Cynmethylin

Cynmethylin
Names
Preferred IUPAC name
rac-(1R,2S,4S)-1-methyl-2-[(2-methylphenyl)methoxy]-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane
Other names
  • WL 95481
  • SD 95481
  • rac-(1R,2S,4S)-1-methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-7-oxabicyclo[2.2.1]heptane
  • rel-(1R,2S,4S)-1-methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-7-oxabicyclo[2.2.1]heptan
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.100.423 Edit this at Wikidata
EC Number
  • 402-410-9
KEGG
UNII
  • InChI=1S/C18H26O2/c1-13(2)18-10-9-17(4,20-18)16(11-18)19-12-15-8-6-5-7-14(15)3/h5-8,13,16H,9-12H2,1-4H3/t16-,17+,18-/m1/s1
    Key: QMTNOLKHSWIQBE-UHFFFAOYSA-N
  • CC1=CC=CC=C1COC2CC3(CCC2(O3)C)C(C)C
Properties
C18H26O2
Molar mass 274.404 g·mol−1
Appearance Colourless
Melting point −56 °C (−69 °F; 217 K)
Boiling point 330 °C (626 °F; 603 K)
Hazards
Lethal dose or concentration (LD, LC):
>2000 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cynmethylin (or cinmethylin) is a preëmergent cineole herbicide used in Australia on wheat, and commonly for rice and cereal crops. It is the only Group T (Aus) (Group Q, global, Group 30, numeric) herbicide. It controls annual ryegrass and the unusual mode of action avoids resistance. It works by inhibiting fatty acid thioesterase, disrupting cell membranes. It was introduced in 1989. As of 2025, approval is pending in Europe.

Cynmethylin was first registered in Australia in 2003 (as an active product), but as a product only in 2019, by BASF, as a 750 g/l emulsifiable concentrate.

Cynmethylin can provide 12 weeks' residual control.

It is sold under the tradenames "Luximax", "Cinch" and "Argold".

References

  1. 1 2 3 4 5 6 7 Hertfordshire, University of. "Cinmethylin (Ref: BAS 684 H)". sitem.herts.ac.uk.
  2. 1 2 3 "Luximax® | BASF Crop Solutions Australia". crop-solutions.basf.com.au.
  3. ↑ "APVMA PubCRIS: Cinmethylin". portal.apvma.gov.au. Australian Pesticides and Veterinary Medicines Authority. Retrieved 10 August 2025.
  4. ↑ "APVMA PubCRIS: LUXIMAX HERBICIDE". portal.apvma.gov.au. Australian Pesticides and Veterinary Medicines Authority. Retrieved 10 August 2025.