Xylachlor

Xylachlor
Names
	Preferred IUPAC name 2-chloro-N-(2,3-dimethylphenyl)-N-propan-2-ylacetamide
	Other names 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.

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

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

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)

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.

Application Rate Effects
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 2 3 4 "TECHNICAL REPORT No.5: THEACTIVITYANDPRE-EMERGENCESELECTIVITYOFSOMERECENTLYDEVELOPEDHERBICIDES:R40244,AC206784,PENDIMETHALIN,BUTRALIN,ACIFLUORFENANDFMC39821". BCPC British Crop Production Council. December 1979. Retrieved 30 November 2025.
1 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.
↑ "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. hdl:20.500.12428/14868.

Links

Xylachlor in the Pesticide Properties DataBase (PPDB)

[techrep57-1] 1 2 3 4 "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] 1 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. hdl:20.500.12428/14868.