DE4309969A1 - Substituted hetero-fused imidazoles - Google Patents

Description

The invention relates to new substituted, hetero-fused imidazoles, a process for their manufacture and their use as herbicides.

It is known that certain benzimidazoles have insecticidal properties, however, the use of hetero-fused imidazoles as herbicides is still over nothing became known.

There have now been new substituted, hetero-fused imidazoles of the general formula (I),

in which
R ^{1 represents} hydrogen or a straight-chain or branched, optionally unsubstituted or substituted radical of the series alkyl, alkoxy or aryl,
R ^{2 is} hydroxyl, cyano or a straight-chain or branched, optionally unsubstituted or substituted radical from the alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, di alkoxyphosphonyl group, ( Hetero) aryl, (hetero) arylcarbonyl, (hetero) aryl oxycarbonyl, (hetero) arylcarbonyloxy or (hetero) arylaminocarbonyl aminocarbonyloxy,
R ^{3 represents} cyano, halogen or a straight-chain or branched radical which is in each case optionally unsubstituted or substituted in the series alkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkynyloxy, amino, aminocarbonyl or aryl,
A ¹ , A ² , A ³ and A ⁴ each represent optionally N (nitrogen), N-CHR ¹ R ² or CX, with at least one but at most two nitrogen atoms occurring simultaneously in the hetero-fused ring and all positional isomers being possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ^{2 are} in the presence of two nitrogen atoms, and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted (R ³ ),
wherein
X ¹ , X ² and X ³ each independently of one another for hydrogen, halogen, cyano, nitro or for a straight-chain or branched, optionally unsubstituted or substituted radical of the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, for hydroxycarbonyl, alkylcarbonyl, , are alkoxycarbonyl, cycloalkyloxycarbonyl for each case optionally substituted amino or aminocarbonyl, or represents in each ge optionally substituted aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or aryl thiomethylsulfonyl, but where at least one of the substituents X ^1, X ² or X ³ for haloalkyl haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyl, for optionally substituted, fused-in dioxyalkylene, for hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, for each optionally substituted amino or A minocarbonyl or represents in each case optionally substituted aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl,
found.

The compounds of formula (I) may optionally, depending on the Type and number of substituents as geometric and / or optical isomers or Regioisomers or their isomer mixtures in different compositions, but also as positional isomers, for example in the following variations:

or, for example, the following variations can also be considered:

It was also found that the new substituted, hetero-fused Imidazoles of the general formula (I),

in which
R¹ is hydrogen or a straight-chain or branched, optionally unsubstituted or substituted radical from the series alkyl, alkoxy or aryl,
R² is hydroxyl, cyano or a straight-chain or branched, optionally unsubstituted or substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero ) Aryl, (hetero) arylcarbonyl, (hetero) aryl oxycarbonyl, (hetero) arylcarbonyloxy or (hetero) arylaminocarbonyl aminocarbonyloxy,
R ^{3 represents} cyano, halogen or a straight-chain or branched radical which is in each case optionally unsubstituted or substituted in the series alkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkynyloxy, amino, aminocarbonyl or aryl,
A ¹ , A ² , A ³ and A ⁴ each represent optionally N (nitrogen), N-CHR ¹ R ² or CX, with at least one but at most two nitrogen atoms occurring simultaneously in the hetero-fused ring and all positional isomers being possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ^{2 are} in the case of two nitrogen atoms and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted (R ³ ),
wherein
X ¹ , X ² and X ³ each independently of one another for hydrogen, halogen, cyano, nitro or for a straight-chain or branched, optionally unsubstituted or substituted radical of the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, for hydroxycarbonyl, Alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, for in each case optionally substituted amino or aminocarbonyl, or for in each case optionally substituted aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl but where substituents are, but where ¹ , X ² or X ³ for haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyl, for optionally substituted, fused di oxyalkylene, for hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, for each optionally substituted amino or he stands for aminocarbonyl or for optionally substituted aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl,
get when one

• a) substituted 1H-hetero-fused imidazoles of the formula (II), in which
  A¹, A ² , A ³ , A ⁴ and R ^{3 have} the meanings given above, with compounds of the formula (III), in which
  M stands for a suitable leaving group,
  R ¹ and R ^{2 have} the meanings given above,

optionally in the presence of a diluent and optionally in Ge in the presence of a reaction aid.

Finally it was found that the new substituted, hetero-fused Imidazoles of the general formula (I) have good activity as herbicides.

Surprisingly, the new substituted hetero according to the invention show fused imidazoles of the general formula (I) have a considerable herbicidal activity against problem weeds and at the same time a comparably good one Compatibility with important crops.  

The substituted, hetero-fused imidazoles according to the invention are generally defined by the formula (I). Compounds of formula (I) are preferred in which
R ^{1 represents} hydrogen or a straight-chain or branched, optionally unsubstituted or substituted radical of the series alkyl, alkoxy each having 1 to 8 carbon atoms or optionally mono- or polysubstituted, identically or differently substituted, phenyl, the following being suitable as substituents:
Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, halogenoalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts, optionally one or more times, identical or different, by halogen and / or straight-chain or branched Alkyl having 1 to 6 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, substituted, double-linked di oxyalkylene having 1 to 5 carbon atoms or optionally single or multiple, identical or phenyl differently substituted by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
R ² for hydroxyl, cyano or for a straight-chain or branched and each optionally mono- or polysubstituted, identically or differently substituted radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl with each is up to 8 carbon atoms in the individual alkyl or alkenyl or alkynyl parts, the following being suitable as substituents:
Fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 8 carbon atoms or in each case optionally mono- or polysubstituted, identically or differently substituted aryl having 6 to 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 5 heteroatoms - in particular nitrogen, Oxygen and / or sulfur - is available, the aryl or heteroaryl substituents mentioned in R ^{1 being} suitable,
R ² also stands for amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents being in each case:
Formyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 8 carbon atoms, in each case, if appropriate, singly or twice, identically or differently, by straight-chain or branched alkyl having 1 to 8 carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 8 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or carbonthio-1-carbonate the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl each having 2 to 6 carbon atoms in the alkanediyl part, in each case optionally in the aryl part once or several times, identically or verse chie the substituted arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl each having 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the aryl part mono- or polysubstituted, identically or differently, aryl, arylcarbonyl or aryloxycarbonyl each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ² also stands for aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which is optionally mono- or polysubstituted, identical or different, each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ² also for heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each of which is mono- or polysubstituted in the same or different ways, each having 2 to 9 carbon atoms and 1 to 5 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - in the hetero atom where the aro substituents mentioned in R ¹ are suitable as heteroaryl substituents,
R ³ for cyano, fluorine, chlorine, bromine, iodine or for a straight-chain or branched, each optionally unsubstituted or substituted radical from the series cycloalkyl, alkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkenyloxy each with up to 8 carbon atoms in the individual alkyl, alkenyl or alkynyl parts, the possible substituents in each case being: fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 8 carbon atoms or, in each case, optionally mono- or polysubstituted, identically or differently substituted, aryl with 6 up to 10 carbon atoms or heteroaryl with 2 to 9 carbon atoms and 1 to 5 heteroatoms - in particular nitrogen, oxygen and / or sulfur -, the aryl or heteroaryl substituents mentioned in R ^{1 being} suitable,
R ³ also represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents being in each case:
Formyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 8 carbon atoms, in each case, if appropriate, singly or twice, identically or differently, by straight-chain or branched alkyl having 1 to 8 carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 8 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or carbonthio-1-carbonate the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl each having 2 to 6 carbon atoms in the alkanediyl part, in each case optionally in the aryl part once or several times, identically or verse chie the substituted arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl each having 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the aryl part mono- or polysubstituted, identically or differently, aryl, arylcarbonyl or aryloxycarbonyl each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ³ also stands for aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, each having 6 to 10 carbon atoms in the aryl, the aryl substituents in each case being those mentioned in R ¹ ,
A ¹ , A ² , A ³ and A ⁴ each optionally represent N (nitrogen), N-CHR ¹ R ² or CX, where at least one but at most two nitrogen atoms occur simultaneously in the hetero-fused ring and all positional isomers are possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ² are present with two nitrogen atoms and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted (R ³ ) and
X ¹ , X ² , X ³ each independently for hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, for each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms, for cycloalkyl with 3 to 8 carbon atoms, for each straight-chain or branched haloalkyl, haloalkoxy, haloalkyl thio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms or for optionally single or multiple, identical or different, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, substituted, double-linked dioxyalkylene having 1 to 5 carbon atoms, also for hydroxycarbonyl, for each straight-chain or branched alkyl carb onyl or alkoxycarbonyl each with 1 to 6 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3 to 8 carbon atoms in the cycloalkyl part or for in each case monosubstituted or polysubstituted, identical or differently substituted amino or aminocarbonyl, the amino substituents in each case being:
each straight-chain or branched alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or alkylcarbonyl each having 1 to 6 carbon atoms in the individual alkyl parts or in the aryl part, in each case optionally singly or multiply, identically or differently substituted arylcarbonyl , Arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned at R ¹ ;
X ¹ , X ² , X ³ also for aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo, each with 6 to 10 carbon atoms in the aryl part, each being mono- or polysubstituted in the aryl part, one or more times stand, the aryl substituents in each case those mentioned in R ¹ and
where at least one of the substituents X ¹ , X ² or X ³ for in each case rad-chain or branched haloalkyl haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, for straight-chain or branched alkylsulfonyl 1 to 6 carbon atoms or for optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched halo genalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms , doubly linked dioxyalkylene with 1 to 5 carbon atoms, also for hydroxycarbonyl, for straight-chain or branched alkylcarbonyl or alkoxycarbonyl each with 1 to 6 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3 to 8 carbon atoms in the cycloalkyl part or f stands for amino or aminocarbonyl which is mono- or polysubstituted in the same way or differently, where appropriate as amino substituents in each case:
each straight-chain or branched alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or alkylcarbonyl each having 1 to 6 carbon atoms in the individual alkyl parts or in the aryl part, in each case optionally singly or multiply, identically or differently substituted arylcarbonyl , Arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned at R ¹ ;
X ¹ , X ² , X ³ also represent aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo, each with 6 to 10 carbon atoms in the aryl part, each of which is mono- or polysubstituted in the aryl part, one or more times, identically or differently, the aryl substituents in each case those mentioned in R ¹ come into question.

