Fluazinam

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 Edit this at Wikidata
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).

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.[1] The mode of action involves the compound being an extremely potent uncoupler of oxidative phosphorylation in mitochondria[2] and also having high reactivity with thiols.[1] 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.[1][3] It was first described in 1992 and was developed by researchers at the Japanese company Ishihara Sangyo Kaisha.[4]

  1. ^ a b c Ulrich Schirmer; Peter Jeschke; Matthias Witschel (2012). Modern Crop Protection Compounds: Herbicides. John Wiley & Sons. pp. 662–663. ISBN 978-3-527-32965-6.
  2. ^ Ze-jian Guo; Hideto Miyoshi; Terumasa Komyoji; Takahiro Haga; Toshio Fujita (1991). "Uncoupling activity of a newly developed fungicide, fluazinam [3-chloro-N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-2-pyridinamine]". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 1056 (1): 89–92. doi:10.1016/S0005-2728(05)80077-5.
  3. ^ Society for General Microbiology. Symposium (4 May 1995). Fifty Years of Antimicrobials: Past Perspectives and Future Trends. Cambridge University Press. pp. 104–105. ISBN 978-0-521-48108-3.
  4. ^ Robert Krieger (17 October 2001). Handbook of Pesticide Toxicology, Two-Volume Set: Principles and Agents. Academic Press. p. 1243. ISBN 978-0-08-053379-7.