Fluopicolide

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Fluopicolide
Fluopicolide structure.svg
Names
Preferred IUPAC name
2,6-Dichloro-N-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methyl}benzamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.110.208 Edit this at Wikidata
UNII
  • InChI=1S/C14H8Cl3F3N2O/c15-8-2-1-3-9(16)12(8)13(23)22-6-11-10(17)4-7(5-21-11)14(18,19)20/h1-5H,6H2,(H,22,23)
    Key: GBOYJIHYACSLGN-UHFFFAOYSA-N
  • InChI=1/C14H8Cl3F3N2O/c15-8-2-1-3-9(16)12(8)13(23)22-6-11-10(17)4-7(5-21-11)14(18,19)20/h1-5H,6H2,(H,22,23)
    Key: GBOYJIHYACSLGN-UHFFFAOYAE
  • C1=CC(=C(C(=C1)Cl)C(=O)NCC2=C(C=C(C=N2)C(F)(F)F)Cl)Cl
Properties
C14H8Cl3F3N2O
Molar mass 383.58 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

Fluopicolide is a fungicide used in agriculture to control diseases caused by oomycetes such as late blight of potato. It is classed as an and its chemical name is 2,6-dichloro-N-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methyl}benzamide.[1] The precise mode of action is not known, but it is thought to act by affecting spectrin-like proteins in the cytoskeleton of oomycetes.[1][2] This mode of action differs from other available fungicides used to control oomycetes and it can inhibit the growth of strains that are resistant to phenylamides, strobilurin, dimethomorph and .[1] It has some systemic activity as it moves through the xylem towards the tips of stems, but does not get transported to the roots.[2] It affects the motility of zoospores, the germination of cysts, the growth of the mycelium and sporulation.[3] Bayer CropScience developed the compound and it was first released as a commercial product in 2006.[4]

Uses[]

Fluopicolide has been shown to be effective at controlling Phytophthora infestans, , , Plasmopara viticola, , Peronospora tabacina, Peronospora sparsa, Pseudoperonospora cubensis and Bremia lactucae. As of 2007, it was only available commercially as a co-formulation with Fosetyl-Al for use in vines (as Profiler) and as a co-formulation with propamocarb for use on potatoes and vegetables (as Infinito). Other products were in development.[5]

Toxicity[]

The median lethal dose in rats is >5000 mg/kg meaning that fluopicolide has low acute toxicity.[2][5] Tests in other mammals indicate that it does not cause , cancer or developmental problems.[5]

References[]

  1. ^ a b c Valérie Toquin, Marie-Pascal Latorse, and Roland Beffa (2012). Modern Crop Protection Compounds. John Wiley & Sons. pp. 831–838. ISBN 978-3-527-32965-6.CS1 maint: uses authors parameter (link)
  2. ^ a b c "Fluopicolide Toxicology" (PDF). Food and Agriculture Organization.
  3. ^ U. Gisi; Ilan Chet; Maria Lodovica Gullino (18 September 2009). Recent Developments in Management of Plant Diseases. Springer Science & Business Media. p. 19. ISBN 978-1-4020-8804-9.
  4. ^ "Bayer CropScience`s Infinito receives best combined rating". Biotech Week. 2007-06-20.
  5. ^ a b c Valérie Toquin; Francois Barja; Catherine Sirven; Roland Beffa (2007). "Fluopicolide, a new Anti-oomycetes Fungicide with a New Mode of Action inducing Perturbation of a Spectrin-like Protein". Modern Crop Protection Compounds. doi:10.1002/9783527619580.ch19.
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