Fluopicolide

Last updated
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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).

Fluopicolide is a fungicide used in agriculture to control diseases caused by oomycetes such as late blight of potato. It is classed as an acylpicolide 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 iprovalicarb. [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]

Contents

Uses

Fluopicolide has been shown to be effective at controlling Phytophthora infestans , Phytophthora capsicii , Phytophthora porri , Plasmopara viticola , Perenospora parasitica , 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 skin sensitisation, cancer or developmental problems. [5]

References

  1. 1 2 3 Valérie Toquin; Marie-Pascal Latorse; Roland Beffa (2012). Modern Crop Protection Compounds. John Wiley & Sons. pp. 831–838. ISBN   978-3-527-32965-6.
  2. 1 2 3 "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. 1 2 3 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. pp. 675–682. doi:10.1002/9783527619580.ch19. ISBN   9783527619580.
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