Tebufenpyrad infobox and Tebufenpyrad: Difference between pages

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 431792267

| Reference =<ref name=epa>[http://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-090102_26-Aug-02.pdf Tebufenpyrad Pesticide Fact Sheet] {{Webarchive|url=https://web.archive.org/web/20170910173516/https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-090102_26-Aug-02.pdf |date=2017-09-10 }}, [[U.S. Environmental Protection Agency]]</ref>

| Name = Tebufenpyrad

| ImageFile = Tebufenpyrad.svg

| ImageSize = 220

| ImageAlt = Skeletal formula of tebufenpyrad

| ImageFile1 = Tebufenpyrad-3D-spacefill.png

| ImageSize1 = 220

| ImageAlt1 = Space-filling model of the tebufenpyrad molecule

| PIN =''N''-[(4-''tert''-Butylphenyl)methyl]-4-chloro-3-ethyl-1-methyl-1''H''-pyrazole-5-carboxamide

| OtherNames = 4-Chloro-''N''-<nowiki>[[</nowiki>4-(1,1-dimethylethyl)phenyl]]methyl]-3-ethyl-1-methyl-1''H''-pyrazole-5-carboxamide

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 119168-77-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = IRU3P7ZB3F

| PubChem = 86354

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 77872

| SMILES = CCc1c(c(n(n1)C)C(=O)NCc2ccc(cc2)C(C)(C)C)Cl

| InChI = 1/C18H24ClN3O/c1-6-14-15(19)16(22(5)21-14)17(23)20-11-12-7-9-13(10-8-12)18(2,3)4/h7-10H,6,11H2,1-5H3,(H,20,23)

| InChIKey = ZZYSLNWGKKDOML-UHFFFAOYAB

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C18H24ClN3O/c1-6-14-15(19)16(22(5)21-14)17(23)20-11-12-7-9-13(10-8-12)18(2,3)4/h7-10H,6,11H2,1-5H3,(H,20,23)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZZYSLNWGKKDOML-UHFFFAOYSA-N

|Section2={{Chembox Properties

| Appearance = White crystalline solid

| C=18 | H=24 | Cl=1 | N=3 | O=1

| MeltingPtC = 64 to 66

| MeltingPt_notes =

| Density = 0.5 g/mL at 24.1 °C

| Solubility = 2.61 ppm at pH 5.9<br />3.21 ppm at pH 4<br />2.39 ppm at pH 7<br />2.32 ppm at pH 10

| pKa = 5.9 in water

'''Tebufenpyrad''' is an [[insecticide]] and [[acaricide]] widely used in [[greenhouse]]s. It is a white solid chemical with a slight aromatic smell. It is soluble in water and also in organic solvents.<ref name="toxnet.nlm.nih.gov">http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+7271 {{dead link|date=October 2021}}</ref>

==Mode of action==

Tebufenpyrad is a strong [[NADH:ubiquinone reductase (H+-translocating)|mitochondrial complex I]] inhibitor. Like [[Rotenone]], it inhibits electron transport chain by inhibiting the complex I enzymes of mitochondria which ultimately leads to lack of [[Adenosine triphosphate|ATP]] production and finally cell death.

==Use==

Tebufenpyrad is used mainly in greenhouses around the world. It has been registered under various trade names (i.e.Masai, Pyranica)<ref name="Ed.2012">{{cite book|author=Richard T. Meister, Ed.|title=Crop Protection Handbook 2012: The Essential Desktop Reference for Plant Health Experts|url=https://books.google.com/books?id=PcFQtwAACAAJ|volume=98|date=January 2012|publisher=Meister Publishing Company|isbn=978-1-892829-25-2|page=665}}</ref> in countries like [[Australia]], [[China]] and certain [[South America|South American]] countries. It is registered in [[United States|USA]] for use on ornamental plants in commercial green houses.<ref name=epa/>{{rp|1}} The data available presented enough evidence to support unconditional registration of tebufenpyrad for use on ornamental plants in greenhouses.<ref name=epa/>{{rp|13}}

==Exposure and toxicity==

It is mainly used in greenhouses and the major form of exposure is through occupational exposure where this chemical is manufactured or used extensively. The possible routes of exposure are through inhalation or dermal exposure.<ref name="toxnet.nlm.nih.gov"/> Since it is used in ornamental plants the exposure through food is limited.

