Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-01-29
2002-05-14
Morris, Patricia L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S117000
Reexamination Certificate
active
06387922
ABSTRACT:
The present invention relates to novel fused azole derivatives, to a plurality of processes for their preparation and to their use as microbicides in crop protection and in the protection of materials.
It is already known that certain fused azole derivatives have fungicidal properties (cf. DE-A 195 23 446). Thus, for example, 1-(3,5-dimethyl-isoxazol-4-sulphonyl)-1H-benzotriazole can be employed for controlling fungi. The activity of this substance is good but in some cases unsatisfactory at low application rates.
This invention, accordingly, provides novel fused azole derivatives of the formula
in which
R
1
and R
2
together with the carbon atoms to which they are attached represent an optionally substituted heterocyclic ring or represent an optionally substituted benzo-fused heterocyclic ring,
G represents nitrogen or a grouping
in which
R3 represents hydrogen, halogen, cyano, nitro, trifluoromethyl, thiocarbamoyl, thiocyanato or the grouping
in which
R
4
represents alkyl,
A represents one of the following groupings
in which
Y represents oxygen or sulphur,
R5 represents an optionally substituted, unsaturated heterocyclic radical,
R6 and R7 independently of one another represent alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkenyl, halogenoalkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy, alkinylthio, optionally alkyl-, cycloalkyl- or aryl-substituted amino, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted cycloalkylthio or represents an optionally substituted, saturated or unsaturated heterocyclic radical, or
R6 and R7 together with the phosphorus atom to which they are attached represent an optionally substituted heterocyclic radical,
and also their acid addition salts and metal salt complexes.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
Furthermore, it has been found that the fused azole derivatives of the formula (I) and also their acid addition salts and metal salt complexes are obtained when
a) azoles of the formula
in which
R
1
, R
2
and G are as defined above
are reacted with halides of the formula
A—X
1
(III)
in which
A is as defined above and
X
1
represents halogen,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,
or when
b) cyanoimidazoles of the formula
in which
R
1
, R
2
and A are as defined above
are reacted with hydrogen sulphide, if appropriate in the presence of a base and if appropriate in the presence of a diluent, or when
c) thiocarbamoylimidazoles of the formula
in which
R
1
, R
2
and A are as defined above
are reacted with an alkylating agent of the formula
R
4
—X
2
(IV)
in which
R
4
is as defined above and
X
2
represents a leaving group,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,
and an acid or a metal salt is added, if appropriate, to the resulting compounds of the formula (I).
Finally, it has been found that the fused azole derivatives of the formula (I) and also 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 have better fungicidal activity than 1-(3,5-dimethyl-isoxazole-4-sulphonyl)-1H-benzotriazole, which is an active compound of the prior art having similar constitution and the same direction of action.
The formula (I) provides a general definition of the substances according to the invention.
R
1
and R
2
together with the carbon atoms to which they are attached preferably represent a 5- or 6-membered heterocyclic ring which contains one, two or three identical or different heteroatoms, such as oxygen, sulphur and/or nitrogen, and may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxyl, amino, formyl, carboxyl, carbamoyl, thiocarbamoyl, 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 4 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms, in each alkyl group, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, hydroximinoalkyl having 1 to 4 carbon atoms in the alkyl moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety and halogenoalkylcarbonyloxy having 1 to 4 carbon atoms in the halogenoalkyl group and 1 to 5 identical or different halogen atoms,
or
R
1
and R
2
together with the carbon atoms to which they are attached preferably represent a benzo-fused 5- or 6-membered heterocyclylic ring which contains one or two identical or different heteroatoms, such as oxygen, sulphur and/or nitrogen, and may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxyl, amino, formyl, carboxyl, carbamoyl, thiocarbamoyl, 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 4 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl group, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, hydroximinoalkyl having 1 to 4 carbon atoms in the alkyl moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety and halogenoalkylcarbonyloxy having 1 to 4 carbon atoms in the halogenoalkyl group and 1 to 5 identical or different halogen atoms,
where, if the heterocyclic ring or the benzo-fused heterocyclic ring contains more than one oxygen atom, the oxygen atoms are not adjacent.
G also preferably represents nitrogen or a grouping
R
3
preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, trifluoromethyl, thiocarbamoyl, thiocyanato or the grouping
R
4
preferably represents alkyl having 1 to 4 carbon atoms.
A also preferably represents one of the following groupings: —SO
2
—R
5
,
Y also preferably represents oxygen or sulphur.
R
5
preferably represents an unsaturated heterocyclyl radical having 5 or 6 ring members and 1 to 3 identical or different heteroatoms, such as nitrogen, oxygen and/or sulphur, where each of the heterocyclyl radicals may be mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxyl, amino, formyl, carboxyl, carbamoyl, thiocarbamoyl, 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
Assmann Lutz
Elbe Hans-Ludwig
Stenzel Klaus
Tiemann Ralf
Bayer Aktiengesellschaft
Gil Joseph C.
Morris Patricia L.
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