EP0690861A1

EP0690861A1 - Substituted heteroannulated imidazoles and their use as herbicides

Info

Publication number: EP0690861A1
Application number: EP94911881A
Authority: EP
Inventors: Bernd Baasner; Folker Lieb; Hans-Joachim Santel; Markus Dollinger
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1993-03-26
Filing date: 1994-03-14
Publication date: 1996-01-10
Also published as: DE4309969A1; JPH08508268A; CA2158996A1; WO1994022859A1; AU6425794A

Abstract

New substituted heteroannulated imidazoles having general formula (I), in which R<1>, R<2>, R<3>, A<1>, A<2>, A<3> and A<4> have the meanings given in the description, are disclosed, as well as a process for preparing the same and their use as herbicides.

Description

SUBSTITUTED, HETEROANELLATED IMIDAZOLES AND THEIR USE AS HERBICIDES

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

It is known that certain benzimidazoles have insecticidal properties, but nothing has yet been known about the use of hetero-fused imidazoles as herbicides.

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 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, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero) Aryl, (hetero) arylcarbonyl, (hetero) aryloxycarbonyl, (hetero) arylcarbonyloxy or (hetero) arylaminocarbonylaminocarbonyloxy, 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 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} for one nitrogen atom and CX ¹ and CX ^{2 are} for 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 in which

X ¹ , X ² and X ³ each independently of one another for hydrogen, halogen, cyano, nitro or for a straight-chain or branched, in each case 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 arylthiituentene, but at least one of which is, but at least one of the substituents being 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 Aminocarbonyl or for optionally substituted aryl, arylthio, arylsulfinyl, arylsulfonyl, Arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl is found.

Depending on the type and number of the substituents, the compounds of the formula (I) can optionally be present 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:

Furthermore, it was found that the new substituted, hetero-fused imidazoles of the general formula (I)

in which

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, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero) Aryl, (hetero) arylcarbonyl, (hetero) aryloxycarbonyl, (hetero) -

Arylcarbonyloxy or (hetero) arylaminocarbonylaminocarbonyloxy,

R ^{3 represents} cyano, halogen or a straight-chain or branched radical which is optionally unsubstituted or substituted in the alkyl series, 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 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 ), in which

X ¹ , X ² and X ³ each independently of one another for hydrogen, halogen, cyano, nitro or for a straight-chain or branched, in each case optionally unsubstituted or substituted radical of the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, for hydroxycarbonyl , Alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, for each optionally substituted amino or aminocarbonyl, or for each optionally substituted aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl, but at least one of which are Substituents X ¹ , X ² or X ³ for haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyl, for optionally substituted, fused-on dioxyalkylene, for hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl,

Cycloalkyloxycarbonyl, represents in each case optionally substituted amino or aminocarbonyl or for in each case optionally substituted aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl, obtained if a) substituted 1H-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 represents 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.

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-fused imidazoles of the general formula (I) according to the invention show a considerable herbicidal activity against problem weeds and, at the same time, a comparatively good tolerance to important crop plants. 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 phenyl which is monosubstituted or polysubstituted by identical or different substituents, 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 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 singly or multiply, identically or differently by halogen and / or straight-chain or branched alkyl with 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 different are 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 in each case optionally mono- or polysubstituted, identical or differently substituted

Radical of the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy,

Alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each with up to 8 carbon atoms in the individual alkyl or Alkenyl or alkynyl is available, 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, identical or differently substituted aryl having 6 to 10 carbon atoms or

Heteroaryl with 2 to 9 carbon atoms and 1 to 5 heteroatoms - in particular nitrogen, oxygen and / or sulfur - is, wherein as aryl or. Heteroaryl substituents which come into question for R ¹ , furthermore in each case optionally represent mono- or disubstituted, identically or differently substituted amino or aminocarbonyl, the following being possible 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, 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 alkylthio-1-carbonyl or alkylthio-thi

8 carbon atoms in the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each with 2 to 6 carbon atoms in the alkanediyl part, in each case optionally in the aryl part, singly or multiply, identically or differently substituted arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl with in each case 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, substituted aryl, arylcarbonyl or aryloxycarbonyl each having 6 to 10 carbon atoms in the aryl part, the aryl substituents in each case being those in R ¹ mentioned. R ² also represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy 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, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each of which is optionally 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 represents} cyano, fluorine, chlorine, bromine, iodine or a straight-chain or branched, 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 substituents in each case being suitable: fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy with 1 to 8 carbon atoms or, in each case, simply or multiply, identically or differently substituted

Aryl with 6 to 10 carbon atoms or heteroaryl with 2 to 9 carbon atoms and 1 to 5 heteroatoms - in particular nitrogen, oxygen and / or sulfur -, where aryl or heteroaryl substituents which are mentioned in R ¹ are possible, R ³ also for each optionally mono- or disubstituted, identical or differently substituted amino or aminocarbonyl, where the following are suitable as substituents:

