CA2158996A1 - Substituted heteroannulated imidazoles and their use as herbicides - Google Patents

Abstract

New substituted heteroannulated imida-zoles having general formula (I), in which R1, R2. R3, A1. A2. A3 and A4 have the meanings given in the description, are disclosed, as well as a process for preparing the same and their use as herbicides.

Description

~- 2158996 BAYE~AKIIENGESElI~ T 51368 Lcve-l~r K~mPln7P~
Pa~er~e K~mem WA/HB
FILE, PtN 1~1 THE3 ~
T~TRANSLATlON

SUBSTITUTED HETER~FUSFn I~nAZOLES AND T~FTR USE AS
S HERBICIDES

Ihe invention relates to new substituted hetero-fused imidazoles, to a process for their p~ ion, and to their use as herbicides.

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

10 Ihere have now been found new substituted hetero-fused imidazoles of the general formula (I) 3 '~ N
\~R3 (I) CH--R

in which R' represents hydrogen or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkoxy lS and aryl, R2 represents hydroxyl, cyano or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of Le A 29 565 alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl,(hetero)arylcarbonyloxy and (hetero)arylaminocarbonylamino-carbonyloxy, 5 R3 represents cyano, halogen or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series concicting of alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkinyloxy, amino, aminocarbonyl and aryl, A~, A2, A3 and A4 in each case represent N(nitrogen), N-CHR'R2 or CX, the hetero-fused ring having at least one, but not more than two, nitrogen atoms .simlll~n~ously and all positional isomers being possible, so that CXI, CX2, CX3 exist in the case of one nitrogen atom and CX' and CX2 exist in the case of two nitrogen atoms, and, when either Al, A2, A3 or A4 represent N-CHR'R2, the imidazole ring exists only in monosubstituted form I S (R3), where Xl, x2 and X3 in each case independently of one another represent hydrogen, halogen, cyano, nitro or a straight-chain or branched, in each case optionally unsubstituted or s-lb.sti~lt~ radical from the series concicting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl and cycloalkyl, or represents hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, or represents in each case optionally s~bstilllt~l amino or aminocarbonyl, or represents in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substitutents Xl, x2 or X3 represents halog~no~lkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkylsulphonyl, or represent~s LeA29 565 -2-optionally substit~lt~ fused dioxyalkylene, or represents hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, or represents in each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, S arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl .

Depending on the nature and number of sl~bstit~Jt~ntc~ the compounds of the formula (I) can, if a~uro~)l;ate~ exist as geometric and/or optical isomers or regioisomers or variously composed isomer mixtures of these, but also in the form of positional isomers, for example in the following variations:

N ~C~R
N~--N x ~N X ~R
~3R R X ~-R X~ C9R-R

X~
~R-R

or, for example, the following variations are also possible:

LeA29 565 - 3 -21~996 X CHRR X

~R~ ~N X ~N
1 2 ~ I
CHR R X X

Furth~-more, it has been found that the new substituted hetero-fused imidazoles of the general formula (I) 3 'J~ N
3~ R3 A~AI ~ , R

in which R' represents hydrogen or a straight-chain or branched, in each case optionally S unsubstituted or substituted, radical from the series consisting of alkyl, alkoxy and aryl, R2 represents hydroxyl, cyano or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series c )n~i~ting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)arylcarbonyl, (hetero)a~yloxycarbonyl,(hetero)arylcarbonyloxy and (hetero)arylaminocarbonylaminocarbonyloxy, R3 represents cyano, halogen or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkinyloxy, amino, amin()c~rbonyl and aryl, A', A2, A3 and A4 in each case represent N(nitrogen), N-CHRIR2 or CX the LeA29 565 -4-``` ~158996 - heterofused ring having at least one, but not more than two, nitrogen atoms ~im~llt~n~ously and all positional isomers being possible, so that CX', CX2, CX3 exist in the case of one nitrogen atom and CX' and CX2 exist in the case of two nitrogen atoms, and, when either A', A2, A3 or A4 represent N-CHR'R2, the imidazole ring exists only in monosukstit~ 1 form (R3), where, X', x2 and X3 in each case indep~n-l~ntly of one another represent hydrogen, halogen, cyano, nitro or a straight-chain or branched, in each case optionally lm~l~bstitutedorsubstitte~lradicalfromtheseriescon~i~tingofalkyl~alkoxy~
alkylthio, alkyl~l-lphinyl, alkyl~lllphonyl and cycloalkyl, or represents hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, or represents in each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substituents X', x2 or X3 represents halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkylsulphonyl, or represents optionally substituted fused dioxyalkylene, or represents hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, or represents in each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, 25 are obtained when a) lH-substituted hetero-fused imidazoles of the formula (II) LeA29 565 - 5 -215~996 "

~XN
~ A H
in which Al, A2, A3, A4 and R3 have the abovementioned m~nin~

are reacted with compounds of the formula (~I) R
~CH ~

in which M represents a suitable leaving group and R' and R2 have the abovementioned m~nin~, if ap,ul~l;ate in the presence of a diluent and if apl~ro~l;ate in the presence of a reaction auxiliary.

Finally, it has been found that the new substituted hetero-fused imidazoles of the 10 general formula (1) have good herbicidal activity.

Surprisingly, the new substituted hetero-fused imidazoles of the general formula (I) according to the invention show a considerable herbicidal activity against problem weeds combined with a similarly good tolerance by important crop plants.

Formula (I) provides a general definition of the substituted hetero-fused imidazoles 15 according to the invention. Preferred compounds of the formula (I) are those in which LeA29 565 -6-- 21S~39~6 R' represents hydrogen or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series con~i~ting of alkyl and alkoxy, each of which has 1 to 8 carbon atoms, or represents phenyl which is optionally monosubstituted or polysubstituted by identical or dilrelcl~t S substit~lent~, suitable substituents being:

halogen, cyano, nitro in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkyl~ phinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halo~en~lkoxy, halogenoalky~thio, halo~no~lkyl-sulphinyl or halogeno~lkylsulphonyl each of whichhas 1 to6carbonatomsand 1 to 13 identicalordi~elclllhalogenatoms, in each case straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alko~imino~lkyl each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or divalent dioxyalkylene having 1 to 5 carbon atoms which is optionally monosllbsti~ltel or polysubstituted by identical or di~lcll~ substit~l~nt~ from the series con~icting of halogen, straight-chain or branched alkyl having 1 to 6 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or difr~cll~
halogen atoms, or phenyl which is optionally monosubstituted or polysubstituted by identical or di~el~nl substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 6 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, R2 represents hydroxyl, cyano or a straight-chain or branched radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each of which has up to 8 carbon atoms in the individual alkyl or alkenyl or alkinyl moieties and each of these radicals optionally beingmonosubstituted or polysubstituted by identical or di~lclll substituents, suitable substituents in each case being:

fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 Le A 29 565 - 7 --` 21S8~9~
- to 8 carbon atoms, or aryl having 6 to 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 5 hetero atoms (in particular nitrogen, oxygen and/or sulphur), these aryl or heteroaryl substituents in each case optionally being monosubstituted or polysubstituted by identical or di~ lt substituents and suitable aryl or heteroaryl substit~1~nt~ being those mentioned in the case of R', R2 furth~rmore represents amino or aminocarbonyl, each of which is optionally monosllkstiblt~i or ~ 1kstib te1 by id~ntic~l or di~lelll substituentsl suitablesubstituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms, straight-chain or branched alkyl.~l-lphonyl having 1 to 8 carbon atoms, c~l,~lluyl, thioc~b~lloyl or sl-lrh~moyl, each of which is monosl-bstit~1t~1 or disubstituted by identicalor di~elt;lll straight-chain or branched alkyl substituents having 1 to 8 carbonatoms, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxyc~bûllyl, each of which has 3 to 8 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenyl-carbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 8 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or ~lk~n~Aiyloxycarbonyl~ each of which has 2 to 6 carbon atoms in the alkanediyl moiety, arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or ~ el~lll substituents, or aryl, arylcarbonyl or aryloxy-carbonyl, each of which has 6 to 10 carbon atorns in the aryl moiety and each of which is optionally monosllhs1ituted or polysubstituted in the aryl moiety byidentical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R', 30 R2 furthermore represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or LeA29 565 - 8-21~839~

arylaminocarbonylaminocarbonyloxy, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosll~stituted or poly-s~lbstit~te:l by identical or di~e~ l sllbstihl~t~, suitable aryl substituents in each case being those mentioned in the case of R', 5 R2 furthermore represents heteroaryl, heteroarylcarbonyl, heteroaryloxyc~l~llyl, heteroarylcarbonyloxy or heteroarylAminr~,Arbonylaminocarbonyloxy, each of which has 2 to 9 carbon atoms and 1 to 5 identical or different hetero atoms (inparticular nitrogen, oxygen and~or sulphur) in the heteroaryl moiety and each ofwhich is optionally monosllhstihlte~ or polysubstih~ 1 by identical or di~e~
substitl-~nt~, suitable heteroaryl substituents in each case being the aryl substi-tuents mentioned in the case of R', R3 represents cyano, fluorine, chlorine, bromine, iodine or a straight-chain or brAn~1 in each case optionally unsubstituted or substil~1 radical from the series co~ ting of cycloalkyl, alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkenyloxy, each of which has up to 8 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties, suitable ~ubstit~nt~ in each case being: fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 8 carbon atoms, or aryl having 6 to 10 carbon atorns or heteroaryl having 2 to 9 carbon atoms and l to 5 hetero atoms (in particular nitrogen, oxygen and!or sulphur), each of these aryl or heteroaryl radicals optionally being monosllbstinlle1 or polysllhstitllte~
by identical or different substituents and suitable aryl or heteroaryl substituents being those mentioned in the case of R', R3 furthermore represents amino or arninocarbonyl, each of which is optionally monosubstituted or ~iicllbstituted by identical or di~lcllt subs~ nt~, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, carbarnoyl, thiocarbamoyl Le A 29 565 - 9 -21~99~

or sulpl~lloyl, each of which is monosubstituted or ~ hstil~lte1 by identical or di~elclll straight-chain or branched alkyl substit~nt~ having 1 to 8 carbon atoms, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 8 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, S alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 8 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alk~tlefliylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkanediyl moiety, arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosllbstituted or polysllkstitllted in the aryl moiety by identical or di~elcl,l s~lbstit~l~nt~, or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosllkstituted or polys 1bstit:~lte~1 in the aryl moiety by identical or di~elclll substituents, suitable aryl substituents in each case being those mentioned in the case of R', i R3 fur~ermore represents aryl having in each case 6 to 10 carbon atoms in the aryl moiety which is in each case optionally monosllhstit~ltel or polysubstituted by identical or di~elcllL substituents, suitable aryl substituents in each case being those mentioned in the case of R', Al, A2, A3 and A4 in each case represent N(nitrogen), N-CHR~R2 or CX the hetero-fused ring having at least one, but not more than two, nitrogen atoms simultaneously and all positional isomers being possible, so that CX', CX2, CX3 exist in the case of one nitrogen atom and CXI and CX2 exist in the case of two nitrogen atoms, and, when either A', A2, A3 or A4 represent N-CHR'R2, the imidazole ring exists only in monosubstituted form (R ), and LeA29 565 -10-` ` 215~996 . X~, x2 and X3 in each case independently of one another represent hydrogen, fluorine, chlorine, b~ ine, iodine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylcl~lrhinyl or alkylsulphonyl, each of which has 1to 8 carbon atorns, cycloalkyl having 3 to 8 carbon atomc, in each cace straight-S chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio,halogenoalkyl.cl-lphinyl, halo~enoalkyl~l-lrhonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or di~re~c"l halogen atoms, or divalent dioxyalkylene having 1 to 5 carbon atoms which is optionally mc nos~lbstituted or polysl-bs1it~ by identical or di~elc"l substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogeno~lkyl having 1 to 4 carbon atoms and 1 to 9 identical or .li~ halogen atoms, fur~h~more represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or polysubstituted by identical or dirre,c"l substitll~ntc, suitable amino substit~.q.nt.
in each case being:

in each case straight-chain or branched alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or arylcarbonyl, aryl.clllrhonyl, arylaminocarbonyl or arylmethylsulphonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosllkstituted or polysubstituted in the aryl moiety by identical or di~e,cl,l substit~l~nt~, suitable aryl substituents in each case being those mentioned in the case of Rl;

X', x2 and X3 furthermore represent aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethyl-sulphonyl or arylazo, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each Le A 29 565 215~996 - case being those mentioned in the case of R', and where at least one of the substituents X', x2 or X3 represents in each case straight-chain or branched halo~ lkyl, halogenoalkoxy, halogenoalkylthio, halogeno-alkyl~l-lphinyl, halo~eno~lkylsulphonyl, each of which has 1 to 6 S carbon atoms and 1 to 13 identical or dilr~ 1 halogen atoms, or represents straight-chain or branched alkyl~l-lphonyl having 1 to 6 carbon atoms, or divalent dioxyalkylene having 1 to 5 carbon atoms which is optionally monosubstituted or polys~-bstit~e~l by identical or dirr~lc~ll substit~l~nt~ from the series con~i~tin~ of halogen, straight-chain or branched alkyl having 1 to 4carbon atorns and straight-chain or branched halo~en-)~lkyl having 1 to 4 carbonatorns and 1 to 9 i~l~ntir~l or di~lcll~ halogen atorns, fLulh~ ore represents hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl moiety, or arnino or aminocarbonyl, each of which is optionally m-)nosllbstitued or polysubstituted by identical or di~ l.l substituents, suitable amino substituents in each case being:

in each case straight-chain or branched alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms"
alkoxyalkyl or alkylcarbonyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or arylcarbonyl, ar,vlsulphonyl, arylaminocarbonyl orarylmethylsulphonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different substituents in the aryl moiety, suitable aryl substituents in eachcase being those mentioned in the case of R', X', x2 and X3 furthermore represent aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being LeA29 565 . -12-21S~9~
those mentioned in the case of R'.

