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Fenpropimorph

Fenpropimorph is a morpholine-derived fungicide used in agriculture, primarily on cereal crops such as wheat. Although used in agriculture for pest management purposes, it has been reported to have a strong adverse effect on sterol biosynthesis in higher-plants by inhibiting the cycloeucalenol-obtusifoliol isomerase. This inhibition was shown to not only alter the lipid composition of the plasma-membrane, but also impact cell division and growth, in plants.

In addition to its effects on fungi, fenpropimorph is also a very high affinity ligand of the mammalian sigma receptor.

References

References

  1. "Fenpropimorph". Food and Agriculture Organization of the United Nations.
  2. (February 1996). "Antifungal agents: chemotherapeutic targets and immunologic strategies". Antimicrobial Agents and Chemotherapy.
  3. (February 1986). "Chemical structure-activity relationships of the inhibition of sterol biosynthesis by N-substituted morpholines in higher plants". Pesticide Biochemistry and Physiology.
  4. (August 2002). "Inhibition of the sterol pathway in leek seedlings impairs phosphatidylserine and glucosylceramide synthesis but triggers an accumulation of triacylglycerols". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids.
  5. (March 2003). "Sterols regulate development and gene expression in Arabidopsis". Plant Physiology.
  6. Hajipour AR, Fontanilla D, Chu UB, Arbabian M, Ruoho AE. (2010). "Synthesis and characterization of N,N-dialkyl and N-alkyl-N-aralkyl fenpropimorph-derived compounds as high affinity ligands for sigma receptors.". Bioorg Med Chem.
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fungicides morpholines tert-butyl-compounds para-phenylene-compounds
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