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{{Short description|Toxic carbamate pesticide}}
{{Use mdy dates|date=September 2020}}

{{chembox
{{chembox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 411948563
| verifiedrevid = 443498211
| ImageFile = Carbofuran-from-xtal-2D-skeletal.svg
| ImageFileL1 = Carbofuran-from-xtal-2D-skeletal.svg
| ImageSize =
| ImageSizeL1 = 120px
| ImageName = Carbofuran
| ImageNameL1 = Carbofuran
| ImageFile1 = Carbofuran-from-xtal-3D-balls.png
| ImageFileR1 = Carbofuran-from-xtal-3D-balls.png
| ImageSize1 =
| ImageSizeR1 = 120px
| ImageName1 = Carbofuran
| ImageNameR1 = Carbofuran
| IUPACName = 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate
| PIN = 2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate
| OtherNames = Carbofuran, Furadan, Curater
| OtherNames = Furadan, Curater, Furacarb
| Section1 = {{Chembox Identifiers
| Section1={{Chembox Identifiers
| Abbreviations =
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 16: Line 19:
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 416081
| ChEMBL = 416081
| InChIKey = DUEPRVBVGDRKAG-UHFFFAOYAB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)
| StdInChI = 1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)
Line 25: Line 27:
| EINECS =
| EINECS =
| PubChem = 2566
| PubChem = 2566
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SKF77S6Y67
| UNII = SKF77S6Y67
| SMILES = O=C(Oc2cccc1c2OC(C1)(C)C)NC
| SMILES = CNC(=O)Oc1cccc2c1OC(C)C2
| RTECS =
| InChI = 1/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)
| RTECS =
| MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| MeSHName =
| ChEBI = 34611
| ChEBI = 34611
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14291
| KEGG = C14291
}}
| ATCCode_prefix =
| Section2={{Chembox Properties
| ATCCode_suffix =
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| C=12 | H=15 | N=1 | O=3
| C=12 | H=15 | N=1 | O=3
| Formula =
| MolarMass =
| Appearance = White, crystalline solid
| Appearance = White, crystalline solid
| Density = 1.18 g/cm<sup>3</sup>
| Density = 1.18 g/cm<sup>3</sup>
| MeltingPt = 151°C<ref name="hand">
| MeltingPtC = 151
| MeltingPt_ref =<ref name="hand">{{Cite book |last=Lide |first=David R. |year=1998 |title=Handbook of Chemistry and Physics |edition=87 |location=Boca Raton, Florida |publisher=CRC Press |isbn=978-0-8493-0594-8 |pages=3–94 }}</ref>
{{Cite book
| last = Lide
| BoilingPtC = 313.3
| BoilingPt_notes =
| first = David R.
| Solubility = 320 mg/L<ref>{{cite journal |vauthors=Sharom MS, ((Miles JRW)), Harris CR, McEwen FL |journal=Water Res |volume=14 |issue=8 |pages=1095–1100 |title=Behaviour of 12 Insecticides in soil and aqueous suspensions of soil and sediment |year=1980 |doi=10.1016/0043-1354(80)90158-X|bibcode=1980WatRe..14.1095S }}</ref>
| author-link =
| SolubleOther = Highly soluble in N-methyl-2-pyrrolidone, [[dimethylformamide]], [[dimethyl sulfoxide]], [[acetone]], [[acetonitrile]], [[methylene chloride]], [[cyclohexanone]], [[benzene]], and [[xylene]]<ref>US EPA/OPPTS; Reregistration Eligibility Decisions (REDs) Database on Carbofuran (1563-66-2). EPA-738-R-06-031 August 2006.</ref>
