Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-09-24
2002-12-03
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...
C514S247000, C514S256000, C514S269000, C514S345000, C514S348000, C514S351000, C514S365000, C514S369000, C514S372000, C514S406000, C514S407000, C514S424000, C514S425000, C514S427000, C514S428000, C514S438000, C514S445000, C514S446000, C514S466000, C514S473000, C514S617000, C514S622000
Reexamination Certificate
active
06489348
ABSTRACT:
The present invention relates to fungicidal mixtures for controlling harmful fungi, which mixtures comprise amide compounds of the formula I
A—CO—NR
1
R
2
(I)
in which
A is an aryl group or an aromatic or non-aromatic, 5- or 6-membered heterocycle which has from 1 to 3 hetero atoms selected from O, N and S;
where the aryl group or the heterocycle may or may not have 1, 2 or 3 substituents which are selected, independently of one another, from alkyl, halogen, CHF
2
, CF
3
, alkoxy, haloalkoxy, alkylthio, alkylsulfynyl and alkylsulfonyl;
R
1
is a hydrogen atom;
R
2
is a phenyl or cycloalkyl group which may or may not have 1, 2 or 3 substituents which are selected from alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkenyloxy, phenyl and halogen, where the aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or the cycloaliphatic radicals may be substituted by from 1 to 3 alkyl groups and where the phenyl groupmay have from 1 to 5 halogen atoms and/or from 1 to 3 substituents which are selected, independently of one another, from alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and haloalkylthio, and where the amidic phenyl group may or may not be condensed with a saturated 5-membered ring which may or may not be substituted by one or more alkyl groups and/or may have a hetero atom selected from O and S,
and
compounds of the formula II, their N-oxide or one of their salts
where the substituents are as defined below:
R
12
, R
13
, R
14
, R
15
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
16
, R
17
, R
18
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 containing an aryl group may for their part carry from 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/or compounds of the formula III
where the substituents X
1
to X
5
and R
19
to R
22
are as defined below:
X
1
to X
5
independently of one another are 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
19
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 halogen, cyano and C
1
-C
4
-alkoxy;
R
20
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 N, O and S, where the cyclic radicals may have from 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
-alkynyl;
R
21
and R
22
independently of one another are 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.
The amide compounds of the formula I are known per se and are described in the literature (EP-A 545 099).
WO 97/08952 describes fungicidal mixtures which, in addition to compounds of the formula I, also comprise fenazaquin as further components. These are described as being very effective against Botrytis.
The compounds of the formula II are known per se and are described, for example, in U.S. Pat. No. 5,240,940. Fungicidal mixtures which comprise the compounds of the formula II in addition to other fungicidally active compounds are also already known and are described in O.Z. 45483.
The compounds of the formula III and processes for their preparation are described in WO-A 96/19442.
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 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 the compounds II to III simultaneously, that is either together or separately, or by applying the compounds I and the compounds II to III in succession than when the compounds I or II to III are applied on their own.
The mixtures according to the invention have synergistic action and are therefore particularly suitable for controlling harmful fungi and in particular powdery mildew fungi in vegetables, grapevines and cereals.
In the context of the present invention, halogen is fluorine, chlorine, bromine and iodine and is in particular fluorine, chlorine and bromine.
The term “alkyl” includes straight-chain and branched alkyl groups. These are preferably straight-chain or branched C
1
-C
12
-alkyl and in particular C
1
-C
6
-alkyl groups. Examples of alkyl groups are alkyl such as, in particular, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, decyl, dodecyl.
Haloalkyl is an alkyl group as defined above which is partially or fully halogenated by one or more halogen atoms, in particular by fluorine and chlorine. Preferably, there are from 1 to 3 halogen atoms present, and the difluoromethyl or the trifluoromethyl group is particularly preferred.
The above statements for the alkyl group and the haloalkyl group apply in a corresponding manner to the alkyl and haloalkyl groups in alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfynyl and alkylsulfonyl.
The alkenyl group includes straight-chain and branched alkenyl groups. These are preferably straight-chain or branched C
3
-C
12
-alkenyl groups and in particular C
3
-C
6
-alkenyl groups. Examples of alkenyl groups are 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,1-dimethyl-3-butenyl [sic], 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl, in particular 2-propenyl, 2-butenyl, 3-methyl-2-butenyl and 3-methyl-2-pentenyl.
The alkenyl group may be partially or fully halogenated by one or more halogen atoms, in particular by fluorine or chlorine. The alkenyl group preferably has f
Ammermann Eberhard
Eicken Karl
Hampel Manfred
Lorenz Gisela
Schelberger Klaus
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
LandOfFree
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