Diafenthiuron

Structural formula
General
Surname	Diafenthiuron
Molecular formula	C 23 H 32 N 2 OS
Brief description	colorless solid
External identifiers / databases
CAS number 80060-09-9 EC number 616-885-7 ECHA InfoCard 100.113.249 PubChem 3034380 Wikidata Q15632894
properties
Molar mass	384.58 g mol −1
Physical state	firmly
Melting point	149 ° C
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 332 P: no P-phrases
Toxicological data	2068 mg kg −1 ( LD 50 ,  rat ,  oral ) > 2000 mg kg −1 ( LD 50 ,  rat ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diafenthiuron is a chemical compound from the group of thioureas . It was introduced by Ciba-Geigy in 1990 as an insecticide and acaricide .

Extraction and presentation

Diafenthiuron can be obtained by reacting phenol with 2,6-diisopropyl-4-chloroaniline , thiophosgene and tert-butylamine .

properties

Diafenthiuron is a colorless solid that is insoluble in water. According to the European Chemicals Agency , this substance is toxic by inhalation, is very toxic to aquatic life, is very toxic to aquatic life with long lasting effects and can cause damage to organs through prolonged or repeated exposure .

use

Diafenthiuron is used in cotton and vegetable growing against sucking insects. The effect is based on the inhibition of ATP synthesis .

Diafenthiuron itself is a propesticide which is converted into the active carbodiimide form in the plant .

Admission

In the European Union, diafenthiuron was not included in Annex I of Directive 91/414 / EEC with Regulation (EC) No. 2076/2002 of November 20, 2002 . For this reason, plant protection products containing diafenthiuron are no longer permitted in the EU countries . Since 2009, no pesticides containing this active ingredient have been approved in Switzerland either. Despite the harmfulness of the active ingredient, Polo is still sold outside the EU. The Federal Council does not want to ban exports and rather sees a solution that requires the consent of the importing state, similar to the EU. As of 2019, nothing has been changed in this practice. In 2017 Syngenta exported 126.5 tonnes of this from Switzerland, 75 tonnes of which to India . According to research by the non-governmental organization Public Eye , it was responsible for a wave of poisoning with around 800 people, 20 of whom were dead.

Individual evidence

1. ↑ ^{a b c d e f g h i} data sheet Diafenthiuron at Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
2. ↑ ^{a b} Syngenta: Insecticides - POLO® ( Memento from March 9, 2016 in the Internet Archive )
3. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-08-095716-1 , pp. 210 ( limited preview in Google Book search).
4. ↑ InfoCard for 1-t-Butyl-3- (2,6-diisopropyl-4-phenoxyphenyl) thiourea from the European Chemicals Agency (ECHA), accessed on September 24, 2018.
5. ↑ Jørgen Stenersen: Chemical Pesticides Mode of Action and Toxicology . CRC Press, 2004, ISBN 0-203-64683-5 , pp. 44 ( limited preview in Google Book search).
6. ↑ Hartmut Kayser, Phillipp Eilinger: Metabolism of diafenthiuron by microsomal oxidation: procide activation and inactivation as mechanisms contributing to selectivity . In: Pest Manag. Sci. tape 57 , no. 10 , 2001, p. 975-980 , doi : 10.1002 / ps.360 .
7. ↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.
8. ↑ General Directorate Health and Food Safety of the European Commission: Entry on diafenthiuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.
9. ↑ Risk of poisoning in India In: srf.ch , September 18, 2018, accessed on September 24, 2018.
10. ↑ India: Deadly pesticides threaten cotton farmers In: de.euronews.com , September 20, 2018, accessed on September 24, 2018.
11. ↑ Stricter export of dangerous pesticides. In: schweizerbauer.ch . November 22, 2018. Retrieved November 22, 2018 . 
12. ↑ Stefan Häne: Too toxic for Switzerland - but exportable anyway. In: derbund.ch . March 15, 2019, accessed March 16, 2019 . 
13. ↑ Public Eye : Syngenta pesticide produced in Switzerland, partly responsible for deadly wave of poisoning in India . In: publiceye.ch, September 18, 2018, accessed on September 24, 2018.