Tetrasul

Tetrasul
Names
	IUPAC name 1,2,4-trichloro-5-(4-chlorophenyl)sulfanylbenzene
Identifiers
CAS Number	2227-13-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82162;
ChEMBL	ChEMBL1365576;
ChemSpider	15822;
DrugBank	DB12838;
ECHA InfoCard	100.017.057
EC Number	218-761-4;
KEGG	C19032;
PubChem CID	16685;
UNII	BEO7JP5U0R;
CompTox Dashboard (EPA)	DTXSID5020314 ;
	InChI InChI=1S/C12H6Cl4S/c13-7-1-3-8(4-2-7)17-12-6-10(15)9(14)5-11(12)16/h1-6H Key: QUWSDLYBOVGOCW-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1SC2=CC(=C(C=C2Cl)Cl)Cl)Cl;
Properties
Chemical formula	C12H6Cl4S
Molar mass	324.04 g·mol−1
Appearance	white
Melting point	88.4 °C (191.1 °F; 361.5 K)
Boiling point	200 °C (392 °F; 473 K) (1.29 hPa)
Solubility in water	practically insoluble
log P	6.9
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H312, H412
Precautionary statements	P273, P280, P302+P352, P317, P321, P362+P364, P501
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	3960 mg/kg (rat, oral); 2000 mg/kg (rabbit, dermal)
LC50 (median concentration)	11 mg/L (fish, 96 hours)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tetrasul is an organic compound belonging to the groups of thioethers and biphenyls used historically as an acaricide to kill mites and ticks on crops. Because of its high potential for environmental bioaccumulation and toxicity, it has been banned in Europe since 2003.

Synthesis

Tetrasul can be synthesized by etherifying 2,4,5-trichlorothiophenol with p-chloronitrobenzene in the presence of sodium hydroxide via a Williamson ether synthesis. The resulting product is then reduced with iron, followed by reaction with nitrous acid and copper(I) chloride in a Sandmeyer reaction.

Uses

Tetrasul was used as an acaricide on cucumbers and tomatoes.

Approval

In the European Union, Tetrasul was not included in Annex I to Directive 91/414/EEC, pursuant to Regulation (EC) No. 2076/2002 of November 20, 2002. Consequently, plant protection products containing Tetrasul may not be authorized in EU member states.

In Germany, Austria, and Switzerland, no plant protection products containing this active ingredient are authorized.

References

1 2 3 Record of Tetrasul in the GESTIS Substance Database of the Institute for Occupational Safety and Health
↑ "Tetrasul". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-10-20.
↑ Thomas A. Unger (1996), Pesticide synthesis handbook, William Andrew, p. 832, ISBN 978-0815514015
↑ Müfit Bahadir, Harun Parlar, Michael Spiteller (2000), Springer Umweltlexikon, Springer, p. 1162, ISBN 978-3540635611{{citation}}: CS1 maint: multiple names: authors list (link)
↑ "COMMISSION REGULATION (EC) No 2076/2002 of 20 November 2002 extending the time period referred to in Article 8(2) of Council Directive 91/414/EEC and concerning the non-inclusion of certain active substances in Annex I to that Directive and the withdrawal of authorisations for plant protection products containing these substances".
↑ "EU Pesticides Database". ec.europa.eu. Retrieved 2026-10-18.

[GESTIS-1] 1 2 3 Record of Tetrasul in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[2] "Tetrasul". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-10-20.

[Unger-3] Thomas A. Unger (1996), Pesticide synthesis handbook, William Andrew, p. 832, ISBN 978-0815514015

[Springer-4] Müfit Bahadir, Harun Parlar, Michael Spiteller (2000), Springer Umweltlexikon, Springer, p. 1162, ISBN 978-3540635611{{citation}}: CS1 maint: multiple names: authors list (link)

[5] "COMMISSION REGULATION (EC) No 2076/2002 of 20 November 2002 extending the time period referred to in Article 8(2) of Council Directive 91/414/EEC and concerning the non-inclusion of certain active substances in Annex I to that Directive and the withdrawal of authorisations for plant protection products containing these substances".

[6] "EU Pesticides Database". ec.europa.eu. Retrieved 2026-10-18.