLUFENACET (6 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ Two chronic toxicity studies are available for birds. Statistically significant reductions occurred in the number of eggs laid/set, viable embryos, hatchlings, and survivors in Mallard ducks. The most sensitive endpoint was the number of 14-day hatchlings. Similarly, a statistically significant increase in the number of eggs cracked and a decrease in normal hatchlings and survivors were observed in Bobwhite Quail. The most sensitive endpoints were numbers of 14-day hatchlings, eggs cracked and normal hatchlings. Hatching survivor weight was also affected.

/AQUATIC SPECIES/ Two chronic studies are available testing chronic toxicity of flufenacet to freshwater fish. The first, an early life-stage toxicity test, was conducted using rainbow trout. Delays in growth and development of fry were demonstrated to occur at concentrations of flufenacet in water as low as 0.334 ppm. The second, a full life cycle study, used fathead minnows. No treatment-related effects were observed on embryo survival, hatching success, larval, juvenile, or adult survival of the F0 generation. In addition, no significant treatment-related effects were observed on egg production at any test level. Growth was affected by treatment with flufenacet: the most sensitive endpoint was adult male weight at test termination (Day 254), with a NOAEC of 0.075 ppm a.i. Growth was also affected at the 1.211 ppm a.i. level 4 wk post-hatch in the filial generation. No other treatment-related effects were observed on hatching success, or egg or alevin/fry survival. Based on the male test termination weights of the F0 generation, the NOAEC and LOAEC are 0.075 and 0.138 ppm a.i., respectively.

Flufenacet Koc values have been measured: 613 in sand (0.3% organic matter, 5% clay, pH 5); 742 in sandy loam (0.4% organic matter, 7.5% clay, pH 6,4); 354 in sandy loam (2.4% organic matter, 5% clay, pH 6.4); 213 in silt loam (2.9% organic matter, 17% clay, pH 5.9); 233 in clay loam (2.2% organic matter, 29% clay, pH 6.4); 113 in loam (7.3% organic matter, 8% clay, pH 7.1); and 144 in silt loam (4.7% organic matter, 24% clay, pH 7.3)(1). Koc values were also reported as: 1802 in sandy loam (7% clay, 38% silt, 55% sand, 1.72% organic matter, pH 7.0); 1231 in clay loam (36% clay, 45% loam, 19% sand, 2.12% organic matter, pH 6.6); 4602 in loamy sand (10% clay, 11% silt, 79% sand, 1.60% organic matter, pH 6.4); and 1257 in silt loam (14% clay, 75% silt, 11% sand, 1.2% organic matter, pH 6.7)(2). According to a classification scheme(3), the measured Koc range of 113 to 4602 suggests that flufenacet is expected to have high to slight mobility in soil. Flufenacet had Kd values of 1.57 to 4.43 in alluvial soil from Delhi (pH 7.1, 0.34% organic carbon, 19.7% clay, 64.7% sand, 15.6% silt)(4). In a Belgium corn field study using sandy loam soil (2.2% organic matter), most of the applied flufenacet remained in the 0-10 cm surface soil layer; traces were detected in the 10-15 cm soil layer during the 2 to 3 month period after treatment; flufenacet was never detected in the 15-20 cm soil layer(5).

An outdoor soil study with [phenyl-U-14C]flufenacet was conducted in two sandy loams collected from Chualar and Fresno sites in California. Plots were treated with an equivalent rate of 0.89 lb/acre. Samples were collected up to 88 days after treatment. Soil characteristics for Chualar soil are 1.3% organic matter, 70.0% sand, 18.0% silt, 12.0% clay, pH 6.4; for Fresno soil 0.5% organic matter, 64.7% sand, 31.3% silt, 4.0% clay, pH 7.5. Bound residues at depths of 3 to 13 cm were measured in both soils starting at day 15; Fresno soil (day:% bound residue) 15:8.9, 19:6.6, 27:11.6, 35:15.6, 46:6.9, 88:22.1; Chualar soil (day:% bound residue) 15:11.1, 19:12.7, 27:6.0, 35:1.0, 46:5.1, 88:6.3(1).

