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Carbofuran 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 ...
pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampri ...
, widely used around the world to control insects on a wide variety of field crops, including
potato The potato is a starchy food, a tuber of the plant ''Solanum tuberosum'' and is a root vegetable native to the Americas. The plant is a perennial in the nightshade family Solanaceae. Wild potato species can be found from the southern Unit ...
es,
corn Maize ( ; ''Zea mays'' subsp. ''mays'', from es, maíz after tnq, mahiz), also known as corn (North American and Australian English), is a cereal grain first domesticated by indigenous peoples in southern Mexico about 10,000 years ago. Th ...
and
soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses. Traditional unfermented food uses of soybeans include soy milk, from which tofu an ...
s. It is a
systemic 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 ...
, which means that the plant absorbs it through the
root In vascular plants, the roots are the organs of a plant that are modified to provide anchorage for the plant and take in water and nutrients into the plant body, which allows plants to grow taller and faster. They are most often below the sur ...
s, and from there the plant distributes it throughout its organs where insecticidal concentrations are attained. Carbofuran also has contact activity against pests. It is one of the most toxic pesticides still in use. It is marketed under the trade names Furadan, by
FMC Corporation FMC Corporation is an American chemical manufacturing company headquartered in Philadelphia, Pennsylvania, which originated as an insecticide producer in 1883 and later diversified into other industries. In 1941 at the beginning of US involvemen ...
and Curaterr 10 GR, by
Bayer Bayer AG (, commonly pronounced ; ) is a German multinational corporation, multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of busi ...
among several others. Carbofuran exhibits toxicity mediated by the same mechanism as that of the notorious
V-series nerve agents V series or V-series may refer to: * Cadillac V series, a line of high-performance vehicles * List of ITU-T V-series recommendations, on data communication over the telephone network * LG V series, a line of high-end Android devices * V series ...
and presents a risk to human health. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the United States
Emergency Planning and Community Right-to-Know Act The Emergency Planning and Community Right-to-Know Act of 1986 is a United States federal law passed by the 99th United States Congress located at Title 42, Chapter 116 of the U.S. Code, concerned with emergency response preparedness. On October ...
(42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.


Usage

Carbofuran is used around the world for a wide variety of crops. It is widely used in Asia, Australia, and South America. It is commonly used in Malaysia for vegetables like eggplant (brinjal) where it is a legally registered pesticide. Carbofuran acts through phloem sap against piercing-sucking pests such as green leafhoppers, brown plant hoppers, stem borers and whorl maggots. Usage has increased in recent years because it is one of the few insecticides effective on soybean
aphid Aphids are small sap-sucking insects and members of the superfamily Aphidoidea. Common names include greenfly and blackfly, although individuals within a species can vary widely in color. The group includes the fluffy white woolly aphids. A t ...
s, which have expanded their range since 2002 to include most soybean-growing regions of the United States.


Chemistry

The technical or chemical name of carbofuran is 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate, and its
CAS Number A CAS Registry Number (also referred to as CAS RN or informally CAS Number) is a unique identification number assigned by the Chemical Abstracts Service (CAS), US to every chemical substance described in the open scientific literature. It inclu ...
is 1563-66-2. It is manufactured by the reaction of
methyl isocyanate Methyl isocyanate (MIC) is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane and methyl carbylamine. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides (such as carbaryl, c ...
with 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran.


