Fenamiphos

• Phenamiphos
• (RS)- ethyl-4- methylthio- m- tolylisopropylphosphoramidat

Colorless solid

Fixed

1.191 g · cm -3 ( 23 ° C)

49.3 ° C

150 ° C ( decomposition)

0.12 MPa (20 ° C)

• Slightly soluble in water (0.4 g · l-1 at 20 ° C)
• Soluble in dichloromethane, isopropanol, and toluene

Risk

• 8 mg · kg -1 ( LD50, rat, oral)
• 178 mg · kg -1 ( LD50, Rabbit, transdermal)

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Fenamiphos is a chiral chemical compound selected from the group consisting of phosphoramidates.

Production and representation

Fenamiphos can be obtained by reaction of phosphorus oxychloride with ethanol, 3-methyl -4- thiomethylphenol and isopropylamine.

Properties

Fenamiphos is a solid which is slightly soluble in water. It is compared with other organophosphorus compounds relatively stable to hydrolysis. Its sulfoxide, sulfone, and the sulfone metabolite desisopropylierte similar toxic as the compound itself The two enantiomers exhibit different effects.

Use

Fenamiphos is used as an active ingredient in pesticides. It was first registered in 1972 in the U.S., is used as a nematicide in a number of crops and acts by inhibiting acetylcholinesterase. In the news came the connection because the Brandenburg foodstuffs increased residues of the active ingredient in cucumber measured in November 2011 and has informed about the European rapid alert system, the food authorities in Europe.

In the European Union fenamiphos was approved with effect from 1 August 2007 for " uses as nematicide applied by drip irrigation in greenhouses with permanent structure ".

In Germany, Austria and Switzerland, no plant protection products containing this active ingredient are allowed, however, for example in Spain, Portugal, Italy and Hungary. Fenamiphos was produced by Bayer AG under the trade name Nemacur for the world market, the end of 2010, this product line was sold to the AMVAC Chemical Corporation.