Benazolin

Structural formula
General
Surname	Benazolin
other names	2- (4-chloro-2-oxo-1,3-benzothiazol-3-yl) acetic acid ( IUPAC ); 4-chloro-2-oxobenzothiazolin-3-ylacetic acid; Cornox;
Molecular formula	C 9 H 6 ClNO 3 S
Brief description	colorless solid
External identifiers / databases
EC number	223-297-0
ECHA InfoCard	100.021.180
PubChem	19662
ChemSpider	18521
Wikidata	Q816692
properties
Molar mass	243.67 g mol −1
Physical state	firmly
Melting point	193 ° C
boiling point	decomposes
pK s value	3.04-3.6
solubility	minimally soluble in water (500 mg l −1 at 20 ° C); soluble in acetone, ethanol and ethyl acetate;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 315-319-412
	P: 273-305 + 351 + 338
Toxicological data	3000 mg kg −1 ( LD 50 , rat , oral ) ; 3200 mg kg −1 ( LD 50 , mouse , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Benazolin is a synthetically produced chemical compound from the group of thiazolinones ( thiazolines with a keto group ) or benzothiazolinones . The colorless, crystalline solid is mainly used as a herbicide .

Extraction and presentation

Benazolin can be obtained by reacting 2-chloroaniline with ammonium thiocyanate and ethyl chloroacetate .

properties

Benazolin is a flammable colorless solid that is practically insoluble in water. The solubility in water at 20 ° C and pH 3 is only 500 mg · l ⁻¹ . The pK _S value of the carboxylic acid is - depending on the source - given as 3.04 or 3.6.

use

Benazolin is a herbicide that occurs as a xenobiotic in soil. The effect is based on the inhibition of the auxin transport. It is the starting compound for a number of substances with similar properties, such as its potassium salt (CAS number: 67338-65-2), benazolin-dimethylammonium (38561-76-1) and benazolin-ethyl (25059-800-7).

Admission

In 2002, benazolin was not included in the list of plant protection active ingredients permitted in the European Union . No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Individual evidence

↑ ^a ^b ^c ^d Entry for CAS no. 3813-05-6 in the GESTIS substance database of the IFA , accessed on July 2, 2012(JavaScript required) .
↑ ^a ^b entry on benazolin. In: Römpp Online . Georg Thieme Verlag, accessed on July 2, 2012.
↑ ^a ^b ^c Entry on Benazolin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.
↑ ^a ^b ^c Entry on benazolin in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ ^a ^b Hu, Jian-Ying; Aizawa, Takako; Magara, Yasumoto: Analysis of pesticides in water with liquid chromatography / atmospheric pressure chemical ionization mass spectrometry In: Water Research 33 (1999), 417-425, doi : 10.1016 / S0043-1354 (98) 00235-8 .
↑ Entry on Benazolin 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 .
^ WT Thomson: Agricultural Chemicals , Fresno (CA), Thomson Publications, Vol. 2, p. 26, 1977.
^ Pesticide Manual. Vol. 9, p. 52, 1991.
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 419 ( limited preview in Google Book search).
↑ Schnitzler, F .; Kasteel, R .; Vanderborght, J .; Vereecken, H .: Visualization of the flow pathways of Benazolin and Benzo [a] pyrene in soil monoliths . Eurosoil 2004: abstract volume. - oZ
↑ General Directorate Health and Food Safety of the European Commission: Entry on benazolin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.

[GESTIS-1] Entry for CAS no. 3813-05-6 in the GESTIS substance database of the IFA , accessed on July 2, 2012(JavaScript required) .

[Römpp-2] try on benazolin. In: Römpp Online . Georg Thieme Verlag, accessed on July 2, 2012.

[herts-3] Entry on Benazolin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.

[chemid-4] Entry on benazolin in the ChemIDplus database of the United States National Library of Medicine (NLM)

[hu-5] Hu, Jian-Ying; Aizawa, Takako; Magara, Yasumoto: Analysis of pesticides in water with liquid chromatography / atmospheric pressure chemical ionization mass spectrometry In: Water Research 33 (1999), 417-425, doi : 10.1016 / S0043-1354 (98) 00235-8 .

[CLP_100.021.180-6] Entry on Benazolin 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 .

[7] WT Thomson: Agricultural Chemicals , Fresno (CA), Thomson Publications, Vol. 2, p. 26, 1977.

[8] Pesticide Manual. Vol. 9, p. 52, 1991.

[Unger-9] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 419 ( limited preview in Google Book search).

[Schnitzler_2004-10] Schnitzler, F .; Kasteel, R .; Vanderborght, J .; Vereecken, H .: Visualization of the flow pathways of Benazolin and Benzo [a] pyrene in soil monoliths . Eurosoil 2004: abstract volume. - oZ

[11] General Directorate Health and Food Safety of the European Commission: Entry on benazolin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.