Fenpropimorph

Fenpropimorph is a morpholine-derived fungicide used in agriculture, primarily on cereal crops such as wheat.[1] It has been reported to disrupt eukaryotic sterol biosynthesis pathways, notably by inhibiting fungal Δ14 reductases.[2] It has also been reported to inhibit mammalian sterol biosynthesis by affecting lanosterol demethylation.[2] Although used in agriculture for pest management purposes,[1] it has been reported to have a strong adverse effect on sterol biosynthesis in higher-plants by inhibiting the cycloeucalenol-obtusifoliol isomerase.[3] This inhibition was shown to not only alter the lipid composition of the plasma-membrane,[4] but also impact cell division and growth, in plants.[5]

Fenpropimorph
Names
IUPAC name
cis-2,6-Dimethyl-4-{2-methyl-3-[4-(2-methyl-2-propanyl)phenyl]propyl}morpholine or (2R,6S)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine
Other names
BAS 42100F; Corbel; Forbel 750; Mistral
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.060.636
UNII
  • InChI=1S/C20H33NO/c1-15(12-21-13-16(2)22-17(3)14-21)11-18-7-9-19(10-8-18)20(4,5)6/h7-10,15-17H,11-14H2,1-6H3/t15?,16-,17+
    Key: RYAUSSKQMZRMAI-ALOPSCKCSA-N
  • InChI=1/C20H33NO/c1-15(12-21-13-16(2)22-17(3)14-21)11-18-7-9-19(10-8-18)20(4,5)6/h7-10,15-17H,11-14H2,1-6H3/t15?,16-,17+
    Key: RYAUSSKQMZRMAI-ALOPSCKCBN
  • O2[C@H](CN(CC(C)Cc1ccc(cc1)C(C)(C)C)C[C@H]2C)C
Properties
C20H33NO
Molar mass 303.490 g·mol−1
Appearance Colorless liquid[1]
Boiling point 120 °C (248 °F; 393 K) (0.067 mbar)[1]
4.3 mg/L (20 °C)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

In addition to its effects on fungi, fenpropimorph is also a very high affinity ligand of the mammalian sigma receptor.[6]

References
  1. "Fenpropimorph" (PDF). Food and Agriculture Organization of the United Nations. Archived from the original (PDF) on 20 November 2004.
  2. Georgopapadakou NH, Walsh TJ (February 1996). "Antifungal agents: chemotherapeutic targets and immunologic strategies". Antimicrobial Agents and Chemotherapy. 40 (2): 279–91. doi:10.1128/AAC.40.2.279. PMC 163103. PMID 8834867.
  3. 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. doi:10.1016/0048-3575(86)90038-6.
  4. Hartmann MA, Perret AM, Carde JP, Cassagne C, Moreau P (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. 1583 (3): 285–96. doi:10.1016/S1388-1981(02)00249-4. PMID 12176396.
  5. He JX, Fujioka S, Li TC, Kang SG, Seto H, Takatsuto S, Yoshida S, Jang JC (March 2003). "Sterols regulate development and gene expression in Arabidopsis". Plant Physiology. 131 (3): 1258–69. doi:10.1104/pp.014605. PMC 166886. PMID 12644676.
  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. 18 (12): 4397–404. doi:10.1016/j.bmc.2010.04.078. PMC 3565575. PMID 20493718.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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