Benoxacor

Structural formula
	Structural formula without stereochemistry
General
Surname	Benoxacor
other names	( RS ) -4-dichloroacetyl-3,4-dihydro-3-methyl-2 H -1,4-benzoxazine
Molecular formula	C 11 H 11 Cl 2 NO 2
External identifiers / databases
EC number	619-372-6
ECHA InfoCard	100.112.236
PubChem	62306
Wikidata	Q2929874
properties
Molar mass	260.12 g mol −1
Physical state	firmly
density	1.52 g cm −3
Melting point	107.6 ° C
Vapor pressure	0.59 mPa (25 ° C)
solubility	practically insoluble in water (20 mg l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 332
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Benoxacor is a 1: 1 mixture of two enantiomeric chemical compounds from the class of benzoxazines , which is used as herbicide safeners . It is applied together with the maize herbicide metolachlor (trade name Dual ) and protects the plant from damage by the herbicide. Benoxacor protects an increase of at least three Glutathione S-transferase - isoenzymes , so that the herbicide is metabolized faster.

Extraction and presentation

Benoxacor can be obtained by reacting 2,3-dihydro-3-methylbenzoxazine and dichloroacetyl chloride.

Stereochemistry

Generally speaking, chemical compounds with at least one stereocenter form up to 2 ⁿ stereoisomers . Here n is the number of stereocenters. Accordingly, there are two stereoisomers at Benoxacor, which have also been confirmed experimentally:

Enantiomers of benoxacor
( S ) -enantiomer	( R ) -enantiomer

Admission

In the EU, plant protection products containing this substance are approved as safeners.

Individual evidence

↑ ^a ^b ^c ^d Entry on Benoxacor in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on March 22, 2014.
↑ ^a ^b Datasheet Benoxacor, PESTANAL at Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
^ E. Patrick Fuerst, Gerard P. Irzyk, Keith D. Miller, Janis E. McFarland, Charlotte V. Eberlein: Mechanism of action of the herbicide safener benoxacor in maize . In: Pesticide Science . tape 43 , no. 3 , March 1995, p. 242-244 , doi : 10.1002 / ps.2780430311 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 427 ( limited preview in Google Book search).
↑ Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.
↑ 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 / 978-1-4014-2329-4_1 , see p. 20.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Benoxacor in the EU pesticide database ; accessed on February 23, 2016.

[ppdb-1] Entry on Benoxacor in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on March 22, 2014.

[Sigma-2] Datasheet Benoxacor, PESTANAL at Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).

[3] E. Patrick Fuerst, Gerard P. Irzyk, Keith D. Miller, Janis E. McFarland, Charlotte V. Eberlein: Mechanism of action of the herbicide safener benoxacor in maize . In: Pesticide Science . tape 43 , no. 3 , March 1995, p. 242-244 , doi : 10.1002 / ps.2780430311 ( PDF ).

[unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 427 ( limited preview in Google Book search).

[5] Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.

[Ulrich-6] 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 / 978-1-4014-2329-4_1 , see p. 20.

[7] General Directorate Health and Food Safety of the European Commission: Entry on Benoxacor in the EU pesticide database ; accessed on February 23, 2016.