Bitertanol

Structural formula
	General structural formula without information on stereochemistry - mixture of four isomers
General
Surname	Bitertanol
other names	(1 RS , 2 RS ; 1 RS , 2 SR ) -1- (biphenyl-4-yloxy) -3,3-dimethyl-1- (1 H -1,2,4-triazol-1-yl) butane 2-ol ( IUPAC ); β - ([1,1'-biphenyl] -4-yloxy) -α- (1,1-dimethylethyl) -1 H -1,2,4-triazole-1-ethanol;
Molecular formula	C 20 H 23 N 3 O 2
Brief description	colorless solid
External identifiers / databases
EC number	259-513-5
ECHA InfoCard	100.054.084
PubChem	91656
Wikidata	Q1821798
properties
Molar mass	337.42 g mol −1
Physical state	firmly
density	1.16 g cm −3
Melting point	118 ° C (Eutecticum); 136-137 ° C (technical product);
boiling point	300 ° C (decomposition)
Vapor pressure	1.36 nPa (25 ° C)
solubility	almost insoluble in water; soluble in acetone, dichloromethane, ethyl acetate and dimethyl sulfoxide;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 302-330
	P: 260-284-310
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 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 .

Bitertanol is a mixture of four isomeric chemical compounds from the groups of the triazoles and the biphenyl - derivatives .

Extraction and presentation

Bitertanol can be produced by a multi-stage reaction of 3,3-dimethylbutan-1-one by chlorination with elemental chlorine , by subsequent nucleophilic substitution of the chlorine atom with 4-phenylphenol , bromination with elemental bromine , renewed nucleophilic substitution with 1,2,4-triazole and reducing the ketone with hydrogen .

properties

Bitertanol is a colorless solid that is insoluble in water. The technical product is a 20:80 mixture of the (1 RS , 2 RS ) and (1 RS , 2 SR ) isomers .

Stereoisomers of Bitertanols indicating the CIP - Configuration and the content in the technical product
(1 R , 2 R ) -Bitertanol (approx. 10%)
(1 S , 2 S ) -Bitertanol (approx. 10%)
(1 R , 2 S ) -Bitertanol (approx. 40%)
(1 S , 2 R ) -Bitertanol (approx. 40%)

It is very stable to photolysis and hydrolysis . The half-life in aqueous suspension is 39.2 days.

use

Bitertanol is used as a preventive or curative fungicide to combat certain diseases in fruit and vegetables, including scab and Monilia laxa in stone fruit, and to treat seeds against Fusarium spp. , Septoria , Weizensteinbrand etc. It was brought onto the market by Bayer in 1979 .

Admission

The European Union allowed its use as an active ingredient in plant protection products with effect from January 1, 2012 for applications as a fungicide for seed treatment .

In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Bitertanol data sheet , PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ ^a ^b ^c F. Müller, P. Ackermann, P. Margot: Fungicides, Agricultural, 2. Individual Fungicides. In: Ullmann's Encyclopedia of Technical Chemistry . Wiley-VCH, Weinheim 2012, doi : 10.1002 / 14356007.o12_o06 .
↑ ^a ^b ^c ^d ^e ^f EFSA: Conclusion on the peer review of the pesticide risk assessment of the active substance bitertanol , 2010. doi : 10.2903 / j.efsa.2010.1850
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-08-095716-1 , pp. 685 ( limited preview in Google Book search).
^ Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 2, Insecticides and fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 1018 ( limited preview in Google Book search).
↑ FAO: Bitertanol (PDF; 548 kB).
↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 771 ( limited preview in Google Book search).
↑ Implementing Regulation (EU) No. 1278/2011 of the Commission of December 8, 2011 for the approval of the active ingredient Bitertanol according to Regulation (EC) No. 1107/2009 ... (PDF) .
↑ General Directorate Health and Food Safety of the European Commission: Entry on Bitertanol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 22, 2016.

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g Bitertanol data sheet , PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[Ullmann-2] F. Müller, P. Ackermann, P. Margot: Fungicides, Agricultural, 2. Individual Fungicides. In: Ullmann's Encyclopedia of Technical Chemistry . Wiley-VCH, Weinheim 2012, doi : 10.1002 / 14356007.o12_o06 .

[EFSA-3] ↑ ^a ^b ^c ^d ^e ^f EFSA: Conclusion on the peer review of the pesticide risk assessment of the active substance bitertanol , 2010. doi : 10.2903 / j.efsa.2010.1850

[Thomas_A._Unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-08-095716-1 , pp. 685 ( limited preview in Google Book search).

[Terence_Robert_Roberts,_David_Herd_Hutson-5] Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 2, Insecticides and fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 1018 ( limited preview in Google Book search).

[FAO-6] FAO: Bitertanol (PDF; 548 kB).

[Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-7] Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 771 ( limited preview in Google Book search).

[8] Implementing Regulation (EU) No. 1278/2011 of the Commission of December 8, 2011 for the approval of the active ingredient Bitertanol according to Regulation (EC) No. 1107/2009 ... (PDF) .

[PSM-9] General Directorate Health and Food Safety of the European Commission: Entry on Bitertanol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 22, 2016.