Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-04-27
2002-06-11
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S372000, C548S128000, C548S214000
Reexamination Certificate
active
06403622
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel phenylacetic acid heterocyclyl amides, to a process for their preparation and to their use for controlling undesirable microorganisms and animal pests.
BACKGROUND OF THE INVENTION
It is already known that numerous N-(5-isothiazolyl)-amides or N-(5-thiadiazolyl)-amides have insecticidal and fungicidal properties (cf. WO 97-18 198, WO 97-26 251 and WO 95-31 448). The activity of these substances is good; however, it is sometimes unsatisfactory at low application rates.
SUMMARY OF THE INVENTION
Phenylacetic acid heterocyclyl amides of the formula
may be used to control microorganisms and animal pest.
DETAILED DESCRIPTION
This invention, accordingly, provides novel phenylacetic acid heterocyclyl amides of the formula
in which
R
1
represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or represents optionally substituted cycloalkyl,
R
2
represents hydrogen, alkylcarbonyl, alkoxycarbonyl or represents in each case optionally substituted arylcarbonyl, aryloxycarbonyl or aralkyloxycarbonyl,
R
3
represents hydrogen or alkyl,
R
4
represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkinyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkyloxy or represents optionally substituted aralkyloxyalkyl, or two geminal or vicinal R
4
radicals together with the carbon atom(s) to which they are attached form a saturated or unsaturated, optionally substituted five-or six-membered ring which may contain one or two hetero atoms,
n represents integers from 1 to 4,
x represents a nitrogen atom or represents a grouping of the formula CH, C—Cl, C—Br, C—C≡CH, C—CN or
and
A represents a direct bond or a CH
2
group.
Furthermore, it has been found that phenylacetic acid heterocyclyl amides of the formula (I) can be prepared by
a) reacting amino derivatives of the formula
in which
R
1
, R
3
and X are as defined above,
with diols of the formula
in which
A, R
4
and n are as defined above,
if appropriate in the presence of a diluent and in the presence of a dehydrating agent
and
b) if appropriate, reacting the resulting phenylacetic acid heterocyclyl amides of the formula
in which
R
1
, R
3
, R
4
, A, X and n are as defined above,
with acid halides of the formula
in which
Hal represents chlorine or bromine and
R
5
represents alkyl, alkoxy or represents in each case optionally substituted aryl, aryloxy or aralkyloxy,
in the presence of a diluent and in the presence of an acid binder.
Finally, it has been found that the phenylacetic acid heterocyclyl amides of the formula (I) are highly suitable for controlling undesirable microorganisms and animal pests.
Surprisingly, the compounds according to the invention have significantly better fungicidal and insecticidal activity than the constitutionally most similar priort-art compounds of the same direction of action.
The formula (I) provides a general definition of the phenylacetic acid heterocyclyl amides according to the invention.
R
1
preferably represents C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, represents C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio or represents C
3
-C
6
-cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of C
1
-C
4
-alkyl and halogen.
R
2
preferably represents hydrogen, C
1
-C
4
-alkyl-carbonyl, C
1
-C
4
-alkoxy-carbonyl or represents phenyl-carbonyl, phenyloxy-carbonyl or phenyl-C
1
-C
4
-alkyloxy-carbonyl, where the three last mentioned radicals may be mono- to trisubstituted in the phenyl moiety by identical or different substituents from the group consisting of halogen, nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms and/or halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms.
R
3
preferably represents hydrogen or C
1
-C
4
-alkyl.
R
4
preferably represents C
1
-C
12
-alkyl, C
1
-C
8
-halogenoalkyl having 1 to 8 identical or different halogen atoms, C
1
-C
4
-hydroxyalkyl, C
2
-C
8
-halogenoalkenyl having 1 to 8 identical or different halogen atoms, C
2
-C
8
alkinyl, C
2
-C
8
-halogenoalkinyl having 1 to 8 halogen atoms, C
1
-C
8
-alkoxy-C
1
-C
4
-alkyl, C
2
-C
8
-alkenoxy-C
1
-C
4
-alkyl, C
2
-C
8
-alkinoxy-C
1
-C
4
-alkyl, C
1
-C
8
-halogenoalkoxy-C
1
-C
4
-alkyl having 1 to 8 identical or different halogen atoms, C
2
-C
8
-halogenoalkenyloxy-C
1
-C
4
-alkyl having 1 to 8 identical or different halogen atoms, C
2
-C
8
-halogenoalkinyloxy-C
1
-C
4
-alkyl having 1 to 8 identical or different halogen atoms, C
1
-C
8
-alkoxycarbonyl-C
1
-C
4
-alkyl, C
4
-C
8
-alkylcarbonyloxy-C
1
-C
4
-alkyl, C
1
-C
8
-halogenoalkyl-carbonyloxy-C
1
-C
4
-alkyl having 1 to 8 identical or different halogen atoms, C
1
-C
8
-alkylthio-C
1
-C
4
-alkyl, or represents phenyl, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, phenylalkoxy having 1 to 4 carbon atoms in the alkoxy moiety or represents phenylalkyloxyalkyl having 1 to 4 carbon atoms in the alkyl moiety and 1 to 4 carbon atoms in the oxyalkyl moiety, where the four last mentioned radicals may be mono- to trisubstituted in the phenyl moiety by identical or different substituents from the group consisting of halogen, nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, alkylsulfinyl having 1 to 4 carbon atoms, alkylsulfonyl having 1 to 4 carbon atoms, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety and alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety.
Moreover, two geminal or vicinal R
4
radicals together with the carbon atom(s) to which they are attached preferably represent a saturated or unsaturated five- or six-membered ring which may contain one or two oxygen, sulfur and/or nitrogen atoms and which may be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms and/or alkoxy having 1 to 4 carbon atoms.
n preferably represents 1, 2 or 3.
X preferably represents a nitrogen atom or represents a grouping of the formula CH, CCl, CBr, C—CN, C—C≡CH or
A also preferably represents a direct bond or represents a CH
2
group.
R
1
particularly preferably represents methyl, ethyl, propyl, isopropyl, n-butyl, i-butyl, sec-butyl, tert-butyl, halogenoalkyl having 1 or 2 carbon atoms and 1 to 3 fluorine, chlorine, and/or bromine atoms, alkoxyalkyl having 1 or 2 carbon atoms in the alkoxy moiety and 1 or 2 carbon atoms in the alkyl moiety, alkylthioalkyl having 1 or 2 carbon atoms in the alkylthio moiety and 1 or 2 carbon atoms in the alkyl moiety, methoxy, ethoxy, methylthio, ethylthio or represents cyclopentyl, cyclohexyl or cyclopropyl, optionally mono- or disubstituted by methyl, ethyl, fluorine and/or chlorine.
R
2
particularly preferably represents hydrogen, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, i-butoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, phenylcarbonyl, phenyloxycarbonyl or phenylalkoxycarbonyl having 1 or 2 carbon atoms in the alkoxy moiety, where the three last mentioned radicals may be mono- or disubstituted in the phenyl moiety by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, chloromethyl, dichloromethyl, difluoromethyl, trifluoromethyl, trifluoromethoxy and trifluoromethylthio.
R
3
particularly preferably represents hydrogen, methyl or
Alig Bernd
Bretschneider Thomas
Heil Markus
Mauler-Machnik Astrid
Militzer Hans-Christian
Bayer Aktiengesellschaft
Gerstl Robert
Gil Joseph C.
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