Hexythiazox

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Structural formula
Structural formula of hexythiazox
Structural formula without stereochemistry
General
Surname Hexythiazox
other names
  • trans -5- (4-chlorophenyl) - N -cyclohexyl-4-methyl-2-oxo-3-thiazolidine-carboxamide
  • (4 RS , 5 RS ) -5- (4-chlorophenyl) - N -cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide ( IUPAC )
Molecular formula C 17 H 21 ClN 2 O 2 S
Brief description

white solid

External identifiers / databases
CAS number 78587-05-0
EC number 616-638-3
ECHA InfoCard 100.124.859
PubChem 13218777
Wikidata Q2718012
properties
Molar mass 352.88 g mol −1
Physical state

firmly

density

1.31 g cm −3 (bulk density)

Melting point

106-109 ° C

solubility
  • practically insoluble in water (0.1 mg l −1 at 20 ° C)
  • soluble in acetone, methanol and ethanol
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
09 - Dangerous for the environment

Caution

H and P phrases H: 410
P: 273-501
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexythiazox is a mixture of four stereoisomeric chemical compounds from the group of thiazolidines and carboxamides .

Extraction and presentation

Hexythiazox can be obtained by reacting 2-amino-1-mercapto-1- (4-chlorophenyl) propane with phosgene and then reacting the trans -4-methyl-5- (4-chlorophenyl) -2-thiazolidinone thus formed with cyclohexyl isocyanate become.

Hexythiazox synthesis.svg

properties

Hexythiazox is a white solid that is practically insoluble in water. It decomposes from a temperature of 300 ° C.

use

Hexythiazox is used as an acaricide in a number of fruits, vines, hops and ornamental plants such as lemons and oranges. It was first approved in the USA in 1989. It has been approved in the Federal Republic of Germany since 1990; in the GDR it was approved between 1988 and 1994. It is effective against eggs, larvae and nymphs , but not against adult animals, whereby the long duration of action of the compound is noticeable. Hexythiazox must not be used as a substitute for clofentezine as there is cross resistance .

Admission

Since June 2011, the use of hexythiazox as an acaricidal active ingredient in plant protection products has been approved in the European Union. In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved.

Web links

Individual evidence

  1. a b c d e Entry on Hexythiazox in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
  2. a b c data sheet Hexythiazox, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
  3. a b c Entry on Hexythiazox in the GESTIS substance database of the IFA , accessed on January 2, 2013(JavaScript required) .
  4. Entry on hexythiazox (ISO) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 631 ( limited preview in Google Book search).
  6. EPA: Factsheet Hexythiazox ( Memento of April 12, 2013 in the Internet Archive ).
  7. Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ... Springer DE, 2010, ISBN 3-0348-0028-2 , p. 18 ( limited preview in Google Book search).
  8. ^ Horst Börner: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49067-1 , pp. 592 ( limited preview in Google Book search).
  9. Implementing Directive 2011/46 / EU of the Council of April 14, 2011 amending Council Directive 91/414 / EEC to include the active ingredient Hexythiazox and amending Commission Decision 2008/934 / EC (PDF) .
  10. General Directorate Health and Food Safety of the European Commission: Entry on Hexythiazox in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.