Nitrofen

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Structural formula
Structural formula of nitrofen
General
Surname Nitrofen
other names
  • 2,4-dichloro-1- (4-nitrophenoxy) benzene
  • 2,4-dichlorophenyl-4′-nitrophenyl ether ( IUPAC )
Molecular formula C 12 H 7 Cl 2 NO 3
Brief description

techn. Product: brown; Basic substance: colorless crystals

External identifiers / databases
CAS number 1836-75-5
EC number 217-406-0
ECHA InfoCard 100.015.824
PubChem 15787
ChemSpider 15010
Wikidata Q414023
properties
Molar mass 284.10 g · mol -1
Physical state

firmly

density

1.8 g cm −3

Melting point

70-71 ° C

boiling point

180–190 ° C (0.33 hPa)

Vapor pressure

1 m Pa (40 ° C)

solubility
  • practically insoluble in water (1 mg l −1 at 22 ° C)
  • soluble in acetone, ethyl acetate, methanol, methylene chloride and xylene
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
08 - Dangerous to health 07 - Warning 09 - Dangerous for the environment

danger

H and P phrases H: 302-350-360D-410
P: 201-273-308 + 313-501
Toxicological data

740 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nitrofen is a herbicide that has been used in agriculture for a long time . It was developed as a herbicide in the USA in 1964 and sold worldwide under the trade names Trizilin , TOK and Trazalex . Nitrofen residues in eggs and poultry triggered the nitrofen scandal in the summer of 2002.

Nitrofen interferes with the hormonal system . It is similar to a thyroid hormone and is considered mutagenic ( mutagenic ). In animal experiments, nitrofen has been shown to be carcinogenic and teratogenic. Since it is not broken down by the body, it accumulates in adipose tissue when animals are fed. In laying hens it can pass into the eggs.

use

The use of nitrofen has been banned in the Federal Republic of Germany since 1980 . Since 1990 the ban has also applied to eastern Germany . The European Union banned nitrofen for all member states in 1988. Nitrofen is no longer permitted in Switzerland either.

As a selective contact herbicide, nitrofen was mainly used in the pre-emergence method. Since it is only effective when exposed to light, it should not be worked into the ground. Nitrofen was mainly used against grass weeds in grain cultivation, especially against wind stalk and field foxtail . It was also used, for example, in the cultivation of vegetables, potatoes and cotton against grasses and dicotyledonous weeds.

It is a brown, crystalline powder and was traded as a wettable powder or as a 25% emulsion concentrate.

Limit values

According to the Maximum Residue Quantity Ordinance (RHmV) of October 21, 1999, the tolerable amount of nitrofen per kilogram of food is a maximum of 0.01 milligrams. As a result of the nitrofen scandal (see below), the limit value for baby and toddler food was lowered to 0.005 mg. The detection limit for nitrofen is 0.004 mg / kg.

Nitrofen scandal

The nitrofen scandal became known in Germany in the summer of 2002. In 1988, a complete ban on sales and use of the herbicidal active ingredient nitrofen and substances containing nitrofen was enacted in the then EC (now the EU ), and thus also valid in the Federal Republic, where the marketing authorization for agents containing nitrofen had expired in 1980.

At that time the GDR still existed, in which nitrofen and other pesticides banned in the EU were still permitted and in use. It was only adopted in 1990 for the new federal states. Accordingly, there were leftovers in storage after reunification. For example, grain for animal feed was stored in a warehouse that had not been adequately checked and cleaned after the pesticides had been stored. The grain was thereby contaminated with nitrofen when it was fed to poultry. Since the grain was sold as organic feed, eggs and poultry from organic farms were particularly affected.

The increased nitrofen values ​​were noticed for the first time in November 2001 at a baby food manufacturer whose laboratory verified the values. At first the company tried to get its suppliers to remedy the situation, but it failed. The increased values ​​remained undiscovered for a relatively long time because at that time, due to the long-standing ban, no routine tests were carried out for nitrofen. It was not until June 2002 that the European Commission was informed of the contamination via the rapid alert system for food and feed . The food scandal briefly brought consumer protection minister Renate Künast into distress.

The direct and indirect damage caused by the scandal was estimated by the German Farmers' Association at around 500,000 euros and made a decisive contribution to Regulation (EC) No. 1935/2004 "on materials and objects that are intended to come into contact with food" .

literature

  • Focus No. 1/2002, Behrs Verlag, Hamburg, The Nitrofen Scandal
  • Florian Deising: The Nitrofen Scandal - On the Necessity of Cooperative Communication Strategies , Münster 2003, digitized

Web links

Individual evidence

  1. ↑ a b c d Werner Perkow: Active substances in plant protection and pest control agents , 2nd edition, Paul Parey publishing house.
  2. ↑ a b Joint Meeting on Pesticide Residues (JMPR), Monograph for Nitrofen , accessed December 9, 2014.
  3. ↑ a b c d e Entry on nitrofen in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  4. ↑ Entry on nitrofen in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ General Directorate Health and Food Safety of the European Commission: Entry on nitrofen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.
  6. ↑ REGULATION (EC) No. 1935/2004 on materials and objects that are intended to come into contact with food (PDF) at EUR-Lex