Prometryn

Structural formula
General
Surname	Prometryn
other names	2-methylthio-4,6-bis (isopropylamino) -1,3,5-triazine; 2,4-bis (isopropylamino) -6-methylmercapto- S- triazine; 2,4-bis (isopropylamino) -6-methylthio-1,3,5-triazine; Caparol;
Molecular formula	C 10 H 19 N 5 S
Brief description	colorless and odorless solid
External identifiers / databases
EC number	230-711-3
ECHA InfoCard	100,027,919
PubChem	4929
Wikidata	Q1257341
properties
Molar mass	241.36 g mol −1
Physical state	firmly
density	1.157 g cm −3
Melting point	119 ° C
pK s value	4.05
solubility	almost insoluble in water (33 mg l −1 at 25 ° C); soluble in acetone , ethanol , dichloromethane and toluene ;
safety instructions
H and P phrases	H: 332-400
	P: 273
Toxicological data	2100 mg kg −1 ( LD 50 , rat , oral ) ; 3100 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Prometryn is a chemical compound from the triazine group and the methylthio analogue of propazine .

Extraction and presentation

Prometryn can be prepared by reacting 2-chloro-4,6-bis (isopropylamine) - S -triazine with sodium methyl thiolate or by reacting propazine with methyl mercaptan in the presence of sodium hydroxide .

properties

Prometryn is a flammable, colorless and odorless solid that is insoluble in water. It is stable against hydrolysis at 20 ° C in neutral and weakly acidic or weakly alkaline media, but it hydrolyzes with warm acids and alkalis and decomposes when exposed to UV light .

use

Prometryn is used as a plant protection product. It was approved in the United States in 1964 as a herbicide to control weeds in cotton , celery , pigeon pea and dill crops . The effect is based on the inhibition of photosynthesis in photosystem II .

Admission

Prometryn is not on the list of active plant protection ingredients approved in the European Union . In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on Prometryn in the GESTIS substance database of the IFA , accessed on February 9, 2017(JavaScript required) .
↑ ^a ^b ^c ^d ^e Entry on PROMETRYNE in the Hazardous Substances Data Bank , accessed on June 26, 2012.
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 656 ( limited preview in Google Book search).
↑ EPA: Reregistration Eligibility Decision (RED) - Prometryn (PDF; 548 kB)
↑ Overview of Case Study - Prometryn (PDF; 4.0 MB)
↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 extending the deadline in accordance with Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this directive as well as the revocation of the Approvals of plant protection products with these active ingredients (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on Prometryn in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on Prometryn in the GESTIS substance database of the IFA , accessed on February 9, 2017(JavaScript required) .

[HSDB-2] Entry on PROMETRYNE in the Hazardous Substances Data Bank , accessed on June 26, 2012.

[Unger-3] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 656 ( limited preview in Google Book search).

[EPA-4] EPA: Reregistration Eligibility Decision (RED) - Prometryn (PDF; 548 kB)

[5] Overview of Case Study - Prometryn (PDF; 4.0 MB)

[6] Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 extending the deadline in accordance with Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this directive as well as the revocation of the Approvals of plant protection products with these active ingredients (PDF)

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on Prometryn in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.