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Terbuthylazine

Terbuthylazine
Skeletal formula of terbuthylazine
Space-filling model of the terbuthylazine molecule
Names
Preferred IUPAC name
N2-tert-Butyl-6-chloro-N4-ethyl-1,3,5-triazine-2,4-diamine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.025.125 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C9H16ClN5/c1-5-11-7-12-6(10)13-8(14-7)15-9(2,3)4/h5H2,1-4H3,(H2,11,12,13,14,15) checkY
    Key: FZXISNSWEXTPMF-UHFFFAOYSA-N checkY
  • InChI=1/C9H16ClN5/c1-5-11-7-12-6(10)13-8(14-7)15-9(2,3)4/h5H2,1-4H3,(H2,11,12,13,14,15)
    Key: FZXISNSWEXTPMF-UHFFFAOYAN
  • Clc1nc(nc(n1)NC(C)(C)C)NCC
Properties
C9H16ClN5
Molar mass 229.710 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 in place of the isopropyl and ethyl group, respectively.[1][2]The sim-azine molecule with 2 ethyl groups is symmetric and flat (excepting its equal ends). The threefold substituted triazines have resonance of the free (non-bonding, -) 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

[edit]
  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. Bibcode:1994Chmsp..28..467D. doi:10.1016/0045-6535(94)90291-7.
  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. Bibcode:2018JESHB..53..661C. doi:10.1080/03601234.2018.1474556. PMID 29842837. S2CID 44163175.
  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.