Fluxapyroxad is a broad-spectrum pyrazole-carboxamidefungicide used on a large variety of commercial crops.[2][3] It stunts fungus growth by inhibiting the succinate dehydrogenase (SQR) enzyme.[3][4] 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.[1] There is also concern that some fungi may develop resistance to fluxapyroxad.[5][6]
Fluxapyroxad is a succinate dehydrogenase inhibitor (SDHI).[5] 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.[2]
Cropsedit
Fluxapyroxad is commonly used as a fungicide for grains, row crops, vegetable crops, and fruit trees (pome and prunus), including:[8][9][10]
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.[3][17][18] The primary target organ for fluxapyroxad exposure is the liver.[8]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.[8] Fluxapyroxad was found "not likely" to be carcinogenic in humans and there was no evidence of neurotoxicity.[8]
The United States Environmental Protection Agency has established tolerance amounts that are allowed to be present on consumer food. These range from 0.05 ppm on almonds and pecans to 3.0 ppm on leafy brassica, and 15 ppm on other leafy vegetables.[8] The EPA is currently considering reducing those tolerances.[19]
Registration and approvaledit
Fluxapyroxad has been approved for use as a fungicide in the United States, Canada and the European Union.[20] In the spring of 2012, fluxapyroxad, trademarked under the names Sercadis,[21]Imbrex[22] and Xemium[23] 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.[24]
Referencesedit
^ abOffice of Chemical Safety and Pollution Prevention, United States Environmental Protection Agency (2 May 2012). "Pesticide Fact Sheet: Fluxapyroxad" (PDF). (PDF) from the original on 8 July 2013.
^ abStrathmann, S.; Walker, S.; Barnes, J. (2011). "Fluxapyroxad: A new broad-spectrum fungicide". Phytopathology. 101 (6): 172.abstract
^ abc"Fluxapyroxad". New Active Ingredient Review. Minnesota Department of Agriculture. July 2012. from the original on 25 June 2013.
^BASF, Crop Protection. "Xemium® for Seed Treatment" (PDF). BASF Crop Protection. (PDF) from the original on 23 June 2018.
^ ab"SDHI Fungicides". Fungicide Resistance Action Committee. from the original on 22 June 2013.
^Veloukas, Thomas; Markoglou, Anastasios N.; Karaoglanidis, George S. (2013). "Differential Effect of SdhB Gene Mutations on the Sensitivity to SDHI Fungicides in Botrytis cinerea". Plant Disease. 97 (1): 118–122. doi:10.1094/pdis-03-12-0322-re. abstract
^Walter, Harald (2016). "Fungicidal Succinate-Dehydrogenase-Inhibiting Carboxamides". In Lamberth, Clemens; Dinges, Jürgen (eds.). Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals. Wiley. pp. 405–425. doi:10.1002/9783527693931.ch31. ISBN9783527339471.
^ abcdeUnited States Environmental Protection Agency (26 February 2014). "Fluxapyroxad; Pesticide Tolerances". Federal Register.
^BASF, Crop Protection. "Priaxor Fungicide Product Label, Specimen, NVA 2013-04-372-0088" (PDF). BASF Crop Protection. (PDF) from the original on 25 October 2014.
^BASF, Crop Protection. "Merivon Fungicide Product Sheet" (PDF). (PDF) from the original on 25 October 2014.
^Coating barley seed with fluxapyroxad increased germination due to reduced fungal activity. Marquet, Nicolas (2012). "Nouvelles substances à la CIMA, la part belle aux SDHI". Phytoma-La Défense des végétaux. 659: 31–34. abstract
^"In-Field Research Shows Disease Control, Yield Advantages of Priaxor Fungicide and Merivon Fungicide From BASF". PMN Crop News. Plant Management Network. 27 March 2012. from the original on 28 April 2012.
^Amiri, A.; Heath, S. M.; Peres, N. A. (2012). "Sensitivity of Botrytis cinerea field isolates to the novel succinate dehydrogenase inhibitors fluopyram, penthiopyrad, and fluxapyroxad". Phytopathology. 102 (7 (supplement)): S4.4. Abstract
^Gudmestad, Neil C.; et al. (2013). "Prevalence and Impact of SDHI Fungicide Resistance in Alternaria solani". Plant Disease. 97 (7): 952–960. doi:10.1094/PDIS-12-12-1176-RE. Abstract
^"Powdery Mildew on Peaches". Tree Fruit IPM Advisory. Utah State University. 6 May 2011. from the original on 15 May 2011.
