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Fenvalerate

Fenvalerate Structure
CAS No.
51630-58-1
Chemical Name:
Fenvalerate
Synonyms
SANMARTON;fenkill;phenvalerate;DUFON;FENNY;ARFEN;fenkem;Tirade;Pydrin;S-5602
CBNumber:
CB7281563
Molecular Formula:
C25H22ClNO3
Molecular Weight:
419.9
MOL File:
51630-58-1.mol
Modify Date:
2024/7/2 8:55:16

Fenvalerate Properties

Melting point 54-59℃
Boiling point 300°C
Density d23 1.17
vapor pressure 1.92×10-5 Pa (20 °C)
refractive index nD20 1.5533
storage temp. Sealed in dry,2-8°C
solubility DMSO:1.0(Max Conc. mg/mL);2.38(Max Conc. mM)
DMF:30.0(Max Conc. mg/mL);71.44(Max Conc. mM)
Ethanol:5.0(Max Conc. mg/mL);11.91(Max Conc. mM)
form Solid
color Off-white to light yellow
Water Solubility Soluble in 100% ethanol (>25 mg/ml), water (0.001 g/L) at 20°C, and DMSO.
Merck 13,4038
BRN 2025982
NIST Chemistry Reference Benzeneacetic acid, 4-chloro-«alpha»-(1-methylethyl)-, cyano(3-phenoxyphenyl)methyl ester(51630-58-1)
IARC 3 (Vol. 53) 1991
EPA Substance Registry System Fenvalerate (51630-58-1)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS09
Signal word  Danger
Hazard statements  H301-H315-H319-H335-H410
Precautionary statements  P261-P264-P273-P301+P310-P302+P352-P305+P351+P338
Hazard Codes  T,N
Risk Statements  25-36/37/38-50/53-57
Safety Statements  26-45-60-61
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  CY1576350
HazardClass  6.1(b)
PackingGroup  III
HS Code  29269090
Toxicity LD50 orally in rats: 451 mg/kg (DMSO); >3200 mg/kg (aqueous suspension), Shell Technical Data Bulletin

Fenvalerate price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) F1428 Fenvalerate ≥97% 51630-58-1 25MG ₹14343.13 2022-06-14 Buy
Sigma-Aldrich(India) 45495 Fenvalerate PESTANAL?, analytical standard 51630-58-1 250MG ₹7826.48 2022-06-14 Buy
Product number Packaging Price Buy
F1428 25MG ₹14343.13 Buy
45495 250MG ₹7826.48 Buy

Fenvalerate Chemical Properties,Uses,Production

Description

Fenvalerate is a yellow-brown viscous liquid that is practically soluble in water. It is stable to moderate heat and light and is rapidly hydrolysed in basic environments (above pH 8). Fenvalerate is a racemic mixture of four stereoisomers in equal proportions owing to the presence of two chiral centres. It is a synthetic type II pyrethroid.
Fenvalerate is registered as an insecticide for a wide array of crop uses, as well as a termiticide and insect repellent.

Chemical Properties

It is an ester of 2-(4-chlorophenyl)-3-methylbutyric acid and alpha-cyano-3-phenoxybenzyl alcohol but lacks a cyclopropane ring. However, in terms of its insecticidal behaviour, it belongs to the pyrethroid insecticides. Technical grade fenvalerate is a yellow or brown viscous liquid having a specific gravity of 1.175 at 25°C. The vapour pressure is 0.037 mPa at 25°C, and it is relatively non-volatile. It is practically insoluble in water (approximately 2 μg/L) but soluble in organic solvents such as acetone, xylene, and kerosene. It is stable to light, heat, and moisture but unstable in alkaline media.

Uses

Fenvalerate controls a wide range of insect pests in fruit, vines, olives, hops, nuts, vegetables, cotton, oilseed rape, sunflowers, alfalfa, cereals, maize, sorghum, potatoes, beets, soyabeans, tobacco, sugar cane and ornamentals. It is also used in public health situations and in animal houses.

Definition

ChEBI: A carboxylic ester obtained by formal condensation between 2-(4-chlorophenyl)-3-methylbutyric acid and cyano(3-phenoxyphenyl)methanol.

