플루오메튜론

PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compounds

PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008

Pesticides

Pesticide -> EPA IRIS

Herbicides

Active substance -> EU Pesticides database: Approved

Pesticides -> Herbicides, Urea Derivative

Pesticide

log Kow= 2.42

2.42

White crystals

Colorless crystals

less than 1 mg/mL at 70.7 °F (NTP, 1992)

Sol in N,N-dimethylformamide, acetone, ethanol, isopropanol, and other org solvents

Sol (20 °C): 23 g/l dichloromethane; 170 mg/l hexane; 110 g/l methanol; 22 g/l octan-1-ol.

Solubility in acetone: 3 ppm

110 mg/l @ 22 °C

325 to 328 °F (NTP, 1992)

163-164.5 °C

MP: ABOUT 155 °C; NONCORROSIVE /TECHNICAL PRODUCT/

5e-07 mmHg at 68 °F (NTP, 1992)

0.00000094 [mmHg]

9.38X10-7 mm Hg @ 25 °C

This chemical does not meet GHS hazard criteria for 1.3% (3 of 239) of reports.

Warning

H302 (18.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 239 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Commission Regulation (EC) No 33/2008

2011/57/EU, Reg. (EU) 2020/2007, Reg. (EU) 2024/1206, Reg. (EU) No 2018/1266, Reg. (EU) No 540/2011

Status: Active Update: 22-12-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/16818

Urea, N,N-dimethyl-N'-[3-(trifluoromethyl)phenyl]-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Urea-derived herbicides have low toxicity in animal feeding studies; May induce methemoglobinemia; [HSDB] Systemic toxicity unlikely unless large amounts ingested; [EPA Pesticides, p. 122] May decompose on exposure to moisture; An irritant; [MSDSonline]

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Fluometuron is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0049; Pesticide type: herbicide; Registration Standard Date: 12/17/85; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Fluometuron; Data Call-in (DCI) Date(s): 09/11/91, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

A tolerance is established for negligible residues of the herbicide fluometuron (1,1-dimethyl-3-(alpha, alpha, alpha-trifluoro-m-toly)urea) in or on the following raw agricultural commodity: cotton, undelinted seed.

FLUOMETURON is a trifluoromethyl urea derivative. May react with hypochlorites to form nitrogen trichloride which explodes spontaneously in air [J. Am. Chem. Soc. 63:3530-32]. May reacts with azo and diazo compounds to generate toxic gases. Reacts with strong reducing agents to form flammable gases.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

SAFETY PRECAUTIONS FOR HANDLING & APPLICATION: (A) KEEP OUT OF REACH OF CHILDREN & DOMESTIC ANIMALS, (B) MAY BE HARMFUL IF SWALLOWED, (C) AVOID INHALING DUST; DUST MAY BE IRRITATING TO THE EYE, & (D) WASH HANDS WITH SOAP & WATER BEFORE EATING, DRINKING OR SMOKING.

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.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

LC50 Salmo gairdneri (Rainbow trout) 3.0 mg/l/96 hr @ 12 °C (95% confidence interval 2.0- 4.5 mg/l), wt 0.7 g. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l.

LC50 Ictalurus punctatus (Channel catfish) 0.6 mg/l/96 hr @ 18 °C (95% confidence interval 0.3-1.3 mg/l), wt 0.8 g. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l.

LD50 Anas platyrhynchos (Mallard) oral >2000 mg/kg

TERRESTRIAL FATE: IT IS OF INTERMEDIATE PERSISTENCE WITH A HALF-LIFE OF 60-75 DAYS ACCORDING TO SOIL CONDITIONS.