Particularly pl~r~lled cornpounds of the formula (I) are those in which Rl represents hydrogen, or a straight-chain or branched radical from the series consisting of alkyl and alkoxy, each of which has 1 to 6 carbon atorns and each S of which is uns~lkstihlte~l or substituted, or represents phenyl which is optionally monosubstituted to trisubstituted by identical or diLrelcl~l substil~nt~, suitable substituents being:

fluorine, chlorine, bromine, iodine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkyl.clllphinyl or alkyl~lllphonyl, each of which has 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkyl~lllphonyl, each of which has 1 to 4 carbon atoms and 1 to 9 identical or diLr~ll halogen atoms, in each case straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxyc~l,ullyl or alkoximinoalkyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally monosubstituted to hexasubstituted by identical or diLr~ substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or phenyl which is optionally monosubstituted to pentasubstituted by identical or dirr~ l substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or di~e~ halogen atoms, halogen in each case representing fluorine, chlorine, bromine or iodine, R2 represents hydroxyl, cyano, or a straight-chain or branched radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and dialkoxyphosphonyl, each of which has up to 6 carbon atoms in the individual Le A 29 565 - 13 -2158~96 alkyl, alkenyl or alkinyl moieties and each of which is optionally monosllhstitute~ to p~nt~c~lbstituted by identical or di~ t substituents from the series concicting of fluorine, chlorine, bromine and iodine, or represents alkyl, alkenyl or alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each of which has up to 6 carbon atoms in the individual alkyl, alkenyl or allcinyl moieties and each of which is optionally monosllkstitllte~:l to trisubstituted by identical or di~lclll substit~ntc, suitable substituents in each case being:

straight-chain or branched alkoxy having 1 to 6 carbon atoms, or aryl having 6 or 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 4 hetero atoms (in particular nitrogen, oxygen and/or sulphur), each of these aryl or heteroaryl radicals optionally being monosubstituted to trisubstituted by identical or di~ l substit~lentc and suitable aryl or heteroaryl substituents being those mentioned in the case of R', 15 R2 furthermore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or di~le,ll sllbstitll~ntc, suitable sub~ti1llPntc in each case being:

formyl, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 6 carbon atoms, carbamoyl, thiocarbamoyl or sulphamoyl, each of which is optionally monosubstituted or disubstituted by identical or di~el~llL straight-chain or branched alkyl substituents having 1 to 6 carbon atoms, or cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 6 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 5 carbon atoms in the alkanediyl moiety, arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl, each of which has 6 or 10 carbon LeA29 565 -14-` 21~996 atoms in the aryl moiety and 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosllbstihlte~l to trisubstituted in the aryl moiety by identical or di~.clll substit~l~nt~, or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally mcnosllbstil~lte-1 to trisubstituted in the aryl moiety by identical or di~er~llt sukstihl~t~, suitable aryl substi11lP.nt~
in each case being those mentioned in the case of R', R2 furthermore represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to p~nt~ bstituted by identical or di~ erlt substitl-~nt~, suitable aryl substituents in each case being those mentioned under Rl, R2 furthermore represents heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each of l S which has 2 to 9 carbon atoms and 1 to 4 identical or di~r~lll hetero atoms (in particular nitrogen, oxygen andlor sulphur) in the heteroaryl moiety and each ofwhich is optionally monosubstituted to pt.nt~cubstituted by identical or di~elt;lll substitll-ont~, suitable heteroaryl s~bst~ nt~ in each case being the aryl substituents mentioned in the case of R', 20 R3 represents cyano, fluorine, chlorine, bromine, iodine, or a straight-chain or branched radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl and alkylcarbonyloxy, each of which has up to 6 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and which is optionally m-)nosllbstituted to pentasubstituted by identical or di~lclll substituents from the series consisting of fluorine, chlorine, bromine and iodine, or represents cycloalkyl, alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each of which has up to 6 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted to trisubstituted by identical or di~
LeA29 565 -15 -~ 21~;~996 substit~ent~ suitable substituents in each case being:

fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 6 carbon atoms, or aryl having 6 or 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 4 hetero atoms (in particular nitrogen, oxygen S and/or sulphur), each of these aryl or heteroaryl radicals optionally being monosl-hstih~e~l to trisubstituted by identical or di~ t s~bstit~l~nt~, suitablearyl or heteroaryl substituents being those mentioned in the case of R', R3 f~thermore represents arnino or aminocarbonyl, each of which is optionally monosubstituted or ~ lhstiblt~1 by identical or di~ llt substituents, suitable substitll~nt~ in each case being formyl, s~aight-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 alkyl~ ~lph-~nyl having 1 to 6 carbon atoms, ~lu~~ yl, thiocarbamoyl or slllph~rnoyl, each of which is optionally monos~lkstihlte~l or t~ bsti~lte~1 by identical or diLLelcllt straight-chain or branched alkyl substihl~nt~ having 1 to 6 carbon atoms, or cycloalkyl, cycloalkylcarbonyl, or cycloalkyloxycarbonyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 6 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized ~lk~n~1iylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 5 carbon atoms in the ~lk~n~liyl moiety, or arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted to trisubstituted by identical or difr~l~llt substi~l~ntc in the aryl moiety, or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to trisubstituted inthe aryl moiety by identical or di~el~lll substituents, suitable aryl substituents in each case being those mentioned in the case of R', LeA29 565 -16-~ 21S~996 R3 furthermore represents aryl having in each case 6 or 10 carbon atoms in the aryl moiety which is in each case optionally monosllbstituted to pentasubstituted by identical or di~tlclll substituents, suitable aryl substituents in each case being those mentioned in the case of R', A', A2, A3 and A4 in each case represent N(nitrogen), N-CHR~R2 or CX the hetero-fused ring having at least one, but not more than two, nitrogen atoms siml-lt~n~ously and all positional isomers being possible, so that CX~, CX2, CX3 exist in the case of one nitrogen atom and CX' and CX2 exist in the case of two nitrogen atoms, and, when either A', A2, A3 or A4 represent N-CHR~R2, the imidazole ring exists only in monosl-kstit~ l form (R3), and X', x2 and X3 in each case indep~n-lently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alLylthio, alkyl.~l-lphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 4 carbon atorns and 1 to 9 identical or di~elcll~ halogen atoms, or divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally monosubstituted to hexasubstituted by identical or di~elelll substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthermore represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 4 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 7 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or di~ substituents, suitable amino substituents in each case being:
LeA29 565 -17--` 21~8~
in each case straight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl, arylaminocarbonyl or S arylmethylsulphonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monos -~sti~ ted to p~nt~cllbstit~ l in the arylmoiety by identical or di~lcll~ substitl-~ntc, suitable aryl substit~ntc in eachcase being those mentioned in the case of R';

X', x2 and X3 furthPnnore represent aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthio-methylsulphonyl or arylazo, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosllhstih t~ to p~nt~cuksti~ltecl in the aryl moiety by identical or di~lGII~ substit~l~ntc, suitable aryl substi~u~ntc in each case being those mentioned in the case of R', and where at least one of the substituents X', x2 and X3 represents in each case straight-chain or branched halogeno~lkyl, halog~oalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 4 carbon atoms and 1 to 9 identical or di~lCll~ halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 4 carbon atoms, or divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally m~nosubstituted to hexasubstituted by identical or di~ l substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or ~ l halogen atoms, furthermore represents hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 4 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 7 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable amino substituents in each case being:

~eA29 565 . -18-~ 21S8~96 -in each case straight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atorns, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl arylarninocarbonyl, orS arylmethyl.clllphonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monos~lbstit~ to p~nt~c~lbstilllt~1 in the aryl moiety by identical or dirr~ substitl~ntc, suitable aryl substituents in each case being those mentioned in the case of R';

X', x2 and X3 furthermore represent aryl, arylthio, arylculphinyl, arylsulphonyl, arylclllphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 or 10 carbon atorns in the aryl moiety, such as phenyl or naphthyl, and each of which is optionally mt)nocllhstituted to p~t~C~lbstituted in the aryl moiety by identical or dirr~lellt sllks1ih~ntc, suitable aryl substituents in each case being those mentioned in the case of R'.

