Phosphamidon

• (IUPAC) (E, Z )-3- chloro-4- diethylamino -4- oxobut -2 -en- 2-yl - dimethylphosphate
• 2- chloro-2- diethylcarbamoyl -1 - methylvinyldimethylphosphat
• 2- chloro-3- diethylamino -1-methyl -3- oxo-1- propenyldimethylphosphat
• Dimethylphosphatester -2-chloro -N, N -diethyl -3- hydroxycrotonamide
• Trade names: Apamidon ®, Dimecron ®, Dimenox ® Dixon ®, Phosron ®, Pillarcron ®

Odorless, clear, yellowish liquid

Liquid

1.2132 g · cm -3

45 ° C.

162 ° C (2 bar)

3.39 · 10-5 mbar (at 20 ° C)

Water-miscible, polar organic solvents

1.4721

Risk

Template: Infobox chemical / molecular formula search available

Phosphamidon is an organic chemical compound with the formula C10H19ClNO5P, which was first described in 1960. It belongs to the groups of the phosphoric esters and organophosphate insecticides.

Representation

The synthesis starts from N, N- diethylacetamide. By treatment with phosphoryl the diethyl is acetylated to Diethylacetoacetamid. With sulfuryl chloride, the methyl group is chlorinated. The intermediate product N, N- Diethyldichloracetoacetamid results in the reaction with trimethyl phosphite, phosphorus oxychloride or the final product.

Cis -trans isomerism

Phosphamidon subject to the Oxobutendoppelbindung the cis- trans isomerism. As an insecticide (commercial product ) an isomer mixture of 70 % ( Z) - (cis )-isomer and 30% ( E) - ( trans) - isomer used.

Properties and Uses

Under normal conditions phosphamidon is a clear, pale yellow, odorless liquid. It mixes with many polar organic solvents and in all proportions with water. Phosphamidon may contain flammable solvents as a commercial product whose influence can completely change the chemical, physical and toxicological properties. During heating or burning the fabric to form hydrogen chlorides, phosphorus oxides and nitrogen oxides decomposed. With bases phosphamidon reacts with hydrolysis. Metals such as aluminum, iron and tin are being attacked, and to acids in neutral solution it is stable.

Phosphamidon was first described in 1960 and introduced as a systemically acting insecticide. The large-scale production as an insecticide was stopped in 1990, for scientific purposes, it is still available.

Phosphamidon is not approved as an active ingredient in pesticides for the countries of the European Union. Also in Switzerland is phosphamidon as in Austria and Germany no active ingredient in approved pesticides.

Toxicity

As a phosphoric acid ester phosphamidon is very toxic to humans and animals and thus highly dangerous for the environment, especially for the aquatic fauna. From the WHO it is ( " extremely dangerous " or " extremly hazardous ") in the Class Ia listed. Phosphamidon acts as an inhibitor of cholinesterase ( acetylcholinesterase ( AChE) and butyrylcholinesterase ( BuChE ) ). It is toxic by skin contact (contact and nerve poison ), inhalation and ingestion. By storing in fat brain and a long-term effect may be caused, depending on dose, genotype and additive poisons. The LD50 p.o. ( per os, oral) is estimated to mice at 13 mg / kg, for rats at 20 mg / kg ..