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 carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each having 3 to 8 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, optionally mono- or disubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 8 carbon atoms - Thio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each with 1 to 8 carbon atoms in the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each with 2 to 6 carbon atoms in the alkanediyl part, in each case optionally in the aryl part or multiply, identically or differently 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 given lls in the aryl part mono- or polysubstituted, identical 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 at 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 in each case straight-chain or branched alkyl, alkoxy, Alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms, for cycloalkyl having 3 to 8 carbon atoms, for each 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 double-linked dioxyalkylene which is 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 haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms 1 to 5 carbon atoms are also hydroxycarbonyl, each straight-chain or branched alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl part or for in each case s are 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 with 1 to 6 carbon atoms in the individual alkyl parts or in the aryl part, each optionally mono- or polysubstituted, 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 those mentioned in R ¹ come into question; X ¹ , X ² , X ³ also for aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo, each having 6 to 10 carbon atoms in the aryl part, mono- or polysubstituted, identically or differently, in the Aryl are part, the aryl substituents being those mentioned in R ¹ and where at least one of the substituents X ¹ , X ² or X ³ for each 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, for straight-chain or branched alkylsulfonyl with 1 to 6 carbon atoms or for optionally single or multiple, 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 haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - ized, 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 represents in each case optionally mono- or polysubstituted, identical or differently substituted amino or aminocarbonyl, where as

Amino substituents are in each case possible: 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, if appropriate in each case Arylcarbonyl, arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl, each having 6 to 10 carbon atoms in the aryl part, mono- or polysubstituted by identical or different substituents, the aryl substituents in each case being those mentioned in 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, where aryl substituents in each case are 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 6 carbon atoms or for optionally monosubstituted 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 having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, 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, alkoxy-alkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each with 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, double-linked dioxyalkylene having 1 to 4 carbon atoms or optionally single to five times, identical or different, by halogen and / or straight-chain or branched alkyl having 1 up 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 phenyl, where halogen in each case represents fluorine, chlorine, bromine, iodine,

R ² for hydroxy, cyano or for a straight-chain or branched, in each case optionally up to five times, the same or different by fluorine, chlorine,

Bromine or iodine-substituted radicals from 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 simple up to triple, identical or differently substituted alkyl, alkenyl,

Alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each with up to 6 carbons Substance atoms in the individual alkyl or alkenyl or alkynyl parts, the substituents being in each case: 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 -, where aryl or heteroaryl substituents which are mentioned in R ¹ are possible, R ² furthermore each optionally mono- or disubstituted, identically or differently substituted Amino or aminocarbonyl, where the following are suitable as substituents:

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, in the same way 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-thi-1-carbonyl or alkylthio-thi

6 carbon atoms in the individual straight-chain or branched alkyl parts, each double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each with 2 to 5 carbon atoms in the alkanediyl part, in each case optionally in the aryl part, monosubstituted to triple, identically or differently 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 monosubstituted to triple, identically or differently substituted aryl, arylcarbonyl or aryloxycarbonyl each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ come into question R ² also represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which has one to five times the same or different substitution, each having 6 or 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 optionally mono- to pentasubstituted or identical or differently substituted, each having 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms - especially nitrogen, oxygen and / or sulfur - in

R ³ for cyano, fluorine, chlorine, bromine, iodine or for a straight-chain or branched, optionally single to five times, identical or different radicals of the series alkyl, alkenyl, substituted by fluorine, chlorine, bromine and / or iodine,

Alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl or alkylcarbonyloxy, each with up to 6 carbon atoms in the individual alkyl or alkenyl or alkynyl parts or for each optionally optionally up to triple, identical or differently substituted cycloalkyl, 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, where the following are in each case possible as substituents:

Fluorine, chlorine, bromine, iodine, 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 - where, as aryl or heteroaryl substituents, those mentioned in R ¹ are possible, R ³ furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, where the following are suitable as substituents:

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, in the same way 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-thiocarbonyl each having 1 to 6 carbon atoms in the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each with 2 Carbon atoms in the alkanediyl part, in each case optionally in the aryl part single to triple, identically or differently substituted arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl each having 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 in the aryl part simply to triple, identical or differently substituted aryl,

Arylcarbonyl or aryloxycarbonyl each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case being those mentioned in R ¹ ,

R ³ also for each aryl which is optionally mono- to pentasubstituted by identical or different substituents, 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, with at least one but at most two nitrogen atoms occurring simultaneously in the hetero-fused ring and all of them

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, 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 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, see below substituted, double-linked dioxyalkylene with 1 to 4 carbon atoms, moreover for hydroxycarbonyl, for each 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 in each case optionally single or double, same or differently substituted

