Oxazolidinones: A New Class of Agricultural Fungicides

Sternberg, Jeffrey A.; Geffken, Detlef; Adams, John B.; Jordan, Douglas B.; Pöstages, Reiner; Sternberg, Charlene G.; Campbell, Carlton L.; Moberg, William K.; Livingston, Robert S.

doi:10.1021/bk-1998-0686.ch022

Cited by 16 publications

(13 citation statements)

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“…1 The fungicidal properties of this molecule were discovered through a chemical scouting and optimization methodology using enzyme and whole plant data rather than through an analog program against natural products or other known fungicides. 2 We report on studies which determined the mode of action of famoxadone and its oxazolidinone analogs (OADs) as a new chemical class of potent inhibitors of the catalytic function of mitochondrial cytochrome Based on the history of bc 1 . the discovery of famoxadone and OADs there is little surprise that the molecules do not resemble other known inhibitors of mitochondrial cytochrome bc 1 (Fig 1).3h10…”

Section: Introduction Famoxadonementioning

confidence: 99%

Mode of action of famoxadone

Jordan¹,

Livingston²,

Bisaha³

et al. 1999

Pestic. Sci.

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Famoxadone is a preventative and curative fungicide recently developed for plant disease control. The molecule and its oxazolidinone analogs (OADs) are potent inhibitors of mitochondrial electron transport, speciücally inhibiting the function of the enzyme ubiquinol :cytochrome c oxidoreductase (cytochrome Visible absorbance spectral studies on the puriüed enzyme suggested that bc 1 ). famoxadone bound close to the low potential heme of cytochrome b. This binding mode was conürmed in competitive binding experiments by studying the displacement of a radiolabelled OAD from submitochondria. EPR studies on the binding of famoxadone to submitochondria and puriüed suggested its binding mode was more like that of myxothiazol than that of stigmatellin (ligands bc 1 known to bind near the low potential heme). Zoospores of Phytophthora infestans, when given low concentrations of famoxadone and other OADs, were observed to cease oxygen consumption and motility within seconds and later the cells disintegrated, releasing the cellular contents. Famoxadone was a potent inhibitor of the growth of Saccharomyces cerevisiae when grown on non-fermentable carbon sources and it was an approximately 50-fold less potent inhibitor of growth when the yeast was grown on a fermentable carbon source, glucose. Such physiological observations are consistent with the loss of mitochondrial function imposed by famoxadone and OADs. Single amino acid changes in the apocytochrome b of baker's yeast cytochrome b located near the low potential heme altered the inhibition constants for the inhibitors famoxadone, myxothiazol, azoxystrobin and kresoxim-methyl diþ erentially, thus strongly suggesting diþ erent binding interactions of the protein with the inhibitors.

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Section: Introduction Famoxadonementioning

confidence: 99%

Mode of action of famoxadone

Jordan¹,

Livingston²,

Bisaha³

et al. 1999

Pestic. Sci.

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Section: Introductionmentioning

confidence: 99%

Mode of action of famoxadone

et al. 1999

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“…In analogy to amino acids, related α‐hydroxy acid derivatives are also valuable intermediates for the preparation of heterocyclic crop protection agents …”

Section: Different Possibilities For the Synthesis Of Heterocyclic Agmentioning

confidence: 99%

“…46,47 In analogy to amino acids, related α-hydroxy acid derivatives are also valuable intermediates for the preparation of heterocyclic crop protection agents. 48,49 Sometimes heterocyclic building blocks are employed as intermediates in the efficient synthesis of agrochemicals, although they are completely different from the heterocyclic scaffold of the active ingredient. The synthesis pathways to two insecticides wileyonlinelibrary.com/journal/ps demonstrate how conversion of one heterocycle into another as the key step enhances the efficiency of the synthesis.…”

Section: Different Possibilities For the Synthesis Of Heterocyclic Agmentioning

confidence: 99%

Heterocyclic chemistry in crop protection

2013

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An overview is given of the significance of heterocycles in crop protection chemistry, which is enormous as more than two-thirds of all agrochemicals launched to the market within the last 20 years belong to this huge group of chemicals. This review focuses on two important aspects of heterocyclic agrochemistry: the different roles of heterocyclic scaffolds in crop protection agents and the major possibilities for their synthesis.

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Oxazolidinones: A New Class of Agricultural Fungicides

Cited by 16 publications

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Mode of action of famoxadone

Mode of action of famoxadone

Mode of action of famoxadone

Heterocyclic chemistry in crop protection

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