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Tau-Fluvalinate

HCID 91768
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
102851-06-9
Standard-SMILES
CC(C)[C@@H](Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1
InChIKey
INISTDXBRIBGOC-XMMISQBUSA-N
Summenformel
C26H22ClF3N2O3
Durchschnittliche Molmasse
502,9 g/mol
Monoisotopische Masse
502,1271049

Überblick

Tau-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.

Namen und Bezeichner

Bevorzugter Name
Tau-Fluvalinate
IUPAC
[cyano-(3-phenoxyphenyl)methyl] (2R)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate
Englischer Name
Tau-fluvalinate
Summenformel
C26H22ClF3N2O3
Molmasse
502.91

Namen und Synonyme

Tau-fluvalinate102851-06-9KlartanFluvarolFluwarolDTXSID7037555R533F643E8cyano(3-phenoxyphenyl)methyl N-[2-chloro-4-(trifluoromethyl)phenyl]-D-valinateDTXCID5017555CHEBI:39367D-Valine, N-(2-chloro-4-(trifluoromethyl)phenyl)-, cyano(3-phenoxyphenyl)methyl ester(RS)-alpha-Cyano-3-phenoxybenzyl N-(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyl)-D-valinate
Weitere Namen anzeigen
t-FluvalinateMK 128MavricApistanTau-fluvaliteτ-Fluvalinateau-fluvalinatetau-fluvaliateTAO-FLUVALINATE
N-[2-chloro-4-(trifluoromethyl)phenyl]-D-valine cyano(3-phenoxyphenyl)methyl estercyano(3-phenoxyphenyl)methyl N-(2-chloro-4-(trifluoromethyl)phenyl)-D-valinateN-(2-chloro-4-(Trifluoromethyl)phenyl)-D-valine cyano(3-phenoxyphenyl)methyl esterRefChem:1099400600-363-0cyano(3-phenoxyphenyl)methyl (2R)-2-((2-chloro-4-(trifluoromethyl)phenyl)amino)-3-methylbutanoateMavrik EWSPUR

Eigenschaften

Berechnete Struktureigenschaften

XLogP
7,7
Polarare Oberfläche (TPSA)
71,4 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
9
Schwere Atome
35
Formalladung
0
Komplexität
735

Experimentelle und physikochemische Eigenschaften

Pesticides · 4 Einträge

Pesticides

Insecticides

Active substance -> EU Pesticides database: Approved

Pesticides -> Pyrethrins/Pyrethroids

Endocrine DisruptorsPotential endocrine disrupting compound
Vapor Pressure0.0000001 [mmHg]
Physical DescriptionYellow viscous liquid; Formulated as flowable concentrate and impregnated strips (bee hives); [Reference #1] Colorless viscous liquid; Formulated as an oil in water emulsion; [EFSA]
Collision Cross Section · 3 Einträge

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)]

Physikochemische Eigenschaften

Siedepunkt
450 °C · 450°C
Dichte
1.29 · 1.2900

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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)

Gefahrenhinweise

Regulatory Information · 5 Einträge

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.

Hazards Summary · 1 Eintrag

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]

Hazard Classes and Categories · 5 Einträge

Acute Tox. 4 (98.4%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 3

Flammable liquids - Category 4

Acute Tox. 4 *

Toxikologische Informationen

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

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)

Verwendung und Herstellung

Uses · 4 Einträge

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Datenbank-Bezeichner

CAS
102851-06-9
PubChem CID
91768
DTXSID
DTXSID7037555
ChEMBL
CHEMBL1895592
ChEBI
CHEBI:39367
UNII
R533F643E8
EC Number
600-363-0
Nikkaji
J59.569A
Dampfdruck
9 · 9×10-11 Pa (25 °C)
Flammpunkt
90 °C · 90 °C
storage temp.
Sealed in dry,Room Temperature
Löslichkeit
10 mg/ml,DMSO: · DMF: 10 mg/ml,DMSO: 10 mg/ml,Ethanol: 10 mg/ml
Wasserlöslichkeit
0.001 mg · 0.001 mg l-1 (20 °C)
pka
-1.16 · -1.16±0.50(Predicted)
BRN
8092907 · 8092907
Henry's Law Constant
8.3 · 8.3×103 mol/(m3Pa) at 25℃, Maniere et al. (2011)
Major Application
agricultureenvironmental
InChIKey
INISTDXBRIBGOC-XMMISQBUSA-N
SMILES
C(OC(C#N)C1=CC=CC(OC2=CC=CC=C2)=C1)(=O)[C@@H](C(C)C)NC1=CC=C(C(F)(F)F)C=C1Cl
LogP
7.31 · 7.310 (est)
CAS Datenbank
102851 · 102851-06-9(CAS DataBase Reference)
EPA chemische Informationen
Tau-fluvalinate (102851-06-9)
Treatment · 2 Einträge

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)

Health Effects · 2 Einträge

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)

Exposure Routes · 2 Einträge

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

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

Toxicity Summary · 2 Einträge

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)

Signs and Symptoms · 2 Einträge

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)

Carcinogen Classification · 2 Einträge

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).

Toxicity Data · 2 Einträge

LD50: 261-282 mg/kg (Oral, Rat) (L887)

LD50: 282 mg/kg (Oral, Rat) (L886) LD50: >2000 mg/kg (Dermal, Rat) (L886)

RAIS Toxicity Values · 2 Einträge

0.01

OPP

EPA Human Health Benchmarks for Pesticides · 5 Einträge

Tau-fluvalinate

0.01

70

Children

Human Health Benchmarks for Pesticides - 2021 Update

Sicherheitsdaten

wgk
3
ridadr
UN2810 6.1/PG 3
hs_code
29269090
risk_code
22-38-50/53
hazard_code
Xn,N
safety_code
24-59-61
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Skin Irrit. 2

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)

Household ProductsInformation on 2 consumer products that contain Tau-fluvalinate in the following categories is provided:
Anwendungen · 2 Einträge

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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-Brom-3-methylbuttersure2-Chlor-4-trifluormethylanilinN-ChlorsuccinimidAlkohol 3-phenoxybenzylCyhalothrinIsovalerylchloridMethansulfonylchloridm-Phenoxybenzaldehyd

Nachgelagerte Produkte

4-Methylpyridin

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Ergänzende Hinweise

DefinitionChEBI: The (2R) diastereomers of fluvalinate. A synthetic pyrethroid insecticide, it is used to control varroa mites in honey bee colonies.