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;
Identifiers
CAS Number	63114-77-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	143082 ;
PubChem CID	162992;
UNII	9J19F5321S;
CompTox Dashboard (EPA)	DTXSID2042513 ;
	InChI 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;
	SMILES CC1=C(C(=CC=C1)N(C(C)C)C(=O)CCl)C;
Properties
Chemical formula	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). Infobox references

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. Prediction software indicates that it may be a class 3 highly toxic compound, mutagen or carcinogen, although other software predictions disagree.^[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

^ ^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.
^ ^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.
^ "COMBAT Trademark - Registration Number 1123574 - Serial Number 73174544 :: Justia Trademarks". trademarks.justia.com. Retrieved 1 March 2025.
^ 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]}
^ 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.
^ 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.

Links

Xylachlor in the Pesticide Properties DataBase (PPDB)

[techrep57-1] "TECHNICAL REPORT No.5: THEACTIVITYANDPRE-EMERGENCESELECTIVITYOFSOMERECENTLYDEVELOPEDHERBICIDES:R40244,AC206784,PENDIMETHALIN,BUTRALIN,ACIFLUORFENANDFMC39821". BCPC British Crop Production Council. December 1979. Retrieved 30 November 2025.

[Lewis_Tzilivakis_international_database-2] 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.

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