Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-06-21
2003-04-01
Qazi, Sabiha (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S312000, C514S407000, C514S236200, C514S239500, C514S317000
Reexamination Certificate
active
06541500
ABSTRACT:
This application is a 371 of PCT/EP99/09812, filed on Dec. 11, 1999 which claims priority of DE 19859250.7 filed on Dec. 22, 1998.
The present invention relates to a fungicidal mixture comprising
a) a compound of the formula I
its N-oxide or one of its salts where:
R
1
, R
2
, R
3
, R
4
independently of one another are: hydrogen, hydroxyl, nitro, 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
-haloalkylthio;
R
5
, R
6
, R
7
independently of one another are: hydrogen, hydroxyl, cyano, nitro, halogen, C
1
-C
7
-alkyl, C
1
-C
7
-haloalkyl, C
1
-C
7
-alkoxy, C
1
-C
7
-haloalkoxy, C
1
-C
7
-alkylthio, C
1
-C
7
-haloalkylthio, C
1
-C
7
-hydroxyalkyl, C
2
-C
4
-acyl, aryl, aryloxy, where the radicals with aryl may for their part carry one to three of the following groups: cyano, nitro, 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 and C
1
-C
4
-haloalkylthio, and
b) a compound of the formula II,
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,
in a synergistically effective amount.
Moreover, the invention relates to methods for controlling harmful fungi using the compounds I and the compounds II or synergistic mixtures comprising them, and to the use of the compounds I or the compounds II for preparing such mixtures.
Compounds of the formula I, their fungicidal action and their preparation are known from U.S. Pat. No. 5,240,940 and from ACS Sympos. Ser. 443, page 538 to page 552 (1991).
The compounds of the formula II, their preparation and their action against harmful fungi are likewise known from the literature (WO-A 96/01,256 and 96/01,258).
It is an object of the present invention to provide mixtures which, at a reduced total amount of active compounds applied, have an improved action against harmful fungi (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. Furthermore, we have found that, if the compounds I and the compounds II are applied simultaneously, i.e. jointly or separately, or if the compounds I and the compounds II are applied successively, harmful fungi can be controlled better than with the compounds I or II on their own.
Owing to the basic character of the nitrogen ring atom or the NH grouping, the compounds I and II are capable of forming salts with inorganic or organic acids or with metal ions.
Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid or carbonic 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 from 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 from 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-toluene sulfonic 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, the third and fourth main group, in particular aluminum, tin and lead, and the first to eighth sub-group, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc. Particular preference is given to 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.
Furthermore, the compounds I can be converted in a manner known per se into the N-oxides (cf. U.S. Pat. No. 5,240,940).
With respect to the C═Y or C═CH or C═N double bonds, the compounds of the formula II can be present in the E or the Z configuration (with respect 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. Preference is given to using the E/Z isomer mixture or the Z isomer, and particular preference is given to the Z isomer.
The C═N double bonds of the oxime ether groupings in the side chain of the compounds II can in each case be present as pure E or Z isomers or as E/Z isomer mixtures. The compounds II can be used in the mixtures according to the invention both as isomer mixtures and as pure isomers. With respect to their use, particular preference is given to compounds II in which the terminal oxime ether grouping of the side chain is present in the cis configuration (OCH
3
to COOCH
3
).
For providing the fungicidal mixtures according to the invention, preference is given to using compounds I, their salts or N-oxides in which:
R
1
, R
2
, R
3
, R
4
independently of one another are hydrogen, halogen, C
1
-C
2
-alkyl, C
1
-C
2
-haloalkyl, C
1
-C
2
-alkoxy, C
1
-C
2
-haloalkoxy or C
1
-C
2
-alkylthio;
R
5
, R
6
, R
7
independently of one another are hydrogen, nitro, cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or phenyl.
With respect to the suitability for use as mixing partners, particular preference is given to the compounds Ia of Table 1 below.
TABLE 1
(Ia)
No.