AEROBIC: Half-lives for aerobic microbial degradation of flufenacet range from 10 to 34 days in varying soil types at approximately 1.0 ppm at 20-21 °C(1); major degradation products under aerobic conditions are N-(4-fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamide, 4-fluoro-N-methylaniline-sulfoacetamide, [4-fluorophenyl)(1-methylethyl)-amino]oxoacetic acid, and 3-trifluoromethyl-1,3,4-thiadiazol-2(3H)one(1). Using radio-labeled flufenacet and a sandy loam soil from Howe, IN, degradation of flufenacet under aerobic conditions was bi-phasic, characterized by rapid degradation during the first 28 days followed by slower degradation during the remainder of the study. Assuming first-order kinetics, the half-life was 33 to 64 days(2).

ANAEROBIC: Under anaerobic conditions (flooded soil) for a 6 month incubation period, flufenacet had a half-life of 240 days; however, most of the flufenacet dissipated by binding to the soil matrix(1).

An estimated BCF of 60 was calculated in fish for flufenacet(SRC), using a log Kow of 3.20(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Henry's Law constant for flufenacet is estimated as 5.8X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 6.75X10-7 mm Hg(1), and water solubility, 56 mg/L(1). This Henry's Law constant indicates that flufenacet is expected to be essentially nonvolatile from moist soil and water surfaces(2). Flufenacet is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... Male rats were surgically thyroidectomized and provided thyroid hormone replacement therapy via implanted osmotic minipumps capable of maintaining a T4/triiodothyronine (T3) serum concentration for approximately 4 weeks at a level comparable to that of euthyroid controls. Seven days after minipump implantation, thyroidectomized + T4/T3 (TX + T4/T3) and nonthyroidectomized intact rats (NTX) were fed diets containing 0, 25, 1000, or 3000 ppm FOE 5043 for up to 3 weeks. Dose-related and equivalent declines in total and free serum T4 levels in both TX + T4/T3 and NTX rats were measured at Weeks 1, 2, and 3. Alterations in thyrotropin, total, free, and reverse serum T3 levels were also noted in both TX and NTX animals; however, a compound-related trend was difficult to discern and, when compared to the T4 response, the changes were markedly less consistent with respect to both time and dose. Additionally, dose-related increases in absolute and relative liver weights were measured in both TX + T4/T3 and NTX animals.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In the rat chronic feeding / carcinogenicity study the NOEL was less than 1.2 mg/kg/day in males and less than 1.5 mg/kg/day in females and the LOEL was 1.2 mg/kg/day in males and 1.5 mg/kg/day in females based on methemoglobinemia and multi-organ effects in blood, kidney, spleen, heart, and uterus. Under experimental conditions the treatment did not alter the spontaneous tumor profile.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In the mouse carcinogenicity study the NOEL was less than 7.4 mg/kg/day in males and was 9.4 mg/kg/day for females and the LOEL was 7.4 mg/kg/day for males and was 38.4 mg/kg/day for females based on cataract incidence and severity. ... /SRP: No data about tumor incidence was reported/

/OTHER TOXICITY INFORMATION/ Treatment with FOE 5043 at a rate of 1000 ppm as a dietary admixture was found to significantly increase the clearance of (125I)T4 from the serum, suggesting an enhanced excretion of the hormone. In the liver, the activity of hepatic uridine glucuronosyl transferase, a major pathway of thyroid hormone biotransformation in the rat, increased in a statistically significant and dose-dependent manner; conversely, hepatic 5'-monodeiodinase activity trended downward with dose. Bile flow as well as the hepatic uptake and biliary excretion of (125I)T4 were increased following exposure to FOE 5043. Thyroidal function, as measured by the discharge of iodide ion in response to perchlorate, and pituitary function, as measured by the capacity of the pituitary to secrete thyrotropin in response to an exogenous challenge by hypothalamic thyrotropin releasing hormone, were both unchanged from the controlled response.