Amino or aminocarbonyl, the amino substituents in each case being suitable: 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, the same 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 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 , where the aryl substituents in each case are those mentioned in R ¹ and where at least one of the substituents X ¹ , X ² , X ^{3 is} in each case 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, for straight-chain or branched alkylsulfonyl with 1 to 4 carbon atoms or for optionally single to six-fold, identical or different by halogen and / or straight-chain or branched alkyl with 1 to 4 carbon atoms and / or straight-chain or branched halogenoalkyl with 1 to 4 Kohlens toffatomen 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 represents in each case optionally mono- or disubstituted, identical or differently substituted amino or aminocarbonyl, the amino substituents in each case being suitable: 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 optionally up to five times, the same or differently substituted arylcarbonyl, arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl, in each case 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, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo each having 6 or 10 carbon atoms in the aryl part, such as phenyl or, in each case in the aryl part, monosubstituted to pentasubstituted, identically or differently Are naphthyl, the aryl substituents in each case being those mentioned in R ¹ .

Compounds of the formula (I) in which

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 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 with 1 to 3 carbon atoms in the individual alkyl parts, optionally one to four times, identically or differently, by halogen and / or straight-chain or branched alkyl 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, if appropriate, single to triple, identical or phenyl differently 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 in each case represents fluorine, chlorine, bromine, 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 parts, or for each optionally mono- or disubstituted, identically or differently substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl , Alkylcarbonyloxy or Dialkoxyphosphoryl each with up to 4 carbon atoms in the individual alkyl or alkenyl or

Alkynyl is available, the substituents in each case being suitable: straight-chain or branched alkoxy having 1 to 3 carbon atoms or optionally mono- or disubstituted, identically or differently substituted phenyl, where phenyl substituents are those mentioned for R ¹ , R ² also for each optionally single or doubly, identically or differently substituted amino or aminocarbonyl, where the following are suitable in each case:

Foπnyl, 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 having 1 to 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, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-1-carbonyl 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 4 carbon atoms in the alkanediyl part, in each case optionally in the phenyl part single or double, identical or variously 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, mono- or disubstituted, identically or differently substituted phenyl, phenylcarbonyl or phenyloxycarbonyl, the phenyl substituents in each case being those mentioned in R ¹ ,

R ² also stands for phenyl, phenylcarbonyl, phenyloxycarbonyl, phenylcarbonyloxy or phenylaminocarbonylaminocarbonyloxy, each of which is optionally monosubstituted to trisubstituted by identical or different means, the phenyl substituents in each case being those mentioned in R ¹ , R ² also each being optionally monosubstituted to triple, identically or differently Substituted heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each with 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 mentioned as the heteroaryl substituents mentioned in the case of the ¹ -phenoyl substituent ,

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 parts, 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, where the following are suitable in each case: straight-chain or branched alkoxy having 1 to 3 carbon atoms or optionally mono- or disubstituted, identically or differently substituted Phenyl, being the phenyl substituent in the case of R ¹ , R ³ furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, where the following are suitable as substituents:

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 substituted carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl part,

Alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each with 1 to 4 carbon atoms in the individual straight-chain or branched alkyl parts, in each case doubly linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each with 2 to 4 each optionally in the phenyl part monosubstituted or disubstituted, identically 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 monosubstituted or disubstituted, identically or differently substituted phenyl, phenylcarbonyl or phenyloxycarbonyl, where as phenyl substituents in each case those mentioned in R ¹ come into question,

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 under R ¹ ,

A ¹ , A ² , A ³ and A ⁴ each optionally represent N (nitrogen), N-CFR 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 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 in each case for hydrogen, chlorine, bromine, cyano, nitro, for in each case 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, halogen-substituted 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, double-linked dioxyalkylene having 1 to 3 carbon atoms are also hydroxycarbonyl, for each straight-chain or branched alkylcarbonyl or alkoxycarbonyl each having 1 to 3 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl having 3, 5 or 6 carbon atoms in the cycloalkyl part or for each given are also mono- or disubstituted, identical or differently substituted amino or aminocarbonyl, the amino substituents in each case being suitable: 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 up to 3 carbon atoms in the individual alkyl parts or in the phenyl part, each optionally monosubstituted to trisubstituted, identically or differently, 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, phenyloxy, phenylthio, phenylsulfonyl, phenylsulfonyl, phenylsulfonyloxy, phenylcarbonyl, phenyloxycarbonyl, which are monosubstituted to trisubstituted in the phenyl part in each case in the phenyl part, in one to three times Phenylthiomethylsulfonyl or phenylazo, where the phenyl substituents in each case are those mentioned in R ¹ and where at least one of the substituents X ¹ , X ² , X ^{3 is} in each case 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 to 3 carbon atoms or for optionally single to quadruple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched halogenoalkyl 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, 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 amino substituents in each case being suitable: 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 trisubstituted, identically or differently, phenylcarbonyl, phenylsulfonyl, phenylaminocarbonyl or phenylmethylsulfonyl, where as pheny l substituents are in each case 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 in the phenyl moiety in the same or different ways, phenylthiomethylsulfonyl or phenylazo, the phenyl substituents in each of those mentioned in R ¹ to be considered. In addition to the compounds mentioned in the preparation examples, the following substituted hetero-fused imidazoles of the general formula (I) may be mentioned individually:

