64257-84-7

Basic information

• Product Name: Fenpropathrin
• Synonyms: Cyano(3-phenoxyphenyl)methyl 2,2,3,3-tetramethylcyclopropanecarboxylate (9ci);Hsdb 6636;(+-)-2,2,3,3-tetramethylcyclopropanecarboxylicacidcyano(3-phenoxyphenyl)met;2,2,3,3-tetramethylcyclopropanecarboxylicacidcyano(3-phenoxyphenyl)methylest;AMITOL;HERALD;FENOTHRIN;DIGITAL
• CAS NO: 64257-84-7
• Molecular Formula: C₂₂H₂₃NO₃
• Molecular Weight: 349.42
• EINECS: 254-485-0
• Product Categories: INSECTICIDE;Agro-Chemicals
• Mol File: 64257-84-7.mol

Chemical Properties

• Melting Point: 45-50°C
• Boiling Point: 483.6°C (rough estimate)
• Flash Point: 195.5 °C
• Appearance: /
• Density: 1.1500
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: 0-6°C
• Water Solubility: 0.014 mg l-1 (25 °C)
• CAS DataBase Reference: Fenpropathrin(CAS DataBase Reference)
• NIST Chemistry Reference: Fenpropathrin(64257-84-7)
• EPA Substance Registry System: Fenpropathrin(64257-84-7)

Safety Data

• Hazard Codes: T+:N
• Statements: 21-25-26-50/53:
• Safety Statements: 28-36/37-38-45-60-61:
• Hazardous Substances Data: 64257-84-7(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Fenpropathrin is used as an insecticide for controlling many species of mites and insects on various crops. It is effective in protecting a wide range of plants, including pome fruit, citrus, vines, hops, vegetables, cotton, ornamentals, and glasshouse crops such as tomatoes. The application of Fenpropathrin helps to prevent damage to crops caused by these pests, ensuring a healthy and productive yield.

Metabolic pathway

Fenpropathrin possesses only one chiral centre (at benzylic carbon) and therefore presents a much simpler stereochemical picture than that seen with most of the other pyrethroids. Most metabolic work has been conducted with the RS racemate. Solution and surface photochemistry, and degradation in water, soils, plants and animals, have been reported. The fate of the 3-phenoxybenzyl portion of the molecule is very similar to that reported for cypermethrin and other analogues. Degradation is mainly by ester cleavage and hydroxylation.

Degradation

A detailed study of the kinetics of the hydrolysis of [14C-cyclopropyl]- fenpropathrin and [14C-benzyl]fenpropathrins howed that ester bond cleavage predominated over cyan0 group hydration (Takahashi et al., 1985a). Hydrolysis in a series of buffers gave the following DT50 values at 25 °C: pH 7, >2 years; pH 9, 8 days; pH 10, <1 day. A base-catalysed process operates above pH 7. Products detected were 2,2,3,3-tetramethylcyclopropanecarboxylic acid (TMCA, 2), 3PBAl(3) and the amide (4) (Scheme 1). Fenpropathrin (labelled as above) was subject to slow photodegradation in sunlight under various conditions with the following initial halflives: distilled water, >6 weeks; humic acid solution, 6 weeks; river water, 2.7 weeks; sea water, 1.6 weeks; 2% aqueous acetone, 0.5 day. Half-lives on three soils ranged from 1 to 5 days and on mandarin orange leaves it was 6 days (Takahashi et al., 1985b). The major products were TMCA, the amide (4) and 2-(3-phenoxybenzyl)-2-(2,2,3,3-tetraethylcyclopropyl)- acetonitrile (5). The latter product appeared to be unique to aqueous photolysis. By far the major product found on soil surfaces was the amide (4) but this was also found under dark conditions and is mainly a thermal product. Many other minor products were detected indicating the occurrence of (i) hydroxylation at a methyl group, (ii) oxidation to 3PBA (7), (iii) 0-dephenylation to afford 3-hydroxybenzoic acid (8) and (iv) loss of CN as CO2,. After 14 days, about 50% of the applied radioactivity was bound to a high organic matter soil. This was photochemically-induced, as less than 2% was bound in the dark. More recent studies using a xenon lamp (Katagi, 1993) indicated that formation of the amide was most efficient under drier conditions. Increased moisture, particularly in soil containing acidic binding sites, favoured ester cleavage. Degradation in organic solvents and in thin films afforded similar results (Dureja, 1989). The pathways of photodegradation of fenpropathrin are illustrated in Scheme 1.