Very particularly plcr~ d compounds of the formula (I) are those in which R' represents hydrogen or a straight-chain or branched radical from the series consisting of alkyl and alkoxy, each of which has 1 to 4 carbon atoms and each of which is unsubstituted or substituted, or represents phenyl which is optionally monosubstituted or disubstituted by identical or di~ substituents, suitable substituents being:

fluorine, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 3 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogeno-alkylsulphonyl, each of which has 1 to 3 carbon atoms and 1 to 7 identical or dirrcl~ halogen atoms, in each case straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, divalent dioxyalkylene having 1 to 3 carhon atoms which is optionally monosubstituted to Le A 29 565 - 19 -- 21~8~6 tet~cllbsti~lt~ by identical or di~ substit~t~ from the series cl)n~i~tin~
of halogen, straight-chain or branched alkyl having 1 to 3 carbon atoms and straight-chain or branched halo~no~lkyl having 1 to 3 carbon atoms and 1 to 7 identical or di~ lll halogen atoms, or phenyl which is optionally monosllbstituted to trisubstituted by identical or di~lclll substituents from the series con~ ting of halogen, straight-chain or branched alkyl having 1 to 3 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or dilrel~ halogen atoms, halogen in each case repr~s~.nting fluorine, chlorine or bromine, 10 R2 represents hydroxyl, cyano or a straight-chain or branched radical from the series con.~i~ting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, allcinyloxy, alkylthio, alkylcarbonyl, alkoxyc~L,ol,yl, alkylcarbonyloxy and dialkoxy-phosphonyl, each of which has up to 4 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally ml nosllbstituted totetrasubstituted by identical or di~t;le.ll substit~-~nt~ from the series con.ci~ting of fluorine, chlorine and bromine, or represents alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphoryl, each of which has up to 4 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties, and each of which isoptionally monosubstituted or disubstituted by identical or di~lull substit~l~nt~, suitable substituents in each case being:

straight-chain or branched alkoxy having 1 to 3 carbon atoms or phenyl which is optionally monosubstituted or disubstituted by identical or di~
substituents, suitable phenyl substituents being those mentioned in the case of ~1, R2 fiJrthermore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, Le A 29 565 - 20 -21~8~9~

straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain orbranched alkyl~ llphonyl having 1 to 4 carbon atoms, carbarnoyl, thioc~l,allloylor sulphamoyl, each of which is optionally monosubstituted or disubstituted by identical or difr~lclll straight-chain or branched alkyl substituents having 1 to 4 S carbon atoms, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 4 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or ~lk~n~iyloxycarbonyl, each of which has 2 to 4 carbon atoms in the ~lk~n~liyl moiety, phenylaLkyl, phenylalkylcarbonyl or phenylalkyloxycarbonyl, each of which has 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monc)sllbstituted or ~ bstit~lte~l in the phenyl moiety by identical lS or di~clclll sukstit~l~nt~> or phenyl, phenylcarbonyl or phenyloxycarbonyl, each of which is optionally monos~lbstitllt~l or ~ ukstit~ l in the phenyl moiety by identical or di~lclll substit~-~.ntc, suitable phenyl substituents in each case being those mentioned in the case of R', R2 furthermore represents phenyl, phenylcarbonyl, phenyloxycarbonyl, phenylcarbonyloxy or phenylaminocarbonylaminocarbonyloxy, each of which is optionally monosubstituted to trisubstituted by identical or di~,cl.L substituents, suitable phenyl substituents in each case being those mentioned in the case of R', R2 furthermore represents heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylaminocarbonyloxy, each of which have 2 to 9 carbon atoms and 1 to 3 identical or di~elel,l hetero atoms (in particular nitrogen, oxygen and/or sulphur) in the heteroaryl moiety and each of which is optionally monosubstituted to trisubstituted by identical or difre,clll substituents, suitable heteroaryl substituents in each case being the phenyl substituents mentioned in the case of R', LeA29 565 -21-~1~8~9~

R3 represents cyano, fluorine, chlorine, bromine, or a s~aight-chain or branched radical from the series con~i~ting of alkyl, alkenyl, allcinyl, alkoxy, alkenyloxy, allcinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl and alkylcarbonyloxy, eachof which has up to 4 carbon atoms in the individual alkyl, alkenyl or allcinyl S moieties and each of which is optionally monos~lkstituted to trisubstituted by identical or di~elclll substituents from the series cnn~i~ting of fluorine, chlorine and bromine, or represents alkyl, alkenyl, allcinyl, alkoxy, alkenyloxy, allcinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphcryl, each of which has up to 4 carbon atoms in the individual alkyl, alkenyl or allcinyl moieties and each of which is optionally monosubstituted or disubstituted by identical or di~lclll substituents, suitablesubstituents in each case being:

straight-chain or branched alkoxy having 1 to 3 carbon atoms or phenyl which is optionally monosubstituted or ~ bstit~tpA by identical or di~lcllt substituents, suitable phenyl sllbstitl~Pnt~ being those mentioned in the case of R', R3 furthermore represents amino or arninocarbonyl, each of which is optionally monosllbstit~ltP~l or ~ bstihltPrl by identical or di~elc;lll substitllPnt~, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 4 carbon atoms, in each case optionally monosubstituted or disubstituted (identically or dirr~lcl~tly by straight-chain or branched alkyl having 1 to 4 carbon atoms) carbamoyl, thiocarbamoyl or slllph~mQyl, cycloalkyl, cycloalkylcarbonyl, or cycloalkyloxycarbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 4 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of Le A 29 565 - 22 -~15~996 which has 2 to 4 carbon atoms in the ~lk~n~iyl moiety, phenylalkyl, phenylalkylcarbonyl or phenylalkyloxycarbonyl, each of which has 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosllkstituted or ~ ksti~ 1 in the phenyl moiety by identical or di~.ellt sllbstit l~ntc, or phenyl, phenylcarbonyl or phenyloxycarbonyl, eachof which is optionally monosubstituted or ~ lbstitl~te~l in the phenyl moiety byidentical or dil~ substil~l~nt~, suitable phenyl substituents in each case being those mentioned in the case of R', R3 furthermore represents phenyl which is optionally monosubstituted to trisubstituted by identical or di~t;lGlll sukstituent~, suitable phenyl substi~nt~
in each case being those mentioned in the case of R', A~, A2, A3 and A4 in each case represent N(nitrogen), N-CHRIR2 or CX, the hetero-fused ring having at least one, but not more than two, nitrogen atoms simlllt~n~ously and all positional isomers being possible, so that CXI, CX2, CX3 e~ist in the case of one nitrogen atom and CX' and CX2 exist in the case of two nitrogen atoms, and, when either A', A2, A3 or A4 represent N-CHR'R2, the imidazole ring exists only in monosubstituted form (R ), and X', x2 and X3 independently of one another in each case represent hydrogen, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 4 carbon atoms, cycloalkyl having 3, S or 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogeno-alkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, or represent divalent dioxyalkylene having 1 to 3 carbon atoms which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 3 carbon Le A 29 565 - 23 -`` 21~8996 atoms and straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or di~elclll halogen atoms, furthermore represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 3 carbon atoms in the alkyl moiety, S cycloalkyloxycarbonyl having 3, 5 or 6 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or di~elclll substi~l~nt~, suitable amino substitllent.
in each case being:

in each case straight-chain or branched alkyl having 1 to 3 carbon atoms, halo~no~lkyl having 1 to 3 carbon atoms and 1 to 7 halogen atoms, alkoxyallyl or alkylcarbonyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, or phenylcarbonyl, phenylsulphonyl, phenylaminocarbonyl or phenylmethylsulphonyl, each of which is optionally monosubstituted to tri~lbstit~ltecl in the phenyl moiety by identical or diLL~lcll~
sllbstit~l~nt~, suitable phenyl s~bstit~lent~ in each case being those mentioned in the case of R';

