Plant protecting and regulating compositions – Seed coated with agricultural chemicals other than fertilizers
Patent
1994-12-07
1996-02-13
Haley, Jacqueline
Plant protecting and regulating compositions
Seed coated with agricultural chemicals other than fertilizers
4352521, 4352541, 4352551, 4351721, 514422, 514423, 548517, 548539, A01N 4336, C07D20744, C07D40510
Patent
active
054911222
DESCRIPTION:
BRIEF SUMMARY
FIELD OF INVENTION
The present invention relates to fungicidal and insecticidal active compounds, compositions and derivatives thereof, and processes for producing such compounds. The invention also relates to fungicidal and insecticidal compositions comprising these compounds, either alone or in combination with other pesticides or growth regulators, and the use of the compounds or compositions of the invention for controlling fungi and/or insects.
BACKGROUND OF THE INVENTION
For a number of years it has been known that various microorganisms produce secondary metabolites exhibiting biological activity so as to be useful as pesticides for controlling diseases and pests.
Although progress has been made in the field of identifying and developing biological pesticides for controlling various diseases and pests in plants and animals of agronomical and horticultural importance, most of the pesticides 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 an increasing concern for the impact of such pesticides on the environment and the ecosystems surrounding farmlands, and consequently there exists an outspoken need for pesticides that are more specific in their activity, and are readily degradable in the natural environment.
Natural products provide an alternative to synthetic fungicides and insecticides in that they may have another mode of action, may be more biodegradable and safer in the environment.
Several compounds have been previously isolated from the genus Pyrenophora. The Aspergillomarasamines, including Toxin A (below), are a series of compounds derived from several genera of fungi including Pyrenophora. These compounds are toxic to higher plants and are widely distributed in fungi. (Physio. Plant Path., Vol. 14, pp. 41-46, 1979).
Another series of compounds isolated from a number of genera including Pyrenophora are the Ophiobolins. A report of these phytotoxic and antimicrobial compounds from P. teres has not previously been made. (Proc. Natl. Acad. Sci. USA, Vol. 84, pp. 3081-3085, 1987). Pyrenolide compounds have been isolated from P. teres. (Agric. Biol. Chem, Vol. 44, pp. 2761-2762, 1980). However, their biological activity spectrum includes antifungal activity but no insecticidal activity.
Compounds reported from the genus Pyrenophora are the following: ##STR1##
It is, therefore, an object of the present invention to provide novel fungicidal and insecticidal compounds which originate from natural sources or are direct derivatives of such compounds and which confer protection for plants against harmful fungi and insects.
SUMMARY OF THE INVENTION
The present invention is based on the extremely surprising recognition that an extract of the biomass of Pyrenophora teres was found to inhibit the growth of fungi, insects and bacteria. Compounds of this structural type have not been previously reported in the literature. Indeed, members of Pyrenophora teres have not previously been reported to contain compounds which inhibit the growth of fungi, insects and bacteria.
Generally stated, in one aspect the present invention provides for a substantially pure strain of Pyrenophora teres (which belongs to the class Ascomycetes), designated CL806 (International Mycological Institute CC# 35 1438), and a substantially pure fungal strain belonging to the class Deuteromycetes designated 33-971 (International Mycological Institute CC# 355496), and mutants thereof. The invention also relates to the use of these microorganisms to produce the compounds of the invention as fungicidal and/or insecticidal compositions.
More specifically, the invention relates to compounds of formulas I and IV and any tautomers thereof: ##STR2## wherein R.sub.1 is hydrogen, methyl or acetyl, or R.sub.1 is sodium, potassium, lithium or any other salt; heptyl, octyl, nonyl and decyl.
Preferred compounds according to the present invention are the compounds of formulas II, III, V and VI: ##STR3##
Said compounds and their tautomeric
REFERENCES:
patent: 4977275 (1990-12-01), Hasegawa et al.
patent: 5171740 (1992-12-01), McAlpine et al.
patent: 5244658 (1993-09-01), Parke
Bachmann Torben L.
Heide Morten
Manker Denise C.
Nielsen Ruby I.
Rosendahl Connie N.
Haley Jacqueline
Lambiris Elias J.
Novo Nordisk A S
Novo Nordisk Entotech, Inc.
Zelson Steve T.
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