Compounds of the formula (I) in which
R ^{1 stands} for hydrogen, or for an optionally unsubstituted or substituted, straight-chain or branched radical of the series alkyl, alkoxy each having 1 to 6 carbon atoms or for optionally monosubstituted to trisubstituted, identically or differently substituted, phenyl, the substituents being in question come:
Fluorine, chlorine, bromine, iodine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, halogenoalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoal alkyl each having 1 to 4 carbon atoms in the individual alkyl parts, optionally up to six times, identically or differently by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, doubly linked dioxyalkylene having 1 to 4 carbon atoms or, if appropriate, single to five times , phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, where halogen is in each case fluorine, chlorine, Bromine, iodine stands,
R ² for hydroxy, cyano or for a straight-chain or branched radical which is optionally monosubstituted to pentas, identically or differently, substituted by fluorine, chlorine, bromine or iodine, and is a radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl , Alkylcarbonyloxy or dialkoxyphosphonyl each having up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl parts or for each optionally optionally mono- to trisubstituted, identically or differently substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each with up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, the following being suitable as substituents:
straight-chain or branched alkoxy having 1 to 6 carbon atoms or, in each case, optionally mono- to trisubstituted, identically or differently substituted aryl having 6 or 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 4 heteroatoms - in particular nitrogen, oxygen and / or sulfur , the aryl or heteroaryl substituents mentioned in R ^{1 being} suitable,
R ² also stands for amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents being in each case:
Formyl, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 6 carbon atoms, in each case, if appropriate, singly or twice, identically or differently, by straight-chain or branched alkyl having 1 to 6 carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 7 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-1-carbonate in each case the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each having 2 to 5 carbon atoms in the alkanediyl part, in each case in the aryl part, in each case simply to triple, identically or differently hieden substituted arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl each with 6 or 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the aryl part mono- to trisubstituted, identically or differently substituted, aryl, arylcarbonyl or aryloxycarbonyl, each with 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ² also represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which has from 6 to 10 carbon atoms in the aryl part and is optionally monosubstituted to fivefold, identical or different, the aryl substituents in each case being those mentioned in R ¹ ,
R ² also for each mono- to pentasubstituted, identically or differently substituted heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy each having 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - in the heteroatoms where the aro substituents mentioned in R ¹ are suitable as heteroaryl substituents,
R ³ for cyano, fluorine, chlorine, bromine, iodine or for a straight-chain or branched, optionally single to five times, the same or different substituted by fluorine, chlorine, bromine and / or iodine radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy , Alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl or alkylcarbonyloxy, each having up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl parts or for cycloalkyl, alkyl, alkenyl, alkynyl, alkynyl, alkoxy, alkenyloxy optionally monosubstituted to trisubstituted or substituted Alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each having up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, the following being suitable as substituents:
Fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 6 carbon atoms or in each case optionally single to triple, identically or differently substituted aryl having 6 or 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 4 heteroatoms - in particular nitrogen, Oxygen and / or sulfur - is available, the aryl or heteroaryl substituents mentioned in R ^{1 being} suitable,
R ³ also represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents being in each case:
Formyl, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 6 carbon atoms, in each case, if appropriate, singly or twice, identically or differently, by straight-chain or branched alkyl having 1 to 6 carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 7 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-1-carbonate in each case the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each having 2 to 5 carbon atoms in the alkanediyl part, in each case in the aryl part, in each case simply to triple, identically or differently hieden substituted arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl each with 6 or 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the aryl part mono- to trisubstituted, identically or differently substituted, aryl, arylcarbonyl or aryloxycarbonyl, each with 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ³ also represents aryl, each of which is monosubstituted to pentas, the same or different, each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
A ¹ , A ² , A ³ and A ⁴ each optionally represent N (nitrogen), N-CHR ¹ R ² or CX, where at least one but at most two nitrogen atoms occur simultaneously in the hetero-fused ring and all positional isomers are possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ² are present with two nitrogen atoms and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted (R ³ ) and
X ¹ , X ² , X ³ each independently of one another for hydrogen, fluorine, chlorine, bromine, cyano, nitro, for each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, for cycloalkyl having 3 up to 7 carbon atoms, each for straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or for optionally one to six times, identical or different, by halogen and / or straight chain termed or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, doubly linked dioxyalkylene having 1 to 4 carbon atoms, moreover for hydroxycarbonyl, for each straight-chain or branched alkylcarbonyl or he alkoxycarbonyl each having 1 to 4 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl having 3 to 7 carbon atoms in the cycloalkyl part or for in each case monosubstituted or disubstituted, identically or differently substituted amino or aminocarbonyl, the amino substituents in each case being:
each straight-chain or branched alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alk oxyalkyl or alkylcarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts or in the aryl part, in each case, if appropriate, simply to five times, the same or different substituted arylcarbonyl, arylsulfonyl, alylamino carbonyl or arylmethylsulfonyl each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ;
X ¹ , X ² , X ³ also represent aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo, each with 6 or 10 carbon atoms in the aryl part, in each case optionally monosubstituted to fivefold, identically or differently, in the aryl part , the aryl substituents in each case those mentioned in R ¹ and
where at least one of the substituents X ¹ , X ² , X ³ for each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, halo alkylsulfinyl, haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, for straight-chain or branched alkylsulfonyl 1 to 4 carbon atoms or for optionally single to six-fold, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or ge rad-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, doubly linked dioxyalkylene with 1 to 4 carbon atoms, also for hydroxycarbonyl, for straight-chain or branched alkylcarbonyl or alkoxycarbonyl each with 1 to 4 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3 to 7 carbon atoms in the cycloalkyl part or for r each is optionally mono- or disubstituted, identical or differently substituted amino or aminocarbonyl, the following being suitable as amino substituents:
each straight-chain or branched alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alk oxyalkyl or alkylcarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts or in the aryl part, in each case, if appropriate, simply to five times, the same or different substituted arylcarbonyl, arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ;
X ¹ , X ² , X ³ also for aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo each having 6 or 10 carbon atoms in the aryl part, such as phenyl, in each case optionally monosubstituted to fivefold, identically or differently, in the aryl part or naphthyl, the aryl substituents in each case being those mentioned in R ¹ .

