Chemistry:Fenpropimorph
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| 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
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| Other names
BAS 42100F; Corbel; Forbel 750; Mistral
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| 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). | |
| Infobox references | |
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
- ↑ 1.0 1.1 1.2 1.3 1.4 "Fenpropimorph". Food and Agriculture Organization of the United Nations. http://www.fao.org/ag/AGP/AGPP/Pesticid/JMPR/Download/95_eva/fenpro.pdf.
- ↑ 2.0 2.1 "Antifungal agents: chemotherapeutic targets and immunologic strategies". Antimicrobial Agents and Chemotherapy 40 (2): 279–91. February 1996. doi:10.1128/AAC.40.2.279. PMID 8834867.
- ↑ "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. February 1986. doi:10.1016/0048-3575(86)90038-6.
- ↑ "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. August 2002. doi:10.1016/S1388-1981(02)00249-4. PMID 12176396.
- ↑ "Sterols regulate development and gene expression in Arabidopsis". Plant Physiology 131 (3): 1258–69. March 2003. doi:10.1104/pp.014605. PMID 12644676.
- ↑ 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. PMID 20493718.
External links
- Fenpropimorph in the Pesticide Properties DataBase (PPDB)
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