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Fludioxonil
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Fludioxonil

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Fludioxonil
Fludioxonil.svg
Fludioxonil 3D BS.png
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
PubChem CID
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).

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.

Its mode of action is to inhibit transport-associated phosphorylation of glucose, which reduces mycelial growth rate. 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.

It is a structural analog of the natural fungicide pyrrolnitrin.

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).

Environmental hazards

It is toxic to fish and other aquatic organisms.

See also


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