102851-06-9

Basic information

• Product Name: Tau-fluvalinate
• Synonyms: t-Fluvalinate;TAU-FLUVALINATE 250MG;TAU-FLUVALINATE PESTANAL, 250 MG;MAVRIK, 100MG, NEAT;(alpha-RS,2R)-Fluvalinate;D-Valine, N-2-chloro-4-(trifluoromethyl)phenyl-, cyano(3-phenoxyphenyl)methyl ester;n-[2-chloro-4-(trifluoromethyl)phenyl]-d-valine (rs)-cyano(3-phenoxyphenyl)methyl ester;tau-fluvalinate (bsi,e-iso)
• CAS NO: 102851-06-9
• Molecular Formula: C₂₆H₂₂ClF₃N₂O₃
• Molecular Weight: 502.93
• Product Categories: INSECTICIDE
• Mol File: 102851-06-9.mol

Chemical Properties

• Boiling Point: 450°C
• Flash Point: 90 °C
• Appearance: /
• Density: 1.2900
• Vapor Pressure: 7.71E-13mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• PKA: -1.16±0.50(Predicted)
• Water Solubility: 0.001 mg l-1 (20 °C)
• BRN: 8092907
• CAS DataBase Reference: Tau-fluvalinate(CAS DataBase Reference)
• NIST Chemistry Reference: Tau-fluvalinate(102851-06-9)
• EPA Substance Registry System: Tau-fluvalinate(102851-06-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-38-50/53
• Safety Statements: 24-59-61
• RIDADR: UN2810 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 102851-06-9(Hazardous Substances Data)

Usage

Health Hazard

Exposures to fl uvalinate cause coughing, sneezing, throat irritation, itching, or burning sensations on the arms or face with or without a rash, headache, and nausea. Prolonged period of exposures to pyrethroids cause adverse effects on the CNS, liver, and kidneys. Fluvalinate is slightly toxic to birds.

Potential Exposure

Pyrethroid insecticide used as a broad spectrum insecticide to control moths, beetles and other pests on cereals, potatoes, fruit trees, vegetables, fleas, cot ton, turf and ornamentals. It is also used to control varroa mites in honey bees. Some applications may be classified as a United States Environmental Protection Agency Restricted Use Pesticide (RUP). Formerly used as an insec ticide. Production discontinued by Sandoz Agro, Inc. Incompatibilities: Corrosive to some metals. Keep away from strong oxidizers and alkaline materials. Decomposes in temperatures above 350℃ releasing toxic vapors of hydrogen chloride, nitrogen oxides, and hydrogen fluoride.

Metabolic pathway

The information reported below is derived from studies on fluvalinate, the racemic m-valinate (CASRN 69409-94-5). This has been superseded by the D-isomer. Evidence is given below to show that the results derived from fluvalinate are relevant to tau-fluvalinate. The chemical and photochemical degradation of fluvalinate and its degradation in soils have been reported. Information on metabolism in plants, rats, monkeys, cows and chickens is also published. The metabolism of fluvalinate is dominated by hydrolysis followed by oxidation and conjugation of the metabolites. Novel bile acid conjugates are highlighted. All quantitative data reported below are for the lower of usually two doses.

storage

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.

Shipping

UN2902 Pesticides, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Degradation

Fluvalinate is readily hydrolysed under basic conditions. Half-lives at pH 5, 7 and 9 were 48,38.5 and 1.1 days, respectively (PM). A value of a few minutes would be expected at pH 12. The compound is very sensitive to photodegradation. [14C-trifluoro- methyl]Fluvalinate and [14C-benzyl]fluvalinateh ave been studied in solution (water and methanol) and as thin films on soils and glass (Quistad and Staiger, 1984). Its half-life in sunlight under these conditions is about 1 day, but in dilute aqueous solution it can be as short as 10 minutes (PM). The only sigruficant product retaining the ester structure (up to 18% yield) was the amide (7). Its formation was non-photochemical and was directly related to the temperature of the system. A minor product which retained both portions of the molecule was the COTelimination product (12). Under aqueous conditions 7 was a minor product and 12 was not detected. 2-Chloro-4-(trifluoromethyl)aniline( 3) was the major product derived from the acid moiety on a thin film on glass and under aqueous conditions (up to 40% and l8%, respectively). On soil surfaces the major products were the amide (7) and the anilino acid, N-(2-chloro-α,α,α-trifluoro-ptolyl)- D-valinate (2), and 35% remained bound. This residue may have arisen via the formation of aniline (3) (which was trapped as a volatile product from the glass surface). The formation of 2 and 7 were considered to be largely non-photochemical because they were also found under dark conditions. The dicarboxylic acid (11) was found as a 1% metabolite on soil surface photolysis. The 3-phenoxybenzyl (3PB) portion (the alcohol moiety) was seen under all conditions as 3PBA aldehyde (5) and its oxidation product 3PBA (6) (together 40-50% of the applied radioactivity). The cyanohydrin (4) was also detected and this was probably a primary product. Also detected in 341% yields were the formanilide (8), (3-phenoxyphenyl)acetonitrile (9) and the oxamic acid (10). These products are illustrated in Scheme 1.

Waste Disposal

Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.

Precautions

Occupational workers should avoid contact of fl uvalinate with the skin and eyes and avoid breathing contaminated fumes. Wear suitable protective clothing, nitrile rubber gloves, and safety glasses or a face shield. Fluvalinate is an RUP and should be used, handled, and/or purchased only by certifi ed applicators.

InChI:InChI=1/C26H22ClF3N2O3/c1-16(2)24(32-22-12-11-18(14-21(22)27)26(28,29)30)25(33)35-23(15-31)17-7-6-10-20(13-17)34-19-8-4-3-5-9-19/h3-14,16,23-24,32H,1-2H3/t23?,24-/m1/s1

Synthetic route

(R)-2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoic acid + methanesulfonyl chloride (124-63-0) + 3-Phenoxybenzaldehyde (39515-51-0) → (RS)-α-cyano-3-phenoxybenzyl (R)-2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoate (102851-06-9)

Conditions	Yield
With dmap; aqueous KOH In 1-methyl-pyrrolidin-2-one; hexane; water; toluene	92.1%

Upstream product

• 114298-69-0 (R)-2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoic acid 
• 124-63-0 methanesulfonyl chloride 
• 39515-51-0 3-Phenoxybenzaldehyde 

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