Karbutilate

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Contents

Karbutilate
Karbutilate.svg
Names
Preferred IUPAC name
[3-(dimethylcarbamoylamino)phenyl] N-tert-butylcarbamate
Other names
  • karbutylate
  • tanzine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.023.126 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 225-439-7
PubChem CID
UNII
  • InChI=1S/C14H21N3O3/c1-14(2,3)16-13(19)20-11-8-6-7-10(9-11)15-12(18)17(4)5/h6-9H,1-5H3,(H,15,18)(H,16,19)
    Key: UQVYUTAMNICZNI-UHFFFAOYSA-N
  • CC(C)(C)NC(=O)OC1=CC=CC(=C1)NC(=O)N(C)C
Properties
C14H21N3O3
Molar mass 279.340 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H319, H400
P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Karbutilate is a post- and pre-emergent herbicide. It is a carbamate ester and substituted urea, [1] and its formula is C14H21N3O3. [2] After a 4-year development period, it was first sold in 1968, marketed under the name Tandex. [3]

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 [4] and is marked as obsolete. [5]

Uses

Karbutilate acts as an herbicide on broad-leaf plants by inhibiting photosynthesis. [6]

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. [7]

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]

References

  1. 1 2 "Karbutilate (T3D0978)". Toxin and Toxin Target Database. Retrieved December 2, 2024.
  2. 1 2 "Karbutilate". PubChem . National Center for Biotechnology Information . Retrieved December 2, 2024.
  3. 1 2 "New Broad Spectrum Herbicide" (PDF). Weeds Trees and Turf. October 1968. Retrieved December 2, 2024.
  4. ↑ "Active substance: Karbutilate". EU Pesticides Database. Retrieved December 2, 2024.
  5. ↑ "Karbutilate". AgData. Retrieved December 2, 2024.
  6. ↑ Hammerschlag RS, Hilton JL, Bartels PG, Moreland DE (1975). "Contribution of Side Chains to Karbutilate Mode of Action" . Weed Science. 23 (5): 425–427. doi:10.1017/S0043174500062809. ISSN   0043-1745. JSTOR   4042351.
  7. ↑ Amorim C, Albert-García J, Montenegro M, Araújo A, Calatayud JM (January 2007). "Photo-induced chemiluminometric determination of Karbutilate in a continuous-flow Multicommutation assembly" . Journal of Pharmaceutical and Biomedical Analysis. 43 (2): 421–427. doi:10.1016/j.jpba.2006.07.006. PMID   16930910.
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