Diacetone ketogulonic acid

Structural formula
General
Surname	Diacetone ketogulonic acid
other names	Dikegulac DAG Diisopropylidene-2-keto- L- gulonic acid
Molecular formula	C 12 H 18 O 7
Brief description	white solid
External identifiers / databases
CAS number 18467-77-1 (free acid) 68539-16-2 (monohydrate) 52508-35-7 ( sodium salt ) EC number 242-348-8 ECHA InfoCard 100,038,484 PubChem 65420 ChemSpider 58884 Wikidata Q3027939
properties
Molar mass	274.2671 g mol −1
Physical state	firmly
density	1.319 g cm −3 (monohydrate)
Melting point	100–101 ° C (monohydrate) > 300 ° C (sodium salt)
solubility	soluble in water (monohydrate)
safety instructions
GHS labeling of hazardous substances Sodium salt Caution H and P phrases H: 312 + 332-412 P: 261-280-304 + 340-312-321-501
Toxicological data	31 g kg −1 ( LD 50 , male rat ,  oral , sodium salt)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diacetone ketogulonic acid is used as a growth regulator, it falls u. a. in the production of ascorbic acid .

synthesis

Dikegulac is made from 2-keto- L- gulonic acid and 2,2-dimethoxypropane .

use

Dikegulac is used as a growth regulator under the trade name Atrinal . It inhibits the growth of many plants, including grasses. In pot azaleas , fuchsias and verbenas and many other plants, the active ingredient inhibits the growth of the main axis and is therefore used to achieve a bushier growth.

Admission

The EU Commission decided in 2002 not to include Dikegulac in the list of active ingredients included in Annex I of Directive 91/414 / EEC, so that its use in plant protection products is not permitted in the EU. In Germany it was allowed to be used in ornamental plants under glass until mid-2007.

No pesticides containing this active ingredient are permitted in Switzerland, Germany or Austria. In the USA, plant protection products with dikegulac are approved.

Ginkgo Gate

In 2008, the Washington, DC Forestry Department first used dikegulac on a large scale in place of the previously used chlorpropham to prevent fruit formation on the city's numerous ginkgo trees . However, this did not show the desired effect, probably due to the unsuitable application period, which is why in autumn 2008 a large number of fruits containing butter and caproic acid ripened and caused an unpleasant odor. The incident was dubbed the "Ginkgo Gate" by the local media.

Individual evidence

1. ↑ ^{a b} Patent US6239293 : Process for producing dikegulac, its salts and derivatives. Filed February 23, 2000 , published May 29, 2001 , applicant: Ptrl East, Inc., inventors: Lowell J. Lawrence, Stefan Kwiatkowski, Steven G. Mobley. ‌
2. ↑ ^{a b} S. Takagi, GA Jeffrey: 2,3: 4,6-Di-O-isopropylidene-2-keto-L-gulonic acid monohydrate . In: Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry . tape 34 , no. 9 , p. 2932-2934 , doi : 10.1107 / S0567740878009693 .
3. ^ ^{A b c} Wilhelm Rademacher, Lutz Brahm: Plant Growth Regulators . In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley-VCH Verlag GmbH & Co. KGaA, 2010, ISBN 978-3-527-30673-2 , doi : 10.1002 / 14356007.a20_415.pub2 .
4. ↑ Safety data sheet Augeo (PDF; 187 kB) from OHP, accessed on February 7, 2020.
5. ↑ Data sheet (-) - 2,3: 4,6-Di-O-isopropylidene-2-keto-L-gulonic acid Monohydrate from Sigma-Aldrich , accessed on June 7, 2019 ( PDF ).
6. ↑ ^{a b} LGC Standards: Dikegulac sodium , accessed April 19, 2020
7. ↑ hlug.de: Derivation of a provisional insignificance threshold for diacetone ketogulonic acid (DAG, Dikegulac) and diacetone-L-sorbose (DAS) (PDF; 467 kB), April 20, 2012.
8. ↑ Atrinal can still be used for azaleas. Retrieved June 7, 2019 . 
9. ↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002 to extend the deadline according to Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this Directive and the revocation of the approval of plant protection products with these active substances.
10. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Dikegulac in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 22, 2016.
11. ↑ United States Environmental Protection Agency (Ed.): Reregristration Eligibility Decision For Dikegulac Sodium . March 2007 ( epa.gov [PDF; accessed on August 29, 2013]).
12. ↑ Carmen Drahl: Ginkgogate: The Stench Of Scandal . In: Chemical & Engineering News . tape 87 , no. 50 , 2009, p. 48 , doi : 10.1021 / cen-v087n050.p048 ( acs.org ).