Spirodiclofen

Structural formula
General
Surname	Spirodiclofen
other names	3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl-2,2-dimethylbutyrate
Molecular formula	C 21 H 24 Cl 2 O 4
Brief description	white odorless solid
External identifiers / databases
EC number	604-636-5
ECHA InfoCard	100.130.204
PubChem	177863
Wikidata	Q425807
properties
Molar mass	411.32 g mol −1
Physical state	firmly
density	1.29 g cm −3
Melting point	94.8 ° C
Vapor pressure	3 10 −7 Pa (20 ° C)
solubility	almost insoluble in water; soluble in xylene, dichloromethane, acetone, ethyl acetate and acetonitrile;
safety instructions
H and P phrases	H: 317-350-361f-373-410
	P: 261-272-280-302 + 352-333 + 313-362 + 364
Toxicological data	> 2500 mg kg −1 ( LD 50 , rat , oral ) ; > 2500 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Spirodiclofen is a chemical compound from the group of tetronic acid derivatives .

Extraction and presentation

Spirodiclofen can be obtained from ethyl 1-hydroxycyclohexanecarboxylate and 2,4-dichlorophenylacetyl chloride. The former is obtained by reacting cyclohexanone by adding hydrogen cyanide to cyanohydrin, followed by saponification and esterification . The second intermediate product is synthesized from 2,4-dichlorobenzyl chloride by cyanide exchange, saponification and conversion into the acid chloride . Both starting materials are condensed and the tetronic acid derivative obtained is esterified with 2,2-dimethylbutyric acid.

properties

Spirodiclofen is a white, odorless solid that is insoluble in water.

use

Spirodiclofen is used as an acaricide in fruit and viticulture, as well as an insecticide and acaricide (against spider mites and gall mites ). The effect is based on the inhibition of the biosynthesis of lipids .

Admission

In the European Union, at the request of Bayer CropScience , the active ingredient spirodiclofen was approved for use as an insecticide and acaricide with effect from August 1, 2010. In Germany, Austria and Switzerland, plant protection products (e.g. Envidor) with this active ingredient are approved.

safety instructions

At the suggestion of the Dutch chemical authorities, the chemical classification of spirodiclofen was revised in 2016. The Committee for Risk Assessment (RAC) of the European Chemicals Agency (ECHA) decided the classification for spirodiclofen as follows on December 9, 2016: Spirodiclofen is classified as carcinogenic Carc 1B, reproductive toxic Repr 2, skin sensitizing Skin Sens 1B, organotoxic STOT RE2 and ecotoxic Aquatic Chronic 1 classified. The warnings have been set to H317, H350, H361f, H373 and H410. This classification of the RAC has yet to be implemented by the EU Commission into applicable law, but with the publication it represents the state of knowledge that must be taken into account by companies and authorities.

In Switzerland, there is a relatively high maximum residue level of 0.5 milligrams spirodiclofen per kilogram for aubergines and tomatoes .

Web links

Bayer Crop Compendium: spirodiclofen .
EU: Review report for the active substance spirodiclofen (PDF; 158 kB), October 22, 2010.

Individual evidence

↑ ^a ^b ^c ^d ^e EPA: Pesticide Fact Sheet spirodiclofen , 2005.
↑ ^a ^b ^c ^d ^e data sheet Spirodiclofen at Sigma-Aldrich , accessed on December 30, 2019 ( PDF ).
↑ FAO: Spirodiclofen (PDF; 961 kB).
↑ ^a ^b ^c BVL: Spirodiclofen , April 2005.
↑ Entry on spirodiclofen (ISO); 3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl 2,2-dimethylbutyrate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 30, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 1111 (English, limited preview in Google Book search).
↑ Horst Börner, Klaus Schlueter, Jens Aumann: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49067-1 , pp. 588 ( limited preview in Google Book search).
↑ Directive 2010/25 / EU of the Commission of March 18, 2010 amending Council Directive 91/414 / EEC to include the active substances penoxsulam, proquinazid and spirodiclofen
^ Directorate-General for Health and Food Safety of the European Commission: Entry on spirodiclofen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.
^ RAC decision of December 9, 2016
↑ Ordinance of the EDI on the maximum levels for pesticide residues in or on products of plant and animal origin. In: admin.ch . Retrieved February 7, 2020 .

[EPA-1] EPA: Pesticide Fact Sheet spirodiclofen , 2005.

[Sigma-2] ↑ ^a ^b ^c ^d ^e data sheet Spirodiclofen at Sigma-Aldrich , accessed on December 30, 2019 ( PDF ).

[FAO-3] FAO: Spirodiclofen (PDF; 961 kB).

[BVL-4] BVL: Spirodiclofen , April 2005.

[CLP_100.130.204-5] Entry on spirodiclofen (ISO); 3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl 2,2-dimethylbutyrate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 30, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[Wolfgang_Krämer,_Ulrich_Schirmer-6] Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 1111 (English, limited preview in Google Book search).

[Horst_Börner,_Klaus_Schlüter,_Jens_Aumann-7] Horst Börner, Klaus Schlueter, Jens Aumann: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49067-1 , pp. 588 ( limited preview in Google Book search).

[8] Directive 2010/25 / EU of the Commission of March 18, 2010 amending Council Directive 91/414 / EEC to include the active substances penoxsulam, proquinazid and spirodiclofen

[PSM-9] Directorate-General for Health and Food Safety of the European Commission: Entry on spirodiclofen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[10] RAC decision of December 9, 2016

[11] Ordinance of the EDI on the maximum levels for pesticide residues in or on products of plant and animal origin. In: admin.ch . Retrieved February 7, 2020 .