1-メチル-3-(3-トリフルオロメチルフェニル)-5-フェニルピリジン-4(1H)-オン

Pesticide -> EPA IRIS

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Other

Pesticide (Fluridone) -> USDA PDB

log Kow = 1.87 at pH 7, 25 °C

3.16

Solubility in methanol, chloroform, diethyl ether: >10 g/L; in ethyl acetate: >5 g/L; in hexane: <0.5 g/L

In water, 12 mg/L at pH 7, 25 °C

0.0000001 [mmHg]

0.013 mPa (9.8X10-8 mm Hg) at 25 °C

This chemical does not meet GHS hazard criteria for 1.2% (1 of 86) of reports.

Danger

H311 (80.2%): Toxic in contact with skin [Danger Acute toxicity, dermal]

P262, P264, P264+P265, P270, P273, P280, P302+P352, P305+P351+P338, P316, P321, P337+P317, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 86 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

2002/2076

Fluridone: HSNO Approval: HSR007538 Approved with controls

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 112900; Type of Pesticide: conventional - herbicide; Use Site: aquatic/non-food; Year: 1986.

Keep away from children. Store in original container. Do Not contaminate water, food, feed by storage or disposal.

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.

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 applying the product/ 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.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

LD50 /Colinus virginianus/ (Bobwhite quail) oral >2000 mg/kg

LC50 /Colinus virginianus/ (Bobwhite quail) dietary >5000 mg/kg/8 days

LC50 /Anas platyrhynchos/ (Mallard duck) dietary >5000 mg/kg/8 days

LC50 /Oncorhynchus mykiss/ (Rainbow Trout) 11.7 mg/L/ 96 hr /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for FLURIDONE (34 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranged from 350 to 2,462(2-4), indicate that fluridone is expected to have low to slight mobility in soil(SRC). The pKa of fluridone is 12.3 (tertiary amine)(6), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(7). Volatilization of fluridone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 9.8X10-8 mm Hg(5), and water solubility 12 mg/L(6). Fluridone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). A biodegradation half-life of 360 days was reported in aerobic soil(8). In field studies using different soil types, <10% of the originally applied fluridone was found after 220 days in Miller clay and 20% was found remaining after 385 days in Lufkin fine sandy loam soil(9). In laboratory studies, fluridone persistence in non-sterilized soils after 210 days was 62, 44, 10, and 5% in Lufkin fine sandy loam, Miller clay, Hidalgo sandy clay loam, and Brennan fine sandy loam, respectively(9). In Miller clay and Lufkin fine sandy loam no difference was observed in the rate of fluridone degradation between sterilized and non-sterilized samples; however, significant differences in degradation were observed between sterilized and non-sterilized Brennan fine sandy loam and Hidalgo sandy clay loam(9).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranged from 350 to 2,462(2-4), indicates that fluridone may adsorb to suspended solids and sediment(SRC). The pKa of fluridone is 12.3 (tertiary amine)(7), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb more strongly to suspended solids and sediment than their neutral counterparts(8). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of 3.5X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 9.8X10-8 mm Hg(6) and water solubility, 12 mg/L(7). According to a classification scheme(9), BCF values ranging from 0 to 91(10-13), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Fluridone is stable to hydrolysis(4,14). Aqueous photolysis half-lives ranging from 1 to 6 days were reported in various studies(4). Photodegradation was found to be the major degradation pathway of fluridone in aquatic systems under actual-use conditions(15). A half-life of 12 months was reported for fluridone in sediment under laboratory conditions and 17 weeks under field conditions(15). Fluridone was reported to dissipate with average half-lives of 20 days and 3 months in pond water and in pond hydrosoil, respectively(16). A half-life of 4 days was observed for fluridone after treatment in a pond(17). A half-life of 1 year or more was observed for fluridone in hydrosoils(17).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluridone, which has a vapor pressure of 9.8X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase fluridone may be removed from the air by wet or dry deposition(SRC).

