Oxadiargyl

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Structural formula
Structural formula of oxadiargyl
General
Surname Oxadiargyl
other names
  • 3- (2,4-dichloro-5- (2-propinyloxy) phenyl) -5- (1,1-dimethyl-ethyl) -1,3,4-oxadiazol-2 (3H) -one
  • 5- tert -Butyl-3- (2,4-dichloro-5- (prop-2-ynyloxy) phenyl) -1,3,4-oxadiazol-2 (3 H ) -one
Molecular formula C 15 H 14 Cl 2 N 2 O 3
Brief description

white to yellowish odorless solid

External identifiers / databases
CAS number 39807-15-3
EC number 254-637-6
ECHA InfoCard 100,049,652
PubChem 94498
ChemSpider 85276
Wikidata Q1640254
properties
Molar mass 341.19 g mol −1
Physical state

firmly

density

1.41 g cm −3 (bulk density)

Melting point

131 ° C

Vapor pressure

2.5 × 10 −6 Pa (25 ° C)

solubility
  • practically insoluble in water (0.37 mg l −1 at 20 ° C)
  • soluble in acetone, ethyl acetate and toluene
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
08 - Dangerous to health 09 - Dangerous for the environment

Caution

H and P phrases H: 361d-373-410
P: 201-273-308 + 313-391-501
Toxicological data

> 802 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 .

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

Extraction and presentation

Oxadiargyl can be obtained by phosphorylation of N -aryl- N '-pivaloylhydrazine. The latter itself is obtained by reacting aryl hydrazine with pivaloyl chloride.

properties

Oxadiargyl is a white to yellowish solid. It decomposes when heated before it reaches the boiling point.

use

Oxadiargyl is used as an active ingredient in plant protection products. It serves as a herbicide and was first approved in South America in 1996. It is mainly used in rice and sunflowers and works by inhibiting protoporphyrinogen oxidase (PPO).

Admission

Oxadiargyl was added to the list of approved active ingredients by the European Union in 2003, but approval expired on March 31, 2014. In Germany, Austria and Switzerland no pesticide products with Oxadiargyl are permitted.

Individual evidence

  1. ↑ a b c d e f g h Entry on Oxadiargyl in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.
  2. ↑ a b c Entry on Oxadiargyl in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  3. ↑ EU: Review report for the active substance oxadiargyl (PDF; 266 kB).
  4. ↑ Entry on 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (1,1-dimethylethyl) -1,3,4-oxadiazol-2 (3H) -one Template: Linktext-Check / Escaped 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. ↑ Oxadiargyl data sheet from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
  6. ↑ Peter Böger, Ko Wakabayashi: Peroxidizing Herbicides . Springer, 1999, ISBN 978-3-540-64550-4 , pp. 42 (English, limited preview in Google Book search).
  7. ↑ BAYER: oxadiargyl
  8. ↑ Commission Directive 2003/23 / EC of March 25, 2003 amending Council Directive 91/414 / EEC to include the active substances imazamox, oxasulfuron, ethoxysulfuron, foramsulfuron, oxadiargyl and cyazofamid
  9. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Oxadiargyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 7, 2019.