Bifenthrin: Difference between revisions

| = changed

| verifiedrevid =

|ImageFile=Bifenthrin.

|ImageSize=

| ImageFile2 = Bifentrhin.png

| ImageSize2 = 300px

| PIN = ''rel''-(2-Methyl[1,1′-biphenyl]-3-yl)methyl (1''R'',3''R'')-3-[(1''Z'')-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate

| OtherNames =

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| PubChem=10938769

| KEGG_Ref = {{keggcite||kegg}}

| SMILES = Cc1c(cccc1c2ccccc2)COC(=O)C3C(C3(C)C)C=C(C(F)(F)F)Cl

|Section2={{Chembox Properties

| C=23|H=22|Cl=1|F=3|O=2

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=0.1 mg/L

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

'''Bifenthrin''' is a [[pyrethroid]] [[insecticide]] [[]].

It is not a restricted chemical in the United States and is commonly sold in hardware stores to control pests in homes.

Bifenthrin is in water . in soil between 7 days and 8 months , the longest residual on the market.

It is a white, waxy solid with a faint sweet smell. It is chemically synthesized in various forms, including powder, granules and pellets. However, it is not naturally occurring.<ref name="Toxipedia" />

Like other pyrethroids, bifenthrin is chiral; it has different [[enantiomers]] which can have different effects. Bifenthrin is found in two enantiomers: 1S-cis-bifenthrin and 1R-cis-bifenthrin. 1S-cis-Bifenthrin is 3-4 times more toxic to humans than 1R-cis-bifenthrin, while the latter is more than 300 times more effective as a pesticide.<ref name="enantiomer">{{cite journal| doi=10.1016/j.tox.2008.08.015 | pmid=18822338 | volume=253 | issue=1–3 | title=Enantioselective cytotoxicity of the insecticide bifenthrin on a human amnion epithelial (FL) cell line | year=2008 | journal=Toxicology | pages=89–96 | author=Liu Huigang, Zhao Meirong, Zhang Cong, Ma Yun, Liu Weiping}}</ref>

==Toxicity==

===Toxicodynamics===

There are two types of pyrethroids: those with and without α-cyanogroup. The [[neurotoxicity]] of bifenthrin is based on the affinity to the voltage-gated [[sodium channel]]s (in insects as well as mammals). The pyrethroids with an α-cyanogroup block the sodium-channel permanently, causing the membrane to be permanently hyperpolarized. The resting potential will not be restored, and no further action potential can be generated. The pyrethroids without an α-cyanogroup, to which bifenthrin belongs, are only able to bind to the sodium channel transiently. This will result in after potentials and eventual continuous firing of axons. The resting potential is not affected by these pyrethroids.<ref name="enantiomer" />

Bifenthrin will open the sodium channel for a shorter period than other pyrethroids. The mechanism in mammals and invertebrates is not different, but the effect on mammals is much less due to higher body temperature, higher body volume, and lower affinity of bifenthrin to sodium channels.<ref name="Kinetics">{{cite journal| doi=10.1016/0048-3575(83)90025-1 | volume=20 | issue=2 | title=Kinetics of sodium channel modification as the basis for the variation in the nerve membrane effects of pyrethroids and DDT analogs | year=1983 | journal=Pesticide Biochemistry and Physiology | pages=203–216 | author=Lund Albert E., Narahashi Toshio}}</ref>

===Toxicokinetics===

Numerous studies have been conducted on the half life of bifenthrin in soil, water, and air under different conditions, such as aerobic or anaerobic, and at different temperatures and pH.<ref name="npic factsheet">[https://web.archive.org/web/20150513043221/http://npic.orst.edu/factsheets/biftech.pdf], Bifenthrin Technical Fact Sheet, NPIC</ref> It is more likely to remain in the soil and not so much in water (it is hydrophobic), nor in the air (it is unlikely to volatilize because of its physical properties). Because of the water-insolubility of bifenthrin, it will not rapidly cause contamination of ground water. However, some contamination might occur by soil bound bifenthrin to surface water through runoff. For an overview of the environmental degradation of bifenthrin, see figure below. The main path of degradation results in 4’-hydroxy bifenthrin.

