Fluazinam

Fluazinam is a broad-spectrum fungicide used in agriculture. It is classed as a diarylamine and more specifically an arylaminopyridine. Its chemical name is 3-chloro-N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-2-pyridinamine. The mode of action involves the compound being an extremely potent uncoupler of oxidative phosphorylation in mitochondria and also having high reactivity with thiols. It is unique amongst uncouplers in displaying broad-spectrum activity against fungi and also very low toxicity to mammals due to it being rapidly metabolised to a compound without uncoupling activity. It was first described in 1992 and was developed by researchers at the Japanese company Ishihara Sangyo Kaisha.

Fluazinam
Names
Preferred IUPAC name
3-Chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)pyridin-2-amine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.114.073
UNII
  • InChI=1S/C13H4Cl2F6N4O4/c14-6-1-4(12(16,17)18)3-22-11(6)23-9-7(24(26)27)2-5(13(19,20)21)8(15)10(9)25(28)29/h1-3H,(H,22,23)
    Key: UZCGKGPEKUCDTF-UHFFFAOYSA-N
  • InChI=1/C13H4Cl2F6N4O4/c14-6-1-4(12(16,17)18)3-22-11(6)23-9-7(24(26)27)2-5(13(19,20)21)8(15)10(9)25(28)29/h1-3H,(H,22,23)
    Key: UZCGKGPEKUCDTF-UHFFFAOYAY
  • C1=C(C=NC(=C1Cl)NC2=C(C=C(C(=C2[N+](=O)[O-])Cl)C(F)(F)F)[N+](=O)[O-])C(F)(F)F
Properties
C13H4Cl2F6N4O4
Molar mass 465.09 g·mol−1
Density 1.8±0.1 g/cm3
Melting point 116 °C (241 °F; 389 K)
Boiling point 376.1±42.0°C (Predicted)
1.76 mg/L
Vapor pressure 5.51×10−8 mmHg (Predicted)
Hazards
Lethal dose or concentration (LD, LC):
5000mg/kg (rat, oral)
4190mg/kg (mallard, oral)
≥200μg (bee, contact)
≥1000mg/kg (worm, 28 day)
61ppb (rainbow trout, 96h)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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