fludioxonil

{{Chembox

| ImageFile = fludioxonil.svg

| ImageSize = 200px

| ImageFile2 = Fludioxonil 3D BS.png

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| PIN = 4-(2,2-Difluoro-2H-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile

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| Section1 = {{Chembox Identifiers

| CASNo = 131341-86-1

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = ENS9J0YM16

| PubChem = 86398

| ChemSpiderID = 77916

| KEGG = C18462

| SMILES = c1cc(c2c(c1)OC(O2)(F)F)c3c[nH]cc3C#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

| InChIKey = MUJOIMFVNIBMKC-UHFFFAOYAI

| StdInChI = 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

| StdInChIKey = MUJOIMFVNIBMKC-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=12|H=6|F=2|N=2|O=2

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| Section3 = {{Chembox Hazards

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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.

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.

{{Unbulleted list citebundle

|{{cite journal | last=Hahn | first=Matthias | title=The rising threat of fungicide resistance in plant pathogenic fungi: Botrytis as a case study | journal=Journal of Chemical Biology | publisher=Springer | volume=7 | issue=4 | date=2014-05-28 | issn=1864-6158 | doi=10.1007/s12154-014-0113-1 | pages=133–141| pmid=25320647 | pmc=4182335 }}

|{{cite journal | title=Control of fruit postharvest diseases: old issues and innovative approaches | journal=Stewart Postharvest Review | publisher=Stewart Postharvest Solutions | volume=10 | issue=1 | year=2014 | issn=1745-9656 | doi=10.2212/spr.2014.1.1 | pages=1–4 | s2cid=85221316 | url=http://www.ingentaconnect.com/content/sphs/sphr/2014/00000010/00000001/art00001 | first1=Marta | last1=Mari | first2=Alessandra | last2=Di francesco | first3=Paolo | last3=Bertolini}}

|{{cite journal | last1=Amiri | first1=A. | last2=Heath | first2=S. M. | last3=Peres | first3=N. A. | title=Phenotypic Characterization of Multifungicide Resistance in Botrytis cinerea Isolates from Strawberry Fields in Florida | journal=Plant Disease | publisher=American Phytopathological Society | volume=97 | issue=3 | year=2013 | issn=0191-2917 | doi=10.1094/pdis-08-12-0748-re | pages=393–401 | s2cid=73422752 | pmid=30722364| doi-access= }}

}}

Its mode of action is to inhibit transport-associated phosphorylation of glucose, which reduces mycelial growth rate.{{Cite web|url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/330.htm|title = Fludioxonil (Ref: CGA 173506)}} Fludioxonil is used against Fusarium, Rhizoctonia, Alternaria, Botrytis cinerea, and Stromatinia cepivora.

File:Nectarines treated with fludioxonil.jpg

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).{{cite web | url = https://ipcm.wisc.edu/download/pubsPM/Whats_on_your_seed_web.pdf | title = What's on your seed? | publisher = Integrated Pest and Crop Management, University of Wisconsin-Madison}}