Hexaconazole

Structural formula
	Structural formula without stereochemistry
General
Surname	Hexaconazole
other names	( RS ) -2- (2,4-dichlorophenyl) -1- (1 H -1,2,4-triazol-1-yl) hexan-2-ol ( IUPAC ) ; Hexaconazole; Anvil;
Molecular formula	C 14 H 17 Cl 2 N 3 O
Brief description	colorless solid
External identifiers / databases
EC number	413-050-7
ECHA InfoCard	100.101.232
PubChem	66461
ChemSpider	59833
Wikidata	Q424794
properties
Molar mass	314.21 g mol −1
Physical state	firmly
density	1.29 g cm −3
Melting point	111 ° C
Vapor pressure	0.02 mPa (20 ° C)
solubility	practically insoluble in water; soluble in many organic solvents;
safety instructions
H and P phrases	H: 302-317-411
	P: 273-280-301 + 312 + 330-302 + 352
Toxicological data	2190 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 .

Hexaconazole is an active ingredient for crop protection and a chemical compound from the group of triazoles .

Extraction and presentation

Hexaconazole can be obtained by a multi-stage reaction from m -dichlorobenzene and 1-chloropentane with trimethylsulfonium iodide , dimethylsulfoxide and the sodium salt of 1,2,4-triazole .

properties

Hexaconazole is a colorless solid that is practically insoluble in water.

use

Hexaconazole is used as a broad-spectrum fungicide against hose and stand fungus in wine (against black rot ), apples (against powdery mildew ), coffee and peanuts. It was launched in 1986 under the names Contaf, Anvil and Planeta. It acts as an inhibitor of steroid demethylation.

Admission

In November 2006 the EU Commission decided that hexaconazole should not be included in Annex I of Directive 91/414 / EEC. It is therefore not allowed to be used as an active ingredient in plant protection products in the EU today.

In the EU states including Germany and Austria as well as in Switzerland no pesticides with this active substance are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on hexaconazole in the GESTIS substance database of the IFA , accessed on January 17, 2020(JavaScript required) .
↑ 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 Ullmann's Agrochemicals . tape 1 . Wiley-VCH, 2007, ISBN 978-3-527-31604-5 ( page 611 in the Google book search).
↑ Entry on (RS) -2- (2,4-dichlorophenyl) -1- (1H-1,2,4-triazol-1-yl) hexan-2-ol 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 .
↑ ^a ^b Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 706 ( preview ).
↑ ^a ^b Timothy C. Marrs, Bryan Ballantyne: Pesticide toxicology and international regulation . John Wiley & Sons, 2003, ISBN 0-471-49644-8 ( page 255 in the Google book search).
↑ Decision 2006/797 / EC of the Commission of November 22, 2006 on the non-intake of ammonium sulfamate, hexaconazole, sodium tetrathiocarbonate and 8-hydroxyquinoline in Annex I of Directive 91/414 / EEC of the Council and the revocation of the approvals for plant protection products with these active substances ( PDF) .
↑ General Directorate Health and Food Safety of the European Commission: Entry on Hexaconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.

[GESTIS-1] Entry on hexaconazole in the GESTIS substance database of the IFA , accessed on January 17, 2020(JavaScript required) .

[UllmannTC-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 .

[ullmann-3] ↑ ^a ^b ^c ^d ^e ^f Ullmann's Agrochemicals . tape 1 . Wiley-VCH, 2007, ISBN 978-3-527-31604-5 ( page 611 in the Google book search).

[CLP_100.101.232-4] Entry on (RS) -2- (2,4-dichlorophenyl) -1- (1H-1,2,4-triazol-1-yl) hexan-2-ol 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 .

[unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 706 ( preview ).

[Marrs-6] Timothy C. Marrs, Bryan Ballantyne: Pesticide toxicology and international regulation . John Wiley & Sons, 2003, ISBN 0-471-49644-8 ( page 255 in the Google book search).

[7] Decision 2006/797 / EC of the Commission of November 22, 2006 on the non-intake of ammonium sulfamate, hexaconazole, sodium tetrathiocarbonate and 8-hydroxyquinoline in Annex I of Directive 91/414 / EEC of the Council and the revocation of the approvals for plant protection products with these active substances ( PDF) .

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on Hexaconazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.