Metconazole

Structural formula
	Structural formula without stereochemistry
General
Surname	Metconazole
other names	(1 RS , 5 RS ; 1 RS , 5 SR ) -5- (4-chlorobenzyl) -2,2-dimethyl-1- (1 H -1,2,4-triazol-1-ylmethyl) cyclopentanol; (1 RS , 5 RS ; 1 RS , 5 SR ) -5- (4-chlorobenzyl) -2,2-dimethyl-1- (1 H -1,2,4-triazol-1-ylmethyl) cyclopentanol;
Molecular formula	C 17 H 22 ClN 3 O
Brief description	off-white odorless solid
External identifiers / databases
EC number	603-031-3
ECHA InfoCard	100.125.390
PubChem	86210
ChemSpider	77764
Wikidata	Q1519339
properties
Molar mass	319.83 g mol −1
Physical state	firmly
density	1.14 g cm −3
Melting point	110-113 ° C
boiling point	285 ° C
Vapor pressure	0.21 mPa (25 ° C)
solubility	practically insoluble in water (15 mg l −1 at 20 ° C); soluble in methanol and acetone;
safety instructions
H and P phrases	H: 302-361d-411
	P: 201-273-301 + 312 + 330-308 + 313
Toxicological data	1459 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 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 .

Metconazole is an active ingredient for crop protection and a mixture of four stereoisomeric chemical compounds from the group of triazoles .

Extraction and presentation

Metconazole can be obtained by a multistage reaction beginning with a Dieckmann condensation of ethyl adipate to 2-ethoxycarbonylcyclopentanone and, after several intermediate steps, a Corey-Chaykovsky epoxidation of 1,2,4-triazole with trimethylsulfoxonium bromide and cyclopentanone.

properties

Metconazole is a white solid. The commercially available product is a four-component mixture of cis form [1: 1 mixture of (1 R , 5 S ) and (1 S , 5 R ) isomer] and trans form [1: 1 mixture of (1 R , 5 R ) - and (1 S , 5 S ) -isomer].

Stereochemistry

Generally speaking, chemical compounds with multiple stereocenters form up to 2 ⁿ stereoisomers . Here n is the number of stereocenters. Accordingly, there are four stereoisomers in metconazole, which have also been confirmed experimentally. It is a mixture of (1 S , 5 S ) -, (1 R , 5 R ) -, (1 R , 5 S ) - and the (1 S , 5 R ) form:

Four stereoisomers (two pairs of diastereomers)
1: 1 mixture ( racemate ) CAS number: 115850-28-7
1: 1 mixture (racemate) CAS number: 115850-27-6

use

Metconazole is a fungicide that was launched on the market in 1992 ; it is mainly used in cereals and rapeseed. It was developed by the Japanese chemical company Kureha and is also marketed by BASF .

Admission

With effect from June 1, 2007, metconazole was approved as a fungicidal active ingredient in the European Union.

In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d Entry on metconazole in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c Müller, F .; Ackermann, P .; Margot, P .: Fungicides, Agricultural, 2. Individual Fungicides in Ullmanns Enzyklopädie der Technischen Chemie , 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.o12_o06 .
↑ ^a ^b ^c ^d data sheet Metconazole, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ ^a ^b ^c ^d Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 ( page 784ff in the Google book search).
↑ ^a ^b Ullmann's Agrochemicals, Volume 1 . Wiley-VCH, 2007, ISBN 978-3-527-31604-5 ( page 614 in the Google book search).
↑ Entry on (1RS, 5RS; 1RS, 5SR) -5- (4-chlorobenzyl) -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.
↑ Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4 1 , see p. 10.
↑ The European Commission: 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. May 2011, p. 47 , accessed January 26, 2018 .
↑ Directive 2006/74 / EC of the Commission of August 21, 2006 [amending Directive 91/414 / EEC of the Council to include the active substances dichlorprop-P, metconazole, pyrimethanil and triclopyr ] .
↑ General Directorate Health and Food Safety of the European Commission: Entry on Metconazole 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] Entry on metconazole in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[UllmannTC-2] Müller, F .; Ackermann, P .; Margot, P .: Fungicides, Agricultural, 2. Individual Fungicides in Ullmanns Enzyklopädie der Technischen Chemie , 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.o12_o06 .

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

[ModernCPC-4] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 ( page 784ff in the Google book search).

[ullmann-5] Ullmann's Agrochemicals, Volume 1 . Wiley-VCH, 2007, ISBN 978-3-527-31604-5 ( page 614 in the Google book search).

[CLP_100.125.390-6] Entry on (1RS, 5RS; 1RS, 5SR) -5- (4-chlorobenzyl) -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[7] Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.

[Ulrich-8] Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4 1 , see p. 10.

[EU-9] The European Commission: 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. May 2011, p. 47 , accessed January 26, 2018 .

[10] Directive 2006/74 / EC of the Commission of August 21, 2006 [amending Directive 91/414 / EEC of the Council to include the active substances dichlorprop-P, metconazole, pyrimethanil and triclopyr ] .

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on Metconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.