Oxadiazon

Structural formula
General
Surname	Oxadiazon
other names	3- (2,4-dichloro-5- (1-methylethoxy) phenyl) -5- (1,1-dimethylethyl) -1,3,4-oxadiazol-2 (3 H ) -one 5- tert -Butyl-3- (2,4-dichloro-5-isopropoxyphenyl) -1,3,4-oxadiazol-2 (3 H ) -one
Molecular formula	C 15 H 18 Cl 2 N 2 O 3
Brief description	white odorless solid
External identifiers / databases
CAS number 19666-30-9 EC number 243-215-7 ECHA InfoCard 100.039.272 PubChem 29732 ChemSpider 27628 Wikidata Q1691365
properties
Molar mass	345.21 g mol −1
Physical state	firmly
density	1.26 g cm −3
Melting point	90 ° C
solubility	practically insoluble in water (1.0 mg l −1 at 20 ° C) soluble in methanol, ethanol, cyclohexane, acetone, isophorone, methyl ethyl ketone, toluene, benzene, chloroform
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 410 P: 273-501
Toxicological data	3500 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

Extraction and presentation

Oxadiazon can be obtained by reacting 1,2,4,5- tetrachlorobenzene with isopropanol , hydrazine , pivaloyl chloride and phosgene .

Alternatively, it can be obtained by reacting 2,4-dichloro-5-isopropoxyphenylhydrazine with trimethylacetyl chloride and then reacting with phosgene.

properties

Oxadiazon is a solid that is practically insoluble in water.

use

Oxadiazon is used as a pre- and post-emergence herbicide. It is mainly used for cotton, rice, soy and sunflowers and works by inhibiting protoporphyrinogen oxidase (PPO).

Admission

Oxadiazon is a plant protection active ingredient approved in the European Union with certain conditions . In Switzerland, Germany and Austria, however, no pesticide products with this active ingredient are approved, but in Portugal. In addition, the active ingredient manufactured by Bayer is also sold on the Brazilian and South African markets. It was approved in the United States in 1978.

literature

• Conclusion on the peer review of the pesticide risk assessment of the active substance oxadiazon . In: EFSA (Ed.): EFSA Journal . tape 8 , no. 2 , 2010, 1389, doi : 10.2903 / j.efsa.2010.1389 (free full text).

Individual evidence

1. ↑ ^{a b c d e f g} Entry for CAS no. 19666-30-9 in the GESTIS substance database of the IFA , accessed on June 8, 2012(JavaScript required) .
2. ↑ ^{a b c d} Entry on Oxadiazon in the Hazardous Substances Data Bank , accessed July 29, 2012.
3. ↑ Entry on 3-2,4-dichloro-5- (1-methylethoxy) phenyl-5- (1,1-dimethylethyl) -1,3,4-oxadiazol-2 (3H) -one in the Classification and Labeling Inventory of European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
4. ↑ Oxadiazon data sheet at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
5. ↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 482 ( limited preview in Google Book search).
6. ↑ Entry on Oxadiazon in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on November 3, 2017.
7. ↑ Directive 2010/39 / EU of the Commission of June 22, 2010 amending Annex I of Directive 91/414 / EEC of the Council with regard to special provisions for the active substances clofentezine, diflubenzuron, lenacil, oxadiazon, picloram and pyriproxyfen (PDF)
8. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Oxadiazon in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.
9. Jump up ↑ Benjamin Luig, Fran Paula de Castro and Alan Tygel (both Campanha Permanente Contra os Agrotóxicos e Pela Vida), Lena Luig (INKOTA network), Simphiwe Dada (Khanyisa), Sarah Schneider (MISEREOR) and Jan Urhahn (Rosa-Luxemburg- Foundation): Dangerous pesticides. (PDF; 2.4 MB) from Bayer and BASF - a global business with double standards. Rosa Luxemburg Foundation , INKOTA network , Episcopal Aid Organization Misereor u. a., April 2020, accessed on April 25, 2020 . 
10. ↑ EPA: Oxadiazon RED Fact Sheet , June 20, 2008, accessed May 20, 2017.