Cyclopyrimorate

Last updated
Cyclopyrimorate
Cyclopyrimorate.svg
Names
Preferred IUPAC name
6-chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-yl morpholine-4-carboxylate
Other names
  • H-965
  • 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 952-668-6
PubChem CID
UNII
  • InChI=1S/C19H20ClN3O4/c1-12-3-2-4-14(13-5-6-13)17(12)27-18-15(11-16(20)21-22-18)26-19(24)23-7-9-25-10-8-23/h2-4,11,13H,5-10H2,1H3
    Key: BXIGJZDQFDFASM-UHFFFAOYSA-N
  • CC1=C(C(=CC=C1)C2CC2)OC3=NN=C(C=C3OC(=O)N4CCOCC4)Cl
Properties
C19H20ClN3O4
Molar mass 389.84 g·mol−1
Hazards
Lethal dose or concentration (LD, LC):
>5000 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).

Cyclopyrimorate is a selective pyridazine herbicide, used to control broadleaf weeds and grassy weeds, on cereals and rice. It was launched in 2019 in Japan, and is also used in China. [1] Its mode of action is new, and cyclopyrimorate is the first member of the HRAC Group 33, (Group T, global), coming after decades of no new mode-of-action discoveries. [2]

It was invented by Mitsui Chemicals Agro, [3] who sell it tradenamed "Cyra". [1] They discovered it by modifying the structures of other pyridazine herbicides, such as pyridafol and credazine. [3]

Cyclopyrimorate works by a novel target site, of homogentisate solanesyltransferase (HST). The new mechanism avoids resistance to acetolactate synthase inhibitor herbicides. [3] It symptomatically causes bleaching, similar to other cartenoid biosynthesis inhibitors like mesotrione and norflurazon, however cyclopyrimorate is the only one to inhibit HST. [4]

References

  1. 1 2 3 Hertfordshire, University of. "Cyclopyrimorate (Ref: SW-065)". sitem.herts.ac.uk.
  2. ↑ Selby, Thomas P.; Satterfield, Andrew D.; Puri, Atul; Stevenson, Thomas M.; Travis, D. Andrew; Campbell, Matthew J.; Taggi, Andrew E.; Hughes, Kenneth A.; Bereznak, James (29 November 2023). "Bioisosteric Tactics in the Discovery of Tetflupyrolimet: A New Mode-of-Action Herbicide". Journal of Agricultural and Food Chemistry. 71 (47): 18197–18204. doi:10.1021/acs.jafc.3c01634. PMID   37285594.
  3. 1 2 3 Shino, Mamiko; Hamada, Takahiro; Shigematsu, Yoshio; Hirase, Kangetsu; Banba, Shinichi; Tsukamoto, Yoshihisa; Kadotani, Junji (1 January 2021). "Chapter 30 - Discovery and mode of action of cyclopyrimorate: A new paddy rice herbicide". Recent Highlights in the Discovery and Optimization of Crop Protection Products: 451–457. doi:10.1016/B978-0-12-821035-2.00033-4. ISBN   978-0-12-821035-2.
  4. ↑ Shino, Mamiko; Hamada, Takahiro; Shigematsu, Yoshio; Hirase, Kangetsu; Banba, Shinichi (2018). "Action mechanism of bleaching herbicide cyclopyrimorate, a novel homogentisate solanesyltransferase inhibitor". Journal of Pesticide Science. 43 (4): 233–239. doi:10.1584/jpestics.D18-008. PMC   6240781 . PMID   30479543.
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