68359-37-5

Usage

References

https://www.beyondpesticides.org http://onlinelibrary.wiley.com http://pmep.cce.cornell.edu https://en.wikipedia.org/wiki/Cyfluthrin http://dissemination.echa.europa.eu

Reactivity Profile

Cyfluthrin is a pyrethrine derivative. Incompatible with azocyclotin, and perhaps other azo compounds and organometallics.

Trade name

AZTEC?; ATTATOX?; BAY FCR 1272?; BAYTHROID?; BAYTHROID? H; BAYTHROID? TECHNICAL; BUG-B-GON?; CONTUR?; CYLATHRIN?; EULAN SP?; FCR 1272?; INTUDER?; INTUDER HPX?; LASER?; RENOUNCE?; RESPONSAR?; SOLFAC?; TEMPO?; TEMPO? H; TEMPO? 20WP

Potential Exposure

Cyfluthrin is a synthetic pyrethroid, nonsystemic insecticide used to control a variety of chew- ing and sucking insects on cotton, hops, cereals, corn, pea- nuts, fruit, potatoes, and other crops and vegetables. It is also used to control structural pests such as termites. Cyfluthrin can be found in both Restricted Use Pesticides (RUP) and General Use Pesticides (GUP) category. It is also a nitrile.

Metabolic pathway

The non-enzymatic hydrolyzed products of 14C- cyfluthrin are isolated and identified by the incubation reaction mixture of a buffer solution. The products are derived from the hydrolysis of the ester linkage of cyfluthrin via cyanhydrin. This results in the corresponding aldehyde which undergoes both oxidation and reduction to give rise to carboxylic acid and benzyl alcohol, respectively.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3349 (pyrethroid pesticide, solid, toxic)/151 Pyrethroid pesticide, solid toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material UN3439 Nitriles, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Degradation

Cyfluthrin is a stable compound but it is hydrolysed at high pH. DT50 values in water at 22 °C at pH 4, 7 and 9 were 25-117, 11-20, and 3-7 days, respectively (PM). Under aqueous photolysis conditions (but using UV light and acetonitrile in the solution), its half-life was 12 days. The benzldehyde (3, 3%) (Scheme 1) and the benzoic acid (5, 9%) were detected at 144 hours (PSD). On a soil surface in light, the initial half-life was 2 days. At day 9, 62% of the radioactivity was recovered as: cyfluthrin (36%)) 3 (2%), 5 (4%) and unidentified components (PSD). The compound was stable on a soil surface in the dark.

Incompatibilities

May react violently with strong oxidi- zers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders, or dust. Incompatible with silver compounds. Mixture with some silver compounds forms explosive salts of silver oxalate. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give car- boxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids .

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.

Synthetic route

cyfluthrin (68359-37-5) → 2-(4-fluoro-3-phenoxyphenyl)-2-hydroxyethanenitrile (76783-44-3) + 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (55701-05-8) + α-cyano-4-fluorobenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

Conditions	Yield
With Trichoderma viride 5-2 In phosphate buffer at 28℃; pH=6.5;

cyfluthrin (68359-37-5) → 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (55701-05-8)

Conditions	Yield
With sodium hydroxide In methanol for 2h; Heating;

Upstream product

• 1820573-27-0 (S)-α-cyano-4-fluoro-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 

Downstream Products

• 68359-57-9 4-fluoro-3-phenoxybenzaldehyde 
• 55701-05-8 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 76783-44-3 2-(4-fluoro-3-phenoxyphenyl)-2-hydroxyethanenitrile 

Relevant academic research and scientific papers

Chiral stability of synthetic pyrethroid insecticides

Synthetic pyrethroids are chiral compounds consisting of multiple stereoisomers. Evaluation of enantioselectivity in environmental fate and ecotoxicity requires analytical methods that preserve stereoisomer integrity during analysis. In this study, we characterized the stability of stereoisomers from four commonly used pyrethroids, cis-bifenthrin (cis-BF), permethrin (PM), cypermethrin (CP), and cyfluthrin (CF), during gas chromatography (GC) analysis and sample preparation. Stereoisomers of cis-BF and PM were found to be stable, but those of CP and CF were unstable, under heat or in water. Isomer conversion occurred only at the aC in CP or CF, causing the analyte stereoisomer to convert to an epimer. At a GC inlet temperature of 260°C, about 9% conversion occurred for CP and CF. In organic solvents and sterile water, stereoisomers of cis-BF and PM were stable, but slow isomer conversion was observed for CP and CF in water at ambient temperature. However, isomer conversion for CP and CF was relatively insignificant (2-3%) when the GC inlet temperature was kept at ≤ 180°C or when on-column injection was used. Isomer conversion at the αC in water suggests that abiotic processes may also contribute to enantioselectivity observed in the environment for pyrethroids with the asymmetric αC.

