Fluvalinate

502.9 g/mol

502.91

364G5G03VC

2902

DTXSID7024110

Yellow-amber liquid

71.4 Ų

log Kow = 7.02|log Kow: 5.50 (HPLC measurement)

1.29 g/cm³ @ Temp: 25 °C

<25 °C

>450 °C

Index of refraction: 1.549 at 20 °C/D

6.29e-09 M|Solubility in water, 0.012 mg/L at 25 °C /tau-Fluvalinate/|Solubility in water: 2.0 ppb; sol in organic solvents|In water, <0.005 mg/kg|In water at 20 °C (98.6% purity): distilled water: 1.12 ug/L; pH 4: <0.35-0.56 ug/L; pH 7: 1.03 ug/L; pH 9: not stable|Freely soluble in alcohols, aromatic hydrocarbons, dichloromethane, diethyl ether|At 25 °C (91.6% purity): >500g/L in acetone, ethyl acetate, methanol, octanol, dichloromethane and toluene

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. /Tau-fluvalinate/

Vapor pressure: <0.013 mPa (<1X10-7 mm Hg) at 25 °C|Vapor pressure at 20 °C (99.0% purity): 9.0X10-11 Pa, extrapolated|8.42X10-9 mm Hg at 25 °C

Henry's Law constant = 1.18X10-9 atm-cu m/mol at about 25 °C

No pKa found between pH 2.11-11.1 (99.5% purity)

log Kow = 4.26 at 25 °C. Density: 1.262 at 25 °C. Solubility: in water, 1.03 ppb (pH 7, 20 °C); soluble in toluene, acetonitrile, isopropanol, DMF, n-octanol; in iso-octane 108 g/L. /tau-Fluvalinate/|Decomposition point: 350 °C /Tau-fluvalinate/

Insoluble in water.

Amines, Phosphines, and Pyridines

FLUVALINATE is a trifluoromethyl pyrethroid. May react with acids to liberate heat. Strong oxidizing acids may cause a reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated in contact with caustic solutions. Flammable or toxic gases may be generated by mixing with alkali metals and hydrides.

Non-corrosive to slightly corrosive, depending upon the metal.

Stable for at least 1 year at temperatures up to 50 °C. Decreased stability under alkaline conditions. /Technical fluvalinate/|On hydrolysis 50% loss occurs: at 25 °C in 30 days (pH3 and pH6), 1-2 hr (pH9); at 42 °C in 35 days (pH3), 8 days (pH6), and 1 day (pH9). It is stable in glass > 1.5 years at 42 °C. In sunlight thin films on glass or silica gel suffered 50% loss in ca 2 days, an aqueous emulsion (1.6 g/l) in glass in 12 days. In sandy loam under aerobic conditions 50% loss occurs in about a day.

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.|The following wastewater treatment technology has been investigated for chlorinated pesticides: Concentration process: Resin adsorption. /Chlorinated pesticides/

Conditions to avoid: Heat, flames and sparks. Incompatible materials: Strong oxidizing agents. /Tau-fluvalinate/|Incompatible with alkaline materials.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Tau-Fluvalinate (September 2005). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of June 6, 2014: http://www.epa.gov/pesticides/reregistration/status.htm]

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. (ERG, 2016)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P271, P273, P284, P301+P310, P304+P340, P307+P311, P309+P311, P310, P314, P320, P321, P330, P391, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P320, P321, P330, P332+P313, P337+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, and P501|P210, P260, P264, P270, P271, P280, P284, P301+P310, P304+P340, P305+P351+P338, P307+P311, P310, P314, P320, P321, P330, P332+P313, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|Chemical-resistant gloves. ... Protective eyewear. /Tau-fluvalinate/|Employees should be provided with and required to use dust- and splash-proof safety goggles where /pyrethroids/ ... may contact the eyes. /Pyrethroids/|Employees should be provided with and be required to use impervious clothing, gloves, and face shields (eight-inch minimum). /Pyrethroids/|Body Protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. /Tau-fluvalinate/|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). /Tau-fluvalinate/

