Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-01-16
2003-09-16
Pryor, Alton (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S184000, C514S229200, C514S309000
Reexamination Certificate
active
06620822
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel active compound combinations which comprise the known 5,7-dichloro-4-(4-fluoro-phenoxy)-quinoline on the one hand and other known fungicidally active compounds on the other hand, and which are highly suitable for controlling phytopathogenic fungi.
BACKGROUND OF THE INVENTION
It is already known that 5,7-dichloro-4-(4-fluoro-phenoxy)-quinoline has fungicidal properties (cf. EP-A 0 326 330). The activity of this substance is good; however, at low application rates it is in some cases unsatisfactory.
Furthermore, it is already known that certain combinations of 5,7-dichloro-4-(4-fluoro-phenoxy)-quinoline with other known fungicidally active compounds can be employed for controlling fungi (cf. EP-A 0 326 330, WO 96/18 299 and WO 98/51 146). However, the activity of these mixtures is likewise not always satisfactory.
SUMMARY OF THE INVENTION
Compositions comprising a 5,7-dichloro-4-(4-fluoro-phenoxy)-quinoline of formula (I)
and at least one the compounds represented by formulae (II) to (IX) as given herein below are provided. The compositions have fungicidal activity.
DETAILED DESCRIPTION OF THE INVENTION
It has now been found that the novel active compound combinations comprising
5,7-dichloro-4-(4-fluoro-phenoxy)-quinoline of the formula
and
(1) a triazole derivative of the formula
in which
X represents chlorine or phenyl,
or
(2) the N-dichloro-fluoro-methylthio-N′,N′-dimethyl-N-p-tolylsulfamide of the formula
or
(3) the zinc propylene-1,2-bis-(dithiocarbamidate) of the formula
or
(4) the aniline derivative of the formula
or
(5) the compound of the formula
or
(6) the 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione of the formula
or
(7) the compound of the formula
or
(8) the benzimidazole derivative of the formula
have very good 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. Thus an unforeseeable, true synergistic effect is present, and not just an addition of activities.
The 5,7-dichloro-4-(4-fluoro-phenoxy)-quinoline of the formula (I) is known (cf. EP-A 0 326 330).
The formula (II) includes the compounds
1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of the formula
and
1-(4-phenyl-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of the formula
The 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione can be present in the “thiono” form of the formula
or in the tautomeric “mercapto” form of the formula
For the sake of simplicity, only the “thiono” form is shown in each case.
The fungicidal components which are present in the active compound combinations according to the invention in addition to the 5,7-dichloro-4-(4-fluoro-phenoxy)-quinoline of the formula (I) are likewise known. Specifically, the active compounds are described in the following publications:
(1) Compounds of the formula (II)
DE-A 2 324 010
(2) Compound of the formula (III)
Pesticide Manual, 11
th
Edition, page 1208
(3) Compound of the formula (IV)
Pesticide Manual, 11
th
Edition, page 608
(4) Compound of the formula (V)
EP-A 0339418
(5) Compound of the formula (VI)
EP-A 0 472 996
(6) Compound of the formula (VII)
WO 96/16048
(7) Compound of the formula (VIII)
EP-A 0 882 043
(8) Compound of the formula (IX)
WO 97/06171
In addition to the active compound of the formula (I), the active compound combinations according to the invention comprise at least one active compound of the compounds from groups (1) to (8).
The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios 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 5 parts by weight, of active compound of group (1),
from 1 to 50 parts by weight, preferably from 2 to 10 parts by weight, of active compound of group (2),
from 1 to 50 parts by weight, preferably from 2 to 10 parts by weight, of active compound of group (3),
from 0.1 to 10 parts by weight, preferably from 0.2 to 5 parts by weight, of active compound of group (4),
from 0.1 to 10 parts by weight, preferably from 0.2 to 5 parts by weight, of active compound of group (5),
from 0.1 to 10 parts by weight, preferably from 0.2 to 5 parts by weight, of active compound of group (6),
from 0.05 to 10 parts by weight, preferably from 0.1 to 5 parts by weight, of active compound of group (7) and/or
from 0.05 to 10 parts by weight, preferably from 0.1 to 5 parts by weight, of active compound of group (8)
are employed 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 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 controlling cereal diseases, such as Erysiphe, Puccinia and Septoria, and for controlling diseases encountered in viticulture, such as Uncinula, Plasmopara and Botrytis, and furthermore in dicotyledonous crops for controlling powdery and downy mildew fungi and causative organisms of leaf spot.
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 employed for foliar application or else as seed dressings.
The active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, microencapsulations in polymeric substances and into coating compositions for seed, 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. Suitable liquid solvents include, essentially: 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 sawdus
Dutzmann Stefan
Mauler-Machnik Astrid
Stenzel Klaus
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Henderson Richard E. L.
Mrozinski, Jr. John E.
Pryor Alton
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