Terbuthylazine

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.

Quick facts Names, Identifiers ...

Terbuthylazine

Names
Preferred IUPAC name N2-tert-Butyl-6-chloro-N4-ethyl-1,3,5-triazine-2,4-diamine
Identifiers
CAS Number	5915-41-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30263 Y
ChemSpider	20848 Y
ECHA InfoCard	100.025.125
KEGG	C18810 Y
PubChem CID	22206
UNII	M095B391J7 Y
CompTox Dashboard (EPA)	DTXSID4027608
InChI 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) Y Key: FZXISNSWEXTPMF-UHFFFAOYSA-N Y 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
SMILES Clc1nc(nc(n1)NC(C)(C)C)NCC
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

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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]