Tebuthiuron

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]

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
CAS Number	34014-18-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1557493
ChemSpider	5190
ECHA InfoCard	100.047.070
EC Number	251-793-7
KEGG	C18436
PubChem CID	5383
UNII	E5OX6GM11E
CompTox Dashboard (EPA)	DTXSID3024316
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
SMILES 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/cm^3
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
Main hazards	Xn (harmful), N (dangerous for the environment)
Safety data sheet	ChemAdvisor MSDS
R-phrases (outdated)	R22 R50, R53
S-phrases (outdated)	(S2), S37, S60, S61
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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. "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. "Tebuthiuron Herbicide Fact Sheet" (PDF). Bonneville Power Administration. March 2000. Retrieved 17 February 2011.
5. "InfoCard". ECHA. Retrieved 17 October 2016.
6. Dr. Stephen Enloe; Dr. 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