Flusilazole

Last updated
Flusilazole
Flusilazol1.svg
Flusilazole-3D-balls.png
Names
Preferred IUPAC name
1-{[Bis(4-fluorophenyl)(methyl)silyl]methyl}-1H-1,2,4-triazole
Other names
DPX-H6573;
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.107.525 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C16H15F2N3Si/c1-22(12-21-11-19-10-20-21,15-6-2-13(17)3-7-15)16-8-4-14(18)5-9-16/h2-11H,12H2,1H3 X mark.svgN
    Key: FQKUGOMFVDPBIZ-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H15F2N3Si/c1-22(12-21-11-19-10-20-21,15-6-2-13(17)3-7-15)16-8-4-14(18)5-9-16/h2-11H,12H2,1H3
    Key: FQKUGOMFVDPBIZ-UHFFFAOYAI
  • c2ncnn2C[Si](C)(c(cc1)ccc1F)c3ccc(F)cc3
Properties
C16H15F2N3Si
Molar mass 315.392 g/mol
Density 1.31 g/cm3
Melting point 53–55 °C (127–131 °F; 326–328 K)
41.9 mg/L (20 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Flusilazole (DPX-H6573) is an organosilicon fungicide invented by DuPont, which is used to control fungal infections on a variety of fruit and vegetable crops. [1] [2] [3] It is moderately toxic to animals and has been shown to produce birth defects in high doses. [4] [5]

References

  1. Moberg, W. K.; Basarab, G. S.; Cuomo, J.; Liang, P. H. (1987). "Biologically Active Organosilicon Compounds". Synthesis and Chemistry of Agrochemicals. ACS Symposium Series. Vol. 355. pp. 288–301. doi:10.1021/bk-1987-0355.ch026. ISBN   9780841214347.
  2. Bostanian NJ, Larocque N, Chouinard G, Coderre D (November 2001). "Baseline toxicity of several pesticides to Hyaliodes vitripennis (Say) (Hemiptera: Miridae)". Pest Management Science. 57 (11): 1007–10. doi:10.1002/ps.374. PMID   11721516.
  3. Eckert MR, Rossall S, Selley A, Fitt BD (April 2010). "Effects of fungicides on in vitro spore germination and mycelial growth of the phytopathogens Leptosphaeria maculans and L. biglobosa (phoma stem canker of oilseed rape)". Pest Management Science. 66 (4): 396–405. doi: 10.1002/ps.1890 . PMID   20013877.
  4. Farag AT, Ibrahim HH (February 2007). "Developmental toxic effects of antifungal flusilazole administered by gavage to mice". Birth Defects Research Part B: Developmental and Reproductive Toxicology. 80 (1): 12–7. doi:10.1002/bdrb.20098. PMID   17187383.
  5. Hermsen SA, van den Brandhof EJ, van der Ven LT, Piersma AH (January 2011). "Relative embryotoxicity of two classes of chemicals in a modified zebrafish embryotoxicity test and comparison with their in vivo potencies". Toxicology in Vitro . 25 (3): 745–753. doi: 10.1016/j.tiv.2011.01.005 . PMID   21238576.