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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.

Fludioxonil
Names
Preferred IUPAC name
4-(2,2-Difluoro-2H-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile
Identifiers
  • 131341-86-1 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 77916
ECHA InfoCard 100.125.684
KEGG
  • C18462
  • 86398
UNII
  • ENS9J0YM16 Y
  • DTXSID2032398
  • 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).

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 is 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.

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 and Health hazards edit

It is toxic to fish and other aquatic organisms.[4] It has been detected as a residue in baby foods.[5]

See also edit

References edit

  1. ^
    • Hahn, Matthias (2014-05-28). "The rising threat of fungicide resistance in plant pathogenic fungi: Botrytis as a case study". Journal of Chemical Biology. 7 (4). Springer: 133–141. doi:10.1007/s12154-014-0113-1. ISSN 1864-6158. PMC 4182335. PMID 25320647.
    • Mari, Marta; Di francesco, Alessandra; Bertolini, Paolo (2014). "Control of fruit postharvest diseases: old issues and innovative approaches". Stewart Postharvest Review. 10 (1). Stewart Postharvest Solutions: 1–4. doi:10.2212/spr.2014.1.1. ISSN 1745-9656. S2CID 85221316.
    • Amiri, A.; Heath, S. M.; Peres, N. A. (2013). "Phenotypic Characterization of Multifungicide Resistance in Botrytis cinerea Isolates from Strawberry Fields in Florida". Plant Disease. 97 (3). American Phytopathological Society: 393–401. doi:10.1094/pdis-08-12-0748-re. ISSN 0191-2917. PMID 30722364. S2CID 73422752.
  2. ^ "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.
  5. ^ Evans, Sydney; Lacey, Anthony (November 15, 2023). "Pesticides still found in baby food, but biggest toxic threats eliminated". Environmental Working Group. Retrieved 25 November 2023.

fludioxonil, synthetic, phenylpyrrole, chemical, introduced, ciba, geigy, syngenta, 1993, systemic, fungicide, structural, analog, natural, fungicide, pyrrolnitrin, names, preferred, iupac, name, difluoro, benzodioxol, pyrrole, carbonitrile, identifiers, numbe. 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 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 16HKey MUJOIMFVNIBMKC UHFFFAOYSA NInChI 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 16HKey MUJOIMFVNIBMKC UHFFFAOYAI SMILES c1cc c2c c1 OC O2 F F c3c nH cc3C N Properties Chemical formula C 12H 6F 2N 2O 2 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 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 is 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 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 and Health hazards editIt is toxic to fish and other aquatic organisms 4 It has been detected as a residue in baby foods 5 See also edit1 3 BenzodioxoleReferences edit Hahn Matthias 2014 05 28 The rising threat of fungicide resistance in plant pathogenic fungi Botrytis as a case study Journal of Chemical Biology 7 4 Springer 133 141 doi 10 1007 s12154 014 0113 1 ISSN 1864 6158 PMC 4182335 PMID 25320647 Mari Marta Di francesco Alessandra Bertolini Paolo 2014 Control of fruit postharvest diseases old issues and innovative approaches Stewart Postharvest Review 10 1 Stewart Postharvest Solutions 1 4 doi 10 2212 spr 2014 1 1 ISSN 1745 9656 S2CID 85221316 Amiri A Heath S M Peres N A 2013 Phenotypic Characterization of Multifungicide Resistance in Botrytis cinerea Isolates from Strawberry Fields in Florida Plant Disease 97 3 American Phytopathological Society 393 401 doi 10 1094 pdis 08 12 0748 re ISSN 0191 2917 PMID 30722364 S2CID 73422752 Fludioxonil Ref CGA 173506 What s on your seed PDF Integrated Pest and Crop Management University of Wisconsin Madison Paranjape Kalyani Vasant Gowariker V N Krishnamurthy and Sugha Gowariker The Pesticide Encyclopedia CABI 2014 Evans Sydney Lacey Anthony November 15 2023 Pesticides still found in baby food but biggest toxic threats eliminated Environmental Working Group Retrieved 25 November 2023 Retrieved from https en wikipedia org w index php title Fludioxonil amp oldid 1188103714, wikipedia, wiki, book, books, library,

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