Cinmethyline

Structural formula
	1: 1 mixture of the (1 S , 2 R , 4 R ) form (top) and the (1 R , 2 S , 4 S ) form (bottom)
General
Surname	Cinmethyline
other names	exo - (±) -1-methyl-2- (2-methylbenzyloxy) -4-isopropyl-7-oxa-bicyclo [2.2.1] heptane; (1 R , 2 S , 4 S ) - rel -1-methyl-2 - [(2-methylphenyl) methoxy] -4-propan-2-yl-7-oxabicyclo [2.2.1] heptane; (1 R * , 2 S * , 4 S * ) - (±) -1-methyl-2 - [(2-methylphenyl) methoxy] -4-propan-2-yl-7-oxabicyclo [2.2.1] heptane; (1 RS , 2 SR , 4 SR ) -1-methyl-2 - [(2-methylphenyl) methoxy] -4-propan-2-yl-7-oxabicyclo [2.2.1] heptane;
Molecular formula	C 18 H 26 O 2
Brief description	colorless liquid, the technical product is amber in color
External identifiers / databases
EC number	402-410-9
ECHA InfoCard	100.100.423
PubChem	91745
Wikidata	Q14625376
properties
Molar mass	274.398 g mol −1
Physical state	liquid
density	1.015 g cm −3
boiling point	313 ° C
solubility	practically insoluble in water (0.063 g l −1 at 20 ° C); soluble in organic solvents;
safety instructions
H and P phrases	H: 332-411
	P: 273
Toxicological data	4550 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cinmethylin is a chemical compound that has been used as a pre-emergence herbicide . It is a derivative of the natural terpene 1,4-cineole . Cinmethylin works by inhibiting tyrosine aminotransferase (TAT) in the tyrosine metabolism , which is required for the synthesis of plastoquinones and tocopherols . Cinmethylin is used as a racemate . It was introduced by Shell in 1989.

Extraction and presentation

Cinmethylin can be obtained by a multistage reaction starting from α-terpinene with tert-butyl hydroperoxide and 2-methylbenzyl chloride.

Admission

The active ingredient cinmethylin is not on the list of active ingredients of plant protection products permitted in the EU. In Switzerland, Austria and Germany, no pesticides are permitted that contain cinmethylin as an active ingredient.

Individual evidence

↑ ^a ^b ^c ^d ^e Grayson, Williams, Freehauf, Pease, Ziesel, Sereno, Reinsfelder: The physical and chemical properties of the herbicide cinmethylin (SD 95481) . In: Pesticide Science . tape 21 , no. 2 , 1987, pp. 143-153 , doi : 10.1002 / ps.2780210207 ( libgen.io ).
↑ ^a ^b entry on cinmethylin. In: Römpp Online . Georg Thieme Verlag, accessed on August 29, 2013.
↑ ^a ^b ^c ^d Entry on exo- (±) -1-methyl-2- (2-methylbenzyloxy) -4-isopropyl-7-oxa-bicyclo (2.2.1) heptane in the GESTIS substance database of the IFA , accessed on February 6, 2017(JavaScript required) .
↑ Entry on Cinmethylin (ISO) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 12, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Klaus Grossmann, Johannes Hutzler, Stefan Tresch, Nicole Christiansen, Ralf Looser, Thomas Ehrhardt: On the mode of action of the herbicides cinmethylin and 5-benzyloxymethyl-1,2-isoxazolines: putative inhibitors of plant tyrosine aminotransferase . In: Pest Management Science . tape 68 , no. 3 , 2011, p. 482-492 , doi : 10.1002 / ps.2319 .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 997 ( limited preview in Google Book Search).
^ 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 ; Retrieved February 19, 2016.

[prop-1] Grayson, Williams, Freehauf, Pease, Ziesel, Sereno, Reinsfelder: The physical and chemical properties of the herbicide cinmethylin (SD 95481) . In: Pesticide Science . tape 21 , no. 2 , 1987, pp. 143-153 , doi : 10.1002 / ps.2780210207 ( libgen.io ).

[Römpp-2] try on cinmethylin. In: Römpp Online . Georg Thieme Verlag, accessed on August 29, 2013.

[GESTIS-3] Entry on exo- (±) -1-methyl-2- (2-methylbenzyloxy) -4-isopropyl-7-oxa-bicyclo (2.2.1) heptane in the GESTIS substance database of the IFA , accessed on February 6, 2017(JavaScript required) .

[CLP_100.100.423-4] Entry on Cinmethylin (ISO) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 12, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[moa-5] Klaus Grossmann, Johannes Hutzler, Stefan Tresch, Nicole Christiansen, Ralf Looser, Thomas Ehrhardt: On the mode of action of the herbicides cinmethylin and 5-benzyloxymethyl-1,2-isoxazolines: putative inhibitors of plant tyrosine aminotransferase . In: Pest Management Science . tape 68 , no. 3 , 2011, p. 482-492 , doi : 10.1002 / ps.2319 .

[unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 997 ( limited preview in Google Book Search).

[PSM-7] 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 ; Retrieved February 19, 2016.