Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-05-09
2002-01-01
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S335000, C514S340000, C514S342000, C514S352000, C540S544000, C546S261000, C546S269700, C546S269100, C546S297000
Reexamination Certificate
active
06335325
ABSTRACT:
The present application relates to novel acylated 4-amino-pyridine derivatives, to processes for their preparation and to their use for controlling animal pests and as fungicides.
It is already known that certain substituted 4-amino-pyridines have insecticidal properties (cf., for example, WO 93/04580, WO 96/08475, WO 96/10016, WO 96/14301 or WO 96/33975).
However, in particular at low application rates and concentrations, the activity and/or activity spectrum of these compounds is not always entirely satisfactory.
This invention provides novel acylated 4-amino-pyridines of the formula (I)
in which
R
1
represents alkyl, halogenoalkyl, alkoxy, alkylthio, alkoxyalkyl, alkylthioalkyl or optionally substituted cycloalkyl,
R
2
represents hydrogeni, alkyl, alkoxy, halocen, cyano, aminothiocarbonyl or optionally substituted aryl,
R
3
represents alkyl, alkenyl, optionally substituted cycloalkyl or represents in each case optionally substituted aryl or arylalkyl,
R
4
represents one of the radicals —CO—NR
5
R
6
, —CS—NR
7
R
8
, —C(═NH)—NH—OR
9
, —C(═N—OH)—OH, —CHO, —CH═N—OR
10
and —C(═N—OR
11
)—R
12
or represents an optionally substituted heterocycle
where
R
5
to R
12
independently of one another represent hydrogen or alkyl,
A represents CH, CX
2
or N,
X
1
and X
2
independently of one another represent halogen, alkyl, alkoxy or halogenoalkyl and
m represents 0, 1, 2, 3 or 4,
n represents 0, 1, 2 or 3 and in the case A=CX
2
also represents 4,
including the pyridine N-oxides and salts which are protonated at the pyridine nitrogen.
Furthermore, it has been found that the compounds of the formula (I) are obtained when compounds of the formula (II)
in which
R
1
, R
2
, R
3
, A, X
1
, X
2
, m and n are as defined above
are derivatized at the nitrile group by generally known methods of organic chemistry.
Finally, it has been found that the novel compounds of the formula (I) have strongly pronounced biological properties and are suitable especially as fungicides and for controlling animal pests, in particular insects, arachnids and nematodes, which are encountered in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector.
Surprisingly, the acylated 4-amino-pyridines according to the invention exhibit considerably better activity against animal pests than known compounds of a similar constitution.
The formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned above and below are illustrated below.
R
1
preferably represents C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl having 1 to 5 identical or different halogen atoms, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl or represents C
5
-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
2
-alkyl, C
1
-C
2
-alkoxy, chlorine bromine, cyano aminothiocarbonyl or represents phenyl which is optionally mono- to trisubstituted by identical or different substituents, possible substituents being halogen, (C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkyl having 1 to 5 identical or different halogen atoms.
R
3
preferably represents C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, represents C
5
-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 or represents phenyl or benzyl, each of which is optionally mono- to trisubstituted by identical or different substituents, possible substituents being halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkyl having 1 to 5 identical or different halogen atoms.
R
4
preferably represents one of the radicals —CO—NR
5
R
6
, —CS—NR
7
R
8
, —C(═NH)—NH—OR
9
, —C(═N—OH)—OH, —CHO, —CH═N—OR
10
and —C(═N—OR
11
)—R
12
,
where
R
5
to R
12
independently of one another represent hydrogen or C
1
-C
4
-alkyl;
R
4
also preferably represents a 5- or 6-membered saturated or unsaturated heterocycle which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkyl having 1 to 5 identical or different halogen atoms and contains oxygen and/or sulphur and/or nitrogen as heteroatoms, for example 1,2,4-oxadiazol-3-yl, 1,3-thiazol-2-yl or 1,4,2-dioxazin-3-yl.
A preferably represents CH or N.