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

03/84/EC, Reg. (EU) 2016/950, Reg. (EU) 2017/1511, Reg. (EU) 2018/1262, Reg. (EU) 2019/1589, Reg. (EU) 2020/1511, Reg. (EU) 2021/1449, Reg. (EU) 2022/1480, Reg. (EU) 2023/1757, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012

Tolerances are established for the combined residues of the herbicide flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety in or on the following commodities.[Table#6615]

Tolerances are established for combined residues of flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide, and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety, with regional registration.[Table#6616]

Tolerances are established for indirect or inadvertent residues of the herbicide flufenacet, N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide and its metabolites containing the 4-fluoro-N-methylethyl benzenamine moiety in or on the following raw agricultural commodities when present therein as a result of application of flufenacet to the growing crops in paragraph (a) of this section.[Table#6617]

Treatment with FOE 5043 at a rate of 1000 ppm as a dietary admixture was found to significantly increase the clearance of (125I)T4 from the serum, suggesting an enhanced excretion of the hormone. In the liver, the activity of hepatic uridine glucuronosyl transferase, a major pathway of thyroid hormone biotransformation in the rat, increased in a statistically significant and dose-dependent manner; conversely, hepatic 5'-monodeiodinase activity trended downward with dose. Bile flow as well as the hepatic uptake and biliary excretion of (125I)T4 were increased following exposure to FOE 5043. Thyroidal function, as measured by the discharge of iodide ion in response to perchlorate, and pituitary function, as measured by the capacity of the pituitary to secrete thyrotropin in response to an exogenous challenge by hypothalamic thyrotropin releasing hormone, were both unchanged from the controlled response.

A rat metab study showed that radiolabeled flufenacet was rapidly absorbed & metabolized by both sexes. ... A max of 7% of admin dose was found in the tissue & residual carcass. 39 metabolites were detected in excreta & 23 were positively identified.

A rat metab study showed that radiolabeled flufenacet was rapidly absorbed & metabolized by both sexes. Urine was the major route of excretion at all dose levels & smaller amounts were excreted via the feces. A max of 7% of admin dose was found in the tissue & residual carcass. 39 metabolites were detected in excreta & 23 were positively identified.

Used as pre-emergence herbicide to control annual grasses and broadleaf weeds in corn and soybeans; [HSDB]

Farming (Pesticides) [Category: Industry]

For flufenacet (USEPA/OPP Pesticide Code: 121903) 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./

Pre-plant-incorporated, pre-plant-surface, pre-emergence in maize and soya beans, pre-planting in tomatoes, pre-emergence in potatoes and sunflowers, and post-emergence in maize, wheat and rice.

Flufenacet is applied to the soil surface or incorporated preemergence in field corn, corn grown for silage, or soybeans to control certain annual grasses and broadleaf weeds.

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

USEPA/OPP Pesticide Code 121903; Trade Names: FOE 5043 Technical.

Dry flowable, soluble concentrate.

Emulsifiable concentrate; granule; suspension concentrate; water dispersible granule; wettable powder.

Premix Partners: Atrazine; Diflufenican; Isoxaflutole; Metosulam; Metribuzin.

For more Formulations/Preparations (Complete) data for FLUFENACET (14 total), please visit the HSDB record page.

Environmental transformation -> Pesticides (parent, predecessor)

Herbicides

Pesticides -> Herbicides -> Amide herbicides -> Anilide herbicides

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

FOE 5043 DF Herbicide formulation applied by ground only at 12 to 21 ounces per acre to corn and 7 to 12 ounces per acre to soybeans. Axiom DF Herbicide formulation applied by ground only at 13 to 23 ounces per acre to corn and 7 to 13 ounces per acre to soybeans.