# Simazine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Simazine
> Markdown URL: https://mediated.wiki/source/Simazine.md
> Source: https://en.wikipedia.org/wiki/Simazine
> Source revision: 1306127098
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464391754
| ImageFile = Simazine.svg
| ImageSize = 200px
| ImageAlt = Skeletal formula of simazine
| ImageFile1 = Simazine-3D-spacefill.png
| ImageAlt1 = Space-filling model of simazine
| PIN=6-Chloro-''N''<sup>2</sup>,''N''<sup>4</sup>-diethyl-1,3,5-triazine-2,4-diamine
| OtherNames=
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5027
| InChI = 1/C7H12ClN5/c1-3-9-6-11-5(8)12-7(13-6)10-4-2/h3-4H2,1-2H3,(H2,9,10,11,12,13)
| InChIKey = ODCWYMIRDDJXKW-UHFFFAOYAN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H12ClN5/c1-3-9-6-11-5(8)12-7(13-6)10-4-2/h3-4H2,1-2H3,(H2,9,10,11,12,13)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ODCWYMIRDDJXKW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=122-34-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SG0C34SMY3
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1605837
| PubChem=5216
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11172
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27496
| SMILES = Clc1nc(nc(n1)NCC)NCC
}}
|Section2={{Chembox Properties
| C=7 | H=12 | Cl=1 | N=5
| Appearance=White crystalline powder
| Density=1.3 g/cm<sup>3</sup>
| MeltingPtC=225-227
| BoilingPt=
| Solubility=5 mg/L
| SolubleOther = Soluble in [methanol](/source/methanol), [chloroform](/source/chloroform), and [diethyl ether](/source/diethyl_ether); slightly soluble in [pentane](/source/pentane)
| Solvent=other solvents
| VaporPressure =0.000810 mPa at 20&nbsp;°C
| LogP = 1.9600 
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}

'''Simazine''' is an [herbicide](/source/herbicide) of the [triazine](/source/triazine) class. The compound is used to control broad-leaved [weed](/source/weed)s and [annual](/source/Annual_plant) [grasses](/source/grasses).

Simazine's [HRAC classification](/source/HRAC_classification) is [Group C1, Group C](/source/%3ACategory%3AGroup_5_herbicides) (global, Aus), [Group 5](/source/%3ACategory%3AGroup_5_herbicides) (numeric), as it inhibits [photosynthesis](/source/photosynthesis) at [photosystem II](/source/photosystem_II).<ref>{{cite web |title=Classification of Herbicides According to Site of Action |url=https://www.weedscience.org/Documents/ShowDocuments.aspx?DocumentID=1193 |access-date=19 July 2025}}</ref>

==Preparation==
Simazine may be prepared from [cyanuric chloride](/source/cyanuric_chloride) and a concentrated solution of [ethyl amine](/source/ethyl_amine) (at least 50&nbsp;percent by number) in water.<ref>{{cite web | url = https://pubchem.ncbi.nlm.nih.gov/compound/Simazine#section=Methods-of-Manufacturing&fullscreen=true | title = Simazine: Methods of Manufacturing | publisher = [PubChem](/source/PubChem) }}</ref> The reaction is highly [exothermic](/source/exothermic) and is therefore best carried out below 10&nbsp;°C.

Cyanuric chloride decomposes at high temperatures into [hydrogen chloride](/source/hydrogen_chloride) and [hydrogen cyanide](/source/hydrogen_cyanide), both of which are highly toxic by inhalation.

==Properties and uses==
Simazine is an off-white crystalline compound which is sparingly soluble in water.  It is a member of the triazine-derivative herbicides, and was widely used as a residual non-selective herbicide, but is now banned in European Union states.<ref>{{CELEX|32004D0247|language=EN|format=PDF|text = 2004/247/EC: Commission Decision of 10 March 2004 concerning the non-inclusion of simazine in Annex I to Council Directive 91/414/EEC and the withdrawal of authorisations for plant protection products containing this active substance}}</ref>  Like [atrazine](/source/atrazine), a related triazine herbicide, it acts by inhibiting [photosynthesis](/source/photosynthesis).  It remains active in the soil for two to seven months or longer after application.

==See also== 
* [Atrazine](/source/Atrazine)

==References==
{{reflist}}

==External links==
* [http://extoxnet.orst.edu/pips/simazine.htm Simazine], Extoxnet PIP 

{{Herbicides}}

Category:Herbicides
Category:Triazines
Category:Chloroarenes
Category:Group 5 herbicides

---
Adapted from the Wikipedia article [Simazine](https://en.wikipedia.org/wiki/Simazine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Simazine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.