Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-11-02
2002-08-20
Webman, Edward J. (Department: 1617)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S365000
Reexamination Certificate
active
06436979
ABSTRACT:
The present invention relates to fungicidal mixtures which comprise at least one compound selected from
a
1
) carbamates of the formula I,
in which 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, where the radicals R may 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 active compound of the formula IV,
where the substituents R
1
to R
3
have the following meaning:
R
1
is C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, C
1
-C
4
-alkyl-C
3
-C
7
-cycloalkyl, where these radicals may carry substituents selected from the group consisting of halogen, cyano and C
1
-C
4
-alkoxy, and is also C
1
-C
4
-alkoxy,
R
2
is C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl,
R
3
is hydrogen, halogen, 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,
Y is O, S, CHR
4
or NR
5
, where R
4
and R
5
may each have the meanings mentioned for R
2
,
n is 0, 1, 2 or 3,
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 preparing such mixtures.
The compounds of the formula I, their preparation and their action against harmful fungi are known from the literature (WO-A 96/01,256 and 96/01,258).
The compounds of the formulae II and III, their preparation and their action against harmful fungi are known from the literature (EP-A 253 213, EP-A 398 692 and EP-A 477631).
The compounds of the formula IV and also processes for their preparation are described in JP-A 09/323984. Moreover, they can be prepared using the processes described in DE 1 95 31 814.
It is an object of the present invention to provide mixtures which have improved activity against harmful fungi combined with a reduced total amount of active compounds applied (synergistic mixtures), with a view to reducing the application rates and to 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 better control of harmful fungi is possible by applying the compounds I and/or II and/or III and IV simultaneously, that is either together or separately, or by applying the compounds I and/or II and/or III and IV in succession then when the individual compounds are used.
The formula I represents in particular carbamates in which the combination of the substituents corresponds to a row of the following table:
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 exist 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 mixtures. The E/Z isomer mixture or the Z isomer is preferably used, the Z isomer being particularly 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 as 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 present 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, carbonic 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 with 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 with 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, 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 subgroup, in particular chromium, manganese, iron, cobalt, nickel, copper and zinc, and others. Particular preference is given to 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, preference is given to those in which R
1
is C
1
-C
4
-alkyl (methyl, ethyl, n- and i-propyl and t-butyl), C
1
-C
4
-alkylene-C
3
-C7-cycloalkyl, C
1
-C
4
-alkenyl (in particular ethenyl, propenyl and butenyl which may be substituted in particular by halogen (preferably Cl)), propynyl, cyanomethyl and methoxymethyl. Among the C
1
-C
4
-alkylene-C
3
-C
7
-cycloalkyl substituents, particular preference is given to methylene-substituted compounds, in particular to methylenecyclopropyl, methylenecyclopentyl, methylenecyclohexyl and methylenecyclohexenyl. The rings of these substituents may be substituted, preferably by halogen. Particular preference is given to i-propyl.
A preferred substituent R
2
is C
1
-C
4
-alkyl (in particular methyl, ethyl, i-propyl or n-, i- or t-butyl). Particular preference is given to i-propyl.
Preferred substituents R
3
and R
4
are hydrogen, F, Cl, methyl, ethyl, methoxy, thiomethyl and N-methylamino, in particular F or Cl.
Preferred compounds of the formula IV are shown in JP-A 09/329984, which has already been mentioned. Particular preference is given to the compound of the formula IV/1.
When preparing the mixtures, it is preferred to employ the pure active compounds I, II and/or III and IV, with which further active compounds against harmful fungi or other pests, such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active compounds or fertilizers can be admixed as required.
The mixtures of the compounds I, II and/or III and IV, or the simultaneous joint or separate use of the compounds I, II and/or III and IV, have outstanding action against a wide range of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycet
Ammermann Eberhard
Eicken Karl
Grote Thomas
Lorenz Gisela
Saur Reinhold
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