Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
1999-11-09
2001-07-10
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C514S089000, C514S091000, C514S095000, C514S099000, C514S383000, C514S407000
Reexamination Certificate
active
06258801
ABSTRACT:
The present invention relates to fungicidal mixtures which comprise
a) a carbamate of the formula I,
where T is CH or N, n is 0, 1 or 2 and R is halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, and where the radicals R may be different if n is 2, and
b) an active compound of the formula II,
where:
Y is hydrogen, a metal atom of the 1st to 3rd main group of the Periodic Table of the Elements or a group NR
3
R
4
R
5
R
6
;
R
2
is hydrogen, a C
1
-C
18
-alkyl group which may be substituted by halogen or a nitro group, a C
2
-C
8
-alkenyl or C
2
-C
8
-alkinyl group which may be substituted by halogen or a nitro group, a C
1
-C
8
-alkoxy-C
1
-C
8
-alkyl or a C
2
-C
8
-alkenyl-C
1
-C
8
-alkyl group, an unsubstituted or substituted aryl group having 6 to 14 carbons, a C
3
-C
7
-cycloalkyl group, a C
1
-C
4
-alkylaryl group or a heterocyclic group having 5 or 6 ring atoms and a hetero atom from the group consisting of N, O and S, where the heterocyclic group is attached directly or via an aliphatic chain to the oxygen atom, and
R
3
-R
6
independently of one another are each a C
1
-C
4
-alkyl group or a C
1
-C
4
-hydroxyalkyl group
in a synergistically effective amount.
Moreover, the invention relates to methods for controlling harmful fungi using mixtures of the compounds I and II and to the use of the compounds I and II for preparing such mixtures.
The compounds of the formula I, their preparation and their action against harmful fungi are disclosed in the literature (WO-A 96/01,256 and 96/01,258).
In the literature, the compounds II are described as fungicides and insecticides (for example DE 24 63 046 and literature cited therein). A known representative of this class of active compounds is commercially available under the common name fosetyl or fosetyl-Al.
Processes for preparing the compounds of the formula II are known per se to the person skilled in the art and therefore do not require any further mention here.
It is an object of the present invention to provide mixtures which have an improved activity against harmful fungi combined with a reduced total amount of active ingredients applied (synergistic mixtures), with a view to reducing the application rates and improving the activity spectrum of the known compounds.
We have found that this object is achieved by the mixtures defined at the outset. Moreover, we have found that applying the compounds I and II simultaneously, i.e. together or separately, or applying the compounds I and II in succession provides better control of harmful fungi than is possible with the individual compounds alone.
The formula I represents, in particular, carbamates in which the combination of the substituents corresponds to one row of the table below:
TABLE 1
No.
T
R
n
I.1
N
2-F
I.2
N
3-F
I.3
N
4-F
I.4
N
2-Cl
I.5
N
3-Cl
I.6
N
4-Cl
I.7
N
2-Br
I.8
N
3-Br
I.9
N
4-Br
I.10
N
2-CH
3
I.11
N
3-CH
3
I.12
N
4-CH
3
I.13
N
2-CH
2
CH
3
I.14
N
3-CH
2
CH
3
I.15
N
4-CH
2
CH
3
I.16
N
2-CH(CH
3
)
2
I.17
N
3-CH(CH
3
)
2
I.18
N
4-CH(CH
3
)
2
I.19
N
2-CF
3
I.20
N
3-CF
3
I.21
N
4-CF
3
I.22
N
2,4-F
2
I.23
N
2,4-Cl
2
I.24
N
3,4-Cl
2
I.25
N
2-Cl, 4-CH
3
I.26
N
3-Cl, 4-CH
3
I.27
CH
2-F
I.28
CH
3-F
I.29
CH
4-F
I.30
CH
2-Cl
I.31
CH
3-Cl
I.32
CH
4-Cl
I.33
CH
2-Br
I.34
CH
3-Br
I.35
CH
4-Br
I.36
CH
2-CH
3
I.37
CH
3-CH
3
I.38
CH
4-CH
3
I.39
CH
2-CH
2
CH
3
I.40
CH
3-CH
2
CH
3
I.41
CH
4-CH
2
CH
3
I.42
CH
2-CH(CH
3
)
2
I.43
CH
3-CH(CH
3
)
2
I.44
CH
4-CH(CH
3
)
2
I.45
CH
2-CF
3
I.46
CH
3-CF
3
I.47
CH
4-CF
3
I.48
CH
2,4-F
2
I.49
CH
2,4-Cl
2
I.50
CH
3,4-Cl
2
I.51
CH
2-Cl, 4-CH
3
I.52
CH
3-Cl, 4-CH
3
Particular preference is given to the compounds I.12, I.23, I.32 and I.38.
The formula II represents in particular compounds in which R
2
is hydrogen or a C
1
-C
4
-alkyl group and in particular an ethyl group (—CH
2
CH
3
) and Y is a metal of the 3rd group of the Periodic Table of the Elements. Suitable metals are also metals of the first and the second main group such as Li, K, Na, Cs, Mg or Ca, to give just some examples.
However, in principle compounds II are suitable in which R
2
and R
3
-R
6
are as defined at the outset.
A particularly preferred compound II is the active compound known under the name fosetyl, or its Al salt fosetyl-Al.
In relation to the C═Y or C═CH or C═N double bonds, the compounds of the formula I can be present in the E or Z configuration (in relation to the carboxylic acid function). Accordingly, they can be used in the mixture according to the invention in each case either as pure E or Z isomers or as E/Z isomer mixture. The E/Z isomer mixture or the Z isomer is preferably used, the Z isomer being especially preferred.
The C═N double bonds of the oxime ether groups in the side chain of the compounds I can exist in each case in the form of pure E or Z isomers or in the form of E/Z isomer mixtures. The compounds I can be used in the mixtures according to the invention both as isomer mixtures and as pure isomers. With a view to their use, particular preference is given to compounds I in which the terminal oxime ether grouping of the side chain is in the cis configuration (OCH
3
to ZR′).
Owing to their basic character, the compounds I are capable of forming salts or adducts with inorganic or organic acids or with metal ions.
Examples of inorganic acids include hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid, carboxylic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two sulfo groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphoric acid radicals), it being possible for the alkyl or aryl radicals to carry further substituents, e.g. p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
Suitable metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, and of the first to eighth sub-group, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Especially preferred are the metal ions of the elements of the sub-groups of the fourth period. The metals can exist in the various valencies which they can assume.
When preparing the mixtures, it is preferred to employ the pure active ingredients I and II, to which further ingredients active against harmful fungi or other pests, such as insects, arachnids or nematodes, or herbicidal or growth-regulating active ingredients or fertilizers can be admixed, if so required.
The mixtures of the compounds I and II, or the simultaneous joint or separate use of the compounds I and II, have outstanding action against a wide spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can therefore also be employed as foliar- and soil-acting fungicides.
They are especially important for controlling a large number of fungi in a variety of crop plants, such as cotton, vegetable species (e.g. cucumbers, beans and cucurbits), barley, grass, oats, coffee, maize, fruit species, rice, rye, soya, grapevine, wheat, ornamentals, sugar cane, and a variety of seeds.
They are particularly suitable for controlling the following phytopathogenic fungi:
Erysiphe graminis
(powdery mildew) in cereals,
Er
Ammermann Eberhard
Birner Erich
Leyendecker Joachim
Lorenz Gisela
Muller Bernd
BASF Aktiengesellshcaft
Keil & Weinkauf
Robinson Allen J.
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