Compounds of the formula (I) in which
R ^{1 stands} for hydrogen or for an optionally unsubstituted or substituted straight-chain or branched radical of the series alkyl, alkoxy each having 1 to 4 carbon atoms or for optionally mono- or disubstituted, identically or differently substituted phenyl, the following being suitable as substituents:
Fluorine, chlorine, bromine, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 3 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 3 Carbon atoms and 1 to 7 identical or different halogen atoms, each straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl each having 1 to 3 carbon atoms in the individual alkyl parts, optionally up to four times, identically or differently by halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, substituted, double-linked dioxyalkylene having 1 to 3 carbon atoms or, if appropriate, single to triple, the same ch or different phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, where halogen is in each case fluorine, chlorine, bromine stands,
R ² for hydroxy, cyano or for a straight-chain or branched radical which is optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine and / or bromine and is substituted in the alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl group , Alkylcarbonyloxy or dialkoxyphosphonyl each having up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, or for each optionally mono- or disubstituted, identically or differently substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, Alkoxycarbonyl, alkylcarbonyloxy or dialkoxy phosphoryl, each having up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl parts, where the following are suitable as substituents:
straight-chain or branched alkoxy having 1 to 3 carbon atoms or optionally mono- or disubstituted, identically or differently substituted phenyl, the phenyl substituents mentioned in R ^{1 being} suitable,
R ² also stands for amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents being in each case:
Formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 4 carbon atoms, in each case, if appropriate, singly or twice, identically or differently, by straight-chain or branched alkyl having 1 to 4 carbon atoms 4 carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthiocarbonyl, alkoxythiocarbonyl or alkylthio-1-carbonate the individual straight-chain or branched alkyl parts, in each case doubly linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each having 2 to 4 carbon atoms in the alkanediyl part, in each case optionally in the phenyl part single or double, identical or ve r differently substituted phenylalkyl, phenylalkylcarbonyl or phenylalkyloxy carbonyl each having 1 to 4 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the phenyl part monosubstituted or disubstituted, identically or differently substituted phenyl, phenylcarbonyl or phenyloxycarbonyl, the phenyl substituents in each case being those mentioned in R ¹ come,
R ² also represents phenyl, phenylcarbonyl, phenyloxycarbonyl, phenylcarbonyloxy or phenylaminocarbonylaminocarbonyloxy, each of which is monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents mentioned in R ^{1 being} suitable,
R ² also for heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each of which is optionally monosubstituted to trisubstituted, identically or differently, with in each case 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - in the heteroatoms where the heteroaryl substituents in each case are the phenyl substituents mentioned for R ¹ ,
R ^{3 represents} cyano, fluorine, chlorine, bromine or a straight-chain or branched radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, which is optionally monosubstituted to trisubstituted by fluorine, chlorine and / or bromine, Alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy each having up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, or for each optionally mono- or disubstituted, identically or differently substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl , Alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphoryl each having up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, the following being suitable as substituents:
straight-chain or branched alkoxy having 1 to 3 carbon atoms or optionally mono- or disubstituted, identically or differently substituted phenyl, the phenyl substituents mentioned in R ^{1 being} suitable,
R ³ also represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents being in each case:
Formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 4 carbon atoms, in each case, if appropriate, singly or twice, identically or differently, by straight-chain or branched alkyl having 1 to 4 carbon atoms 4 carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthiocarbonyl, alkoxythiocarbonyl or alkylthio-1-carbonate the individual straight-chain or branched alkyl parts, in each case doubly linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each having 2 to 4 carbon atoms in the alkanediyl part, in each case optionally in the phenyl part single or double, identical or ve r differently substituted phenylalkyl, phenylalkylcarbonyl or phenylalkyloxy arbonyl each having 1 to 4 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the phenyl part monosubstituted or disubstituted, identically or differently substituted phenyl, phenylcarbonyl or phenyloxycarbonyl, the phenyl substituents in each case being those mentioned in R ¹ come,
R ³ also represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents in each case being those mentioned in R ¹ ,
A ¹ , A ² , A ³ and A ⁴ each optionally represent N (nitrogen), N-CHR ¹ R ² or CX, where at least one but at most two nitrogen atoms occur simultaneously in the hetero-fused ring and all positional isomers are possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ² are present with two nitrogen atoms and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted (R ³ ), and
X ¹ , X ² , X ³ independently of one another each for hydrogen, chlorine, bromine, cyano, nitro, for each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, for cycloalkyl having 3, 5 or 6 carbon atoms, each for straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkyl sulfinyl, haloalkylsulfonyl each having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms or for optionally up to four times, identical or different, by halogen and / or straight-chain or branched Alkyl with 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms substituted, doubly linked dioxyalkylene with 1 to 3 carbon atoms, furthermore for hydroxycarbonyl, for each straight-chain or branched alkylcarbonyl or alkox ycarbonyl, each with 1 to 3 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3, 5 or 6 carbon atoms in the cycloalkyl part, or for in each case monosubstituted or disubstituted, identically or differently substituted amino or aminocarbonyl, the following being suitable as amino substituents:
each straight-chain or branched alkyl having 1 to 3 carbon atoms, haloalkyl having 1 to 3 carbon atoms and 1 to 7 halogen atoms, alk oxyalkyl or alkylcarbonyl each having 1 to 3 carbon atoms in the individual alkyl parts or in the phenyl part, in each case, if appropriate, simply to triple, identical or different substituted phenylcarbonyl, phenylsulfonyl, phenylaminocarbonyl or phenylmethylsulfonyl, the phenyl substituents in each case being those mentioned in R ¹ ;
X ¹ , X ² , X ³ also represent phenyl, phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulfonyl or phenylazo, each of which is monosubstituted to trisubstituted in the phenyl moiety in the same or different ways, phenyloxycarbonyl, phenylthiomethylsulfonyl or phenylazo, the phenyl substituents in each case being the phenyl substituents ¹ mentioned and
where at least one of the substituents X ¹ , X ² , X ³ each represents straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, for straight-chain or branched alkylsulfonyl having 1 up to 3 carbon atoms or for optionally up to four times, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms ized, double-linked dioxyalkylene with 1 to 3 carbon atoms, also for hydroxycarbonyl, for straight-chain or branched alkylcarbonyl or alkoxycarbonyl each with 1 to 3 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3, 5 or 6 carbon atoms in the cycloalkyl part or represents in each case monosubstituted or disubstituted, identically or differently substituted amino or aminocarbonyl, the following being suitable as amino substituents:
each straight-chain or branched alkyl having 1 to 3 carbon atoms, haloalkyl having 1 to 3 carbon atoms and 1 to 7 halogen atoms, alk oxyalkyl or alkylcarbonyl each having 1 to 3 carbon atoms in the individual alkyl parts or in the phenyl part, in each case, if appropriate, simply to triple, identical or different substituted phenylcarbonyl, phenylsulfonyl, phenylaminocarbonyl or phenylmethylsulfonyl, the phenyl substituents in each case being those mentioned in R ¹ ;
X ¹ , X ² , X ³ also for phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulfonyl or phenylazo, each of which is monosubstituted to trisubstituted by identical or different substituents in the phenyl moiety, in each case those mentioned in R ¹ as phenyl substituents Question to be considered.

