Etridiazole

Etridiazole
Names
Preferred IUPAC name
5-Ethoxy-3-(trichloromethyl)-1,2,4-thiadiazole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.018.175 Edit this at Wikidata
EC Number
  • 219-991-8219-991-8
KEGG
MeSH C014547
UNII
  • InChI=1S/C5H5Cl3N2OS/c1-2-11-4-9-3(10-12-4)5(6,7)8/h2H2,1H3
  • CCOC1=NC(=NS1)C(Cl)(Cl)Cl
Properties
C5H5Cl3N2OS
Molar mass 247.52 g·mol−1
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−3 [1]
Melting point 22 °C (72 °F; 295 K)
Boiling point 95 °C (203 °F; 368 K) at 1 mmHg
0.117 g dm−3
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):
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 [77 °F], 100 kPa).

Etridiazole is a fungicide and pesticide used for prevention of pythium ultimum on cotton plants.[2]

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.[3]

Reactivity

Etridiazole is stable under normal conditions,[4] but degrades upon continuous exposure to sunlight,[5] and is hydrolysed by alkalis.[6] When heated to decomposition, it emits toxic fumes of hydrogen chloride, sulfur oxides, and nitrogen oxides.[7]

Safety

Etridiazole has been classified as a Group B2 Probable Human Carcinogen.[8]

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)