General Description

A clear viscious yellow liquid with a mild odor. Used as broad spectrum insecticide.

Air & Water Reactions

Insoluble in water. Rapidly hydrolyzed by alkaline solution.

Reactivity Profile

A pyrethroid. Phenvalerate is an ester and nitrile. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. 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 carboxylic acids (or salts of carboxylic acids).

Hazard

Questionable carcinogen.

Contact allergens

Fenvalerate is an insecticide of the synthetic pyrethroid group, which induced sensitization in farmers.

Safety Profile

Poison by ingestion, intravenous, and intracerebral routes. Moderately toxic by skin contact.Experimental reproductive effects. Mutation data reported. Highly toxic to fish and bees. Corrosive, causes eye damage. A skin irritant. When heated to decomposition it emits toxic fumes of Cl-, NOx, and CN-. See also CYANIDE.

Potential Exposure

Fenvalerate is one of the most versatile synthetic pyrethroid insecticides. It is mostly used in agriculture and on cattle, but also in homes and gardens. It acts as a stomach poison against a wide variety of leaf and fruit eating such as bollworm fruit and shoot borers and aphids. Crops on which it is used include cotton, cauliflower, okra, vines and fruits. It is also used in public health and animal husbandry. It is effective against pests whose strains are resistant to organochlorine, organophosphorus, and carbamate insecticides. Not used in EU countries

Environmental Fate

Soil. Fenvalerate is moderately persistent in soil. The percentage of the initial dosage (1 ppm) remaining after 8 weeks of incubation in an organic and mineral soil were 58 and 12%, respectively, while in sterilized controls 100 and 91% remained, respectively (Chapman et al., 1981).
In a sugarcane runoff plot, fenvalerate was applied at a rate of 0.22 kg/ha 4 times each year in 1980 and 1981. Runoff losses in 1980 and 1981 were 0.08 and 0.56 of the applied amount, respectively (Smith et al., 1983).
Plant. Dislodgable residues of fenvalerate on cotton leaf 0, 24, 48, 72 and 96 hours after application (0.22 kg/ha) were 0.85, 0.36, 0.38, 0.28 and 0.28 μg/m2, respectively (Buck et al., 1980).
Surface Water. In an estuary, the half-life of fenvalerate was 27–42 days (Schimmel et al., 1983).
Chemical/Physical. Undergoes hydrolysis at the ester bond (Hartley and Kidd, 1987). Decomposes gradually at 150–300°C (Windholz et al., 1983) probably releasing toxic fumes of nitrogen and chlorine.

Metabolic pathway

After foliar treatment of 14C-fenvalerate on wheat plants, the amount of residual radioactivity in the grain and hull is below the limit of reliable measurement. Individual degradation products accounting for more than 1% of the applied radioactivity are not present in the foliage or straw. Important degradation pathways include decarboxylation and ester cleavage.

Shipping

UN3349 Pyrethroid pesticide, solid toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material. UN3352 Pyrethroid pesticide, liquid toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

ncompatible with oxidizers, chlorates nitrates, peroxides, sulfuric acid, caustics, ammonia, aliphatic amines, alkanolamines, isocyanates, alkylene oxides, epichlorohydrin. Moisture may cause hydrolysis or other forms of decomposition. Emulsifiable concentrate is corrosive

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

References

[1] http://www.toxipedia.org
[2] Y. Xia, Q. Bian, L. Xu, S. Cheng, L. Song, J. Liu, W. Wu, S. Wang and X. Wang, Genotoxic effects on human spermatozoa among pesticide factory workers exposed to fenvalerate, Toxicology, 2004, vol. 203, 49-60
[3] Terry R Roberts, David H Hutson, Philip W Lee, Peter H Nicholls and Jack R Plimmer, Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides, 1999