^Wunsch, Michael. "Recommendations for optimizing the control of anthracnose on lentils with fungicides" (PDF). NDSU Carrington Research Extension Center, North Dakota State University. (PDF) from the original on 25 October 2014.
^"Safety Data Sheet Priaxor (4.0)" (PDF). Crop Data Management Systems, Inc. 29 September 2014. (PDF) from the original on 25 October 2014.
^"Plant Disease Control". Guide to Field Crop Protection(PDF). Carman, Manitoba: Manitoba Agriculture, Food and Rural Development (MAFRD), Government of Manitoba. 2014. pp. 307–452, page 352. (PDF) from the original on 25 October 2014.
^"Receipt of a Pesticide Petition Filed for Residues of Pesticide Chemicals in or on Various Commodities (August 2020)". Federal Register. 30 September 2020. Retrieved 30 September 2020.
^"BASF's new fungicide fluxapyroxad got EU approval". from the original on 24 July 2012.
^BASF, Newsroom. "New Priaxor fungicide and Merivon fungicide now registered for use". BASF Crop Protection. from the original on 23 June 2018.
January 01, 1970
fluxapyroxad, broad, spectrum, pyrazole, carboxamide, fungicide, used, large, variety, commercial, crops, stunts, fungus, growth, inhibiting, succinate, dehydrogenase, enzyme, application, fluxapyroxad, helps, prevent, many, wilts, other, fungal, infections, f. Fluxapyroxad is a broad spectrum pyrazole carboxamide fungicide used on a large variety of commercial crops 2 3 It stunts fungus growth by inhibiting the succinate dehydrogenase SQR enzyme 3 4 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 1 There is also concern that some fungi may develop resistance to fluxapyroxad 5 6 Fluxapyroxad Names Preferred IUPAC name 3 Difluoromethyl 1 methyl N 3 4 5 trifluoro 1 1 biphenyl 2 yl 1H pyrazole 4 carboxamide 1 Identifiers CAS Number 907204 31 3 3D model JSmol Interactive image ChEBI CHEBI 83113 ChemSpider 17253690 ECHA InfoCard 100 107 372 PubChem CID 16095400 UNII 7U8P4NAR2S CompTox Dashboard EPA DTXSID6058215 InChI 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 Key SXSGXWCSHSVPGB UHFFFAOYSA N SMILES CN1C C C N1 C F F C O NC2 CC CC C2C3 CC C C C3 F F F Properties Chemical formula C 18H 12F 5N 3O Molar mass 381 306 g mol 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Chemical structure 2 Biological action 3 Crops 4 Fungal diseases 5 Toxicity 6 Registration and approval 7 ReferencesChemical structure editThe compound is an amide of 3 difluoromethyl 1 methyl 1H pyrazole 4 carboxylic acid combined with an aniline having an ortho substituted triflurorobenzene group 7 Biological action editFluxapyroxad is a succinate dehydrogenase inhibitor SDHI 5 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 2 Crops editFluxapyroxad is commonly used as a fungicide for grains row crops vegetable crops and fruit trees pome and prunus including 8 9 10 Grains Barley 11 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 PecanFungal diseases editFluxapyroxad provides protection against many fungal diseases 12 Studies have shown specific efficacy against diseases such as black point Botrytis gray mold 13 early blight 14 and powdery mildew 15 however fluxapyroxad was found to have no efficacy against anthracnose on lentils 16 Toxicity editFluxapyroxad 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 3 17 18 The primary target organ for fluxapyroxad exposure is the liver 8 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 8 Fluxapyroxad was found not likely to be carcinogenic in humans and there was no evidence of neurotoxicity 8 The United States Environmental Protection Agency has established tolerance amounts that are allowed to be present on consumer food These range from 0 05 ppm on almonds and pecans to 3 0 ppm on leafy brassica and 15 ppm on other leafy vegetables 8 The EPA is currently considering reducing those tolerances 19 Registration and approval editFluxapyroxad has been approved for use as a fungicide in the