Terrestrial Fate: Fluometuron decreased from 6 ppm to < 0.5 ppm in approximately 165 days in the 0 to 5 cm layer of a plant-free Swiss clay loam under field conditions. Soil compostion: 18% clay, 12% silt, 67% sand, < 1% humus; pH 5.7. Herbicide applied at the rate of 4 kg active ingredient/ha. /From figure/

TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values ranging from 29 to 173(2-7), indicates that fluometuron is expected to have very high to moderate mobility in soil(SRC). Volatilization of fluometuron from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.6X10-9 atm-cu m/mole(8). Fluometuron is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.38X10-7 mm Hg(9). Biodegradation will be the major process by which fluometuron will be lost from most soils(5). Depending on the nature of soil and climatic conditions, the field half-lives of fluometuron in soil ranged from 10-171 days(5,10-12) with an average half-life of 85 days(7). Some loss of fluometuron from soil surface may occur as a result of photolysis by sunlight(13). The photolysis half-life was 9.7 days on a sandy loam soil at 10 to 36 °C under natural light; the major photolysis product was the mono-N-demthylated metabolite [N-methyl-N'-[3-(trifluoromethyl)phenyl]urea](13). Based on its slow rate of hydrolysis in water (half-lives ranging from 2.4 to 2.8 years)(10), hydrolysis of fluometuron in moist soil is not expected to be important(SRC).

TERRESTRIAL FATE: Fluometuron residues often dissipate to nondetectable levels by four months after application of labeled rates. Half-lives in dissipation studies conducted in cotton fields and sampling at 0 to 15 cm were: 103 days for a loamy sand with 0.9% organic matter and pH 6.4 in Georgia; and 171 days for a sandy loam with 1.3% organic matter and pH 7.3 in California(1). Application rate and weather conditions can significantly impact half-life. In field experiments conducted in cotton grown in Georgia and California, no quantifiable fluometuron residues (limit of detection = 10 ppb) were found below 30 cm (12 inches)(1). Volatilization of fluometuron is negligible(1).

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

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=2164-17-2]

Fluometuron

1.3 x 10 ^-2 mg/kg-day

Medical Testing: If symptoms develop or overexposure is suspected, the following may be useful: Liver function tests. Complete blood count. Evaluation by a qualified allergist, including careful exposure history and special testing, may help diagnose skin allergy. Any evaluation should include a careful history of past and present symptoms with an exam. Medical tests that look for damage already done are not a substitute for controlling exposure.

Experimental Koc values for fluometuron in soil range from 29 to 173(1-6). This range of the Koc values indicate that fluometuron would have very high to moderate mobility in soil(7). Soil thin layer chromatography studies confirm that fluormeturon adsorbs weakly to moderately to soil based on experimental Rf values determined in 13 soils (organic matter 0.36-10.26%) ranging from 0.17 to 0.89(8-10). The Koc for fluometuron ranges from 29 to 200 for various soil types (including sandy and loam soils)(11). It is moderately leachable in all but very sandy soils; the Koc value range from 31 to 117 (8 soil types); Kd = 0.15 to 1.13(12). The adsorption of fluometuron increases with increases in organic content(13,14) and clay content of soil(14).

... Mild cholinesterase inhibitor & /causes/ ... an increased leukocyte count in circulating blood in exposed agricultural workers.

No data on humans was available. No evaluation of the carcinogenicity of fluormeturon in humans can be made. ... No data on humans was available.

A frequency of 5.8% of aberrant metaphases was observed in peripheral leukocytes from sowers exposed to an air concn of 4.28-10.90 mg/cu m of a commercial fluometron; a frequency of 4.3% was seen in leukocytes of tractor drivers exposed to concn or 0.64-7.4 mg/cu m, compared with 2.5 % prior to exposure.

DUST MAY BE IRRITATING TO THE EYE ... .

The 3-trifluoromethyl moiety of fluometuron seems to be accessible to some extent to biochemical transformation reactions. A slight but measurable amount of radioactivity (< 5% of the dose applied) evolved as carbon dioxide during the 52 day observation period on incubation of the (14)C trifluoromethyl-labeled herbicide in soils. Oxidation of the trifluoromethyl carbon represents a minor pathway of degradation for fluometuron in the soil.

THE PATHWAY OF DEGRADATION OF FLUOMETURON IN A SANDY LOAM SOIL INVOLVED 2 STEP DEALKYLATION ... FOLLOWED BY HYDROLYSIS TO FORM ANILINE DERIVATIVE ... SOME ... (14)CO2 WAS OBSERVED. MONO- AND DI-DEMETHYL COMPD ... /AND/ ANILINE PRODUCT WERE OBSERVED.

