Mepanipyrim

Structural formula
General
Surname	Mepanipyrim
other names	4-methyl- N -phenyl-6- (1-propynyl) -2-pyrimidinamine; N - (4-methyl-6-prop-1-ynylpyrimidin-2-yl) aniline ( IUPAC );
Molecular formula	C 14 H 13 N 3
Brief description	light yellow, odorless solid
External identifiers / databases
EC number	600-951-7
ECHA InfoCard	100.120.151
PubChem	86296
ChemSpider	77839
Wikidata	Q15632906
properties
Molar mass	223.27 g mol −1
Physical state	firmly
density	1.2 g cm −3
Melting point	132.8 ° C
boiling point	288 ° C (decomposition)
Vapor pressure	2.32 10 −5 Pa (25 ° C)
solubility	practically insoluble in water (3.1 mg l −1 at 20 ° C); soluble in acetone , ethyl acetate , toluene and dichloromethane ;
safety instructions
H and P phrases	H: 351-410
	P: 273-281-501
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 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 .

Mepanipyrim is a chemical compound from the group of pyrimidines , more precisely the anilinopyrimidines .

Extraction and presentation

Mepanipyrim can be obtained by reacting 2-thiomethyl-4-methyl-6-propynylpyrimidine with hydrogen peroxide , formanilide and hydrogen chloride .

properties

Mepanipyrim is a light yellow odorless powder that is practically insoluble in water. It is stable to hydrolysis at pH values of 5, 7 and 9.

use

Mepanipyrim is used as a fungicide primarily against gray mold ( Botrytis cinerea ) from vines and vegetables, but also scab ( Venturia sp. ) From apples and pears and brown rot ( Monilinia fructicola ) from peaches. The effect is based on the inhibition of mycelial growth, whereby effects on transport mechanisms are probably responsible for its antifungal effect.

Admission

The compound was launched on the market in 1995 and on October 24, 1997, Kumiai Chemical Industry in Italy submitted an application for approval in the EU. Mepanipyrim has been approved for use as a fungicide in the European Union since 2004. The first approval in Germany was granted in 2006.

In some EU countries, including Austria and Switzerland, plant protection products with this active ingredient are permitted, but not in Germany.

Trade names

Frupica

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on mepanipyrim in the GESTIS substance database of the IFA , accessed on January 14, 2013(JavaScript required) .
↑ ^a ^b ^c ^d data sheet Mepanipyrim at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f ^g EU: Review report for the active substance mepanipyrim (PDF; 276 kB), March 29, 2004
↑ Entry on 4-methyl-N-phenyl-6- (1-propynyl) -2-pyrimidinamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and labeling expand .
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 559 ( limited preview in Google Book search).
↑ EFSA: Review of the existing maximum residue levels (MRLs) for mepanipyrim according to Article 12 of Regulation (EC) No 396/2005. In: EFSA Journal. 9, 2011, p. 2342, doi : 10.2903 / j.efsa.2011.2342 .
↑ Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 707 ( limited preview in Google Book search).
↑ Implementing Regulation (EU) No. 540/2011 of the Commission of 25 May 2011 for the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances (PDF)
↑ Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer DE, 2010, ISBN 3-0348-0028-2 , pp. 20 .
^ Directorate-General for Health and Food Safety of the European Commission: Entry on Mepanipyrim 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] Entry on mepanipyrim in the GESTIS substance database of the IFA , accessed on January 14, 2013(JavaScript required) .

[Sigma-2] ta sheet Mepanipyrim at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[EU-3] ↑ ^a ^b ^c ^d ^e ^f ^g EU: Review report for the active substance mepanipyrim (PDF; 276 kB), March 29, 2004

[CLP_100.120.151-4] Entry on 4-methyl-N-phenyl-6- (1-propynyl) -2-pyrimidinamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and labeling expand .

[Unger-5] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 559 ( limited preview in Google Book search).

[6] EFSA: Review of the existing maximum residue levels (MRLs) for mepanipyrim according to Article 12 of Regulation (EC) No 396/2005. In: EFSA Journal. 9, 2011, p. 2342, doi : 10.2903 / j.efsa.2011.2342 .

[Wolfgang_Krämer,_Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-7] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 707 ( limited preview in Google Book search).

[8] Implementing Regulation (EU) No. 540/2011 of the Commission of 25 May 2011 for the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances (PDF)

[Peter_Brandt-9] Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer DE, 2010, ISBN 3-0348-0028-2 , pp. 20 .

[PSM-10] Directorate-General for Health and Food Safety of the European Commission: Entry on Mepanipyrim in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.