Silafluofen

Structural formula
General
Surname	Silafluofen
other names	Silons; (4-ethoxyphenyl) [3- (4-fluoro-3-phenoxyphenyl) propyl] dimethylsilane; Neophane; joker; Silatop;
Molecular formula	C 25 H 29 FO 2 Si
Brief description	colorless or yellowish oily liquid
External identifiers / databases
EC number	405-020-7
ECHA InfoCard	100.100.662
PubChem	92430
ChemSpider	83448
Wikidata	Q7514043
properties
Molar mass	408.58 g mol −1
Physical state	liquid
density	1.08 g cm −3
boiling point	decomposes
solubility	almost insoluble in water (0.001 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 360F-410
	P: 201-273-308 + 313-501
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Silafluofen is a chemical compound from the group of pyrethroid - ether , which was found in Japan by Yoshio Katsuda from Dainippon 1984th Hoechst received a patent in Germany and FMC in North America . In 1991, silafluofen was first approved in Japan. It is significantly less toxic to fish than the other pyrethroids.

Extraction and presentation

Silafluofen can be represented by a multi-stage reaction. First, 3-chloro-4-fluoronitroaniline and sodium nitrite are reacted, the product of which is then brominated with hydrogen bromide and copper (II) bromide . The product now reacts with the Grignard reagent made from 3-bromopropene . Then 4-ethoxyphenyldimethylsilane is added in the presence of hexachloridoplatinic acid . The intermediate product then reacts with sodium phenolate to form the end product.

use

In Japan, silafluofen has been used as a crop protection agent in various crops since 1995. It is less toxic to fish than other pyrethroids, which is particularly important when growing wet rice . Silafluofen is used as an insecticide and termiticide , especially in wood protection . It is suitable for this because of its stability against degradation in the ground, by sunlight or by bases.

Admission

The active ingredient silafluofen was never approved for use in plant protection products in the EU. In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c ^d Entry on Silafluofen in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on December 17, 2013.
↑ Entry on (4-ethoxyphenyl) (3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ Entry on (4-ethoxyphenyl) (3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and expand labeling .
↑ Silafluofen data sheet , PESTANAL at Sigma-Aldrich , accessed on December 17, 2013 ( PDF ).
↑ ^a ^b ^c ^d Yoshio Katsuda, Yoshihiro Minamite, Charunee Vongkaluang: Development of Silafluofen-Based Termiticides in Japan and Thailand. In: Insects. 2, 2011, pp. 532-539, doi: 10.3390 / insects2040532 .
^ ^A ^b New Applications of Silafluofen to Termite Control .
↑ Patent EP0224024 : New silane derivatives, process for their preparation, agents containing them and their use as pesticides. Applied on October 21, 1986 , published on June 20, 1990 , applicant: Hoechst AG. ‌
↑ Patent US4709068 : Compounds containing a dimethylsilane core and a phenoxybenzyl substitute are found to exhibit pyrethroid-like activity toward insects with low toxicity to fish. Applied June 2, 1986 , published November 24, 1987 , assignee: FMC Corporation. & US4883789 Substituted Phenyltrialkyl silanes Insecticides
↑ ^a ^b Alexander Grube: Total synthesis of new spinosyn analogues . Cuvillier, Göttingen 2007, ISBN 3-86727-439-8 , p. 28 ( limited preview in Google Book search).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 970 ( limited preview in Google Book search).
↑ General Directorate Health and Food Safety of the European Commission: Entry on Silafluofen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.

[PPDB-1] Entry on Silafluofen in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on December 17, 2013.

[GESTIS-2] Entry on (4-ethoxyphenyl) (3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[CLP_100.100.662-3] Entry on (4-ethoxyphenyl) (3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and expand labeling .

[Sigma-4] Silafluofen data sheet , PESTANAL at Sigma-Aldrich , accessed on December 17, 2013 ( PDF ).

[mdpi-5] Yoshio Katsuda, Yoshihiro Minamite, Charunee Vongkaluang: Development of Silafluofen-Based Termiticides in Japan and Thailand. In: Insects. 2, 2011, pp. 532-539, doi: 10.3390 / insects2040532 .

[appl-6] A ^b New Applications of Silafluofen to Termite Control .

[7] Patent EP0224024 : New silane derivatives, process for their preparation, agents containing them and their use as pesticides. Applied on October 21, 1986 , published on June 20, 1990 , applicant: Hoechst AG. ‌

[8] Patent US4709068 : Compounds containing a dimethylsilane core and a phenoxybenzyl substitute are found to exhibit pyrethroid-like activity toward insects with low toxicity to fish. Applied June 2, 1986 , published November 24, 1987 , assignee: FMC Corporation. & US4883789 Substituted Phenyltrialkyl silanes Insecticides

[grube-9] Alexander Grube: Total synthesis of new spinosyn analogues . Cuvillier, Göttingen 2007, ISBN 3-86727-439-8 , p. 28 ( limited preview in Google Book search).

[unger-10] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 970 ( limited preview in Google Book search).

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on Silafluofen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.