Secondary battery with a radical compound active material

A radical compound may be used as an active material for an anode layer 2 to provide a novel stable secondary battery with a higher energy density and a larger capacity. The radical compound used has, for example, a spin concentration of 1021 spins/g or more.

Wood preservatives

Wood preservatives having biocidal properties which include quaternary ammonium compounds of general formula (I): wherein R1 is a C8-18-alkyl group or an optionally substituted benzyl group, R2 is a C8-18-alkyl group, R3 is a C1-4-alkyl group or a group of the formula —[CH2—CH2—O]n—H, R4 is a C1-4-alkyl group, n is a number from 0.5 to 8, preferably from 1 to 5, and A?is the anion of an organic carboxylic acid which contains 2 to 12 C atoms and carries at least one hydroxyl, amino or sulfonic acid group. The wood preservatives also penetrate deeply into the wood without the use of pressure, and have only a mild corrosive action on metals. Furthermore, a process for treating timbers with these compositions, concentrates for the preparation thereof, the use of new and known quaternary ammonium compounds in wood preservatives and new quaternary ammonium compounds and their use as biocides.

Fungicidal active compound combinations

The present application relates to new active compound combinations composed, on the one hand, of prior art compounds metaconazole, 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl-methyl)cyclopentanol and imidacloprid, 1-[(6-chloro-3-pyridinyl)-methyl]-4,5-dihydro-N-nitro-1H-imidazole-2-amine, and, on the other hand, of other prior-art active compounds, the combinations being extremely suitable for the protection of wood products.

Anti-fouling compositions

An anti-fouling composition comprising a carrier, and a binder, the improvement which comprises an effective amount of at least one insecticide. The composition is applied to the surfaces of articles which come into contact with seawater or brackish water, especially wood. Other conventional anti-fouling agents may also be present.

Para-hydroxyphenylacetic acid for reducing the repellency of insecticides

The present invention relates to the new use of p-hydroxyphenylacetic acid, by itself or in a mixture with other chemical compounds, for reducing the repellency of insecticides in the control of cockroaches, and to cockroach control compositions which comprise these mixtures, details being found in the description.

Methods and agents for combating cockroaches

The present invention relates to the use of compounds of the general formula I STR1 in which R1 represents C1 -C5 -alkyl or hydroxy-C1 -C5 -alkyl; R2 represents C1 -C5 -alkyl; and m represents an integer from 10 to 20, for combating cockroaches.

Conversion of pyrethroid isomers to move active species

Crystallizable pyrethroid isomers or enantiomer pairs are converted to more pesticidally active isomers by contacting a hydrocarbon slurry of the starting isomers with a base and a catalyst, the catalyst being substantially soluble in the slurry and selected from a quaternary ammonium compound, a quaternary phosphonium compound and a crown ether, agitating the slurry while maintaining a temperature effective for conversion, and recovering the resulting isomers. The tendency to form benzoin ester by-product is reduced by including in the slurry a weak base, an aldehyde scavenger such as a metabisulfite, and/or a tetraalkyl (C1 -C5) ammonium halide catalyst dissolved in an aprotic solvent such as an organic nitrile. The process typically is effective for enriching cypermethrin, cyfluthrin and (cyano (3-phenoxyphenyl)methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate in the more active species.

Long-acting pyrethrum/pyrethroid based pesticides with silicone stabilizers

Pesticidal compositions based on nontoxic, naturally unstable insecticides (pyrethrum, synthetic pyrethroids and mixtures thereof) include a liquid alkyl aryl silicone polymer which stabilizes the insecticide to provide an extended effective killing life. The compositions additionally include a synergist to provide an immediate killing action and an antioxidant to protect the insecticide against destruction by oxygen. Ultraviolet protectants and insect repellents may also be included. Applications include control of insect pests to animals and plants and general purpose insect control. Exemplary formulations are given for compositions to be applied as sprays, dips, powdered or dusts, foggers and shampoos.

Baits for combating vermin

An insecticidal bait comprising an insecticidally effective amount of (a) α-cyano-3-phenoxy-4-fluorobenzyl 2,2-dimethyl-3-(β,β-dichlorovinyl)-cyclopropanecarboxylate of the formula STR1 and (b) an insect attracting amount of at least one ingestion attractant. It may also contain additional insecticides, a grinding auxiliary, carrier, adhesive or swelling agent. Surprisingly the principal active ingredient does not repel insects, as do other pyrethroid-like insecticides in baits.