Cyclopyrimorate

Cyclopyrimorate
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
CAS Number	499231-24-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:142780;
ChemSpider	16050194;
EC Number	952-668-6;
PubChem CID	23013854;
UNII	0SVL4HSS2F;
CompTox Dashboard (EPA)	DTXSID40198157 ;
	InChI 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;
	SMILES CC1=C(C(=CC=C1)C2CC2)OC3=NN=C(C=C3OC(=O)N4CCOCC4)Cl;
Properties
Chemical formula	C19H20ClN3O4
Molar mass	389.84 g·mol−1
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	>5000 mg/kg (rat, oral)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

^ ^a ^b ^c Hertfordshire, University of. "Cyclopyrimorate (Ref: SW-065)". sitem.herts.ac.uk.
^ 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.
^ ^a ^b ^c 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.
^ 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.

Links

Cyclopyrimorate in the Pesticide Properties DataBase (PPDB)

[database-1] 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.

[mamiko-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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