Carbaryl (1-naphthyl methylcarbamate) is a chemical in the
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 ...
family used chiefly 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 ...
. It is a white crystalline solid previously sold under the brand name Sevin, which was a trademark of the
Bayer
Bayer AG (English: , commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and is one of the largest pharmaceutical companies and biomedical companies in the world. Headquartered in Leverkusen, Bayer' ...
Company.
Union Carbide
Union Carbide Corporation (UCC) is an American chemical company headquartered in Seadrift, Texas. It has been a wholly owned subsidiary of Dow Chemical Company since 2001. Union Carbide produces chemicals and polymers that undergo one or more f ...
discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. Carbaryl was the third-most-used insecticide in the United States for home
gardens
A garden is a planned space, usually outdoors, set aside for the cultivation, display, and enjoyment of plants and other forms of nature. The single feature identifying even the wildest wild garden is ''control''. The garden can incorporate bot ...
, commercial agriculture, and forestry and rangeland protection. As a
veterinary
Veterinary medicine is the branch of medicine that deals with the prevention, management, diagnosis, and treatment of disease, disorder, and injury in non-human animals. The scope of veterinary medicine is wide, covering all animal species, both ...
drug, it is known as carbaril (
INN).
Production
Carbaryl is often inexpensively produced by direct reaction of
methyl isocyanate with
1-naphthol
1-Naphthol, or α-naphthol, is an organic compound with the formula . It is a fluorescent white solid. 1-Naphthol differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene ...
.
:C
10H
7OH + CH
3NCO → C
10H
7OC(O)NHCH
3
Alternatively, 1-naphthol can be treated with excess
phosgene
Phosgene is an organic chemical compound with the formula . It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of ...
to produce 1-
naphthyl chloroformate, which is then converted to carbaryl by reaction with
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 ...
.
[ The former process was used in the chemical plant that caused the ]Bhopal disaster
On 3 December 1984, over 500,000 people in the vicinity of the Union Carbide India Limited pesticide plant in Bhopal, Madhya Pradesh, India were exposed to the highly toxic gas methyl isocyanate, in what is considered the world's worst ind ...
. In comparison, the latter synthesis uses exactly the same reagents required for the synthesis of methyl isocyanate. This route avoids the potential hazards of methyl isocyanate, allbeit at a higher cost.
Biochemistry
Carbamate insecticides are slowly irreversible inhibitors of the enzyme acetylcholinesterase
Acetylcholinesterase (HUGO Gene Nomenclature Committee, HGNC symbol ACHE; EC 3.1.1.7; systematic name acetylcholine acetylhydrolase), also known as AChE, AChase or acetylhydrolase, is the primary cholinesterase in the body. It is an enzyme th ...
. They resemble acetylcholine
Acetylcholine (ACh) is an organic compound that functions in the brain and body of many types of animals (including humans) as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Par ...
, but the carbamoylated enzyme undergoes the final hydrolysis step very slowly (minutes) compared with the acetylated enzyme generated by acetylcholine (microseconds). They interfere with the cholinergic nervous system and cause death because the effects of the neurotransmitter acetylcholine cannot be terminated by carbamoylated acetylcholinesterase.
Applications
The development of the carbamate insecticides has been called a major breakthrough in pesticide
Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...
s. The carbamates do not have the persistence of chlorinated pesticides. Although toxic to insects, carbaryl is detoxified and eliminated rapidly in vertebrates. It is neither concentrated in fat nor secreted in milk, so is favored for food crops, at least in the US.[Robert L. Metcalf "Insect Control" in Ullmann's ''Encyclopedia of Industrial Chemistry'' Wiley-VCH, Weinheim, 2002. ] It is the active ingredient in Carylderm shampoo used to combat head lice until infestation is eliminated.
Ecology
Carbaryl kills both targeted (e.g., malaria-carrying mosquitos) and beneficial insects (e.g., honeybee
A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to mainland Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the c ...
s), as well as crustaceans.[Carbaryl General Fact Sheet - National Pesticide Information Center](_blank)
/ref> Because it is highly toxic to zooplankton
Zooplankton are the heterotrophic component of the planktonic community (the " zoo-" prefix comes from ), having to consume other organisms to thrive. Plankton are aquatic organisms that are unable to swim effectively against currents. Consequent ...
, the algae they feed on experience blooms. Boone & Bridges 2003 find that larger algae eaters such as '' Bufo woodhousii'' benefit from this effect.[ 5.4.1 Taxon-Wide Impacts — Pesticides and Contaminants, and Their Roles in the Decline of Amphibian Populations. Moore, Robin D.; Claude Gascon. pp.111-145.]
Although it can increase survival rates for organisms that benefit from consequential algae blooms, the long term effects of these changes in competition levels and predation can be detrimental to many aquatic ecosystems, particularly those dominated by Anurans.
It is approved for more than 100 crops in the US. Carbaryl has been illegal in the EU since 21 November 2007 and Angola.[Carbaryl Insecticide Hazard Data](_blank)
Safety
Carbaryl is a cholinesterase inhibitor
Cholinesterase inhibitors (ChEIs), also known as anti-cholinesterase, are chemicals that prevent the breakdown of the neurotransmitter acetylcholine or butyrylcholine by cholinesterase. This increases the amount of the acetylcholine or butyryl ...
and is toxic to humans. It is classified as a likely human carcinogen
A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...
by the United States Environmental Protection Agency
The Environmental Protection Agency (EPA) is an independent agency of the United States government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it began operation on De ...
(EPA.)Interim Reregistration Eligibility Decision for Carbaryl
, U.S. EPA, June 2003. The oral is 250 to 850 mg/kg for rats and 100 to 650 mg/kg for mice.
Carbaryl can be produced using methyl isocyanate (MIC) as an intermediary.[ A leak of MIC used in the production of carbaryl caused the ]Bhopal disaster
On 3 December 1984, over 500,000 people in the vicinity of the Union Carbide India Limited pesticide plant in Bhopal, Madhya Pradesh, India were exposed to the highly toxic gas methyl isocyanate, in what is considered the world's worst ind ...
, the most lethal industrial accident in history.
References
External links
Carbaryl Technical Fact Sheet - National Pesticide Information Center
* ttp://extoxnet.orst.edu/tibs/cholines.htm Cholinesterase Inhibition - Extension Toxicology Networkbr>EPA info
EPA factsheet
*
{{Authority control
Acetylcholinesterase inhibitors
Carbamate insecticides
IARC Group 3 carcinogens
Endocrine disruptors
Naphthol esters
Veterinary drugs
Aromatic carbamates
1-Naphthyl compounds