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
CAS Number	67564-91-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:50145
ChEMBL	ChEMBL372700
ChemSpider	84290
ECHA InfoCard	100.060.636
PubChem CID	93365
UNII	4548UM725F Y
CompTox Dashboard (EPA)	DTXSID901045927 DTXSID4034601, DTXSID901045927
InChI 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
SMILES O2[C@H](CN(CC(C)Cc1ccc(cc1)C(C)(C)C)C[C@H]2C)C
Properties
Chemical formula	C20H33NO
Molar mass	303.490 g·mol−1
Appearance	Colorless liquid[1]
Boiling point	120 °C (248 °F; 393 K) (0.067 mbar)[1]
Solubility in water	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]

See also

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