Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-01-19
2001-03-06
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S200000, C548S204000
Reexamination Certificate
active
06197802
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to novel melithiazole derivatives, a process for their preparation, compositions containing such compounds, a method for combating a fungus at a locus comprising treating the locus with such compounds and their use as fungicides.
Food production relies upon a variety of agricultural technologies to ensure the growing population's dietary needs remain affordable, nutritious and readily available on grocery store shelves. Fungicides are one of these agricultural technologies which are available to the world community. Fungicides are agrochemical compounds which protect crops and foods from fungus and fungal diseases. Crops and food are constantly threatened by a variety of fungal organisms, which, if left uncontrolled, can cause ruined crops and devastated harvests.
The preparation of melithiazole C by reductive cleavage of myxothiazol A with subsequent transformation of the resulting melithiazole C amide into the corresponding methyl ester has been described by a poster of B. Böhlendorf et al. presented at the Dechema Naturstofftagung in Irsee, Germany in 1996. Melithiazole C disclosed on this poster shows weak in vitro activity against
Bortrytis cinera.
There is no indication that this compound could be active in vivo against other phytopathogenic fungi. Moreover, there is no hint to other derivatives of melithiazole C.
The underlying problem of the present invention was to find novel melithiazole derivatives having high in vivo activity against a broad range of phytopathogenic fungi.
SUMMARY OF THE INVENTION
The present invention provides novel melithiazole derivatives of the general formula I
wherein
R
1
represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkyloxiranyl, alkanoyl, alkoxycarbonyl, formyl, hydroxyalkyl, alkoxyalkyl, alkanoyloxyalkyl, hydroximinoalkyl, alkoxyiminoalkyl, hydrazonoalkyl or alkylhydrazonoalkyl group;
R
2
represents an alkoxy group;
R
3
and R
4
each independently represent a hydrogen atom or an alkyl group;
R
5
represents an alkyl group, and
R
6
represents a group of formula —COOR
7
or —CONR
7
R
8
, in which R
7
and
R
8
each independently represent a hydrogen atom or an alkyl group; with the proviso that melithiazole C or the corresponding amide of formula,
wherein Y represents NH
2
or OCH
3
, are excluded.
The new compounds combine excellent fungicidal activities against a broad range of phytopathogenic fungi in various crops with comparably high systemicities.
It is also an object of the invention to provide methods for controlling an undesired fungus by contacting said plants with a fungicidally effective amount of the new compounds.
It is another object of the invention to provide fungicidal compositions containing the new compounds as active ingredients.
These and other objects and features of the invention will be more apparent from the detailed description set forth hereinbelow, and from the appended claims.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has surprisingly been found that melithiazole derivatives of the general formula I
wherein
R
1
through R
6
are as hereinbefore defined, and excluding melithiazole C or the corresponding amide thereof, combine excellent fungicidal activity against diseases caused by phytopathogenic fungi even at low dose rates with high bioavailability due to their high systemicity.
Optionally substituted moieties may be unsubstituted or have from one up to the maximal possible number of substituents. Typically, 0 to 2 substituents are present. Each optionally substituted group is independently substituted by one or more halogen atoms or nitro, cyano, cycloalkyl, preferably C
3-6
cycloalkyl, cycloalkenyl, preferably C
3-6
cycloalkenyl, haloalkyl, preferably C
1-6
haloalkyl, halocycloalkyl, preferably C
3-6
halocycloalkyl, alkoxy, preferably C
1-6
alkoxy, haloalkoxy, preferably C
1-6
haloalkoxy, phenyl, mono- di- or trihalo-phenyl or pyridyl groups.
In general terms, unless otherwise stated, as used herein the term “halogen” may denote a bromine, iodine, chlorine or fluorine atom, and is preferably a bromine, chlorine or fluorine atom.
