Fluvalinate 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.
Yellow to yellow-amber, viscous oil. Sweet,
weak odor.
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 moderately toxic compound in the US EPA toxicity class II. Some formulations may have the capacity to cause corrosion of the eyes. Pesticides containing fl uvalinate must bear the signal word DANGER on the product label. Fluvalinate is classifi ed as an RUP because of its high toxicity to fi sh and aquatic invertebrates.
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.
ChEBI: The (2R) diastereomers of fluvalinate. A synthetic pyrethroid insecticide, it is used to control varroa mites in honey bee colonies.
The commercial production of tau-fluvalinate involves a multi-step chemical synthesis and purification process. Initially, fluvalinate is synthesised through esterification and coupling reactions involving cyano-(3-phenoxyphenyl)methanol and a substituted aniline derivative. Tau-fluvalinate is then isolated as a specific diastereomeric mixture, primarily the (2R)-isomer, through stereoselective synthesis or resolution techniques. Industrial-scale production focuses on optimising reaction conditions, including timely acid neutralisation, to prevent equipment corrosion and ensure high purity.
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.
Contact and stomach action. Sodium channel modulator.
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.
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.
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.
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.
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.
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.
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.
Insecticide; Acaricide; Veterinary substance
