Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-10-21
2001-07-17
Pak, John (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S519000, C514S520000, C514S521000, C514S523000, C514S525000, C514S613000, C514S617000, C514S618000, C514S623000, C514S624000, C514S354000, C504S100000, C422S028000, C422S037000
Reexamination Certificate
active
06262091
ABSTRACT:
TECHNICAL FIELD
The present invention relates to compositions for controlling harmful fungi and methods for controlling harmful fungi using compositions of this type.
BACKGROUND ART
It is known that p-hydroxyaniline derivatives of the formula I
are employed as active compounds in fungicidal compositions. Thus compounds of the formula I are disclosed in EP-A 0 339 481, EP-A 0 653 418 and the German Patent Applications 195 04 599.8 and 95 40 970.1.
EP-A-545 099 describes anilide compounds of the formula
where A is phenyl which is substituted in the 2-position by ethyl, trifluoromethyl, chlorine, bromine or iodine or is certain aromatic or nonaromatic heterocyclic radicals, which can be unsubstituted or substituted by methyl, chlorine or trifluoromethyl, and R is certain aliphatic or cycloaliphatic radicals, which can be unsubstituted or substituted by halogen, or is phenyl which is unsubstituted or substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio or halogen. These compounds can be used for controlling Botrytis.
EP-A-589 301 describes anilide compounds of the same formula, where A is a cyclic radical of the formula:
where R
1
is hydrogen or C
1
-C
4
-alkyl; R
2
is halogen or C
1
-C
4
-alkyl; R
3
is C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl; n is 1 or 2; and R essentially has the meanings indicated above. These compounds can also be used for treating Botrytis.
WO 93/11117 describes compounds of the formula
where
Q is C
1
-C
3
-alkyl, C
2
-C
3
-alkenyl, C
2
-C
3
-alkynyl, —(CH
2
)
m
CH═ or —(CH
2
)
m
—X—(CH
2
)
m
—;
n is 0 or 1;
each m independently of one another is 0, 1, 2 or 3;
each X independently is O or S;
R
1
is certain alicyclic radicals;
R
2
is hydrogen, fluorinated methyl, methyl, ethyl, C
2
-C
6
-alkenyl, C
3
-C
6
-chloroalkyl, phenyl, alkylthioalkyl, alkoxyalkyl, haloalkylthioalkyl, haloalkoxyalkyl or hydroxyalkyl;
R
3
is halomethyl, halomethoxy, methyl, ethyl, halogen, cyano, methylthio, nitro, aminocarbonyl or aminocarbonylmethyl;
R
4
is hydrogen, halogen or methyl;
R
5
, R
6
and R
7
are each independently of one another selected from hydrogen, halogen, cyano, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
3
-C
4
-cycloalkyl and halomethoxy. These compounds are fungicidally active, but on their own do not have a sufficiently broad and satisfactory spectrum of action.
When these active compounds are used alone, however, it has been shown that their action is only temporary, i.e. after some time renewed growth of the fungi could be observed.
DISCLOSURE OF INVENTION
It is an object of the present invention to improve the action of the mentioned compounds in controlling harmful fungi.
We have found that this object is achieved if compounds of the type indicated are used in combination.
The invention therefore relates to compositions for controlling harmful fungi, which, in a solid or liquid carrier, contain:
a) at least one p-hydroxyaniline derivative of the formula I
where
R
1
is hydrogen, alkyl, which can be partially or completely halogenated and/or can carry one or two of the following groups: alkoxy, haloalkoxy, alkylthio, cycloalkyl, cycloalkenyl, it being possible for the cyclic groups for their part to carry one, two or three halogen atoms, alkyl groups and/or alkoxy groups, and aryl which can be partially or completely halogenated and/or can carry one, two or three of the following substituents: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
cycloalkyl or cycloalkenyl, it being possible for these radicals to be partially or completely halogenated and/or to carry 1, 2, 3, 4 or 5 of the following groups: alkyl, haloalkyl, alkoxy, haloalkoxy and aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following substituents: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
C
6
-C
15
-bicycloalkyl or C
7
-C
15
-bicycloalkenyl, it being possible for these radicals to be partially or completely halogenated and/or to carry 1, 2, 3, 4 or 5 of the following groups: alkyl, haloalkyl, alkoxy, haloalkoxy and aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following substituents: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
R
2
and R
3
independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;
z is H or R
4
—(CO)—, where
R
4
is the following radicals: alkyl or alkenyl, it being possible for these groups to be partially or completely halogenated and/or to carry one of the following radicals: alkoxy, haloalkoxy, alkylthio, cycloalkyl, cycloalkenyl or aryl, it being possible for the aromatic radicals for their part to carry one, two or three of the following groups: nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
cycloalkyl or cycloalkenyl, it being possible for these groups to carry one, two or three of the following radicals: halogen, alkyl, haloalkyl and alkoxy;
aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following radicals: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
OR
5
or NR
6
R
7
, where
R
5
is alkyl or alkenyl, it being possible for these groups to be partially or completely halogenated and/or to carry one of the following radicals: alkoxy, haloalkoxy, alkylthio, cycloalkyl, cycloalkenyl or aryl, it being possible for the aromatic radicals for their part to carry one, two or three of the following groups: nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
or is cycloalkyl or cycloalkenyl, it being possible for these groups to carry one, two or three of the following radicals: halogen, alkyl, haloalkyl and alkoxy;
or is aryl which can be partially or completely halogenated and/or can carry one, two or three of the following radicals; nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
R
6
is alkyl or alkenyl, it being possible for these groups to be partially or completely halogenated and/or to carry one of the following radicals: alkylthio, cycloalkyl, cycloalkenyl or aryl, it being possible for the aromatic radicals for their part to carry one, two or three of the following groups: nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
cycloalkyl or cycloalkenyl, it being possible for these groups to carry one, two or three of the following radicals: halogen, alkyl, haloalkyl and alkoxy;
aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following radicals: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; and
R
7
is hydrogen or alkyl, and
b) at least one amide compound of the formula II
A—CO—NR
8
—R
9
(II)
where
A is an aryl group or an aromatic or nonaromatic, 5- or 6-membered heterocycle which has 1 to 3 heteroatoms which are selected from O, N and S; it being possible for the aryl group or the heterocycle, if appropriate, to have 1, 2 or 3 substituents which are selected independently of one another from alkyl, halogen, CHF
2
, CF
3
, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl;
R
8
is a hydrogen atom, alkyl or alkoxy;
R
9
is a phenyl or cycloalkyl group which, if appropriate, has 1, 2 or 3 substituents which independently of one another are selected from phenyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy and cycloalkenyloxy, and which can additionally be substituted by 1 or more halogen atoms, it being possible for the aliphatic and cycloaliphatic radicals to be partially or completely halogenated and/or the cycloaliphatic radicals to be substituted by 1, 2 or 3 alkyl groups and for the phenyl group for its part to have 1 to 5 halogen atoms and/or 1 to 3 substituents which independently of one another are selected from alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and haloalkylthio, and the amide phenyl group, if appropriate, being fused to a saturated 5-membere
Ammermann Eberhard
Eicken Karl
Kohle Harald
Lorenz Gisela
Retzlaff Gunter
BASF - Aktiengesellschaft
Keil & Weinkauf
Pak John
LandOfFree
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