| last2 =
| LogP=2.32 (octanol/water)<ref>{{cite book |author=Hansch, C. |author2=Leo, A. |author3=D. Hoekman |title=Exploring QSAR – Hydrophobic, Electronic, and Steric Constants |location=Washington, DC |publisher=American Chemical Society |date=1995 |page=101}}</ref>
| first2 =
| author2-link =
| publication-date =
| date =
| year = 1998
| title = Handbook of Chemistry and Physics
| edition = 87
| volume =
| series =
| publication-place = Boca Raton, FL
| place =
| publisher = CRC Press
| id =
| isbn = 0-8493-0594-2
| doi =
| oclc =
| pages = 3–94
| url =
| accessdate =
}}</ref>
| Melting_notes =
| BoilingPt = 313.3°C
| Boiling_notes =
| Solubility = 320 mg/L at 25 °C<ref>Sharom MS et al; Water Res 14: 1095-100 (1980)</ref>
| SolubleOther = Highly soluble in N-methyl-2-pyrrolidone, [[dimethylformamide]], [[dimethyl sulfoxide]], [[acetone]], [[acetonitrile]], [[methylene chloride]], [[cyclohexanone]], [[benzene]], and [[xylene]]<ref>US EPA/OPPTS; Reregistration Eligibility Decisions (REDs) Database on Carbofuran (1563-66-2). EPA-738-R-06-031. August 2006.</ref>
| LogP=2.32 (octanol/water)<ref>Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 101</ref>
| Solvent =
| Solvent =
| pKa =
| pKa =
| pKb = }}
| pKb = }}
| Section7 = {{Chembox Hazards
| Section7={{Chembox Hazards
| LD50 = 8–14 mg/kg (oral, rat)<br />19&nbsp;mg/kg (oral, dog)
| ExternalMSDS =
| EUClass =
| ExternalSDS =
| EUIndex =
| MainHazards =
| MainHazards =
| NFPA-H =
| NFPA-H =
| NFPA-F =
| NFPA-F =
| NFPA-R =
| NFPA-R =
| NFPA-O =
| NFPA-S =
| RPhrases =
| FlashPtC = 143.3
| SPhrases =
| AutoignitionPtC =
| RSPhrases =
| FlashPt = 143.3°C
| Autoignition =
| ExploLimits =
| ExploLimits =
| PEL = }}
| PEL = none<ref name="PGCH">{{PGCH|0101}}</ref>
| IDLH = N.D.<ref name="PGCH" />
| REL = TWA 0.1 mg/m<sup>3</sup><ref name="PGCH" />
}}
}}
}}
'''Carbofuran''' is a [[carbamate]] [[pesticide]], widely used around the world to control insects on a wide variety of field crops, including [[potato]]es, [[maize|corn]] and [[soybean]]s. It is a [[systemic insecticide]], which means that the plant absorbs it through the [[root]]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]] and '''Curaterr 10 GR''', by [[Bayer]] among several others.<ref name="Ravichandra 2018 p. 110">{{cite book|last=Ravichandra|first=N.G.|url=https://books.google.com/books?id=PRiUDwAAQBAJ&pg=PA110|title=Agrochemicals in Plant Disease Management|publisher=Scientific Publishers|year=2018|isbn=978-93-87991-91-0|page=110|access-date=September 22, 2020}}</ref>
'''Carbofuran''' is one of the most toxic [[carbamate]] [[pesticide]]s. It is marketed under the trade names '''Furadan''', by [[FMC Corporation]] and '''Curater''', among several others. It is used to control insects in a wide variety of field crops, including [[potatoes]], [[maize|corn]] and [[soybean]]s. It is a systemic insecticide, which means that the plant absorbs it through the roots, and from here the plant distributes it throughout its organs where insecticidal concentrations are attained. Carbofuran also has contact activity against pests.


