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 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 ...

History

Aminocarb has been extensively used in eastern Canada since 1976 in order to control the spruce budworm. The fate of this chemical in the ecosystem and detection of aminocarb was studied by the use of two-dimensional thin-layer chromatography. The use of thin-layer chromatography helped isolate and identify the methyl amino, amino and

hydroxymethyl The hydroxymethyl group is the name for a substituent with the structural formula −CH2−OH. It consists of a methylene bridge (−CH2− unit) bonded to a hydroxyl group (−OH). This makes the hydroxymethyl group an alcohol. It has the identic ...

analogues from the

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

metabolism Metabolism (, from el, μεταβολή ''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 cell ...

of aminocarb by

liver The liver is a major Organ (anatomy), organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of proteins and biochemicals necessary for ...

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 formula and structure , which are formally derived from carbamic acid (). The term includes organic compounds (e.g., the ester ethyl carbamate), formally o ...

widely used to protect

cotton Cotton 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 cellulose, and can contain minor perce ...

fields, crop fields, and forests from

insect Insects (from Latin ') are pancrustacean hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body ( head, thorax and abdomen), three pairs ...

infestation. It helps in the control of aphids, soil mollusks,

lepidopterous Lepidoptera ( ) is an order of insects that includes butterflies and moths (both are called lepidopterans). About 180,000 species of the Lepidoptera are described, in 126 families and 46 superfamilies, 10 percent of the total described species ...

larvae A larva (; plural larvae ) is a distinct juvenile form many animals undergo before metamorphosis into adults. Animals with indirect development such as insects, amphibians, or cnidarians typically have a larval phase of their life cycle. The ...

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

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 shortwave (SW) radio frequencies. There is no official definition of the band, but the range always includes all of the high frequency band (HF), which extends from 3 to 30 MHz (100 to 10 me ...

ultraviolet radiation. Irradiation is often carried out by a high pressure

xenon Xenon is a chemical element with the 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 Mercury commonly refers to: * Mercury (planet), the nearest planet to the Sun * Mercury (element), a metallic chemical element with the symbol Hg * Mercury (mythology), a Roman god Mercury or The Mercury may also refer to: Companies * Merc ...

lamp.

Irradiating Irradiation is the process by which an object is exposed to radiation. The exposure can originate from various sources, including natural sources. Most frequently the term refers to ionizing radiation, and to a level of radiation that will serve ...

aminocarb in ethyl alcohol and

cyclohexene Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light an ...

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 * Soluti ...

s initially causes the

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

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 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 as a solution in methanol, ...

or diethylamine 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 (''Ame ...

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 conventional ...

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 inhibitor that has

nervous system In biology, the nervous system is the highly complex part of an animal that coordinates its actions and sensory information by transmitting signals to and from different parts of its body. The nervous system detects environmental changes th ...

effects causing convulsions and respiratory failure. 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