Acylureas (also called ''N''-acylureas or ureides) are a class of chemical compounds formally derived from the

acylation In chemistry, acylation is a broad class of chemical reactions in which an acyl group () is added to a substrate. The compound providing the acyl group is called the acylating agent. The substrate to be acylated and the product include the foll ...

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

Uses

Insecticides

A subclass of acylureas known as benzoylureas are

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 ...

s. They act as

insect growth regulator An insect growth regulator (IGR) is a chemical insecticide that kills insects indirectly by disrupting their life cycles. The term was initially proposed to describe the effects of juvenile hormone analogs. Although the term "insect growth disrupto ...

s by inhibiting the synthesis of

chitin Chitin (carbon, C8hydrogen, H13oxygen, O5nitrogen, N)n ( ) is a long-chain polymer of N-Acetylglucosamine, ''N''-acetylglucosamine, an amide derivative of glucose. Chitin is the second most abundant polysaccharide in nature (behind only cell ...

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 a process by which an animal casts off parts of its body to serve some beneficial purpose, either at ...

. 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, and anthelmintic medicine milbemycin oxime/lufenuron (Sentinel). Lufenuron is stored in the anim ...

, 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, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also used in the treatme ...

phenacemide Phenacemide (International Nonproprietary Name, INN, British Approved Name, BAN) (brand name Phenurone), also known as phenylacetylurea, is an anticonvulsant of the ureide (acetylurea) class. It is a congener (chemistry), congener and ring-opene ...

pheneturide Pheneturide (International Nonproprietary Name, INN, British Approved Name, BAN) (brand names Benuride, Deturid, Pheneturid, Septotence, Trinuride), also known as phenylethylacetylurea (or ethylphenacemide), is an anticonvulsant of the ureide cla ...

, chlorphenacemide, and acetylpheneturide (which are phenylureides), and the

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or Psychomotor agitation, excitement. They are central nervous system (CNS) Depressant, depressants and interact with brain activity, causing its decelera ...

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. As of 2015, it was still used in Hun ...

(which are

bromoureide Bromoureides are sedative-hypnotics available mainly in Europe and Asia Asia ( , ) is the largest continent in the world by both land area and population. It covers an area of more than 44 million square kilometres, about 30% of Earth's tot ...

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. Though it is not a bar ...

(apronalide), capuride, and ectylurea.

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

s (a class of cyclic ureas) are structurally and mechanistically related to them. The phenylureides are also closely related to the

hydantoin Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sen ...

s, such as

phenytoin Phenytoin (PHT), sold under the brand name Dilantin among others, is an anticonvulsant, 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 se ...

, 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 Chemical formula, 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 meta ...

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 Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sen ...

, or glycolylurea, can be considered the cyclic form of acylurea.

References