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.
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
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).
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. Give artificial respiration if
victim is not breathing. Do not use mouth-to-mouth method
if victim ingested or inhaled the substance; give artificial
respiration with the aid of a pocket mask equipped with a
one-way valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact, avoid
spreading material on unaffected skin. Keep victim warm
and quiet. Effects of exposure (inhalation, ingestion, or skin
contact) to substance may be delayed. Ensure that medical
personnel are aware of the material(s) involved and take precautions
to protect themselves. Do not induce vomiting
when formulations containing petroleum solvents are
ingested. Otherwise, give large quantities of water and
induce vomiting. Do not make an unconscious person vomit.
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.
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.
Uses
Bifenthrin controls foliar insect pests and some mites on a range of
crops including cereals, citrus, cotton, fruit and vegetables.
Uses
Insecticide, acaricide.
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.
Production Methods
Bifenthrin is synthesised through a multi-step process that constructs its pyrethroid ester structure without the use of solvents, enhancing both efficiency and environmental safety. The production begins by mixing 2-methyl-3-phenylbenzyl alcohol with a catalyst in a reaction vessel and heating until molten. Then, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane methyl halide is added dropwise under negative pressure. The reaction continues for 1–3 hours, after which the mixture is washed, allowed to settle, and separated to yield bifenthrin.
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®
Mechanism of action
Contact and stomach action with some residual effect. Sodium channel modulator.
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.
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).
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.
Pesticide Type
Insecticide; Acaricide
