DFDT

DFDT
Names
Preferred IUPAC name
1,1′-(2,2,2-Trichloroethane-1,1-diyl)bis(4-fluorobenzene)
Other names
Fluorogesarol; Fluoro-DDT; p,p′-Fluoro-DDT; p,p′-Difluorodiphenyltrichloroethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.814 Edit this at Wikidata
EC Number
  • 207-493-3
UNII
  • InChI=1S/C14H9Cl3F2/c15-14(16,17)13(9-1-5-11(18)6-2-9)10-3-7-12(19)8-4-10/h1-8,13H
    Key: CLSXNIPAOWPLFR-UHFFFAOYSA-N
  • C1=CC(=CC=C1C(C2=CC=C(C=C2)F)C(Cl)(Cl)Cl)F
Properties
C14H9Cl3F2
Molar mass 321.57 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Difluorodiphenyltrichloroethane (DFDT) is a chemical compound. Its composition is the same as that of the insecticide DDT, except that two of DDT's chlorine atoms are replaced by two fluorine atoms.[1]

DFDT was developed as an insecticide by German scientists during World War II. It is possible that Hoechst wanted to avoid license fees for DDT to Schering or the original developer J. R. Geigy (the later Ciba-Geigy). It was documented by Allied military intelligence, but for Americans it remained in obscurity after the war.[1]

In 2019, New York University chemists reported that DFDT and a mono-fluorinated derivative, MFDT, might be a more effective insecticide than DDT, and might therefore be used to combat malaria with less of an environmental impact.[1][2] A later study of DFDT found it to be encumbered by the same resistance as DDT while being less effective in Drosophila melanogaster, and "unlikely to be a viable public health vector control insecticide".[3]

References

  1. ^ a b c Chang, Kenneth (17 October 2019). "A Nazi Version of DDT Was Forgotten. Could It Help Fight Malaria?". The New York Times. Retrieved 18 October 2019.
  2. ^ Zhu, Xiaolong; Hu, Chunhua T.; Yang, Jingxiang; Joyce, Leo A.; Qiu, Mengdi; Ward, Michael D.; Kahr, Bart (11 October 2019). "Manipulating Solid Forms of Contact Insecticides for Infectious Disease Prevention". Journal of the American Chemical Society. 141 (42): 16858–16864. doi:10.1021/jacs.9b08125. PMID 31601104. S2CID 204244148.
  3. ^ Norris, Edmund J.; Demares, Fabien; Zhu, Xiaolong; Bloomquist, Jeffrey R. (2020-11-01). "Mosquitocidal activity of p,p'-difluoro-diphenyl-trichloroethane (DFDT)". Pesticide Biochemistry and Physiology. 170: 104686. doi:10.1016/j.pestbp.2020.104686. ISSN 0048-3575. PMID 32980070. S2CID 222169601.
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