<!-- Deleted image removed: [[File:Environmental degradation of Bifenthrin.png]] -->

====Biotransformation====

Pyrethroids are much less toxic in mammals than they are in insects and fish, because mammals have the ability to rapidly break the ester bond in bifenthrin and break the substance into its inactive acid and alcohol components.<ref name="enantiomer" /> In humans and rats, bifenthrin is degraded by the [[cytochrome p450]]-family.<ref name="metabolism">[https://archive.today/20130414075331/http://dmd.aspetjournals.org/content/37/1/221.full.pdt+html], In Vitro Metabolism of Pyrethroid Pesticides by Rat and Human Hepatic Microsomes and Cytochrome P450 Isoforms</ref>

====

====Toxicity in animals====

;'''Mosquitoes'''

Bifenthrin is an effective pesticide to use against malaria and filaria vector mosquitoes. It is still effective when a resistance to other pyrethroids is found. Mosquito nets and indoor walls can be treated with bifenthrin<ref>{{cite journal|last=Al-Amin|journal=Terrestrial Arthropod Reviews|year=2011|volume=4|issue=3|doi=10.1163/187498311X577405|title=Evaluation of Bifenthrin 80 SC, as a wall treatment against ''Culex quinquefasciatus'' Say (Diptera: Culicidae), a vector of ''Wuchereria bancrofti'' Cobbold, an etiological agent of Human Lymphatic Filariasis|pages=183–202}}</ref> to keep more mosquitoes away.<ref name="mosquito">[http://www.bioone.org/doi/full/10.1603/0022-2585-39.3.526], Bifenthrin: A Useful Pyrethroid Insecticide for Treatment of Mosquito Nets</ref>

Bifenthrin is an effectively used insecticide, but the risk is high of it working only for a short time. Mosquitoes can develop a resistance to it, as well.<ref name="Malaria">[http://www.malariajournal.com/content/5/1/77], Efficacy of bifenthrin-impregnated bednets against Anopheles funestus and pyrethroid-resistant Anopheles gambiae in North Cameroon</ref>

;'''Aquatic life'''

Bifenthrin is hardly soluble in water, so nearly all bifenthrin will stay in the sediment, but it is very harmful to aquatic life. Even in small concentrations, fish and other aquatic animals are affected by bifenthrin.<ref name="npic factsheet" /> One of the reasons for the high sensitivity of fish is fish have a slow metabolism. Bifenthrin will stay longer in the system of the fish. Another reason for the high sensitivity of fish is the effect of bifenthrin as ATPase-inhibitor. The gills need ATP to control the osmotic balance of oxygen. If the fish is no longer capable of taking up oxygen because ATP can no longer be used, the fish will die.<ref name="extoxnet">[http://extoxnet.orst.edu/pips/bifenthr.htm], Extension Toxicology Network</ref>

In cold water, bifenthrin is even more dangerous. pH and calcium concentration are also factors that influence the toxicity.<ref name="rainbow trout">[http://www.agriculturejournals.cz/publicFiles/05521.pdf], Effects of acute exposure to bifenthrin on some haematological, biochemical and histopathological parameters of rainbow trout (''Oncorhynchus mykiss'')</ref>

Vertebrates are less sensitive to the effects of bifenthrin as ATPase-inhibitor.

;'''Bees'''

In bees, the lethal concentration ([[LC50|LC₅₀]]) of bifenthrin is about 17&nbsp;mg/L.<ref name="bees">{{cite journal | doi = 10.1002/etc.67 | title = Effects of sublethal concentrations of bifenthrin and deltamethrin on fecundity, growth, and development of the honeybeeApis mellifera ligustica | year = 2010 | last1 = Dai | first1 = Ping-Li | last2 = Wang | first2 = Qiang | last3 = Sun | first3 = Ji-Hu | last4 = Liu | first4 = Feng | last5 = Wang | first5 = Xing | last6 = Wu | first6 = Yan-Yan | last7 = Zhou | first7 = Ting | journal = Environmental Toxicology and Chemistry | volume = 29 | issue = 3 | pages = 644–9 | pmid = 20821489| s2cid = 21329904 }}</ref> At sublethal concentrations, bifenthrin reduces the [[fecundity]] of bees, decreases the rate at which bee larvae develop into adults, and increases their immature periods.<ref name="bees"/>