Carbofuran exhibits toxicity mediated by the same mechanism as that of the notorious [[Nerve agent#V-series|V-series nerve agents]] and presents a risk to human health. It is classified as an [[List of extremely hazardous substances|extremely hazardous substance]] in the United States as defined in Section 302 of the United States [[Emergency Planning and Community Right-to-Know Act]] (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<ref name="gov-right-know">{{Cite |publisher=[[United States Government Publishing Office|Government Printing Office]] |title=40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities |url=http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf |edition=July 1, 2008 |access-date=October 29, 2011 |archive-url=https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf |archive-date=February 25, 2012 |url-status=dead}}</ref>
Carbofuran usage has increased in recent years because it is one of the few insecticides effective on soybean [[aphid]]s, which have expanded their range since 2002 to include most soybean-growing regions of the [[United States|U.S.]] The main global producer is the FMC Corporation.


==Usage==
The technical or chemical name of carbofuran is 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate and its [[CAS number]] is 1563-66-2 and it is manufactured by reaction of [[methyl isocyanate]] with 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran.
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.<ref>{{Cite journal|last1=Sim|first1=Siong Fong|last2=Chung|first2=Ling Yan|last3=Jonip|first3=Jocephine|last4=Chai|first4=Lian Kuet|date=2019-12-23|title=Uptake and Dissipation of Carbofuran and Its Metabolite in Chinese Kale and Brinjal Cultivated Under Humid Tropic Climate|journal=Advances in Agriculture|volume=2019|pages=1–7|doi=10.1155/2019/7937086|language=en|doi-access=free}}</ref> Carbofuran acts through phloem sap against piercing-sucking pests such as green leafhoppers, brown plant hoppers, stem borers and whorl maggots.<ref>{{Cite web|title=Carbofuran - an overview {{!}} ScienceDirect Topics|url=https://www.sciencedirect.com/topics/earth-and-planetary-sciences/carbofuran|access-date=2021-06-10|website=www.sciencedirect.com}}</ref> Usage has increased in recent years because it is one of the few insecticides effective on soybean [[aphid]]s, which have expanded their range since 2002 to include most soybean-growing regions of the United States.{{cn|date=May 2022}}


==Bans==
== Chemistry ==
The technical or chemical name of carbofuran is 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate, and its [[CAS Number]] is 1563-66-2.<ref>{{Cite web |url=https://www.cdc.gov/niosh/npg/npgd0101.html |title=Carbofuran |publisher=[[National Institute for Occupational Safety and Health]] |url-status=live |archive-url=https://web.archive.org/web/20190618071305/https://www.cdc.gov/niosh/npg/npgd0101.html |archive-date=June 18, 2019 |access-date=November 13, 2019}}</ref> It is manufactured by the reaction of [[methyl isocyanate]] with 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran.<ref name="Sittig 1980 p. 145">{{cite book |last=Sittig |first=M. |title=Pesticide Manufacturing and Toxic Materials Control Encyclopedia |publisher=Noyes Data Corporation |series=Chemical Technology Review Series, Environmental Health Review Series and Pollution Technology Review Series |issue=nr. 168 |year=1980 |isbn=978-0-8155-0814-4 |url=https://books.google.com/books?id=KeA6AQAAIAAJ |access-date=September 22, 2020 |page=145}}</ref>
Carbofuran is banned in [[Canada]] and the [[European Union]].


== Toxicity ==
In 2008, the [[United States Environmental Protection Agency]] (EPA) announced that it intends to ban carbofuran.<ref>{{cite web|url=http://www.epa.gov/pesticides/reregistration/carbofuran/carbofuran_noic.htm|title=Carbofuran Cancellation Process|last=US EPA|date=July 31, 2008|publisher=US EPA|accessdate=2008-08-11}}</ref> In December of that year, [[FMC Corp.]], the sole US manufacturer of carbofuran, announced that it had voluntarily requested that the [[United States]] Environmental Protection Agency cancel all but 6 of the previously allowed uses of that chemical as a pesticide. With this change, carbofuran usage in the US would be allowed only on maize, potatoes, pumpkins, sunflowers, pine seedlings and spinach grown for seed.<ref>[[Chemical & Engineering News]], 5 January 2009, "Manufacturer drops Carbofuran uses", p. 18</ref> However, in May 2009 EPA cancelled all food tolerances, an action which amounts to a de facto ban on its use on all crops grown for human consumption.<ref>{{cite news|url=http://www.ens-newswire.com/ens/may2009/2009-05-11-093.asp|title=EPA Bans Carbofuran Pesticide Residues on Food|date=May 11, 2009|publisher=Environmental News Service|accessdate=2009-06-05}}</ref>


