Structure via PubChem · Public domain (PubChem)
terbuthylazine
Sign in to saveAlso known as Terbutylazine, Terbutylethylazine
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.
In the Vinony graph
Within Vinony's link graph, terbuthylazine is referenced by 161 other articles, and connects out to phenoxy herbicide, photosynthesis and arsenic.
It sits within the topics Chloroarenes, ECHA InfoCard ID from Wikidata and Group 5 herbicides.
Its subject is documented across 11 Wikipedia language editions.
Chemical data
- Formula
- C9H16ClN5
- Molecular weight
- 229.71 g/mol
- IUPAC name
- 2-N-tert-butyl-6-chloro-4-N-ethyl-1,3,5-triazine-2,4-diamine
- SMILES
- CCNC1=NC(=NC(=N1)Cl)NC(C)(C)C
- InChIKey
- FZXISNSWEXTPMF-UHFFFAOYSA-N
- XLogP
- 3.1
- Polar surface area
- 62.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
558 papers- Terbuthylazine and desethylterbuthylazine: Recent occurrence, mobility and removal techniques.Chemosphere · 2018
- Terbuthylazine herbicide: an alternative to atrazine for weed control in glyphosate-tolerant maize.Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes · 2022
- Bioaccumulation and toxicity of terbuthylazine in earthworms (Eisenia fetida).Environmental toxicology and pharmacology · 2023
- Terbuthylazine exposure induces innate immune response and inflammation through activating cGAS-STING/NF-κB pathway in myocardium of broiler chicken (Gallus gallus).Pesticide biochemistry and physiology · 2023
- Biodegradation characteristics and mechanism of terbuthylazine by the newly isolated Agrobacterium rhizogenes strain AT13.Journal of hazardous materials · 2023
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Mass
- 229.109
- Has use
- pesticide
Show 4 more facts
- chemical formula
- C₉H₁₆ClN₅
- canonical SMILES
- CCNC1=NC(=NC(=N1)Cl)NC(C)(C)C
- isomeric SMILES
- CC/N=C/1\NC(=NC(=N1)Cl)NC(C)(C)C
- Commons category
- Terbuthylazine
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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.
Excerpted from Wikipedia’s “terbuthylazine” article, available under the CC BY-SA 4.0 licence.