Toxicity

Carbofuran has one of the highest acute toxicities to humans of any insecticide widely used on field crops (only
aldicarb Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a cholineste ...
and
parathion Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, incl ...
are more toxic). 1 ml (1/4 teaspoon) can be fatal to humans. Most carbofuran is applied by commercial applicators using closed systems with engineered controls so there is no exposure to it in preparation. However, in developing countries, occupational exposure to carbofuran and resultant carbofuran-serum protein labeling has been reported to impact human health and well-being. Since its toxic effects are due to its activity 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 neurotransmitters ...
inhibitor it is considered a
neurotoxic Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specificall ...
pesticide. A recent study reports that carbofuran is a structural mimic of the neurohormone melatonin and could directly bind to MT2 melatonin receptor (Ki = 1.7 uM). Disruption of melatonin signaling could impact the circadian rhythm balance and is linked to elevated risk of developing diabetes. Carbofuran is highly toxic to vertebrates with an oral of 8–14 mg/kg in rats and 19 mg/kg in dogs. Carbofuran is known to be particularly toxic to birds. In its granular form, a single grain will kill a bird. Birds often eat numerous grains of the pesticide, mistaking them for seeds, and then die shortly thereafter. Before the granular form was banned by the
EPA The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it be ...
in 1991, it was blamed for millions of bird deaths per year. The liquid version of the pesticide is less hazardous to birds since they are not as likely to ingest it directly, but it is still very hazardous. Carbofuran has been illegally used to intentionally poison wildlife not only in the US, Canada and Great Britain; poisoned wildlife have included coyotes,
kites A kite is a tethered heavier than air flight, heavier-than-air or lighter-than-air craft with wing surfaces that react against the air to create Lift (force), lift and Drag (physics), drag forces. A kite consists of wings, tethers and anchors. ...
, golden eagles and buzzards. Secondary fatal poisoning of domestic and wild animals has been documented, specifically raptors (
bald eagles The bald eagle (''Haliaeetus leucocephalus'') is a bird of prey found in North America. A sea eagle, it has two known subspecies and forms a species pair with the white-tailed eagle (''Haliaeetus albicilla''), which occupies the same niche as ...
and
golden eagles The golden eagle (''Aquila chrysaetos'') is a bird of prey living in the Northern Hemisphere. It is the most widely distributed species of eagle. Like all eagles, it belongs to the family Accipitridae. They are one of the best-known birds of ...
), domestic dogs,
raccoon The raccoon ( or , ''Procyon lotor''), sometimes called the common raccoon to distinguish it from other species, is a mammal native to North America. It is the largest of the procyonid family, having a body length of , and a body weight of ...
s,
vulture A vulture is a bird of prey that scavenges on carrion. There are 23 extant species of vulture (including Condors). Old World vultures include 16 living species native to Europe, Africa, and Asia; New World vultures are restricted to North and ...
s and other scavengers. In Kenya, farmers are using carbofuran to kill lions and other predators. In a number of publicized incidents worldwide, carbofuran has also been used to poison domestic pets. Illegally smuggled carbofuran is used on 90% of
marijuana Cannabis, also known as marijuana among other names, is a psychoactive drug from the cannabis plant. Native to Central or South Asia, the cannabis plant has been used as a drug for both recreational and entheogenic purposes and in various tra ...
grown illegally on public land in California. These illegal, carbofuran-contaminated California marijuana grows appear to be the source for the majority of marijuana consumed in states where marijuana hasn't been legalized. Carbofuran is an
endocrine disruptor Endocrine disruptors, sometimes also referred to as hormonally active agents, endocrine disrupting chemicals, or endocrine disrupting compounds are chemicals that can interfere with endocrine (or hormonal) systems. These disruptions can cause c ...
and a probable reproduction/development intoxicant. At low-level exposures, carbofuran may cause transient alterations in the concentration of
hormone A hormone (from the Greek participle , "setting in motion") is a class of signaling molecules in multicellular organisms that are sent to distant organs by complex biological processes to regulate physiology and behavior. Hormones are required ...
s. These alterations may consequently lead to serious reproductive problems following repeated exposure. When exposed ''in utero'' or during lactation, a decrease in sperm motility and sperm count along with an increase in percent abnormal sperm was observed in rats at 0.4 mg/kg dose level. In one study, the exposure of rats to sublethal amounts of carbofuran decreased
testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testes and prostate, as well as promoting secondar ...
by 88%, while the levels of
progesterone Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the m ...
,
cortisol Cortisol is a steroid hormone, in the glucocorticoid class of hormones. When used as a medication, it is known as hydrocortisone. It is produced in many animals, mainly by the ''zona fasciculata'' of the adrenal cortex in the adrenal gland ...
, and
estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development of f ...
were significantly increased (1279%, 202%, and 150%, respectively).


