Fluxapyroxad

{{Use dmy dates|date=October 2014}} {{Chembox | ImageFile = Fluxapyroxad structure.svg | ImageSize = | ImageAlt = | PIN = 3-(Difluoromethyl)-1-methyl-''N''-(3′,4′,5′-trifluoro[1,1′-biphenyl]-2-yl)-1''H''-pyrazole-4-carboxamide<ref name="EPA-Factsheet" /> | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = 907204-31-3 | PubChem = 16095400 | ChemSpiderID = 17253690 | SMILES = CN1C=C(C(=N1)C(F)F)C(=O)NC2=CC=CC=C2C3=CC(=C(C(=C3)F)F)F | InChI = 1S/C18H12F5N3O/c1-26-8-11(16(25-26)17(22)23)18(27)24-14-5-3-2-4-10(14)9-6-12(19)15(21)13(20)7-9/h2-8,17H,1H3,(H,24,27) | InChIKey = SXSGXWCSHSVPGB-UHFFFAOYSA-N | UNII = 7U8P4NAR2S | ChEBI = 83113 }} | Section2 = {{Chembox Properties | C=18|H=12|F=5|N=3|O=1 | MolarMass = | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Fluxapyroxad''' is a broad-spectrum pyrazole-carboxamide fungicide used on a large variety of commercial crops.<ref name="Strathmann">{{Cite journal|author1=Strathmann, S. |author2=Walker, S. |author3=Barnes, J. |year=2011|title=Fluxapyroxad: A new broad-spectrum fungicide|journal=Phytopathology|volume=101|issue=6|page=172}}[http://www.apsnet.org/meetings/Documents/2011_Meeting_Abstracts/a11ma1008.htm abstract]</ref><ref name="Minnesota">{{Cite web|date=July 2012|title=Fluxapyroxad|work=New Active Ingredient Review|publisher=Minnesota Department of Agriculture |url=http://www.mda.state.mn.us/chemicals/pesticides/regs/~/media/7328555591A7441FA677AD52A7A80858.ashx|archiveurl=https://web.archive.org/web/20130625011931/http://www.mda.state.mn.us/chemicals/pesticides/regs/~/media/7328555591A7441FA677AD52A7A80858.ashx|archivedate=25 June 2013|url-status=live}}</ref> It stunts fungus growth by inhibiting the succinate dehydrogenase (SQR) enzyme.<ref name="Minnesota" /><ref>{{Cite web |last=BASF |first=Crop Protection |title= Xemium® for Seed Treatment |publisher= BASF Crop Protection |url= https://www.seedquest.com/id/b/basf/pdf/306842_BASF_Xemium_for_Seed_Brosch_AS05_final.pdf |archive-url= https://web.archive.org/web/20180623185144/https://www.seedquest.com/id/b/basf/pdf/306842_BASF_Xemium_for_Seed_Brosch_AS05_final.pdf |archive-date= 23 June 2018 |url-status= live |df=dmy}}</ref> Application of fluxapyroxad helps prevent many wilts and other fungal infections from taking hold. As with other systemic pesticides that have a long chemical half-life, there are concerns about keeping fluxapyroxad out of the groundwater, especially when combined with pyraclostrobin.<ref name="EPA-Factsheet">{{Cite web |author=Office of Chemical Safety and Pollution Prevention, United States Environmental Protection Agency|date=2 May 2012|title=Pesticide Fact Sheet: Fluxapyroxad|url=http://www.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-138009_02-May-12.pdf|archive-url=https://web.archive.org/web/20130708155945/http://epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-138009_02-May-12.pdf|archive-date=8 July 2013|url-status=dead}}</ref> There is also concern that some fungi may develop resistance to fluxapyroxad.<ref name="Resistance">{{Cite web|title=SDHI Fungicides|publisher=Fungicide Resistance Action Committee|url=http://www.frac.info/work/work_sdhi.htm|archiveurl=https://web.archive.org/web/20130622062708/http://www.frac.info/work/work_sdhi.htm|archivedate=22 June 2013|url-status=live}}</ref><ref>{{Cite journal|author1=Veloukas, Thomas |author2=Markoglou, Anastasios N. |author3=Karaoglanidis, George S. |year=2013|title=Differential Effect of SdhB Gene Mutations on the Sensitivity to SDHI Fungicides in Botrytis cinerea|journal=Plant Disease|volume=97|issue=1|pages=118&ndash;122|doi=10.1094/pdis-03-12-0322-re|doi-access=|pmid=30722271 |bibcode=2013PlDis..97..118V }} [http://cat.inist.fr/?aModele=afficheN&cpsidt=27199407 abstract]</ref>

==Chemical structure== The compound is an amide of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid combined with an aniline having an ortho-substituted triflurorobenzene group.<ref>{{cite book |doi=10.1002/9783527693931.ch31 |chapter=Fungicidal Succinate-Dehydrogenase-Inhibiting Carboxamides |title=Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals |year=2016 |last1=Walter |first1=Harald |editor-last1=Lamberth |editor-first1=Clemens |editor-first2=Jürgen |editor-last2= Dinges |publisher=Wiley |pages=405–425 |isbn=9783527339471 }}</ref>

