Chemistry:Terbuthylazine

From HandWiki

Terbuthylazine is a selective herbicide. Chemically, it is a halogenated triazine; compared with atrazine (1958 inv., Geigy lab) and simazine, it has a tert-butyl group –[C–(CH
3
)
3
]
in place of the isopropyl –[CH–(CH
3
)
2
]
and ethyl group, respectively.[1][2] The sim-azine molecule with 2 ethyl groups is symmetric and flat (excepting its equal NH–C
2
H
5
ends). The threefold substituted triazines have resonance of the free (non-bonding, π-) electron pairs, resulting in equivalent mesomeric structures.

Simazine remains active in the soil for 2 to 7 months or longer after application. Atrazine remains in soil for a matter of months (although in some soils can persist to at least 4 years)[3] and can migrate from soil to groundwater.


References

  1. Dousset, S.; Mouvet, C.; Schiavon, M. (1994). "Sorption of terbuthylazine and atrazine in relation to the physico-chemical properties of three soils". Chemosphere 28 (3): 467–476. doi:10.1016/0045-6535(94)90291-7. Bibcode1994Chmsp..28..467D. 
  2. Carretta, L.; Cardinali, A.; Marotta, E.; Zanin, G.; Masin, R. (2018). "Dissipation of terbuthylazine, metolachlor, and mesotrione in soils with contrasting texture". J Environ Sci Health B 53 (10): 661–668. doi:10.1080/03601234.2018.1474556. PMID 29842837. Bibcode2018JESHB..53..661C. 
  3. Atrazine: Chemical Summary. Toxicity and Exposure Assessment for Children's Health (PDF) (Report). U.S. Environmental Protection Agency. 2007-04-24. Archived from the original (PDF) on 2012-03-16.