Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2002-05-23
2004-09-07
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S164000, C514S620000
Reexamination Certificate
active
06787670
ABSTRACT:
The invention relates to novel glyoxylic acid amides, to a plurality of processes for their preparation and to their use for controlling harmful organisms.
It is already known that certain glyoxylic acid amides with a constitution similar to that of the compounds described below have fungicidal properties (compare, for example WO 96/23763, WO 98/17630 or WO 98/58903). However, in many cases, the fungicidal action of these compounds is unsatisfactory.
This invention provides novel compounds of the general formula (I),
in which
R
1
represents aryl which optionally has a fused-on cycloalkyl ring, where both the aryl molecule and the cycloalkyl molecule optionally carry further substituents and
a) R
2
represents alkoxyalkyl or optionally methyl- or halogen-substituted arylalkyl, and
R
3
represents optionally substituted alkyl, alkenyl or alkinyl,
or
b) R
2
represents optionally substituted alkyl, alkoxyalkyl or arylalkyl, and
R
3
represents optionally substituted alkenyl or alkinyl,
or
c) R
2
represents methyl or ethyl, and
R
3
represents optionally substituted alkyl having at least 3 carbon atoms,
or
d) R
2
represents alkyl having at least 2 carbon atoms, and
R
3
represents optionally substituted methyl or ethyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
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.
Cycloalkyl represents saturated carbocyclic cyclic compounds which optionally form a polycyclic ring system with further carbocyclic fused-on or bridged rings.
Cycloalkenyl represents carbocyclic cyclic compounds which contain at least one double bond and optionally form a polycyclic ring system with further carbocyclic fused-on or bridged rings.
Furthermore, it has been found that the novel glyoxylic acid amides of the general formula (I) have very good action against harmful organisms, in particular a strong fungicidal action.
If appropriate, the compounds according to the invention are present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as for example, E and Z, cis or trans, threo or erythro, and also optical isomers. What is claimed and described are both the E and the Z isomers, and also the threo and erythro and the optical isomers, and any mixtures of these isomers.
The invention preferably provides compounds of the formula (I) in which
R
1
represents aryl which optionally has a fused-on cycloalkyl ring having 3 to 10 ring members, where the cycloalkyl molecule is optionally substituted by 1 to 4 alkyl chains having in each case 1-4 carbon atoms and the aryl molecule is optionally additionally substituted by the substituents listed below:
Halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoy);
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched halogenalkyl, halogenalkoxy, halogenalkylthio, halogenalkylsulfinyl or halogenalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched halogenylalkenyl or halogenalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl molecules;
cycloalkyl having 3 to 6 carbon atoms, and
a) R
2
represents alkoxyalkyl having a total of 2 to 10 carbon atoms or optionally methyl- or halogen-substituted arylalkyl having 1 to 4 carbon atoms in the alkyl molecule and
R
3
represents optionally cyano-, alkoxy- or alkoxycarbonyl-substituted alkyl having 1 to 8 carbon atoms, alkenyl or alkinyl having from 2 to 8 carbon atoms,
or
b) R
2
represents alkyl having 1 to 8 carbon atoms or optionally methyl- or halogen-substituted arylalkyl having 1 to 4 carbon atoms in the alkyl molecule and
R
3
represents optionally cyano-, alkoxy- or alkoxycarbonyl-substituted alkenyl or alkinyl having 2 to 8 carbon atoms,
or
c) R
2
represents methyl or ethyl, and
R
3
represents optionally cyano-, alkoxy- or alkoxycarbonyl-substituted alkyl having at least 3 carbon atoms,
or
d) R
2
represents alkyl having at least 2 carbon atoms, and
R
3
represents optionally cyano-, alkoxy- or alkoxycarbonyl-substituted methyl or ethyl.
The invention relates in particular to compounds of the formula (I) in which
R
1
represents phenyl which is in each case optionally mono- to trisubstituted and which optionally has fused-on cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cylcooctyl or cyclononyl ring, where the cycloalkyl molecule is optionally mono- to tetrasubstituted by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl and the phenyl molecule is optionally additionally substituted by the substituents listed below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
a) R
2
represents methoxyethyl, ethoxyethyl or optionally methyl-, fluorine- or chlorine-substituted benzyl or phenethyl and
R
3
represents optionally cyano-, methoxy-, ethoxy-, methoxycarbonyl- or ethoxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl, heptyl, octyl, allyl, methylallyl, crotonyl, propinyl, butinyl or benzyl,
or
b) R
2
represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl, heptyl or octyl or optionally methyl-, fluorine- or chlorine-substituted benzyl or phenethyl, and
R
3
represents optionally cyano-, methoxy-, ethoxy-, methoxycarbonyl- or ethoxycarbonyl-substituted allyl, methylallyl, crotonyl, propinyl or butinyl,
or
c) R
2
represents methyl or ethyl, and
R
3
represents optionally cyano-, methoxy-, ethoxy-, methylcarbonyl or ethoxycarbonyl-substituted n- or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl, heptyl or octyl,
or
d) R
2
represents n- or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl, heptyl or octyl, and
R
3
represents optionally cyano-, methoxy-, ethoxy-, methoxycarbonyl- or ethoxycarbonyl-substituted methyl or ethyl.
R
1
particularly preferably represents para-chlorophenyl, para-bromophenyl, 1,2,3,4-tetrahydronaphthalene or indane.
R
2
particularly preferably represents ethyl, in particular methyl.
R
3
particularly preferably represents cyanomethyl, allyl or propargyl.
The general or preferred radical definitions given above apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation.
The radical definitions given in the respective combinat
Boie Christiane
Fischer Reiner
Heinemann Ulrich
Kuck Karl-Heinz
Seitz Thomas
Bayer Aktiengesellschaft
Harmuth Raymond J.
Henderson Richard E.L.
Kumar Shailendra
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