Use water spray to cool unopened containers. /Tau-fluvalinate/|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. /Tau-fluvalinate/|Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. /Tau-fluvalinate/

Wear respiratory protection and rubber gloves when opening drum and pouring (trace quantities of hydrogen cyanide may be present).|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.|SRP: Contaminated protective clothing should be segregated in a manner such that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|Long-sleeved shirt and long pants ... Shoes plus socks. /Tau-fluvalinate/

The chief effect from exposure ... is skin rash particularly on moist areas of the skin. ... May irritate the eyes. /Pyrethroids/

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 5 mg/cu m. Skin Designation. /Cyanides, as CN/

tau-Fluvalinate was detected in agricultural field drain samples collected in California in 2008 at a concentration of 7 ng/L (all associated with the sediment in the drain water)(1).

IDENTIFICATION AND USE: Fluvalinate is a yellow-amber liquid. It is a broad-spectrum insecticide/miticide in the pyrethroid class of pesticides. Fluvalinate is registered for a single food use (beehives/honey) and several non-food uses, including ornamentals (outdoor and container-grown, greenhouse, interior plantscapes, dip for cuttings), building surfaces/perimeters, ant mounds and certain crops (carrots and brassica/cole crops) grown for seed. 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. Tau-fluvalinate is one form of racemic fluvalinate, which consists of four active diastereoisomers. The product was initially registered under the name "Fluvalinate," and all four diastereoisomers were used in the product formulation. Later, chemical advances altered the product to include only the two diastereoisomers found to be insecticidally active. HUMAN EXPOSURE AND TOXICITY: Workers exposed to fluvalinate have reported coughing, sneezing, throat irritation, itching or burning sensations on the arms or face with or without a rash, headache, and nausea. None of the fluvalinate exposures reported to the Poison Control Centers in nine years resulted in major or fatal outcome and none of the cases required hospitalization or critical care. ANIMAL STUDIES: Tau-fluvalinate caused slight conjunctival discharge observed one hour post instillation in rabbit eyes. Conjunctival swelling and redness noted for up to three days. In dogs 50 mg/kg/day of fluvalinate technical for 6 months induced emesis, loose stools, dehydration, and neurologic abnormalities. Fluvalinate technical (racemic) 93.8% administered to rats produced maternal and fetal toxicity at 50 mg/kg/day (decreased maternal and fetal weight, delayed ossification, decreased viability). Fluvalinate, at dose rates of 10.5 and 21 mg/kg (1/10th and 1/5th of LD50, respectively) by ip route in rats, impaired learning, while no such effect on permanent memory was observed. Temporary memory was impaired at lower doses whereas it was completely suppressed at higher dose. However, at both dose levels retrieval of passive avoidance reaction was completely suppressed. In mouse L5178Y TK+/-cells, induction of forward mutations with activation occurred when exposed to fluvalinate. No other genotoxic effects were observed. ECOTOXICITY STUDIES: The acute oral and dietary studies conducted with bobwhite quail and/or mallard ducks indicate that tau-fluvalinate is practically non-toxic to birds. For marine/estuarine fish, treatment-related decreases in the number of eggs produced/female/reproductive day, percent spawning frequency and length of posthatch fish were observed in sheepshead minnows.

/Pyrethroid/ detoxification ... important in flies, may be delayed by the addition of synergists ... organophosphates or carbamates ... to guarantee a lethal effect. ... /Pyrethroid/

