Simazine

Names
Preferred IUPAC name 6-Chloro-N2,N4-diethyl-1,3,5-triazine-2,4-diamine
Identifiers
CAS Number	122-34-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27496 Y
ChEMBL	ChEMBL1605837 N
ChemSpider	5027 Y
ECHA InfoCard	100.004.124
KEGG	C11172 Y
PubChem CID	5216
UNII	SG0C34SMY3 Y
CompTox Dashboard (EPA)	DTXSID4021268
InChI InChI=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) Y Key: ODCWYMIRDDJXKW-UHFFFAOYSA-N Y 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) Key: ODCWYMIRDDJXKW-UHFFFAOYAN
SMILES Clc1nc(nc(n1)NCC)NCC
Properties
Chemical formula	C7H12ClN5
Molar mass	201.66 g·mol−1
Appearance	White crystalline powder
Density	1.3 g/cm3
Melting point	225–227 °C (437–441 °F; 498–500 K)
Solubility in water	5 mg/L
Solubility in other solvents	Soluble in methanol, chloroform, and diethyl ether; slightly soluble in pentane
log P	1.9600
Vapor pressure	0.000810 mPa at 20 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.^[1] The reaction is highly exothermic and is therefore best carried out in an ice bath below 10 °C. It is also essential to carry out the synthesis in a fume hood since 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.^[2] 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.