simazine
{{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-N2,N4-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/cm3
| MeltingPtC=225-227
| BoilingPt=
| Solubility=5 mg/L
| SolubleOther = Soluble in methanol, chloroform, and diethyl ether; slightly soluble in pentane
| Solvent=other solvents
| VaporPressure =0.000810 mPa at 20 °C
| LogP = 1.9600
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
Simazine is an herbicide of the triazine class. The compound is used to control broad-leaved weeds and annual grasses.
Preparation
Simazine may be prepared from cyanuric chloride and a concentrated solution of ethyl amine (at least 50 percent by number) in water.{{cite web | url = https://pubchem.ncbi.nlm.nih.gov/compound/Simazine#section=Methods-of-Manufacturing&fullscreen=true | title = Simazine: Methods of Manufacturing | publisher = PubChem }} The reaction is highly exothermic and is therefore best carried out below 10 °C.
Cyanuric chloride decomposes at high temperatures into hydrogen chloride and 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.{{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}} Like atrazine, a related triazine herbicide, it acts by inhibiting photosynthesis. It remains active in the soil for two to seven months or longer after application.
==See also==
References
{{reflist}}
External links
- [http://extoxnet.orst.edu/pips/simazine.htm Simazine], Extoxnet PIP
{{Herbicides}}