X', x2 and X3 furthermore represent phenyl, phenyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl, phenylsulphonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulphonyl or phenylazo, each of which is optionally monosubstituted to trisubstituted in the phenyl moiety by identical or dirrelc~l~
substituents, suitable phenyl substitllçnt~ in each case being those mentioned in the case of R', and where at least one of the substituents X', x2 and X3 represents in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 3 carbon atoms and 1 to 7 identical or di~e,clll halogen atoms, or represents straight-chain or branched alkylsulphonyl having 1 to 3 carbon atoms, or represents divalent dioxyalkylene having 1 to 3 carbon atoms which is optionally monosubstituted to tetrasubstituted by identical or di~e,elll substituents from the series consisting of halogen, straight-chain or branched Le A 29 565 . - 24 -' ~1589g~

- alkyl having 1 to 3 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or di~e~ l halogen atoms, furthermore represents hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 3 carbon atoms in the alkyl moiety, cycloallyloxycarbonyl having 3, 5 or 6 carbon atoms in the cycloalkyl moiety, or amino or ~minoc~rbonyl, each of which is optionally monosllbstituted or disubstituted by identical or di~ ll sllbstit~lent~, suitable amino substituents in each case being:

in each case straight-chain or branched alkyl having 1 to 3 carbon atoms, halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 halogen atorns, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, or phenylcarbonyl, phenylsulphonyl, phenylaminocarbonyl or phenylmethylsulphonyl, each of which is optionally monos~bstituted to tri~uhstitute~l in the phenyl moiety by identical or di~lclllsllbstit~lPnts, suitable phenyl substituents in each case being those mentioned in the case of R';

X', x2 and X3 furthermore represent phenyl, phenylthio, phenylsulphinyl, phenylsulphonyl, phenylsulphonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulphonyl or phenylazo, each of which is optionally monosubstituted to trisubstituted in the phenyl moiety by identical or dif~
substituents, suitable phenyl substituents in each case being those mentioned inthe case of R'.

Substituted hetero-fused imidazoles of the general formula (I) LeA29 565 -25 -` 21~8996 3 ~,A~ N
A ~ \~ 3 ~1 A~
CH--R
l2 which may be mentioned individually in addition to the compounds mentioned in ~e.l~ion examples are ~ose which follow:

Le A 29 565 - 26 -21589~6 Table I

x X ~
C~R
R

Xl X2 X3 Rl R2 R3 H H H H OEt CF3 H H H H OPr CF3 H H H H OCH~CH CF3 H H H H OiPr CF3 H H H H OnBu CF3 H H H H O u CF3 H H H H 0~3u CF3 H H H H Osec.Bu CF3 H H H H OCH2CH20Me CF3 H H H H OCH2CH20Et CF3 H H H H N COOEt CF3 Me H H H H N-COOEt CF3 H H H H N-COOEt CF3 Pr N-COOEt H H H H b CF3 H H H H N-COOEt CF3 H H H H N-COOEt CF3 nPr H H H H N-COOEt CF3 iPr H H H H N--COOE~ CF3 Le A 29 565 - 27 -2 1 ~ 6 Xl X2 X3 Rl R2 R3 H H H H N ' ~ CF3 o NL~
H Br H H
Br H H H
H Br H H
H Cl H H
Cl H H H
H H Cl H
F H H H
H F H H
H H F H

H H H H CH= CH2 CF3 H H H H C~CH CF3 H H H H (H3)2ccoNH- CF3 Le A 29 565 - 28 -- 2158~9~
.
- All the exarnples also apply to R3 = CHF2, R3 = C2Fs, R3 = C3F7, and, additionally, the R2 and R3 radicals can be varied, as shown in the Table, for each X' to X3 pattern.

The s~bst~ ent variations shown in the above table can also be given for the other isomeric pyridines:

and ~F"nd X CHRR X
XX~3~N , X~cN RR l~¢CN

CHR R X X

S This variation, limited to X~ and X2, also applies analogously to the pyrimidinoimidazoles X
,~ X~

CHR-R X CHR-R

Le A 29 565 - 29 -~ 21~89~6 the pyridazines X - X
N~ R3 NJ~ \>--R
N~--N N~J--N
x2 CHR R X CHR-R

X~ , ~ ~X

and the pyra~nes X ~X ~ XN~X \~R~
CHR R CHR-R

If, for example, the pyrimidinoimidazole (1) and chloromethyl ethyl ester are used as starting compounds, the course of the reaction of the process according to the invention 5 can be represented by the following equation:

Le A 29 565 - 30 -3 ~X \~CF3 + 3 CICH2 O C2Hs HCI

(1) ¦~C ~CF3 + ¦~X ~CF3 + [~ \~CF3 CHzOC2H5 CH2Oc2Hs Cl~20C2Hs Formula aI) provides a general definition of the hetero-fused imidazoles required as starting materials for carrying out the process aecording to the invention. In this formula (TI), A~, A2, A3, A4 and R3 ~lcr~l~ly represent those radicals which have already been mentioned in conn~ction with the description of the compound of theS formula (I) aecording to the invention as being plcr~lcd for these substituents.

The lH-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 eompounds fur~ermore required as 10 educts for carrying out the proeess aecording to the invention. In this formula (III), R~
and R2 plcr~l~l)ly represent those radieals which have already been mentioned inconnection with the substances of the formula (I) according to the invention as being preferred for the substituents.

M represents a leaving radical cu~tom~ry in alkylating agents, pl~rel~bly halogen, lS arylsulphonate, arylalkylsuphonate, alkylsulphonate, alkylearbonyloxy or arylcarbonyloxy, particularly pl~rel~bly ehlorine, bromine, iodine, Cl 8-alkylsulphonate, tolylsulphonate, phenylsulphonate, C,8-alkylcarbonyloxy, or benzoyl, and partieularly preferably ehlorine, bromine, C,-C2-alkylsulphonate, phenylsulphonate, tolylsulphonate, C,-C3-alkylcarbonyloxy or benzoyl.

Le A 29 565 - 31 -215~99~
Ihe compounds of the formula (III) are known or can be obtained in analogy to known processes (cf., for exarnple, DE 20 40 175; DE 21 19 518; Synthesis 1973~ 703).

Suitable diluents for carrying out the process according to the invention are inert organic solvents. Ihese include, in particular, aliphatic, alicyclic or aromatic, optionally 5 halo~n~ted hydrocarbons, such as, for example, ben_ine, ben7~n~., toluene, xylene, chlorobenzene, dichlorobenzene, petroleurn ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether or ethylene glycol diethyl ether, k~.t~n~, such æ aoetc)n~; bllt~non~ or methyl isobutyl ketone;
10 nitriles, such as a~ .ile, propionitrile or l~ ile; amides, such as N,N-dimethylÇolll~llide, N,N-dimethyl~cet~mide, N-methylfo, . .~ ilide N-methyl-pyrrolidone or h~x~ll~lhylphosphoric triarnide; esters, such as methyl acetate or ethyl acetate, or bases such as pyridine, or organic acids such as forrnic acid or acetic acid.

