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Tralkoxydim

Tralkoxydim
Names
IUPAC name
(RS)-2-[(EZ)-1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one
Preferred IUPAC name
(5E)-2-[(1E)-N-ethoxypropanimidoyl]-3-hydroxy-5-(2,4,6-trimethylphenyl)cyclohex-2-en-1-one
Other names
  • tralkoxydime
  • tralcoxidime
  • 2-(1-(ethoxyimino)propyl)-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-1-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 618-075-9
KEGG
UNII
  • InChI=1S/C20H27NO3/c1-6-16(21-24-7-2)20-17(22)10-15(11-18(20)23)19-13(4)8-12(3)9-14(19)5/h8-9,15,22H,6-7,10-11H2,1-5H3
    Key: DQFPEYARZIQXRM-UHFFFAOYSA-N
  • CCC(=C1C(=O)CC(CC1=O)C2=C(C=C(C=C2C)C)C)NOCC
Properties
C20H27NO3
Molar mass 329.440 g·mol−1
Appearance White solid[1]
Density 1160 kg/cu.m[1][dubious – discuss]
Melting point 110 °C (230 °F; 383 K) [1]
6.1 mg/L[1]
Solubility in acetone 89 g/L[1]
Solubility in methanol 25 g/L[1]
Solubility in toluene 213 g/L[1]
Solubility in ethyl acetate 110 g/L[1]
Hazards
GHS labelling:[2][1]
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H302, H411
P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, P501
Lethal dose or concentration (LD, LC):
  • 6200 mg/kg (quail, oral)
  • 1100 mg/kg (mouse, oral)
  • >2000 mg/kg (rat, dermal)[2]
  • 3.5 mg/L (rat, inhalation, 4 hours)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tralkoxydim is a herbicidal chemical used in Australia and Canada postemergently to control annual ryegrass, wild oats, barnyard grass, foxtail and persian darnel in wheat, barley, rye, triticale and fodder,[3][4][1] though it has no effect on broadleaf weeds. It was banned in the EU in 2019.[5]

Tralkoxydim came out of Dow Agrosciences's patent in Canada circa 2009.[6] It was first registered in Australia circa 1990.[7]

Mechanism of action

Tralkoxydim's HRAC classification is Group A (Australia and global) or Group 1 (numeric).[3] Group A herbicides inhibit acetyl-CoA carboxylase (ACCase).

Tralkoxydim is absorbed by the weeds' leaves, thence moved through phloem to growing plantmatter where it inhibits the enzyme ACCase, which is needed for fatty acid synthesis. Hence tralkoxydim stops cell division and damages cell membranes, stopping the weed's growth nearly immediately.[5]

Weeds affected by tralkoxydim show symptoms after 7 to 10 days, with purpling and yellowing shoots, and necrosis, and after 3 to 4 weeks, death.[3]

Resistance has developed in some weeds in Western Australia,[3] in about 10% of sampled wild oat populations.[8]

Application

Tralkoxydim is rainfast after 30 minutes or an hour. It is often supposed to be used with an adjuvant, at perhaps 0.5-1% of spray volume,[4][3] and one such adjuvant is 50% mineral oil and 40% mixed surfactants.[9] Crop injury can occur to non-tilled barley if temperatures fall below 40°F (4°C) within a couple of days before or after application, or if the crops are already stressed because of heat, drought or other reasons.[10]

Tralkoxydim can be applied via ground equipment, at 300 to 500 grams per hectare (0.27 to 0.45 lb per acre) in a spray volume of 50 to 150 litres of water per hectare (5 to 16 gallons per acre); or by aerial application at 20 to 30 L/Ha (2.1 to 3.2 gal/Ha).[11]

Tralkoxydim has been sold under the tradenames "Achieve", (Crop Care),[12][3] Bison, (Adama),[13] "Traction", (Tangyun),[14] and "Tralkoxydim" (Apparent,[15] 4Farmers,[16] Nufarm,[4] Smart).[17]

Safety

Tralkoxydim's acceptable daily intake is set by the EU at 0.005 mg per kg bodyweight per day, and the EU marks it with the GHS hazard statement No 351, "Suspected of causing cancer",[5] though this statement is absent in safety data sheets from Canada or Australia.[2][18]

Ecological information

Tralkoxydim is not toxic to birds or bees. It may be toxic to aquatic life including algae (LC50 >5.1 mg/L), bluegill (LC50 >6.1 mg/L), and rainbow trout (LC50 >7.2 mg/L). Its average field half-life is about 2 to 13 days in aerobic conditions, but the water and soil persistence is high. It has low bioacculumative potential, and medium mobility in soil.[2]

References

  1. ^ a b c d e f g h i Hertfordshire, University of. "Tralkoxydim (Ref: PP 604)". sitem.herts.ac.uk. Retrieved 23 August 2026.
  2. ^ a b c d e "4Farmers Tralkoxydim 400 WG Safety Data Sheet" (PDF). 4Farmers Australia. 20 July 2021. Retrieved 23 August 2026.
  3. ^ a b c d e f "4Farmers Tralkoxydim 400 WG Infosheet" (PDF). 4Farmers Australia. Retrieved 23 August 2026.
  4. ^ a b c "Nufarm Canada | Tralkoxydim | Herbicide | Crop Protection". Nufarm Canada. Retrieved 23 August 2026.
  5. ^ a b c "Tralkoxydim: Selective Herbicide for Grass Weed Control". Agronom.info.
  6. ^ "Off-patent weed killer targets Liquid Achieve | Grainews". Grainews. GFM Network News. 23 February 2009.
  7. ^ Madin, R. W.; Martin, R. J. (August 1990). "The Effect of Timing and Rate of Application of Tralkoxydim on Wild Oat and Ryegrass Control and Crop Tolerance in Wheat" (PDF). Proceedings of the Australian Weeds Conference. Adelaide, South Australia.
  8. ^ Owen, Mechelle; Beckie, Hugh (15 April 2020). "Update on herbicide resistance status in the Western Australian wheatbelt". Grains Research and Development Corporation.
  9. ^ "Carrier Emulsifiable Concentrate Label" (PDF). Nufarm Canada. Retrieved 23 August 2026.
  10. ^ Menalled, Fabian (11 June 2004). "Preventing Herbicide Injuries in Barley". Montana State University. Retrieved 23 August 2026.
  11. ^ "4Farmers Tralkoxydim 400 WG Leaflet" (PDF). www.4farmers.com.au. 4Farmers Australia. Retrieved 23 August 2026.
  12. ^ "Achieve WG - Crop Care Australasia Herbicides". agrobaseapp.com. Retrieved 23 August 2026.
  13. ^ "BISON® 400 L". ADAMA West Canada. Retrieved 23 August 2026.
  14. ^ "Tralkoxydim". https://www.tangagri.com/. Retrieved 23 August 2026. {{cite web}}: External link in |website= (help)
  15. ^ "Apparent Tralkoxydim 5kg Active: 400g/kg Tralkoxydim". www.fmb.com.au. Retrieved 23 August 2026.
  16. ^ "4Farmers Tralkoxydim 400 WDG". 4Farmers Australia. Retrieved 23 August 2026.
  17. ^ "Smart Tralkoxydim | Herbicide | Control Ryegraass". Crop Smart Pty Ltd. Retrieved 23 August 2026.
  18. ^ "Nufarm Tralkoxydim Liquid Safety Data Sheet" (PDF). Nufarm Canada. 21 December 2017.
  • Tralkoxydim in the Pesticide Properties DataBase (PPDB)

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