Cynmethylin

Last updated
Cynmethylin
Cinmethylin v2.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 402-410-9
KEGG
PubChem CID
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
AppearanceColourless [1]
Melting point −56 °C (−69 °F; 217 K) [1]
Boiling point 330 °C (626 °F; 603 K) [1]
Hazards
Lethal dose or concentration (LD, LC):
>2000 mg/kg (rat, oral) [1]
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 preemergent 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. [1] [2] It was introduced in 1989. As of 2025, approval is pending in Europe. [1]

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. [3] [4]

Cynmethylin can provide 12 weeks' residual control. [2]

It is sold under the tradenames "Luximax", "Cinch" and "Argold". [2] [1]

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.
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