Chemistry:Karbutilate
Karbutilate is a post- and pre-emergent herbicide. It is a carbamate ester and substituted urea,[1] and its formula is C
14H
21N
3O
3.[2] After a 4-year development period, it was first sold in 1968, marketed under the name Tandex.[3] It controls annual broadleaf weeds, grasses and vines, and is used in non-crop scenarios like drainage ditches and industrial sites.[4]
History
Karbutilate is a derivative of carbamic acid, and is of the class of carbamate pesticides developed following the introduction of carbaryl in 1956.[2] It was developed by the Niagara Chemical Division of FMC Corporation from 1964 to 1968, and made its debut under the name Tandex.[3] It is currently not classified by or approved for use by the European Union, as its registration has expired[5] and is marked as obsolete,[6] though in 2015 it was reportedly registered in the USA.[4]
Uses
Karbutilate acts as an herbicide on broad-leaf plants by inhibiting photosynthesis.[7]
Karbutilate has been investigated, alongside other carbamate pesticides, as having a potential cleanup route by photodegradation in the case of accidental spill or other unwanted environmental exposure. Irradiation by ultraviolet light has been noted as primarily causing the cleavage of the ester bond in carbamate esters.[8]Pesticide formulations of karbutilate are usually granules (GR) or wettable powders (WP).[4]
Toxicity
Though carbamate pesticides are broadly used due to their low oral and dermal toxicity to mammals, karbutilate poses a potential hazard to humans as a cholinesterase inhibitor. It is also potentially hazardous to Hymenopterans.[1] It is non-toxic to wildlife and fish, though might be a mild skin irritant and/or harmful if ingested, so an ADI is set at 0.005 mg/kg bodyweight per day,[4] equalling 0.4 mg/kg/day for an 80 kg adult.
References
- ↑ 1.0 1.1 "Karbutilate (T3D0978)". http://www.t3db.ca/toxins/T3D0978.
- ↑ 2.0 2.1 Template:Cite PubChem
- ↑ 3.0 3.1 "New Broad Spectrum Herbicide". Weeds Trees and Turf. October 1968. https://archive.lib.msu.edu/tic/wetrt/article/1968oct16.pdf. Retrieved 2 December 2024.
- ↑ 4.0 4.1 4.2 4.3 Cite error: Invalid
<ref>tag; no text was provided for refs namedtpe - ↑ "Active substance: Karbutilate". https://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/start/screen/active-substances/details/252.
- ↑ "Karbutilate". https://www.agropages.com/AgroData/Detail-848.htm#summary.
- ↑ Hammerschlag, R. S.; Hilton, J. L.; Bartels, P. G.; Moreland, D. E. (1975). "Contribution of Side Chains to Karbutilate Mode of Action". Weed Science 23 (5): 425–427. doi:10.1017/S0043174500062809. ISSN 0043-1745. https://www.jstor.org/stable/4042351.
- ↑ Amorim, C.M.P.G.; Albert-García, J.R.; Montenegro, M.C.B.S.; Araújo, A.N.; Calatayud, J. Martínez (January 2007). "Photo-induced chemiluminometric determination of Karbutilate in a continuous-flow Multicommutation assembly" (in en). Journal of Pharmaceutical and Biomedical Analysis 43 (2): 421–427. doi:10.1016/j.jpba.2006.07.006. PMID 16930910. https://linkinghub.elsevier.com/retrieve/pii/S0731708506004523.
Links
- Karbutilate in the Pesticide Properties DataBase (PPDB)
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