Spiromesifen

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Structural formula
Structure of spiromesifen
General
Surname Spiromesifen
other names
  • 3-Mesityl-2-oxo-1-oxaspiro [4.4] non-3-en-4-yl-3,3-dimethylbutyrate ( IUPAC )
  • Brand names: Oberon®, Forbid®, Judo®
Molecular formula C 23 H 30 O 4
Brief description

light brown solid

External identifiers / databases
CAS number 283594-90-1
EC number 608-196-5
ECHA InfoCard 100.111.418
PubChem 9907412
Wikidata Q1315183
properties
Molar mass 370.48 g mol −1
Physical state

firmly

density

1.13 g cm −3

Melting point

96.7-98.7 ° C

solubility

practically insoluble in water

safety instructions
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 317-332-410
P: 273-280-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Spiromesifen is an insecticide and acaricide from the substance class of the tetronic acid derivatives , which was developed by Bayer CropScience and has been sold by Bayer under the brand name Oberon® since 2006 . It works by inhibiting lipid metabolism and is used in the cultivation of useful and ornamental plants, especially against mites and whiteflies .

application

Spiromesifen is primarily used to control mites and whiteflies , against which it has been shown to be more effective than other insecticides. It is used by spraying suspensions of the substance and can be used on fruit and vegetable plants as well as on other useful plants such as cotton or on ornamental plants . Spiromesifen is approved in El Salvador , Guatemala , Indonesia , Israel , Kenya , Mexico , the Netherlands , Great Britain and the United States, among others . In Germany , Austria and Switzerland there is no approval as a plant protection product, in other EU countries it is approved.

Mechanism of action and toxicity

Spiromesifen works by inhibiting acetyl-CoA carboxylase , an enzyme involved in lipid metabolism , as a result of which the affected insects dry out and die three to ten days after the treatment. Due to the short availability, no resistances are known in the target insects, nor are there any cross-resistances with other available insecticides.

According to the manufacturer, the damage and risks for non-target insects are low. The LD 50 for mammals with oral ingestion and inhalation is more than 2,000 milligrams per kilogram of body weight and when absorbed through the skin more than 4,000 milligrams per kilogram of body weight, so that there is no acute toxicity when used as intended . It is classified as toxic to fish and other aquatic life.

literature

  • T. Bretschneider, R. Fischer, J. Benet-Buchholz: Spiromesifen (Oberon®) - discovery, synthesis and X-ray structure. In: Plant Protection News Bayer. 58 (3 )/2005. Bayer CropScience, ISSN  0340-1723 , pp. 307-318.
  • R. Nauen, H.-J. Schnorbach, A. Elbert: The biological profile of spiromesifen (Oberon®) - A new tetronic acid insecticide / acaricide. In: Plant Protection News Bayer. 58 (3 )/2005. Bayer CropScience, ISSN  0340-1723 , pp. 417-440.
  • R. Nauen, S. Konanz: Spiromesifen as a new chemical option for resistance management in whiteflies and spider mites. In: Plant Protection News Bayer. 58 (3 )/2005. Bayer CropScience, ISSN  0340-1723 , pp. 485-502.

Web links

Individual evidence

  1. a b c data sheet Spiromesifen at Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
  2. a b c T. Bretschneider et al. In: Plant Protection News Bayer. 58 (3 )/2005. Bayer CropScience, ISSN  0340-1723 , pp. 307-318.
  3. R. Nauen et al. T. Bretschneider, A. Elbert, R. Fischer, R. Tiemann: Spirodiclofen and spiromesifen: Tetronic acid derivatives for insect and spider mite control. In: Pesticide Outlook. 12/2003. Royal Society of Chemistry, ISSN  0956-1250 , pp. 243-245.
  4. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on spiromesifen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 16, 2016.
  5. R. Nauen et al. in: Plant Protection News Bayer. 58 (3) / 2005, pp. 417-440 (see literature).
  6. a b Safety data sheet (Bayer CropScience) suspension concentrate , accessed on May 14, 2017.