United States Canada and the European Union 20 In the spring of 2012 fluxapyroxad trademarked under the names Sercadis 21 Imbrex 22 and Xemium 23 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 24 References edit a b Office of Chemical Safety and Pollution Prevention United States Environmental Protection Agency 2 May 2012 Pesticide Fact Sheet Fluxapyroxad PDF Archived PDF from the original on 8 July 2013 a b Strathmann S Walker S Barnes J 2011 Fluxapyroxad A new broad spectrum fungicide Phytopathology 101 6 172 abstract a b c Fluxapyroxad New Active Ingredient Review Minnesota Department of Agriculture July 2012 Archived from the original on 25 June 2013 BASF Crop Protection Xemium for Seed Treatment PDF BASF Crop Protection Archived PDF from the original on 23 June 2018 a b SDHI Fungicides Fungicide Resistance Action Committee Archived from the original on 22 June 2013 Veloukas Thomas Markoglou Anastasios N Karaoglanidis George S 2013 Differential Effect of SdhB Gene Mutations on the Sensitivity to SDHI Fungicides in Botrytis cinerea Plant Disease 97 1 118 122 doi 10 1094 pdis 03 12 0322 re abstract Walter Harald 2016 Fungicidal Succinate Dehydrogenase Inhibiting Carboxamides In Lamberth Clemens Dinges Jurgen eds Bioactive Carboxylic Compound Classes Pharmaceuticals and Agrochemicals Wiley pp 405 425 doi 10 1002 9783527693931 ch31 ISBN 9783527339471 a b c d e United States Environmental Protection Agency 26 February 2014 Fluxapyroxad Pesticide Tolerances Federal Register BASF Crop Protection Priaxor Fungicide Product Label Specimen NVA 2013 04 372 0088 PDF BASF Crop Protection Archived PDF from the original on 25 October 2014 BASF Crop Protection Merivon Fungicide Product Sheet PDF Archived PDF from the original on 25 October 2014 Coating barley seed with fluxapyroxad increased germination due to reduced fungal activity Marquet Nicolas 2012 Nouvelles substances a la CIMA la part belle aux SDHI Phytoma La Defense des vegetaux 659 31 34 abstract In Field Research Shows Disease Control Yield Advantages of Priaxor Fungicide and Merivon Fungicide From BASF PMN Crop News Plant Management Network 27 March 2012 Archived from the original on 28 April 2012 Amiri A Heath S M Peres N A 2012 Sensitivity of Botrytis cinerea field isolates to the novel succinate dehydrogenase inhibitors fluopyram penthiopyrad and fluxapyroxad Phytopathology 102 7 supplement S4 4 Abstract Gudmestad Neil C et al 2013 Prevalence and Impact of SDHI Fungicide Resistance in Alternaria solani Plant Disease 97 7 952 960 doi 10 1094 PDIS 12 12 1176 RE Abstract Powdery Mildew on Peaches Tree Fruit IPM Advisory Utah State University 6 May 2011 Archived from the original on 15 May 2011 Wunsch Michael Recommendations for optimizing the control of anthracnose on lentils with fungicides PDF NDSU Carrington Research Extension Center North Dakota State University Archived PDF from the original on 25 October 2014 Safety Data Sheet Priaxor 4 0 PDF Crop Data Management Systems Inc 29 September 2014 Archived PDF from the original on 25 October 2014 Plant Disease Control Guide to Field Crop Protection PDF Carman Manitoba Manitoba Agriculture Food and Rural Development MAFRD Government of Manitoba 2014 pp 307 452 page 352 Archived PDF from the original on 25 October 2014 Receipt of a Pesticide Petition Filed for Residues of Pesticide Chemicals in or on Various Commodities August 2020 Federal Register 30 September 2020 Retrieved 30 September 2020 BASF s new fungicide fluxapyroxad got EU approval Archived from the original on 24 July 2012 EPA Registration Number 7969 309 EPA Registration Number 7969 306 EPA Registration Number 7969 308 BASF Newsroom New Priaxor fungicide and Merivon fungicide now registered for use BASF Crop Protection Archived from the original on 23 June 2018 Retrieved from https en wikipedia org w index php title Fluxapyroxad amp oldid 1215485371, wikipedia, wiki, book, books, library,
