Tebuthiuron

Tebuthiuron[1][2][3][4][5]
Names
Preferred IUPAC name
N-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-N,N′-dimethylurea
Other names
Spike; Brulan; Brush Bullet; EL-103; Graslan; Perflan; Herbec; Herbic; Reclaim
Identifiers
CAS Number
  • 34014-18-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:81745
ChEMBL
  • ChEMBL1557493
ChemSpider
  • 5190
ECHA InfoCard 100.047.070 Edit this at Wikidata
EC Number
  • 251-793-7
KEGG
  • C18436
PubChem CID
  • 5383
UNII
  • E5OX6GM11E checkY
UN number 3077
CompTox Dashboard (EPA)
  • DTXSID3024316 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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)
Solubility in water
 2500 mg/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 dangerous for the environment
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H410
P264, P270, P273, P301+P312, P330, P391, P501
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).
Infobox references
Chemical compound

Tebuthiuron is a nonselective broad spectrum herbicide of the urea class. 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][6]

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.[7]

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.[6][8]

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. ^ a b Stephen Enloe; Scott McElroy (15 February 2011). "The Poisoning of Toomer's Oaks" (PDF). Auburn University. Archived from the original (PDF) on 2011-02-20. Retrieved 17 February 2011.
  7. ^ European Commission (2002). "Commission Regulation (EC) No 2076/2002 of 20 November 2002". Retrieved 31 August 2016.
  8. ^ "Man arrested in poisoning of Auburn University landmark live oaks". CNN. 17 February 2011. Retrieved 17 February 2011.

External links

  • Dow AgroSciences MSDS on Spike 80DF
  • v
  • t
  • e
Anilides/anilinesAromatic acidsArsenicals
HPPD inhbitors
OrganophosphorusPhenoxy
Auxins
ACCase inhibitors
FOP herbicides
DIM herbicides
Protox inhibitors
Nitrophenyl ethers
Pyrimidinediones
Triazolinones
PyridinesQuaternary
Photosystem I inhibitors
Triazines
Photosystem II inhibitors
Ureas
Photosystem II inhibitors
ALS inhibitors
Others