In particular, apart from the connections mentioned in the production examples gene the following substituted hetero-fused imidazoles of the general formula (I) called:

Table I

The entire examples also apply to R ³ = CHF ₂ , R ³ = C ₂ F ₅ , R ³ = C ₃ F ₇ and also for each X ¹ to X ³ 1468 00070 552 001000280000000200012000285912135700040 0002004309969 00004 21349 <pattern the R ² and R ³ variation as indicated in the table can be carried out.

The substituent variations given in the table above can also for the other isomeric pyridines:

This variation applies analogously, restricted to X ¹ and X ² , also to the pyrimidinoimidazoles

the pyridazines

and the pyrazine

For example, pyrimidinoimidazole (1) and Chloromethyl ethyl ester as starting compounds, so the course of the reaction can represent the process of the invention by the following reaction scheme:

Formula (II) provides a general definition of the heteroanellated imidazoles required as starting materials for carrying out the process according to the invention. In this formula (II) A ¹ , A ² , A ³ , A ⁴ and R ³ preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention.

The 1H-hetero-fused imidazoles of the formula (II) are known or are available in Analogy to known processes (GB 1 114 199; JP 62 294 683; J. Heterocyl. Chem. 18 (2), 303-7; EP 297 661; J. Med. Chem. 33 (8), 2231-9).

Formula (III) provides a general definition of the compounds which are furthermore required as starting materials for carrying out the process according to the invention. In this formula (III), R ¹ and R ² preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.

M stands for a leaving radical customary in alkylating agents, preferably for halogen, arylsulfonic acid esters, aralkylsulfonic acid esters, alkylsulfonic acid esters, alkyl carbonyloxy or arylcarbonyloxy, particularly preferably for chlorine, bromine, iodine, C _1-8 - alkylsulfonic acid esters, tolylsulfonic acid esters, phenylsulfonic acid esters, C _1-8 alkyl carbonyloxy, or benzoyl and particularly preferably for chlorine, bromine, C ₁ -C ₂ alkyl sulfonic acid esters, phenyl sulfonic acid esters, tolyl sulfonic acid esters, C ₁ -C ₃ alkyl carbonyloxy or benzoyl.

The compounds of formula (III) are known or can be obtained in analogy to be known processes (see, for example, DE 20 40 175; DE 21 19 518; Synthesis 1973, 703).

Coming as a diluent for carrying out the process according to the invention inert organic solvents. These include in particular aliphati cal, alicyclic or aromatic, optionally halogenated hydrocarbons, such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, Pe trol ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride material; Ethers, such as diethyl ether, diisopopyl ether, dioxane, tetrahydrofuran or Ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or Me ethyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides like N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyr rolidone or hexamethylphosphoric triamide; Esters, such as methyl acetate or Ethyl acetate or bases such as pyridine or organic acids such as ants acid or acetic acid.

The process according to the invention is preferably carried out in the presence of a suitable one Reaction auxiliary carried out. All the usual inorganic ones come as such or organic bases in question. These include, for example, alkaline earth or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, lithium diethylamide, Sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hy hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonia umacetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hy bicarbonate or aminonium carbonate, lithium-organic compounds, such as n- Butyllithium and tertiary amines, such as trimethylamine, triethylamine, tributylamine, Diisopropylethylamine, tetramethylguanidine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diaza bicyclonones (DBN) or diazabicycloundecene (DBU).

In cases where A in formula (III) represents an alcohol, alkanoyloxy or alkoxy group pe, organic or inorganic acids also come as reaction aids, such as sulfuric acid, hydrochloric acid, p-toluenesulfonic acid, perfluorobutane sul fonic or strongly acidic ion exchanger in question.  

If appropriate, the process according to the invention can also be carried out in a two-phase system, such as, for example, water / toluene or water / dichloromethane, if appropriate in the presence of a suitable phase transfer catalyst. Examples of such catalysts are: tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl-methylphosphonium bromide, trimethyl-C ₁₃ / C ₁₅ -alkylammonium chloride, trimethyl-C ₁₃ / C ₁₅ -alxylammonium bromide, dibenzyl-dimethyl-dibenzyl-dimethyl-dibenzyl-methyl-dibenzyl-dimethyl-dibenzyl-dimethyl-dibenzyl-dimethyl-dibenzyl-dimethyl-dibenzyl-dimethyl-dibenzyl-dimethyl-dibenzyl-dimethyl ₁₂ / C ₁₄ -alkyl benzylammonium chloride, dimethyl-C ₁₂ / C ₁₄ -alkyl-benzylammonium bromide, tetrabutylammonium hydroxide, triethylbenzylammonium chloride, methyltrioctylammonium chloride, trimethylbenzylammonium chloride, 15-crown-5, 18-crown-6 or tris- [2- (2- methoxyethoxy) ethyl] amine.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between -70 ° C and + 200 ° C, preferably at temperatures between between 0 ° C and 130 ° C.

The process according to the invention is usually carried out under normal pressure leads. However, it is also possible to work under increased or reduced pressure ten.

To carry out the process according to the invention, 1H- hetero-fused imidazole of formula (II) generally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol of compound of formula (III) and optionally 0.01 to 5.0 mol, preferably 1.0 to 3.0 mol, of reaction auxiliaries.

In a special embodiment, it is also possible to use the 1H hetero-fused Imidazoles of the formula (II) first in a preceding reaction step usual silylation process, for example with hexamethyldisilazane or trimethyl silyl chloride, optionally in the presence of a suitable catalyst, such as as sulfuric acid, trifluoroacetic acid, ammonium sulfate, imidazole or saccharin to silylate at temperatures between -20 ° C and + 50 ° C and the so available hetero-fused 1-trimethyisilylimidazoles in a subsequent second stage To move alkylating agents of formula (II) according to the inventive method  put. In this case, it is advantageous as a catalyst for the alkylation reaction Add tin tetrachloride (see, for example, Chem. Heterocycl. Comp. USSR 24, 514 [1988]).

He carried out the reaction, working up and isolating the reaction products follows according to known methods (see also the manufacturing examples).

The end products of the formula (I) are purified using customary processes, for example by column chromatography or by recrystallization.

The characterization takes place with the help of the melting point or with non-crystallizing compounds - especially with regioisomer mixtures - with the help of proton nuclear magnetic resonance spectroscopy ( ¹ H-NMR).

The active compounds according to the invention can be used as defoliants, desiccants, herb kills Means and especially used as a weed killer. Under Weeds in the broadest sense are all plants that grow in places, where they are undesirable. Whether the substances according to the invention as total or selective Herbicides act essentially depends on the amount applied.

The active compounds according to the invention can, for. B. used in the following plants become:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthi um, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Son chus, Solanuni, Rorippa, RotaIa, Lindernia, Immium, Veronica, Abutilon, Emex, Da tura, viola, galeopsis, papaver, centaure.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pi sum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera: Ecliinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorg  hum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means limited to these Genres limited, but extends in the same way to other plants Zen.

The compounds are suitable for totaling depending on the concentration herb control z. B. on industrial and track systems and on paths and squares and without tree cover. Likewise, weed control compounds in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, nut, banana, Coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants and for selective weed control can be used in annual crops.

The active compounds according to the invention can be particularly successful Control of monocotyledon and dicotyledon weeds in monocotyledons and dicotyledons Use crops such as wheat, corn or soy.

The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Active ingredient-impregnated natural and synthetic substances, fine encapsulation in po lymeric fabrics.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients are under pressure with extenders, i.e. liquid solvents the liquefied gases and / or solid carriers, if necessary with use formation of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents.

In the case of the use of water as an extender, e.g. B. also organic Lö be used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, alkylnaphthalenes,  chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobes zoles, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as Cyc lohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, alcohol get, such as butanol or glycol and their ethers and esters, ketones, such as acetone, Methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents tel, such as dimethylformamide or dimethyl sulfoxide, and water.