InChI:InChI=1/C22H23NO3/c1-20(2)21(3,4)22(20,19(24)25)18(14-23)15-9-8-12-17(13-15)26-16-10-6-5-7-11-16/h5-13,18H,1-4H3,(H,24,25)/p-1

Upstream product

• 39515-47-4 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile 
• 24303-61-5 2,2,3,3-tetramethylcyclopropanecarbonyl chloride 
• 110-95-2 N,N,N'N'-tetramethyl-1,3-propanediamine 
• 39515-51-0 3-Phenoxybenzaldehyde 
• 15641-58-4 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid 
• 56338-23-9 alpha-bromo-3-phenoxybenzeneacetonitrile 

Downstream Products

• 2033-89-8 3,4-dimethoxyphenol 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 50789-43-0 methyl 3-phenoxybenzoate 
• 39515-47-4 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile 
• 39515-51-0 3-Phenoxybenzaldehyde 
• 108-95-2 phenol 
• 15641-58-4 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid 

Relevant articles and documents

Method for fighting against arthropods destructive of crops and compositions therefor

The present invention relates to processes for controlling arthropods, particularly processes for controlling insects and especially processes for controlling insects which ravage crops, particularly rice crops or market-garden crops; as well as to processes for protecting crops, particularly rice crops or market-garden crops; as well as to processes directed towards improving the yield of the treated crops; as well as to compositions or products which may be used in such processes.

Development of an Enzyme-Linked Immunosorbent Assay for the Detection of the Pyrethroid Insecticide Fenpropathrin

A competitive enayme-linked immunosorbent assay (ELISA) was developed for the quantitative detection of fenpropathrin [(RS)-α-cyano-3-phenoxybenzyl-2,2,3,3-tetramethylcyclopropanecarboxylate]. Polyclonal antisera were isolated from rabbits immunized with two different fenpropathrin hapten conjugates. One hapten contained an amino function; the other contained a carboxyl group for conjugation to carrier proteins. Mollusk hemocyanins, thyroglobulin, and fetuin were used as carrier proteins. The antisera varied greatly in their affinities for fenpropathrin. A homologous assay system using the coating antigen format was the most sensitive. The IC50 for fenpropathrin was 20 μg/L, and the lower detection limit was 2.5 μg/L. Pyrethroids, such as phenothrin, permethrin, resmethrin, fenvalerate, deltamethrin, cyfluthrin, and cypermethrin, and the pyrethroid metabolites, 3-phenoxybenzoic acid and fenpropathrin acid, did not cross-react significantly in this assay. Ten percent acetone or methanol and a pH of 4 were determined to be optimum assay conditions. Various cationic, anionic, and nonionic detergents had no significant effect on the assay.

Pesticidal composition containing a microencapsulated organo-phosphorus or carbamate in a pyrethroid dispersion

An insecticidal and/or acaricidal and/or nematicidal composition having a rapid efficacy and residual activity which comprises a mixture of a poorly water-soluble organophosphorus insecticide and/or acaricide and/or nematicide and/or a poorly water-soluble carbamate insecticide and/or acaricide which have been microencapsulated in water-insoluble polymer coatings with a dispersing agent used in forming a microcapsule part, with a poorly water-soluble pyrethroid insecticide and/or acaricide emulsified or suspended in water with the above-mentioned dispersing agent used in forming a flowable part.

Macrocyclic plant acaricides

Compounds of the formula I STR1 in which either R is methyl and there is a double bond in the 9,10-position, or in which R is hydrogen and there is a single bond in the 9,10-position, are highly active against Acarina which damage plants.

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.

Preparation of esters

Certain alpha-cyano esters are prepared by reacting an acyl halide with an aldehyde in a substantially water-immiscible aprotic solvent and an aqueous solution of water-soluble cyanide salt in the presence of an amine or cryptate rate-promoting agent.

Preparation of esters

Certain alpha-cyano esters are prepared by reacting an acyl halide with an aldehyde in a substantially water-immiscible aprotic solvent and an aqueous solution of water-soluble cyanide salt in the presence of an amine or cryptate rate-promoting agent.

Method for controlling wood-damaging insects

A method for controlling insects harmful to wood comprising contacting the insect with a composition comprising a carboxylate of the formula: STR1 as an active ingredient.

Preparation of esters

Certain carboxylic acid esters also containing a cyano group are prepared by reacting an acid halide, an aldehyde and a water-soluble cyanide in the presence of one or more water-immiscible (cyclo)alkane solvents.