Tebuthiuron

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Tebuthiuron[1][2][3][4][5]
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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
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3D model (JSmol)
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UN number 3077
  • 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)[who?]
2500 mg/L
Vapor pressure 0.27 mPa[6]
Hazards
Lethal dose or concentration (LD, LC):
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  • 644mg/kg (rat, oral)
  • 286mg/kg (rabbit, oral)
  • >500mg/kg (dogs, oral)[7]
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).

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Tebuthiuron is a nonselective broad spectrum herbicide of the urea class. 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][8] The ingredient was discovered by Air Products and Chemicals, but was registered by Elanco in the United States in 1974, and later sold to Dow AgroSciences.[9]

Environmental impacts

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 (soil half-life can exceed 360 days).

In Europe, tebuthiuron has been banned since November 2002.[10]

Application

Tebuthiuron is used agriculturally in Australia and the United States, usually formulated as granules, pellets or a wettable powder.[6] Pellets can be applied by hand (e.g. onto a clump of regrowth or along a fenceline), and by aircraft or ground equipment.[11] It can be applied any time of year, and once applied remains effective for several years. Tebuthiuron (as a 20% pellet) is applied at 0.5-2 g/m2,[12] equating to 0.1-0.4 g/m2 of active ingredient.

Tebuthiuron's herbicide resistance class is Group C, (Australia), C2 (global), Group 7, (numeric, i.e. Group 5, due to a merger).[13]

Vandalism

In 2010, tebuthiuron in the form of Dow AgroSciences Spike 80DF 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.[8][14] The lone perpetrator, a University of Alabama fan, was charged with first-degree criminal mischief and jailed on a $50,000 bond. Remediation involved removing about 1,780 tons of contaminated material.

In 2021, Arthur and Amelia Bond, wealthy summer residents of Camden, Maine poisoned their neighbor's oak trees with tebuthiuron to obtain a better view of Camden Harbor. They paid over $200,000 in fines to address illegal pesticide use and environmental contamination, and $1.5 million to settle with their neighbor.[15]

Tradenames

Tebuthiuron has been sold as "Tebuthiuron", "Brush", "Bullet", "Graslan", "Herbic", "Outlaw", "Perflan", "Reclaim", "Spike" and "Tebulex".[6][16]

References

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  1. ^ a b Page Module:Citation/CS1/styles.css has no content."Pesticide Information Profile Tebuthiuron". Cornell University. Sep 1993. Retrieved 17 February 2011.
  2. ^ Page Module:Citation/CS1/styles.css has no content."1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea". Royal Society of Chemistry. 2011. Retrieved 17 February 2011.
  3. ^ Page Module:Citation/CS1/styles.css has no content."Tebuthiuron". NIST. 2008. Retrieved 17 February 2011.
  4. ^ a b Page Module:Citation/CS1/styles.css has no content."Tebuthiuron Herbicide Fact Sheet" (PDF). Bonneville Power Administration. March 2000. Archived from the original (PDF) on 25 February 2013. Retrieved 17 February 2011.
  5. ^ Page Module:Citation/CS1/styles.css has no content."InfoCard". ECHA. Retrieved 17 October 2016.
  6. ^ a b c Page Module:Citation/CS1/styles.css has no content.Lewis, Kathleen A.; and Green, Andrew (18 May 2016). "An international database for pesticide risk assessments and management". Human and Ecological Risk Assessment. 22 (4): 1050–1064. doi:10.1080/10807039.2015.1133242. hdl:2299/17565.
  7. ^ Page Module:Citation/CS1/styles.css has no content."FMC Graslan Herbicide MSDS". ag.fmc.com. Australia. Jan 2022. Retrieved 1 June 2025.
  8. ^ a b Page Module:Citation/CS1/styles.css has no content.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.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Durkin, Patrick R. (September 22, 2016). "Tebuthiuron: Human Health and Ecological Risk Assessment FINAL REPORT" (PDF). USDA. Syracuse Environmental Research Associates, Inc. Retrieved 19 June 2024.
  10. ^ Page Module:Citation/CS1/styles.css has no content.European Commission (2002). "Commission Regulation (EC) No 2076/2002 of 20 November 2002". Retrieved 31 August 2016.
  11. ^ Page Module:Citation/CS1/styles.css has no content."Graslan Herbicide Label". ag.fmc.com/au/. FMC.
  12. ^ Page Module:Citation/CS1/styles.css has no content."Titan Tebuthiuron (Leaflet)" (PDF). Titan AG. Retrieved 1 June 2025.
  13. ^ Page Module:Citation/CS1/styles.css has no content."Classification of Herbicides According to Site of Action". Retrieved 19 July 2025.
  14. ^ Page Module:Citation/CS1/styles.css has no content."Man arrested in poisoning of Auburn University landmark live oaks". CNN. 17 February 2011. Retrieved 17 February 2011.
  15. ^ Page Module:Citation/CS1/styles.css has no content."Poisoned trees gave a wealthy couple a killer view — and united residents in outrage". NPR. June 19, 2024. Retrieved 19 June 2024.
  16. ^ Page Module:Citation/CS1/styles.css has no content."Tebulex 200GR Herbicide". Specialist Sales. 20 November 2024. Retrieved 1 June 2025.

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