Endothal

Structural formula
General
Surname	Endothal
other names	7-oxabicyclo [2.2.1] heptane-2,3-dicarboxylic acid ( IUPAC ) ; 3,6-epoxycyclohexane-1,2-dicarboxylic acid; Endothall;
Molecular formula	C 8 H 10 O 5
Brief description	white odorless crystals
External identifiers / databases
EC number	205-660-5
ECHA InfoCard	100.005.146
PubChem	3225
ChemSpider	3112
Wikidata	Q3054030
properties
Molar mass	186.16 g mol −1
Physical state	firmly
density	1.431 g cm −3 (20 ° C)
Melting point	144 ° C (monohydrate)
boiling point	decomposes
Vapor pressure	2.09 · 10 −8 Pa (25 ° C)
solubility	Easily soluble in water (100 g l −1 at 20 ° C) and methanol (280 g l −1 at 20 ° C); soluble in acetone (70 g l −1 at 20 ° C) and dioxane (60 g l −1 at 20 ° C); poorly soluble in benzene (0.1 g l −1 at 20 ° C);
safety instructions
H and P phrases	H: 300-312-315-319-335-400
	P: 210-280-301 + 310 + 330-302 + 352 + 312-304 + 340 + 311
Toxicological data	38 mg kg −1 ( LD 50 , rat , oral ) ; > 1000 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 .

Endothal is a chemical compound from the group of dicarboxylic acids that can be used as a herbicide .

Extraction and presentation

The disodium salt of Endothal can be obtained by a Diels-Alder reaction of furan with maleic anhydride and subsequent hydrogenation of the anhydride in sodium hydroxide solution .

The free acid is obtained by neutralization .

use

Endothal can be used as a contact herbicide which is absorbed through the roots and leaves . It is mainly used to control broad-leaved weeds and annual grasses in sugar beets and spinach . In cotton , alfalfa and clover , it is beyond the defoliant used. The effect is based on the inhibition of protein phosphatase 2A in the mitotic signal chain.

Admission

The active ingredient Endothal has not been approved for use in plant protection products in the European Union since 2002 . Endothal was approved as a herbicide in Germany until 1989. No pesticides containing this active ingredient are currently approved in Germany, Austria or Switzerland.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Endothal in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c ^d Entry on Endothal in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on September 2, 2013.
↑ Entry on Endothal in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Endothal -WS data sheet at Sigma-Aldrich , accessed on January 25, 2020 ( PDF ).

↑ ^a ^b Entry on Endothal in the ChemIDplus database of the United States National Library of Medicine (NLM)

↑ Richard Wegler (ed.): Chemistry of pesticides and pesticides . Volume 2. Springer Verlag, Berlin, Heidelberg 1970, ISBN 978-3-662-11798-9 , pp. 284 ( limited preview in Google Book search).

^ Franz Müller, Arnold P. Applebyki: Weed Control, 2. Individual Herbicides . In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley-VCH Verlag GmbH & Co. KGaA, 2010, ISBN 978-3-527-30673-2 , doi : 10.1002 / 14356007.o28_o01 .

↑ Stefan Tresch, Jennifer Schmotz, Klaus Grossmann: Probing mode of action in plant cell cycle by the herbicide endothall, a protein phosphatase inhibitor . In: Pesticide Biochemistry and Physiology . tape 99 , no. 1 , 2011, p. 86-95 , doi : 10.1016 / j.pestbp.2010.11.004 .

↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF) extending 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.

↑ General Directorate Health and Food Safety of the European Commission: Entry on Endothal in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Endothal in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[PPDB-2] Entry on Endothal in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on September 2, 2013.

[CLP_100.005.146-3] Entry on Endothal in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[sigma-4] Endothal -WS data sheet at Sigma-Aldrich , accessed on January 25, 2020 ( PDF ).

[chemid-5] Entry on Endothal in the ChemIDplus database of the United States National Library of Medicine (NLM)

[Weglerr-6] Richard Wegler (ed.): Chemistry of pesticides and pesticides . Volume 2. Springer Verlag, Berlin, Heidelberg 1970, ISBN 978-3-662-11798-9 , pp. 284 ( limited preview in Google Book search).

[ullmann-7] Franz Müller, Arnold P. Applebyki: Weed Control, 2. Individual Herbicides . In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley-VCH Verlag GmbH & Co. KGaA, 2010, ISBN 978-3-527-30673-2 , doi : 10.1002 / 14356007.o28_o01 .

[tresch-8] Stefan Tresch, Jennifer Schmotz, Klaus Grossmann: Probing mode of action in plant cell cycle by the herbicide endothall, a protein phosphatase inhibitor . In: Pesticide Biochemistry and Physiology . tape 99 , no. 1 , 2011, p. 86-95 , doi : 10.1016 / j.pestbp.2010.11.004 .

[9] Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF) extending 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.

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on Endothal in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.