Karsil

Karsil
Names
Preferred IUPAC name
N-(3,4-Dichlorophenyl)-2-methylpentanamide
Other names
  • (2RS)-3′,4′-Dichloro-2-methylpentananilide
  • (RS)-3′,4′-Dichloro-2-methylvaleranilide
  • N-(3,4-Dichlorophenyl)-2-methylpentanamide[1]
  • NIA 4562
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C12H15Cl2NO/c1-3-4-8(2)12(16)15-9-5-6-10(13)11(14)7-9/h5-8H,3-4H2,1-2H3,(H,15,16)
    Key: VUNCGGHZBFQRPB-UHFFFAOYSA-N
  • CCCC(C)C(=O)NC1=CC(=C(C=C1)Cl)Cl
Properties
C12H15Cl2NO
Molar mass 260.16 g·mol−1
Density 1222 kg/m3[2]
Melting point 106 °C (223 °F; 379 K)[2]
Boiling point 396[2] °C (745 °F; 669 K)
Vapor pressure 1.79 nmHg[2]
Hazards
Flash point 193[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Karsil (also called erlüjixiancaoan) is an acylanilide herbicide, similar to propanil. It is potent against annual grasses and broadleaved weeds in celery, and a strong inhibitor of photosynthesis.[3] It is approved for use in China.[1]

When degraded by bacteria, karsil becomes 3,4-dichloroaniline and 3,3',4,4,'-tetrachloroazobenzene.[3] Karsil is theorised to form hydrogen bonds with the protein of an enzyme involved in the oxidation of water, creating its herbicidal potential, similar to diuron and atrazine.[4]

Karsil has been manufactured by Niagara Chemical Division.[5] If ingested, activated charcoal absorbs it.[6] Karsil is ten times as active as atrazine at the chloroplast level.[7]

References

  1. ^ a b "erlujixiancaoan data sheet". bcpcpesticidecompendium.org.
  2. ^ a b c d e "Buy erlujixiancaoan from HANGZHOU JHECHEM CO LTD". ECHEMI.
  3. ^ a b Sharabi, Nagim El-Din; Bordeleau, Lucien M. (September 1969). "Biochemical Decomposition of the Herbicide N-(3,4-Dichlorophenyl)-2-Methylpentanamide and Related Compounds". Applied Microbiology. 18 (3): 369–375. doi:10.1128/am.18.3.369-375.1969. PMC 377987. PMID 5373674.
  4. ^ van Overbeek, J. (1962). "Physiological Responses of Plants to Herbicides". Weeds. 10 (3): 170–174. doi:10.2307/4040775. JSTOR 4040775.
  5. ^ Wallnöfer, P. R.; Safe, S.; Hutzinger, O. (1 July 1972). "Die hydroxylation des herbizids karsil (N-(3,4-Dichlorophenyl)-2-methylpentanamid) durch Rhizopusjaponicus". Chemosphere. 1 (4): 155–158. doi:10.1016/0045-6535(72)90019-7.
  6. ^ "Analytical reference standards and supplemental data for pesticides and other organic compounds". nepis.epa.gov. January 1981.
  7. ^ Masatoshi, Ghobara; Duke, Stephen O.; Takematsu, Tetsuo (August 26, 1987). "MT-5950, a New Anilide Herbicide, Inhibits PSII at a Site that Slightly Overlaps the Triazine Binding Site". Agric. Biol. Chem.: 465–472. Retrieved 15 March 2025.
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