Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Patent
1993-08-16
1996-05-07
Lilling, Herbert J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
435 711, 4352541, 530321, C12P 2104, C07K 1102, A01N 6304, C12N 114
Patent
active
055146481
DESCRIPTION:
BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a national stage application filed under 35 U.S.C. 371 of PCT/DK91/00273 filed Sep. 17, 1991, which is incorporated herein by reference.
1. Field of the Invention
This invention relates to novel fungicidally active compounds, methods of producing such compounds, microorganisms capable of producing said compounds, compositions containing said compounds, and the use of such compositions for controlling fungi in valuable crops, animals, including birds and mammals, and in the preservation of wood and timber, paints, cosmetics, foods and feeds.
2. Background of the Invention
For a number of years it has been known that various microorganisms produce metabolites exhibiting biological activity so as to be useful as biocides for combating diseases and pests.
Especially it has been known that some species of the genus Curvularia produce different metabolites exhibiting biological activity, in particular as phytotoxins. However, none of these metabolites are known to be fungicides. C. lunata (Wakk.) Boed was found to produce at least two phytotoxins. They cause necrotic spots on plant leaves even when they are highly diluted. (F. Macri and A. Vianello, Physiological Plant Pathology 8:325-331, 1976). The toxins are phytotoxins and are non host specific. Host specific toxins have been isolated from culture filtrates of C. pallescens Boedijn and from diseased host leaves attacked by this species (Olufolaji, Cryptogamie Mycol. 7(4):335-342, 1986). These toxic substances gave chlorotic spots to maize plants. They later became necrotic similar to in-vivo symptoms of the disease caused by C. pallescens.
Curvularin, a macrocyclic metabolite, has been isolated from a Curvularia species (O. C. Musgrave, J. Chem Soc., 1956, 4301) and from C. lunata (Coombe et al, Aust. J. Chem. 21:783, 1968). The compound has the formula C.sub.16 H.sub.20 O.sub.5 (molecular weight 292.3) and has the formula 1 below: ##STR1##
Crude curvularin was isolated as colourless or pale yellow-brown crystals.
Neither curvularin nor the crude filtrates from Curvularia showed anti-bacterial activity (against Bacillus subtilis, Escedchia coli, and Staphylococcus aureus) or anti-fungal activity (spore germination test with Penicillium digitalum).
None of the above compounds are useful for combating plant diseases and pests because they are strong phytotoxins.
Although progress has been made in the field of identifying and developing biological biocides for combating various diseases and pests in plants and animals of agronomical importance, most of the biocides in use are still synthetic compounds that are difficult to decompose in nature and have a broad spectrum of activity.
In the last decade or so there has been a still increasing concern for the impact of such biocides on the environment and the ecosystems surrounding farmlands, and consequently there exists an outspoken need for biocides that are more specific in their activity, and are readily degradable in the natural environment.
A number of compounds related to the compounds disclosed through this invention have been disclosed in European Publication No. EP 360 760 (Sandoz AG), published 28.3.1990. These compounds are disclosed as being produced by the fungal genus Septoria, and as having interesting pharmacological properties, e.g. antifungal activity in animals against yeast and yeast-like species causing systemic attacks. The publication contains only reference to one test against Candida, and no reference to which of the 82 exemplified compounds were tested for this activity, but states that the most preferred compound can be represented by the formula: cyclo- Pec-MeVal-Val-MeAsp-MeIle-MeIle-Gly-MeVal-TyrOMe-D-Lact! (SEQ ID NO: 1) (Example 1, first compound).
SUMMARY OF THE INVENTION
As indicated above known metabolites from the mold genus Curvulada all have exhibited a strong phytotoxic activity, but it has now surprisingly been found that fungi belonging to said genus also produce metabolites that exhibit strong antifungal activ
REFERENCES:
Marci et al., Physiol. Plant Path., vol. 8, pp. 325-331 (1976).
Olufolaji, Cryptogamie Mycol. vol. 7. (4), pp. 335-342 (1986).
Coombe et al., Aust. J. Chem., vol. 21, pp. 783-788 (1968).
O. C. Musgrave, J. Schem. Soc., pp. 4301-4304 (1956).
Breinholt Jens
Jensen Georg W.
Nielsen Ruby I.
Agris Cheryl H.
Lilling Herbert J.
Novo Nordisk A S
Zelson Steve T.
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