Fluensulfone

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Structural formula
Structural formula of fluensulfone
General
Surname Fluensulfone
other names

5-chloro-2- (3,4,4-trifluorobut-3-en-1-ylsulfonyl) -1,3-thiazole

Molecular formula C 7 H 5 ClF 3 NO 2 S 2
Brief description

white, crystalline solid

External identifiers / databases
CAS number 318290-98-1
PubChem 11534927
ChemSpider 9709710
Wikidata Q27225210
properties
Molar mass 291.70 g mol −1
Physical state

firmly

Melting point

34.8  ° C

boiling point

decomposes at 215 ° C

Vapor pressure

3.0 · 10 −2  Pa (25 ° C)

solubility

very sparingly soluble in water (0.545 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-317-319
P: 280-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fluensulfone is a synthetic nematicide . It was first described by Nihon Bayer in Japan in 2001 and launched on the market in 2014.

presentation

4-Bromo-1,1,2-trifluorobut-1-ene is reacted with 2-mercaptothiazole to give the thiazolyl-trifluorobutene-sulfanyl intermediate, which is then regioselectively chlorinated on the thiazole ring with the aid of N-chlorosuccinimide . The product is then oxidized to fluensulfone with potassium peroxomonosulfate .

properties

Fluensulfone is a white, finely crystalline solid with a characteristic odor. The melting point is 34.8 ° C and with further heating it decomposes before it melts. In the soil, it degrades relatively quickly with a half-life of 11–22 days, so the risk of it getting into the groundwater is low. Fluensulfone is stable to hydrolysis, but degrades quickly in light with a half-life of one day.

Mode of action

Fluensulfone is a systemic nematicide and a fast-acting contact poison. Studies with the roundworm Caenorhabditis elegans have shown that it affects the development of larvae (including by stopping feeding), the laying of the eggs, the hatching of the larvae and the locomotion of the nematodes. In addition, it has been shown that the effect is not based on the acetylcholinesterase disruption, as is the case with other nematicides such as Aldicarb , but that a new, as yet unknown mechanism of action is present. According to one hypothesis, the effect could be caused by influencing the enzyme acyl-CoA dehydrogenase, which is important for the lipid metabolism of the nematodes. In insects, it was found that difluoroalkenyl derivatives impair the β-oxidation of fatty acids in the mitochondria.

use

Fluensulfone is used to treat the soil before planting in both arable farming and greenhouses. It is mainly used against root nematodes. The plants for which it is used include fruit-bearing vegetables ( tomatoes , okra , eggplant ), cucurbits , cabbage and leafy vegetables, and low-growing berries (including strawberries). It is commercially available as an emulsifiable concentrate that can either be sprayed or placed in the soil drop by drop.

toxicology

Fluensulfone can irritate the skin and eyes and has a skin sensitizing effect . No neurotoxic or genotoxic effects were found in animal experiments . The WHO gives an ADI of 0.01 mg / kg body weight per day and an acute reference dose of 0.3 mg / kg body weight per day.

Fluensulfone is less toxic to non-target organisms than other nematicides. For example, it is only slightly toxic to bees and bumblebees. In addition, it is not very persistent in the soil, so that fluensulfone has relatively little negative impact on the environment with regard to common nematicides such as aldicarb.

Analytics

Fluensulfone can be reliably detected and quantified using gas chromatographic methods. A mass spectrometer can also be used as a detector for better identification .

Admission

In the European Union and Switzerland , no plant protection products with the active ingredient fluensulfone are permitted. It has been used in the United States since 2016. In the trade there it is, among other things, in the plant protection product Nimitz from the company Adama .

Individual evidence

  1. ↑ a b c d e f Peter Jeschke, Matthias Witschel, Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2019, ISBN 978-3-527-34089-7 ( limited preview in Google Book Search [accessed April 30, 2019]).
  2. ↑ a b c d e f g h Entry on fluensulfone in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on April 26, 2019.
  3. ↑ a b Fluensulfone safety data sheet. (PDF) In: HPC Standards GmbH. April 9, 2019, accessed April 30, 2019 .
  4. ↑ a b James Kearn, Elizabeth Ludlow, James Dillon, Vincent O'Connor, Lindy Holden-Dye: Fluensulfone is a nematicide with a mode of action distinct from anticholinesterases and macrocyclic lactones . In: Pesticide Biochemistry and Physiology . tape 109 , February 2014, p. 44–57 , doi : 10.1016 / j.pestbp.2014.01.004 ( online [accessed April 30, 2019]).
  5. ↑ a b N. G. Ravichandra: Agrochemicals in Plant Disease Management . Scientific Publishers, 2018, ISBN 978-93-8799191-0 ( limited preview in Google Book Search).
  6. ↑ EPA label - Nimitz. (PDF) Adama, accessed on July 31, 2019 .
  7. ↑ Ian Dewhurst, Maria Tasheva: Fluensulfone. (PDF) World Health Organization, 2013, accessed July 31, 2019 .
  8. ↑ Susan Strange Herrmann, Mette Erecius Poulsen: Validation Report 23 B - Determination of pesticide residues in wheat, rye, oat and rice. (PDF) In: eurl-pesticides.com. EURL for Cereals and Feeding stuff, January 2018, accessed July 30, 2019 .
  9. ^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on July 30, 2019.