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

Skeletal formula of simazine
Space-filling model of simazine
Preferred IUPAC name
3D model (JSmol)
ECHA InfoCard 100.004.124 Edit this at Wikidata
  • 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) checkY
  • 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)
  • Clc1nc(nc(n1)NCC)NCC
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).
☒N verify (what is checkY☒N ?)

Preparation edit

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 edit

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.

See also edit

References edit

  1. ^ "Simazine: Methods of Manufacturing". PubChem.
  2. ^ 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

External links edit