As solid carriers come into question: B. ammonium salts and natural Ge stone powders such as kaolins, clays, talc, chalk, quartz, attapulgite, Montmoril lonite or diatomaceous earth and synthetic rock powder, such as highly disperse pebbles acid, alumina and silicates; as solid carriers for granules are: e.g. B. broken and fractionated natural rocks such as calcite, marble, Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules made from organic material such as sawdust, coconut bowls, corn cobs and tobacco stalks; as emulsifier and / or foam generator Funds are possible: B. non-ionic and anionic emulsifiers, such as poly oxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polygly colethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; when Dispersants come into question: z. B. Ligninsulfitablaugen and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic, powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholi pide, such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferrocy blue and organic dyes such as alizarin, azo and metal phthalocyanine substances and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.  

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example amlides, such as e.g. B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. dichloropicolinic acid, Di camba or picloram; Aryloxyalkanoic acids, such as. B. 2,4-D, 2,4-DB, 2,4-DP, fluroxy pyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as. B. Diclo fop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop- ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, e.g. B. chlorine propham, Desmedipham, Phenmedipham and Propham; Chloroacetanilides such as e.g. B. Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor and Propa chlorine; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and Trifluralin; Diphenyl ether, such as B. Acifluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; Ureas, such as B. chlorotoluron, diuron, huometuron, isoproturon, Linuron and methabenzthiazuron; Hydroxylamines, such as. B. alloxydim, clethodim, Cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imazamethabenz, imazapyr and imazaquin; Nitriles such as B. bromoxynil, dichlobenil and ioxynil; Oxyacetamides such as e.g. B. Mefenacet; Sulfonylureas, such as. B. Amido sulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, Metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfu ron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. butylates, Cycloate, Diallate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb and Triallates, triazines, such as. B. Atrazin, Cyanazin, Sunazin, Simetryne, Terbutryne and Terbutylazin; Triazinones such as e.g. B. hexazinone, metamitron and metribuzin; other such as B. aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, Difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufossinate, glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.

Also a mixture with other known active ingredients, such as fungicides, insecticides the, acanzides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.  

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use solder solutions, suspensions, emulsions, powders, pastes and granules. The application is done in the usual way, e.g. B. by pouring, spraying; Spraying, Scatter.

The active compounds according to the invention can be used both before and after emergence of the plants are applied.

They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. they depends essentially on the type of effect desired. Generally lie The application rates between 0.001 and 10 kg of active ingredient per hectare of soil che, preferably between 0.005 and 5 kg per hectare.

The manufacture and use of the active compounds according to the invention are based on following examples.

Manufacturing examples example 1

2.66 g (0.01 mol) of 2-trifluoromethyl-bromopyridino- [1H] -imidazole (A1 / A2) and 1.75 ml (0.0125 mol) of triethylamine are dissolved in 100 ml of dichloromethane. 1.25 ml (0.0125 mol of chloromethyl methyl ether) are added dropwise, the mixture is then heated to the reflux temperature and stirred at the reflux temperature for 16 hours. For working up, the cooled reaction mixture is washed three times with 30 ml of water each time, dried over MgSO ₄ and in vacuo concentrated and the residue purified by chromatography on silica gel (mobile solvent: dichloromethane).

2.40 g (74% of theory) of 1-ethoxymethyl-2-trifluoromethyl-bromopyridino imidazole are obtained as a mixture of regioisomers (B1 / B2) in a ratio of 60:40 (mp: 68 ° C.).
¹ H NMR (CDCl ₃ / tetramethylsilane): δ = 5.68 (s, 2H); 5.85 (s, 2H) ppm (each N-CH ₂ -O-).

By recrystallization with an ether / petroleum ether mixture, the Separate isomers from each other.

The compounds listed in the table below are obtained analogously.  

Table II

The ¹ H-NMR spectra were recorded in deuterochloroform (CDCl ₃ ) with tetra methylsilane (TMS) as the internal standard. The chemical shift is given as a δ value in ppm; in all cases the shift of the NC H ₂ R ¹ R ² protons is given.

Example A Pre-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

A Ge is mixed to produce a suitable preparation of active compound most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil and after 24 hours doused with the active ingredient preparation. You keep the amount of water per Area unit expediently constant. The active ingredient concentration in the accessory Horse riding is irrelevant, the only decisive factor is the amount of the active ingredient per unit area. After three weeks, the degree of damage to the plants bo in% damage compared to the development of the untreated control.

It means:
0% = no effect (like untreated control)
100% = total annihilation.

A clear superiority in effectiveness with comparable crop plants In this test, the compounds according to the preparation examples (1) show selectivity. and (6).  

Example B Post emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

A Ge is mixed to produce a suitable preparation of active compound most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5 to 15 cm so that the desired amounts of active ingredient per unit area be applied. After three weeks, the degree of damage to the plants bo in% damage compared to the development of the untreated control.

It means:
0% = no effect (like untreated control)
100% = total annihilation.

A clear superiority in effectiveness as well as in crop plants The compounds according to the preparation examples show selectivity in this test (1), (6) and (12).

Claims (9)

