:Carbendazim
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443497642
| Name =
| Reference = Merck Index, 11th Edition, 1794.
| ImageFile = Carbendazim Structural Formulae V.1.svg
| ImageSize =
| PIN = Methyl (1H-1,3-benzimidazol-2-yl)carbamate
| OtherNames = Mercarzole
Carbendazole
| SystematicName =
| Section1 = {{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 23741
| InChIKey = TWFZGCMQGLPBSX-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TWFZGCMQGLPBSX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 10605-21-7
| ChEBI = 3392
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 70971
| EINECS =
| PubChem = 25429
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H75J14AA89
| SMILES = COC(=O)Nc2nc1ccccc1[nH]2
| InChI = 1/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13)
| RTECS = DD6500000
| MeSHName =
| ChEBI_Ref = {{ebicite|changed|EBI}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10897
}}
| Section2 = {{Chembox Properties
| C=9 | H=9 | N=3 | O=2
| MolarMass = 191.187 g/mol
| Appearance = White to light gray powder
| Density = 1.45 g/cm3
| MeltingPtC = 302 to 307
| MeltingPt_notes = (decomposes)
| BoilingPt =
| BoilingPt_notes =
| Solubility = 8 mg/L
Disintegration = 302 -305 degree
Temperature of disintegration = 1.5 - 2 hrs
| SolubleOther =
| Solvent = acetone
| pKa = 4.48
| pKb =
}}
| Section3 =
| Section4 =
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL =
Disintegration temp = 302 - 305 degree
Disintegration temp = 1.5 - 2 hrs
}}
}}
Carbendazim is a fungicide, a member benzimidazole fungicides. It is a metabolite of benomyl.{{cite book |doi=10.1002/0471238961.0621140704180509.a01 |chapter=Fungicides, Agricultural |title=Kirk-Othmer Encyclopedia of Chemical Technology |date=2000 |last1=Dreikorn |first1=Barry A. |last2=Owen |first2=W. John |isbn=978-0-471-48494-3 }}
The fungicide is used to control plant diseases in cereals and fruits, including citrus, bananas, strawberries, macadamia nuts, pineapples, and pomes.{{cite news |last=Wight |first=Andrew |title=Two-headed fish mystery deepens |url=http://sl.farmonline.com.au/news/nationalrural/agribusiness-and-general/general/twoheaded-fish-mystery-deepens/1406893.aspx?storypage=0 |newspaper=Stock & Land |date=14 January 2009 |archive-url=https://web.archive.org/web/20091019215853/http://sl.farmonline.com.au/news/nationalrural/agribusiness-and-general/general/twoheaded-fish-mystery-deepens/1406893.aspx?storypage=0 |archive-date=19 October 2009 |url-status=dead }} A 4.7% solution of carbendazim hydrochloride, sold as Eertavas, is marketed as a treatment for Dutch elm disease.{{cite news
| url=http://www.smh.com.au/news/environment/fungicide-maker-in-birth-defect-storm/2009/02/02/1233423096718.html|title=Fungicide maker in birth defect storm|publisher=Sydney Morning Herald|date=2009-02-02|access-date=2010-03-21|author=Marissa Calligeros}}
Other uses
It is also employed as a casting worm control agent in amenity turf situations such as golf greens, tennis courts etc. and in some countries is licensed for that use only.{{cite news|title=Getting the best worm control|url=http://www.sherriffamenity.com/technicalupdates/Getting-The-Best-Worm-Control/90/}}
Safety, regulation, controversy
High doses of carbendazim destroy the testicles of laboratory animals.{{cite journal|last=Aire|first=TA|title=Short-term effects of carbendazim on the gross and microscopic features of the testes of Japanese quails (Coturnix coturnix japonica).|journal=Anatomy and Embryology|date=August 2005|volume=210|issue=1|pages=43–9|pmid=16034611|doi=10.1007/s00429-005-0001-0|s2cid=8526462}}{{cite news|title=Carbendazim use banned on fruit crops|url=http://www.abc.net.au/rural/news/content/201002/s2811428.htm|newspaper=ABC|date=5 February 2010}}
Maximum pesticide residue limits (MRLs) for fresh produce in the EU are between 0.1 and 0.7 mg/kg with the exception of loquat fruits, which is set at 2 mg/kg.{{cite web|title=EU Pesticides Database|url=http://ec.europa.eu/sanco_pesticides/public/index.cfm|access-date=24 February 2012}} The limits for more commonly consumed citrus and pome fruits are between 0.1 and 0.2 mg/kg.
Use of this fungicide on macadamia plantations has proven controversial in Queensland.
References
{{Reflist}}
External links
- {{Commons category-inline}}
- [https://www.cdc.gov/niosh/ipcsneng/neng1277.html International Chemical Safety Card]
- {{PPDB|116}}
{{Acetylcholine metabolism and transport modulators}}