102851-06-9CC(C)[C@@H](Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1INISTDXBRIBGOC-XMMISQBUSA-NTau-fluvalinate is the (2R) diastereomers of fluvalinate. A synthetic pyrethroid insecticide, it is used to control varroa mites in honey bee colonies. It has a role as a pyrethroid ester insecticide and a pyrethroid ester acaricide.
Pesticides
Insecticides
Active substance -> EU Pesticides database: Approved
Pesticides -> Pyrethrins/Pyrethroids
218.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Pesticides; Note: Two peaks in drift spectrum]
220.53 Ų [M+Cl]-
215.83 Ų [M]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+; Note: drift peak 1 (of 2)]
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Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Warning
H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Hazard Traits - Developmental Toxicity; Environmental tox
Regulation (EC) No 396/2005 (amended)
Tau-fluvalinate is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2011/19/EU, Reg. (EU) 2020/2007, Reg. (EU) 2024/1206, Reg.(EU) No 2018/1266, Reg.(EU) No 540/2011
Tau-Fluvalinate: 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.
A mild skin and eye irritant in rabbits; Not sensitizing to guinea pig skin; [EFSA] Can cause pyrethroid reaction on skin contact manifested by tingling sensations and/or itching (often severe); Not likely to be a human carcinogen. [Reference #1]
Acute Tox. 4 (98.4%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 3
Flammable liquids - Category 4
Acute Tox. 4 *
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)
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 amount of hydroxylation at the 4'-position of the alcohol moiety. (T80)
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102851-06-9DTXSID7037555CHEMBL1895592CHEBI:39367Following 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)
Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).
Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).
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)
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)
Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (L135)
No indication of carcinogenicity to humans (not listed by IARC).
LD50: 261-282 mg/kg (Oral, Rat) (L887)
LD50: 282 mg/kg (Oral, Rat) (L886) LD50: >2000 mg/kg (Dermal, Rat) (L886)
0.01
OPP
Tau-fluvalinate
0.01
70
Children
Human Health Benchmarks for Pesticides - 2021 Update
Used as broad spectrum pyrethroid insecticide/miticide for beehives, ornamentals, greenhouses, buildings and perimeters, ant mounds, and carrot and other crops grown for seed; [Reference #1] Used in the EU as an insecticide/acaricide for peaches, potatoes, and wheat; [EFSA]
Farming (Pesticides) [Category: Industry]
Pyrethroids are used as insecticides. (L857)
Pyrethroids are used as insecticides. (L857)
BeschreibungFluvalinate is a viscous, yellow oil in appearance. It is very soluble in organic solvents and aromatic hydrocarbons and insoluble in water. It is a synthetic pyrethroid. It is used as a broad-spectrum insecticide against moths, beetles, fleas, turf and ornamental insects, and other insect pests on cotton, cereal, grape, potato, fruit tree, vegetable, and plantation crops. It is available in emulsifiable concentrates, suspensions, and flowable formulations. Fluvalinate is a moderately toxic compound in the U.S. EPA toxicity class II. Some formulations may have the capacity to cause corrosion of the eyes. Pesticides containing fluvalinate must bear the signal word DANGER on the product label. Fluvalinate is classified as an RUP because of its high toxicity to fish and aquatic invertebrates.
VerwendenFluvalinate is used to control a wide range of insects and spider mites on fruit trees, vines, vegetables, cereals, cotton, tea, tobacco, ornamentals and other crops. It is also used for parasite control in bee hives.
DefinitionChEBI: The (2R) diastereomers of fluvalinate. A synthetic pyrethroid insecticide, it is used to control varroa mites in honey bee colonies.