Fluorochloridone

Structural formula
Structural formula without stereochemistry
General
Surname	Fluorochloridone
other names	3-chloro-4-chloromethyl-1- [3- (trifluoromethyl) phenyl] pyrrolidin-2-one Flurch chloride Racer
Molecular formula	C 12 H 10 Cl 2 F 3 NO
Brief description	beige crystalline substance in technical quality: waxy substance
External identifiers / databases
CAS number 61213-25-0 (complex mixture of stereoisomers) 61213-60-3 (racemic trans diastereomer) 61213-59-0 (racemic cis diastereomer) EC number 262-661-3 ECHA InfoCard 100.056.947 PubChem 91677 Wikidata Q18624139
properties
Molar mass	312.12 g mol −1
Physical state	firmly
Melting point	cis isomer 55-57 ° C trans isomer 81-83 ° C
solubility	practically insoluble in water (40 mg l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 302-317-360FD-410 P: 261-280-301 + 312-321-405-501
Toxicological data	3650 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 .

Flurochloridone is a chemical compound from the pyrrolidinone group that is used as an active ingredient in pesticides .

Stereochemistry

Generally speaking, chemical compounds with multiple stereocenters form up to 2 ⁿ stereoisomers . Here n is the number of stereocenters. According to this, there are four stereoisomers of flurochloridone, which have also been confirmed experimentally. It is a mixture of (3 S , 4 S ) -, (3 R , 4 R ) -, (3 S , 4 R ) - and the (3 R , 4 S ) form:

Four stereoisomers (two pairs of diastereomers)
trans diastereomer = 1: 1 mixture ( racemate ) CAS number: 61213-60-3
cis -diastereomer = 1: 1 mixture (racemate) CAS number: 61213-59-0

In the commercially available fluorochloridone, the mass fraction of the trans diastereomer is 72% to 74%. The mass fraction of the cis diastereomer is between 22% and 24%.

Extraction and presentation

Flurochloridone can be obtained from 3-aminobenzotrifluoride and acetic anhydride . Their product reacts with allyl bromide , hydrogen chloride and dichloroacetyl chloride . The end product is formed by ring closure in the presence of iron (II) chloride .

use

Flurochloridone was introduced by ICI (now Syngenta ) in the mid-1980s as a selective herbicide . It is one of the phytoene desaturase inhibitors (PDS inhibitors) that intervene in carotenoid biosynthesis.

Flurochloridone is used against broad-leaved weeds and some grass weeds in cereal, potato, sunflower and cotton cultivation.

Admission

In Switzerland and some EU countries such as Austria, plant protection products with this active ingredient are permitted, but not in Germany.

Individual evidence

1. ↑ ^{a b c d e f g} Entry on fluorochloridone. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.
2. ↑ ^{a b} Safety data sheet for flurochloridone. (PDF) In: LGC Standards. April 3, 2019, accessed August 11, 2020 . 
3. ↑ Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.
4. ↑ Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4614-2329-4_1 , see p. 24.
5. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Flurochloridone in the EU pesticide database; accessed on February 2, 2018.
6. ↑ ^{a b} Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 580 ( limited preview in Google Book search).
7. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Flurochloridone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.