The entire examples also apply to R ³ = CHF ₂ , R ³ = C ₂ F ₅ , R ³ = C ₃ F ₇ and also the R ² and R ³ variation for each X ¹ to X ³ pattern as in the table specified.

The substituent variations given in the table above can also be given 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

If, for example, pyrimidinoimidazole (1) and chloromethyl ethyl ester are used as starting compounds, the course of the reaction of the process according to the invention can be represented by the following reaction scheme:

Formula (II) provides a general definition of the heteroanellated imidazoles required to carry 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 can be obtained 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, aralkylsufonic acid esters, alkylsulfonic acid esters, alkylcarbonyloxy or arylcarbonyloxy, particularly preferably for chlorine, bromine, iodine, C _{1 -8} -alkylsulfonic acid esters, tolylsulfonic acid esters, phenylsulfonic acid esters, C _1-8 -alkylcarb- onyloxy, 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 the formula (III) are known or can be obtained analogously to known processes (cf., for example, DE 20 40 175; DE 21 19 518; Synthesis 1973. 703).

Inert organic solvents are suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate or bases such as pyridine or organic acids such as formic acid or acetic acid. The process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal 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 hydroxide , Ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium arbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, lithium-organic compounds, such as n-butyllithium and tertiary amines, such as trimethylamine, triethylamine, tributylamine, di-isopropyl-ethyluanidine, tetram , N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

In cases where A in formula (III) represents an alcohol, alkanoyloxy or alkoxy group, organic or inorganic acids, such as, for example, sulfuric acid, hydrochloric acid, p-toluenesulfonic acid, perfluorobutanesulfonic acid or strongly acidic ion exchangers, are also suitable as reaction auxiliaries. 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 -alkylammonium bromide, dibenzyl-dimethyl- ₁₂ -ammonium / ammonium-bromide _14- alkylbenzylammonium 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) amine.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -70 ° C and + 200 ° C, preferably at temperatures between 0 ° C and 130 ° C.

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

To carry out the process according to the invention, 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of compound of the formula (III) and, if appropriate, 0.01 to 5 mol, are generally employed per mol of 1-hetero-fused imidazole of the formula (II), 0 mol, preferably 1.0 to 3.0 mol, of reaction auxiliaries.

In a special embodiment, it is also possible to first of all the 1H-heteroanellated imidazoles of the formula (II) in a preceding reaction step using customary silylation processes, for example using hexamethyldisilazane or trimethylsilyl chloride, optionally in the presence of a suitable catalyst, such as sulfuric acid, trifluoroacetic acid, ammonium sulfate, imidazole or to silylate saccharin at temperatures between -20 ° C and + 50 ° C and to convert the hetero-fused 1-trimethylsilylimidazoles thus obtainable in a subsequent second step with alkylating agents of the formula (II) according to the process of the invention put. In this case, it is advantageous to add tin tetrachloride as catalyst for the alkylation reaction (cf., for example, Chem. Heterocycl. Comp. USSR 24, 514 [1988]).

The reaction is carried out, worked up and isolated by known processes (see also the preparation examples).

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

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

The active compounds according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcelüo scaber.

From the order of the Diplopoda e.g. Blaniulus guttulatus

From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla e.g. Scutigerella immaculata.

From the order of the Thysanura e.g. Lepisma saccharina.

From the order of the Collembola e.g. Onychiurus armatus.

From the order of the Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera e.g. Forficula auricularia.

From the order of the Isoptera, for example Reticulitermes spp .. From the order of the Anoplura, for example Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp ..

From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.

From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasis, spp. Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplocapsia n. , Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia pbdana, Capua reticulana, Choristoneura fümiferana, Clysia ambiguella, Homona magnidana, Homona magnidanana.

From the order of the Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodalazaisyo spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethus aeneuc., Ptin., Ptin psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis, Costelytra zealandica.

From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..

From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.

From the order of the Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..

