Pyraclostrobin

Structural formula
General
Surname	Pyraclostrobin
other names	Methyl (2- (1- (4-chlorophenyl) -1 H -pyrazole-3-yloxymethyl) phenyl) methoxycarbamate; Methyl N - (2- [1- (4-chlorophenyl) -1 H -pyrazol-3-yl] oxymethylphenyl) - ( N -methoxy) carbamate ( IUPAC );
Molecular formula	C 19 H 18 ClN 3 O 4
Brief description	yellow solid with a slightly aromatic odor
External identifiers / databases
EC number	605-747-1
ECHA InfoCard	100.125.533
PubChem	6422843
Wikidata	Q1961265
properties
Molar mass	387.82 g mol −1
Physical state	firmly
density	1.29 g cm −3
Melting point	59-62 ° C
boiling point	200 ° C (decomposition)
Vapor pressure	2.6 10 −10 hPa (20 ° C)
solubility	practically insoluble in water (1.9 mg l −1 at 20 ° C); soluble in acetone, acetonitrile, dichloromethane, ethyl acetate and toluene;
safety instructions
H and P phrases	H: 331-315-410
	P: 273-302 + 352-304 + 340 + 311
Toxicological data	> 5,000 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 .

Pyraclostrobin is a chemical compound from the group of strobilurins that is used in agriculture.

Extraction and presentation

Pyraclostrobin is chemically produced by reacting 4-chlorophenyl hydrazine with ethyl acrylate and oxygen to form pyrazole, alkylation with 2-nitrobenzyl chloride , catalytic hydrogenation to form hydroxylamine and subsequent reaction with methyl chloroformate and dimethyl sulfate .

properties

As a pure substance, pyraclostrobin is an odorless, colorless solid. The technical product is a flammable yellow solid with a weak aromatic odor, which is practically insoluble in water. In an aqueous solution in the dark it is stable at pH 4, 5 and 7 (25 ° C and 50 ° C). At a pH of 9, a very slow degradation is observed at normal ambient temperature.

use

Estimated US application rate in 2011

Pyraclostrobin is used as an active ingredient in crop protection products. It is used as a fungicide and works by inhibiting mitochondrial respiration. This leads to a reduction in the amount of ATP available in the fungal cell. It has been marketed by BASF since 2002 .

Admission

The use of pyraclostrobin as a fungicide in plant protection products has been permitted in the European Union since 2004, and since 2009 its use as a growth regulator has also been permitted. In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved.

Web links

Joint Meeting on Pesticide Residues (JMPR), Monograph for PYRACLOSTROBIN

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on pyraclostrobin in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f FAO: PYRACLOSTROBIN (210) - First draft prepared by Bernard Declercq, Epinay sur Orge, France (PDF; 1.2 MB)
↑ Pyraclostrobin data sheet , PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ ^a ^b Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 618 (English, limited preview in Google Book search).
↑ Directive 2009/25 / EC of the Commission of April 2, 2009 amending Directive 91/414 / EEC of the Council with regard to an extension of the uses of the active ingredient pyraclostrobin
↑ General Directorate Health and Food Safety of the European Commission: Entry on pyraclostrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on pyraclostrobin in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[FAO-2] ↑ ^a ^b ^c ^d ^e ^f FAO: PYRACLOSTROBIN (210) - First draft prepared by Bernard Declercq, Epinay sur Orge, France (PDF; 1.2 MB)

[Sigma-3] Pyraclostrobin data sheet , PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[von_Wolfgang_Krämer,Ulrich_Schirmer-4] Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 618 (English, limited preview in Google Book search).

[5] Directive 2009/25 / EC of the Commission of April 2, 2009 amending Directive 91/414 / EEC of the Council with regard to an extension of the uses of the active ingredient pyraclostrobin

[PSM-6] General Directorate Health and Food Safety of the European Commission: Entry on pyraclostrobin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.