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
CAS Number	67564-91-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:50145;
ChEMBL	ChEMBL372700;
ChemSpider	84290;
ECHA InfoCard	100.060.636
PubChem CID	93365;
UNII	4548UM725F ;
CompTox Dashboard (EPA)	DTXSID4034601 ;
	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

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]

References

"Fenpropimorph" (PDF). Food and Agriculture Organization of the United Nations. Archived from the original (PDF) on 20 November 2004.
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.
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.
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.
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.

External links

Fenpropimorph in the Pesticide Properties DataBase (PPDB)

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[FAO-1] "Fenpropimorph" (PDF). Food and Agriculture Organization of the United Nations. Archived from the original (PDF) on 20 November 2004.

[Georgopapadakou_1996-2] 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.

[pmid12176396-4] 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.