Fenpropimorph

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Fenpropimorph
File:Fenpropimorph.svg
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
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UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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).

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]

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

See also

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  • Amorolfine - same core structure but with a tert-amyl group in place of the tert-butyl

References

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