Fluxapyroxad

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Fluxapyroxad
Fluxapyroxad structure.svg
Names
Preferred IUPAC name
3-(Difluoromethyl)-1-methyl-N-(3′,4′,5′-trifluoro[1,1′-biphenyl]-2-yl)-1H-pyrazole-4-carboxamide [1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.107.372 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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
  • CN1C=C(C(=N1)C(F)F)C(=O)NC2=CC=CC=C2C3=CC(=C(C(=C3)F)F)F
Properties
C18H12F5N3O
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).

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]

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. [7]

Biological action

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]

Crops

Fluxapyroxad is commonly used as a fungicide for grains, row crops, vegetable crops, and fruit trees (pome and prunus), including: [8] [9] [10]

Grains:
Row and vegetable crops:
Fruit trees:
Nut trees

Fungal diseases

Fluxapyroxad 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

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 approval

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]

Related Research Articles

Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, and profit. Fungicides are used both in agriculture and to fight fungal infections in animals. Fungicides are also used to control oomycetes, which are not taxonomically/genetically fungi, although sharing similar methods of infecting plants. Fungicides can either be contact, translaminar or systemic. Contact fungicides are not taken up into the plant tissue and protect only the plant where the spray is deposited. Translaminar fungicides redistribute the fungicide from the upper, sprayed leaf surface to the lower, unsprayed surface. Systemic fungicides are taken up and redistributed through the xylem vessels. Few fungicides move to all parts of a plant. Some are locally systemic, and some move upward. Most fungicides that can be bought retail are sold in liquid form, the active ingredient being present at 0.08% in weaker concentrates, and as high as 0.5% for more potent fungicides. Fungicides in powdered form are usually around 90% sulfur.

<span class="mw-page-title-main">Succinate dehydrogenase</span> Enzyme

Succinate dehydrogenase (SDH) or succinate-coenzyme Q reductase (SQR) or respiratory complex II is an enzyme complex, found in many bacterial cells and in the inner mitochondrial membrane of eukaryotes. It is the only enzyme that participates in both the citric acid cycle and the electron transport chain. Histochemical analysis showing high succinate dehydrogenase in muscle demonstrates high mitochondrial content and high oxidative potential.

<span class="mw-page-title-main">Vinclozolin</span> Fungicide used on fruits and vegetables

Vinclozolin is a common dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards, and on fruits and vegetables such as raspberries, lettuce, kiwi, snap beans, and onions. It is also used on turf on golf courses. Two common fungi that vinclozolin is used to protect crops against are Botrytis cinerea and Sclerotinia sclerotiorum. First registered in 1981, vinclozolin is widely used but its overall application has declined. As a pesticide, vinclozolin is regulated by the United States Environmental Protection Agency. In addition to these restrictions within the United States, as of 2006 the use of this pesticide was banned in several countries, including Denmark, Finland, Norway, and Sweden. It has gone through a series of tests and regulations in order to evaluate the risks and hazards to the environment and animals. Among the research, a main finding is that vinclozolin has been shown to be an endocrine disruptor with antiandrogenic effects.

<span class="mw-page-title-main">Iprodione</span> Chemical compound

Iprodione is a hydantoin fungicide and nematicide.

The cereal grain wheat is subject to numerous wheat diseases, including bacterial, viral and fungal diseases, as well as parasitic infestations.

Acibenzolar-<i>S</i>-methyl Chemical compound

Acibenzolar-S-methyl is the ISO common name for an organic compound that is used as a fungicide. Unusually, it is not directly toxic to fungi but works by inducing systemic acquired resistance, the natural defence system of plants.

<span class="mw-page-title-main">Azoxystrobin</span> Chemical compound

Azoxystrobin is a broad spectrum systemic fungicide widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status.

<span class="mw-page-title-main">Epoxiconazole</span> Fungicide

Epoxiconazole is a fungicide active ingredient from the class of azoles developed to protect crops. In particular, the substance inhibits the metabolism of fungi cells infesting useful plants, and thereby prevents the growth of the mycelia. Epoxiconazole also limits the production of conidia (mitospores). Epoxiconazole was introduced to the market by BASF SE in 1993 and can be found in many products and product mixtures targeting a large number of pathogens in various crops. Crops are, for example, cereals, soybeans, banana, rice, coffee, turnips, and red as well as sugar beets.

<span class="mw-page-title-main">Mepronil</span> Chemical compound

Mepronil is a fungicide used as a seed treatment or foliar spray in agriculture to protect crops from fungal diseases. It was first marketed by Kumiai Chemical Industries in 1981 using their brand name Basitac. The compound is a benzanilide which combines 2-methylbenzoic acid with the O-isopropyl derivative of 3-aminophenol to give an inhibitor of succinate dehydrogenase (SDHI).

<span class="mw-page-title-main">Cherry leaf spot</span> Plant fungal disease

Cherry leaf spot is a fungal disease which infects cherries and plums. Sweet, sour, and ornamental cherries are susceptible to the disease, being most prevalent in sour cherries. The variety of sour cherries that is the most susceptible are the English morello cherries. This is considered a serious disease in the Midwest, New England states, and Canada. It has also been estimated to infect 80 percent of orchards in the Eastern states. It must be controlled yearly to avoid a significant loss of the crop. If not controlled properly, the disease can dramatically reduce yields by nearly 100 percent. The disease is also known as yellow leaf or shothole disease to cherry growers due to the characteristic yellowing leaves and shot holes present in the leaves upon severe infection.

