Bupirimate

Structural formula
General
Surname	Bupirimate
other names	5-butyl-2-ethylamino-6-methylpyrimidin-4-yl-dimethylsulfamate; Nimrod;
Molecular formula	C 13 H 24 N 4 O 3 S
Brief description	brown solid
External identifiers / databases
EC number	255-391-2
ECHA InfoCard	100.050.339
PubChem	38884
Wikidata	Q2928285
properties
Molar mass	316.42 g mol −1
Physical state	firmly
density	1.2 g cm −3
Melting point	50–51 ° C (light brown waxy substance); 40–45 ° C (technical product);
solubility	practically insoluble in water (22 mg l −1 )
safety instructions
H and P phrases	H: 351-317-410
	P: 280
Toxicological data	4000 mg kg −1 ( LD 50 , rat , oral ) ; 500 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bupirimate is a chemical compound from the group of pyrimidines and sulfamates , which was introduced by ICI as a systemic fungicide . Bupirimate belongs to the 2-aminopyrimidine fungicides and was used under the trade name Nimrod in pome fruit, stone fruit and ornamental plant cultivation against powdery mildew fungi . The active ingredient inhibits adenosine deaminase .

Extraction and presentation

Bupirimate can be obtained from ethirimol . This reacts with sodium hydroxide and dimethylsulfamoyl chloride to form bupirimate.

Admission

Bupirimate was approved as a plant protection product in the Federal Republic of Germany from 1976 to 1989. Bupirimate has been approved as an active ingredient in the European Union since 2011.

In Switzerland and a number of EU countries, plant protection products with this active ingredient are approved, including Germany and Austria.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on Bupimirat in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ ^a ^b ^c Entry on bupirimate. In: Römpp Online . Georg Thieme Verlag, accessed on January 3, 2015.
↑ Entry on bupirimate (ISO); 5-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulphamate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 17, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Bupirimate data sheet at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 545 ( limited preview in Google Book search).

↑ BVL approval history .

↑ Directive 2011/25 / EU (PDF) of the Commission of March 3, 2011 amending Council Directive 91/414 / EEC to include the active substance bupirimate.

↑ General Directorate Health and Food Safety of the European Commission: Entry on Bupirimate in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f Entry on Bupimirat in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[roempp-2] Entry on bupirimate. In: Römpp Online . Georg Thieme Verlag, accessed on January 3, 2015.

[CLP_100.050.339-3] Entry on bupirimate (ISO); 5-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulphamate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 17, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[Sigma-4] Bupirimate data sheet at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

[unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 545 ( limited preview in Google Book search).

[6] BVL approval history .

[7] Directive 2011/25 / EU (PDF) of the Commission of March 3, 2011 amending Council Directive 91/414 / EEC to include the active substance bupirimate.

[8] General Directorate Health and Food Safety of the European Commission: Entry on Bupirimate in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.