Naphthoquinone derivatives

Details Naphthoquinone derivatives Naphthoquinone derivatives

1996-08-09

1998-11-10

Reamer, James H.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ketone doai

552298, 552299, A61K 3112

Patent

active

058345159

DESCRIPTION:

BRIEF SUMMARY
This invention relates to certain naphthoquinone derivatives, one of which is novel, methods for their preparation, compositions containing such compounds and their use as pesticides, such as fungicides and, especially, insecticides and acaricides.
It has been found that extracts of plants of the genus Calceolaria, particularly Calceolaria sessilis, Calceolaria andina and Calceolaria glabrata var. meyenenis found in Chile, exhibit pesticidal activity. Purification and analysis of these extracts has resulted in the isolation and identification of certain naphthoquinone derivatives which also exhibit pesticidal activity.
According to the present invention there is therefore provided a compound of general formula I ##STR2## in which R represents a hydrogen atom or a hydroxyl or an ethanoyloxy group, for use as a pesticide, for instance, a fingicide and/or, especially, an insecticide and/or an acaricide.
The compound of formula I may be in pure form or in admixture with one or more other compounds of formula I. It is particularly preferred that the compound of formula I, or at least one of the compounds of formula I, is that in which R represents an ethanoyloxy group.
The compound of formula I in which R represents a hydroxyl group may tautomerise to form the corresponding 4hydroxynaphthalene-1,2-dione and the invention therefore also includes this tautomer. In addition, the compound of formula I in which R represents a hydroxyl group may form salts with alkali metals, such as sodium and potassium, and alkaline earth metals and these salts also form part of the invention.
As mentioned above, extracts of plants of the genus Calceolaria are themselves pesticidally active. Thus, according to another aspect of the present invention there is provided an extract of a Calceolaria species for use as a pesticide, for instance, a fungicide and/or, especially, an insecticide and/or an acaricide.
A partially purified extract of a Calceolaria species may be employed. Preferably, the extract comprises at least one compound of formula I as defined above.
Compounds of formula I or extracts as defined above may be obtained by extracting comminuted plant material, for instance, the leaves and/or stems, of a Calceolaria species with a solvent. Initial extraction is preferably carried out with a hydrocarbon solvent such as an alkane, especially hexane, the extract then being concentrated, for instance, by evaporation. The concentrated extract may then be purified by chromatography, suitably column chromatography using a silica gel column, followed by further separation processes.
Preferably, the Calceolaria species is Calceolaria andina, Calceolaria sessilis or Calceolaria glabrata var. meyenenis.
The compounds of formula I may be utilised as a pesticide in the form of an extract as defined above. Alternatively, the isolated compounds of formula I or extracts of a Calceolaria species may be formulated with an inert carrier or diluent to produce a pesticidal composition. According to a further aspect of the present invention there is therefore provided a pesticidal, for instance, a fungicidal and/or, especially, an insecticidal and/or acaricidal, composition which comprises a carrier and, as active ingredient, a compound of formula I as defined above or an extract of a Calceolaria species as defined above.
The compositions of the invention may contain from 0.001 to 95% by weight of the active ingredient of formula I. Preferably, the compositions contain from 0.001 to 25% by weight of the active ingredient when they are in ready-to-use form. However, higher concentrations, for instance, up to 95%, may be present in compositions to be sold as concentrates for dilution before use.
The compositions of the invention may be mixed with a variety of appropriate inert carriers such as solvents, diluents and/or surface-active agents to form dusts, granular solids, wettable powders, mosquito coils or other solid preparations or emulsions, emulsifiable concentrates, sprays, aerosols or other liquid preparations. Suitable solvents and diluents

REFERENCES:
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patent: 4970328 (1990-11-01), Lindner et al.
patent: 5053418 (1991-10-01), Latter et al.
patent: 5310762 (1994-05-01), Latter et al.
Cooke, Aust. J. of Scientific Research, vol. 3A, pp. 481-486 (1950).

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