Lancotrione
Weed control herbicide
From Wikipedia, the free encyclopedia
Lancotrione is a herbicide, closely related to tefuryltrione. Its mode of action inhibits 4-hydroxyphenylpyruvate dioxygenase (HPPD), an enzyme which produces homogentisic acid.[2]
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| Names | |
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| Preferred IUPAC name
2-[2-chloro-3-[2-(1,3-dioxolan-2-yl)ethoxy]-4-methylsulfonylbenzoyl]cyclohexane-1,3-dione | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
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| Properties | |
| C19H21ClO8S | |
| Molar mass | 444.88 g·molâ1 |
| Density | 1.47[1] |
| Related compounds | |
Related compounds |
tefuryltrione |
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 announced by Ishihara Sangyo Kaisha in 2016,[2] and commercialised in 2019.[3] Lancotrione is a new herbicide, usually used in the form of sodium salt to control grass weeds, in rice crops.[4] As such, little is yet known about it.
Synthesis
It starts from 1-bromo-2,3-dichloro-4-methylsulfonylbenzene, (1), which is then refluxed with sodium hydroxide in tert-butanol. (2) This is alkylated with 2-(2-chloroethyl)-1,3-dioxolane under basic conditions, (3), converted in a palladium-catalysed carbonylation to a methyl ester, (4). The ester is then saponified, and the consequent benzoic acid derivative, (5), with O-acylation of 1,3-cyclohexanedione and subsequent cyanide-catalyzed rearrangement, makes lancotrione.[5]