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Acylureas (also called ''N''-acylureas or ureides) are a class of chemical compounds formally derived from the
Acylureas (also called ''N''-acylureas or ureides) are a class of chemical compounds formally derived from the acylation
In chemistry, acylation (or alkanoylation) is the chemical reaction in which an acyl group () is added to a compound. The compound providing the acyl group is called the acylating agent.
Because they form a strong electrophile when treated with ...
of urea
Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid.
Urea serves an important ...
.
Uses
Insecticides
A subclass of acylureas known asbenzoylurea
Benzoylureas are chemical derivatives of ''N''-benzoyl-''N′''-phenylurea (benzoylurea). They are best known for their use as insecticides. They act as insect growth regulators by inhibiting synthesis of chitin in the insect's body.
One o ...
s are insecticides. They act as insect growth regulators by inhibiting the synthesis of chitin resulting in weakened cuticles
A cuticle (), or cuticula, is any of a variety of tough but flexible, non-mineral outer coverings of an organism, or parts of an organism, that provide protection. Various types of "cuticle" are non- homologous, differing in their origin, structu ...
and preventing molting
In biology, moulting (British English), or molting (American English), also known as sloughing, shedding, or in many invertebrates, ecdysis, is the manner in which an animal routinely casts off a part of its body (often, but not always, an outer ...
. Members of this class include diflubenzuron
Diflubenzuron is an insecticide of the benzoylurea class. It is used in forest management and on field crops to selectively control insect pests, particularly forest tent caterpillar moths, boll weevils, gypsy moths, and other types of moths. ...
, flufenoxuron, hexaflumuron, lufenuron
Lufenuron is the active ingredient in the veterinary flea control medication Program, and one of the two active ingredients in the flea, heartworm, ringworm and anthelmintic medicine milbemycin oxime/lufenuron (Sentinel).
Lufenuron is stored in ...
, and teflubenzuron.
Anticonvulsants and sedatives
The acylurea functional group is also found in some pharmaceutical drugs such as the anticonvulsantsphenacemide
Phenacemide (INN, BAN) (brand name Phenurone), also known as phenylacetylurea, is an anticonvulsant of the ureide (acetylurea) class. It is a congener and ring-opened analogue of phenytoin (a hydantoin), and is structurally related to the barb ...
, pheneturide
Pheneturide ( INN, BAN) (brand names Benuride, Deturid, Pheneturid, Septotence, Trinuride), also known as phenylethylacetylurea (or ethylphenacemide), is an anticonvulsant of the ureide class. Conceptually, it can be formed in the body as a metabo ...
, chlorphenacemide, and acetylpheneturide (which are phenylureides), and the sedatives acecarbromal
Acecarbromal ( INN) (brand names Sedamyl, Abasin, Carbased, Paxarel, Sedacetyl, numerous others), also known as acetylcarbromal and acetyladalin, is a hypnotic and sedative drug of the ureide (acylurea) group discovered by Bayer in 1917 that was f ...
, bromisoval
Bromisoval ( INN), commonly known as bromovalerylurea, is a hypnotic and sedative of the bromoureide group discovered by Knoll in 1907 and patented in 1909. It is marketed over the counter in Asia under various trade names (such as ''Brovarin' ...
, and carbromal
Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer and subsequently marketed as Adalin. The drug was later sold by Parke-Davis in combination with pentobarbital, under the name Carbrital.
Synthesis
Diethylmalonic acid 10- ...
(which are bromoureide Bromoureides are sedative-hypnotics available mainly in Europe, including acecarbromal, bromisoval, and carbromal (Horowitz, 1997). They are a subfamily of the ureides (acylureas).
See also
* Apronal
Apronal (brand name Sedormid), or apronali ...
s). Others include apronal
Apronal (brand name Sedormid), or apronalide, also known as allylisopropylacetylurea or allylisopropylacetylcarbamide, is a hypnotic/sedative drug of the ureide (acylurea) group synthesized in 1926 by Hoffmann-La Roche that is no longer used exc ...
(apronalide), capuride, and ectylurea. Barbiturates (a class of cyclic ureas) are structurally and mechanistically related to them. The phenylureides are also closely related to the hydantoins, such as phenytoin
Phenytoin (PHT), sold under the brand name Dilantin among others, is an anti-seizure medication. It is useful for the prevention of tonic-clonic seizures (also known as grand mal seizures) and focal seizures, but not absence seizures. The in ...
, and may be considered ring-opened analogues of them.
Related
;Diureides A diureide is a complex nitrogenous substance regarded as containing two molecules of urea or their radicals, e.g.uric acid
Uric acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the formula C5H4N4O3. It forms ions and salts known as urates and acid urates, such as ammonium acid urate. Uric acid is a product of the metabolic breakdown ...
or allantoin
Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacter ...
.
;Hydantoins
Hydantoin, or glycolylurea, can be considered the cyclic form of acylurea.
References
{{Reflist, 2 Ureas Functional groups