Carbofuran has one of the highest acute toxicities to humans of any insecticide widely used on field crops (only [[aldicarb]] and [[parathion]] are more toxic). 1 ml (1/4 teaspoon) can be fatal to humans.{{cn|date=May 2022}} 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.<ref>{{Cite journal |last1=Rehman |first1=Tanzila |last2=Khan |first2=Mohd M. |last3=Shad |first3=Muhammad A. |last4=Hussain |first4=Mazhar |last5=Oyler |first5=Benjamin L. |last6=Shad |first6=Muhammad A. |last7=Goo |first7=Young Ah. |last8=Goodlett |first8=David R. |date=September 22, 2016 |title=Detection of Carbofuran-Protein Adducts in Serum of Occupationally Exposed Pesticide Factory Workers in Pakistan |journal=Chemical Research in Toxicology |volume=29 |issue=10 |pages=1720–1728 |doi=10.1021/acs.chemrestox.6b00222 |issn=0893-228X |pmid=27657490}}</ref> Since its toxic effects are due to its activity as a [[cholinesterase]] inhibitor it is considered a [[neurotoxin|neurotoxic]] pesticide.{{citation needed|date=April 2014}} A recent study reports that carbofuran is a structural mimic of the neurohormone melatonin and could directly bind to MT2 melatonin receptor (K<sub>i</sub> = 1.7 uM).<ref>{{Cite journal |last1=Popovska-Gorevski |first1=Marina |last2=Dubocovich |first2=Margarita L. |last3=Rajnarayanan |first3=Rajendram V. |date=February 20, 2017 |title=Carbamate Insecticides Target Human Melatonin Receptors |journal=[[Chemical Research in Toxicology]] |volume=30 |issue=2 |pages=574–582 |doi=10.1021/acs.chemrestox.6b00301 |issn=0893-228X |pmc=5318275 |pmid=28027439}}</ref> Disruption of melatonin signaling could impact the circadian rhythm balance and is linked to elevated risk of developing diabetes.<ref>{{Cite web |url=https://www.niehs.nih.gov/news/newsletter/2017/3/papers/dert/index.htm |title=Extramural Papers of the Month |website=National Institute of Environmental Health Sciences |access-date=April 26, 2017}}</ref>
Kenya is considering banning carbofuran,<ref>http://www.tradingmarkets.com/.site/news/Stock%20News/2358933/</ref> but it is legal to buy [[Over-the-counter drug|over-the-counter]] in Kenya.<ref name="BBC" />


Carbofuran is highly toxic to vertebrates with an oral {{LD50}} of 8–14&nbsp;mg/kg in rats<ref name=":0" /> and 19&nbsp;mg/kg in dogs.
== Toxicity to vertebrates ==
Oral {{LD50}}: Rats 8&ndash;14 [[milligram|mg]]/[[kilogram|kg]], Dogs 19&nbsp;mg/kg.


Carbofuran is also known to be highly 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 [[United States Environmental Protection Agency‎|U.S. Environmental Protection Agency‎]] in 1991,<ref>[http://extoxnet.orst.edu/pips/carbofur.htm Extoxnet Pip - Carbofuran<!-- Bot generated title -->]</ref> 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. The EPA announced on July 25, 2008 that it intends to ban all forms in the US.<ref>[http://www.nytimes.com/2008/07/25/us/25brfs-EPATOBANUSEO_BRF.html?ref=us E.P.A. to Ban Use of a Pesticide]</ref> The ban requires that no residue be present on domestic or imported foods.<ref>[http://www.washingtonpost.com/wp-dyn/content/story/2008/07/24/ST2008072403523.html?ref=us In Surprise Move, EPA Bans Carbofuran Residue on Food.]</ref>
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 [[United States Environmental Protection Agency|EPA]] in 1991,<ref>{{cite web |url=http://extoxnet.orst.edu/pips/carbofur.htm |title=Carbofuran |access-date=September 7, 2012}}</ref> 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.{{Weasel inline|date=August 2019}}