LD50 Rat oral 261 mg/kg|LC50 Rat inhalation 439 mg/cu m/4 hr|LD50 Rat ip 105 mg/kg|LD50 Rat dermal >20 g/kg|For more Non-Human Toxicity Values (Complete) data for FLUVALINATE (9 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ The acute oral and dietary studies conducted with bobwhite quail and/or mallard ducks indicate that tau-fluvalinate is practically non-toxic to birds. The acute LD50 values from the two bobwhite quail oral studies are both >2510 mg/kg. Both studies had some mortalities. Sublethal effects consisted mainly of lethargy; however, lower limb weakness was also observed in one study at a higher dose level. The acute LC50 values from one bobwhite quail dietary study and both mallard duck dietary studies are all >5620 mg/kg. Sublethal effects consisted mainly of reduced body weight gain and food consumption at higher concentration levels. The acute LC50 from a second bobwhite quail dietary study is 5627 mg/kg. Mortality and sublethal effects were observed at the same concentration levels. /Tau-fluvalinate/|/AQUATIC SPECIES/ For marine/estuarine fish, treatment-related decreases in the number of eggs produced/female/reproductive day, percent spawning frequency and length of posthatch fish were observed in sheepshead minnows at the LOAEC of 0.070 ug a.i./L and a NOAEC of 0.036 ug a.i./L. The most significant effect observed at 0.070 ug a.i./L was reduced length of posthatch fish at day 28. At the highest concentration level (0.14 ug a.i./L), lethargy in fish and larvae were also observed. /Tau-fluvalinate/|/AQUATIC SPECIES/ Sublethal effects in freshwater invertebrates following acute exposure include a decrease in size, lethargy and swimming erratically. The lowest concentration where sublethal effects (swimming erratically and lethargy in daphnia) were observed is 0.06 ug/L. Decrease in size was observed at 0.24 ug/L. The 1 in 10 year peak EEC /(estimated environmental concentration)/ values for carrots and ornamentals are estimated to be 0.46 and 0.25 ppb, respectively. Therefore, under both these scenarios, sublethal effects (decreases in size, swimming erratically and lethargy) are likely for freshwater invertebrates. These effects place the animals at risk for reproductive capacity (decrease in size may affect attracting a mate, fertility and other factors) and survival (predation). In addition, the decrease in size may affect the food chain because the predators will have to eat more individuals in order to meet their nutritional requirements. Lethargy was observed at nominal concentrations of 0.018 ug/L and above in mysid shrimp following acute exposure. These effects are seen at concentrations well below the estimated 1 in 10 year peak EECs for both the carrot and ornamental scenarios and are highly likely. Lethargy will place the animals at risk for predation. /Tau-fluvalinate/|/FIELD STUDIES/ A minicosm study was conducted in 3 x 8 x 2 ft. ponds (740 L over 10 cm of biologically active sediment per pond). Ponds were only stocked with 16 Bluegill sunfish (Lepomis macrochirus) per pond. All other biota were allowed to succeed from the area surrounding the ponds and the natural reservoir pond water and biologically active hydrosoil spikes. Three formulations of fluvalinate were tested...: Mavrik Aquaflow (23.0% half-resolved fluvalinate), a formulation containing 22.2% fully resolved fluvalinate and a formulation containing 22.2% microencapsulated half-resolved fluvalinate, respectively. ...Following application, mean-measured fluvalinate concentrations in the minicosm water ranged from 0.13 to 0.31 ppb a.i with half-lives ranging from 9.8 to 47.0 for the formulations, the longest half-life from a microencapsulated formulation. Mean-measured fluvalinate concentrations in the minicosm sediment ranged from 1.11 to 3.68 ppb a.i.. ...Neither phytoplankton nor fish were affected by treatment. For both, the NOAEC is 0.31 ppb, the highest concentration measured. Effects on zooplankton (decreased abundance of both life stages of copepods) and benthic macroinvertebrates (decreased abundance of caenidae (Mayflies)) were observed at all formulation application rates. Some of these effects were difficult to interpret because of the confounding effect of seasonal fluctuations in abundance. Therefore, the overall NOAEC is <0.13 ppb, the lowest noted concentration. Since formulations B and C were only applied at the 0.15 lb a.i./A rate and the water and sediment tau-fluvalinate concentration values were only measured for the 0.15 and 0.30 lb a.i./A rates, a comparison of the toxicities between the formulations could not be done except for at the one 0.15 lb a.i./A rate. At that rate, the NOAEC/LOAEC values for the various formulations did not appear to be significantly different. Therefore, the reported NOAEC/LOAEC values represent all the formulations tested. /Tau-fluvalinate/