;'''Table of LD₅₀ values'''<ref name="npic factsheet" />

{| class="wikitable"

|-

! Species

! LD₅₀

|-

| Female rats

| 54&nbsp;mg/kg

|-

| Male rats

| 70&nbsp;mg/kg

|-

| Mice

| 43&nbsp;mg/kg

|-

| Mallard ducks

| 2150 mg/kg

|-

| Bobwhite quail

| 1800 mg/kg

|-

| Rainbow trout

| 0.00015&nbsp;mg/L

|-

| Bluegill

| 0.00035&nbsp;mg/L

|-

| Daphnia

| 0.0016&nbsp;mg/L

|}

====Toxicity in humans====

Bifenthrin and other synthetic pyrethroids are being used in agriculture in increasing amounts because of the high efficiency of these substances in killing insects, the low toxicity for mammals, and good biodegradability. However, because of its success, they are being used more often (also indoors) and high exposure of bifenthrin to humans can occur.{{medcn|date=February 2015}}

=====Carcinogenicity=====

The U.S. EPA classified bifenthrin as a Category C, possible human [[carcinogen]]. This rating is based on an increased rate of urinary bladder tumors in mice, adenoma and adenocarcinoma of the liver in male mice, and bronchoalveolar adenomas and adenocarcinomas of the lung in some female mice.<ref>{{cite web |url=http://npic.orst.edu/factsheets/biftech.pdf |title=National Pesticide Information Center: Bifenthrin Technical Information Fact Sheet |access-date=2015-02-09 }}</ref>

=====Potential for neurotoxicity=====

Bifenthrin can be absorbed by humans either by skin contact or ingestion. Skin contact is not toxic, causing only a slight tingling sensation at the point of contact. Ingestion in concentrations below 10⁻⁴ [[molarity|M]] is not toxic. However, commercially available bifenthrin products formulated for household use (such as Ortho Home Defense Max, sold as a liquid pump spray), can induce toxic effects due to ''other'' chemicals added to improve the sustainability of bifenthrin{{which|date=June 2020}} or are toxic on their own.{{which|date=June 2020}} Symptoms of excessive exposure are nausea, headaches, hypersensitivity for touch and sound, and irritation of the skin and the eyes.<ref name="pesticide">[http://www.panna.org/], Pesticide Action Network</ref>

==Regulation==

The [[United States Environmental Protection Agency|EPA]] monitors and regulates the use of pesticides in the United States. Because of its high toxicity to aquatic organisms, bifenthrin is classified as a restricted-use pesticide, meaning it may only be sold to certified pesticide applicators. However, the EPA allows lower concentrations of bifenthrin to be sold to the general public.

Bifenthrin has been approved for use against the [[Rasberry crazy ant]] in the Houston, Texas, area, under a special "crisis exemption" from the Texas Department of Agriculture and the EPA. The chemical is only approved for use in Texas counties experiencing "confirmed infestations" of the newly imported, invasive ant species.<ref name="entomology">[http://urbanentomology.tamu.edu/urban-pests/ants/rasberry/], Urban Entomology</ref>

The EPA has classified bifenthrin as a class C carcinogen, a possible human carcinogen based on a test with mice, which showed increased development of certain tumors.<ref name="npic factsheet" />

An acute and chronic reference dose (RfD) for bifenthrin has been established, based on animal studies. The reference dose resembles the estimated quantity of a chemical which a person could be exposed to every day (or a one-time exposure for the acute RfD) without any appreciable risk of adverse health effects. The acute reference dose (RfD) for bifenthrin is 0.328&nbsp;mg/kg bodyweight/day.