Carbofuran has been illegally used to intentionally poison wildlife in the US, Canada and Great Britain; poisoned wildlife have included coyotes, kites, golden eagles and buzzards. Secondary fatal poisoning of domestic and wild animals has been documented,<ref>Wobeser et al. 2004. Secondary poisoning of eagles following intentional poisoning of coyotes with anticholinesterase pesticides in Western Canada. Journal of Wildlife Diseases 40(2):163-172.</ref><ref>The Federal Wildlife Officer, Volume 10, No. 2, Summer 1996</ref> specifically, [[Bird of prey|raptors]] ([[bald eagles]] and [[golden eagles]]), domestic dogs, [[raccoon]]s, [[vulture]]s and other scavengers.
Carbofuran has been illegally used to intentionally poison wildlife not only in the US, Canada and Great Britain; poisoned wildlife have included coyotes, [[Kite (bird)|kites]], golden eagles and buzzards. [[Secondary poisoning|Secondary fatal poisoning]] of domestic and wild animals has been documented,<ref>Wobeser et al. 2004. Secondary poisoning of eagles following intentional poisoning of coyotes with anticholinesterase pesticides in Western Canada. ''Journal of Wildlife Diseases'' 40(2):163-172.</ref><ref>''The Federal Wildlife Officer'', Volume 10, No. 2, Summer 1996</ref> specifically [[Bird of prey|raptors]] ([[bald eagles]] and [[golden eagles]]), domestic dogs, [[raccoon]]s, [[vulture]]s and other scavengers. In Kenya, farmers are using carbofuran to kill lions and other predators.<ref name="BBC">{{cite news |url=http://news.bbc.co.uk/2/hi/africa/7460008.stm |title=Insecticide 'killing Kenya lions' |last=Mynott |first=Adam |date=June 18, 2008 |url-status=live |archive-url=https://web.archive.org/web/20180612144113/http://news.bbc.co.uk/2/hi/africa/7460008.stm |archive-date=June 12, 2018 |work=[[BBC News]]}}</ref><ref name="cbcs" />


In a number of publicized incidents worldwide, carbofuran has also been used to poison domestic pets.<ref>{{cite news |url=http://www.cyprus-mail.com/pets/alarm-over-new-poison/20110526 |title=Alarm over new pet poison |last=Dewhurst |first=Patrick |date=May 26, 2011 |newspaper=[[Cyprus Mail]] |url-status=dead |archive-url=https://web.archive.org/web/20110528023308/http://www.cyprus-mail.com/pets/alarm-over-new-poison/20110526 |archive-date=May 28, 2011}}</ref><ref>{{cite web |url=https://www.blic.rs/vesti/beograd/psi-u-naselju-brace-jerkovic-otrovani-pesticidima/5lvv5s7 |title=Psi u naselju Braće Jerković otrovani pesticidima |last=Vušović |first=A. |date=February 25, 2011 |website=[[Blic]] |language=sr |url-status=live |archive-url=https://web.archive.org/web/20160305213717/https://www.blic.rs/vesti/beograd/psi-u-naselju-brace-jerkovic-otrovani-pesticidima/5lvv5s7 |archive-date=March 5, 2016}}</ref><ref>{{Cite news |url=https://www.news24.com/SouthAfrica/News/as-many-as-1-000-dogs-poisoned-per-week-in-sa-20190803 |title=As many as 1 000 dogs poisoned per week in SA |last=Grobler |first=Riann |date=August 3, 2019 |work=News24 |access-date=November 12, 2019 |url-status=live |archive-url=https://web.archive.org/web/20190804133538/https://www.news24.com/SouthAfrica/News/as-many-as-1-000-dogs-poisoned-per-week-in-sa-20190803 |archive-date=August 4, 2019}}</ref>
In [[Kenya]] farmers are using carbofuran to kill lions and other predators.<ref name=BBC>BBC news - [http://news.bbc.co.uk/2/hi/africa/7460008.stm Insecticide 'killing Kenya lions']</ref><ref name=CBS>CBS 60 Minutes - [http://www.cbsnews.com/stories/2009/03/26/60minutes/main4894945.shtml Poison Takes Toll on Africa's Lions]</ref>


