Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-06-19
2002-06-18
Aulath, Charandit S. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S316000, C504S116100, C504S121000, C504S124000, C504S130000
Reexamination Certificate
active
06407126
ABSTRACT:
The present invention relates to fungicidal mixtures for controlling harmful fungi which comprise, in a synergistically effective amount,
a) 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 group may 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 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
b) a dithiocarbamate (II) selected from the group consisting of
manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa),
manganese ethylenebis(dithiocarbamate) (IIb),
zinc ammoniate ethylenebis(dithiocarbamate) (IIc) and
zinc ethylenebis(dithiocarbamate) (IId)
and/or
c) a carbamate of the formula III
(CH
3
)
2
N—CH
2
CH
2
CH
2
—NH—CO
2
—CH
2
CH
2
CH
3
(III)
and/or
d) an N-acetonylbenzamide of the formula IV
where the substituents have the following meaning:
e) an active ingredient of the formula V,
where the substituents have the following meaning:
R
12
, R
14
independently of one another are halogen or C
1
-C
4
-alkyl;
R
13
is cyano, C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl or C
1
-C
4
-alkoxy;
R
15
is hydrogen or C
1
-C
4
-alkyl;
R
16
is C
2
-C
4
-alkyl;
R
17
is thiocyanato, isothiocyanato or halogen,
or a salt or adduct thereof,
and/or
b) [sic] an active ingredient of the formula V,
where the substituents have the following meaning:
Y is hydrogen, a metal atom of the first to the third main group of the Periodic Table of the Elements or a group NR
19
R
20
R
21
R
22
;
R
18
is hydrogen, a C
1
-C
18
-alkyl group which may be substituted by halogen or a nitro group, a C
2
-C
8
-alkenyl or C
2
-C
8
-alkynyl group which may be substituted by halogen or a nitro group, a C
1
-C
8
-alkoxy-C
1
-C
8
-alkyl or a C
2
-C
8
-alkenyl-C
1
-C
8
-alkyl group, an unsubstituted or substituted aryl group having 6 to 14 carbon atoms, a C
3
-C
7
-cycloalkyl group, a C
1
-C
4
-alkylaryl group or a heterocyclic group having 5 or 6 ring atoms and a hetero atom selected from the group consisting of N, O or S, where the heterocyclic group is attached directly or via an aliphatic chain to the oxygen atom, and
R
19
-R
22
independently of one another are a C
1
-C
4
-alkyl group or a C
1
-C
4
-hydroxyalkyl group,
and/or
f) an active ingredient of the formula VI,
and/or
g) an active ingredient of the formula VII,
where the substituents R
23
to R
26
have the following meanings:
H, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylcarbonyl, formyl, C
3
-C
7
-cycloalkyl, C
6
-C
10
-aryl, unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, nitro- or halogen-substituted, C
1
-C
6
-alkoxy, C
2
-C
6
-alkoxyalkyl, C
2
-C
6
-alkylthioalkyl, di-C
1
-C
4
-alkylaminoalkyl, pyridyl, thiazolyl, furyl or thienyl
and W is O, S or S═O.
The amide compounds of the formula I are known per se and described in the literature (EP-A 545 099).
WO 97/08952 describes fungicidal mixtures which, in addition to compounds of the formula I, contain fenazaquin as further components. These mixtures are described as being very effective against Botrytis.
Also known are the dithiocarbamates II (IIa: common name: mancozeb, U.S. Pat. No. 3,379,610; IIb: common name: maneb, U.S. Pat. No. 2,504,404; IIc: former common name: metiram, U.S. Pat. No. 3,248,400; IId: common name: zineb, U.S. Pat. No. 2,457,674), their preparation and their action against harmful fungi.
Also known is the compound III, its preparation and its use (German Laid-Open Application DOS 15 67 169, common name: propamocarb).
Synergistic mixtures of the compounds IV with dithiocarbamates, their preparation and their action against harmful fungi are known from EP-A 753 258 and U.S. Pat. No. 5,304,572.
The compounds V are described in the literature as fungicides and insecticides (for example DE 24 63 046 and the literature cited therein. A known representative of this class of active ingredients is commercially available under the common name fosetyl or fosetyl-Al.
The compound VI is known under the proposed common name famoxa-done (Proc. Brighton Crop Protection Conference 1996, Pests and Diseases, pages 21-26).
Compounds of the formula VII are known, inter alia, from EP-A 551,048 and EP-A 629,616.
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 (syner-gistic 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 V simultaneously, that is either together or separately, or by applying the compounds I and the compounds II to V in succession than when the compounds I or II to V 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 mildew on grapevines.
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-di-methylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methyl-butyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethyl-propyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethyl-butyl, 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 group 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
Ammermann Eberhard
Eicken Karl
Hampel Manfred
Lorenz Gisela
Schelberger Klaus
Aulath Charandit S.
BASF - Aktiengesellschaft
Keil & Weinkauf
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