Fludioxonil

Fludioxonil is a synthetic phenylpyrrole chemical introduced by Ciba-Geigy (now Syngenta) in 1993 for use as a non-systemic fungicide. It is a structural analog of the natural fungicide pyrrolnitrin.

Quick facts Names, Identifiers ...

Fludioxonil

Names
Preferred IUPAC name 4-(2,2-Difluoro-2H-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile
Identifiers
CAS Number	131341-86-1 Y
3D model (JSmol)	Interactive image
ChemSpider	77916
ECHA InfoCard	100.125.684
KEGG	C18462
PubChem CID	86398
UNII	ENS9J0YM16 Y
CompTox Dashboard (EPA)	DTXSID2032398
InChI 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
SMILES c1cc(c2c(c1)OC(O2)(F)F)c3c[nH]cc3C#N
Properties
Chemical formula	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

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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. 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 was the only fungicide still providing any protection.^[1]

Its mode of action is to inhibit transport-associated phosphorylation of glucose, which reduces mycelial growth rate.^[2] Fludioxonil is used against Fusarium, Rhizoctonia, Alternaria, Botrytis cinerea, and Stromatinia cepivora.

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]