/AQUATIC SPECIES/ The acute median lethal concentrations (LC50s) of fluridone were 4.3 plus or minus 3.7 mg/L for invertebrates and 10.4 plus or minus 3.9 mg/L for fish. In chronic studies, no effects were detected when daphnids (Daphnia magna ) were continuously exposed to fluridone concentrations of 0.2 mg/L or less for 32 days, amphiopods (Gammarus pseudolimnaeus ) to 0.6 mg/L or less for 60 days or midge larvae (Chironomus plumosus ) to 0.6 mg/L or less for 30 days. Fathead minnows (Pimephales promelas ) were not affected by continuous exposure to fluridone concentration of 0.48 mg/L or less over their life cycle. The growth and survival of channel catfish (Ictalurus punctatus ) were not adversely affected by continuous exposure to fluridone concentrations of 0.5 mg/L or less for 60 days after hatching.

Fluridone was detected in orchardgrass and alfalfa at concentrations of 0.11 and 0.07 ppm, respectively, following irrigation of 26 associated crops with water containing fluridone(1). The detection limit for fluridone in this study was 0.05 ppm(1).

Fluridone

Ocular

8 x 10 ^-2 mg/kg-day

Koc values for fluridone measured in 6 soils were reported to range from 350 to 2,462(1-3). According to a classification scheme(4), these Koc values suggest that fluridone is expected to have low to slight mobility in soil. The pKa of fluridone is 12.3(5), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(6).

AEROBIC: A half-life of 12 months was reported for fluridone in sediment under laboratory conditions and 17 weeks under field conditions(1). Fluridone was reported to dissipate with average half-lives of 20 days and 3 months in pond water and in pond hydrosoil, respectively(2). A half-life of 4 days was observed for fluridone after treatment in a pond(3). A half-life of 1 year or more was observed for fluridone in hydrosoils(3). Photodegradation was found to be the major degradation pathway of fluridone in aquatic systems under actual-use conditions(1). In field studies using different soil types, <10% of the originally applied fluridone was found after 220 days in Miller clay and 20% was found remaining after 385 days in Lufkin fine sandy loam soil(4). In laboratory studies, fluridone persistence in non-sterilized soils after 210 days was 62, 44, 10, and 5% in Lufkin fine sandy loam, Miller clay, Hidalgo sandy clay loam, and Brennan fine sandy loam, respectively(4). In Miller clay and Lufkin fine sandy loam no difference was observed in the rate of fluridone degradation between sterilized and non-sterilized samples; however, noticeable differences in degradation were observed between sterilized and non-sterilized Brennan fine sandy loam and Hidalgo sandy clay loam(4). A half-life of 360 days was reported in aerobic soil(5).

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 112900; Type of Pesticide: conventional - herbicide; Use Site: aquatic/non-food; Year: 1986.

The major metabolites were a variety of polar and non-polar compounds resulting from aromatic hydroxylations and heteroaromatic N-demethylation. The parent compound was the primary fecal component over the 1st 72 hr.

Most of the radioactivity was found to be in the form of fluridone or 4-hydroxyfluridone (1-methyl-3-(4-hydroxyphenyl)-5-(3-trifluoromethyl phenyl)-4(1H)-pyridinone) ... in tissues of fish exposed to /fluridone/ ...