Illegally smuggled carbofuran is used on 90% of [[marijuana]] grown illegally on public land in California.<ref>{{Cite news |url=https://apnews.com/6e7d27d687e9428381fa940ccdb0521b |title=Toxic pesticides found at most illegal California pot farms |last=Thompson |first=Don |date=August 28, 2018 |url-status=live |archive-url=https://archive.today/20191112185820/https://apnews.com/6e7d27d687e9428381fa940ccdb0521b |archive-date=November 12, 2019 |work=[[Associated Press]]}}</ref><ref>{{Cite news |url=https://www.latimes.com/environment/story/2019-08-28/cannabis-california-national-forests-environment |title=Illegal cannabis farms still scarring public lands, two years after Prop. 64 |last=McDaniel |first=Piper |date=August 29, 2019 |work=[[Los Angeles Times]] |url-status=live |archive-url=https://web.archive.org/web/20191106145816/https://www.latimes.com/environment/story/2019-08-28/cannabis-california-national-forests-environment |archive-date=November 6, 2019 |url-access=limited}}</ref><ref>{{Cite news |url=https://www.wnyc.org/story/illegal-pot-grows-in-americas-public-forests-are-poisoning-wildlife-and-water/ |title=Illegal Pot Operations in Public Forests Are Poisoning Wildlife And Water |last=Westervelt |first=Eric |date=November 12, 2019 |work=[[Morning Edition]] |access-date=November 12, 2019 |publisher=[[NPR]] |via=[[WNYC]]}}</ref> 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.<ref>{{Cite web |url=https://www.theatlantic.com/magazine/archive/2019/01/california-marijuana-crime/576391/ |title=Ending Weed Prohibition Hasn't Stopped Drug Crimes |last=Chun |first=Rene |date=January–February 2019 |website=[[The Atlantic]] |url-access=limited |url-status=live |archive-url=https://web.archive.org/web/20190530232521/https://www.theatlantic.com/magazine/archive/2019/01/california-marijuana-crime/576391/ |archive-date=May 30, 2019}}</ref>
'''Deliberate poisoning of pets: '''
It has been reported in the media <ref>http://www.cyprus-mail.com/pets/alarm-over-new-poison/20110526</ref> that carbofuran has been illegally imported into Cyprus from the occupied area and has been used to poison domestic pets.


Carbofuran is an [[endocrine disruptor]] and a probable reproduction/development intoxicant.<ref name=":0">{{Cite web |url=http://sitem.herts.ac.uk/aeru/iupac/Reports/118.htm |title=Page about Carbofuran in the IUPAC's database |website=IUPAC – International Union of Pure and Applied Chemistry |publisher=IUPAC}}</ref> At low-level exposures, carbofuran may cause transient alterations in the concentration of [[hormone]]s. These alterations may consequently lead to serious reproductive problems following repeated exposure.<ref>{{cite journal |last1=Lau |first1=TK |last2=Chu |first2=W |last3=Graham |first3=N |date=June 2007 |title=Degradation of the endocrine disruptor carbofuran by UV, O3 and O3/UV |journal=[[Water Science and Technology]] |volume=55 |issue=12 |pages=275–80 |doi=10.2166/wst.2007.416 |pmid=17674859 |doi-access=free}}</ref><ref name="pmid20021136">{{cite journal |last1=Goad |first1=Ryan T. |last2=Goad |first2=John T. |last3=Atieh |first3=Bassam H. |last4=Gupta |first4=Ramesh C. |year=2004 |title=Carbofuran-induced endocrine disruption in adult male rats |journal=[[Toxicology Mechanisms and Methods]] |volume=14 |issue=4 |pages=233–9 |doi=10.1080/15376520490434476 |pmid=20021136|s2cid=46194233 }}</ref> 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&nbsp;mg/kg dose level.<ref>{{cite journal |last1=Pant |first1=N |last2=Shankar |first2=R |last3=Srivastava |first3=SP |date=May 1997 |title=In utero and lactational exposure of carbofuran to rats: effect on testes and sperm |journal=[[Human & Experimental Toxicology]] |volume=16 |issue=5 |pages=267–72 |doi=10.1177/096032719701600506 |pmid=9192206|bibcode=1997HETox..16..267P |s2cid=26042972 }}</ref> In one study, the exposure of rats to sublethal amounts of carbofuran decreased [[testosterone]] by 88%, while the levels of [[progesterone]], [[cortisol]], and [[estradiol]] were significantly increased (1279%, 202%, and 150%, respectively).<ref name="pmid20021136" />
===Toxicity to humans===