Fluvalinate's production may result in its release to the environment through various waste streams; its use as an insecticide(1) will result in its direct release to the environment(SRC). Fluvinate consists of four isomers. The present commercial insecticide is named tau-fluvalinate and contains the two isomers found to be active insecticides(2).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 1.1X10+5 to 1X10+6(2,3), indicate that fluvalinate is expected to be immobile in soil(SRC). Volatilization of fluvalinate from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.18X10-9 atm-cu m/mole(4). Fluvalinate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.42X10-9 mm Hg at 25 °C(5). Laboratory tests have shown that fluvalinate photodegrades readily on glass, soil and plant surfaces exposed to sunlight(6). The photolysis half-life on soil surfaces is reported as 13-18 days(7,8). The aqueous hydrolysis half-lives of tau-fluvalinate at 20 °C are reported as 48, 22.5 and 1.25 days at pH 5, 7 and 9, respectively(4) which suggests that abiotic hydrolysis may have some environmental importance in moist soils, especially alkaline soils(SRC). A laboratory study using a sandy loam, clay and clay loam soils observed half-lives of 6-8 days under aerobic conditions and about 15 days under anaerobic conditions(9); the evolution of CO2 and analogy to work on similar insecticides suggested that a measurable portion of the degradation was occurring microbially(9). Soil mineralization tests have also indicated that biodegradation is a major degradation pathway in soil(4). Laboratory soil studies under aerobic conditions have observed dissipation half-lives of 12-92 days(8). A geometric mean aerobic laboratory half-life of 40.7 days is reported(4). An anaerobic laboratory soil half-life of 86 days is reported(3). A field study measured fluvalinate half-lives of 6.8-8.0 days in one agricultural soil(10). Field studies in Spain and Germany noted half-lives of 1.64-8.95 days(4). A field study in California on bare ground observed a half-life of 63 days(3). Half-lives ranging from 1 to 1.7 days were reported from experiments to determine the persistence of fluvalinate on chili (Capsicum annuum L.) foliage, fruit, and cropped-soil(11).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 1.1X10+5 to 1X10+6(2,3), indicate that fluvalinate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 1.18X10-9 atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 14000(SRC), from its log Kow of 7.02(5) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). Based on available data, a review panel concluded that an approximated BCF of 1979 was appropriate for tau-fluvalinate(5). Fluvalinate has been reported to be non-bioaccumulative based on tests with Bluegill sunfish (Lepomis macrochirus)(8). Fluvalinate is expected to degrade in water through hydrolysis, biodegradation and photodegradation(SRC). The aqueous hydrolysis half-lives of tau-fluvalinate at 20 °C are reported as 48, 22.5 and 1.25 days at pH 5, 7 and 9(5), respectively, which suggests that abiotic hydrolysis may have some environmental importance, especially in alkaline waters(SRC). Laboratory tests have shown that fluvalinate photodegrades rapidly (half-life of 1 day) in aqueous solutions (in Erlenmeyer flasks) exposed to sunlight(9). In aqueous solution, the photolytic degradation half-life of tau-fluvalinate is reported as 4 days under summer sunlight conditions at 40 deg N latitude(5). Results of soil degradation studies suggest that fluvalinate will degrade microbially(5,10), although tau-fluvalinate is reported as not readily biodegradable(5). An aquatic anaerobic metabolism study noted a tau-fluvalinate half-life of 84.2-88.3 days(5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluvalinate, which has a vapor pressure of 8.42X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase fluvalinate may be removed from the air by wet or dry deposition(SRC). Tau-fluvalinate absorbs at wavelengths >290 nm and is susceptible to direct photolysis in sunlight(3).

