Simazine

Simazine
Skeletal formula of simazine
Space-filling model of simazine
Names
Preferred IUPAC name
6-Chloro-N2,N4-diethyl-1,3,5-triazine-2,4-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.124 Edit this at Wikidata
KEGG
UNII
  • 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
    Key: ODCWYMIRDDJXKW-UHFFFAOYSA-N 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)
    Key: ODCWYMIRDDJXKW-UHFFFAOYAN
  • Clc1nc(nc(n1)NCC)NCC
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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Simazine is an herbicide of the triazine class. The compound is used to control broad-leaved weeds and annual grasses.

Simazine's HRAC classification is Group C1, Group C (global, Aus), Group 5 (numeric), as it inhibits photosynthesis at photosystem II.[1]

Preparation

Simazine may be prepared from cyanuric chloride and a concentrated solution of ethyl amine (at least 50 percent by number) in water.[2] 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.[3] 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

  1. ^ "Classification of Herbicides According to Site of Action". Retrieved 19 July 2025.
  2. ^ "Simazine: Methods of Manufacturing". PubChem.
  3. ^ 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

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