Carbofuran has one of the highest acute toxicities to humans of any insecticide widely used on field crops (only [[aldicarb]] and [[parathion]] are more toxic). A quarter teaspoon (1 mL) can be fatal. Most carbofuran is applied by commercial applicators using closed systems with engineered controls so there is no exposure to it in preparation. Since its toxic effects are due to its activity as a [[cholinesterase]] inhibitor it is considered a [[neurotoxin|neurotoxic]] pesticide.
== Bans ==
Carbofuran is banned in [[Canada]], [[Sri Lanka]] and the [[European Union]].<ref>UNEP/FAO/RC/CRC/11/6 section 2.2.3 of the European Union notification</ref>

In 2008, the [[United States Environmental Protection Agency]] (EPA) announced that it intended to ban carbofuran.<ref>{{cite web |url=http://www.epa.gov/pesticides/reregistration/carbofuran/carbofuran_noic.htm |title=Carbofuran Cancellation Process |last=US EPA |date=July 31, 2008 |publisher=US EPA |access-date=August 11, 2008}}</ref> In December of that year, [[FMC Corp.]], 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.<ref>{{Cite magazine |last=Erickson |first=Britt E. |date=January 5, 2009 |title=Manufacturer Drops Carbofuran Uses |url=https://cen.acs.org/articles/87/i1/Manufacturer-Drops-Carbofuran-Uses.html |magazine=[[Chemical & Engineering News]] |volume=87 |issue=1 |page=18 |archive-url=https://archive.today/20191112182500/https://cen.acs.org/articles/87/i1/Manufacturer-Drops-Carbofuran-Uses.html |archive-date=November 12, 2019 |access-date=November 12, 2019 |url-status=live}}</ref> 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.<ref>{{cite news |url=http://www.ens-newswire.com/ens/may2009/2009-05-11-093.asp |title=EPA Bans Carbofuran Pesticide Residues on Food |date=May 11, 2009 |publisher=Environmental News Service |access-date=June 5, 2009}}</ref>

[[Kenya]] is considering banning carbofuran,<ref>{{cite web |url=http://www.tradingmarkets.com/.site/news/Stock%20News/2358933/ |archive-url=https://archive.today/20120629152217/http://www.tradingmarkets.com/.site/news/Stock%20News/2358933/ |url-status=dead |archive-date=June 29, 2012 |title=unknown |publisher=tradingmarkets.com}}</ref> but it is legal to buy [[Over-the-counter drug|over-the-counter]] in Kenya.<ref name="BBC" />

=== Health scare in Thailand ===
Due to nonregistration of 4 [[carcinogenic]] chemicals used on crops not listed in the [[Dangerous Substances Act]] of [[Thailand]], vegetables with residues of [[methomyl]], carbofuran, [[dicrotophos]], and [[EPN (insecticide)|EPN]] were taken off supermarket shelves in July 2012.<ref>{{cite news |url=https://www.bangkokpost.com/thailand/politics/302017/cancer-causing-chemical-residues-found-in-vegetables |title=Cancer-causing chemical residues found in vegetables |date=July 12, 2012 |newspaper=[[Bangkok Post]] |access-date=September 7, 2012 |url-status=live |archive-url=https://archive.today/20191112183846/https://www.bangkokpost.com/thailand/politics/302017/cancer-causing-chemical-residues-found-in-vegetables |archive-date=November 12, 2019}}</ref>