Aqueous hydrolysis half-lives for a 9 ppb solution of tau-fluvalinate at 25 °C were reported as 48 days at pH 5, 38.5 days at pH 7 and 1.1 days at pH 9(1). The aqueous stability of fluvalinate at 25 °C is reported as 30 days at pH 3 and pH 6, and 1-2 hours at pH 9(2); at 42 °C, the aqueous stability is reported as 35 days at pH 3, 8 days at pH 6, and 1 day at pH 9(1). The hydrolytic half-lives of tau-fluvalinate at 20 °C are reported as 48, 22.5 and 1.25 days at pH 5, 7 and 9, respectively(3). The hydrolytic metabolites include 3-phenoxybenzaldehyde, 3-phenoxybenzoic acid and anilino acid(3). Tau-fluvalinate absorbs at wavelengths >290 nm and is susceptible to direct photolysis in sunlight(3). In aqueous solution, the photolytic degradation half-life of tau-fluvalinate is reported as 4 days under summer sunlight conditions at 40 deg N latitude(3). A photodegradation study in aqueous solution and as thin films on glass and soil found fluvalinate to readily photodegrade in sunlight; the photodegradation half-life (as a thin-film or as an aqueous solution in a 100 mL Erlenmeyer flask) was about 1 day of sunlight exposure(4). Photodegradation products included 3-phenoxybenzaldehyde and its corresponding acid, a formanilide, an oxamic acid, (3-phenoxyphenyl)acetonitrile, the cyanohydrin of 3-phenoxybenzaldehyde, and the anilino acid derivative of fluvalinate(4). The photodegradation half-life of tau-fluvalinate on a soil surface exposed to sunlight is reported as 13 days(1). The photodegradation half-life of fluvalinate on a soil surface exposed to sunlight is reported as 18 days(5).

An estimated BCF of 14000 was calculated in fish for fluvalinate(SRC), using a log Kow of 7.02(1) and a regression-derived equation(2). Based on available data, a review panel concluded that an approximated BCF of 1979 was appropriate for tau-fluvalinate(1). According to a classification scheme(3), these BCF values suggest the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC). Fluvalinate has been reported to be non-bioaccumulative based on BCF values of 120, 660, and 360 for the edible, non-edible and whole fish tissues in a study with Bluegill sunfish (Lepomis macrochirus)(4).

5.07e+05 L/kg|Measured Koc values ranging from 1.1X10+5 to 1X10+6 have been reported for fluvalinate in various types of soil(1,2). According to a classification scheme(3), these Koc values suggest that fluvalinate is expected to be immobile in soil. In a field study conducted in New Delhi, India, fluvalinate did not leach below a 7.5 cm depth after a 40-day observation period(4). Laboratory sorption studies with soil-water solution found that fluvalinate was rapidly adsorbed to the soil from the water with little desorption(5); also, thin layer chromatography tests classified fluvalinate as immobile in soil(5). A laboratory partitioning study found that a large portion of tau-fluvalinate was associated with suspended sediment (or adsorbed on container walls) as compared to dissolved in the water-phase(6).

The Henry's Law constant for fluvalinate is reported as 1.18X10-9 atm-cu m/mole at about 25 °C(1). This Henry's Law constant indicates that fluvalinate is expected to be essentially nonvolatile from water surfaces(2). Fluvalinate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Fluvalinate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.42X10-9 mm Hg(3).

Pesticide residues were measured in 765 samples of agricultural products (478 domestic and 287 imported) in Hyogo Prefecture, Japan (1995-2000)(1). Fluvalinate was detected 13 times in 291 samples of lettuce; concentrations were <0.5 ug/g(1). Fluvalinate was detected 4 times in 106 samples of Japanese apricot; concentrations were <0.5 ug/g(1). An average fluvalinate concentration of 0.03 ug/g was reported in chickpea samples collected from farms in Delhi, India during 1992-1993(2). Fluvalinate was detected in 39 of 221 honey samples collected from 1988-1991 in Spain; concentrations ranged from 1 to 15 ug/kg, with mean of 2 ug/kg(3). Fluvalinate was detected in 11 of 101 honey samples collected from Galicia (in NW Spain) at levels ranging from 10 to 40 ug/kg(4). Fluvalinate was detected in 3 of 173 local market samples collected in Japan at concentrations of 3.6-5.4 ng/g(5).