The chronic reference dose (RfD) for bifenthrin is 0.013&nbsp;mg/kg bodyweight/day.<ref name="npic factsheet" />

Bifenthrin was included in a biocide ban proposed by the Swedish Chemicals Agency, because of its carcinogenic effect.<ref name="kemi">[http://www.kemi.se/Documents/Bekampningsmedel/Vaxtskyddsmedel/List%20of%20substances%20banned%20or%20severily%20restricted%20in%20Sweden%201965-2000.pdf] {{Webarchive|url=https://web.archive.org/web/20130530003920/http://kemi.se/Documents/Bekampningsmedel/Vaxtskyddsmedel/List%20of%20substances%20banned%20or%20severily%20restricted%20in%20Sweden%201965-2000.pdf|date=2013-05-30}}, List of active substances in plant protection products which have been banned or withdrawn in Sweden during the period 1966 to 2000.</ref> This was approved by the European Parliament in 2009.<ref name="europarlement">{{Cite web|url=http://www.europarl.europa.eu/sides/getDoc.do?language=en&type=IM-PRESS&reference=20090112IPR45936|title = Pesticides legislation approved}}</ref>

Pesticides containing bifenthrin were withdrawn from use in the European Union.<ref name="eucouncil">{{Cite web|url=http://news.agropages.com/News/NewsDetail---1433.htm|title = EU Council bans three pesticides}}</ref> They have since been reinstated.<ref name="eucouncil2">{{cite web| url = http://www.bizjournals.com/philadelphia/blog/natalie-kostelni/2012/07/bifenthrin-is-back-european-union.html| url-status = dead| archive-url = https://web.archive.org/web/20120724010603/http://www.bizjournals.com/philadelphia/blog/natalie-kostelni/2012/07/bifenthrin-is-back-european-union.html| archive-date = 2012-07-24| title = Bifenthrin is back: European Union reapproves FMC insecticide - Philadelphia Business Journal}} </ref>

Bifenthrin is banned for agricultural use in European union countries since July 2019<ref>{{Cite web |title=EU Pesticides Database |url=https://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/start/screen/active-substances/details/460 |access-date=2023-10-24 |website=ec.europa.eu}}</ref> but is still approved for the preservation of chopped wood.

==Use==

On a large scale, bifenthrin is often used against invasive red [[red imported fire ant|fire ants]]. It is also effective against aphids, worms, other ants, gnats, moths, beetles, earwigs, grasshoppers, mites, midges, spiders, ticks, yellow jackets, maggots, thrips, caterpillars, flies, fleas, spotted lanternflies<ref>{{Cite web|title=Spotted Lanternfly Management for Residents|url=https://extension.psu.edu/spotted-lanternfly-management-for-residents|access-date=2020-10-01|website=Penn State Extension|language=en}}</ref> and termites. It is mostly used in orchards, nurseries, and homes. In the agricultural sector, it is used in great amounts on certain crops, such as corn. About 70% of all hops and raspberries cultured in the United States are treated with bifenthrin.<ref name="Toxipedia" />

Bifenthrin is used by the textile industry to protect woollen products from insect attack. It was introduced as an alternative to permethrin-based agents, due to greater efficacy against keratinophagous insects, better wash-fastness, and lower aquatic toxicity.<ref>{{cite journal | author = Ingham P. E., McNeil S. J., Sunderland M. R. | year = 2012 | title = Functional finishes for wool – Eco considerations | journal = Advanced Materials Research | volume = 441 | pages = 33–43 | doi=10.4028/www.scientific.net/amr.441.33| s2cid = 136607213 }}</ref>

===Products===

Products containing bifenthrin include Sevin, Transport, Talstar, Maxxthor, Biforce, Capture, Brigade, Bifenthrine, DuoCide insect control, Ortho Home Defense Max, Bifen XTS, Bifen IT, Bifen L/P, Torant, Zipak, Scotts Turf Builder SummerGuard, Wisdom TC Flowable, FMC 54800, Allectus, Ortho Max Pro and OMS3024 and mega wash from green planet and in Australia, Fortune Ultra, Hovex Ultra Low Odor and Surefire Fivestar.<ref name="Toxipedia">[https://web.archive.org/web/20180326214954/http://toxipedia.org/display/toxipedia/Bifenthrin], Toxipedia</ref>

==References==

==External links==

*[http://npic.orst.edu/factsheets/. - National Pesticide Information Center]

* {{PPDB|78}}

{{Insecticides}}

[[Category:Benzyl 2,2,3-trimethylcyclopropane-1-carboxylates]]

[[Category:Trifluoromethyl compounds]]

[[Category:FMC Corporation]]

[[:]]