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| Names | |
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| Preferred IUPAC name
N2-tert-Butyl-6-chloro-N4-ethyl-1,3,5-triazine-2,4-diamine | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.025.125 👁 Edit this at Wikidata |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C9H16ClN5 | |
| Molar mass | 229.710 g/mol |
| Density | 1.19 g/cm3 |
| Melting point | 176 to 179 °C (349 to 354 °F; 449 to 452 K) |
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 −[C−(CH3)3] in place of the isopropyl −[CH−(CH3)2] and ethyl group, respectively.[1][2] The sim-azine molecule with 2 ethyl groups is symmetric and flat (excepting its equal NH−C2H5 ends). The threefold substituted triazines have resonance of the free (non-bonding, 👁 {\textstyle \pi }
-) 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.
Terbuthylazine's HRAC classification is Group C1, Group C (global, Aus), Group 5 (numeric), as it inhibits photosynthesis at photosystem II.[4]
References
[edit]- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Classification of Herbicides According to Site of Action". Retrieved 19 July 2025.