The active compounds according to the invention are notable for high insecticidal and acaricidal activity. They can be used with particularly good success for combating plant-damaging insects, such as, for example, against the larvae of the horseradish leaf beetle (Phaedon cochleariae) or against the larvae of the green leafhopper (Nephotettix cincticeps) against the caterpillars of the cockroach Plutella maculipennis. The active compounds according to the invention can furthermore be used as defoliants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places, where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can e.g. are used in the following plants: dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirs Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea. Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scaspalirum, Scarum , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

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

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

Depending on the concentration, the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forests, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops. The active compounds according to the invention can be used particularly successfully to control monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops such as, for example, wheat, corn or soybeans.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols, 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, such as dimethylformamide or dimethyl sulfoxide, and water.

Solid carrier materials are suitable: for example ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates; Solid carriers for granules are possible: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as poly oxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; The following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes 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 of active compound, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids, such as dichloropicolinic acid, dicamba or picloram; Aryloxyalkanoic acids such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofopethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as oryzalin, pendimethalin and trifluralin; Diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas such as chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, such as imazethapyr, Imazamethabenz, imazapyr and imazaquin; Nitriles such as bromoxynil, dichlobenil and ioxynil; Oxyacetamides such as mefenacet; Sulfonylureas, such as, for example, amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines such as atrazine, cyanazine, simazin, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin; Others, such as, for example, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralide, difenzoquat, dithiopyr, ethofümesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible. The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying; Spray, sprinkle. The active compounds according to the invention can be applied both before and after emergence of the plants.

They can also be worked into the soil before sowing.

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

When used as insecticides, the active compounds according to the invention can also be used in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc. The active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists when used as insecticides. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active. The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active ingredient concentration of the use forms can be from 0.0000001 to 95 percent by weight of active ingredient, preferably between 0.0001 and 1 percent by weight.

When used as insecticides, they are used in a customary manner which is adapted to the use forms.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Manufacturing examples

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 (eluent: dichloromethane).

2.40 g (74% of theory) of l-ethoxymethyl-2-trifluoromethyl-bromopyridinoimidazole 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-). The isomers can be separated from one another by recrystallization with an ether / petroleum ether mixture.

The compounds listed in the table below are obtained analogously. * The ¹ H-NMR ¹ spectra were recorded in deuterochloroform (CDCI ₃ ) with tetramethylsilane (TMS) as the internal standard. The chemical shift is given as a δ value in ppm; in all cases the shift of the N-CH ₂ R ¹ R ² protons is given.

Example A:

Pre-em eren ce test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is reduced in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control)

100% = total annihilation

In this test, the compounds according to the preparation examples (1) and (6) show a clear superiority in effectiveness with comparable crop selectivity, for example in wheat crops at a rate of application of 1,000 g per hectare compared to weeds such as Chenopodiurh (95-100%), galinsoga ( 95-100%), Matricaria (90-95%), Portulaca (100%), Stellaria (100%) and Viola (90-95%), whereby wheat is not harmed (0%).

Example B:

Post emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level. Concentration.

Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. After three weeks, the degree of damage to the plants is reduced in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control)

100% = total annihilation

The compounds according to the preparation examples (1), (6) and (12) show a clear superiority in effectiveness as well as in crop selectivity in this test, for example in wheat crops at an application rate of 250 g per hectare compared to weeds such as Datura (90-100 %), Helianthus (90-100%), Portulaca (90-100%), Sinapis (100%) and Solanum (80-100%), whereby wheat is not harmed (0%).

Example C: Phaedon larval test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, a part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by dipping into the active substance preparation of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed. In this test, for example, the compound of preparation example (1) shows a degree of killing of 100% after 7 days with an active compound concentration of 0.1%.

Example D:

Plutella test

Solvent: 5 parts by weight of dimethylformamide

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella maculipennis) while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed. In this test, for example, the compound of preparation example (1) shows a degree of killing of 100% after 7 days with an active compound concentration of 0.1%.

Example E:

Nephotettix test

Solvent: 7 parts by weight of dimethylformamide

Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with larvae of the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.

After the desired time, the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed. In this test, for example, the following compounds of preparation examples (1) and (10) show degrees of kill up to 100% after 6 days at an active compound concentration of 0.1%.