In general terms, unless otherwise stated herein, the terms “alkyl,” “alkenyl,” “alkanoyl,” “acyl” and “alkoxy’ as used herein with respect to a radical or moiety refer to a straight or branched chain radical or moiety. As a rule, such radicals have up to 10, in particular up to 6 carbon atoms. Suitably an alkyl or alkoxy moiety has from 1 to 6 carbon atoms, preferably from 1 to 5 carbon atoms. A preferred alkyl moiety is the methyl, ethyl, n-propyl, isopropyl or n-butyl group. A preferred acyl moiety is acetyl or propionyl.
The invention especially relates to compounds of the general formula I in which any alkyl part of the groups R
1
through R
6
, which may be straight chained or branched, contains 1 to 10 carbon atoms, preferably 1 to 9 carbon atoms, more preferably 1 to 6 carbon atoms, and in which each optionally substituted group independently may be substituted by one or more halogen atoms or nitro, cyano, cycloalkyl, preferably C
3-6
cycloalkyl, cycloalkenyl, preferably C
3-6
cycloalkenyl, haloalkyl, preferably C
1-6
haloalkyl, halocycloalkyl, preferably C
3-6
halocycloalkyl, alkoxy, preferably C
1-6
alkoxy, haloalkoxy, preferably C
1-6
haloalkoxy, phenyl, or pyridyl groups, in which the phenyl moiety is optionally substituted by one to three substituents selected from halogen atoms, cyano, C
1-6
alkyl and C
1-6
alkoxy groups.
The invention especially relates to compounds of the general formula I in which R
1
represents a straight-chained or branched C
1-10
alkoxyimino-C
2-10
alkyl, in particular a straight-chained 1-(C
1-6
alkoxyimino)-C
2-6
alkyl group, in which the alkoxy moiety may be unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of halogen atoms, aryl, alkyl, alkoxy, haloalkyl and haloalkoxy groups, most preferably being a 1-(methoxyimino)-ethyl, 1-(methoxyimino)-n-propyl, 1-(ethoxyimino)-ethyl group or a 1-(benzyloxyimino)-ethyl group.
The invention especially relates to compounds of the general formula I in which R
2
represents a C
1-10
alkoxy group, in particular a methoxy group.
The melithiazole derivatives of formula I are oils, gums, or, predominantly, crystalline solid materials and possess valuable fungicidal properties. Besides use as a fungicide for control of diseases in agronomic crops, the compound may be used as a biocide for the control of insect pests and nematodes, as a biocide of human/animal diseases/pests, and as a protectant or preservative for wood, leather or tissue. As fungicides in agronomic crops the compounds of the present invention can protectively and curatively be used against a broad spectrum of diseases in plant and fruit production such as grain producing crops (wheat, barley, rice, rye, triticale, oat, maize, sorghum and others), grape vine plants and fruits, solanaceous crops (potato, tomato, tobacco, pepper and others) top fruit, stone fruits, soft fruits and fruit crops (apples, pears, citrus, mango, bananas, coffee, cocoa and others), oil producing crops (soybeans, sunflowers, groundnuts, rape, olives, palms and others), vegetables (like beans, lettuce, cucumbers, pumpkins, brassicas and others), horticultural plants, hops, sugarbeets, ornamentals, flowers, forestry trees and crops and others. In all crops all parts of the plant can be protected by the compounds including roots, stems, leaves, flowers and fruits. A broad spectrum of diseases belonging to the Oomycetes, Ascomycetes, Basidiomycetes, Hymenomycetes and Fungi Imperfecti are controlled. Examples (but not excluding others) of such diseases are powdery mildews, downy mildews and late blights, anthracnoses, septorioses, blasts and blights, scabs and spots, blotches, rots on fruits, stems, leaves and roots, rusts, alternarioses, cercosporoses, sclerotinioses, moulds, wilts, smuts and bunts and others.
The melithiazole compounds of formula I possess a high fungicidal activity over a wide concentration range. Moreo
Hoefle Gerhard
Rehnig Annerose
Sieverding Gerhard Ewald
Soeker Udo
American Cyanamid Co.
Gerstl Robert
Maurer Barbara V.
Renda Barbara L.
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