Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-03-03
2001-01-16
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S399000
Reexamination Certificate
active
06174911
ABSTRACT:
Synergistic antifungal compositions comprising imazalil, a salt, a stereoisomer or stereoisomeric mixture thereof, and epoxiconazole, a salt, stereoisomer or stereoisomeric mixture thereof, for protecting plants, fruits or seeds. Use of said compositions to protect plants or fruits against fungi.
Various classes of compounds are known as antimicrobial and in particular antifungal compounds. Among these classes, the group of imidazole and triazole derivatives is of particular interest and several of such compounds are now widely used as antimicrobials and in particular as antifungals.
Further, there are known fungicidal combinations comprising two or more such fungicidally active compounds. DE-A-2916853 describes a combination of fenfuran, thiabendazole and imazalil for treating cereal grains. DE-A-2922292 describes combinations of a furan-3-carboxamide, imazalil and/or thiabendazole. DE-A-2823818 describes mixtures of 2,4,5-trimethyl-N-phenyl-3-furancarboxamide with imazalil and/or thiabendazole. And EP-0,336,489, describes synergistic compositions of imazalil and propiconazole.
It now has been found that the compounds imazalil and epoxiconazole act synergistically.
The present invention is concerned with mixtures or compositions comprising imazalil (I), a salt, a stereoisomer or stereoisomeric mixture thereof, and epoxiconazole (II), a salt, a stereoisomer or stereoisomeric mixture thereof, in quantities producing a mutual synergistic antifungal effect, and a carrier.
Imazalil as mentioned hereinabove is the generic name of the compound (±)-1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole, which compound may be represented by the formula
This compound, its synthesis as well as its antifungal properties are described in U.S. Pat. No. 3,658,813.
Epoxiconazole, also known as BAS 480F, is the generic name of the compound cis-(±)-1-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole, which compound may be represented by the formula
This compound, its synthesis as well as its antifungal properties are described in EP-A-0,196,038.
The active ingredients (I) and (II) for use in the mixtures or compositions according to the present invention may be used as stereochemical mixtures or as pure stereoisomers.
The active ingredients (I) and (II) may be present in base or in salt form, the latter being obtained by reaction of the base form with an appropriate acid. Appropriate acids comprise, for example, inorganic acids, such as the hydrohalic acids, i.e. hydrofluoric, hydrochloric, hydrobromic and hydroiodic, sulfuric acid, nitric acid, phosphoric acid, phosphinic acid and the like; or organic acids, such as, for example, acetic, propanoic, hydroxyacetic, 2-hydroxypropanoic, 2-oxopropanoic, ethanedioic, propanedioic, butanedioic, (Z)-2-butenedioic, (E)-2-butenedioic, 2-hydroxybutanedioic, 2,3-dihydroxybutanedioic, 2-hydroxy-1,2,3-propanetricarboxylic, methanesulfonic, ethanesulfonic, benzenesulfonic, 4methylbenzenesulfonic, cyclohexanesulfamic, 2-hydroxybenzoic, 4-amino-2-hydroxybenzoic and the like acids.
Particular salt forms of imazalil (I) are the sulfate, phosphate, acetate, nitrate or phosphite salts.
The term salt form also comprises metal complexes which the basic components (I) or (II) may form. One of the components may occur as a complex and the other not; or both components may occur as a complex. Metal complexes as mentioned above consist of a complex formed between one or more molecules of the active ingredient and one or more organic or inorganic metal salt or salts. Examples of said organic or inorganic salts comprise the halogenides, nitrates, sulfates, phosphates, acetates, trifluoroacetates, trichloroacetates, propionates, tartrates, sulfonates, e.g. methylsulfonates, 4-methylphenylsulfonates, salicylates, benzoates and the like of the metals of the second main group of the periodical system, e.g. the magnesium or calcium salts, of the third or fourth main group, e.g. aluminium, tin, lead as well as the first to the eighth transition groups of the periodical system such as, for example, chromium, manganese, iron, cobalt, nickel, copper, zinc and the like. Preferred are the metals pertaining to the transition elements of the fourth period. The metals may be present in each of their possible valences. The metal ions may be present in any of their possible valences, the most preferred metal copper being most advantageously used in its divalent form Cu(II). Suitable copper compounds are copper sulfate, acetate, hydroxide, oxide, borate, fluoride and in particular copper hydroxide carbonate Cu(OH)
2
CuCO
3
. The complexes can be mono- or polynuclear, they may contain one or more parts of the organic molecule as ligands.
The term salt as used hereinabove also comprises the solvates which the-active ingredients of formula (I) and (II) are able to form. Examples of such solvates are e.g., the hydrates, alcoholates and the like.
The ratio between the active ingredients of formula (I) and (II) may vary within relatively broad ranges and will be dependent on the application aimed at, however said ratio will be so that both active ingredients act synergistically. Particularly, it is contemplated that the compositions of the present invention comprise at least 750 mg/l of (I), and at least 187.5 mg/l of (II). In particular, said compositions comprise (I) in a concentraction between 750 mg/l and 1500 mg/l and (II) in a concentration between 187.5 mg/l and 750 mg/l. Said concentrations of (I) and (II) are taken as their base equivalent.
The quantity of each of the active ingredients in the compositions according to the present invention will be so that a synergistic antifungal effect is obtained. In particular, it is contemplated that in the compositions to be used directly to the plants or the loci thereof, the concentration of imazalil, taken as base equivalent, will be from 750 mg/l to 1500 mg/l; the concentration of epoxiconazole taken as base equivalent is contemplated to be in the range from 187.5 mg/l to 750 mg/l. The active ingredients can be formulated in waxes for use as a cover or coating of e.g. fruits, in particular citrus fruits. Said active ingredients can also be used in all kind of aqueous treatment systems. The said compositions to be used can be obtained from concentrates, such as e.g. emulsifiable concentrates, suspension concentrates, or soluble concentrates, upon dilution with aqueous or organic media, such concentrates being intended to be covered by the term composition as used in the definitions of the present invention.
An emulsifiable concentrate is a liquid, homogeneous formulation of the active ingredients of formula (I) and (II) to be applied as an emulsion after dilution in water. A suspension concentrate is a stable suspension of the active ingredients in a fluid intended for dilution with water before use. A soluble concentrate is a liquid, homogeneous formulation to be applied as a true solution of the active ingredients after dilution in water.
The synergistic mixtures of the present invention are active against a broad range of fungi. As examples of such fungi there may be named Ascomycetes (e.g.
Venturia, Podosphaera, Erysiphe, Monilinia, Uncinula, Aureobasidium, Scierophoma
); Basidiomycetes (e.g.
Hemileia, Rhizoctonia, Puccinia, Coniophora, Serpula, Poria, Uromyces, Gloeophyllum, Lentinus, Coriolus, Irpex
); Fungi imperfecti (e.g.
Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia, Penicillium, Geotrichum
).
The synergistic mixtures according to the present invention possess advantageous curative, preventive and systemic fungicidal activity to protect plants, in particular culture plants. The present mixtures can be used to protect plants or parts of plants, e.g. fruits, blossoms, flowers, foliage, stems, roots, tubers of plants or culture plants infected, harmed or destroyed by microorganisms, whereby later-growing parts of plants are protected against such microorganisms.
The mixtures according to the present in
Bosselaers Jan Pieter Hendrik
Garnier Alain Joseph Jean Florimond
Janssen Pharmaceutica N.V.
Robinson Allen J.
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