Claims

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, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero) aryl, (hetero) arylcarbonyl, (hetero) - aryloxycarbonyl, (hetero) arylcarbonyloxy or (hetero) arylaminocarbonylaminocarbonyloxy, or R ^{3 represents} cyano, halogen, straight-chain or branched in each case optionally unsubstituted or substituted radical of the series alkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkynyloxy, dialkoxyphosphonyl, amino, aminocarbonyl or aryl, A ¹ , A ² , A ³ and A ^{4 represents} each optionally N (nitrogen), N-CHR ¹ R ² or

CX are 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

X ¹ , X ² and X ³ each independently of one another for hydrogen, halogen, cyano, nitro or for a straight-chain or branched, in each case 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, where X is at least one, but at least one of the substituents X, but at least one of the substituents X ¹ , but at least one of the substituents X, ¹ , but at least one of the substituents X, ¹ , but at least one of the substituents X, ² , but at least one of the X, represents at least one of the substituents X, but at least one of the X. 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 amino nocarbonyl or for 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 is} 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 represents phenyl which is optionally mono- or polysubstituted by identical or different substituents, 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 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 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 with 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 differentiated by halogen and / or straight-chain or branched

Alkyl with 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 phenyl, R ² for hydroxyl, cyano or for a straight-chain or branched and in each case optionally single or multiple, identical or differently substituted radicals from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl each having up to 8 carbon atoms in the individual alkyl or alkenyl or alkynyl parts, the substituents being in question come:

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 - stands, whereby as

Aryl or heteroaryl substituents which are suitable for R ¹ , R ² furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, where the following are suitable as substituents:

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, each optionally mono- or disubstituted, identically or differently, carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each having 3 to 8 carbon atoms, substituted by straight-chain or branched alkyl having 1 to 8 carbon atoms Cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthiocarbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl each having 1 to 8 carbon atoms in the individual straight-chain or branched alkyl parts, in each case doubly linked and ring-closed alkanediylcarbonyl or alkanediyloxyyl atoms, arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl each having 6 to 10 carbon atoms in the aryl part and mono- or polysubstituted in the aryl part in the aryl part d 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, substituted aryl, arylcarbonyl or aryloxycarbonyl, each with 6 to 10 carbon atoms in the aryl part, where the aryl substituents mentioned in R ¹ are possible, R ² also represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which is mono- or polysubstituted in the same or different ways, 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 being in each case optionally mono- or polysubstituted, identical or differently substituted heteroaryl, heteroarylcarbonyl, heteroaryloxy carbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy each having 2 to 9 carbon atoms and 1 to 5 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - is in the heteroaryl part, the heteroaryl substituents in each case being the aryl substituents mentioned in R ¹ ,

R ³ for cyano, fluorine, chlorine, bromine, iodine or for a straight-chain or branched, each optionally unsubstituted or substituted radical of 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 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 ³ furthermore represents amino or aminocarbonyl which may be mono- or disubstituted in the same way or differently, where the following are suitable as substituents:

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, alkylthiocarbonyl, alkoxythiocarbonyl or alkylthio-1-thiocarbonyl straight chain or branched Alkyl parts, in each case doubly 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, mono- or polysubstituted in the arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl group, each having 6 to 10 carbon atoms in the aryl part and 1 up 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, 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 for R ¹ , A ¹ , A ² , A ³ and A ⁴ for each optionally N (nitrogen), N-CHR ¹ R ² or

CX are 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 for one nitrogen atom and CX ¹ and CX ² for 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 (R ³ ) and

X ¹ , X ² , X ³ each independently of one another for hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, for in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 1 to

8 carbon atoms, for cycloalkyl having 3 to 8 carbon atoms, for each 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, the same or differently substituted and linked 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, also linked Hydroxycarbonyl, for each straight-chain or branched alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl part or for each optionally mono- or polysubstituted, identically or differently substituted amino or aminocarbonyl, the amino substituents in question in each case come: 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 aryl carbonyl, arylsulfonyl, arylaminocarbonyl or arylmethylsulfonyl each having 6 to 10 carbon atoms in the aryl part, in each case optionally mono- or polysubstituted by identical or different substituents, 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 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 , where the aryl substituents in each case are those mentioned in R ¹ and where at least one of the substituents X ¹ , X ² or X ^{3 is} in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 up to 13 identical or different halogen atoms, for straight-chain or branched alkylsulfonyl with 1 to 6

Carbon atoms or for optionally single or multiple, the same or differently substituted and linked 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, also linked Hydroxycarbonyl, represents in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl part or for in each case optionally mono- or polysubstituted, identically or differently substituted amino or aminocarbonyl, the amino substituents in question in each case come: 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 i m each aryl part, optionally mono- or polysubstituted, the same 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 represent aryl, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo, each having 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, where aryl substituents in each case are those mentioned in R ¹ .

