Thiocyclam

Structural formula
	Structure of thiocyclam hydrogen oxalate
General
Surname	Thiocyclam
other names	N , N -dimethyl-1,2,3-trithiane-5-amine hydrogen oxalate; 1,2,3-trithiacyclohexyldimethylammonium hydrogen oxalate; 5-dimethylamino-1,2,3-trithianhydrogen oxalate; Thiocyclam hydrogen oxalate; Evisect / Evisect;
Molecular formula	C 7 H 13 NO 4 S 3
Brief description	colorless and odorless solid
External identifiers / databases
EC number	608-676-4
ECHA InfoCard	100.127.155
PubChem	35970
ChemSpider	33084
Wikidata	Q15632827
properties
Molar mass	271.38 g mol −1
Physical state	firmly
Melting point	decomposes at 125–128 ° C
solubility	in water depending on the pH value : 16.3 g l −1 at 20 ° C and pH 6.8; 84.0 g l −1 at 20 ° C and pH 3.3;
safety instructions
H and P phrases	H: 312-302-410
	P: ?
Toxicological data	195 mg kg −1 ( LD 50 , rat , oral , hydrogen oxalate) ; 156 mg kg −1 ( LD 50 , mouse , oral , hydrogen oxalate) ; 1000 mg kg −1 ( LD 50 , rat , transdermal , hydrogen oxalate) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Thiocyclam is a chemical compound from the trithiane group that was used as an insecticide . The substance was developed at Sandoz and was available on the market from 1975.

Extraction and presentation

Thiocyclam is obtained in a multi-stage reaction from 2-dimethylamino-1,3-dichloropropane , sodium thiosulfate , sodium sulfide , oxalic acid , hydrogen peroxide and sodium sulfate.

properties

The hydrogen oxalate used as an insecticide is a colorless, odorless, crystalline compound, the water solubility of which is strongly dependent on the pH value : 16.3 g / l dissolve at 20 ° C and pH 6.8, while at pH 3.3 it dissolves 84 g / l.

Effect and toxicology

Thiocyclam was used as a contact and food poison , which blocks the nicotinic acetylcholine receptors in the nervous system of insects . The insecticide is effective against various insect species and also toxic to bees , fish and other aquatic organisms. Thiocyclam degrades rapidly in the environment - with a half-life in the soil of one to four days.

Thiocyclam in mice showed in toxic doses, and when taken orally muscle tremors up to seizures and convulsions as well as disturbance of coordination of movements ( ataxia ); the oral LD ₅₀ value for mice was 156 mg / kg and for rats 195 mg / kg body weight.

Admission

The active ingredient thiocyclam is not approved for use in plant protection products in the European Union . It is no longer contained in plant protection products that are approved in Germany, Austria or Switzerland.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on N, N-dimethyl-1,2,3-trithiane-5-amine hydrogen oxalate in the GESTIS substance database of the IFA , accessed on December 31, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e entry on thiocyclam. In: Römpp Online . Georg Thieme Verlag, accessed on August 14, 2013.
↑ Entry on bis (1,2,3-trithiacyclohexyldimethylammonium) oxalate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 31, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b Entry on thiocyclam in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 742 ( limited preview in Google Book search).
↑ 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.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on thiocyclam 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 Entry on N, N-dimethyl-1,2,3-trithiane-5-amine hydrogen oxalate in the GESTIS substance database of the IFA , accessed on December 31, 2019(JavaScript required) .

[roempp-2] ↑ ^a ^b ^c ^d ^e entry on thiocyclam. In: Römpp Online . Georg Thieme Verlag, accessed on August 14, 2013.

[CLP_100.046.221-3] Entry on bis (1,2,3-trithiacyclohexyldimethylammonium) oxalate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 31, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[chemid-4] Entry on thiocyclam in the ChemIDplus database of the United States National Library of Medicine (NLM)

[unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 742 ( limited preview in Google Book search).

[6] 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.

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