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'''Terbuthylazine''' is a selective ]. Chemically, it is a halogenated ]; compared with ] and ], it has a ] group in place of the ] and ] groups, respectively.<ref>{{cite journal|title=Sorption of terbuthylazine and atrazine in relation to the physico-chemical properties of three soils|journal=]|volume=28|issue=3|pages=467–476|doi=10.1016/0045-6535(94)90291-7|year=1994|last1=Dousset|first1=S.|last2=Mouvet|first2=C.|last3=Schiavon|first3=M.|bibcode=1994Chmsp..28..467D }}</ref><ref>{{cite journal|title=Dissipation of terbuthylazine, metolachlor, and mesotrione in soils with contrasting texture|journal=]|volume=53|issue=10|pages=661–668|doi=10.1080/03601234.2018.1474556|year=2018|last1=Carretta|first1=L.|last2=Cardinali|first2=A.|last3=Marotta|first3=E.|last4=Zanin|first4=G.|last5=Masin|first5=R.|pmid=29842837|bibcode=2018JESHB..53..661C |s2cid=44163175 }}</ref> '''Terbuthylazine''' is a selective ]. Chemically, it is a halogenated ]; compared with ] (1958 inv., ] lab) and ], it has a ] group <chem display="inline">-</chem> in place of the ] <chem display="inline">-</chem> and ] group, respectively.<ref>{{cite journal|title=Sorption of terbuthylazine and atrazine in relation to the physico-chemical properties of three soils|journal=]|volume=28|issue=3|pages=467–476|doi=10.1016/0045-6535(94)90291-7|year=1994|last1=Dousset|first1=S.|last2=Mouvet|first2=C.|last3=Schiavon|first3=M.|bibcode=1994Chmsp..28..467D }}</ref><ref>{{cite journal|title=Dissipation of terbuthylazine, metolachlor, and mesotrione in soils with contrasting texture|journal=]|volume=53|issue=10|pages=661–668|doi=10.1080/03601234.2018.1474556|year=2018|last1=Carretta|first1=L.|last2=Cardinali|first2=A.|last3=Marotta|first3=E.|last4=Zanin|first4=G.|last5=Masin|first5=R.|pmid=29842837|bibcode=2018JESHB..53..661C |s2cid=44163175 }}</ref>The sim-azine molecule with 2 ethyl groups is symmetric and flat (excepting its equal <chem display="inline">NH-C2H5</chem>ends). The threefold substituted triazines have ] of the free (non-bonding, <math display="inline">\pi</math>-) electron pairs, resulting in equivalent ] 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)<ref>Atrazine: Chemical Summary. Toxicity and Exposure Assessment for Children's Health (PDF) (Report). U.S. ]. 2007-04-24. Archived from the original (PDF) on 2012-03-16.</ref> and can migrate from soil to ].>
==Referenced==

==References==
{{reflist}} {{reflist}}
{{Herbicides}} {{Herbicides}}

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Terbuthylazine
Skeletal formula of terbuthylazine
Space-filling model of the terbuthylazine molecule
Names
Preferred IUPAC name N-tert-Butyl-6-chloro-N-ethyl-1,3,5-triazine-2,4-diamine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.025.125 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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)Key: FZXISNSWEXTPMF-UHFFFAOYSA-N
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

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 ( CH 3 ) 3 ] {\textstyle {\ce {-}}} in place of the isopropyl [ CH ( CH 3 ) 2 ] {\textstyle {\ce {-}}} and ethyl group, respectively.The sim-azine molecule with 2 ethyl groups is symmetric and flat (excepting its equal NH C 2 H 5 {\textstyle {\ce {NH-C2H5}}} ends). The threefold substituted triazines have resonance of the free (non-bonding, π {\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) and can migrate from soil to groundwater.>

References

  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.
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