A also preferably represents CX
2
.
X
1
and X
2
independently of one another preferably represent fluorine, chlorine, bromine, C
1
-C
2
-alkyl, C
1
-C
2
-alkoxy or C
1
-C
2
-halogenoalkyl having 1 to 5 identical or different halogen atoms.
m and n independently of one another preferably represent 0, 1 or 2.
Halogen (atoms) represents, for example, fluorine (atoms), chlorine (atoms) or bromine (atoms).
R
1
particularly preferably represents methyl, ethyl, methoxy, methylthio, 1-chloro-eth-1-yl, methoxymethyl or methylthiomethyl.
R
2
particularly preferably represents hydrogen, methyl, methoxy, chlorine, bromine, cyano, aminothiocarbonyl or phenyl.
R
3
particularly preferably represents methyl, ethyl, i-propyl, allyl, cyclohexyl, phenyl or benzyl.
R
4
particularly preferably represents one of the radicals —CO—NH
2
, —CO—NHCH
3
, —CO—N(CH
3
)
2
, —CS—NH
2
, —CS—NHCH
3
, —CS—N(CH
3
)
2
, —C(═NH)—NH—OH, —C(═N—OH)—OH, —CHO, —CH═N—OH, —CH═N—OCH
3
, —C(═N—OH)—CH
3
or —C(═N—OCH
3
)—CH
3
;
R
4
also particularly preferably represents 1,2,4-oxadiazol-3-yl, 1,3-thiazol-2-yl or 1,4,2-dioxazin-3-yl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, methoxy and trifluoromethyl.
A particularly preferably represents CH or N.
X
1
and X
2
independently of one another particularly preferably represent fluorine, chlorine, bromine, methyl, methoxy or trifluoromiethyl.
m particularly preferably represents 0.
n particularly preferably represents 0 or 1.
Preferred compounds according to the invention are substances of the formulae (IA), (IB), (IC) and (ID):
in which
R
1
to R
4
, X
1
, X
2
, m and n have the abovementioned general, preferred and particularly preferred meanings.
Preferred compounds according to the invention are also substances of the formulae (IA-1), (IB-1), (IC-1) and (ID-1):
in which
R
1
to R
4
have the abovementioned general preferred and particularly preferred meanings.
The abovementioned general or preferred radical definitions or illustrations apply to the end products and, correspondingly, to the starting materials and intermediates. These radical definitions can be combined with one another at will, i.e. including combinations between the respective preferred ranges.
Preference, according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferable).
Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
In the radical definitions given above and below, hydrocarbon radicals, such as alkyl or alkenyl are in each case straight-chain or branched as far as this is possible—including in combination with heteroatoms such as alkoxy or alkylthio.
The following compounds of the formula (IC-1) may be mentioned in particular:
TABLE a
(IC-1)
R
1
R
2
R
3
R
4
C
2
H
5
Cl
i—C
3
H
7
—CO—NH
2
C
2
H
5
Cl
i—C
3
H
7
—CO—NHCH
3
C
2
H
5
Cl
i—C
3
H
7
—CO—N(CH
3
)
2
C
2
H
5
Cl
i—C
3
H
7
—CS—NH
2
C
2
H
5
Cl
i—C
3
H
7
—CS—NHCH
3
C
2
H
5
Cl
i—C
3
H
7
—CS—N(CH
3
)
2
C
2
H
5
Cl
i—C
3
H
7
—C(═NH)—NH—OH
C
2
H
5
Cl
i—C
3
H
7
—C(═N—OH)—OH
C
2
H
5
Cl
i—C
3
H
7
—CHO
C
2
H
5
Cl
i—C
3
H
7
—CH═N—OH
C
2
H
5
Cl
i—C
3
H
7
—CH═N—OCH
3
C
2
H
5
Cl
i—C
3
H
Alig Bernd
Bretschneider Thomas
Erdelen Christoph
Heil Markus
Kleefeld Gerd
McKenzie Thomas
Shah Mukund J.
Zurcher Jackie Ann
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