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; AC 206784[1]
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 preëmergently 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.[2]

It was manufactured by American Cyanamid under the "Combat" trademark,[2] registered in August 1979 and expired (by non-renewal) in 1986.[3]

Compared to the fellow acetanilides alachlor, acetochlor and metolachlor, xylachlor had the weakest control of pigweed and setaria, though the greatest selectivity.[4] Xylachlor is also less detrimental to sorghum, but this is offset by the need for higher application rates to achieve similar weed control.[5] It controlled annual grasses and some broadleaf weeds, and uis generally less active than pendimethalin.[1]

Xylachlor's safety is not well studied. It and the related delachlor could be toxic, or carcinogen; some software prediction programs say so (ToxTree, Vega Hub) and some disagree. (Lazar and TEST)[6]

Application

It has been formulated as a 48% w/v emulsifiable concentrate, which was in a 1979 test, applied at 2.0-6.0 kg/Ha of active ingredient, in 400 L/Ha of spray water.[1]

Application Rate Effects[1]
Application Rate Crops tolerant Weeds controlled
4 kg/Ha wheat, pea, rape, kale, radish, cowpea, chickpea, groundnut, soyabeen, cotton, kenaf bromus sterilis (barren brome), avena fatua (common wild oat), alopecurus myosuroides (blackgrass / twitchgrass), senecio vulgaris (groundsel), veronica persica (speedwell), phalaris minor (small canary-grass)
1 kg/Ha barley, field bean, carrot, sugar beet, maize, sorghum (with antidote), tomato poa annua (annual bluegrass), poa trivialis (rough bluegrass / meadowgrass), oryza punctata (red rice), echinochloa crus-galli (cockspur / barnyardgrass), digitaria sanguinalis (crabgrass), amaranthus retroflexus (common tumbleweed)
0.25 kg/Ha oat, onion, lettuce, sorghum, pigeon pea, sesamum Holcus lanatus (Yorkshire fog/meadow soft grass), Eleusine indica (goosegrass), Snowdenia polystachya

In that table, 'tolerant' means the crop's vigour was reduced by less than 15%, and 'controlled' means the weed's vigour or number was reduced by more than 70%.

References

  1. ^ a b c d "TECHNICAL REPORT No.5: THEACTIVITYANDPRE-EMERGENCESELECTIVITYOFSOMERECENTLYDEVELOPEDHERBICIDES:R40244,AC206784,PENDIMETHALIN,BUTRALIN,ACIFLUORFENANDFMC39821". BCPC British Crop Production Council. December 1979. Retrieved 30 November 2025.
  2. ^ 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. 22 (4): 1050–1064. Bibcode:2016HERA...22.1050L. doi:10.1080/10807039.2015.1133242. hdl:2299/17565.
  3. ^ "COMBAT Trademark - Registration Number 1123574 - Serial Number 73174544 :: Justia Trademarks". trademarks.justia.com. Retrieved 1 March 2025.
  4. ^ 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]
  5. ^ 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.
  6. ^ 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)

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