Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-07-30
2002-09-03
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...
C514S478000, C514S479000
Reexamination Certificate
active
06444693
ABSTRACT:
The present application relates to novel active compound combinations comprising on the one hand valinamide derivatives and on the other hand fenamidone and which are highly suitable for controlling phytopathogenic fungi.
It is already known that valinamide derivatives have fungicidal properties (cf. EP-A 472 996). The activity of this substance is good; however at low application rates it is sometimes unsatisfactory.
Furthermore, it is already known that fenamidone can be employed for controlling fungi (cf. EP-A 0 629 616). However, the activity of fenamidone at low application rates is not always satisfactory.
It has now been found that the novel active compound combinations of valinamide derivatives of the general formula (I)
in which
R
1
represents i-propyl or s-butyl and
R
2
represents chlorine, methyl, ethyl or methoxy, and
fenamidone of the formula (II)
have very good fungicidal properties.
Surprisingly, the fungicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds. This is an unforeseeable true synergistic effect and not just a complementation of action.
From the structural formula for the active compounds of the formula (I) it can be seen that the compounds have two asymmetrically substituted carbon atoms. The product can therefore be present as a mixture of various isomers or else in the form of an individual isomer.
Preferred compounds of the formula (I) are compounds in which the amino acid moiety is formed by i-propyloxycarbonyl-L-valine or sec-butyloxycarbonyl-L-valine and the phenethylamine moiety is either racemic or has the S-(−)-configuration, but in particular the R-(+)-configuration.
Particularly preferred compounds of the formula (I) are the compounds in which
R
1
represents i-propyl.
In particular, the compounds
1-methylethyl [2-methyl-1-[[[-1-(4-chlorophenyl)ethyl]amino]carbonyl]-propyl]-carbamate of the formula (Ia)
1-methylethyl [2-methyl-1-[[[-1-(4-methylphenyl)ethyl]amino]carbonyl]-propyl]-carbamate of the formula (Ib)
1-methylethyl [2-methyl-1-[[[-1-(4-ethylphenyl)ethyl]amino]carbonyl]-propyl]-carbamate of the formula (Ic)
and 1-methylethyl [2-methyl-1-[[[-1-(4-methoxyphenyl)ethyl]amino]carbonyl]-propyl]-carbamate of the formula (Id)
and their isomers, as mentioned above, may be mentioned.
The active compounds of the formula (I) are known (cf. EP-A-0 472 996).
The fungicidally active compound fenamidone, which is furthermore present in the combinations according to the invention, is also known (cf. EP-A 0 629 616).
In addition to at least one active compound of the formula (I), the active compound combinations according to the invention comprise the active compound fenamidone of the formula (II). They may additionally also comprise other fungicidally active admixture components.
If the active compounds in the active compound combinations according to the invention are present in certain ratios by weight, the synergistic effect is particularly pronounced. However, the ratios by weight of the active compounds in the active compound combinations can be varied within a relatively wide range. In general,
from 0.1 to 10 parts by weight, preferably
from 0.2 to 2 parts by weight of active compound of the formula (II)
are present per part by weight of active compound of the formula (I).
The active compound combinations according to the invention have very good fungicidal properties and can be employed in particular for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
The active compound combinations according to the invention are particularly suitable for the protective control of Phytophthora infestans and Alternaria spec. on tomatoes and potatoes, and of Plasopara viticola on grapevines.
The fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
The active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
These formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
In the formulations, the active compound combinations according to the invention can be present as a mixture with other active compounds such as fungicides, insecticides, acaricides and herbicides, and as mixtures with fertilizers or plant growth regulators.
Mixing partners for such mixtures are, for example:
Fungicides
2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl- 1,3-thiazole-5-carboxanilide; 2,6-dichloro-N-(4-trifluoromethylbenz
Seitz Thomas
Stenzel Klaus
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Gil Joseph C.
Harmuth Raymond J.
Robinson Allen J.
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