Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1998-03-18
2001-01-09
Huang, Evelyn Mei (Department: 1612)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C435S118000, C435S254100, C435S255700, C435S911000, C546S115000
Reexamination Certificate
active
06172006
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to biologically active compounds, methods for their production, and microorganisms capable of synthesizing such compounds.
The invention further relates to fungicidal compositions comprising said compounds and methods of controlling fungi by the use of such compositions.
Also contemplated is an isolated pure culture of a microorganism capable of producing said compounds.
BACKGROUND OF THE INVENTION
Synthetic chemical fungicides, pesticides, acaricides, preservatives etc. have been used for decades, in various fields, such as medicine, agriculture, forestry, horticulture, food industry etc. However, today it is realised that very often in general such chemicals, have a negative impact on the environment. Therefore, especially the search for biological agents such a as microbes and microbial metabolites, useful for controlling diseases and pests in valuable crops, has been a growing area of research during the last decade.
It is thus well known that microorganisms are capable of producing metabolites associated with interesting biological activities.
Strains of the fungal genus Cladobotryum have till now not been found capable of producing such useful compounds.
SUMMARY OF THE INVENTION
The present inventors have surprisingly succeeded in isolating and characterizing novel biologically active compounds from a fungus of the genus Cladobotryum.
The novel compounds have the generic formula I:
wherein
R
1
is aryl, such as phenyl, optionally mono- or plurisubstituted with alkyl with 1-6 carbon atoms, hydroxy, alkoxy, halogen, amino or a nitro group,
R
2
is hydrogen, straight or branched chain alkyl with 1-6 carbon atoms, straight or branched chain alkenyl with 2-6 carbon atoms, straight or branched chain alkynyl with 2-6 carbon atoms,
R
3
is hydrogen, straight or branched chain alkyl with 1-10 carbon atoms, straight or branched chain alkenyl with 2-10 carbon atoms, straight or branched chain alkynyl with 2-10 carbon atoms,
R
4
is hydrogen, straight or branched chain alkyl with 1-6 carbon atoms, straight or branched chain alkenyl with 2-6 carbon atoms, straight or branched chain alkynyl with 2-6 carbon atoms, and
R
5
is hydroxymethyl, formyl, carboxyl, or carboxyl ester with 1-6 carbon atoms.
In a preferred embodiment of compound with the formula I, R
1
is phenyl, R
2
is hydrogen, R
3
is 2-(2(E)-butenyl), R
4
is methyl, and R
5
is formyl resulting in a compound with the formula Ia.
In another aspect, the invention relates to a method of preparing said compounds comprising
a) cultivating a microorganism capable of producing said compound in or on a suitable nutrient medium and under suitable conditions, and
b) recovering the compound from the biomass and/or the culture medium.
In an embodiment of the invention the method further comprises the step of c) chemically modifying the compound obtained in step b).
In a specific embodiment of the invention said microorganism is a fungus of the genus Cladobotryum, preferably of the is species
Cladobotryum varium,
especially of the strain
Cladobotryum varium
NN006437 (CBS 331.95) or a mutant thereof capable of producing a compound of the invention.
A third object of the invention is to provide a fungicidal composition comprising, as an active ingredient, said compound alone or in combination with one or more other fungicidal or pesticidal agents and/or growth regulators.
Also contemplated according to the invention is a method of controlling fungi at a locus infested or liable to be infested therewith, which comprises applying to said locus said compound or said composition of the invention.
Further the invention relates to the use of the novel compounds as a fungicide, preservative and/or additive for combating plant diseases, especially fungal attack or control fungi in timber, wood, cosmetics, paints, growth media, feeds and foods.
Lastly the invention relates to an isolated pure culture of the microorganism
Cladobotryum varium
NN0054922 (CBS 331.95) or a mutant thereof capable of producing a compound of the invention.
REFERENCES:
patent: 5714595 (1998-02-01), Viaud
Tezuka, et al., Chem. Pharm. Bull., vol. 42, No. 12, pp. 2612-2617 (1994).
Breinholt Jens
Demuth Helle
Romer Birgitte Rassing
Gregg Valeta
Huang Evelyn Mei
Lambiris Elias J
Novo Nordiskals
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