Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-07-20
2003-02-18
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S255050, C514S269000, C514S336000, C514S362000, C514S369000, C514S372000, C514S376000, C514S380000, C514S386000, C514S397000, C514S407000, C514S422000, C514S444000, C514S450000, C514S238500, C514S298000, C514S316000, C514S319000, C514S406000, C546S291000, C548S559000, C548S265800, C548S267200, C549S060000, C549S265000, C549S267000
Reexamination Certificate
active
06521622
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to the field of fungicidal compositions and methods. More particularly, the present invention concerns novel fungicidal heterocyclic aromatic amides and methods involving application of fungicidally effective amounts of such compounds to the locus of a plant pathogen. The present invention also concerns methods useful in the preparation of heterocyclic aromatic amides and their 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. with antibiotic properties (Barrow, C. J.; et al.,
Journal of Antibiotics,
1997, 50(9), 729). These substances have also been found to be effective fungicides (
The Merck Index,
Twelfth Edition, S. Budavari, Ed., Merck and Co., Whitehouse Station, N.J., 1996, p.120). WO 97/08135 describes acylaminosalicylic acid amides which are useful as pesticides. EP-A-O-661269 discloses substituted heterocyclic carboxylic acid amides useful as medical drugs. JP-A-7-233165 discloses antifungal dilactones having 3-hydroxypyridinecarboxyl groups with antimycotic action. The iso-butyryl, tigloyl, iso-valeryl and 2-methylbutyryl derivatives of these latter compounds are further described in the following references:
Tetrahedron
1998, 54, 12745-12774;
J. Antibiot.
1997, 50(7), 551;
J. Antibiot.
1996, 49(7), 639;
J. Antibiot.
1996, 49(12), 1226; and
Tetrahedron Lett.
1998, 39, 4363-4366.
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 compounds comprising
heterocyclic aromatic amides (HAA) of the Formula I:
wherein X
1
-X
4
, Z, and A are hereafter defined. The invention also encompasses hydrates, salts and complexes thereof.
The present invention also provides fungicidal compositions comprising the HAA in combination with phytologically acceptable carriers and/or diluents. Methods for the use of the heterocyclic aromatic amide compounds and compositions are also disclosed.
It is an object of the present invention to provide HAA 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 fungal infestations, which methods include the application of HAA and compositions containing same.
Further objects and advantages of the present invention will be apparent from the description which follows.
REFERENCES:
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Barrow, et al., “Antimycins, Inhibitors of ATP-Citrate Lyase, from a Streptomyces sp.”, Journal of Antibiotics, vol. 50, No. 9, pp. 729 (1997).
Budavari, et al., “The Merck Index”, Twelfth Edition, Merck and Co., Whitehouse Station, N.J., pp. 120 (1996).
Shimano, et al., “Total Synthesis of the Antifungal Dilactones UK-2A and UK-3A: The Determination of their Relative and Absolute Configurations, Analog Synthesis and Antifungal Activities,” Tetrahedron Letters, vol. 54, pp. 12745-12774 (1998).
Ueki, et al., “UK-3A, a Novel Antifungal Antibiotic from Streptomyces sp. 517-02: Fermentation, Isolation, Structural Elucidation and Biological Properties,” Journal of Antibiotics, vol. 50, No. 7, pp. 551 (1997).
Ueki, et al., “UK-2A, B, and D, Novel Antifungal Antibiotic form Streptomyces sp. 517-02. I. Fermentation, Isolation, and Biological Properties,” Journal of Antibiotics, vol. 49, No. 7, pp. 639 (1996).
Hanafi, et al., “UK-2A, B, C and D, Novel Antifungal Antibiotic from Streptomyces sp. 517-02,” Journal of Antibiotics, vol. 49, No. 12, pp. 1226 (1996).
Shimano, et al., “Enantioselective Total Synthesis of the Antifungal Dilactone, UK-2A: The Determination of the Relative and Absolute Configurations,” Tetrahedron Letters vol. 39, pp. 4363-4366 (1998).
Dent, III William H.
Fitzpatrick Gina M.
Gajewski Robert P.
Meyer Kevin G.
Miesel John L.
Corvin Carl D.
Dow AgroSciences LLC
McKenzie Thomas
Shah Mukund J.
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