Ihe process accorcling to the invention is lx~r~l~ly carried out in the presence of a 15 suitable reaction auxiliary. Suitable reaction auxiliaries are all cu~loll~y inorganic or organic bases. Ihese include, for ~ le, the hydrides, hydroxides, amides, alcoholates, ~ceS~t~, carbonates or hydrogen carbonates of alkaline earth metals or alkali metals, such as, for example, sodium hydride, sodium amide, lithiurn diethylamide, sodium methylate, sodium ethylate, potassiurn tert-butylate, sodium 20 hydroxide, potassium hydroxide, ~mmonium hydroxide, sodium acetate, potassiumacetate, calcium acetate, ~mm~mium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, organolithium compounds, such as n-butyllithium, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, di-isopropyl-ethylamine, 25 tetramethylguanidine, N,N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N,N-dimethylaminopyridine, dia_abicyclooctane (DABCO), dia_abicyclononene (DBN) or dia-abicyclo~ ~ne (DBU).

In those cases where A in formula (III) represents an alcohol, alkanoyloxy or alkoxy group, suitable reaction auxiliaries also include organic or inorganic acids, such as, for 30 example, sulphuric acid, hydrochloric acid, p-toluenesulphonic acid, Le A 29 565 - 32 -~15899~
-perfluorobutane.slllrhonic acid or strongly acidic ion e~r~l~n~.

If a~ o~liate, the process according to the invention can also be carried out in a two-phase system7 such as, for example, water/toluene or water/dichloro~ h~nP7 if ~plulJliate in the presence of a suitable phase ll~rel catalyst. Examples of such S catalysts which may be mentioned are: tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl-methylphosphonium bromide, trimethyl-C,3/C,5-alkyl~mm-nium chloride, trimethyl-C~3/C~5-alkyl~mm~ nium bromide, dibenzyl-dime~yl-~mml)nium methyl~ .lph~tç, dimethyl-C,2/C,4-alkylbenzylammonium chloride, dimethyl-C,2/C,4-10 alkylbenzylammonium bromide, tetrabutylammonium hydroxide,triethylbenzylammonium chloride, methyltrioctylammonium chloride, trimethylbenzyl~mmc)nium chloride, lS-krone-5, 18-krone-6 or tris-[2-(2-methoxyethoxy}ethyl] -amine.

When carrying out the process according to the invention, the reactiûn ten~l~ lres can lS be varied within a suks~nti~l range. In general, the process is carried out at Lures b~w~al -70C and +200C, pl~,f~.~ly at ~ lleS btlwt~ll 0C and 130C.

The process according to the invention is conventionally carried out under atmc)sphPric pressure. However, it can also be carried out under elevated or reduced pressure.

To ca~Ty out the process according to the invention, 1.0 to S.0 mol, pl~ ~ly 1.0 to 2.5 20 mûl, ofthe compound ofthe formula (III) and, if a~l~liate, 0.01 to S.0 mol, pl~fel~bly 1.0 to 3.0 mol, of reaction auxiliary are generally employed per mole of lH-hetero-fused imidazole of the formula (II).

In a particular embo limPnt, it is also possible to first silylate the lH-hetero-fused imidazoles of the formula (II) in a prec~ing reaction step with the aid of customary 25 silylation methods, for example with hexamethyl~ 7~nP or llin~lllylsilyl chloride, at temperatures between -20C and +50C, if al~pr~liate in the presence of a suitable catalyst, such as, for example, sulphuric acid, trifluoroætic acid, ammonium sulphate, imidazole or saccharin, and to react the resulting hetero-fused Le A 29 565 - 33 -21~9~
l-llill,~lh~lsilylimidazoles in a subsequent second step with alkylating agents of the forrnula (II) in accordance with the process according to the invention. In this case, it is advantageous to add tin tetrachloride as a catalyst for the alkylation reaction (cf., for example, Chem. Heterocycl. Comp. USSR 24, 514 [1988]) 5 The reaction is carried out and the reaction products are worked up and isolated by known methods (cf. in this context also the p~ ion examples).

The end products of the formula (I) are purificd with the aid of cu~loll~y processcs, for example by colurnn cl~n~lography or by rccryst~lli7~tion.

Thcy are charactcrized with the aid of the melting point or, in the case of compounds 10 which do not crystallize - in particular in the case of regio isomcr mixturcs -, with the aid of proton nuclear rcsonance spectroscopy ('H NMR).

The active compounds according to the invcntion are suitable for co~ ;"g anirnalpests, pl~r~l~bly ~ hlol)ods and nematodes, in particular insccts and arachnida, which are cncountcrcd in agriculture, in forcstry, in the protcction of stored products and of 15 materials, and in the hygicne field. They are active against normally scnsitive and resistant specics and against all or some stagcs of development. The abovemcntioned pests include:

From the order of the Isopoda, for example, Oniscus asellus, Arrnadillidium vulgare and Porcellio scaber.

20 From the ordcr of the Diplopoda, for example, Blaniulus glTth~
From the ordcr of the Chilopoda, for example, Geophilus carpophagus and Scutigera spec.
From the ordcr of the Symphyla, for example, Scutigcrella imm~r,~ t~
From the ordcr of the Thysanura, for example, Lepisma saccharina 25 From the ordcr of the Collembola, for example, Onychiurus ~rm~hl~.
From the order of the Orthoptera, for exarnple, Blatta orientalis, Periplaneta amcricana, Leucophaea maderae, Blattella germanica, Acheta domcsticus, Gryllotalpa spp., Locusta Le A 29 565 - 34 -215~9~6 migratoria migratorioides, Melanoplus di~lallialis and Schistocerca gregaria From the order of the Dermaptera for example, Forficula auricularia From the order of the Isoptera, for example, Reticulitermes spp..
From the order of the Anoplura for example, Phylloxera vastatrix, Pemphigus spp., S Pediculus hllm~ml~ corporis, H~Pm~tQpinus spp. and Linogn~th--~ spp..
From the order of the Mallophaga, for t;xa~ , Trichodectes spp. and D~m~linP~ spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.
.

From the order of the H~le~ , for example, Eurygaster spp., Dysdercus 10 intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

From the order of the Homoptera, for exarnple, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus ar~n~lini~ Macrosiphl-m avenae, Myzus spp., Phorodon hllmllli, Rhopalosiphum padi, Empoasca spp., Euscelis 15 bilobatus, Nephot~ttix cincticeps, Lecanium corni, S~i~seti~ oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus pinianus, Cheimatobia bruma~a, Lithocolletis blancardella, Hyponomeuta padella, 20 Plutella m~r llipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
Buc,c -l~trix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana~ Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis fl~mmr~ Prodenia litura, Spodoptera spp., Trichoplusia ni, Ca~pocapsa pomonella,Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, 25 Tineola bisselliella, Tinea pellionella, Hofmannophila pse~-~ospretella, Cacoecia podana, Capua reticulana, Chori~tonr -ra f u~ a, Clysia ambiguella, Homona m~
and Tor~ix viridana From the order of the Coleoptera, for example, Anobium puncl~t--m, Rhizopertha Le A 29 565 - 35 -21~96 dominica, ~nthoscelides obtectus, ~nthosc~lides obtectus, Hylotrupes bajulus, Agelastica alni, ~eptin~tarsa ~l~ern1in~t~ Phaedon cochleariae, Diabrotica spp.,Psylliodes chrysocephala, Epilachna varive stis, Atomaria spp., C)ryzaephilus surin~m~i.c, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites 5 sordidus, Ce~lthorrhynchus ~c~imili~, Hypera postica, D~ ~ spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Melig~th~ aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derus spp., Melolontha melolontha, ~"~ i",~llon solsti tialis and Costelytra 7~1~n~ica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocarnpa spp., l0 Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., C~11iphora ery~roceph~1~ Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortnl~m1~,15 Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order ofthe Siphonaptera, for example, Xenopsylla cheopis and Ceratophyllus spp..
From the order of the Arachnida, for example, Scorpio maurus and T~trodectus 20 rn~t~n~

From the order ofthe Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus ~llin~e, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus SpP.?
Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp.
25 and Tetranychus spp..

