Fenpropimorph

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 Edit this at Wikidata
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).

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]

References

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  1. ^ a b c d e "Fenpropimorph" (PDF). Food and Agriculture Organization of the United Nations. Archived from the original (PDF) on 20 November 2004.
  2. ^ a b 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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