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Etridiazole

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Etridiazole
Names
Preferred IUPAC name 5-Ethoxy-3-(trichloromethyl)-1,2,4-thiadiazole
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.018.175 Edit this at Wikidata
EC Number
  • 219-991-8219-991-8
KEGG
MeSH C014547
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H5Cl3N2OS/c1-2-11-4-9-3(10-12-4)5(6,7)8/h2H2,1H3
SMILES
  • CCOC1=NC(=NS1)C(Cl)(Cl)Cl
Properties
Chemical formula C5H5Cl3N2OS
Molar mass 247.52 g·mol
Appearance Pure samples are colourless and odourless; impure samples take on a pale yellow appearance with a mild, persistent odour
Density 1.497 g cm
Melting point 22 °C (72 °F; 295 K)
Boiling point 95 °C (203 °F; 368 K) at 1 mmHg
Solubility in water 0.117 g dm
log P 3.37
Vapor pressure 0.011 mmHg/1.43 Pa at 25°C
Acidity (pKa) 2.27
Hazards
Flash point 154.5 °C (310.1 °F; 427.6 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1028 mg/kg (rat, oral)
2000 mg/kg (mouse, oral)
779 mg/kg (rabbit, oral)
1700 mg/kg (rabbit, dermal)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Etridiazole is a fungicide and pesticide used for prevention of pythium ultimum on cotton plants.

Synthesis

Etridiazole can be synthesised from acetonitrile as follows:

It can also be is produced by the reaction of trichloroacetamidine hydrochloride with trichloromethanesulfenyl chloride, and then with sodium hydroxide in ethanol.

Reactivity

Etridiazole is stable under normal conditions, but degrades upon continuous exposure to sunlight, and is hydrolysed by alkalis. When heated to decomposition, it emits toxic fumes of hydrogen chloride, sulfur oxides, and nitrogen oxides.

Safety

Etridiazole has been classified as a Group B2 Probable Human Carcinogen.

References

  1. MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Etridazole (2593-15-9) (2008-2010)
  2. "Applying a Fungicide May Prevent Cotton Replanting". Ag Alert. March 27, 2002.
  3. Muller F et al; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2012). NY, NY: John Wiley & Sons; Fungicides, Agricultural, 2. Individual Fungicides. Online Posting Date: October 15, 2011
  4. Worthing, C.R., S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 7th ed. Lavenham, Suffolk, Great Britain: The Lavenham Press Limited, 1983., p. 252
  5. Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 420
  6. Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 279
  7. Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1623
  8. USEPA Office of Pesticide Programs, Health Effects Division, Science Information Management Branch: "Chemicals Evaluated for Carcinogenic Potential" (April 2006)
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