Fenpropimorph Explained

Fenpropimorph is a morpholine-derived fungicide used in agriculture, primarily on cereal crops such as wheat. It has been reported to disrupt eukaryotic sterol biosynthesis pathways, notably by inhibiting fungal Δ¹⁴ reductases. It has also been reported to inhibit mammalian sterol biosynthesis by affecting lanosterol demethylation.^[1] 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.^[2] This inhibition was shown to not only alter the lipid composition of the plasma-membrane,^[3] but also impact cell division and growth, in plants.^[4]

In addition to its effects on fungi, fenpropimorph is also a very high affinity ligand of the mammalian sigma receptor.^[5]

Notes and References

1. Georgopapadakou NH, Walsh TJ . Antifungal agents: chemotherapeutic targets and immunologic strategies . Antimicrobial Agents and Chemotherapy . 40 . 2 . 279–91 . February 1996 . 8834867 . 163103 . 10.1128/AAC.40.2.279 .
2. Rahier A, Schmitt P, Huss B, Benveniste P, Pommer EH . February 1986 . Chemical structure-activity relationships of the inhibition of sterol biosynthesis by N-substituted morpholines in higher plants . Pesticide Biochemistry and Physiology . 25 . 1 . 112–124 . 10.1016/0048-3575(86)90038-6 .
3. Hartmann MA, Perret AM, Carde JP, Cassagne C, Moreau P . 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 . 1583 . 3 . 285–96 . August 2002 . 12176396 . 10.1016/S1388-1981(02)00249-4 .
4. He JX, Fujioka S, Li TC, Kang SG, Seto H, Takatsuto S, Yoshida S, Jang JC . Sterols regulate development and gene expression in Arabidopsis . Plant Physiology . 131 . 3 . 1258–69 . March 2003 . 12644676 . 166886 . 10.1104/pp.014605 .
5. Hajipour AR, Fontanilla D, Chu UB, Arbabian M, Ruoho AE. 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 . 2010 . 18 . 12 . 4397–404 . 20493718 . 10.1016/j.bmc.2010.04.078 . 3565575 .