Acylaminosalicylic acid amides and their uses as pesticides

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...

Reexamination Certificate

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C564S166000, C564S167000

Reexamination Certificate

active

06548549

ABSTRACT:

The invention relates to known and to new acylaminosalicylamides, to a plurality of processes for their preparation and to their use as pesticides. The present application furthermore relates to novel intermediates, to a plurality of processes for their preparation and to their use as pesticides.
Certain acylaminosalicylamides, such as, for example, the compounds 3-formamido-salicylanilide and 3-(formylamino)-2-hydroxy-N-(phenylmethyl)-benzamide, have already been disclosed (compare, for example, B. Biochim. Biophys. Acta (1993), 1143(3), 262-8, J. Med. Chem. (1990), 33(1), 136-42 or J. Biol. Chem. (1971), 246(23), 7125-30).
However, an activity against pests has not been described to date of these prior-art compounds.
It has now been found that the acylaminosalicylamides of the general formula (I)
in which
A represents a single linkage or an alkylene chain,
R
1
represents hydrogen, alkyl or alkoxy,
R
2
represents in each case optionally substituted cyloalkyl, cycloalkenyl, aryl or heterocyclyl
are suitable for controlling pests, preferably fungi, insects and bacteria, in plants and industrial materials.
In the definitions, the hydrocarbon chains such as alkyl, alkene, alkenyl or alkinyl, also in conjunction with hetero atoms such as in alkoxy, alkylthio or alkylamino, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated and also aromatic, cyclic compounds having up to eight ring members in which at least one ring member is a hetero atom, that is to say an atom other than carbon. If the ring contains more than one hetero atom, they can be identical or different. Hetero atoms are preferably oxygen, nitrogen or sulphur. If appropriate, the cyclic compounds together with other carbocyclic or heterocyclic, fused or bridged rings form a polycyclic ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic cyclic compounds which, if appropriate, together with other carbocyclic, fused or bridged rings form a polycyclic ring system.
Cycloalkenyl represents carboxycyclic cyclic compounds which contain at least one double bond and, if appropriate, together With other carbocyclic, fused or bridged rings form a polycyclic ring system
The present application also relates to new acylaminosalicylamides of the general formula (I)
in which
A represents a single linkage or optionally substituted alkylene,
R
1
represents hydrogen, alkyl or alkoxy,
R
2
represents in each case optionally substituted cyloalkyl, cycloalkenyl, aryl or heterocyclyl, with the exception of the nitro group as substituent,
and the compounds 3-(formylamino)-2-hydroxy-N-{4-[2,4,6-tris(1-methylpropyl)-phenoxylphenyl}-benzamide, N-{4-[3,5-bis-(1,1-dimethylethyl)-phenoxy]-phenyl}-3-(formylamino)-2-hydroxy-benzamide, N-{4-[2,4-bis-(1,1-dimethylethyl)-phenoxy]-phenyl}-3-(formylamino)-2-hydroxy-benzamide, N-{4-[2,6-bis-(1-methylpropyl)-phenoxy]-phenyl}-3-(formylamino)-2-hydroxy-benzamide, 3-(formylamino)-2-hydroxy-N-{4-[3-(trifluoromethyl)-phenoxy]-phenyl}-benzamide, N-{4-[4-(1,1-dimethylethyl)-phenoxy]-phenyl}-3-(formylamino)-2-hydroxy-benzamide, 3-(formylamino)-2-hydroxy-N-(4-phenoxyphenyl)-benzamide, N-(4-butylphenyl)-3-(formylamino)-2-hydroxy-benzamide and N-{3-chloro-4-(4-chlorophenoxy)phenyl}-3-(formylamino)-2-hydroxy-benzamide, 3-(formylamino)-2-hydroxy-N-(phenylmethyl)-benzamide, 3-formamido-salicylanilide and 3-(formylamino)-2-hydroxy-N-(2-phenylethyl)-benzamide are excepted.
Furthermore, it has been found that the new acylaminosalicylamides of the general formula (I) are obtained when
a) aminosalicylamides of the general formula (II)
 in which
A and R
2
have the abovementioned meanings
are reacted with acylating agents of the general formula (III)
 in which
R
1
has the abovementioned meaning and
X
1
represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy,
if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a further reaction auxiliary, or when
b) nitrosalicylamides of the general formula (IV)
 in which
A and R
2
have the abovementioned meanings
are reacted with formic acid, if appropriate in the presence of a catalyst and if appropriate in the presence of further reaction auxiliary, or when
c) O-benzyl-nitrosalicylamides of the general formula (V)
 in which
A and R
2
have the abovementioned meanings
are reacted with formic acid, if appropriate in the presence of hydrogen or a non-noble metal, if appropriate in the presence of a catalyst and if appropriate in the presence of a further reaction auxiliary.
If appropriate, the compounds according to the invention exist in the form of mixtures of various isomeric forms which are possible, in particular stereoisomers such as, for example, E and Z, threo and erythro, and optical isomers. We claim the E and Z isomers, the threo and erythro, and the optical isomers and also any mixtures of these.
Preferred is the use of the compounds, or preferred are the new compounds, of the formula (I) in which
A represents a single linkage or an alkylene chain having 1 to 6 carbon atoms,
R
1
represents hydrogen, alkyl or alkoxy, each of which has 1 to 4 carbon atoms,
R
2
represents cycloalkyl or cycloalkenyl, each of which has 3 to 12 carbon atoms and each of which is optionally monosubstituted or polysubstituted by identical or different substituents from the series consisting of halogen, cyano, carboxyl, phenyl (which is optionally substituted by halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-halogenoalkoxy), C
1
-C
4
-alkyl or C
1
-C
4
-alkoxycarbonyl;
or represents aryl having 3 to 12 ring members or heterocyclyl having 3 to 8 ring members, it being possible for each of these aryl or heterocyclyl substituents to be optionally monosubstituted or polysubstituted by identical or different substituents, the possible substituents preferably being selected from the enumeration which follows:
halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl,
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which as 1 to 6 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy, each of which has 2 to 6 carbon atoms;
in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy, each of which has 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched acylamino, N-acyl-N-alkylamino, alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties;
in each case divalent alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms and each of which is optionally monosubstituted or polysubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
cycloalkyl having 3 to 6 carbon atoms;
and aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio, aryloxyalkyl, arylthioalkyl, heterocyclyl, heterocyclyloxy, heterocyclylthio, h

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