Occupational exposure to fluvalinate may occur through inhalation and dermal contact with this compound at workplaces where fluvalinate is produced or used(SRC). The exposure of pesticide applicators in a commercial greenhouse to fluvalinate and other pesticides was measured via exposure pads, handwashes and air samples(1); handwashes indicated a fluvalinate exposure rate of 13-91 ug/hr while air samples measured 0.017-0.046 ug/L(1); clothing pads indicated an overall body accumulation rate (excluding handwashes) of 651-2233 ug/hr(1). Exposures of fluvalinate to drencher workers in the greenhouse were: 92-97 ug/hr handwash, 0.002 ug/L air and 3000 ug/hr overall body accumulation rate(2); when normalized to spray rates, overall body accumulation rate was 125 mg deposited/kg sprayed(2). Exposures of fluvalinate to tractor drivers spraying the pesticide to Florida ornamentals were: 13-17 ug/hr handwash, 0.002 ug/L air and 265 ug/hr overall body accumulation rate(3); when normalized to spray rates, overall body accumulation rate was 39 mg deposited/kg sprayed(3). Occupational exposure to fluvalinate occurs through dermal contact and inhalation of dust and sprays, especially to workers applying the compound as an insecticide(4). The general population may be exposed to tau-fluvalinate via ingestion of food and drinking water and via inhalation of ambient air and dermal contact in the vicinity of tau-fluvalinate being applied and used as an insecticide(5).

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

/Pyrethroids/ readily penetrate insect cuticle as shown by topical LD50 to Periplaneta (cockroach) ... /Pyrethroids/|When radioactive pyrethroid is administered orally to mammals, it is absorbed from intestinal tract of the animals and distributed in every tissue examined. Excretion of radioactivity in rats administered trans-isomer: dosage: 500 mg/kg; interval 20 days; urine 36%; feces 64%; total 100%. /Pyrethroids/|Although limited absorption may account for the low toxicity of some pyrethroids, rapid biodegradation by mammalian liver enzymes (ester hydrolysis and oxidation) is probably the major factor responsible. Most pyrethroid metabolites are promptly excreted, at least in part, by the kidney. /Pyrethroids/|When fluvalinate labeled with (14)C in the acid moiety was admin to rats at 1 mg/kg, (14)C was rapidly excreted into urine (9 to 19%) and feces (75 to 88%) within 4 days after admin. The major (14)C component (45% of the fecal (14)C) was the parent cmpd. Liver showed relatively higher (14)C tissue residue than other tissues, indicating that the (14)C tissue residues from fluvalinate are somewhat different from those of other pyrethroids having the same alcohol moiety ... The major urinary metabolites are anilino acid, its hydroxymethyl derivative, its glycine conjugate, haloaniline, and sulfate conjugate of hydroxyhaloaniline. On the other hand, the major fecal metabolites are anilino acid, its amide derivative, and several conjugates of anilino acid with several endogenous components ...|When (14)C-acid-fluvalinate was admin to rhesus monkeys at 1 mg/kg, the (14)C was excreted into urine (37%) and feces (55%) within 5 days after admin.

The metabolic pathways for the breakdown of the pyrethroids vary little between mammalian species but vary somewhat with structure. ... Essentially, pyrethrum and allethrin are broken down mainly by oxidation of the isobutenyl side chain of the acid moiety and of the unsaturated side chain of the alcohol moiety with ester hydrolysis playing and important part, whereas for the other pyrethroids ester hydrolysis predominates. /Pyrethrum and pyrethroids/|The relative resistance of mammals to the pyrethroids is almost wholly attributable to their ability to hydrolyze the pyrethroids rapidly to their inactive acid and alcohol components, since direct injection into the mammalian CNS leads to a susceptibility similar to that seen in insects. Some additional resistance of homeothermic organisms can also be attributed to the negative temperature coefficient of action of the pyrethroids, which are thus less toxic at mammalian body temperatures, but the major effect is metabolic. Metabolic disposal of the pyrethroids is very rapid, which means that toxicity is high by the intravenous route, moderate by slower oral absorption, and often unmeasureably low by dermal absorption. /Pyrethroids/|Fastest breakdown is seen with primary alcohol esters of trans-substituted acids since they undergo rapid hydrolytic and oxidative attack. For all secondary alcohol esters and for primary alcohol cis-substituted cyclopropanecarboxylates, oxidative attack is predominant. /Pyrethroids/|Pyrethroids are generally metabolized in mammals through ester hydrolysis, oxidation, and conjugation, and there is no tendency to accumulate in tissues. In the environment, synthetic pyrethroids are fairly rapidly degraded in soil and in plants. Ester hydrolysis and oxidation at various sites on the molecule are the major degradation processes. /Pyrethroids/|For more Metabolism/Metabolites (Complete) data for FLUVALINATE (8 total), please visit the HSDB record page.

