Oxamyl

Structural formula
	Structural formula of the ( Z ) isomer
General
Surname	Oxamyl
other names	Vydate; Thioxamyl; S -Methyl 1- (dimethylcarbamoyl) - N - [(methylcarbamoyl) oxy] thioformamidate; Methyl N ', N ' -dimethyl- N - [(methylcarbamoyl) oxy] -1-thio-oxamidate; N ', N ' -Dimethylcarbamoyl (methylthio) methylenamine- N -methylcarbamate;
Molecular formula	C 7 H 13 N 3 O 3 S
Brief description	colorless solid with a slightly sulphurous odor
External identifiers / databases
EC number	245-445-3
ECHA InfoCard	100.041.299
PubChem	31657
Wikidata	Q409836
properties
Molar mass	219.26 g mol −1
Physical state	firmly
density	0.97 g cm −3
Melting point	109-110 ° C [( Z ) -isomer] ; 101-103 ° C [( E ) -isomer] ;
Vapor pressure	3.059 10 −5 kPa (25 ° C)
solubility	soluble in water (280 g l −1 at 25 ° C), methanol, DMF, acetone, ethanol and cyclohexanone; insoluble in hexane;
safety instructions
H and P phrases	H: 300-312-330-411
	P: 273-280-301 + 310 + 330-302 + 352 + 312-304 + 340 + 310
Toxicological data	2.5 mg kg −1 ( LD 50 , rat , oral ) ; 740 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 .

Oxamyl is an active ingredient for crop protection and a chemical compound from the group of carbamates .

Extraction and presentation

By reacting methyl glyoxalate with hydroxylamine , the corresponding oxime is obtained with elimination of water . This is chlorinated with elemental chlorine on the carbon of the oxime group . The chloride is then reacted with methanethiol , with nucleophilic attack by sulfur, to form the thioether . The corresponding amide is obtained by amidation with dimethylamine . The last step is the reaction with methyl isocyanate , which gives the oxamyl.

In 1982 about 180 tons were produced in the USA.

properties

Oxamyl is a colorless solid with a slightly sulphurous odor. A melting point is 100-102 ° C, with a second polymorphic form recrystallized from the melt, which has a melting point of 108 to 110 ° C. The compound is stable under neutral or acidic conditions.

use

Estimated 2011 US application rate

Oxamyl works by inhibiting cholinesterases and is used as an active ingredient in pesticides. It is used as a systemic insecticide , nematicide and acaricide .

In the USA, Oxamyl is used in cotton, fruit and vegetable growing.

Admission status

Oxamyl may be used as an insecticide and nematicide in the countries of the European Union.

The active ingredient was approved in Germany from 1977 to 1987.

In Germany, Austria and Switzerland, no pesticide products with this active ingredient are currently approved.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on Oxamyl in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c ^d ^e WHO / FAO Data Sheet on Pesticides (PDS) for Oxamyl ( Memento of July 2, 2014 in the Internet Archive ).
↑ ^a ^b Buchanan, JB: Preparation of 1- (Carbamoyl) -n- (carbamoyloxy) thio-formamidates from Alkyl Acetoacetates , Patent US3557190 (Du Pont de Nemours), January 19, 1971.
↑ Entry on N ′, N′-dimethylcarbamoyl (methylthio) methylenamine N-methylcarbamate 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 .
^ Entry on Oxamyl in the Hazardous Substances Data Bank , accessed July 29, 2012.
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 140 (English, limited preview in Google Book Search).
↑ EPA: Oxamyl (PDF; 139 kB).
↑ Entry on Oxamyl. In: Römpp Online . Georg Thieme Verlag, accessed on July 17, 2013.
^ Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 561 (English, limited preview in Google Book search).
↑ Springer Environmental Lexicon . 2nd Edition. Springer, Berlin / Heidelberg 2000, ISBN 978-3-642-56998-2 ( limited preview in Google book search [accessed September 13, 2018]).
↑ Directive 2006/16 / EC of the Commission of February 7th, 2006 amending Council Directive 91/414 / EEC to include the active ingredient Oxamyl .
↑ Implementing Regulation (EU) No. 540/2011 of the Commission of 25 May 2011 for the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances .
↑ Active ingredients in plant protection products - authorization history .
^ Directorate-General for Health and Food Safety of the European Commission: Entry on Oxamyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

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

[inchem-2] WHO / FAO Data Sheet on Pesticides (PDS) for Oxamyl ( Memento of July 2, 2014 in the Internet Archive ).

[Buchanan-3] Buchanan, JB: Preparation of 1- (Carbamoyl) -n- (carbamoyloxy) thio-formamidates from Alkyl Acetoacetates , Patent US3557190 (Du Pont de Nemours), January 19, 1971.

[CLP_100.041.299-4] Entry on N ′, N′-dimethylcarbamoyl (methylthio) methylenamine N-methylcarbamate 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 .

[hsdb-5] Entry on Oxamyl in the Hazardous Substances Data Bank , accessed July 29, 2012.

[Unger-6] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 140 (English, limited preview in Google Book Search).

[7] EPA: Oxamyl (PDF; 139 kB).

[Römpp-8] Entry on Oxamyl. In: Römpp Online . Georg Thieme Verlag, accessed on July 17, 2013.

[Roberts-9] Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 561 (English, limited preview in Google Book search).

[umweltlex-10] Springer Environmental Lexicon . 2nd Edition. Springer, Berlin / Heidelberg 2000, ISBN 978-3-642-56998-2 ( limited preview in Google book search [accessed September 13, 2018]).

[11] Directive 2006/16 / EC of the Commission of February 7th, 2006 amending Council Directive 91/414 / EEC to include the active ingredient Oxamyl .

[12] Implementing Regulation (EU) No. 540/2011 of the Commission of 25 May 2011 for the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances .

[13] Active ingredients in plant protection products - authorization history .

[PSM-14] Directorate-General for Health and Food Safety of the European Commission: Entry on Oxamyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.