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 phenyl is monosubstituted to trisubstituted by identical or different substituents, 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 having 1 to 4 carbon atoms, each straight-chain or branched

Haloalkyl, haloalkoxy, 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 alkoximinoalkyl each having 1 to 4 carbon atoms in each

Alkyl parts, optionally monosubstituted to sixfold, 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 and doubly linked dioxyalkylene 1 to 4 carbon atoms or optionally single to five times, identical 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 halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in which

Halogen in each case represents fluorine, chlorine, bromine, iodine, R ^{2 represents} hydroxyl, cyano or a straight-chain or branched, in each case optionally up to five times, identically or differently, fluorine, chlorine, bromine or iodine-substituted radicals from 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 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 Substance atoms in the individual alkyl or alkenyl or alkynyl parts, the substituents being in each case: 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 -, where aryl or heteroaryl substituents which are mentioned in R ¹ are possible, R ² also each optionally mono- or disubstituted, identically or differently substituted amino or Aminocarbonyl stands as

Substituents are possible:

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, 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, alkylthiocarbonyl, alkoxy-thiocarbonyl or alkylthio-1-geriocarbonyl or 1-benzo-1-ythi-carbonyl branched alkyl parts, each double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each having 2 to 5 carbon atoms in the alkanediyl part, in each case optionally in the aryl part, one to three times, the same or different Substituted arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl, each having 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, monosubstituted to triple, identically or differently substituted, aryl, arylcarbonyl or aryloxycarbonyl each having 6 or 10 carbon atoms in the Aryl part, the aryl substituents in each case being those mentioned in R ¹ ,

R ² also for aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy each having 6 or

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, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy each having from 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms, in particular nitrogen, oxygen and / or sulfur, in each case monosubstituted to pentasubstituted by identical or different substitution is in the heteroaryl part, the heteroaryl substituents in each case being the aryl substituents mentioned for R ¹ , R ³ for cyano, fluorine, chlorine, bromine, iodine or for a straight-chain or branched, optionally one to five times, identical or different by fluorine, chlorine, Bromine and / or iodine-substituted radicals from 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 each optionally up to three times , the same or r differently substituted cycloalkyl, 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, the substituents in question come:

Fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy with 1 to

6 carbon atoms or, in each case, optionally up 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 aryl or heteroaryl substituents are those mentioned in R ¹ ,

R ³ also stands for amino or aminocarbonyl which is optionally mono- or disubstituted, identically or differently, where as

Substituents are possible:

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, alkylthiocarbonyl, alkoxy-thiocarbonyl or alkylthio-1-geriocarbonyl or 1-benzo-1-ythi-carbonyl branched alkyl parts, each double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each having 2 to 5 carbon atoms in the alkanediyl part, in each case optionally in the aryl part, one to three times, the same or different substituted arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl each having 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 monosubstituted to triple, identically or differently substituted aryl, arylcarbonyl or

Aryloxycarbonyl each having 6 or 10 carbon atoms in the aryl part, the aryl substituents in each case those mentioned in R ^{1 being} suitable,

R ³ also represents aryl which is optionally monosubstituted to pentasubstituted by identical or different substituents, 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'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 at a nitrogen atom 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 to 7 carbon atoms, for each 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 double to optionally substituted by up to six times, identical or different, 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

Dioxyalkylenes with 1 to 4 carbon atoms also represent hydroxycarbonyl, for each 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 optionally mono- or disubstituted, identically or differently substituted Amino or aminocarbonyl, where the amino substituents are in each case: straight-chain or branched alkyl with 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 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 in which at least one of the substituents X ¹ , X ² , X ³ for straight-chain or branched haloalkyl haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 are the same or different halogen atoms, for straight-chain or branched alkylsulfonyl with 1 to 4 carbon atoms or for optionally up to six times, identical or different by halogen and / or straight-chain or branched alkyl with 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 coals Substance atoms and 1 to 9 identical or different halogen atoms substituted, double-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 represents in each case monosubstituted or disubstituted, identically or differently substituted amino or aminocarbonyl, the amino substituents in each case being suitable: 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 with 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, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulfonyl or arylazo each having 6 or 10 carbon atoms in the aryl part, such as phenyl or, in each case in the aryl part, monosubstituted to pentasubstituted, identically or differently Stand naphthyl, being as

Aryl substituents are 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 alkyl series,

Alkoxy with in each case 1 to 4 carbon atoms or for phenyl which is mono- or disubstituted in the same way or differently, where the following may be used as substituents:

Fluorine, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 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 halo Genetically atom-substituted, double-linked dioxyalkylene with 1 to 3 carbon atoms or optionally single to triple, 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 the same or different halogen atoms substituted phenyl, where halogen in each case represents fluorine, chlorine, bromine,

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 a radical of the series alkyl, alkenyl,

Alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, 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, 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, suitable phenyl substituents being those mentioned for R ¹ ,

R ² also stands for amino or aminocarbonyl which is optionally mono- or disubstituted, identically or differently, where as

Substituents are possible:

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 carbamoyl, thiocarbamoyl or sulfamoyl, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl part, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthiocarbonyl, substituted by straight-chain or branched alkyl having 1 to 4 carbon atoms

Alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each having 1 to 4 carbon atoms in the individual straight-chain or branched alkyl parts, each having double-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, monosubstituted or disubstituted, identically or differently 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 monosubstituted or disubstituted, identically or differently substituted phenyl, phenylcarbonyl or phenyloxycarbonyl, the phenyl substituents in each case being those mentioned in R ¹ ,

