Fluvalinate

Pesticide -> EPA IRIS

Pesticides -> Pyrethrins/Pyrethroids

Pesticide (Fluvalinate) -> USDA PDB

log Kow = 7.02

log Kow: 5.50 (HPLC measurement)

5.5

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

>450 °C at 760 mm Hg (extrapolated)

Viscous amber oil; moderate or weak sweetish odor. BP: 164 °C at 0.07 mm Hg. Stable for 2 years at room temperature (20-28 °C). Undergoes decomposition on exposure to sunlight. /Technical tau-fluvalinate/

0.0000001 [mmHg]

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

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P271, P273, P284, P301+P316, P304+P340, P308+P316, P316, P319, P320, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Danger

H227: Combustible liquid [Warning Flammable liquids]

Hazard Traits - Developmental Toxicity; Environmental tox

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

A throat irritant; Causes tingling or burning sensation on skin contact; In reported poisoning cases in 9 years, no cases required hospitalization; Commonly reported symptoms are skin irritation and headache; Synthetic pyrethroids can cause tremors, paralysis, and seizures in animals at near lethal doses; [HSDB]

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]

Tolerances are established for residues of the insecticide tau-fluvalinate, cyano-(3-phenoxyphenyl)methyl N-[2-chloro-4-(trifluoromethyl)phenyl]-D-valinate, in or on the following food commodity: honey. /Tau-fluvalinate/

The Agency has completed its assessment of the dietary, residential, occupational, and ecological risk associated with the use of pesticide products containing the active ingredient tau-fluvalinate. Based on a review of these data, the Agency has sufficient information on the human health and ecological effects of tau-fluvalinate to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA.The Agency has determined that tau-fluvalinate-containing products are eligible for reregistration provided that label amendments are made as outlined in Section V. In addition, the Agency intends to require data to confirm some risk conclusions discussed in Section III. ... Based on its evaluation of tau-fluvalinate, the Agency has determined that tau-fluvalinate products, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA and FQPA. Accordingly, should a registrant fail to implement any of the reregistration requirements identified in this document, the Agency may take regulatory action to address the risk concerns from the use of tau-fluvalinate. If all changes outlined in this document are incorporated into the product labels, then all current risks for tau-fluvalinate will be adequately mitigated for the purposes of this determination. /Tau-fluvalinate/

"Fluvalinate" is the common name for the racemic mixture of the 4 isomers of cyano-(3-phenoxyphenyl)methyl N-[2-chloro-4-(trifluoromethyl)phenyl]-valinate (CAS name). "Tau-fluvalinate" is the term for the half resolved mixture (2 of the 4 isomers).

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Fluvalinate is found on List B. Case No: 2295; Pesticide type: insecticide; 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): N-(2-Fluvalinate; Data Call-in (DCI) Date(s): 04/12/91, 03/03/95, 10/13/95, 12/17/96; 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.

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.

An incident occurred in 1992 when the product was used to fog a greenhouse. Vents that were opened inadvertently allowed the product to drift to residential neighborhood. Complaints of symptoms led to 150 people being evacuated and 10 people were seen in a hospital. 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. No further information on the disposition of the case was reported. ...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.

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/

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/

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

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/

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

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/

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (L363)

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (T36)

At high doses, signs of poisoning attributable to fluvalinate include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema. (L863)

At high doses, signs of poisoning attributable to tau-fluvalinate include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema. (L863)

LD50; Species: /Colinus virginianus/ (Bobwhite quail) oral >2510 mg/kg

LC50; Species: /Colinus virginianus/ (Bobwhite quail) dietary >5620 mg/kg diet/8 day

LC50; Species: /Anas platyrhynchos/ (Mallard duck) dietary >5620 mg/kg diet/8 day

LC50; Species: Americamysis bahia (Opossum Shrimp) juvenile; Conditions: saltwater; flow-through; Concentration: 0.11 ug/L for 96 hr (95% confidence interval: 0.09-0.14 ug/L) /22% purity/

For more Ecotoxicity Values (Complete) data for FLUVALINATE (22 total), please visit the HSDB record page.

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).

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).

Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).

Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).

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.

Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)

Pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. (T18, L857)

/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/

Following dermal exposure to fluvalinate, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of fluvalinate. Paralysis can occur after exposure. (L857)

Following dermal exposure to tau-flavulinate, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of tau-fluvalinate. Paralysis can occur after exposure. (L857)

Tolerances are established for residues of the insecticide tau-fluvalinate, cyano-(3-phenoxyphenyl)methyl N-[2-chloro-4-(trifluoromethyl)phenyl]-D-valinate, in or on the following food commodity: honey. /Tau-fluvalinate/

The Agency has completed its assessment of the dietary, residential, occupational, and ecological risk associated with the use of pesticide products containing the active ingredient tau-fluvalinate. Based on a review of these data, the Agency has sufficient information on the human health and ecological effects of tau-fluvalinate to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA.The Agency has determined that tau-fluvalinate-containing products are eligible for reregistration provided that label amendments are made as outlined in Section V. In addition, the Agency intends to require data to confirm some risk conclusions discussed in Section III. ... Based on its evaluation of tau-fluvalinate, the Agency has determined that tau-fluvalinate products, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA and FQPA. Accordingly, should a registrant fail to implement any of the reregistration requirements identified in this document, the Agency may take regulatory action to address the risk concerns from the use of tau-fluvalinate. If all changes outlined in this document are incorporated into the product labels, then all current risks for tau-fluvalinate will be adequately mitigated for the purposes of this determination. /Tau-fluvalinate/

"Fluvalinate" is the common name for the racemic mixture of the 4 isomers of cyano-(3-phenoxyphenyl)methyl N-[2-chloro-4-(trifluoromethyl)phenyl]-valinate (CAS name). "Tau-fluvalinate" is the term for the half resolved mixture (2 of the 4 isomers).

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Fluvalinate is found on List B. Case No: 2295; Pesticide type: insecticide; 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): N-(2-Fluvalinate; Data Call-in (DCI) Date(s): 04/12/91, 03/03/95, 10/13/95, 12/17/96; 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.

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.

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 major metabolic pathways are cleavage of ester linkage and oxidation at the acid and alcohol moieties. Ester hydrolysis leads to formation of anilino acid. The anilino acid is further conjugated with amino acids (glycine, serine, threonine, and valine), bile acids (cholic, taurochoric, and taurochenodeoxycholic), and glycerols (oleoyl- and linoleoylglycerol). In addition, an amide derivative of anilino acid was found. These conjugation reactions of anilino acid with bile acid (cholic acid, taurocholic acid, and taurochenodeoxycholic acid) and with glycerol and monoglycerides have rarely been reported as conjugates with xenobiotics. 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. An unexpected difference between fluvalinate and other pyrethroids is the minimal amt of hydroxylation at the 4'-position of the alcohol moiety. (T80)

/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.

Used as insecticide for control of a wide range of insects and spider mites on indoor and outdoor ornamentals, apples, pears, peaches, vines, cereals, vegetables, cotton, tobacco, and turf; [HSDB]

Farming (Pesticides) [Category: Industry]

For fluvalinate (USEPA/OPP Pesticide Code: 109302) 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./

A broad-range, foliar-applied insecticide and acaricide effective ... against Aphididae, Cicadellidae, Lepidoptera, Thysanoptera, Tetranychidae and Trialeurodes vaporariorum on ornamentals, vegetables, trees and vines.

Control of a wide range of insects (including Lepidoptera, aphids, thrips, leafhoppers, whiteflies, etc) and spider mites on cereals, oilseed rape and potatoes on vines, vegetables and sunflowers and in orchards; also on indoor and outdoor ornamentals, cotton, tea, tobacco and turf; also used for control of Varroa jacobsoni in beehives. /tau-Fluvalinate/

Insecticide ... for use on cotton, field crops, fruits, vegetables and vines.

Fluvalinate can be synthesized by reaction of 2-bromo-3-methylbutyric acid with 2- chloro-3-trifluoromethylaniline, followed by esterification with a-cyano-3-phenoxybenzyl alcohol.

Preparation: C. A. Henrick, B. A. Garcia, Germany 2812169 (1978 to Zoecon).

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.