The elimination half-lives for mammals ranges from 6 to 12 hours.

The pyrethroids are a class of natural and synthetic pesticides which were associated with an epidemic of gynecomastia in Haitian men in 1981. In the present study several pyrethroids were tested for their ability to interact with androgen binding sites in dispersed, intact human genital skin fibroblasts and in human plasma to sex hormone binding globulin (SHBG). All the pyrethroids tested inhibited fibroblast binding of (3H)methyltrienolone (R1881) at 22 degrees C with the following rank order of potency:pyrethrins greater than bioallethrin greater than fenvalerate greater than fenothrin greater than fluvalinate greater than permethrin greater than resmethrin. 50% displacement of (3H)R1881 binding to fibroblast androgen receptors was achieved by 1.5-44 x 10-5 M concentrations of the competitors, respectively. Previous studies with cimetidine, a known inhibitor of androgen receptor binding, showed 50% competition at a concentration of 1.4 X 10-4 M in this system. Scatchard analysis of binding experiments performed with increasing concentrations of (3H)R1881 in the presence of the pyrethroids indicated that the binding inhibition was competitive. On the other hand, of the pyrethroids examined only the pyrethrins (50% inhibition) and bioallethrin (43% inhibition) were able to displace (3H)testosterone from sex hormone binding globulin when tested at a concentration of 1 X 10-4 M. These data indicate that a novel class of non-steroidal compounds, the pyrethroids, can interact competitively with human androgen receptors and sex hormone binding globulin. These findings provide a mechanism by which chronic exposure of humans or animals to pesticides containing these compounds may result in disturbances in endocrine effects relating to androgen action.|The ... pyrethroids delay closure of the sodium channel, resulting in a sodium tail current that is characterized by a slow influx of sodium during the end of depolarization. Apparently the pyrethroid molecule holds the activation gate in the open position. Pyrethroids with an alpha-cyano group (e.g., fenvalerate) produce more prolonged sodium tail currents than do other pyrethroids (e.g., permethrin, bioresmethrin). The former group of pyrethroids causes more cutaneous sensations than the latter. /Pyrethroids/|Interaction with sodium channels is not the only mechanism of action proposed for the pyrethroids. Their effects on the central nervous system have led various workers to suggest actions via antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, or actions on calcium ions. Since neurotransmitter specific pharmacological agents offer only poor or partial protection against poisoning, it is unlikely that one of these effects represents the primary mechanism of action of the pyrethroids, and most neurotransmitter release is secondary to increased sodium entry. /Pyrethroids/|The interaction of a series of pyrethroid insecticides with the sodium channels in myelinated nerve fibers of the clawed frog, Xenopus laevis, was investigated using the voltage clamp technique. Of 11 pyrethroids, 9 insecticidally active cmpd induced a slowly decaying sodium tail current on termination of a step depolarization, whereas the sodium current during depolarization was hardly affected. /Pyrethroids/|For more Mechanism of Action (Complete) data for FLUVALINATE (13 total), please visit the HSDB record page.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Pyrethrins, pyrethroids, and related compounds/|Basic treatment: . Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and treat if necessary... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Pyrethrins, pyrethroids, and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for air way control in the patient who is unconscious or is in severe respiratory distress. Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Pyrethrins, pyrethroids, and related compounds/|Emergency and supportive measures: 1. Treat bronchospasm and anaphylaxis if they occur. 2. Observe patients with a history of large ingestions for at least 4-6 hours for any signs of CNS depression or seizures. /Pyrethrins and pyrethroids/|For more Antidote and Emergency Treatment (Complete) data for FLUVALINATE (10 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Workers exposed to fluvalinate have reported coughing, sneezing, throat irritation, itching or burning sensations on the arms or face with or without a rash, headache, and nausea.|/SIGNS AND SYMPTOMS/ As a type II pyrethroid, tau-fluvalinate causes the "pyrethroid reaction," a specific type of dermal irritation following contact. The "pyrethroid reaction" may be one manifestation of the chemical's ability to act on nerve endings. ... In humans, the pyrethroid reaction is characterized by tingling sensations and/or itching, often severe, upon contact with the chemical. /Tau-fluvalinate/|/SIGNS AND SYMPTOMS/ None of the fluvalinate exposures reported /to the Poison Control Center/ in nine years resulted in major or fatal outcome and none of the cases required hospitalization or critical care. ... In general fluvalinate was as likely to cause minor symptoms as other pesticides but much less likely to cause more serious effects requiring hospitalization or critical care. Symptoms most commonly reported were dermal (rash, irritation, and erythema) and headache with infrequent reports of eye irritation, nausea, vomiting.|/SIGNS AND SYMPTOMS/ An incident occurred in 1992 when the product was used to fog a greenhouse. ... A family of four (3 adults and 1 infant) reported choking, reddened face, sour taste in dry mouth, and involuntary dropping in one household member and transient "passing out" and dry mouth in the infant. Another household member reported choking, difficulty breathing, jumpiness, dropping things, fatigue, and dry mouth. ... People in the immediate vicinity of the greenhouse experienced coughing, nausea, and headaches. The total evacuated was reported as 200, 8 sought medical attention and 17 were treated by paramedics.|For more Human Toxicity Excerpts (Complete) data for FLUVALINATE (6 total), please visit the HSDB record page.

