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}}