The active compounds according to the invention are ~ tin~ hed by a powerfùl insecticidal and acaricidal activity.

Le A 29 565 - 36 -- 215~9~
Ihey can be employed particularly succ~ lly for c~ k~ g plant-injurious insects,such as, for example, against the larvae of the mustard beetle (Phaedon cochleariae) or against the larvae of the green rice leafhopper (Nephotettix cincticeps) against the caterpillars of the tli~rnc)n~l-back moth Plutella m~rlllipennis.

S The active compounds according to the invention can be fur~llPrmore used as defoliants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the sllb~ according to the inventionact as total or selective herbicides depends ~s~ti~lly on the amount used.

10 The active compounds according to the invention can be used, for example, in conn~ction with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, ~lillrn, Stellaria, Matricaria, Antl~ , Galinsoga, Chenopodium, Urtica, Senecio, A~ lh ls, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus,15 Sonchus, Solanum, Rorippa, Rotala, Tintl~i~ Lamium, Veronica, Abutilon, Emex,Datura Viola, Galeopsis, Papaver and Centaurea Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus,Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana Lycopersicon, Arachis, BrassicaT ~ct~lc~ Cucumis and Cucurbita.

20 Monocotyledon weeds of the genera: Echinochloa Setaria~ Panicum, Digitaria Phleum, Poa, Festuca, Eleusine, Brachiaria Lolium, Bromus, Avena Cyperus, Sorghum, Agropyron, Cynodon, Monochoria Fimbristylis, Sagittaria Eleocharis, Scirpus, Paspalum, T~ mllrn, Sphenoclea Dactyloctenium, Agrostis, Alopecurus andApera 25 Monocotyledon cultures of the ~enera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

Le A 29 565 - 37 -21~99~
However, the use of the active compounds according to the invention is in no wayrestricted to these genera, but also extends in the same manner to other plants.
Ihe compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on pa~s and squares 5 with or without tree pl~ntin~. Equally, the compounds can be employed for combating weeds in perennial cultures, for exarnple a~l~ions, decorative tree pl~ntin~;, ol~l~ds, vineyards, citrus groves, nut ol-,l~, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit pl~ntin~ and hopfields, and for the selective cn"~ li"g of weeds in annual cultures.

10 ~he active compounds according to the invention can be employed particularly sllcc~sfillly for co"~ g monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon cultures, such as, for example, wheat, maize or soya beans.

lhe active compounds can be converted into the cllctom~ry fnrm~ tions, such as solutions, emulsions, suspensions, powders, foams, pastes, granule~s, aerosols, natural 15 and synthetic materials impregn~t~1 with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents, liquified gases under pressure and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying 20 agents and/or dispersing agents and/or foarn-forming agents.

In the case of the use of water as an extender, organic solvents can, for exarnple, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main:
aromatics, such as xylene, toluene or alkyln~phtll~lenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or 25 methylene chloride, aliphatic hydrocarbons, such as cyclohexane or ~ua~ s~ for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as LeA29 565 -38-. . 215~99~
dimethylro."~.n;de and dimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk quartz, attapulgite, montmorillonite or diatomaceous ear~, and ground synthetic minerals, such as highly disperse silica, S alumina and silicates; as solid carriers for granules there are suitable: for example crushed and fractionated natu~l rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, mai7e cobs and tobacco stalks; as emulsifying and/or foam forming agents there are suitable: for example non-ionic and 10 anionic ~mlllcifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl~ rhon~t~, alkyl sl-lph~t~s, arylsulphon~t~s as well as albumen hydrolysis products; as dispersing agents there are suitable: for ~ lc lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the 15 form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as ceph~lin~ and lecithin~, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, 20 titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Ihe formulations in general contain between 0.1 and 95 per cent by weight of active compound, ~,t;re,al)ly between 0.5 and 90%.

25 For comh~ting weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Le A 29 565 - 39 -` 21~96 Suitable herbicides for the mixtures are known herbicides, for example anilides such æ, for example, diflufenican and propanil; arylcarboxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids such as, forexample, 2,4-D, 2,4-DB, 2,~DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-S phenoxy-alkanoic esters such æ, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and qui alofop-ethyl; ~7inonPs such æ, for example, chloridazon and norflurazon; c~b~l~es such as, for example, chlol~lo~
cl~m~lipham, phPnmPAi~ham and p~ ; chlor~cet~nilides such as, for example, alachlor, acetochlor, butachlor, m~t~7~rhlor, metolachlor, pretilachlor and propachlor;
10 dinitro~nilinPs such as, for example, oryzalin, pPn~limPth~lin and trifluralin; diphenyl ethers such as, for example, acifluorfen, bifenox, fluoroglycofen, folll~s~en, halosafen, lactofen and oxyfluorfen; ureæ such as, for example, chlortoluron, diuron, fluometuron, isoproturon, linuron and methabP.n7~hi~7~-ron; hydroxyl~minPs such æ, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such 15 æ, for example, ;~ lh~ryr, ;"~ "l~.lh~be~ a~yr and im~7~ in; nitriles such æ, for example, bromoxynil, dichlobenil and ioxynil; oxy~r,et~mides such æ, for example, mefenacet; sulphonylureas such æ, for example, ami~los~-lfilron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinnslllfilron, m~t~lllfilron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifrn~lllfi-ron-methyl, triasulfuron 20 and tribenuron-methyl; thio~l,~,~les such as, for example, butylate, cycloate, di-allate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate; triazines such as, for example, atrazine, cy~n~7inP' sim~7ine, simetryn, terbutryn and terbutylazine; triazinones such as, for example, hexazinone, m~ loll and metribuzin;
others such as, for example, aminotriazole, benfuresate, bentazone, cinmethylin,25 clomazone, clopyralid, difenzoquat, dithiopyr, ethofilmrs~tç7 fluorochloridone, glufo-sinate, glyphosate, isoxaben, pyridate, quinchlorac, qninmPrac~ sulphosate and tridiphane.

Mixtures with other known active compounds, such æ fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil 30 structure, are also possible.

~he active compounds can be used as such, in the form of their formulations or in the LeA29 565 -40-21589~
use forms prepared th~lc~olll by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after S emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a s~-bst~nti~l range. It depends çssçnti~lly on the nature ofthe desired effect. In general, the amounts used are between 0.001 and 10 kg of active compound per hectare of soil surface, ~l~r~l~ly between 0.005 and 5 kg per ha When the active compounds according to the invention are used as insecticides, they can, again, be present in their commercially available form~ tions and in the use forms, prepared from these formlll~tions, as a mixture with other active compounds, such as insecticid~s, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth-re~ ting substances or herbicides. The insecticides include, for example,phosphates, ~b~ çs, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorg~ni~m~.

When the active compounds according to the invention are used as insecticides, they can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents.
Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.

The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95 per cent by weight of active compound, preferably between 0.0001 and 1 per cent by weight.

