Terbuthylazine

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title: "Terbuthylazine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["herbicides", "triazines", "chloroarenes", "tert-butyl-compounds", "group-5-herbicides"] topic_path: "general/herbicides" source: "https://en.wikipedia.org/wiki/Terbuthylazine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| verifiedrevid = 470602280 | ImageFile = Terbuthylazine.svg | ImageAlt = Skeletal formula of terbuthylazine | ImageFile1 = Terbuthylazine-3D-spacefill.png | ImageAlt1 = Space-filling model of the terbuthylazine molecule | PIN=N2-tert-Butyl-6-chloro-N4-ethyl-1,3,5-triazine-2,4-diamine | OtherNames= |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 20848 | 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) | InChIKey = FZXISNSWEXTPMF-UHFFFAOYAN | StdInChI_Ref = | StdInChI = 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) | StdInChIKey_Ref = | StdInChIKey = FZXISNSWEXTPMF-UHFFFAOYSA-N | CASNo_Ref = | CASNo=5915-41-3 | UNII_Ref = | UNII = M095B391J7 | PubChem=22206 | KEGG_Ref = | KEGG = C18810 | ChEBI_Ref = | ChEBI = 30263 | SMILES = Clc1nc(nc(n1)NC(C)(C)C)NCC |Section2={{Chembox Properties | Formula=C9H16ClN5 | MolarMass=229.710 g/mol | Appearance= | Density= 1.19 g/cm3 | MeltingPtC= 176 to 179 | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = 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. 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, \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) 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.

References

References

  1. (1994). "Sorption of terbuthylazine and atrazine in relation to the physico-chemical properties of three soils". [[Chemosphere (journal).
  2. (2018). "Dissipation of terbuthylazine, metolachlor, and mesotrione in soils with contrasting texture". [[J Environ Sci Health B]].
  3. Atrazine: Chemical Summary. Toxicity and Exposure Assessment for Children's Health (PDF) (Report). U.S. [[United States Environmental Protection Agency. Environmental Protection Agency]]. 2007-04-24. Archived from the original (PDF) on 2012-03-16.
  4. "Classification of Herbicides According to Site of Action".

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herbicidestriazineschloroarenestert-butyl-compoundsgroup-5-herbicides