DFDT - Misplaced Pages

Chemical compound, insecticide

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
CAS Number	475-26-3
3D model (JSmol)	Interactive image
ChemSpider	9733
ECHA InfoCard	100.006.814
EC Number	207-493-3
PubChem CID	10139
UNII	5OLW69O0Q3
CompTox Dashboard (EPA)	DTXSID9042253
InChI InChI=1S/C14H9Cl3F2/c15-14(16,17)13(9-1-5-11(18)6-2-9)10-3-7-12(19)8-4-10/h1-8,13HKey: CLSXNIPAOWPLFR-UHFFFAOYSA-N
SMILES C1=CC(=CC=C1C(C2=CC=C(C=C2)F)C(Cl)(Cl)Cl)F
Properties
Chemical formula	C₁₄H₉Cl₃F₂
Molar mass	321.57 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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.

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.

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. 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".

References

^ 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.
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.
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.

v t e Pest control: Insecticides
Carbamates	Aldicarb Aminocarb Bendiocarb Butocarboxim Carbaryl Carbofuran Carbosulfan m-Cumenyl methylcarbamate Ethienocarb Fenobucarb Isoprocarb Methomyl Metolcarb Oxamyl Promecarb Propoxur
Inorganic compounds	Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Cryolite Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green
Insect growth regulators	Benzoylureas (Bistrifluron, Diflubenzuron, Flufenoxuron, Lufenuron, Noviflumuron) Hydroprene Methoprene Pyriproxyfen
Neonicotinoids	Acetamiprid Clothianidin Dinotefuran Imidacloprid Imidaclothiz Nitenpyram Nithiazine Paichongding Thiacloprid Thiamethoxam
Organochlorides	Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT DFDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene
Organophosphorus	Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Dimefox Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Mipafox Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos R-16661 Schradan Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon
Pyrethroids	Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Fluvalinate Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin
Diamides	Chlorantraniliprole Cyantraniliprole Flubendiamide
Other chemicals	Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner (+milbemycin oxime) Pyridaben Pyriprole Sarolaner Adjuvants (Piperonyl butoxide, Sesamex) Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone Ryanodine Ryanodol
Metabolites	Oxon Malaoxon Paraoxon TCPy
Biopesticides	Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Isaria fumosorosea Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paenibacillus popilliae Purpureocillium lilacinum Spinosad

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