<span class="mw-page-title-main">Cyproconazole</span> Chemical compound

Cyproconazole is an agricultural fungicide of the class of azoles, used on cereal crops, coffee, sugar beet, fruit trees and grapes, and peanuts, on sod farms and golf course turf and on wood as a preservative. It has been used against powdery mildew, rust on cereals and apple scab, and applied by air or on the ground or by chemigation.

<span class="mw-page-title-main">Fludioxonil</span> Chemical compound

Fludioxonil is a synthetic phenylpyrrole chemical introduced by Ciba-Geigy in 1993 for use as a non-systemic fungicide. It is a structural analog of the natural fungicide pyrrolnitrin.

<span class="mw-page-title-main">Fluopyram</span> Chemical compound

Fluopyram is a fungicide and nematicide used in agriculture. It is used to control fungal diseases such as gray mold, powdery mildew, apple scab, Alternaria, Sclerotinia, and Monilinia. It is an inhibitor of succinate dehydrogenase.

<span class="mw-page-title-main">Oxycarboxin</span> Chemical compound

Oxycarboxin is an organic chemical used in agriculture to protect crops from fungal diseases. It was first marketed by Uniroyal in 1969 using their brand name Plantvax. The compound is an anilide which combines a heterocyclic acid with aniline to give an inhibitor of succinate dehydrogenase (SDHI).

<span class="mw-page-title-main">Sedaxane</span> Chemical compound

Sedaxane is a broad spectrum fungicide used as a seed treatment in agriculture to protect crops from fungal diseases. It was first marketed by Syngenta in 2011 using their brand name Vibrance. The compound is an amide which combines a pyrazole acid with an aryl amine to give an inhibitor of succinate dehydrogenase.

<span class="mw-page-title-main">Carboxin</span> Chemical compound used to kill fungi

Carboxin is a narrow-spectrum fungicide used as a seed treatment in agriculture to protect crops from fungal diseases. It was first marketed by Uniroyal in 1969 using their brand name Vitavax. The compound is an anilide which combines a heterocyclic acid with aniline to give an inhibitor of succinate dehydrogenase (SDHI).

<span class="mw-page-title-main">Agriculture in Maryland</span>

The US state of Maryland has large areas of fertile agricultural land in its coastal and Piedmont zones, though this land use is being encroached upon by urbanization. Agriculture is oriented to dairy farming for nearby large city milksheads, plus specialty perishable horticulture crops, such as cucumbers, watermelons, sweet corn, tomatoes, melons, squash, and peas.

<span class="mw-page-title-main">Boscalid</span> Chemical compound used to kill fungi

Boscalid is a broad spectrum fungicide used in agriculture to protect crops from fungal diseases. It was first marketed by BASF in 2002 using their brand name Endura. The compound is an biphenyl amide derived inhibitor of succinate dehydrogenase.

<span class="mw-page-title-main">Pydiflumetofen</span> Chemical compound used to kill fungi

Pydiflumetofen is a broad spectrum fungicide used in agriculture to protect crops from fungal diseases. It was first marketed by Syngenta in 2016 using their brand name Miravis. The compound is an amide which combines a pyrazole acid with a substituted phenethylamine to give an inhibitor of succinate dehydrogenase, an enzyme that inhibits cellular respiration in almost all living organisms.

3-(Difluoromethyl)-1-methyl-1<i>H</i>-pyrazole-4-carboxylic acid Chemical compound

3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid is a chemical compound which is used commercially as an intermediate to seven fungicides which act by inhibition of succinate dehydrogenase (SDHI). It consists of a pyrazole ring with difluoromethyl, methyl and carboxylic acid groups attached in specific positions.

References

  1. 1 2 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.
  2. 1 2 Strathmann, S.; Walker, S.; Barnes, J. (2011). "Fluxapyroxad: A new broad-spectrum fungicide". Phytopathology. 101 (6): 172. abstract
  3. 1 2 3 "Fluxapyroxad". New Active Ingredient Review. Minnesota Department of Agriculture. July 2012. Archived from the original on 25 June 2013.
  4. ↑ BASF, Crop Protection. "Xemium® for Seed Treatment" (PDF). BASF Crop Protection. Archived (PDF) from the original on 23 June 2018.
  5. 1 2 "SDHI Fungicides". Fungicide Resistance Action Committee. Archived from the original on 22 June 2013.
  6. ↑ 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. PMID   30722271. abstract
  7. ↑ 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. ISBN   9783527339471.
  8. 1 2 3 4 5 United States Environmental Protection Agency (26 February 2014). "Fluxapyroxad; Pesticide Tolerances". Federal Register.
  9. ↑ 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.
  10. ↑ BASF, Crop Protection. "Merivon Fungicide Product Sheet" (PDF). Archived (PDF) from the original on 25 October 2014.
  11. ↑ 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
  12. ↑ "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.
  13. ↑ 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
  14. ↑ 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. PMID   30722567. Abstract
  15. ↑ "Powdery Mildew on Peaches". Tree Fruit IPM Advisory. Utah State University. 6 May 2011. Archived from the original on 15 May 2011.
  16. ↑ 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.
  17. ↑ "Safety Data Sheet Priaxor (4.0)" (PDF). Crop Data Management Systems, Inc. 29 September 2014. Archived (PDF) from the original on 25 October 2014.
  18. ↑ "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.
  19. ↑ "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.
  20. ↑ "BASF's new fungicide fluxapyroxad got EU approval". Archived from the original on 24 July 2012.
  21. ↑ EPA Registration Number 7969-309
  22. ↑ EPA Registration Number 7969-306
  23. ↑ EPA Registration Number 7969-308
  24. ↑ BASF, Newsroom. "New Priaxor fungicide and Merivon fungicide now registered for use". BASF Crop Protection. Archived from the original on 23 June 2018.
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