Cyclopyrimorate

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 952-668-6
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).
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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

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