1. New, substituted, hetero-fused imidazoles of the general formula (I) in which
R ^{1 represents} hydrogen or a straight-chain or branched, optionally unsubstituted or substituted radical of the series alkyl, alkoxy or aryl,
R ^{2 is} hydroxyl, cyano or a straight-chain or branched, optionally unsubstituted or substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl oxy, dialkoxyphosphonyl, (hetero ) Aryl, (hetero) arylcarbonyl, (hetero) - aryloxycarbonyl, (hetero) arylcarbonyloxy or (hetero) arylaminocarbenylaminocarbonyloxy,
R ^{3 represents} cyano, halogen or a straight-chain or branched radical which is optionally unsubstituted or substituted in the alkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkynyloxy, dialkoxyphosphonyl, amino, amino carbonyl or aryl radical,
A ¹ , A ² , A ³ and A ⁴ each represent optionally N (nitrogen), N-CHR ¹ R ² or CX, with at least one but at most two nitrogen atoms occurring simultaneously in the hetero-fused ring and all positional isomers being possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ^{2 are} in the case of two nitrogen atoms and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted (R ³ ),
wherein
X ¹ , X ² and X ³ each independently of one another for hydrogen, halogen, cyano, nitro or for a straight-chain or branched, each optionally unsubstituted or substituted radical of the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, for hydroxycarbonyl , Alkylcarbonyl, alkoxycarbonyl, cycloalkyloxy carbonyl, for in each case optionally substituted amino or amino carbonyl, or for in each case optionally substituted aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryl oxycarbonyl, arylazo or arylthiomenten, but at least one of the substituents X ¹ , X ² or X ³ for haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyl, for optionally substituted, fused-in dioxyalkylene, for hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, for each optionally substituted amino or the aminocarbonyl or represents optionally substituted aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl. 2. New, substituted, hetero-fused imidazoles of the general formula (I) according to claim 1, characterized in that
R ^{1 represents} hydrogen or a straight-chain or branched, optionally unsubstituted or substituted radical of the series alkyl, alkoxy each having 1 to 8 carbon atoms or optionally mono- or polysubstituted, identically or differently substituted, phenyl, the following being suitable as substituents:
Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or halogen alkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 same or different halogen atoms, each straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, optionally singly or multiply, identically or differently by halogen and / or straight-chain or branched alkyl 1 to 6 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms substituted, doubly linked dioxyalkylene with 1 to 5 carbon atoms or optionally single or multiple, identical or v phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
R ² for hydroxy, cyano or for a straight-chain or branched and each optionally mono- or polysubstituted, identically or differently substituted radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each with up to is 8 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, the substituents in each case being:
Fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 8 carbon atoms or in each case optionally mono- or polysubstituted, identically or differently substituted aryl having 6 to 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 5 heteroatoms - in particular nitrogen, Oxygen and / or sulfur - is available, the aryl or heteroaryl substituents mentioned in R ^{1 being} suitable,
R ² furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents in each case being:
Formyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 8 carbon atoms, in each case, if appropriate, singly or twice, in the same way or differently, by straight-chain or branched alkyl having 1 to 8 Carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 8 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio carbonyl, alkoxy-thiocarbonyl or carbonthio-1-thiocarbonyl in each case with 1-thiocarbonyl or branched alkyl parts, in each case double-linked and ring-closed alkane diylcarbonyl or alkanediyloxycarbonyl, each having 2 to 6 carbon atoms in the alkanediyl part, in each case optionally in the aryl part once or several times, identically or differently hieden substituted arylalkyl, aryl alkylcarbonyl or arylalkyloxycarbonyl each having 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the aryl part mono- or polysubstituted, identically or differently, aryl, arylcarbonyl or aryloxycarbonyl, each with 6 to 10 Carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ² also represents aryl, arylcarbonyl, aryloxycarbonyl, aryl carbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which is mono- or polysubstituted by identical or different substituents, each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ² also for heteroaryl, heteroarylcarbonyl, heteroaryloxy carbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocar bonyloxy, each of which is mono- or polysubstituted by identical or different substituents, each having 2 to 9 carbon atoms and 1 to 5 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - im Heteroaryl part, where the aryl substituents mentioned for R ¹ are suitable as heteroaryl substituents,
R ³ for cyano, fluorine, chlorine, bromine, iodine or for a straight-chain or branched, each optionally unsubstituted or substituted radical from the series cycloalkyl, alkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkenyloxy each with up to 8 carbon atoms in the individual alkyl, alkenyl or alkynyl parts, the possible substituents in each case being: fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 8 carbon atoms or, in each case, optionally mono- or polysubstituted, identically or differently substituted, aryl with 6 up to 10 carbon atoms or heteroaryl with 2 to 9 carbon atoms and 1 to 5 heteroatoms - in particular nitrogen, oxygen and / or sulfur -, the aryl or heteroaryl substituents mentioned in R ^{1 being} suitable,
R ³ furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents in each case being:
Formyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 8 carbon atoms, in each case, if appropriate, singly or twice, identically or differently, by straight-chain or branched alkyl having 1 to 8 carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 8 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio carbonyl, alkoxy-thiocarbonyl or alkylthio-1-thiocarbon straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkane diylcarbonyl or alkanediyloxycarbonyl, each having 2 to 6 carbon atoms in the alkanediyl part, in each case optionally in the aryl part once or several times, identically or verse The substituted arylalkyl, arylalkyl carbonyl or arylalkyloxycarbonyl, each having 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the aryl part, singly or multiply, identically or differently substituted aryl, arylcarbonyl or aryloxycarbonyl, each with 6 to 10 Carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ³ also represents aryl which is optionally mono- or polysubstituted, identically or differently, each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
A ¹ , A ² , A ³ and A ⁴ each optionally represent N (nitrogen), N-CHR ¹ R ² or CX, where at least one but at most two nitrogen atoms occur simultaneously in the hetero-fused ring and all positional isomers are possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ² are present with two nitrogen atoms and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted (R ³ ) and
X ¹ , X ² , X ³ each independently of one another for hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, for each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms, for cycloalkyl 3 to 8 carbon atoms, each for straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms or for optionally single or multiple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, doubly linked dioxyalkylene having 1 to 5 carbon atoms, moreover for hydroxycarbonyl, for each straight-chain or branched alkyl carbonyl or alkoxycarbonyl, each with 1 to 6 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3 to 8 carbon atoms in the cycloalkyl part, or for in each case monosubstituted or polysubstituted, identically or differently substituted, amino or aminocarbonyl, the following being suitable as amino substituents:
in each case straight-chain or branched alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or alkylcarbonyl each having 1 to 6 carbon atoms in the individual alkyl parts or in the aryl part, in each case optionally singly or multiply, identically or differently substituted arylcarbonyl, arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ;
X ¹ , X ² , X ³ also for aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxy carbonyl, arylthiomethylsulfonyl or arylazo, each with 6 to 10 carbon atoms in the aryl part, each being mono- or polysubstituted in the aryl part, one or more times, identically or differently stand, the aryl substituents in each case those mentioned in R ¹ and
where at least one of the substituents X ¹ , X ² or X ³ each represents ge-chain or branched haloalkyl, haloalkoxy, haloalkyl thio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, for straight-chain or branched alkylsulfonyl having 1 to 6 carbon atoms or for optionally single or multiple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different Halogen atom-substituted, double-linked dioxyalkylene with 1 to 5 carbon atoms, also for hydroxycarbonyl, for straight-chain or branched alkylcarbonyl or alkoxycarbonyl each with 1 to 6 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3 to 8 carbon atoms in the cycloalkyl part or represents in each case optionally mono- or polysubstituted, identical or differently substituted amino or aminocarbonyl, the amino substituents in each case being suitable: straight-chain or branched alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or Alkylcarbonyl, each having 1 to 6 carbon atoms in the individual alkyl parts or in the aryl part, optionally one or more times, identically or differently substituted arylcarbonyl, arylsulfonyl, arylaminocarbonyl or arylmethyl sulfonyl, each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those in R ¹ mentioned in question;
X ¹ , X ² , X ³ also represent aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo, each with 6 to 10 carbon atoms in the aryl part, each of which is mono- or polysubstituted in the aryl part, one or more times, identically or differently, the aryl substituents in each case those mentioned in R ¹ come into question. 3. New, substituted, hetero-fused imidazoles of the general formula (I) according to claim 1, characterized in that
R ^{1 represents} hydrogen, or an unsubstituted or substituted, straight-chain or branched radical of the series alkyl, alkoxy each having 1 to 6 carbon atoms or optionally mono- to trisubstituted, identically or differently substituted, phenyl, the following being suitable as substituents:
