Pyrazosulfuron-ethyl

Structural formula
General
Surname	Pyrazosulfuron-ethyl
other names	Ethyl-5 - [({[(4,6-dimethoxypyrimidin-2-yl) amino] carbonyl} amino) sulfonyl] -1-methyl-1 H -pyrazole-4-carboxylate
Molecular formula	C 14 H 18 N 6 O 7 S
Brief description	colorless, crystalline solid
External identifiers / databases
EC number	618-964-1
ECHA InfoCard	100.108.299
PubChem	91750
Wikidata	Q16855864
properties
Molar mass	414.40 g mol −1
Physical state	firmly
Melting point	181-182 ° C
solubility	practically insoluble in water: 9.76 mg l −1 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pyrazosulfuron-ethyl is a chemical compound from the group of sulfonylureas and a herbicide , which was discovered in 1982 and brought to market by Nissan Chemical in 1990 .

Extraction and presentation

Pyrazosulfuron-ethyl can be prepared starting from methylhydrazine and ethoxycyaneacetic acid ethyl ester ( English ethyl ethoxy acrylo cyano acetate ). Pyrazosulfuron is formed by reaction with sodium nitrite , sulfur dioxide , ammonia , phosgene and the addition of 2-amino-4,6-dimethoxypyrimidine.

use

Pyrazosulfuron-ethyl is used as a systemic herbicide in rice cultivation under the trade names Agreen and Sirius . It works by inhibiting acetolactate synthase . In the European Union and in Switzerland it is not approved as a crop protection agent.

Individual evidence

↑ ^a ^b ^c ^d ^e entry on pyrazosulfuron-ethyl. In: Römpp Online . Georg Thieme Verlag, accessed on May 6, 2014.
↑ ^a ^b data sheet pyrazosulfuron-ethyl from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ Neera Singh, Shashi B Singh: Translocation and degradation of pyrazosulfuron-ethyl in rice soil . In: Pest Management Science . tape 67 , no. 11 , November 2011, p. 1451-1456 , doi : 10.1002 / ps.2199 ( PDF ).
↑ Katsushi Morimoto, Kenzi Makino, Susumu Yamamoto, Gozyo Sakata: Synthesis of fluoromethyl, difluoromethyl and trifluoromethyl analogues of pyrazosulfuron-ethyl as herbicides . In: Journal of Heterocyclic Chemistry . tape 27 , no. 3 , March 1990, p. 807-810 , doi : 10.1002 / jhet.5570270360 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 194 ( limited preview in Google Book search).
^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 20, 2016.

[roempp-1] ↑ ^a ^b ^c ^d ^e entry on pyrazosulfuron-ethyl. In: Römpp Online . Georg Thieme Verlag, accessed on May 6, 2014.

[Sigma-2] ta sheet pyrazosulfuron-ethyl from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[3] Neera Singh, Shashi B Singh: Translocation and degradation of pyrazosulfuron-ethyl in rice soil . In: Pest Management Science . tape 67 , no. 11 , November 2011, p. 1451-1456 , doi : 10.1002 / ps.2199 ( PDF ).

[4] Katsushi Morimoto, Kenzi Makino, Susumu Yamamoto, Gozyo Sakata: Synthesis of fluoromethyl, difluoromethyl and trifluoromethyl analogues of pyrazosulfuron-ethyl as herbicides . In: Journal of Heterocyclic Chemistry . tape 27 , no. 3 , March 1990, p. 807-810 , doi : 10.1002 / jhet.5570270360 ( PDF ).

[unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 194 ( limited preview in Google Book search).

[6] Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 20, 2016.