Simazine
| Simazine | |
|---|---|
| File:Simazine Structural Formulae .V.1.svg | |
| 6-chloro-N,N'-diethyl-1,3,5-triazine-2,4-diamine | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 122-34-9 
|
| PubChem | 5216 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C7H12ClN5 |
| Molar mass | 201.657 g/mol |
| Appearance | White crystalline powder |
| Density | 1.3 kg/dm3 |
| Melting point |
225-227 °C |
| Solubility in water | Insoluble (5 mg/L water) |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Simazine is a herbicide of the triazine class. The compound is used to control broad-leaved weeds and annual grasses.
Contents
Physical properties
- Water solubility: 5 mg/L at 20 °C
- Solubility in other solvents: s. in methanol, chloroform, and diethyl ether [6]; s.s. in pentane
- Vapor pressure: 0.000810 mPa at 20 °C
- Partition coefficient: 1.9600
- Adsorption coefficient: 130
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 (see also atrazine), and was widely used as a residual nonselective herbicide, but is now banned in European Union states (EU directive 91/414/EEC). Like atrazine, it acts by inhibiting photosynthesis. It remains active in the soil for 2-7 months after application.
Synthesis mechanism
This is the first part of the mechanism. It produces the product simazine and adds 4 equivalents of ethylamine instead of 2.
