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Tebuthiuron

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Tebuthiuron[1][2][3][4][5]
Names
IUPAC name
1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea
Other names
Spike; Brulan; Brush Bullet; EL-103; Graslan; Perflan; Herbec; Herbic; Reclaim
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.047.070 Edit this at Wikidata
EC Number
  • 251-793-7
KEGG
  • InChI=1S/C9H16N4OS/c1-9(2,3)6-11-12-8(15-6)13(5)7(14)10-4/h1-5H3,(H,10,14)
    Key: HBPDKDSFLXWOAE-UHFFFAOYSA-N
  • InChI=1/C9H16N4OS/c1-9(2,3)6-11-12-8(15-6)13(5)7(14)10-4/h1-5H3,(H,10,14)
    Key: HBPDKDSFLXWOAE-UHFFFAOYAB
  • O=C(N(c1nnc(s1)C(C)(C)C)C)NC
Properties
C9H16N4OS
Molar mass 228.31 g·mol−1
Appearance Off-white to buff colored crystalline solid
Density 1.186 g/cm3
Melting point 163.19 °C (325.74 °F; 436.34 K) (mean or weighted MP)
Boiling point 394.23 °C (741.61 °F; 667.38 K) (Adapted Stein & Brown method)
2500 mg/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Xn (harmful), N (dangerous for the environment)
Safety data sheet (SDS) ChemAdvisor MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tebuthiuron is a nonselective broad spectrum herbicide of the urea class.[6] It is used in a number of herbicides manufactured by Dow AgroSciences, and is sold under several trade names, depending on the formulation. It is used to control weeds, woody and herbaceous plants, and sugar cane.[1] It is absorbed by the roots and transported to the leaves, where it inhibits photosynthesis.[4][7]

The Environmental Protection Agency considers tebuthiuron to have a great potential for groundwater contamination, due to its high water solubility, low adsorption to soil particles, and high persistence in soil (its soil half-life is 360 days).

In Europe, Tebuthiuron has been banned since November 2002.[8]

In 2010, tebuthiuron was deliberately used in an act of vandalism to poison the live oak trees at Toomer's Corner on the Auburn University campus, following the 2010 Iron Bowl.[7][9]

References

  1. ^ a b "Pesticide Information Profile Tebuthiuron". Cornell University. Sep 1993. Retrieved 17 February 2011.
  2. ^ "1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea". Royal Society of Chemistry. 2011. Retrieved 17 February 2011.
  3. ^ "Tebuthiuron". NIST. 2008. Retrieved 17 February 2011.
  4. ^ a b "Tebuthiuron Herbicide Fact Sheet" (PDF). Bonneville Power Administration. March 2000. Retrieved 17 February 2011.
  5. ^ "InfoCard". ECHA. Retrieved 17 October 2016.
  6. ^ Alan Wood (2010). "Herbicides". Retrieved 17 February 2011.
  7. ^ a b Dr. Stephen Enloe; Dr. Scott McElroy (15 February 2011). "The Poisoning of Toomer's Oaks" (PDF). Auburn University. Retrieved 17 February 2011.
  8. ^ European Commission (2002). "Commission Regulation (EC) No 2076/2002 of 20 November 2002". Retrieved 31 August 2016.
  9. ^ "Man arrested in poisoning of Auburn University landmark live oaks". CNN. 17 February 2011. Retrieved 17 February 2011.
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