R ² furthermore represents phenyl, phenylcarbonyl, phenyloxycarbonyl, phenylcarbonyloxy or phenylaminocarbonylaminocarbonyloxy which may be monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents in each case being those mentioned in R ¹ ,

R ² also represents in each case monosubstituted to trisubstituted, identically or differently, heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each having 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - in the hetero atom , 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 branched, optionally single to triple the same or different radical substituted by fluorine, chlorine and / or bromine in the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy 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, alkylcarbonyloxy or dialkoxyphosphoryl each having up to 4 carbon atoms in the individual alkyl or alkenyl or alkynyl parts, where as Substituents are in each case suitable: straight-chain or branched alkoxy having 1 to 3 carbon atoms or optionally mono- or disubstituted, identically or differently substituted phenyl, where phenyl substituents are those mentioned for R ¹ , R ³ also for each optionally single or double, identical or different substituted amino o the aminocarbonyl is available, the following being suitable as substituents:

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 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, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each with 1 to 4 carbon atoms in the individual straight-chain or branched alkyl parts, in each case double-linked and ring-closed alkanediylcarbonyl or alkanediyloxycarbonyl, each with 2 to 4 carbon atoms in the AJ each optionally in the phenyl part simply or phenylalkyl, phenylalkylcarbonyl or phenylalkyloxycarbonyl which are substituted twice, identically or differently, each having 1 to 4 carbon atoms in the straight-chain or branched alkyl part or in each case optionally in the phenyl part, singly or twice, identical or differently substituted phenyl, phenylcarbonyl or phenyloxycarbonyl, where the phenyl substituents in each case are those in R ¹ mentioned,

A ¹ , A ² , A ³ and A ⁴ each optionally represent N (nitrogen), N-CH R 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 at 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 mono- to tetrasubstituted, identically or differently, 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 Dioxyalkylenes with 1 to 3 carbon atoms also represent hydroxycarbonyl, 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 cycloalkyl part or for each optionally single or double, identical or differently substituted amino or aminocarbonyl, the amino substituents in each case being suitable: 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 monosubstituted to trisubstituted, identically or differently, 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 part in one to three times, identically or differently, 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 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, for straight-chain or branched alkylsulfonyl having 1 to 3 carbon atoms or for optionally single to fourfold, 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 same n or different halogen atoms substituted, double linked Dioxyalkylene with 1 to 3 carbon atoms also represents hydroxycarbonyl, each straight-chain or branched alkylcarbonyl or alkoxycarbonyl each having 1 to 3 carbon atoms in the alkyl part, for cycloalkyloxycarbonyl having 3, 5 or 6 carbon atoms in the cycloalkyl part or for each optionally single or double, identical or differently substituted amino or aminocarbonyl, the amino substituents being 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

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 in the phenyl moiety in the same or different ways, phenylthiomethylsulfonyl or phenylazo, the phenyl substituents in each of those mentioned in R ¹ to be considered.

5. Process for the preparation of new, substituted, fused imidazoles of the general formula (I)

R ^{2 is} hydroxyl, cyano or a straight-chain or branched, optionally unsubstituted or substituted radical of the series

Alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero) aryl, (hetero) arylcarbonyl, (hetero) aryloxycarbonyl, (hetero) arylcarbonyloxycarbonyloxy (hetero) arylcarbonyloxycarbonyl stands,

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 for each optionally N (nitrogen), N-CHR ¹ R ² or

A ³ or A ⁴ stand for N-CHR ¹ R ² , the imidazole ring is only monosubstituted, in which

X ¹ , X ² and X ³ each independently of one another for hydrogen, halogen, cyano, nitro or for a straight-chain or branched, in each case optionally unsubstituted or substituted radical of the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, for hydroxycarbonyl, alkylcarbonyl , Alkoxycarbonyl, cycloalkyloxy carbonyl, represent in each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, 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 optionally substituted amino or aminocarbonyl or for optionally substituted aryl,

Arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl, characterized in that 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. A method for controlling unwanted plants, characterized in that substituted, hetero-fused imidazoles of the general formula (I) according to Claims 1 to 5 are allowed to act on plants and / or their habitat.

8. Use of substituted, hetero-fused imidazoles of the general formula (I) according to Claims 1 to 5 for combating undesired plants.

9. A process for the preparation of herbicidal and insecticidal agents, characterized in that substituted, heteroanellated imidazoles of the general formula (I) according to Claims 1 to 5 are mixed with extenders and / or surface-active substances.

10. Use of substituted heteroanellated imidazoles of the general formula (I) according to Claims 1 to 5 for combating animal pests.