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ALPHA-CYANO-3-PHENOXYBENZYL-ALPHA-(4-CHLOROPHENYL)ISOVALERATE ALPHA-CYANO-3-PHENOXYBENZYL ALPHA-(4-CHLOROPHENYL)-ISO-VALORATE A-CYANO-3-PHENOXYBENZYL A-(4-CHLOROPHENYL)ISOVALERATE alpha-Cyano-3-phenoxybenzyl (1R-(1alpha(S*),3alpha))-3-(2,2-dichlorovi nyl)-2,2-dimethylcyclopropanecarboxylate ALPHA-CYANO-(3-PHENOXYPHENYL)METHYL-4-CHLORO-ALPHA-(1-METH. FENPROPONATE FENVELRATE FENVALARAT FENVALART SUMICIDIN20EC Fenvalerat Benzeneacetic acid, 4-chloro-.alpha.-(1-methylethyl)-, cyano (3-phenoxyphenyl)-methyl ester Fenvalerate (R,S)-.alpha.-Cyano-3-phenoxybenzyl(R,S)-2-(4-chlorophenyl)-3-methylbutyric ester 4-chloro-alpha-(1-methylethyl)-benzeneacetic aci cyano(3-phenoxyphenyl)meth Fenvalerate E.C. 4-CHLORO-A-(1-METHYLETHYL)BENZENEACETICACIDCYANO(3-PHENOXYPHENYL)METHYLESTER Fenvalerate & Esfenvalerate (Sum of RR & SS isomers) 4-chloro-alpha-(1-methylethyl)benzeneacetic acid cyano(3-phenoxyphenyl)methyl ester Fenvalerate & esfenvalerate (Sum of RS & SRisomers) (R,S)-α-cyano-m-phenoxybenzyl (R,S)-2-(4-chlorophenyl)-3-methyl brtyprate (RS)-alpha-cyano-3-phenoxybenzyl Fenvalerate, α-Cyano-3-phenoxybenzyl α-(4-chlorophenyl)isovalerate Fenvalerate ,99% 4-CHLORO-A-(1-METHYLETHYL)BENZENEACETIC ACIDYANO(3-PHENOXYPHENYL)METHYL ESTER Fenvalerate 250mg [51630-58-1] Fanvalerate 4-Chloro-α-(1-Methylethyl)benzeneacetic Acid Cyano(3-phenoxyphenyl)Methyl Ester (cyano(3-phenoxyphenyl)methyl-4-chloro-alpha-(1-methylethyl)phenylacetate) furitrothion goldcresttribute insectral oms-2000 sumibac sumicidin20e sumifleece sumitick (R,S)-.alpha.-Cyano-3-phenoxybenzyl(R,S)-2-(4-chlorophenyl)-3-methylbutyricester (rs)-alpha-cyano-3-phenoxybenzyl(rs)-2-(4-chlorophenyl)-3-methylbutyrate 4-chloro-alpha-(1-methylethyl)-benzeneaceticacicyano(3-phenoxyphenyl)meth 4-chloro-alpha-(1-methylethyl)-benzeneaceticacicyano(3-phenoxyphenyl)methylester 4-chloro-alpha-(1-methylethyl)benzeneaceticacid,cyano(3-phenoxyphenyl)methyl 4-chloro-alpha-(1-methylethyl)benzeneaceticacidcyano(3-phenoxyphenyl)methyle agrofen alpha-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate alpha-Cyano-3-phenoxybenzyl-2-(4-chlorophenyl)-3-methylbutyrate alpha-cyano-3-phenoxybenzyl2-(4-chlorophenyl)-3-methylbutyrate alpha-cyano-3-phenoxybenzyl2-(4-chlorophenyl)isovalerate alpha-cyano-3-phenoxy-benzylalpha-isopropyl-4-chlorophenylacetate alpha-cyano-3-phenoxybenzylisopropyl-4-chlorophenylacetate aqmatrine balmark Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-, cyano(3-phenoxyphenyl)methyl ester Benzeneaceticacid,4-chloro-.alpha.-(1-methylethyl)-,cyano(3-phenoxyphenyl)-methylester Cyano(3-phenoxyphenyl)methyl4-chloro-(1-methylethyl)-benzeneacetate epashaughnessycode:109301 evercide2362 fenkem sumkidin Tirade tribute