=== Death of lions in Kenya ===
In 2009, the [[CBS]] television news magazine ''[[60 Minutes]]'' 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.<ref name="cbcs">{{cite news |url=https://www.cbsnews.com/news/poison-takes-toll-on-africas-lions/ |title=Poison Takes Toll On Africa's Lions |date=March 26, 2009 |work=[[60 Minutes]] |url-status=live |archive-url=https://web.archive.org/web/20180613014617/https://www.cbsnews.com/news/poison-takes-toll-on-africas-lions/ |archive-date=June 13, 2018 |publisher=[[CBS News]]}}</ref> FMC has commented on this issue through the media and their websites including furadanfacts.com.<ref>{{cite web |url=http://furadanfacts.com/ |title=Furadan Facts > Home |access-date=May 8, 2016 |archive-url=https://web.archive.org/web/20160503212720/http://www.furadanfacts.com/ |archive-date=May 3, 2016 |url-status=dead}}</ref> 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.<ref>{{cite news |url=https://usatoday30.usatoday.com/news/nation/states/pennsylvania/2009-03-29-2296664908_x.htm |title=Pa. pesticide maker vows steps to protect lions |last=Todt |first=Ron |date=March 29, 2009 |work=[[USA Today]] |url-status=live |archive-url=https://web.archive.org/web/20160512102458/https://usatoday30.usatoday.com/news/nation/states/pennsylvania/2009-03-29-2296664908_x.htm |archive-date=May 12, 2016 |agency=[[Associated Press]]}}</ref><ref>{{cite web |url=http://www.furadanfacts.com/ |title=Furadan Facts > Home |access-date=March 30, 2009 |archive-url=https://web.archive.org/web/20140317004850/http://www.furadanfacts.com/ |archive-date=March 17, 2014 |url-status=dead}}</ref> Despite this, however, National Geographic stated in 2018 that carbofuran "is still very much available" in Kenya.<ref>{{Cite web |url=https://www.nationalgeographic.com/magazine/2018/08/poisoning-africa-kenya-maasai-pesticides-lions-poachers-conservationists/ |archive-url=https://web.archive.org/web/20180804090157/https://www.nationalgeographic.com/magazine/2018/08/poisoning-africa-kenya-maasai-pesticides-lions-poachers-conservationists/ |url-status=dead |archive-date=August 4, 2018 |title=Why Poison Is a Growing Threat to Africa's Wildlife |last=Dobb |first=Edwin |date=August 2018 |website=[[National Geographic]] |others=Photographs by Charlie Hamilton James |access-date=November 12, 2018}}</ref>


== See also ==
== See also ==
Line 127: Line 112:


== References ==
== References ==
{{reflist}}
{{reflist|30em}}


==External links==
==External links==
{{Commons category}}
*[http://www.furadanfacts.com/ FuradanFacts.com]
*[https://www.annapoliscreative.com/the-carbo-wars/ The 'Carbo Wars' – the intentional poisoning of eagles and other wildlife in Maryland]
*[https://www.washingtonpost.com/news/animalia/wp/2018/06/20/thirteen-bald-eagles-were-found-dead-in-a-field-this-is-what-killed-them/ Washington Post: Thirteen bald eagles were found dead this is what killed them]
*[http://www.karbofuran.cz/ Website devoted to raising the awareness about the use of carbofuran to kill wild animals]
*[http://www.otterspecialistgroup.org/Bulletin/Volume27/Polednikova_et_al_2010.pdf CARBOFURAN – A NEW AND EFFECTIVE METHOD OF ILLEGAL KILLING OF OTTERS (Lutra lutra) IN THE CZECH REPUBLIC]
*[https://web.archive.org/web/20140317004850/http://www.furadanfacts.com/ FuradanFacts.com]
*[https://www.cdc.gov/niosh/npg/npgd0101.html CDC – NIOSH Pocket Guide to Chemical Hazards – Carbofuran]


{{insecticides}}
{{Insecticides}}
{{Acetylcholine metabolism and transport modulators}}
{{Cholinergics}}


[[Category:Acetylcholinesterase inhibitors]]
[[Category:Carbamate insecticides]]
[[Category:Carbamate insecticides]]
[[Category:Anticholinesterases]]
[[Category:Benzofuran ethers at the benzene ring]]
[[Category:Benzofurans]]
[[Category:Catechol ethers]]
[[Category:Phenol ethers]]
[[Category:Phenol esters]]
[[Category:Insecticides]]

[[Category:Female reproductive toxicants]]
[[cs:Karbofuran]]
[[Category:Aromatic carbamates]]
[[de:Carbofuran]]
[[es:Carbofurano]]
[[fr:Carbofuran]]
[[nl:Carbofuran]]
[[ro:Carbofuran]]
[[th:คาร์โบฟูแรน]]
[[uk:Карбофуран]]
[[ml:ഫ്യുറഡാൻ]]