Animocarb (Matacil) is an

organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the molecular formula C₁₁ H₁₆ N₂ O₂. It has a colorless or white

crystal A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...

-like appearance and is most commonly 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 ...

History

Aminocarb has been extensively used in eastern Canada since 1976 in order to control the

spruce budworm ''Choristoneura'' is a genus of moths in the family Tortricidae. Several species are serious pests of conifers, such as spruce and are known as spruce budworms. Species *'' Choristoneura adumbratanus'' (Walsingham, 1900) *'' Choristoneura afri ...

. The fate of this chemical in the ecosystem and detection of aminocarb was studied by the use of two-dimensional

thin-layer chromatography Thin-layer chromatography (TLC) is a chromatography technique that separates components in non-volatile mixtures. It is performed on a TLC plate made up of a non-reactive solid coated with a thin layer of adsorbent material. This is called the sta ...

. The use of thin-layer chromatography helped isolate and identify the methyl amino,

amino In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

and

hydroxymethyl The hydroxymethyl group is a substituent with the structural formula . It consists of a methylene bridge ( unit) bonded to a hydroxyl group (). This makes the hydroxymethyl group an alcohol. It has the identical chemical formula with the methoxy g ...

analogues from the

in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

of aminocarb by

liver The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...

homogenates from humans and rats.

Production and uses

Aminocarb is a

carbamate In organic chemistry, a carbamate is a category of organic compounds with the general Chemical formula, formula and Chemical structure, structure , which are formally Derivative (chemistry), derived from carbamic acid (). The term includes orga ...

widely used to protect

cotton Cotton (), first recorded in ancient India, is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure ...

fields, crop fields, and

forests A forest is an ecosystem characterized by a dense community of trees. Hundreds of definitions of forest are used throughout the world, incorporating factors such as tree density, tree height, land use, legal standing, and ecological functio ...

from

insect Insects (from Latin ') are Hexapoda, hexapod invertebrates of the class (biology), class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (Insect morphology#Head, head, ...

infestation. It helps in the control of

aphids Aphids are small sap-sucking insects in the Taxonomic rank, family Aphididae. Common names include greenfly and blackfly, although individuals within a species can vary widely in color. The group includes the fluffy white Eriosomatinae, woolly ...

, soil mollusks,

lepidopterous Lepidoptera ( ) or lepidopterans is an order of winged insects which includes butterflies and moths. About 180,000 species of the Lepidoptera have been described, representing 10% of the total described species of living organisms, making it ...

larvae A larva (; : larvae ) is a distinct juvenile form many animals undergo before metamorphosis into their next life stage. Animals with indirect developmental biology, development such as insects, some arachnids, amphibians, or cnidarians typical ...

, and other types of chewing insects. It is most commonly administered as an

aerosol spray Aerosol spray is a type of dispensing system which creates an aerosol mist of liquid particles. It comprises a can or bottle that contains a payload, and a propellant under pressure. When the container's valve is opened, the payload is forced out ...

Reactions

Aminocarb can be degraded through irradiation and hydrolysis. Hydrolysis of aminocarb

Irradiation

Aminocarb can be broken down by

short-wave Shortwave radio is radio transmission using radio frequencies in the shortwave bands (SW). There is no official definition of the band range, but it always includes all of the high frequency band (HF), which extends from 3 to 30 MHz (appr ...

ultraviolet radiation Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of t ...

Irradiation Irradiation is the process by which an object is exposed to radiation. An irradiator is a device used to expose an object to radiation, most often gamma radiation, for a variety of purposes. Irradiators may be used for sterilizing medical and p ...

is often carried out by a

high pressure In science and engineering the study of high pressure examines its effects on materials and the design and construction of devices, such as a diamond anvil cell, which can create high pressure. ''High pressure'' usually means pressures of thousan ...

xenon Xenon is a chemical element; it has symbol Xe and atomic number 54. It is a dense, colorless, odorless noble gas found in Earth's atmosphere in trace amounts. Although generally unreactive, it can undergo a few chemical reactions such as the ...

- mercury lamp.

Irradiating Irradiation is the process by which an object is exposed to radiation. An irradiator is a device used to expose an object to radiation, most often gamma radiation, for a variety of purposes. Irradiators may be used for sterilizing medical and p ...

aminocarb in

ethyl alcohol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an alcohol, with its formula also written as , or EtOH, where Et is the pseudoelement symbol ...

and

cyclohexene Cyclohexene is a hydrocarbon with the formula . It is a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. Among its uses, it is an chemical intermediate, intermediate in the commercial synthesis of nylon. Prod ...

solution Solution may refer to: * Solution (chemistry), a mixture where one substance is dissolved in another * Solution (equation), in mathematics ** Numerical solution, in numerical analysis, approximate solutions within specified error bounds * Solu ...

s initially causes the

oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

of the dimethylamine moiety. The process eventually leads to the formation of a 4-dimethylamino-3-methyl phenol product.

Hydrolysis

Aminocarb undergoes

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

to 4-dimethylamino-3-methylphenol in 25 °C purified water when pH of the water is 6.4. 4-dimethylamino-3-methylphenol is then either directly or via 2-methyl-1,4-dihydorquinone converted to 2-methyl-1,4-benzoquinone. If

methylamine Methylamine, also known as methanamine, is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold ...

diethylamine Diethylamine is an organic compound with the formula . It is classified as a secondary amine. It is a flammable, volatile weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear br ...

are present in the solution 2-methyl-1,4-benzoquinone will readily react. Monoepoxides and diepoxides of 2-methyl-1,4-benzoquinone are formed.

Biomedical effects

In an experiment where young

brown bullhead The brown bullhead (''Ameiurus nebulosus'') is a fish of the family Ictaluridae that is widely distributed in North America. It is a species of bullhead catfish and is similar to the black bullhead (''Ameiurus melas'') and yellow bullhead (' ...

were exposed to aminocarb at lethal and

sublethal Non-lethal weapons, also called nonlethal weapons, less-lethal weapons, less-than-lethal weapons, non-deadly weapons, compliance weapons, or pain-inducing weapons are weapons intended to be less likely to kill a living target than conventiona ...

concentrations, their tissue distribution was examined and showed that the concentration of residues in each tissue increased with the concentration of exposure of aminocarb. The liver and stomach/intestine had the highest amount of accumulation of residues. Aminocarb is also known as a

cholinesterase The enzyme cholinesterase (EC 3.1.1.8, choline esterase; systematic name acylcholine acylhydrolase) catalyses the hydrolysis of choline-based esters: : an acylcholine + H2O = choline + a carboxylate Several of these serve as neurotransmitte ...

inhibitor that has

nervous system In biology, the nervous system is the complex system, highly complex part of an animal that coordinates its behavior, actions and sense, sensory information by transmitting action potential, signals to and from different parts of its body. Th ...

effects causing convulsions and

respiratory failure Respiratory failure results from inadequate gas exchange by the respiratory system, meaning that the arterial oxygen, carbon dioxide, or both cannot be kept at normal levels. A drop in the oxygen carried in the blood is known as hypoxemia; a r ...

. It can also be absorbed through the skin, causing long-term effects to the

and

References

{{Acetylcholine metabolism and transport modulators Acetylcholinesterase inhibitors Carbamate insecticides Anilines Aromatic carbamates Phenol esters Dimethylamino compounds