fenpropimorph

{{Chembox

| ImageFile = Fenpropimorph.svg

| ImageSize =

| IUPACName = 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

| OtherNames = BAS 42100F; Corbel; Forbel 750; Mistral

|Section1={{Chembox Identifiers

| CASNo = 67564-91-4

| CASNo_Ref = {{cascite|correct|}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4548UM725F

| PubChem = 93365

| ChemSpiderID = 84290

| ChEMBL = 372700

| ChEBI = 50145

| SMILES = O2[C@H](CN(CC(C)Cc1ccc(cc1)C(C)(C)C)C[C@H]2C)C

| 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+

| InChIKey = RYAUSSKQMZRMAI-ALOPSCKCBN

| StdInChI = 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+

| StdInChIKey = RYAUSSKQMZRMAI-ALOPSCKCSA-N

}}

|Section2={{Chembox Properties

| C=20 | H=33 | N=1 | O=1

| Appearance = Colorless liquid{{cite web | url = http://www.fao.org/ag/AGP/AGPP/Pesticid/JMPR/Download/95_eva/fenpro.pdf | archive-url = https://web.archive.org/web/20041120012346/http://www.fao.org/ag/AGP/AGPP/Pesticid/JMPR/Download/95_eva/fenpro.pdf | archive-date = 20 November 2004 | url-status = dead | title = Fenpropimorph | publisher = Food and Agriculture Organization of the United Nations }}

| Density =

| MeltingPt =

| BoilingPtC = 120

| BoilingPt_notes = (0.067 mbar)

| Solubility = 4.3 mg/L (20 °C)

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

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.{{cite journal | vauthors = Georgopapadakou NH, Walsh TJ | title = Antifungal agents: chemotherapeutic targets and immunologic strategies | journal = Antimicrobial Agents and Chemotherapy | volume = 40 | issue = 2 | pages = 279–91 | date = February 1996 | pmid = 8834867 | pmc = 163103 | doi = 10.1128/AAC.40.2.279 }} 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.{{Cite journal| vauthors = Rahier A, Schmitt P, Huss B, Benveniste P, Pommer EH |date= February 1986 |title=Chemical structure-activity relationships of the inhibition of sterol biosynthesis by N-substituted morpholines in higher plants |journal=Pesticide Biochemistry and Physiology |volume=25 |issue=1 |pages=112–124 |doi=10.1016/0048-3575(86)90038-6 }} This inhibition was shown to not only alter the lipid composition of the plasma-membrane,{{cite journal | vauthors = Hartmann MA, Perret AM, Carde JP, Cassagne C, Moreau P | title = Inhibition of the sterol pathway in leek seedlings impairs phosphatidylserine and glucosylceramide synthesis but triggers an accumulation of triacylglycerols | journal = Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids | volume = 1583 | issue = 3 | pages = 285–96 | date = August 2002 | pmid = 12176396 | doi = 10.1016/S1388-1981(02)00249-4 }} but also impact cell division and growth, in plants.{{cite journal | vauthors = He JX, Fujioka S, Li TC, Kang SG, Seto H, Takatsuto S, Yoshida S, Jang JC | title = Sterols regulate development and gene expression in Arabidopsis | journal = Plant Physiology | volume = 131 | issue = 3 | pages = 1258–69 | date = March 2003 | pmid = 12644676 | pmc = 166886 | doi = 10.1104/pp.014605 }}

In addition to its effects on fungi, fenpropimorph is also a very high affinity ligand of the mammalian sigma receptor.{{cite journal| author=Hajipour AR, Fontanilla D, Chu UB, Arbabian M, Ruoho AE| title=Synthesis and characterization of N,N-dialkyl and N-alkyl-N-aralkyl fenpropimorph-derived compounds as high affinity ligands for sigma receptors. | journal=Bioorg Med Chem | year= 2010 | volume= 18 | issue= 12 | pages= 4397–404 | pmid=20493718 | doi=10.1016/j.bmc.2010.04.078 | pmc=3565575 }}