R
1
R
2
R
3
R
4
R
5
I.1
H
H
Cl
H
2-F
I.2
H
H
Cl
H
2-C(CH
3
)
3
I.3
H
H
Cl
H
2-CH
3
I.4
H
H
Cl
H
2-OCH
3
I.5
H
H
Cl
H
3-F
I.6
H
H
Cl
H
3-Cl
I.7
H
H
Cl
H
3-CF
3
I.8
H
H
Cl
H
3-CN
I.9
H
H
Cl
H
3-OCH
3
I.10
H
H
Cl
H
3-phenyl
I.11
H
H
Cl
H
4-Cl
I.12
H
H
Cl
H
4-Br
I.13
H
H
Cl
H
4-CF
3
I.14
H
H
Cl
H
4-CH
3
I.15
H
H
Cl
H
4-CH(CH
3
)
2
I.16
H
H
Cl
H
4-CN
I.17
H
H
Cl
H
2-Cl-4-F
I.18
H
H
Cl
H
2,4-di-Br
I.19
H
H
Cl
H
2,4-di-NO
2
I.20
H
H
Cl
H
2-CH
3
-4-F
I.21
H
H
Cl
H
2,6-di-F
I.22
H
H
Cl
H
2,4,6-tri-CH
3
I.23
F
H
H
H
4-F
I.24
Cl
H
H
H
4-F
I.25
NO
2
H
H
H
4-F
I.26
H
F
H
H
4-F
I.27
H
Cl
H
H
4-F
I.28
H
CH
3
H
H
4-F
I.29
H
NO
2
H
H
4-F
I.30
H
OC
2
H
5
H
H
4-F
I.31
H
H
F
H
4-F
I.32
H
H
Cl
H
4-F
I.33
H
H
Br
H
4-F
I.34
H
H
NO
2
H
4-F
I.35
H
H
OCF
3
H
4-F
I.36
H
H
C
2
H
5
H
4-F
I.37
H
H
SCF
3
H
4-F
I.38
H
H
O—C
2
H
5
H
4-F
I.39
H
H
H
F
4-F
I.40
H
H
H
Cl
4-F
I.41
H
H
H
CF3
4-F
I.42
F
H
F
H
4-F
I.43
O—CH
3
H
O—CH
3
H
4-F
I.44
Cl
F
H
H
4-F
I.45
Cl
Cl
H
H
4-F
I.46
Cl
CH
3
H
H
4-F
I.47
H
Br
H
Cl
4-F
I.48
H
Cl
H
OH
4-F
I.49
H
O—CH
3
H
NO
2
4-F
I.50
H
F
Cl
H
4-F
I.51
H
CH
3
Cl
H
4-F
I.52
H
H
Cl
Cl
4-F
I.53
Cl
H
H
Cl
4-F
I.54
Cl
F
Cl
H
4-F
I.55
H
H
Cl
CN
4-F
I.56
Cl
CH
3
Cl
H
4-F
I.57
Cl
Cl
Cl
H
4-F
I.58
Cl
Cl
Cl
Cl
4-F
I.59
H
H
H
Cl
2-F-4-Br
I.60
H
H
H
Cl
2,3-di-CH
3
I.61
H
H
H
Cl
2-F-4-Cl
I.62
H
H
H
Cl
2,4-di-Cl-6-F
I.63
H
H
H
Cl
2,4-di-F
I.64
H
H
H
Cl
2,4-di-CH
3
I.65
H
H
H
Cl
2-C
2
H
5
I.66
H
H
H
Cl
2-CH
3
-4-F
I.67
H
H
H
Cl
3-CH
3
-4-Cl
I.68
H
H
Cl
H
H
I.69
Cl
H
Cl
H
H
I.70
H
H
Cl
H
4-C(CH
3
)
3
Very particular preference is given to the compounds Ia of Table 2 and to the hydrochloride and the N-oxide of the compound 8 mentioned therein.
TABLE 2
No.
R
1
R
2
R
3
R
4
R
5
1.71
H
H
Cl
H
2-Cl
1.72
H
H
Cl
H
2-Br
1.73
H
H
Cl
H
2-CN
1.74
H
H
Cl
H
2-CF
3
1.75
H
H
Cl
H
2-NO
2
1.76
H
H
Cl
H
4-F
1.77
H
H
Cl
H
2,4-di-F
1.78
Cl
H
Cl
H
4-F
1.79
H
H
H
Cl
2-Cl-4-F
1.80
CH
3
H
CH
3
H
4-F
The compounds of the formula Ia mentioned in or under Tables 1 and 2 are known from U.S. Pat. No. 5,240,940 and/or ACS Sympos. Ser. 443, page 538 to page 552 (1991). Compound I.78 of Table 2 is known
Ammermann Eberhard
Appel Josef
Grote Thomas
Leyendecker Joachim
Lorenz Gisela
BASF - Aktiengesellschaft
Keil & Weinkauf
Qazi Sabiha
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