Langbahn Team – Weltmeisterschaft

Xylachlor

Xylachlor
Names
Preferred IUPAC name
2-chloro-N-(2,3-dimethylphenyl)-N-propan-2-ylacetamide
Other names
  • 2-chloro-N-(2-chloro-N-isopropylacet-2,3-xylidide
  • 2-chloro-N-(2,3-dimethylphenyl)-N-(1-methylethyl)acetamide
  • xylachlore
  • CL 206784
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H18ClNO/c1-9(2)15(13(16)8-14)12-7-5-6-10(3)11(12)4/h5-7,9H,8H2,1-4H3
    Key: UDRNNGBAXFCBLJ-UHFFFAOYSA-N
  • CC1=C(C(=CC=C1)N(C(C)C)C(=O)CCl)C
Properties
C13H18ClNO
Molar mass 239.74 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Xylachlor is a selective herbicide, used to pre-emergently control annual grasses on cereals, wheat, soy and rice. It is an anilide and a (chloro)acetanilide. As of 2023 it is considered obsolete, but may still be in use.[1]

It was manufactured by American Cyanamid under the "Combat" trademark,[1] registered in August 1979 and expired (by non-renewal) in 1986.[2]

Compared to the fellow acetanilides alachlor, acetochlor and metolachlor, xylachlor had the weakest control of pigweed and setaria, though the greatest selectivity.[3] Xylachlor is also less detrimental to sorghum, but this is offset by the need for higher application rates to achieve similar weed control.[4]

Xylachlor's safety is not well studied. Prediction software indicates that it may be a class 3 highly toxic compound, mutagen or carcinogen, although other software predictions disagree.[5]

References

  1. ^ a b Lewis, Kathleen A.; Tzilivakis, John; Warner, Douglas J.; Green, Andrew (18 May 2016). "An international database for pesticide risk assessments and management". Human and Ecological Risk Assessment: An International Journal. 22 (4): 1050–1064. Bibcode:2016HERA...22.1050L. doi:10.1080/10807039.2015.1133242. hdl:2299/17565.
  2. ^ "COMBAT Trademark - Registration Number 1123574 - Serial Number 73174544 :: Justia Trademarks". trademarks.justia.com. Retrieved 1 March 2025.
  3. ^ Owen, M. D. K. (1982). A Comparison Of The Herbicidal Activity Of Several Chloroacetamides And Their Effects On Protein Synthesis In Carrot And Soybean Cell Suspension Cultures (Thesis). ProQuest 303227220.[page needed]
  4. ^ Simkins, G. S.; Moshier, L. J.; Russ, O. G. (1980). "Influence of Acetamide Herbicide Applications on Efficacy of the Protectant CGA-43089 in Grain Sorghum (Sorghum bicolor)". Weed Science. 28 (6): 646–649. doi:10.1017/S0043174500061427. JSTOR 4043438.
  5. ^ Berber, Ahmet Ali; Demi̇R, Şefika Nur; Akinci KenanoğLu, Nihan (25 August 2023). "Potential Health Risks of Chloroacetanilide Herbicides: An In Silico Analysis". Sakarya University Journal of Science. 27 (4): 865–871. doi:10.16984/saufenbilder.1281720.
  • Xylachlor in the Pesticide Properties DataBase (PPDB)
Quelle: https://en.wikipedia.org/wiki/Xylachlor