Fungicide comprising 4-methyl-6-pentyl-2H-pyran-2-one

Details Fungicide comprising 4-methyl-6-pentyl-2H-pyran-2-one Fungicide comprising 4-methyl-6-pentyl-2H-pyran-2-one

2000-02-24

2001-06-26

Owens, Amelia (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C514S460000

Reexamination Certificate

active

06251832

ABSTRACT:

FIELD OF THE INVENTION
The present invention is directed to a compound having fungicidal activity, to fungicidal compositions containing the compound, and to methods of using them.
BACKGROUND ART
The antifungal activity of the natural product 6-pentyl-2H-pyran-2-one (6-PAP) is well known and the in vitro activity of this compound against a range of phytopathogens has been reported (1, 2, 3, 4). Early structure-activity studies indicated that minor structural modifications to 6-PAP yielded compounds with reduced antifungal activity (5).
Prior to its identification as a natural product, the chemical synthesis of 6-PAP and its structural analogs received attention because of the potent organoleptic properties of these compounds (6, 7). However, despite the attention paid to the synthesis of 6-PAP by these and other methods (8, 9), its preparation remains costly.
As an organic natural product 6-PAP is innately biodegradable. Combined with its established use as a food additive and assumed low toxicity 6-PAP is an attractive candidate for development as an agricultural/horticultural fungicide. However, its cost is an obstacle to further development.
The applicants have now surprisingly found that a structural analog of 6-PAP, namely 4-methyl-6-pentyl-2H-pyran-2-one, has fungicidal activity similar to that of compound 6PAP. The applicants have also found that 4-methyl-6-pentyl-2H-pyran-2-one can be prepared with relative ease and economy as compared to preparation of 6-PAP. It is towards the use of 4-methyl-6-pentyl-2H-pyran-2-one as a fungicide that the present invention is directed.
SUMMARY OF THE INVENTION
Accordingly, in a first aspect, the present invention provides a fungicidal composition comprising the compound 4-methyl-6-pentyl-2H-pyran-2-one, in combination with one or more suitable carriers, adjuvants and/or diluents.
In a second aspect, the present invention provides a method of preventing or at least inhibiting the growth of fungi which comprises the step of applying the compound 4-methyl-6pentyl-2H-pyran-2-one to the fungi or their locus.
In a third aspect, the present invention provides a method of preparing the compound 4-methyl-6-pentyl-2H-pyran-2-one, the method comprising the following steps:
(a) reacting the compound ethyl 3-methyl-2-butenoate with hexanoyl chloride under suitable conditions to produce Friedel-Crafts acylation products; and
(b) reacting the acylation products obtained in step (a) with a concentrated acid under conditions suitable to achieve lactonisation and thereby obtain the compound 4-methyl-6-pentyl-2H-pyran-2-one.
Those persons skilled in the art will appreciate that although the invention is broadly defined above, it also includes embodiments of which the following description provides examples.


REFERENCES:
patent: WO9904633 (1999-04-01), None
Pittit, AO et al ‘Synthesis and flavor properties of some alkyl-substituted alpha-pyrone derivatives’ CA 83;191473, 1975.

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