Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-01-18
2001-01-23
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...
C514S312000, C514S383000
Reexamination Certificate
active
06177446
ABSTRACT:
The present invention relates to a fungicidal mixture comprising
a) a compound of the formula I
an N-oxide or a salt thereof, where the radicals are defined as follows:
R
1
,R
2
,R
3
and 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
and 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 or aryloxy, it being possible for the radicals with aryl to have attached to them, in turn, one to three of the following groups: cyano, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
l
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio and C
1
-C
4
-haloalkylthio, or
b) a compound of the formula II,
where the radicals are defined as follows:
R
8
is phenyl which can have attached to it one to three of the following groups: cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
2
-haloalkyl and C
1
-C
4
-alkoxy, or pyrimidyl which can have attached to it a C
1
-C
3
-alkyl group and/or a phenoxy group, it being possible for the phenoxy group to have attached to it, in turn, one to three of the following substituents: cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
2
-haloalkyl and C
1
-C
4
-alkoxy;
A is oxygen or oxymethylene (—OCH
2
—);
X is CH or N;
Y is oxygen or NR, where R is hydrogen, C
1
-C
3
-alkyl or C
1
-C
3
-alkoxy, or
c) a pyrimidine derivative of the formula III
or a salt thereof: where the radical R
9
is methyl, propyn-1-yl or cyclopropyl, or
d) (2RS,3SR)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole (IV)
e) a compound of the formula V
in which the radicals are as defined below:
R
10
is fluorine or chlorine;
R
11
is trifluoromethyl or chlorine, or
R
10
and R
11
together are a group —OCF
2
O—,
in a synergistically active amount.
The invention furthermore relates to methods of controlling fungal pests using the compounds I and a compound II to V, or synergistic mixtures comprising them, and to the use of the compounds I, or the compounds II to V, for the preparation of such mixtures.
U.S. Pat. No. 5,240,940 and ACS Sympos. Ser. 443, page 538 to page 552 (1991) disclose compounds of the formula I, their fungicidal action and their preparation.
The literature (EP-A 253 213, EP-A 382 375, EP-A 398 692, EP-A 400 417) also discloses compounds of the formula II, their preparation and their action against fungal pests.
Also known are the pyrimidine derivatives III, their preparation and their action against fungal pests [R
9
=methyl: DD-A 151 404 (common name: pyrimethanil); R
9
=1-propynyl: EP-A 224 339 (common name: mepanipyrim); R
9
=cyclopropyl: EP-A 310 550 (common name: cyprodinil)].
EP-A 196 038 discloses (2RS,3SR)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole (IV) (INN name: epoxiconazole).
EP-A 318 704 (R
10
=F, R
11
=CF
3
), EP-A 206 999 (R
10
, R
11
=—O—CF
2
—O—: common name: fludioxonil) and EP-A 182 738 (R
10
, R
11
=chlorine: common name: fenpiclonil) also disclose the compounds of the general formula V.
With a view to reducing the rates of application and to improving the spectrum of action of the known compounds, it is an object of the present invention to provide mixtures which have an improved activity against fungal pests while the total amount of active ingredients applied is reduced (synergistic mixtures).
We have found that this object is achieved by the mixtures defined at the outset. Moreover, it has been found that fungal pests can be controlled more efficiently when the compounds I and the compounds II to V are applied simultaneously, i.e. jointly or separately, or when the compounds I and the compounds II to V are applied in succession, than when the compounds I or II to V are used alone.
Relative to the C═X double bond, the compounds of the formula II can exist in the E or the Z configuration (relative to the OCH
3
and CO—YCH
3
group). Accordingly, they can be used in the mixture according to the invention either in the form of the pure isomers or in the form of a mixture of E/Z isomers. The mixture of E/Z isomers or the E isomer is preferably used, the E isomer being particularly preferred in many cases.
Due to the basic character of the ring nitrogen atom or the NH group, the compounds I and III 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.
Suitable organic acids are, for example, formic acid, carbonic 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 having 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals such as phenyl and naphthyl which have attached to them one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals such as phenyl and naphthyl which have attached to them one or two phosphoric acid radicals), it being possible for the alkyl or aryl radicals to have attached to them further substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid and the like.
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 and zinc. Particularly preferred metal ions are those of the elements of the Sub-groups of the fourth period. The metal can exist at the various valency levels which they assume.
Furthermore, the compounds I can be converted in a manner known per se to give the N-oxides (cf. U.S. Pat. No. 5,240,940).
Compounds I and their salts or N-oxides which are preferably used for providing the fungicidal mixtures according to the invention are those where the radicals are defined as follows:
R
1
,R
2
,R
3
and 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; and
R
5
,R
6
and 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 a view to the applicability as components in the mixture, particularly preferred compounds are the compounds Ia as shown in Table 1 below.
TABLE 1
No.
R
1
R
2
R
3
R
4
R
5
1
H
H
Cl
H
2-F
2
H
H
Cl
H
2-C(CH
3
)
3
3
H
H
Cl
H
2-CH
3
4
H
H
Cl
H
2-OCH
3
5
H
H
Cl
H
3-F
6
H
H
Cl
H
3-Cl
7
H
H
Cl
H
3-CF
3
8
H
H
Cl
H
3-CN
9
H
H
Cl
H
3-OCH
3
10
H
H
Cl
H
3-phenyl
11
H
H
Cl
H
4-Cl
12
H
H
Cl
H
4-Br
13
H
H
Cl
H
4-CF
3
14
H
H
Cl
H
4-CH
3
15
H
H
Cl
H
4-CH(CH
3
)
2
16
H
H
Cl
H
4-CN
17
H
H
Cl
H
2-Cl—4-F
18
H
H
Cl
H
2,4-di-Br
19
H
H
Cl
H
2,4-di-NO
2
20
H
H
Cl
H
2-CH
3
—4-F
21
H
H
Cl
H
2,6-di-F
22
H
H
Cl
H
2,4,6-tri-CH
3
23
F
H
H
H
4-F
24
Cl
H
H
H
4-F
25
NO
2
H
H
H
4-F
26
H
F
H
H
4-F
27
H
Cl
H
H
4-F
28
H
CH
3
H
H
4-F
29
H
NO
2
H
H
4-F
30
H
OC
2
H
5
H
H
4-F
31
H
H
F
H
4-F
32
H
H
Cl
H
4-F
33
H
H
Br
H
4-F
34
H
H
NO
2
H
4-F
35
H
H
OCF
3
H
4-F
36
H
H
C
2
H
5
H
4-F
37
H
H
SCF
3
H
4-F
38
H
H
O—C
2
H
5
H
4-F
39
H
H
H
F
4-F
40
H
H
H
Cl
4-F
41
H
H
H
CF
3
4-F
42
F
H
F
H
4-F
43
O—CH
3
H
O—CH
3
H
4-F
44
Cl
F
H
H
4-F
45
Cl
Cl
H
H
4-F
Ammermann Eberhard
Bayer Herbert
Eicken Karl
Lorenz Gisela
Sauter Hubert
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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