Fungicidal compositions and methods, and compounds and...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C514S563000

Reexamination Certificate

active

06297401

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to the field of fungicidal compositions and methods, and more particularly to plant fungicides and methods involving the application of fungicidally effective amounts of such compounds to the locus of a plant pathogen. The present invention also provides novel compounds and methods useful in the preparation of fimgicides, and fungicidal compositions.
2. Description of the Prior Art
A variety of antifungal compositions and methods are well known in the art. Antimycin, for example, has been identified as a naturally occurring substance produced by Streptomyces spp which has efficacy as a fungicide. However, there has remained a need for new fungicides. The present invention provides fungicides which have a high residual activity, greater activity at lower application rates, curative activity, and a broader spectrum of efficacy.
SUMMARY OF THE INVENTION
Briefly describing one aspect of the present invention, there are provided fungicidal compounds comprising acylated aminosalicylamides of the Formula I:
wherein m, n, X, Y, Z and R
1
-R
6
are as hereafter defined. The invention also encompasses hydrates, salts and complexes thereof.
The present invention also provides fungicidal compositions comprising the acylated aminosalicylamides in combination with phytologically acceptable carriers and/or diluents. Methods for the use of the acylated aminosalicylamide compounds and compositions are also disclosed.
In another aspect, the present invention includes compounds and methods for preparation of the acylated aminosalicylamides. Encompassed are certain novel cyclic anmines and 3-nitrosalicylamides, including ones having fungicidal efficacy, as well as methods for the preparation thereof Also included are certain nitro intermediates and their method of preparation.
It is an object of the present invention to provide acylated aminosalicylamides and compositions thereof which are effective as antifungal agents.
Another object of the present invention is to provide methods for the control and/or prevention of fungus infestations, which methods include the application of acylated aminosalicylamides and compositions containing same.
The present invention also has an object the provision of certain cyclic amines, their method of preparation and use in producing acylated aminosalicylamides, and optionally the use of such amines as fungicides.
It is a further object of the present invention to provide certain 3-nitrosalicylamides useful as fimgicides and in the preparation of the fungicidal acylated aminosalicylamides.
Further objects and advantages of the present invention will be apparent from the description which follows.


REFERENCES:
patent: 3459534 (1969-08-01), Dorfman
patent: 3994975 (1976-11-01), Oude Alink et al.
patent: 5034393 (1991-07-01), Hackler et al.
patent: 5292743 (1994-03-01), Liebeschuetz
patent: 5447960 (1995-09-01), Sinnott et al.
patent: 4110483A1 (1992-10-01), None
patent: 1-228949 (1989-09-01), None
patent: 3-95141 (1991-04-01), None
patent: WO 97/08135 (1997-03-01), None
Hutchins et al., “Stereoselective Reductions of Substituted Cyclohexyl and Cyclopentyl Carbon-Nitrogen &pgr; Systems with Hydride Reagents”,J. Org. Chem, 1983, 48, 3412-3422.
Selwood et al., Structure-Activity Relationships of Antifilarial Antimycin Analogues: A Multivariate Pattern Recognition Study,J. Med. Chem., 1990, 33, 136-142.
Neft et al., Inhibition of Electron Transport by Substituted Salicyl-N-(n-octadecyl)amides, Department of Chemistry, Utah State University,Chem. Abstr.76, 94491e,J. Med. Chem.14, 1169 (1971).
Dickie et al., The Chemistry of Antimycin A. XI. N-Substituted 3-Formamidosalicylic Amides,J Med. Chem., vol. 6, Jul. 1963, pp. 424-427.
Tokutake et al., Structural Factors of Antmycin A Molecule Required for Inhibitory Action,Biochimica et Biophysica Acta, 1185 (1994) 271-278.
Aburaki et al., Synthesis of Deisovalerylblastmycin,Chemistry Letters, pp. 701-704 (1976), published by Chemical Society of Japan.
Kinoshita et al., Syntheses of (3S, 4R, 15S)-4,15-Dimethyl-1,5-dioxa-3-(3'-formamidolsalicylamido)-cyclopentadecane-2,6-dione and its (15R)-Epimer, New Antimycin Analogs,Bulletin of the Chemical Society of Japan, vol. 44, No. 12, (1971).
Taborsky et al., Substituted Salicylanilides III,J. Pharm. Sci., vol. 52, No. 6, (1963) pp. 542-545.
Abidi et al., Liquid chromatography-thermospray mass spectrometric study of N-acylamino dilactones and 4-butyrolactones derived from antimycin A,J. of Chromatography, 522 (1990) 179-194.
Miyoshi et al., A model of antimycin A binding based on structure-activity studies of synthetic anitmycin A analogues,Biochim. et Biophysica Acta1229 (1995) 149-154.
Xu et al., Comparison between the properties of 3-nitrosalicyl-N-alkylamide and antimycin A acting on QH2: cytochrome c reductase,Biochim. et Biophysica Acta,, 1142 (1993) 83-87.
Communication to the Editor, Journal of Antibiotics vol. 46, No. 4, (1992), pp. 701-703.
Caglioti et al., The Structure of Neoantimycin,Tetrahedron, vol. 25, pp. 2193-2221 (1969).
Immamura et al., Novel Antimycin Antibiotics, Urauchimycins A and B, Produced by Marine Actinomycete, J. of Antibiotics, vol. 46, No. 2 (1992).
Tokutake et al., Inhibition of electron transport of rat-liver mitochondria by synthesized antimycin A analogs, Biochemica et Biophysica Acta, 1142 (1993) 262-268.
Keizo et al., Antimycin derivatives,Chem. Abstractsvol. 70, 1969, p. 310.
Makoto et al., Fungicides manufacture with streptoverticillium,CA Selects: Fungicides, Issue 26 (1995), p. 9.
Unknown number, Thionosalicylic Acid Anilides, Salts Thereof, Intermediates Therefor and Productions Processes, F. Bayer Akt., Kurz et al., South African patent application, dated Apr. 19, 1967.

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