Benazolin is a herbicide from the group of thiazolinones (thiazolinketones) and benzene compounds. A colorless, crystalline substance.
| Benazolin | |
|---|---|
 | |
| Are common | |
| Systematic name | 2- (4-Chloro-2-oxo-1,3-benzothiazol-3-yl) acetic acid |
| Chem. formula | C 9 H 6 ClNO 3 S |
| Physical properties | |
| condition | colorless solid |
| Molar mass | 243.67 g / mol |
| Thermal properties | |
| T. melt. | 193 ° C |
| Chemical properties | |
| pK a | 3.04 [1] |
| Classification | |
| Reg. CAS number | |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
| Security | |
| LD 50 |
|
| R phrases | R36 / 38 R52 / 53 |
| S-phrases | S22 S61 |
| H phrases | H315 , H319 , H412 |
| P-phrases | P273 , P305 + 351 + 338 |
| GHS icons |  |
Synthesis
Benazolin can be obtained by sequential reactions of 2-chloroaniline with ammonium thiocyanate and ethyl chloroacetic acid [4] .
Features
Benazolin is a flammable, colorless solid that is practically insoluble in water [5] . Solubility in water at 20 ° C and pH 3 is only 500 mg / l [6] . The pK a value of the carboxyl group, depending on the source, is 3.04 [1] or 3.6 [7] .
Usage
Benazolin is a herbicide that can accumulate in soils like a xenobiotic [8] . The mechanism of action is based on the inhibition of auxin transport [9] . A similar effect is exerted by its potassium salts, as well as compounds of the same series, such as benazolin-dimethyl ammonium and benazolinethyl.
Approval
Benazolin was not listed in the European Union for Acceptable Plant Protection 2002 active ingredients. In the EU and in Switzerland, this substance is prohibited for use [10] .
Notes
- ↑ 1 2 Eintrag zu Benazolin in der ChemIDplus -Datenbank der United States National Library of Medicine (NLM)
- ↑ WT Thomson: Agricultural Chemicals , Fresno (CA), Thomson Publications, Vol. 2, S. 26, 1977.
- ↑ Pesticide Manual. Vol. 9, S. 52, 1991.
- ↑ Thomas A. Unger. Pesticide synthesis handbook . - 1996. - P. 419. - ISBN 978-0815514015 .
- ↑ Record of CAS RN 3813-05-6 in the GESTIS Substance Database of the IFA .
- ↑ Eintrag zu Benazolin (German) . In: Römpp Online . Georg Thieme Verlag, abgerufen am 2. Juli 2012.
- ↑ 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 .
- ↑ Schnitzler, F .; Kasteel, R .; Vanderborght, J .; Vereecken, H .: Visualization of the flow pathways of Benazolin and Benzo [a] pyrene in soil monoliths . Eurosoil 2004: Abstractband. - oZ
- ↑ Benazolin in the Pesticide Properties DataBase (PPDB)
- ↑ Generaldirektion Gesundheit und Lebensmittelsicherheit der Europäischen Kommission: Eintrag zu Benazolin in der EU-Pestiziddatenbank; Eintrag in den nationalen Pflanzenschutzmittelverzeichnissen der Schweiz , Österreichs und Deutschlands ; abgerufen am 26. März 2016.