After 35 days incubation, Rhizoctonia solani degraded 88% of (14)C- fluometuron to polar and water-soluble metabolites. No (14)CO2 was observed. Two major metabolites were identified by TLC and UV as 1-methyl-3-(3-trifluoromethylphenyl)urea and 3-trifluoromethylphenylurea. Five other metabolites were not identified.

AEROBIC: Several pure cultures of microorganisms degrade fluometuron(1-2). The biodegradation proceeds by two successive dealkylation to the corresponding 3-(trifluoromethylphenyl) urea which then hydrolyze to the corresponding aniline(1,3). Mixed populations of microorganisms from two soils also metabolized fluometuron in a similar way and the 3-(trifluoromethyl) aniline formed was immediately acetylated to the corresponding acetanilide(4). The release of carbon dioxide observed during the biodegradation of fluometuron(5) may at least be partly the result of the hydrolysis of phenylurea to the aromatic amine and not from ring cleavage(4). The half-life of fluometuron in unsterilized surface soil in the dark was 18 days compared to 315 days in sterilized soil(6). Biodegradation has also been observed in cover crop residues on the soil surface(7). In annual ryegrass, fluometuron was demethylated, at rates similar to those in soils, when the crop had high (78%) moisture conditions(7). The half-life of fluometuron was 189 days for aerobic microbial metabolism in a sandy loam soil at 25 °C(8). The major degradation product under aerobic and anaerobic conditions was mono-N-demethylated fluometuron. Microbial metabolism is the most important contributor to field dissipation, but rates are moderate(8). In soil, microbial degradation is significant and rapid, with continual liberation of carbon dioxide(9).

ANAEROBIC: The half-life of fluometuron was 378 days in a sandy loam soil at 25 °C under anaerobic conditions(1).

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Fluometuron is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0049; Pesticide type: herbicide; Registration Standard Date: 12/17/85; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Fluometuron; Data Call-in (DCI) Date(s): 09/11/91, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

A tolerance is established for negligible residues of the herbicide fluometuron (1,1-dimethyl-3-(alpha, alpha, alpha-trifluoro-m-toly)urea) in or on the following raw agricultural commodity: cotton, undelinted seed.

(FL) FLORIDA 91 ug/l

(ME) MAINE 90 ug/l

... FLUOMETURON WAS METABOLIZED IN VIVO, PRIMARILY BY LIVER, TO N-DESMETHYL & N-DEMETHYLATED ANALOGS ... A SMALL AMT WAS EXCRETED AS ANILINE ANALOG. NO LABELED CO2 WAS DETECTED DURING FIRST 48 HR. AFTER TREATMENT OF CUCUMBERS & COTTON WITH FLUOMETURON, (14)C-METABOLITES WERE DETERMINED BY AUTORADIOGRAPHY. MONOMETHYLATED, DEMETHYLATED, & ANILINE DERIVATIVES WERE IDENTIFIED FROM COTTON. ONLY MONO- & DE-METHYLATED DERIVATIVES WERE IDENTIFIED FROM CUCUMBER.

FLUOMETURON HAS BEEN SHOWN TO UNDERGO A 3 STEP DEGRADATION PROCESS IN PLANTS. THE FIRST TWO STEPS ARE DEMETHYLATION TO A MONOMETHYL THEN TO A DEMETHYLATED INTERMEDIATE. THE THIRD STEP IS DEAMINATION-DECARBOXYLATION STEP THAT PRODUCES AN ANILINE MOLECULE.

Ring hydroxylation of phenylureas in animal tissues ... has been observed with fluometuron.

Cmpd that are rapidly translocated to aerial parts, such as ... fluometuron ... would be expected to be metabolized in the leaves.

For more Metabolism/Metabolites (Complete) data for FLUOMETURON (9 total), please visit the HSDB record page.

