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AssigneeMontedison S.p.A.
InventorsLuigi Abbruzzese, Franco Gozzo, Giorgio Rossi, Marcella Masoero, Simone Lorusso, Paola Bonola, Gino Tamburin
Estimating the term…
Quinoline derivatives having fungicidal action and, more particularly, quinoline derivatives quaternarized to the nitrogen atom and effective against peronospora, oidium, and Botrytis, are disclosed.
A method for combatting or preventing infections of plants by Botrytis cinerea pers., Plasmopara Viticola (B. et C), Berl et de Toni, and Sphaerotheca fulginea (Schlech) Salmon, which comprises sprinkling on the leaves of the plant to be protected an aqueous solution or suspension of an active anti-fungal agent which is a quinolinic derivative of the general formula ##STR5## wherein:
Dependencies are inferred from the claim text.
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No related US applications are recorded in the indexed filing history.
With only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms: quaternary compounds
Heterocyclic compounds
Term ended 15 Nov 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
It is known (Albert; Selective Toxicity, 5th Ed. 1973, p. 370, 10.7) that while 8-hydroxy quinoline has antibacterial activity in vitro, neither the O-alkyl nor the N-alkyl derivatives exhibit any activity (Albert, supra, pp. 370-377).
Nitrogen protonated salts of 8-hydroxyquinoline active against fungi are disclosed in Swiss Patent No. 490,021. However, those salts are quinoline derivatives in which both the nitrogen atom and the hydroxyl group are free or at any rate in equilibrium, in an aqueous solution, with a free basic form.
As shown by experimental data in said Swiss patent, 8-hydroxy-quinoline exhibits no activity in vivo with respect to Botrytis infesting vines, either as such or in the form of non-quaternarized salts.
8-hydroxy-quinolinium-N-methyl-iodide was prepared by treating 4.3 g (0.03 moles) of 8-hydroxyquinoline with 22.8 g (0.16 moles) of methyl iodide and 10 cc of ethanol.
This solution was reflux-heated under constant stirring for 4 hours, after which 150 cc of ethyl ether were added.
A solid precipitated from the solution. It was filtered, washed with ether and then crystallized from ethanol, thereby yielding 3.5 of yellow, hydrosoluble crystals having a melting point of 172.degree.-173.degree. C.