Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-08-03
2001-07-31
Morris, Patricia L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S304400, C548S310100
Reexamination Certificate
active
06268508
ABSTRACT:
The present invention relates to new halogenobenzimidazoles, to a process for their preparation, and to their use as microbicides in crop protection and in the protection of materials. The invention furthermore relates to new intermediates and to a process for their preparation.
It has already been disclosed that certain benzimidazole derivatives have fungicidal properties (cf. DE-A 4 139 950 and EP-A 0 517 476). 2-Cyano-3ediethylaminosulphonyl-6,6,7,7-tetafluoro-[1,4]dioxino[2,3-f]benzimidazole and 2-cyano6,6difluoro-2-methylaminosulphonyl-[1,3]dioxolo[4,5-f]benzimidazole, for example, can be employed for controlling fungi. The efficacy of these substances is good, but leaves something to be desired in some cases when low rates of application are used.
There have now been found new halogenobenzimidazoles of the formula
in which
R
1
, R
2
, R
3
and R
4
independently of one another represent hydrogen, halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, optionally substituted cycloalkyl, hydroxycarbonyl alkylcarbonyl alkoxycarbonyl cycloalkylcarbonyl, cycloalkoxycarbonyl or
R
5
represents optionally substituted aryl or optionally substituted heterocyclyl,
Z represents a direct bond, or represents —CH
2
, O, S, SO, SO
2
,or CO,
or represents —CO—O—, the oxygen atom being bonded to R
5
,
or represents —SO
2
—O—, the oxygen atom being bonded to R
5
,
or represents —S—CH
2
—SO
2
—, the sulphur atom of the thio group being bonded to R
5
R
6
and R
7
independently of one another represent hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted arylsulphonyl, optionally substituted arylaminocarbonyl or optionally substituted arylmethylsulphonyl, or
R
6
and R
7
together with the nitrogen atom to which they are bonded represent an optionally alkyl-substituted heterocyclic ring which can additionally contain an oxygen atom or an alkylimino group and
Q represents a direct bond or a carbonyl group, or
R
1
and R
2
, or R
2
and R
3
, or R
3
and R
4
, in each case together, represent an optionally substituted alkylene chain having 3 or 4 members in which one or two (non-adjacent) carbon atoms can be replaced by oxygen atoms,
A represents one of the following groups —SO
2
—R
8
, —CO—R
9
or
Y represents oxygen or sulphur and
R
8
, R
9
, R
10
and R
11
independently of one another represent alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkenyl, halogenoalkyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy, alkinylthio, amino, alkylamino, dialkylamino, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted cycloalaylthio, optionally substituted cycloalkylamino, optionally substituted dicycloalkamino or an optionally substituted saturated or unsaturated heterocyclic radical, or
R
10
and R
11
together with the phosphorus atom to which they are bonded represent an optionally substituted heterocyclic radical, and
X represents halogen,
and their acid addition salts and metal salt complexes.
Furthermore, it has been found that halogenobenzimidazoles of the formula (I) and their acid addition salts and meal salt complexes are obtained when
a) benzimidazole derivatives of the formula
in which
R
1
, R
2
, R
3
, R
4
and X have the abovementioned meanings,
are reacted with halides of the formula
A—X
1
(III)
in which
A has the abovementioned meaning and
X
1
represents halogen,
if appropriate in the presence of an acid-binding agent and if appropriate in the presence of a diluent,
and, if appropriate, the resulting compounds of the formula (I) are subjected to an addition reaction with an acid or a metal salt.
Finally, it has been found that the halogenobenzimidazoles of the formula (I) and their acid addition salts and metal salt complexes have very good microbicidal properties and can be employed both in crop protection and in the protection of materials.
Surprisingly, the substances according to the invention display a better fungicidal activity than 2-cyano-3-dimethylaminosulphonyl-6,6,7,7-tetrafluoro-[1,4]-dioxino[2,3-f]benzimidazole and 2-cyano6,6-difluoro2-dinetylaminosulphonyl-[1,3]dioxolo[4,5-f]benzimidazole, which are prior-art active compounds of similar constitution and the same direction of action.
Formula (I) provides a general definition of the substances according to the invention.
R
1
, R
2
, R
3
and R
4
independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched alkyl having 1 to 8 carbon atoms, straighten or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkoxy having 1 to 8 carbon atoms, straight-chain or branched halogenoalkoxy having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylthio having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylthio having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphinyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphinyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphonyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms which is optionally monosubstituted to pentasubstituted by identical or different substituents from the series consisting of halogen and/or alkyl having 1 to 4 carbon atoms, or represent hydroxycarbonyl, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, alkoxycarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkoxy moiety, cycloalkylcarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, cycloalkoxycarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, or represent —Z—R
5
or
R
5
preferably represents aryl having 6 to 10 carbon atoms, it being possible for each of these radicals to be monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylsulphinyl having 1 to 4 carbon atoms, alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and/or halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms.
R
5
preferably also represents an unsaturated heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and/or sulphur, it being possible for these radicals to be monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl having 1 to 3 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, cyano and/or nitro.
Z preferably also represents a direct bond, and —CH
2
, S, SO, SO
2
or CO,
or represents —CO—O—, the oxygen atom being bonded
Assmann Lutz
Marhold Albrecht
Bayer Aktiengesellschaft
Morris Patricia L.
Norris & McLaughlin & Marcus
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