Bans

Carbofuran is banned in
Canada Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by tot ...
and the
European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been des ...
. In 2008, the
United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it be ...
(EPA) announced that it intended to ban carbofuran. In December of that year,
FMC Corp. FMC Corporation is an American chemical manufacturing company headquartered in Philadelphia, Pennsylvania, which originated as an insecticide producer in 1883 and later diversified into other industries. In 1941 at the beginning of US involvemen ...
, the sole US manufacturer of carbofuran, announced that it had voluntarily requested that the EPA cancel all but six of the previously allowed uses of that chemical as a pesticide. With this change, carbofuran usage in the United States would be allowed only on corn, potatoes, pumpkins, sunflowers, pine seedlings and spinach grown for seed. However, in May 2009, the EPA canceled all food tolerances, an action which amounts to a ''de facto'' ban on its use on all crops grown for human consumption.
Kenya ) , national_anthem = "Ee Mungu Nguvu Yetu"() , image_map = , map_caption = , image_map2 = , capital = Nairobi , coordinates = , largest_city = Nairobi , ...
is considering banning carbofuran, but it is legal to buy
over-the-counter Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid prescr ...
in Kenya.


Health scare in Thailand

Due to nonregistration of 4
carcinogenic A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...
chemicals used on crops not listed in the Dangerous Substances Act of
Thailand Thailand ( ), historically known as Siam () and officially the Kingdom of Thailand, is a country in Southeast Asia, located at the centre of the Indochinese Peninsula, spanning , with a population of almost 70 million. The country is bo ...
, vegetables with residues of
methomyl Methomyl is a carbamate insecticide introduced in 1966. It is highly toxic to humans, livestock, pets, and wildlife. The EU and UK imposed a pesticide residue limit of 20 µg/kg for apples and oranges. Methomyl is a common active ingredient in ...
, carbofuran, dicrotophos, and EPN were taken off supermarket shelves in July 2012.


Death of lions in Kenya

In 2009, the
CBS CBS Broadcasting Inc., commonly shortened to CBS, the abbreviation of its former legal name Columbia Broadcasting System, is an American commercial broadcast television and radio network serving as the flagship property of the CBS Entertainm ...
television news magazine ''
60 Minutes ''60 Minutes'' is an American television news magazine broadcast on the CBS television network. Debuting in 1968, the program was created by Don Hewitt and Bill Leonard, who chose to set it apart from other news programs by using a unique styl ...
'' ran an exposé discussing the use of Furadan by Kenyan farmers as a poison to kill African lions. The piece suggested that Furadan was a serious threat to the future of the lion population in Africa. FMC has commented on this issue through the media and their websites including furadanfacts.com. They engaged with government officials, NGOs and others to try and resolve the illegal use of pesticides to kill wildlife. The company took action to stop the sale of this product and instituted a buyback program in East Africa when it was determined that the illegal and intentional misuse of chemicals against wildlife could not be controlled by education or stewardship programs alone. Despite this, however, National Geographic stated in 2018 that carbofuran "is still very much available" in Kenya.


See also

*
Dutch standards Dutch Standards are environmental pollutant reference values (i.e., concentrations in environmental medium) used in environmental remediation, investigation and cleanup. Barring a few exceptions, the target values are underpinned by an environment ...


References


External links


The 'Carbo Wars' – the intentional poisoning of eagles and other wildlife in MarylandWashington Post: Thirteen bald eagles were found dead this is what killed themWebsite devoted to raising the awareness about the use of carbofuran to kill wild animalsCARBOFURAN – A NEW AND EFFECTIVE METHOD OF ILLEGAL KILLING OF OTTERS (Lutra lutra) IN THE CZECH REPUBLICFuradanFacts.com
{{Acetylcholine metabolism and transport modulators Acetylcholinesterase inhibitors Carbamate insecticides Benzofuran ethers at the benzene ring Catechol ethers Phenol esters Insecticides Female reproductive toxicants Aromatic carbamates