Simazine Knowpia

Simazine
Names
	Preferred IUPAC name 6-Chloro-N2,N4-diethyl-1,3,5-triazine-2,4-diamine
Identifiers
CAS Number	122-34-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27496 ;
ChEMBL	ChEMBL1605837 ;
ChemSpider	5027 ;
ECHA InfoCard	100.004.124
KEGG	C11172 ;
PubChem CID	5216;
UNII	SG0C34SMY3 ;
CompTox Dashboard (EPA)	DTXSID4021268 ;
	InChI 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) Key: ODCWYMIRDDJXKW-UHFFFAOYSA-N ; 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;
	SMILES Clc1nc(nc(n1)NCC)NCC;
Properties
Chemical formula	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)
Solubility in water	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). verify (what is ?) Infobox references

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

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.

References edit

^ "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

[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

[1]

[2]

Summary

Preparation edit

Properties and uses edit

See also edit

References edit

External links edit

Names


Preferred IUPAC name 6-Chloro-N²,N⁴-diethyl-1,3,5-triazine-2,4-diamine
Identifiers
CAS Number	122-34-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27496^Y
ChEMBL	ChEMBL1605837^N
ChemSpider	5027^Y
ECHA InfoCard	100.004.124
KEGG	C11172^Y
PubChem CID	5216
UNII	SG0C34SMY3^Y
CompTox Dashboard (EPA)	DTXSID4021268
InChI 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)^Y Key: ODCWYMIRDDJXKW-UHFFFAOYSA-N^Y 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
SMILES Clc1nc(nc(n1)NCC)NCC
Properties
Chemical formula	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)
Solubility in water	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 ^YN ?) Infobox references