Bifenthrin

Description

Bifenthrin is synthetic pyrethroid insecticide with biochemical origins in the natural insecticide pyrethrum. It is a waxy solid with a color ranging from an off-white to a pale tan, and with a slightly sweet odor. It is almost insoluble in water. Bifenthrin is used for the control of borers and termites in timber, insect pests in agricultural crops (bananas, apples, pears, ornamentals) and turf, as well as for general pest control (spiders, ants, fleas, flies, mosquitoes). Due to its high toxicity to aquatic organisms, it is listed as a restricted use pesticide. It has a very low solubility in water and tends to bind to soil, which minimizes runoff into water sources. It is marketed as Talstar, Bifenthrine, Brigade, Capture, Torant, Zipak, FMC 54800, and OMS3024.

References

[1] http://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/public/?event=activesubstance.detail&language=DE&selectedID=1026
[2] http://apvma.gov.au/node/12396
[3] http://www.ehrf.info/wp-content/uploads/2012/03/Bifenthrin-Feb-2012.pdf

Description

Bifenthrin is a synthetic pyrethroid insecticide/miticide/acaricide. Bifenthrin is off-white to pale tan waxy solid granules with a faint, musty odour and a slightly sweet smell. Bifenthrin is soluble in methylene chloride, acetone, chloroform, ether, and toluene and slightly soluble in heptane and methanol. It is slightly combustible and support combustion at elevated temperatures. Thermal decomposition and burning may form toxic byproducts such as carbon monoxide, carbon dioxide, hydrogen chloride, and hydrogen fluoride. Bifenthrin treatment affects the nervous system and causes paralysis in insects.

Chemical Properties

Bifenthrin is a member of the pyrethroid chemical class. It is an insecticide and acaricide. Bifenthrin is off-white to pale tan waxy solid granules with a faint, musty odor and slightly sweet smell. Bifenthrin is soluble in methylene chloride, acetone, chloroform, ether, and toluene, and is slightly soluble in heptane and methanol. It is slightly combustible and support combustion at elevated temperatures. Thermal decomposition and burning may form toxic by-products, such as carbon monoxide, carbon dioxide, hydrogen chloride, and hydrogen fl uoride. Bifentrin treatment affects the nervous system and causes paralysis in insects.

Chemical Properties

Off white to pale tan waxy substance. Faint, sweet odor.

Chemical Properties

White Solid

Uses

Bifenthrin controls foliar insect pests and some mites on a range of crops including cereals, citrus, cotton, fruit and vegetables.

Uses

Third generation synthetic pyrethroid. Insecticide, acaricide.

Definition

ChEBI: A carboxylic ester obtained by formal condensation of cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid and [(2-methyl-1,1'-biphenyl)-3-yl]methanol.

Health Hazard

Bifenthrin is moderately toxic to species of mammals when ingested. Exposures to large doses of bifenthrin cause poisoning with symptoms that include, but are not limited to, incoordination, tremor, salivation, vomiting, diarrhea, and irritability to sound and touch. Exposures to bifenthrin through skin absorption and/or inhalation of dust cause adverse health effects. On contact with bifenthrin, occupational workers develop adverse health effects that include skin sensations, rashes, numbness, and a burning and tingling type of effect. As a pyrethroid poison, bifenthrin disturbs the electrical impulses in nerves, over-stimulating nerve cells, causing tremors and eventually causing paralysis. The skin-related health effects were found to be reversible and subside after a brief period of time and stoppage of further exposures to bifenthrin. Although bifenthrin causes no infl ammation or irritation on human skin, it can cause a tingling sensation that lasts about 12 h. Bifenthrin has caused no symptoms of irritation to rabbits’ eyes. The US EPA has classifi ed bifenthrin as toxicity class II, meaning moderately toxic

Agricultural Uses

Insecticide, Acaricide: A broad-spectrum insecticide. Registered to control cone worms, seed bugs, seed worms and other insects and mites on rangeland, forests and right-of-ways. It is also used to control household and lawn pests. A U.S. EPA restricted Use Pesticide (RUP).

Trade name

BIFLEX®; BISTAR®; BRIGADE®; CAPTURE® Bifenthrin; DISCIPLINE®; DOUBLE THREAT®; EMPOWER®; FMC® 54800; FMC® 58000; TALSTAR®; TALSTAR LAWN & TREE®; TORANT®; ZIPAK®

Potential Exposure

A broad spectrum pyrethroid secticide/ acaricide used to control cone worms, seed bugs, seed worms and other insects and mites in forests, on rangeland, and right-of-ways. It is also used to control household and lawn pests. A United States Environmental Protection Agency Restricted Use Pesticide (RUP).

Metabolic pathway

When mites are administered 14C-bifenthrin either by injection or by contact, bifenthrin is efficiently metabolized by the mites and the metabolites identified arise from the combination of ester cleavage, oxidation, and conjugation reactions and are the 4'-hydroxy derivative of the ester, the primary ester cleavage products, the acid, and its 4'-hydroxy derivative from the alcohol moiety, as well as several unidentified metabolites.

storage

Bifenthrin should be kept stored in a cool, dry, well-ventilated place away from heat, open flame or hot surfaces. It should only be stored in its original containers and should not be contaminated with other pesticides, fertilizers, water, food, or feed by storage or disposal

Shipping

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required. UN3349 Pyrethroid pesticide, solid toxic, Hazard Class: 6.1; Labels: 6.1—Poisonous material.

Toxicity evaluation

The solubility of bifenthrin in water is relatively low at 0.1 mg l^-1. Furthermore, the water octanol coefficient (Kow) is 1×10⁶ and results in bifenthrin binding to organic substrates. The soil sorption coefficients range between 1.31×10⁵ and 3.02×10⁵, indicating relatively tight binding to soil particles. They also tend to bind to organic particulate materials in the water column. The Kow of bifenthrin may explain the bioconcentration factors (BCFs) observed in some animals, especially fish. For example, fathead minnows (Pimephales promelas) exposed to 0.0037 mg l1 bifenthrin had BCFs of 21 000 after 127 days and 28 000 after 254 days of exposure. Hydrolysis of bifenthrin in buffered water occurs between pH 5 and 9. Photolysis studies in water and soil found that the half-lives were 408 and 96.9 days, respectively. The aerobic soil half-life was 96.3 days and the anaerobic halflife, 425 days.

Degradation

Bifenthrin is stable for 21 days in the pH range 5-9 at 21°C but it is labile at higher pH. It has a DT₅₀ of 225 days in natural daylight and can therefore be regarded as relatively photochemically stable (PSD).

Incompatibilities

May react violently with strong oxidizers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders or dust. Incompatible with silver compounds, lime, and ordinary soaps. Mixture with some silver compounds forms explosive salts of silver oxalate.

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.