Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-11-17
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...
C514S406000, C514S407000, C514S438000, C514S539000, C514S521000, C514S617000, C514S619000
Reexamination Certificate
active
06444692
ABSTRACT:
The present invention relates to a fungicidal mixture, comprising at least one compound selected from
a
1
) carbamates 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, it being possible for the radicals R to be different if n is 2,
a
2
) the oxime ether carboxylate of the formula II
or
a
3
) the oxime ether carboxamide of the formula III,
and
b) at least one compound of the formula IV,
where the substituents X
1
to X
5
and R
1
to R
4
have the following meanings:
X
1
to X
5
independently of each other are each hydrogen, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-thioalkoxy, C
1
-C
4
-sulfonylalkyl, nitro, amino, N-C
1
-C
4
-carboxylamino, N-C
1
-C
4
-alkylamino;
R
1
is C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkinyl, C
1
-C
4
-alkyl-C
3
-C
7
-cycloalkyl, it being possible for these radicals to carry substituents selected from the group consisting of halogen, cyano, and C
1
-C
4
-alkoxy,
R
2
is a phenyl radical or a 5- or 6-membered saturated or unsaturated heterocyclyl radical having at least one hetero atom selected from the group consisting of N, O and S, it being possible for the cyclic radicals to have one to three substituents selected from the group consisting of halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkoxy-C
2
-C
4
-alkenyl, C
1
-C
4
-alkoxy-C
2
-C
4
-alkinyl,
R
3
and R
4
independently of each other are each hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, N-C
1
-C
4
-alkylamino, C
1
-C
4
-haloalkyl or C
1
-C
4
-haloalkoxy
in a synergistically effective amount.
Moreover, the invention relates to methods for controlling harmful fungi using mixtures of the compounds I, II and/or III and IV and to the use of the compounds I, II and/or III and IV for the preparation of such mixtures.
The compounds of the formula I, their preparation and their activity against harmful fungi are disclosed in the literature (WO-A 96/01,256 and 96/01,258).
The compounds of the formula II and III, their preparation and their activity against harmful fungi are disclosed in the literature (EP-A 253 213, EP-A 398 692 and EP-A 477631).
The compounds of the formula IV and processes for their preparation are described in WO-A 96/19442.
It was 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 rates of application and to improving the spectrum of action of the known compounds.
Accordingly, we have found that this object is achieved by the mixtures defined at the outset. Moreover, we have found that better control of the harmful fungi is possible by applying the compounds I and II and/or III simultaneously together or separately, or by applying the compounds I and II and/or III in succession, than when the individual compounds are used.
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.
In relation to the C═Y or C═CH or C═N double bonds, the compounds of the formulae I to III can be present in the E or the 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 in the form of the pure E or Z isomers or in the form of an 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 to III can exist in each case in the form of pure E or Z isomers or as E/Z isomer mixtures. The compounds I to III can be used in the mixtures according to the invention both as isomer mixtures and as pure isomers. With a view to their use, compounds I to III which are particularly preferred are those where the terminal oxime ether group in the side chain is in the cis configuration (OCH
3
to ZR′).
Owing to their basic character, the compounds I to III are capable of forming salts or adducts with inorganic or organic acids or with metal ions.
Examples of inorganic acids are 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 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 phosphonic acid radicals), it being possible for the alkyl or aryl radicals to carry further substituents, for example 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 subgroup, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Especially preferred are the metal ions of the elements of the subgroups of the fourth period. The metals can exist in the various valences which they can assume.
Among the compounds of the formula IV, those are preferred where X
1
is a C
1
-C
4
-haloalkyl group, in particular a trifluoromethyl group, and X
2
and X
3
are hydrogen or a halogen group, in particular hydrogen. X
4
and X
5
are preferably hydrogen, halogen (in particular C
1
or F), C
1
-C
4
-alkoxy (in particular methoxy or ethoxy), C
1
-C
4
-alkylthio (in particular methylthio or ethylthio), C
1
-C
4
-haloalkyl (in particular trifluoromethyl) or C
1
-C
4
-haloalkoxy (in particular trifluoromethoxy).
Preferred substituents R
1
are C
1
-C
4
-alkyl (methyl, ethyl, n- and i-propyl and t-butyl), C
1
-C
4
-alkylene-C
3
-C
7
-cycloalkyl, C
1
-C
4
-alkenyl (in particular ethenyl, propenyl and butenyl, in particular those which may be substituted by halogen (preferably Cl)), propinyl, cyanomethyl and methoxymethyl. Among the C
1
-C
4
-alkylene-C
3
-C
7
-cycloalkyl substituents, preference is given in particular to methylene-substituted compounds, in particular methylenecyclopropyl, methylenecyclopentyl, methylenecyclohexyl and methylenecyclohexenyl. The rings of these substituents may be substituted, preferably by halogen.
Suitable substituents R
2
are, in addition to phenyl (unsubstituted or substituted), in
Ammermann Eberhard
Birner Erich
Leyendecker Joachim
Lorenz Gisela
Möller Bernd
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
LandOfFree
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