Simazine
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.
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| Names | |
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| Preferred IUPAC name
6-Chloro-N2,N4-diethyl-1,3,5-triazine-2,4-diamine | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.124 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
[edit]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
[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.[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
[edit]References
[edit]- ^ "Classification of Herbicides According to Site of Action". Retrieved 19 July 2025.
- ^ "Simazine: Methods of Manufacturing". PubChem.
- ^ 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]- Simazine, Extoxnet PIP