The LD 50 values for various laboratory animals are as follows:

[[LD50]] Rat (male) oral 595&nbsp;mg/kg

LD50 Rat (female) oral 997&nbsp;mg/kg

LD50 Mouse (male) oral 224&nbsp;mg/kg

LD50 Mouse (female) oral 210&nbsp;mg/kg

LD50 Rat dermal >2000&nbsp;mg/kg<ref name="MacBean C 2012">MacBean C, ed. Tebufenpyrad (119168-77-3). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2011–2012). Surrey UK, British Crop Protection Council</ref>

==Biotransformation==

[[Hydroxylation]] is the major and primary [[biotransformation]] of tebufenpyrad reported both ''in vivo'' and ''in vitro''. Ethyl and tert.-butyl groups are the targets of hydroxylation. The alcohol groups are oxidized to carboxylic groups which can then be conjugated with other groups ''in vivo''.<ref>{{cite book|last1=Casarett|first1=Louis|last2=Doull|first2=John|last3=Klaassen|first3=Curtis|title=Casarett and Doull's Toxicology: The Basic Science of Poisons|url=https://books.google.com/books?id=2yl9jgEACAAJ|edition=6th|year=2001|publisher=McGraw Hill Professional|isbn=978-0-07-112453-9|page=1193}}</ref>

In [[animal testing on rodents|rodent studies]] it was shown that 80% of the [[pesticide]] was absorbed mainly in the digestive system within 24 hours, the major metabolites being the hydroxylated forms. Most of the compound and its metabolites were excreted through feces and urine. There was no evidence of accumulation in the body of the rodents.<ref name=epa/>{{rp|11}}

The metabolites excreted out differed from male to female in rodents. While males excreted the carboxylic derivatives of the parent compound, the female rats excreted the sulfate conjugates of carboxylic acid. The [[LD50]] values of male and female rats was very different. While the LD50 value of female rats was 997&nbsp;mg/kg the LD50 for male rats was only 595&nbsp;mg/kg.<ref name="MacBean C 2012"/> This vast difference in LD 50 value might be attributed to this [[biotransformation]].

==Consequences of exposure==

Tebufenpyrad exposure has been linked to cancer but to date no human data has been conclusive enough to link the two.<ref>USEPA Office of Pesticide Programs, Health Effects Division, Science Information Management Branch: "Chemicals Evaluated for Carcinogenic Potential" (April 2006)</ref>

Recently this pesticide has been shown to affect the dopaminergic neuronal cell lines N27 by disrupting the mitochondrial dynamics. Loss of dopaminergic cells have been linked to [[Parkinson's disease]] in which the neuronal mitochondria are affected.<ref name="CharliJin2015">{{cite journal|last1=Charli|first1=Adhithiya|last2=Jin|first2=Huajun|last3=Anantharam|first3=Vellareddy|last4=Kanthasamy|first4=Arthi|last5=Kanthasamy|first5=Anumantha G.|title=Alterations in mitochondrial dynamics induced by tebufenpyrad and pyridaben in a dopaminergic neuronal cell culture model|journal=NeuroToxicology|year=2015|issn=0161-813X|doi=10.1016/j.neuro.2015.06.007|pmc=4698251|pmid=26141520|volume=53|pages=302–313}}</ref> These findings may show that tebufenpyrad might also be able to affect the neurons.

Overexposure of the pesticide has also led to the development of resistance among different target organisms.<ref name="AugerBonafos2003">{{cite journal|last1=Auger|first1=Philippe|last2=Bonafos|first2=Romain|last3=Guichou|first3=Sabine|last4=Kreiter|first4=Serge|title=Resistance to fenazaquin and tebufenpyrad in Panonychus ulmi Koch (Acari: Tetranychidae) populations from South of France apple orchards|journal=Crop Protection|volume=22|issue=8|year=2003|pages=1039–1044|issn=0261-2194|doi=10.1016/S0261-2194(03)00136-4|bibcode=2003CrPro..22.1039A }}</ref> Recent studies have detected tebufenpyrad resistance in two [[spider mite]] species in [[apple trees]] in Western Australia.<ref name="HerronRophail1998">{{cite journal|last1=Herron|first1=G.A.|last2=Rophail|first2=J.|title=Tebufenpyrad (Pyranica®) resistance detected in two-spotted spider mite Tetranychus urticae Koch (Acari: Tetranychidae) from apples in Western Australia|journal=Experimental & Applied Acarology|volume=22|issue=11|year=1998|pages=633–641|issn=0168-8162|doi=10.1023/A:1006058705429|s2cid=24115663}}</ref>

==References==

{{Reflist}}

[[Category:Insecticides]]

[[Category:Acaricides]]

[[Category:Pyrazoles]]

[[Category:Tert-butyl compounds]]