==Biological action== Fluxapyroxad is a succinate dehydrogenase inhibitor (SDHI).<ref name="Resistance" /> It interferes with a number of key fungal life functions, including spore germination, germ tube growth, appresoria formation and mycelium growth. Specifically it interferes with the production of succinate dehydrogenase, the complex II in the mitochondrial respiration chain, which in turn interferes with the tricarboxylic cycle and mitochondrial electron transport.<ref name="Strathmann" />

==Crops== Fluxapyroxad is commonly used as a fungicide for grains, row crops, vegetable crops, and fruit trees (pome and prunus), including:<ref name="CFR-Tolerances">{{Cite web|author=United States Environmental Protection Agency|date=26 February 2014|title=Fluxapyroxad; Pesticide Tolerances|work=Federal Register|url=https://www.federalregister.gov/articles/2014/02/26/2014-04164/fluxapyroxad-pesticide-tolerances}}</ref><ref>{{cite web|last=BASF |first=Crop Protection|title=Priaxor Fungicide Product Label, Specimen, NVA 2013-04-372-0088|url=http://www.cdms.net/LDat/ldAK6001.pdf|publisher=BASF Crop Protection|archiveurl=https://web.archive.org/web/20141025163629/http://www.cdms.net/LDat/ldAK6001.pdf|archivedate=25 October 2014|url-status=live}}</ref><ref>{{cite web|last=BASF|first=Crop Protection|title=Merivon Fungicide Product Sheet|url=http://www.cdms.net/LDat/ldAKA006.pdf|archiveurl=https://web.archive.org/web/20141025161243/http://www.cdms.net/LDat/ldAKA006.pdf|archivedate=25 October 2014|url-status=live}}</ref> {{columns-list|colwidth=30em|;;''Grains:''

*Barley<ref>Coating barley seed with fluxapyroxad increased germination due to reduced fungal activity. {{Cite journal|author=Marquet, Nicolas|year=2012|title=Nouvelles substances à la CIMA, la part belle aux SDHI|journal=Phytoma-La Défense des végétaux |volume=659|pages=31–34}} [http://cat.inist.fr/?aModele=afficheN&cpsidt=26684708 abstract]</ref> *Corn (all types) *Oats *Rice *Rye *Triticale *Wheat

;;''Row and vegetable crops:''

*Shelled peas and beans, both succulent and dried *Edible-pod legume vegetables *Fruiting vegetables (including tomatoes) *Oilseed crops (flax seed, rapeseed, safflower and sunflower) *Peanuts *Soybeans *Sugar beets *Tuberous and corm vegetables (potato)

;;''Fruit trees:''

*Apples *Crabapples *Oriental pears (''Pyrus pyrifolia'') *Pears *Apricots *Cherries (sweet and tart) *Nectarines *Peaches *Plums (all varieties)

;;''Nut trees''

* Almond * Pecan }}

==Fungal diseases== Fluxapyroxad provides protection against many fungal diseases.<ref>{{Cite web|title=In-Field Research Shows Disease Control, Yield Advantages of Priaxor Fungicide and Merivon Fungicide From BASF|date=27 March 2012|work=PMN Crop News|publisher=Plant Management Network |url=https://www.plantmanagementnetwork.org/pub/php/news/2012/Priaxor/|archiveurl=https://web.archive.org/web/20120428083058/http://www.plantmanagementnetwork.org/pub/php/news/2012/Priaxor|archivedate=28 April 2012 |url-status=live}}</ref> Studies have shown specific efficacy against diseases such as black point, Botrytis gray mold,<ref>{{Cite journal|author1=Amiri, A. |author2=Heath, S. M. |author3=Peres, N. A. |year=2012|title=Sensitivity of ''Botrytis cinerea'' field isolates to the novel succinate dehydrogenase inhibitors fluopyram, penthiopyrad, and fluxapyroxad |journal=Phytopathology|volume=102|issue=7 (supplement)|page=S4.4}} [http://www.apsnet.org/meetings/Documents/2012_Meeting_Abstracts/aps12abP235.htm Abstract]</ref> early blight,<ref>{{Cite journal|author=Gudmestad, Neil C.|year=2013|title=Prevalence and Impact of SDHI Fungicide Resistance in ''Alternaria solani'' |journal=Plant Disease |volume=97|issue=7|pages=952–960|doi=10.1094/PDIS-12-12-1176-RE|display-authors=etal|doi-access=|pmid=30722567 |bibcode=2013PlDis..97..952G }} [http://apsjournals.apsnet.org/doi/abs/10.1094/PDIS-12-12-1176-RE Abstract]</ref> and powdery mildew;<ref>{{Cite web|title=Powdery Mildew on Peaches|date=6 May 2011|work=Tree Fruit IPM Advisory|publisher=Utah State University|url=http://utahpests.usu.edu/ipm/htm/advisories/treefruit/articleID=12736#pm|archiveurl=https://web.archive.org/web/20110515175028/http://utahpests.usu.edu/IPM/htm/advisories/treefruit/articleID%3D12736#pm|archivedate=15 May 2011|url-status=live|df=dmy-all}}</ref> however, fluxapyroxad was found to have no efficacy against anthracnose on lentils.<ref>{{Cite web|author=Wunsch, Michael|title=Recommendations for optimizing the control of anthracnose on lentils with fungicides |publisher=NDSU Carrington Research Extension Center, North Dakota State University|url=http://www.ag.ndsu.edu/carringtonrec/documents/plantpathologyrd/noyeardocs/Mar4WCropPestLentilFungicides.pdf|archiveurl=https://web.archive.org/web/20141025191632/http://www.ag.ndsu.edu/carringtonrec/documents/plantpathologyrd/noyeardocs/Mar4WCropPestLentilFungicides.pdf|archivedate=25 October 2014|url-status=live}}</ref>