Fluorine, chlorine, bromine, iodine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, each with 1 up to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each with 1 to 4 carbon atoms in the individual alkyl parts, optionally single to six times, identical or different, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, substituted, double-linked dioxyalkylene having 1 to 4 carbon atoms or, if appropriate, one to five times, gle I or different phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, where halogen is in each case fluorine, chlorine, bromine Iodine stands
R ² for hydroxy, cyano or for a straight-chain or branched radical which is optionally monosubstituted to pentas, identically or differently, substituted by fluorine, chlorine, bromine or iodine, and is a radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl , Alkylcarbonyloxy or dialkoxyphosphonyl each having up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl parts or for each optionally optionally mono- to trisubstituted, identically or differently substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, Alkylcarbonyloxy or dialkoxyphosphonyl, each with up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl parts, where the following are suitable as substituents:
straight-chain or branched alkoxy with 1 to 6 carbon atoms or each optionally mono- to trisubstituted, identically or differently substituted aryl with 6 or 10 carbon atoms or heteroaryl with 2 to 9 carbon atoms and 1 to 4 heteroatoms - in particular nitrogen, oxygen and / or sulfur -, where the aryl or heteroaryl substituents mentioned in R ^{1 are} suitable,
R ² furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents in each case being:
Formyl, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 6 carbon atoms, each optionally single or double, identical or different, by straight-chain or branched alkyl 1 to 6 carbon atoms substituted carbamoyl, thiocarbamoyl or sulf amoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 7 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio carbonyl, alkoxy-thiocarbonyl or 6-carbonyl-1-carbonyl-alkyl-carbonyl in the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkane diylcarbonyl or alkanediyloxycarbonyl, each having 2 to 5 carbon atoms in the alkanediyl part, in each case in the aryl part, in each case simply to triple, identical or ve Arylalkyl, arylalkyl carbonyl or arylalkyloxycarbonyl with 6 or 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the straight-chain or branched alkyl part or in the aryl part, in each case optionally in the aryl part, mono- to triple, identically or differently substituted, aryl, arylcarbonyl or aryloxycarbonyl, each with 6 or 10 Part of the carbon atoms in the aryl, the aryl substituents in each case being those mentioned in R ¹ ,
R ² also represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which has from 6 to 10 carbon atoms in the aryl part and is optionally monosubstituted to fivefold, identical or different, the aryl substituents in each case being those mentioned in R ¹ ,
R ² also for heteroaryl, heteroarylcarbonyl, heteroaryloxycar bonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocar bonyloxy each having from one to five times, the same or differently substituted, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylcarbonyloxy or bonyloxy each having 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms - especially nitrogen, oxygen and / or sulfur in the heteroaryl part, the aryl substituents mentioned for R ^{1 being} suitable as heteroaryl substituents,
R ³ for cyano, fluorine, chlorine, bromine, iodine or for a straight-chain or branched, optionally single to five times, the same or different substituted by fluorine, chlorine, bromine and / or iodine radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy , Alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl or alkylcarbonyloxy, each having up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl parts or for cycloalkyl, alkyl, alkenyl, alkynyl, alkynyl, alkoxy, alkenyloxy, which are optionally monosubstituted to trisubstituted or substituted. Alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each with up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, the following being suitable as substituents:
Fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 6 carbon atoms or in each case optionally single to triple, identical or differently substituted aryl having 6 or 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 4 heteroatoms - in particular nitrogen , Oxygen and / or sulfur -, where the aryl or heteroaryl substituents mentioned in R ^{1 are} suitable,
R ³ furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents in each case being:
Formyl, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 6 carbon atoms, each optionally single or double, identical or different, by straight-chain or branched alkyl 1 to 6 carbon atoms substituted carbamoyl, thiocarbamoyl or sulf amoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 7 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio carbonyl, alkoxy-thiocarbonyl or 6-carbonyl-1-carbonyl-alkyl-carbonyl in the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkane diylcarbonyl or alkanediyloxycarbonyl, each having 2 to 5 carbon atoms in the alkanediyl part, in each case in the aryl part, in each case simply to triple, identical or ve Arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl with 6 or 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the straight-chain or branched alkyl part or in the aryl part, in each case optionally in the aryl part, monosubstituted to triple, identically or differently substituted, aryl, arylcarbonyl or aryloxycarbonyl, each with 6 or 10 Carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
R ³ also represents aryl, each of which is monosubstituted to pentas, the same or different, each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,
A ¹ , A ² , A ³ and A ⁴ each optionally represent N (nitrogen), N-CHR ¹ R ² or CX, where at least one but at most two nitrogen atoms occur simultaneously in the hetero-fused ring and all positional isomers are possible, so that
CX ¹ , CX ² , CX ^{3 are present} with one nitrogen atom and CX ¹ and CX ² with two nitrogen atoms and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted (R ³ ) is present and
X ¹ , X ² , X ³ each independently of one another for hydrogen, fluorine, chlorine, bromine, cyano, nitro, for straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, for cycloalkyl having 3 to 7 carbon atoms, each for straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or for optionally up to six times, identically or differently, by halogen and / or straight-chain or branched Al kyl with 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, doubly linked dioxyalkylene with 1 to 4 carbon atoms, also for hydroxycarbonyl, for each straight-chain or branched alkylcarbo nyl or Alkoxycarbonyl, each with 1 to 4 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3 to 7 carbon atoms in the cycloalkyl part, or for in each case monosubstituted or disubstituted, identically or differently substituted amino or aminocarbonyl, the following being suitable as amino substituents:
each straight-chain or branched alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alkoxyalkyl or alkylcarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts or in the aryl part, in each case optionally up to five times, identical or differently substituted arylcarbonyl , Arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ;
X ¹ , X ² , X ³ also for each aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxy carbonyl, arylthiomethylsulfonyl or arylazo, each having 6 or 10 carbon atoms in the aryl part, each mono- to fivefold, the same or differently substituted in the aryl part stand, the aryl substituents in each case those mentioned in R ¹ and
where at least one of the substituents X ¹ , X ² , X ³ for each straight-chain or branched haloalkyl haloalkoxy, halogen alkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, for straight-chain or branched alkylsulfonyl having 1 up to 4 carbon atoms or for optionally up to six times, identical or different, substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, doubly linked dioxyalkylene with 1 to 4 carbon atoms also stands for hydroxy carbonyl, for straight-chain or branched alkylcarbonyl or alkoxycarbonyl each with 1 to 4 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3 to 7 carbon atoms in the cycloalkyl part or for each is optionally mono- or disubstituted, identical or differently substituted amino or aminocarbonyl, the amino substituents in each case being:
each straight-chain or branched alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alkoxyalkyl or alkylcarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts or in the aryl part, each optionally monosubstituted to pentuply, identically or differently substituted Arylcarbonyl, arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl, each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ;
X ¹ , X ² , X ³ also for aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo, each with 6 or 10 carbon atoms in the aryl part, such as in the aryl part, monosubstituted to pentasubstituted, identically or differently, in each case Are phenyl or naphthyl, the aryl substituents in each case being those mentioned in R ¹ . 4. New, substituted, hetero-fused imidazoles of the general formula (I) according to claim 1, characterized in that
R ^{1 represents} hydrogen or an optionally unsubstituted or substituted straight-chain or branched radical of the series alkyl, alkoxy each having 1 to 4 carbon atoms or optionally mono- or disubstituted, identically or differently substituted phenyl, the following being suitable as substituents:
Fluorine, chlorine, bromine, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 3 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 3 Carbon atoms and 1 to 7 identical or different halogen atoms, each straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl each having 1 to 3 carbon atoms in the individual alkyl parts, optionally one to four times, identical or different, by halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms substituted, doubly linked dioxyalkylene having 1 to 3 carbon atoms or optionally single to triple, same h or phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, where halogen is in each case fluorine, chlorine, Bromine stands,
R ² for hydroxyl, cyano or for a straight-chain or branched radical which is optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine and / or bromine and is substituted in the alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl group , Alkylcarbonyloxy or dialkoxyphosphonyl each having up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl parts, or for each optionally mono- or disubstituted, identically or differently substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, Alkoxycarbonyl, alkyl carbonyloxy or dialkoxyphosphoryl, each with up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, the following being suitable as substituents:
