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 ...

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 r ...

Uses

Insecticides

A subclass of acylureas known as

benzoylurea 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

insecticide Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...

s. They act as insect growth regulators by inhibiting the synthesis of

chitin Chitin ( C8 H13 O5 N)n ( ) is a long-chain polymer of ''N''-acetylglucosamine, an amide derivative of glucose. Chitin is probably the second most abundant polysaccharide in nature (behind only cellulose); an estimated 1 billion tons of chit ...

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 medicine, veterinary flea control medication Program, and one of the two active ingredients in the flea, heartworm, ringworm and anthelmintic medicine milbemycin oxime/lufenuron (Sentinel). Luf ...

, and teflubenzuron.

Anticonvulsants and sedatives

The acylurea functional group is also found in some pharmaceutical drugs such as the

anticonvulsant Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of b ...

phenacemide 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

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but t ...

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.

Barbiturate Barbiturates are a class of depressant drugs that are chemically derived from barbituric acid. They are effective when used medically as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as we ...

s (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 intr ...

, and may be considered ring-opened analogues of them.

;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 ...

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

Uses

Insecticides

Anticonvulsants and sedatives

Related

References