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Fungicides
Fenpropimorph
Другие языки:

Fenpropimorph

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Fenpropimorph
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
ECHA InfoCard 100.060.636
PubChem CID
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
Boiling point 120 °C (248 °F; 393 K) (0.067 mbar)
4.3 mg/L (20 °C)
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. 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. 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.

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