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τ-플루바리네이트

Tau-Fluvalinate

HCID 91768
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
102851-06-9
표준 SMILES
CC(C)[C@@H](Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1
InChIKey
INISTDXBRIBGOC-XMMISQBUSA-N
분자식
C26H22ClF3N2O3
평균 분자량
502.9 g/mol
단동위원소 질량
502.1271049

개요

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.

이름 및 식별자

우선 이름
Tau-Fluvalinate
IUPAC
[cyano-(3-phenoxyphenyl)methyl] (2R)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate
현지명
τ-플루바리네이트
영어명
Tau-fluvalinate
분자식
C26H22ClF3N2O3
분자량
502.91

이름 및 동의어

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
이름 더 보기
τ-플루바리네이트플루버린산염t-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

물성

구조 계산 물성

XLogP
7.7
극성 표면적
71.4 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
8
회전 가능 결합 수
9
무거운 원자 수
35
형식 전하
0
복잡도
735

실험 및 물리화학적 성질

Pesticides · 4건

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 · 3건

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)]

물리화학적 성질

끓는 점
450 °C · 450°C
밀도
1.29 · 1.2900
증기압
9 · 9×10-11 Pa (25 °C)
인화점
90 °C · 90 °C
저장 조건
Sealed in dry,Room Temperature

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Regulatory Information · 5건

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 · 1건

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 · 5건

Acute Tox. 4 (98.4%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 3

Flammable liquids - Category 4

Acute Tox. 4 *

독성 정보

Treatment · 2건

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)

화학 및 산업

약리 정보

Metabolism/Metabolites · 2건

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)

용도 및 제조

Uses · 4건

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]

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

데이터베이스 식별자

CAS
102851-06-9
PubChem CID
91768
DTXSID
DTXSID7037555
ChEMBL
CHEMBL1895592
ChEBI
CHEBI:39367
UNII
R533F643E8
EC Number
600-363-0
Nikkaji
J59.569A
용해도
10 mg/ml,DMSO: · DMF: 10 mg/ml,DMSO: 10 mg/ml,Ethanol: 10 mg/ml
수용성
0.001 mg · 0.001mg l-1(20°C)
산도 계수 (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)
주요 응용
농업환경
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)
EPA
Tau-fluvalinate (102851-06-9)

화학적 성질

Yellow viscous liquid

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 · 2건

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 · 2건

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

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

Toxicity Summary · 2건

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 · 2건

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 · 2건

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 · 2건

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 · 2건

0.01

OPP

EPA Human Health Benchmarks for Pesticides · 5건

Tau-fluvalinate

0.01

70

Children

Human Health Benchmarks for Pesticides - 2021 Update

안전 데이터

wgk
3
ridadr
UN2810 6.1/PG 3
HS 번호
29269090
risk_code
22-38-50/53
hazard_code
Xn,N
safety_code
24-59-61
기존화학 물질
KE-09100
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Skin Irrit. 2
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

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:
응용 분야 · 2건

개요Fluvalinate 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.

용도Fluvalinate 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.

상·하류 제품 정보

상류 원료

2-Bromo-3-methylbutyric acid4-Amino-3-chlorobenzotrifluorideN-클로로숙신이미드페녹시벤질(3-)알코올시할로트린이소발레로일클로라이드메탄설포닐 클로라이드3-페녹시벤즈알데하이드

하류 제품

γ-피콜린

공급사100 곳

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추가 설명

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