straight-chain or branched alkoxy having 1 to 3 carbon atoms or optionally mono- or disubstituted, identically or differently substituted phenyl, the phenyl substituents mentioned in R ^{1 being} suitable,
R ² furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents in each case being:
Formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 4 carbon atoms, each optionally single or double, identical or different, by straight-chain or branched alkyl 1 to 4 carbon atoms substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each with 3 to 6 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenyl carbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl-bis-carbonyl or alkylthio-carbonyl or alkylthio-carbonyl 4 carbon atoms in the individual straight-chain or branched alkyl parts, each double-linked and ring-closed alkyldiyl carbonyl or alkanediyloxycarbonyl, each with 2 to 4 carbon atoms in the alkanediyl part, each optionally in the phenyl part single or double, the same as above the differently substituted phenylalkyl, phenylalkyl carbonyl or phenylalkyloxycarbonyl each having 1 to 4 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the phenyl part mono- or disubstituted, identically or differently substituted phenyl, phenylcarbonyl or phenyloxy carbonyl, the phenyl substituents in each case those mentioned in R ¹ come into question
R ² also represents phenyl, phenylcarbonyl, phenyloxycarbonyl, phenylcarbonyloxy or phenylaminocarbonylaminocarbonyloxy, each of which is monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents in each case those mentioned in R ^{1 being} suitable,
R ² also for heteroaryl, heteroarylcarbonyl, heteroaryloxycar bonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocar bonyloxy each having from one to three times the same or differently substituted, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylcarbonyloxy or bonyloxy each having 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur is in the heteroaryl part, the heteroaryl substituents in each case being the phenyl substituents mentioned for R ¹ ,
R ³ for cyano, fluorine, chlorine, bromine or for a straight-chain or ver branched, optionally monosubstituted to trisubstituted by fluorine, chlorine and / or bromine, the rest of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio , Alkyl carbonyl, alkoxycarbonyl, alkylcarbonyloxy, each having up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl moieties, or for each optionally mono- or disubstituted, identically or differently substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio , Alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphoryl each having up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl parts, the substituents in each case being:
straight-chain or branched alkoxy having 1 to 3 carbon atoms or optionally mono- or disubstituted, identically or differently substituted phenyl, the phenyl substituents mentioned in R ^{1 being} suitable,
R ³ furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, the substituents in each case being:
Formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain or branched alkylsulfonyl having 1 to 4 carbon atoms, each optionally single or double, identical or different, by straight-chain or branched alkyl 1 to 4 carbon atoms substituted carbamoyl, thiocarbamoyl or sulf amoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio carbonyl, alkoxy-thiocarbonyl or 4-carbonyl-1-carbonyl-alkyl-carbonyl in the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkane diylcarbonyl or alkanediyloxycarbonyl, each having 2 to 4 carbon atoms in the alkanediyl part, in each case optionally in the phenyl part single or double, identical or differently substituted phenylalkyl, phenylalkylcarbonyl or phenylalkyloxycarbonyl each having 1 to 4 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the phenyl part mono- or disubstituted, identically or differently substituted phenyl, phenylcarbonyl or phenyloxycarbonyl, the phenyl substituents in each case being those mentioned in R ¹ Question come
R ³ also represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents in each case being those mentioned for R ¹ ,
A ¹ , A ² , A ³ and A ⁴ each optionally represent N (nitrogen), N-CHR ¹ R ² or CX, where at least one but at most two nitrogen atoms occur simultaneously in the hetero-fused ring and all positional isomers are possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ² are present with two nitrogen atoms and if either A ¹ , A ² , A ³ or A ⁴ stand for N-CHR ¹ R ² , the imidazole ring is only monosubstituted and
X ¹ , X ² , X ³ independently of one another each for hydrogen, chlorine, bromine, cyano, nitro, for each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, for cycloalkyl having 3, 5 or 6 carbon atoms, for each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms or for optionally up to four times, identical or different, by halogen and / or straight-chain or branched alkyl with 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, substituted, double-linked dioxyalkylene with 1 to 3 carbon atoms, furthermore for hydroxycarbonyl, for each straight-chain or branched alkyl carbonyl or Alkoxycarbonyl each with 1 to 3 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3, 5 or 6 carbon atoms in the cycloalkyl part or for in each case monosubstituted or disubstituted, identically or differently substituted amino or aminocarbonyl, the amino substituents in each case being:
each straight-chain or branched alkyl having 1 to 3 carbon atoms, haloalkyl having 1 to 3 carbon atoms and 1 to 7 halogen atoms, alkoxyalkyl or alkylcarbonyl each having 1 to 3 carbon atoms in the individual alkyl parts or in the phenyl part, in each case optionally up to three times, identical or differently substituted phenylcarbonyl , Phenylsulfonyl, phenylaminocarbonyl or phenylmethyl sulfonyl, the phenyl substituents in each case being those mentioned in R ¹ ;
X ¹ , X ² , X ³ also represent phenyl, phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulfonyl or phenylazo, each of which is monosubstituted to trisubstituted in the phenyl part in one to three times, identically or differently, phenyloxycarbonyl, phenylthiomethylsulfonyl or phenylazo, the phenyl substituents in each case being the phenyl substituents R ¹ mentioned come into question and
where at least one of the substituents X ¹ , X ² , X ³ for straight-chain or branched haloalkyl, haloalkoxy, halogen alkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, for straight-chain or branched alkylsulfonyl 1 to 3 carbon atoms or for optionally monosubstituted to tetrasubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms , doubly linked dioxyalkylene with 1 to 3 carbon atoms, also for hydroxy carbonyl, for each straight-chain or branched alkylcarbonyl or alkoxycarbonyl each with 1 to 3 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl with 3, 5 or 6 carbon atoms in the cyclo alkyl part or represents in each case monosubstituted or disubstituted, identically or differently substituted amino or aminocarbonyl, the following being suitable as amino substituents:
in each case straight-chain or branched alkyl having 1 to 3 carbon atoms, haloalkyl having 1 to 3 carbon atoms and 1 to 7 halogen atoms, alkoxyalkyl or alkylcarbonyl each having 1 to 3 carbon atoms in the individual alkyl parts or in the phenyl part, each optionally monosubstituted to triple, identically or differently substituted Phenylcarbonyl, phenylsulfonyl, phenylaminocarbonyl or phenylmethyl sulfonyl, where the phenyl substituents mentioned in R ^{1 are} suitable;
X ¹ , X ² , X ³ also for phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulfonyl or phenylazo, each of which is monosubstituted to trisubstituted by identical or different substituents in the phenyl part, in each case those mentioned in R ¹ as phenyl substituents Question come. 5. Process for the preparation of new, substituted, fused imidazoles of the general formula (I) in which
R ^{1 represents} hydrogen or a straight-chain or branched, optionally unsubstituted or substituted radical of the series alkyl, alkoxy or aryl,
R ² for hydroxy, cyano or for a straight-chain or branched, in each case optionally unsubstituted or substituted radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl oxy, dialkoxyphosphonyl, (hetero ) Aryl, (hetero) arylcarbonyl, (hetero) - aryloxycarbonyl, (hetero) arylcarbonyloxy or (hetero) arylaminocar bonylaminocarbonyloxy,
R ^{3 represents} cyano, halogen or a straight-chain or branched, in each case optionally unsubstituted or substituted radical of the series alkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkynyloxy, amino, aminocarbonyl or aryl,
A ¹ , A ² , A ³ and A ⁴ each represent optionally N (nitrogen), N-CHR ¹ R ² or CX, with at least one but at most two nitrogen atoms occurring simultaneously in the hetero-fused ring and all positional isomers being possible, so that
CX ¹ , CX ² , CX ³ with a nitrogen atom and
CX ¹ and CX ^{2 are} in the case of two nitrogen atoms and if either A ¹ , A ² , A ³ or A ^{4 are} N-CHR ¹ R ² , the imidazole ring is only monosubstituted,
wherein
X ¹ , X ² and X ³ each independently of one another for hydrogen, halogen, cyano, nitro or for a straight-chain or branched, each optionally unsubstituted or substituted radical of the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, for hydroxycarbonyl , Alkylcarbonyl, alkoxycarbonyl, cycloalkyloxy carbonyl, for in each case optionally substituted amino or amino carbonyl, or for in each case optionally substituted aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryl oxycarbonyl, arylazo or arylthiomenten, but at least one of the substituents X ¹ , X ² or X ³ for haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyl, for optionally substituted, fused-in dioxyalkylene, for hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, for each optionally substituted amino or the aminocarbonyl or represents optionally substituted aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl,
characterized in that one
1H-substituted hetero-fused imidazoles of the formula (II), in which
A ¹ , A ² , A ³ , A ⁴ and R ^{3 have} the meanings given above, with compounds of the formula (III), in which
M stands for a suitable leaving group,
R ¹ and R ^{2 have} the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary. 6. Herbicidal agents, characterized by a content of at least one Substituted, hetero-fused imidazole of the formula (I) according to the claims 1 to 5. 7. Process for combating undesirable plants, thereby characterized in that substituted, hetero-fused imidazoles of the general my formula (I) according to claims 1 to 5 on plants and / or their Living space. 8. Use of substituted, hetero-fused imidazoles of the general Formula (I) according to claims 1 to 5 for combating undesirable Plants. 9. A process for the preparation of herbicidal compositions, characterized in that substituted, hetero-fused imidazoles of the general formula (I) according to of claims 1 to 5 with extenders and / or surface-active sub punch mixed.