... UPTAKE BY ROOTS & TRANSLOCATION TO AERIAL PARTS OF (14)C-LABELED ... FLUOMETURON IN FRENCH DWARF BEAN SEEDLINGS, CULTURED IN NUTRIENT SOLN SUPPLIED WITH 2.5 PPM (AND EQUAL CONCN OF RADIOACTIVITY) OF ... HERBICIDE /WAS STUDIED/. ... FLUOMETURON ... /WAS/ RAPIDLY TRANSLOCATED INTO LEAVES. IN CONTRAST /TO BEING/ ... CONFINED TO TRACHEAL VEINS, FLUOMETURON HAD ALMOST COMPLETELY MOVED OUT INTO THE MESOPHYLL TISSUES.

FLUOMETURON IS MORE READILY ABSORBED BY ROOTS FROM SOIL APPLICATION THAN FROM FOLIAR APPLICATION. FOLIAR ABSORPTION IS AIDED BY ADDING SURFACTANT OR NONPHYTOTOXIC OIL TO SPRAY SOLN. ... TRANSLOCATION OF ROOT ABSORBED. ... IS VIA APOPLAST TO UPPER PLANT PARTS. FOLIAR APPLICATIONS ARE ALSO TRANSLOCATED IN APOPLAST ... .

Herbicide for control of many broadleaf and grass species; [HSDB]

Farming (Pesticides) [Category: Industry]

For Fluometuron (USEPA/OPP Pesticide Code: 035503) 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./

For control of many broadleaf and grass species.

FLUOMETURON IS ... ESPECIALLY SUITABLE FOR CONTROL OF ANNUAL BROAD-LEAVED AND GRASS WEEDS OF COTTON AT 1.6-2.7 KG ACTIVE INGREDIENT/HECTARE; ALSO AS PRE- AND POST-EMERGENCE SPRAYS ON SUGAR CANE, PINEAPPLE AND COFFEE AT RATES OF 3-4 LB ACTIVE INGREDIENT/ACRE. ... HERBICIDAL PROPERTIES ARE SHARED BY THE 4-TRIFLUOROMETHYL DERIVATIVE BUT NOT BY N'3,5-BIS(TRIFLUOROMETHYL)PHENYL-N,N-DIMETHYLUREA.

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

100% AS AN HERBICIDE ON COTTON (1975)

4,500,857 lbs applied on cotton in 1992.

REACTION OF PHOSGENE WITH M-TRIFLUOROMETHYLANILINE TO PRODUCE M-TRIFLUOROMETHYLPHENYL ISOCYANATE, FOLLOWED BY REACTION OF THIS WITH DIMETHYLAMINE

Made by the reaction of dimethylamine on 3-trifluoromethylphenyl isocyanate.

m-aminobenzotrifluoride + dimethylcarbonyl chloride (dehydrochlorination)

USEPA/OPP Pesticide Code 035503; Trade Names: Cotoran; C-2059; Lanex; Cottonex.

Fluometuron can be used preplant incorporated at 1.8 kg ai/ha (1.6 lb ai/A) and PRE or POST at 1.12-2.24 kg ai/ha (1-2 kb ai/A) ... It can be applied in water or liquid fertilizer.

50% & 80% WETTABLE POWDERS

TECHNICAL PRODUCT IS ABOUT 96% PURITY.

For more Formulations/Preparations (Complete) data for FLUOMETURON (7 total), please visit the HSDB record page.

Urea, N,N-dimethyl-N'-[3-(trifluoromethyl)phenyl]-: ACTIVE

COMPATIBLE WITH OTHER HERBICIDES.

COMBINATION OF ... LOW MAMMALIAN TOXICITY & BIODEGRADABILITY /OF PHENYLUREA HERBICIDES/ LEADS TO CONCLUSION THAT THESE CMPD ARE NOT SIGNIFICANT FACTORS IN CONTAMINATION OF SOIL & WATER SYSTEMS, & THEIR SIGNIFICANCE AS ENVIRONMENTAL POLLUTANTS SEEMS TO BE MINIMAL. /PHENYLUREA HERBICIDES/