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Tau-fluvalinate

Tau-fluvalinate structure

CAS No:
102851-06-9
Formula:
C26H22ClF3N2O3
Chemical Name:
Tau-fluvalinate
Synonyms:
D-Valine,N-[2-chloro-4-(trifluoromethyl)phenyl]-,cyano(3-phenoxyphenyl)methyl ester;Tau-fluvalinate;Klartan;Fluwarol;Fluvarol;τ-Fluvalinate;Spur;Apistan;Mavrik;Mavrik Aquaflow;Mavrik 2E;Mavrik 25EC;Minadox;Spur 22EW;Mavrik EW
Categories:
Agrochemicals > Insecticides

Description

Fluvalinate is a viscous, yellow oil in appearance. It is very soluble in organic solvents and aromatic hydrocarbons and insoluble in water. Fluvalinate is a synthetic pyrethroid. It is used as a broad-spectrum insecticide against moths, beetles, and other insect pests on cotton, cereal, grape, potato, fruit tree, vegetable and plantation crops, fl eas, and turf and ornamental insects. It is available in emulsifi able concentrates, suspensions, and fl owable formulations. Fluvalinate is a moder

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.

Tau-fluvalinate Basic Attributes

Molecular Weight：

502.93

Exact Mass：

502.91

EC Number：

600-363-0

DSSTox ID：

DTXSID7037555

HScode：

29269090

Characteristics

PSA：

71.4

XLogP3：

5.50 (HPLC measurement)

Density：

1.29 g/cu cm at 25 deg C

Melting Point：

-14.1 deg C (99.5% purity, glass transition temperature)

Boiling Point：

450°C

Flash Point：

90 °C

Refractive Index：

1.572

Water Solubility：

At 25 deg C (91.6% purity): >500g/L in acetone, ethyl acetate, methanol, octanol, dichloromethane and toluene

Storage Conditions：

2-8°C

Vapor Pressure：

9×10 -11 Pa (25 °C)

Collision Cross Section：

220.53 Å² [M+Cl]-

Safety Information

Transport codes：

UN28106.1/PG3

wgk germany：

hazard class code：

22-38-50/53

safety instructions：

24-59-61

Marks：

Xn,N

Storage features：

Fluvalinate should be kept stored only in its original container at a temperature not exceeding 40°C. It should be kept away from food, drink, and animal feedstuffs.

Stability/Shelf Life：

On hydrolysis 50% loss occurs: at 25 deg C in 30 days (pH3 and pH6), 1-2 hr (pH9); at 42 deg C in 35 days (pH3), 8 days (pH6), and 1 day (pH9). It is stable in glass > 1.5 years at 42 deg 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.

Precautionary statement(s)：

P273-P501

Hazard Statements：

H302-H315-H410

GHS Classification：

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P321, P330, P332+P313, P362, P391, and P501|H302 (99.45%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 182 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P271, P281, P284, P301+P310, P304+P340, P307+P311, P308+P313, P310, P314, P320, P321, P330, P403+P233, P405, and P501|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P310, P302+P352, P304+P340, P307+P311, P310, P314, P320, P321, P330, P333+P313, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501

Toxicity

Mobility：

5.07e+05 L/kg

Drug Information

MeSH：

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.)

MeSH Entry Terms：

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

Tau-fluvalinate Use and Manufacturing

Methods of Manufacturing

Preparation Method 1: Alpha-bromoisovaleric acid is chlorinated with SOCl2 to prepare alpha-bromoisovaleryl chloride, which is then reacted with alpha-cyano-3-phenoxybenzyl alcohol to produce alpha-cyano-(3- Phenoxybenzyl)-2'-bromoisovalerate, and finally condensed with 2-chloro-4-trifluoromethylaniline to produce fluvalinate. Preparation Method Two α-aminoisovaleric acid is brominated with hydrogen bromide to produce α-bromoisovaleric acid. It is then reacted with difluoromethylaniline and N-chlorosuccinimide, followed by reaction with α-cyano-3-phenoxybenzyl alcohol. Preparation of acid For the preparation of alcohol, see the preparation method of cyhalothrin. Synthesis of flufluthrin

Uses

Fluvalinate 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.

Use Classification：

Agrochemicals -> Insecticides

Agrochemical：

Tau-fluvalinate has known environmental transformation products that include 2-chloro-4-(trifluromethyl) anilino-3 methyl butanoic acid and haloaniline.

Computed Properties

Molecular Weight:502.9
XLogP3:7.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:9
Exact Mass:502.1271047
Monoisotopic Mass:502.1271047
Topological Polar Surface Area:71.4
Heavy Atom Count:35
Complexity:735
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Chlorosuccinimide

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