/In a rat metabolism study/... Preliminary study: Group A, 2 male (M)/2 female (F) exposed to a single oral dose of [14C]fluridone (...radiopurity 99.8%; for test solutions [14C]fluridone was mixed w/[12C]fluridone, ...100% purity; test substance was suspended in 1% sodium carboxymethyl cellulose [CMC]) at ~10 mg/kg. Group B, 1M/1F exposed to a single oral dose at ~1000 mg/kg. Urine, feces and cage rinses were collected daily for 7 days (because expired (trapped) 14CO2 accounted for <1% of the dose after 24 hr, further 14CO2 measurements were discontinued). Definitive study: Group C, vehicle controls, 2M/2F exposed to a single oral dose of 1% CMC. Group D, 5M/5F exposed to a single oral dose at ~7.4 mg/kg. Group E, 7M/7F exposed to ~10 mg/kg unlabeled fluridone once daily for 14 days, then 5M/5F exposed on day 15 to ~10 mg/kg [14C]fluridone. Group F, 5M/5F exposed to a single oral dose at ~900 mg/kg. ...Clinical signs (lack of mobility, abnormal and rapid head movement, squinting, loss of balance and cage biting) occurred only at the HD (Groups B and F), clearing within 24 hr. Results, Group A: by 7 days, 12.52%/12.89% (M/F) was excreted in urine and 72.76%/81.79% in feces. Group B: by 7 days 4.83%/3.43% was excreted in urine and 86.43%/86.31% in feces. Group D: by 24 hr 11.14%/10.44% was excreted in urine and 72.46%/77.72% in feces. By 7 days 11.61%/10.93% was excreted in urine and 79.19%/84.62% in feces. Combined excretion (including cage rinse) by 7 days was 92.93%/98.74%. Group E: by 24 hr 9.54%/8.51% was excreted in urine and 70.69%/69.90% in feces. By 7 days 10.11%/9.14% was excreted in urine and 79.80%/81.79% in feces. Combined excretion (including cage rinse) by 7 days was 92.81%/94.21%. Group F: by 24 hr 2.40%/2.43% was excreted in urine and 27.16%/27.18% in feces (thus, a relative delay in fecal excretion at the HD). By 7 days 8.30%/8.07% was excreted in urine and 91.58%/90.09% in feces. Combined excretion (including cage rinse) by 7 days was 101.02%/99.62%. Total tissue residues were always <1% of the dose (Groups D-F). Under all conditions, highest tissue levels occurred in the liver. The major metabolites were a variety of polar and non-polar compounds resulting from aromatic hydroxylations and heteroaromatic N-demethylation. The parent compound was the primary fecal component over the 1st 72 hr.

In a metabolism study in rats, fluridone was rapidly and almost completely absorbed into the systemic circulation and eliminated in both the male and female rats within 3 days. The total radioactivity recovered within 3 days after dosing in the urine and feces were 78-90% and 87- 97% of administered dose in males and females, respectively. The majority (approximately 70%) of the radioactivity was eliminated via feces. No tissue accumulation was observed.

The rates of uptake of ... (14C) fluridone (1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-(1H)-pyridinone) from water by rainbow trout and Chironomus tentans (4th Instar) larvae were much lower than those for more hydrophobic compounds tested under similar conditions ... Uptake and clearance of fluridone ... by chironomid larvae were more rapid than for rainbow trout. /BCF/ for chironomid larvae /was/ estimated to be 128 for fluridone ... Liver, intestine, and pyloric caeca of adult rainbow trout accumulated the highest residues of (14C)-fluridone ... Most of the radioactivity was found to be in the form of fluridone or 4-hydroxyfluridone (1-methyl-3-(4-hydroxyphenyl)-5-(3-trifluoromethyl phenyl)-4(1H)-pyridinone) ... in tissues of fish exposed to /fluridone/ ...

Used as an systemic herbicide for control of aquatic weeds in ponds and lakes; No direct food uses; [Reference #1]

Farming (Pesticides) [Category: Industry]

For fluridone (USEPA/OPP Pesticide Code: 112900) 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./

Used as an aquatic herbicide for control of most submerged and emerged aquatic plants (including Utricularia spp., Ceratophyllum demersum, Elodea canadensis, Myriophyllum spp., Najas guadalupensis, Potamogeton spp., Hydrilla verticillata and Panicum purpurascens) in ponds, lakes, reservoirs, irrigation ditches, etc. Application rates depend on target weeds and also the desired selectivity; for ponds a concentration of 45-90 ppb; for lakes and reservoirs 10-90 ppb. Maximum total application to a single body of water 150 ppb per annual growth cycle.

Formulations: Aqueous suspension, pellets.

Trade Name: Avast, Sonar

4(1H)-Pyridinone, 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-: ACTIVE

Cotton is the only crop which has been found to be tolerant.

It is particularly useful for the control of eurasian milfoil in the northern tier states and for hydrilla in the southern states. It inhibits carotene synthesis which causes the loss of chlorophyll. It is typically applied to the whole water body because it requires a contact time of 45 days to be effective. The labels permit single treatments of up to 90 ppb for whole lake treatments and 150 ppb for partial lake treatments, with a maximum cumulative application of 150 ppb per growth cycle. If the treatment area is within 1/4 mile of a water intake, the fluridone concentration must be maintained below 20 ppb.