== Toxicity == Fluxapyroxad has a low toxicity for humans, slightly toxic after a single ingestion, and relatively non-toxic after single inhalation or topical skin contact. However, fluxapyroxad is highly toxic to fish, fresh-water and salt-water invertebrates, and to aquatic plants, as well as being toxic to small mammals.<ref name="Minnesota" /><ref>{{Cite web|title=Safety Data Sheet Priaxor (4.0)|date=29 September 2014|publisher=Crop Data Management Systems, Inc.|url=http://www.cdms.net/LDat/mpAK6010.pdf|archiveurl=https://web.archive.org/web/20141025222449/http://www.cdms.net/LDat/mpAK6010.pdf|archivedate=25 October 2014|url-status=live}}</ref><ref>{{Cite book|year=2014|chapter=Plant Disease Control|title=Guide to Field Crop Protection|location=Carman, Manitoba|publisher=Manitoba Agriculture, Food and Rural Development (MAFRD), Government of Manitoba|pages=307&ndash;452, page 352|url=https://www.gov.mb.ca/agriculture/crops/guides-and-publications/pubs/crop-protection-guide-disease.pdf|archiveurl=https://web.archive.org/web/20141025182308/http://www.gov.mb.ca/agriculture/crops/guides-and-publications/pubs/crop-protection-guide-disease.pdf|archivedate=25 October 2014|url-status=live}}</ref> The primary target organ for fluxapyroxad exposure is the liver.<ref name="CFR-Tolerances" /> ''As the dose or duration of exposure to fluxapyroxad increased, clinical chemistry changes related to liver function also occurred, followed by hepatocellular necrosis, neoplastic changes in the liver, and tumors.''<ref name="CFR-Tolerances" /> Fluxapyroxad was found "not likely" to be carcinogenic in humans and there was no evidence of neurotoxicity.<ref name="CFR-Tolerances" />

The United States Environmental Protection Agency has established tolerance amounts that are allowed to be present on consumer food. These range from 0.05&nbsp;ppm on almonds and pecans to 3.0&nbsp;ppm on leafy ''brassica'', and 15&nbsp;ppm on other leafy vegetables.<ref name="CFR-Tolerances" /> The EPA is currently considering reducing those tolerances.<ref>{{Cite web|date=2020-09-30|title=Receipt of a Pesticide Petition Filed for Residues of Pesticide Chemicals in or on Various Commodities (August 2020)|url=https://www.federalregister.gov/documents/2020/09/30/2020-21184/receipt-of-a-pesticide-petition-filed-for-residues-of-pesticide-chemicals-in-or-on-various|access-date=2020-09-30|website=Federal Register}}</ref>

==Registration and approval== Fluxapyroxad has been approved for use as a fungicide in the United States, Canada and the European Union.<ref>{{Cite web|title=BASF's new fungicide fluxapyroxad got EU approval|url=http://news.agropages.com/News/NewsDetail---7356.htm|archiveurl=https://web.archive.org/web/20120724123146/http://news.agropages.com/News/NewsDetail---7356.htm|archivedate=24 July 2012|url-status=live}}</ref> In the spring of 2012, fluxapyroxad, trademarked under the names '''Sercadis''',<ref>EPA Registration Number 7969-309</ref> '''Imbrex'''<ref>EPA Registration Number 7969-306</ref> and '''Xemium'''<ref>EPA Registration Number 7969-308</ref> and manufactured by BASF Corporation, was registered for use as a fungicide in the United States. Fluxapyroxad is also one of the two active ingredients in '''Priaxor''' fungicide and '''Merivon''' fungicide, the other active ingredient being a strobilurin called pyraclostrobin.<ref name="agproducts.basf">{{cite web|last=BASF|first=Newsroom|title=New Priaxor fungicide and Merivon fungicide now registered for use |work=BASF |url=https://www.basf.com/us/en/company/news-and-media/news-releases/2012/05/p-12-101.html |publisher=BASF Crop Protection |archive-url=https://web.archive.org/web/20180623183212/https://www.basf.com/us/en/company/news-and-media/news-releases/2012/05/p-12-101.html |archive-date=23 June 2018 |url-status=live |df=dmy}}</ref>

== References == {{Reflist}} {{Clear}}

{{DEFAULTSORT:Fluxapyroxad}} Category:Fungicides Category:Carboxamides Category:Pyrazoles Category:Fluoroarenes Category:Biphenyls