Cyclic dodecapeptide and process for the preparation thereof

Details Cyclic dodecapeptide and process for the preparation thereof Cyclic dodecapeptide and process for the preparation thereof

1998-05-29

2002-05-07

Low, Christopher S. F. (Department: 1654)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Cyclic peptides

C530S329000, C424S405000, C435S069100, C435S254100, C504S117000

Reexamination Certificate

active

06384186

ABSTRACT:

The present invention relates to a novel organochemical compound, hereinafter referred to as omphalotin, a process for its preparation by an essentially microbiological route and its use as microbicide and pesticide, preferably for controlling animal pests, harmful fungi and bacteria.
The novel omphalotin has been found and, based on the present spectroscopic and other analytical data, the following formula (I) is proposed:
where—(terminal) represents —CH
3
,
represents
or (terminal) represents
represents —CH
2
—,
represents
represents
Furthermore, it has been found that the novel omphalotin can be employed for controlling pests and parasites in plants and warm-blooded animals. In particular, it has high activity against nematodes and arthropods (like insects and arachnids), and against microbial pests, in particular against fungi and bacteria. Owing to these properties, the novel compound and compositions comprising this compound can be employed particularly advantageously in crop protection, in the protection of stored products, in the hygiene sector and in animal breeding and animal husbandry.
The novel compound of the formula (I) is obtained by cultivating suitable microorganisms from the class of the Basidiomycetes, preferably from the genera Omphalotus and Lampteromyces, particularly preferably Omphalotus, in a customary manner in a cultured medium containing assimilable carbon and nitrogen sources and mineral salts, under aerobic conditions, and isolating the desired compound by customary methods.
Knowing the properties of the novel compound according to the invention, it is possible in an easy and quick manner to select the appropriate microorganism strains which produce the omphalotin according to the invention by routine processes, with the aid of customary chromatographic, spectroscopic, microbiological (for example inhibition zone test) and/or biological methods (for example by determining the activity against nematodes or insects).
For the microbiological preparation of the compound according to the invention, preference is given to using omphalotus strains, in particular Omphalotus olearius strains (synonym: Clitocybe illudens strains). Very particular preference is given to using the Omphalotus olearius strains No. 83 039, 90 173, 91 050, 92 095, 93 162 and 90 170 and those variants and mutants of these strains which have features which are essential for carrying out the present invention, or which have the same function.


REFERENCES:
File Caplus on STN, AN No. 1997:86488. Meyer et al. Screening of Higher Fungi for the Production of Nematicidal Compounds Using Melaoidogyne Incognita (Kofoid & White) Chitwood as Test Organism, Meded. Fac. Landbouwkd. Toegepaste Biol. Wet. (Univ. Gen.*
File Scisearch on STN, AN No. 91:233894. Arnone et al. ‘Secondary Mold Metabolites .31. Isolation and Structure Elucidation of Illudins-A and Illudins-B, and Illudanlenol, New Sesquiterpenoids Form Clitocybe-Illudens,’ Journal of the Chemical Society-P.

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