Fluxapyroxad

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

Fluxapyroxad
File: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 Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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

[edit | edit source]

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

[edit | edit source]

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

[edit | edit source]

Fluxapyroxad 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
  • Pecan

Fungal diseases

[edit | edit source]

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

[edit | edit source]

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

[edit | edit source]

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]

References

[edit | edit source]
  1. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).abstract
  3. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  4. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  5. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  6. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). abstract
  7. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  8. ^ a b c d e Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  9. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  10. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  11. ^ Coating barley seed with fluxapyroxad increased germination due to reduced fungal activity. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). abstract
  12. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  13. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Abstract
  14. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Abstract
  15. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  16. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  17. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  18. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  19. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  20. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  21. ^ EPA Registration Number 7969-309
  22. ^ EPA Registration Number 7969-306
  23. ^ EPA Registration Number 7969-308
  24. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
Retrieved from "http://70.231.62.181/index.php?title=Fluxapyroxad&oldid=21813268"