Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-01-20
2001-11-20
O'Sullivan, Peter (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S256000, C514S341000, C544S319000, C546S275400, C548S374100
Reexamination Certificate
active
06319940
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel carbanilides, to a plurality of processes for their preparation and to their use for controlling plant and animal pests.
BACKGROUND OF THE INVENTION
It is already known that numerous carboxamides have fungicidal properties (cf. WO 93-11 117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313). The activity of these compounds is good, but in some cases leaves something to be desired.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel carbanilides of the formula
in which
R represents halogen, nitro, cyano, alkyl having 1 to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety,
m represents numbers 0, 1, 2, 3 or 4,
A represents a radical of the formula
R
1
represents halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R
2
represents hydrogen, halogen, cyano or alkyl having 1 to 4 carbon atoms, or
A represents a radical of the formula
R
3
and R
4
independently of one another each represent hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R
5
represents halogen, cyano, alkyl having 1 to 4 carbon atoms or halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula
R
6
and R
7
independently of one another each represent hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R
8
represents hydrogen, alkyl having 1 to 4 carbon atoms or represents halogen, or
A represents a radical of the formula
R
9
represents halogen, cyano, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms or represents halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula
R
10
represents halogen, cyano, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms or represents halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R
11
represents hydrogen, halogen, cyano, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms or represents halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula
R
12
represents alkyl having 1 to 4 carbon atoms or represents halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,
X
1
represents a sulphur atom, represents SO, SO
2
or —CH
2
, or
A represents a radical of the formula
R
13
represents alkyl having 1 to 4 carbon atoms or represents halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula
R
14
represents halogen, cyano, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula
R
15
and R
16
independently of one another each represent hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R
17
represents hydrogen, halogen or alkyl having 1 to 4 carbon atoms, or
A represents a radical of the formula
R
18
represents hydrogen, halogen, amino, cyano or alkyl having 1 to 4 carbon atoms and
R
19
represents halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula
R
20
represents hydrogen, halogen, amino, cyano or alkyl having 1 to 4 carbon atoms and
R
21
represents halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbons and 1 to 5 halogen atoms, or
A represents a radical of the formula
R
22
represents hydrogen or alkyl having 1 to 4 carbon atoms and
R
23
represents halogen or alkyl having 1 to 4 carbon atoms, or
A represents a radical of the formula
Q represents alkylene having 1 to 4 carbon atoms, alkenylene having 2 to 4 carbon atoms, alkinylene having 2 to 4 carbon atoms or a group of the formula
in which
R
24
, R
25
and R
26
independently of one another each represent hydrogen, alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkenyl having 2 to 4 carbon atoms or alkinyl having 2 to 4 carbon atoms, or
Q represents a group of the formula
R
27
and R
28
independently of one another each represent hydrogen or alkyl having 1 to 4 carbon atoms,
Y represents an oxygen atom or represents S(O)
r
, where
r represents the numbers 0, 1 or 2, and
n and p independently of one another each represent the numbers 0, 1 or 2,
where the molecular moiety labelled (*) is in each case attached to the phenyl radical of the aniline moiety,
X represents oxygen or sulphur and
Z represents optionally substituted phenyl, optionally substituted naphthyl, optionally substituted anthracenyl or represents optionally substituted hetaryl.
Furthermore, it has been found that carbanilides of the formula (I) are obtained when
a) acyl halides of the formula
in which
A and X are each as defined above and
Hal represents halogen
are reacted with aniline derivatives of the formula
in which
Q, R, Z and m are each as defined above,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
b) carbanilide derivatives of the formula
in which
A, R, X and m are each as defined above and
X
2
represents oxygen or sulphur,
are reacted with compounds of the formula
in which
R
28
, Z and p are each as defined above and
E represents a leaving group,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
c) carbanilide derivatives of the formula
in which
A, R, R
27
, X and m are each as defined above and
E
1
represents a leaving group
are reacted with compounds of the formula
in which
R
28
, Z and p are each as defined above and
X
3
represents oxygen or sulphur,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
d) carbanilide derivatives of the formula
in which
A, R, R
27
, X and m are each as defined above
are reacted with compounds of the formula
in which
R
28
, Z and p are each as defined above and
E represents a leaving group,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent or,
e) carbanilide derivatives of the formula
in which
A, R, R
26
, X and m are each as defined above
are reacted with hydroxylamine derivatives of the formula
H
2
N—O—Z (X)
in which
Z is as defined above,
if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent.
Finally, it has been found that the novel carbanilides of the formula (I) are very suitable for use as pesticides. They have microbicidal properties and can be employed for controlling undesirable microorganisms both in crop protection and in the protection of materials. Additionally, they are suitable for controlling animal pests.
Surprisingly, the carbanilides of the formula (I) according to the invention have considerably better fungicidal activity than the constitutionally most similar prior-art carboxamides of the same direction of action.
The formula
Buschhaus Hans-Ulrich
Dutzmann Stefan
Elbe Hans-Ludwig
Erdelen Christoph
Kruger Bernd-Wieland
Bayer Aktiengesellschaft
Gil Joseph C.
O'Sullivan Peter
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