Fludioxonil

Fludioxonil is a non-systemic fungicide, introduced in 1993 by Ciba-Geigy (now Syngenta). It is used for the treatment of crops, particularly cereals, fruits and vegetables, and ornamental plants. It is often used in combination with another fungicide such as Cyprodinil.

Fludioxonil
Names
Preferred IUPAC name
4-(2,2-Difluoro-2H-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.125.684
KEGG
UNII
  • InChI=1S/C12H6F2N2O2/c13-12(14)17-10-3-1-2-8(11(10)18-12)9-6-16-5-7(9)4-15/h1-3,5-6,16H
    Key: MUJOIMFVNIBMKC-UHFFFAOYSA-N
  • InChI=1/C12H6F2N2O2/c13-12(14)17-10-3-1-2-8(11(10)18-12)9-6-16-5-7(9)4-15/h1-3,5-6,16H
    Key: MUJOIMFVNIBMKC-UHFFFAOYAI
  • c1cc(c2c(c1)OC(O2)(F)F)c3c[nH]cc3C#N
Properties
C12H6F2N2O2
Molar mass 248.189 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

Its mode of action is to inhibit transport-associated phosphorylation of glucose, which reduces mycelial growth rate.[1] Fludioxonil is used against Fusarium, Rhizoctonia, Alternaria, Botrytis cinerea, and Stromatinia cepivora. There was a particularly bad crop failure due to multiresistant B. cinerea in strawberry in Florida in 2012; in that year and many other years, fludioxonil is the only a.i. still providing any protection.[2]

It is a structural analog of the natural fungicide pyrrolnitrin.

Nectarines treated with fludioxonil

Brand names include seed treatments: Celest, Agri Star Fludioxonil 41 ST, Dyna-shield Fludioxonil, Maxim 4 FS, and Spirato 480 FS, as well as foliar applications: Switch (fludioxonil + cyprodinil).[3]

Environmental hazards

It is toxic to fish and other aquatic organisms. [4]

See also

References
  1. "Fludioxonil (Ref: CGA 173506)".
  3. "What's on your seed?" (PDF). Integrated Pest and Crop Management, University of Wisconsin-Madison.
  4. Paranjape, Kalyani, Vasant Gowariker, V. N. Krishnamurthy, and Sugha Gowariker. The Pesticide Encyclopedia. CABI, 2014.
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