Pirimiphos-methyl, marketed as Actellic and Sybol, is a

phosphorothioate Thiophosphates (or phosphorothioates, PS) are chemical compounds and anions with the general chemical formula (''x'' = 0, 1, 2, or 3) and related derivatives where organic groups are attached to one or more O or S. Thiophosphates feature tetrahedr ...

used as an

insecticide Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...

. It was originally developed by

Imperial Chemical Industries Imperial Chemical Industries (ICI) was a British Chemical industry, chemical company. It was, for much of its history, the largest manufacturer in Britain. Its headquarters were at Millbank in London. ICI was listed on the London Stock Exchange ...

Ltd., now

Syngenta Syngenta Global AG is a global agricultural technology company headquartered in Basel, Switzerland. It primarily covers crop protection and seeds for farmers. Syngenta is part of the Syngenta Group, entirely owned by Sinochem, a Chinese state ...

, at their

Jealott's Hill Jealott's Hill is a village in the county of Berkshire, England, within the civil parish of Warfield. The settlement is on the A3095 road approximately north of Bracknell. The nearest railway station is in . History The name of the hill is re ...

site and first marketed in 1977, ten years after its discovery. This is one of several compounds used for vector control of ''

Triatoma ''Triatoma'' is a genus of assassin bug in the subfamily Triatominae (kissing bugs). The members of ''Triatoma'' (like all members of Triatominae) are blood-sucking insects that can transmit serious diseases, such as Chagas disease. Their saliva ...

''. These insects are implicated in the transmission of

Chagas disease Chagas disease, also known as American trypanosomiasis, is a tropical parasitic disease caused by ''Trypanosoma cruzi''. It is spread mostly by insects in the subfamily Triatominae, known as "kissing bugs". The symptoms change throughout the ...

in the Americas. Pirimiphos-methyl can be applied as an interior surface paint additive, in order to achieve a residual pesticide effect.

Synthesis

Pirimiphos methyl is manufactured in a two-step process in which ''N'',''N''-diethylguanidine is reacted with

ethyl acetoacetate The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a colorless liquid. It is widely used as a chemical intermediate in the production of a wide variety of compounds. Preparation At large scale, ethyl ac ...

to form a

pyrimidine Pyrimidine (; ) is an aromatic, heterocyclic, organic compound similar to pyridine (). One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring. The oth ...

ring and its

hydroxy group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

is combined with dimethyl chlorothiophosphate to form the insecticide. : Pirimiphos-methyl synthesis

Pyrimiphos-ethyl is a related insecticide in which the

methoxy group In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

s are replaced with ethoxy groups.

References

External links

* {{Acetylcholine metabolism and transport modulators Acetylcholinesterase inhibitors Organothiophosphate esters Pesticides Aminopyrimidines Diethylamino compounds Methoxy compounds