alpha-cyano-3-phenoxybenzyl 2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanoate

Emulsifiable concentrate, suspension concentrate, oil-in-water emulsion.|Mixed formulations: fluvalinate & thiometon|Flowable concentrate and impregnated strips (bee hives). /Tau-fluvalinate/|Tau-fluvalinate is one form of racemic fluvalinate, which consists of four active diastereoisomers. The product was initially registered under the name "Fluvalinate," and all four diastereoisomers were used in the product formulation. Later, chemical advances altered the product to include only the two diastereoisomers found to be insecticidally active, thus rendering a "half-resolved" version. /Tau-fluvalinate/|For more Formulations/Preparations (Complete) data for FLUVALINATE (9 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies fluvalinate as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|Synthetic pyrethroid insecticide without the usual cyclopropane ring.|Compatible with spray oils and most organic solvents.|Two stereoisomers, the D-valinate and the DL-valinate, have been used as insecticides, of which the former has the greater activity, and is the isomer now in general use.|For more General Manufacturing Information (Complete) data for FLUVALINATE (8 total), please visit the HSDB record page.

Analysis of products by reverse-phase high performance liquid chromatography, or by gas liquid chromatography; analysis of residues by gas liquid chromatography with electron capture detector.|Pyrethrins ... in pesticide formulations are analyzed using gas chromatography equipped with flame ionization detection. Average recovery is 98% with a precision of 0.0044-0.011. /Pyrethrins/|... Liquid chromatography method has been developed to quantitate pyrethrins in pesticide formulations. ... Detection was monitored at 240 nm. ... Percent coefficients of variation ranged from 1.39 to 9.68 with the majority less than 5.00. ... /Pyrethrins/|Pyrethrins were detected in soils by gas chromatography after extraction with hexane. /Pyrethrins/|For more Analytic Laboratory Methods (Complete) data for FLUVALINATE (7 total), please visit the HSDB record page.