70124-77-5

Usage

Uses

Used in Agriculture:
Flucythrinate is used as an insecticide for controlling a wide range of insects on various crops. It is applied to protect plants such as cotton, fruit trees, vines, citrus, bananas, pineapples, olives, coffee, cocoa, hops, vegetables, soyabeans, cereals, alfalfa, sugar beet, sunflowers, and tobacco from insect damage.
As a nonsystemic insecticide, Flucythrinate is used for its ability to control pests on the surface of plants without being absorbed into the plant's system. This makes it an effective tool in integrated pest management strategies, helping to reduce the impact of insects on crop yields and quality while minimizing the environmental impact of pesticide use.

Trade name

AASTAR?[C]; CYBOLT?; CYTHRIN?; FUCHING JUJR?; GUARDIAN?[C]; PAYOFF?[C]; STOCK GUARD?; TOMAHAWK?

Pharmacology

Flucythrinate is the (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyrate analog of fenvalerate, partially resolved. Its insecticide action is approximately two times higher compared with fenvalerate (138,142).

Environmental Fate

Surface Water. The half-life of ?ucythrinate in an estuarine environment is 34 days (Schimmel et al., 1983).Chemical/Physical. Hydrolyzes in aqueous solutions forming acetic acid and other compounds.

Metabolic pathway

Flucythrinate is an analogue of fenvalerate and would be expected to have a similar fate.

Degradation

Flucythrinate is a stable compound but it is readily hydrolysed at alkaline pH to afford 2-(4-difluoromethoxyphenyl)-3-methylbutyric acid (2), 3PBAl(3) and cyanide ion. Its DT50 values at 27 °C are 52 days (pH 5) and 6.3 days (pH 9). It undergoes aqueous and soil surface photolysis with DT50 values of 1-4 days and <2 days, respectively. The products formed under aqueous conditions were 2 and 3. Compound 3 was oxidised to 3PBA (4) and reduced to 3PBAlc (5). The α-carbamoyl (amide) derivative (6) of 3PBAlc was also detected. On soil surfaces, products were similar with the exceptions that 3PBA was not formed and the α-amide (7) and a-carboxy derivative (8) were formed. These are usually considered to be products of thermal degradation (Dureja and Chattopadhyay, 1995).

InChI:InChI=1/C26H23F2NO4/c1-17(2)24(18-11-13-21(14-12-18)32-26(27)28)25(30)33-23(16-29)19-7-6-10-22(15-19)31-20-8-4-3-5-9-20/h3-15,17,23-24,26H,1-2H3/t23?,24-/m0/s1

Upstream product

• 39515-47-4 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile 
• 70125-00-7 2-(4-difluoromethoxyphenyl)-3-methylbutyryl chloride 
• 74-87-3 methylene chloride 

Relevant academic research and scientific papers

Insecticidal resin coating film

An insecticidal resin coating film comprising a combination of an acrylonitrile and/or methacrylonitrile copolymer resin and an insecticidal component selected from the group consisting of specified compounds exhibits an insecticidal effect, since the compound is kept on the surface of the coating film in a state capable of exhibiting its insecticidal effect for a long period of time.

Method for the racemization of (2)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid

A method for the racemization and hydrolysis of alkyl esters of (-)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid, followed by the resolution of said resulting racemic acid into its optically active components via salts prepared from the same with optically active amines and recovery of the dextrorotatory (+) isomer therefrom. The present invention also relates to insecticidal pyrethroids prepared from (+)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid.

Method for the alkylation of phenylacetonitriles

A method for the alkylation of certain substituted phenylacetonitriles with alkylhalides in the presence of solid particulated alkali metal hydroxides under essentially anhydrous conditions. Trialkylamine catalysts may optionally be utilized. Compounds obtained by this method, some of which are valuable intermediates in the preparation of pyrethroid pesticides, are described.

Method for the control of cattle grubs employing m-phenoxybenzyl and α

A method for the control of larvae of heel flies which parasitize ruminants and other domestic and farm animals involving topical application of a larvicidally effective amount of a m-phenoxybenzyl or α-cyano-m-phenoxybenzyl ester of a 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenyl alkanoic acid.

Method for preparing a mixture of stereoisomers of α-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates

A method for preparing α-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates which consist substantially of or are rich in the enantiomer pair (S)-α-cyano-3-phenoxybenzyl (S)-2-(4-substituted-phenyl)isovalerate and (R)-α-cyano-3-phenoxybenzyl (R)-2-(4-substituted-phenyl)isovalerate.

(-)-α-Cyano-m-phenoxybenzyl(+)-α-isopropyl-4-difluoromethoxyphenylacetate

The invention is the compound (-)-α-cyano-m-phenoxybenzyl(+)-α-isopropyl-4-difluoromethoxyphenylacetate.

M-phenoxybenzyl and α-cyano-M-phenoxybenzyl esters of 2-haloalkyl (oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids

The invention is m-phenoxybenzyl esters of 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful insecticidal and acaricidal agents.

2-Haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)-phenylalkanoic acids

The invention is 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful intermediates in the preparation of insecticides of m-phenoxybenzyl and α-cyano-m-phenoxybenzyl esters.