Simazine

Simazine is a herbicide of the triazine class. The compound is used to control broad-leaved weeds and annual grasses.

Simazine
Names
IUPAC name
6-Chloro-N,N'-diethyl-1,3,5-triazine-2,4-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.124
KEGG
UNII
Properties
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)
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).
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Infobox references

Preparation

Simazine may be prepared in the laboratory from cyanuric chloride crystals and a strong solution of ethyl amine (at least 50 percent by number in water). 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 nonselective herbicide, but is now banned in European Union states.[1] Like atrazine, a related triazine herbicide, it acts by inhibiting photosynthesis. It remains active in the soil for 2-7 months or longer after application.

See also

References
  1. EU directive 91/414/EEC
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