Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-09-25
2002-04-30
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...
C548S257000, C548S259000, C548S260000
Reexamination Certificate
active
06380225
ABSTRACT:
The present invention relates to novel benzotriazoles, a process for their preparation and their use as microbicides in crop protection and in protection of materials.
It has already been disclosed that certain benzotriazole derivatives have fungicidal properties (cf. DE-A 1 046 937, EP-A 0 238 824, EP-A 0 462 931, EP-A 0 549 532 and U.S. Pat. No. 2,943,017). The efficacy of the substances described there is good, but at low application rates leaves something to be desired.
Novel benzotriazoles have now been found of the formula
in which
X
1
, X
2
, X
3
and X
4
, independently of each other, represent hydrogen, halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, hatogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, unsubstituted or substituted cycloalkyl, hydroxycarbonyl alkylcarbonyl, alkoxycarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl,
in which
R
1
and R
2
, independently of each other, represent hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted arylcarbonyl, unsubstituted or substituted arylsulphonyl, unsubstituted or substituted arylaminocarbonyl or unsubstituted or substituted arylmethylsulphonyl or
R
1
and R
2
together with the nitrogen atom to which they are bound represent a heterocyclic ring which may optionally be substituted by alkyl and may further contain an oxygen atom or an alkylimino group,
Q represents a direct bond or a carbonyl group,
R
3
represents unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl and
Z represents a direct bond, CH
2
, O, S, SO, SO
2
or CO or
—CO—O—, where the oxygen atom is connected to the aryl or heterocyclyl radical, or
—SO
2
—O—, where the sulphur atom is connected to the aryl or heterocyclyl radical, or
—S-CH
2
—SO
2
—, where the sulphur atom of the thio group is connected to the aryl or heterocyclyl radical, or
X
2
and X
3
together represent an unsubstituted or substituted alkylene chain having 3 or 4 members in which one or two (non-adjacent) carbon atoms can be replaced by oxygen atoms, or
X
2
and X
3
together represent a radical of the formula
R represents unsubstituted or substituted heterocyclyl and
Y represents a direct bond, —CH
2
—, —CH
2
—CH
2
—, —CO—, —SO
2
—, —CO—O— or —SO—O—, where in the case of the two last-named groups, the carbon atom or the sulphur atom is connected to the nitrogen atom of the triazole ring, and their acid addition salts and metal salt complexes.
Furthermore, it has been found that benzotriazoles of the formula (I) and their acid addition salts and metal salt complexes are obtained if benzotriazoles of the formula
in which
X
1
, X
2
, X
3
and X
4
have the meanings given above,
are reacted with halides of the formula
Hal—Y—R (III)
in which
R and Y have the meanings given above and
Hal represents chlorine or bromine,
in the presence or absence of an acid acceptor and in the presence or absence of a diluent and, if appropriate, an acid or a metal salt is added to the compounds of the formula (I) thus obtained.
Finally, it has been found that the benzotriazoles of the formula (I) and their acid addition salts and metal salt complexes possess very good microbicidal properties and can be used both in crop protection and in protection of materials.
Surprisingly, the substances of the invention show markedly better fungicidal activity than the previously known substances of the same indication most similar in terms of constitution.
The substances of the invention are generally defined by the formula (I).
X
1
, X
2
, X
3
and X
4
, independently of each other, preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain 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 may optionally be monosubstituted to penta-substituted, identically or differently, by halogen and/or alkyl having 1 to 4 carbon atoms, 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,
R
1
and R
2
, independently of each other, preferably represent hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, aryl having 6 to 10 carbon atoms, arylcarbonyl having 6 to 10 carbon atoms in the aryl moiety, arylsulphonyl having 6 to 10 carbon atoms, arylaminocarbonyl having 6 to 10 carbon atoms in the aryl moiety or arylmethylsulphonyl having 6 to 10 carbon atoms in the aryl moiety, where each of the aryl radicals mentioned above can be monosubstituted to trisubstituted, identically of differently, by 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
1
and R
2
, furthermore, together with the nitrogen atom to which they are bound preferably represent a heterocyclic ring having 5 or 6 ring members which may optionally be monosubstituted to trisubstituted by alkyl having 1 to 4 carbon atoms and can additionally contain an oxygen atom or a C
1
-C
4
-alkylimino group.
Q also preferably represents a direct bond or a carbonyl group.
R
3
preferably represents aryl having 6 to 10 carbon atoms, where each of these radicals can be monosubstituted to trisubstituted, identically or differently, by 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, or
R
3
preferably represents a saturated or unsaturated heterocyclyl radic
Assmann Lutz
Kugler Martin
Schrage Heinrich
Stenzel Klaus
Tiemann Ralf
Bayer Aktiengesellschaft
Morris Patricia L.
Norris & McLaughlin & Marcus
LandOfFree
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