LeA29 565 -41-21S~996 lhe compounds are employed as insecticides in a c -~tom~ ne~ ,iate for the use forms.

~ ion and use of the active compounds according to the invention can be seen from the exarn~les which follow.

LeA29 565 . -42-- 2 1 ~ 9 Prepa~on exampies Example 1 ~r N N~ N Cl-C~
CF3 + ~ CF~
~N--N }3r~NH C~CI2/NEt3 Al A2 Br~ >--CF3 + ~ CF3 CH20EI CH20Et Bl B2 2.66 g (0.01 mol) 2-trifluolun,~lhyl-bromo-pyridino-[lHl-imidazole (A1/A2) and 1.75 ml (0.0125 mol) of triethylamine are dissolved in 100 ml of dichlulu~ ,e.
1.25 ml (0.0125 mol of chloromethyl methyl ether are added dropwise to this solution, the mixture is subse~l~tly heated at reflux tempe~, and stirring is contiml~l for 16 hours at reflux temperature. For working up, the cooled reaction mi~ure is washed three times using 30 ml of water in each case, dried over MgSO4 and con~Pntrated in vacuo and the residue is purified by ~l~ru~ ography on silica gel (eluent:
dichloromethane).
2.40 g (74 % of theory) of 1-ethoxymethyl-2-trifluoromethyl-bromopyridino imidazole are obtained as a regio isomer mixture (B1/B2) in a ratio of 60:40 (m.p.: 68C).
'H NMR (CDCI3/tetramethylsilane): ~ = 5.68 (s, 2~; 5.85 (s, 2H) ppm (in each case N-CH2-O-).

Ihe isomers can be separated by recryst~lli7~tion with an ether/petroleum ether mixture.

Ihe compounds listed in the table which follows are obtained analogously.

Le A 29 565 - 43 -21~8996 Table II

A3 ~A~CN 3 A~A
CH--R

~mple A' A2 A3 A4 R' R2 R3 Physio~
No.

2 N CH CH CH H OC2H5 CF3 m.p.:92C
3 CH CH CH N H OC2H5 CF3 m.p.:l70C

4 CH N CH CH H OC2H5 CF3 'HNMR:

5.89(s,2H) S CH CH N CH H OC2H5 CF3 'HNMR:

6.08(s,2H) 6 N CH CBr CH H /C~ CF3 'HNMR':
N~ 5.90 (S, 2H) COOE

7 CH CBr CH N H /C~ CF3 'HNMR:
N~ 6.08(s,2H) a~OEt 8 N CH CBr CH H ~Et CF3 'HNMR:
N~ 5.90 (S, 2H) COOEI

9 CH CBr CH N H ~Et CF3 'HNMR':
N~ 6.10(s,2H) COOEt Le A 29 565 - 44 --`` 21~9~6 Table II (con~im~

Example A' A2 A3 A4 R' R2 R3 Physical data No.

N CH CBr CH H/~ P~P~l CF3 'H NMR':
N\COOEt 5.89 (s, 2H) I l CH CBr CH N H~P~P~ CF3 'H NMR':
N~ 6.09 (s, 2H) a~OEt 12 N CH CBr CH H ~ ~ CF3 'H NMR:
N CO~OB 5.90 (S, 2H) 13 CH CBr CH N H ~~~ CF3 'H NMR':
N~/ 6.11 (s, 2H) `ax~, 14 N CH CH CH HOC2H5 CHF2 'H NMR:
5.91 (s, 2H) CH CH CH N HOC2H5 CHF2 'H NMR':
6.14 (s, 2H) 16 CH N CH CH H ~Et CF3 'H NMR':
~;\ 5.83 (s, 2H) COOE~ m.p.: 120C

17 CH CH N CH H~Et CF3 ~H NMR:
N~ 6.03 (s, 2H) alOEt 18 N CH CH CH HCH=CH2 CF3 'H NMR':
5.35 (d, J =
3Hz, 2H) LeA29 565 -45 -~lS8~
Table II (contiml~) Example A' A2 A3 A4 R~ R2 R3 Physical data No.

19 N CH CH CH H COCH3 CF3 m.p.: 148-N CH CH CH H CN C~2 IH NMR':
5.48 (s, 2H) 21 N CH CH CH H ~EI CF3 'H NMR':
COOEt 5.89 (s, 2H) 22 CH CH CH N H ~EI CF3 IH NMR':
COOEI 6.12 (s, 2H) 23 N CH CH CH H N/~- CF3 IH NMR':
~ , 5.94 (s, 2H) 24 CH CH CH N H /~' CF3 IH NMR':
~\ 6.12 (s, 2H) COOlt-N CH CH CH H u''~ CHF2 'H NMR':
)~~ 5.88 (s, 2H) \J m.p.: 119C

26 CH CH CH N H ,~OE CHF2 'H NMR:

~0 6 02 (s, 2H) 27 N CH CH CH H /cooE CHF2 'H NMR:
~'~E 5.93 (s, 2H) LeA29 565 -46-- 21~S99~

Table II (contim~

Example A' A2 A3 A4 R' R2 R3 Physical da~
No.

28 CH CH CH N H ~U~h CHF2 ~HNMR:
Nb 6.14(s,2H) m.p.:84C
29 N CCI CH CH H ~o~Et CF3 IH NMR':
N~ 5.88(s,2H) CH CH CCI N H ~~Et CF3 'H NMR':
N~t 6.02(s,2H) 31 N CH CH CH H CN CF3 m.p.: 184-CHR, 186C

~ 'H NMR spectra were recorded in deuterochloroform (CDC13) with t~ }lylsilane (TMS) as the int~rn~l standard. The data given is the chemical shift as ~value in ppm; in all cases, the N-CH2RIR2 proton shift is given.

LeA29 565 -47-~1~89~
Example A:

est Solvent: 5 parts by weight of ~çet--n~
Fm~ ifier: l part by weight of alkylaryl polyglycol ether S To produce a suitable ~ Lion of active compound, one part by weight of active compound is mixed with the stated amount of solvent, the stated arnount of emulsifier is added and the con~ is diluted with water to the desired conrPn1ration.

Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the pl~p~lion of the active compound. It is expedient to keep COl~t~l~ the arnount of water per unit area Ihe collce~ ion of the active compound in the ~lc~lion is ofno importance, only the arnount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % ~l~m~
in comparison to the development of the untreated control. Ihe figures denote:

0%= no action (like untreated control) 100% = total destruction In this test, a clearly superior activity combined with a similarly good crop plant selectivity is shown by the compounds of P~ tion Examples (l) and (6), for example in wheat crops at application rates of l,000 g per hectare when applied against weeds such as Chenopodium (95-lO0 %), Galinsoga (95-lO0 /0), Matricaria (90-95 %), Portulaca (lO0 %), Stellaria (lO0 %) and Viola (90-95 %), the wheat rem~ining unharmed (0 /O).

Le A 29 565 - 48 -- ` 21S89~
Table III

Pre~~ g~llce test/greenhouse Active comp. Applica- Wheat Cheno- Galins- Matri Portu- Stell Viola tion rate in podium ogac-aria laca -aria g/ha . ~.

~"

Le A 29 565 - 49 -21~ 9~
Examnle B:

Post~..~ ,ce test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether S To produce a suitable plc~ ion of active compound, one part by weight of active compound is mixed with the stated arnount of solvent, the stated amount of ~~ ifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5 - 15 cm are sprayed with the ~c~lion of theactive compound in such a way as to apply the particular amounts of active compound 10 desired per unit area. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:

0% = no action (like untreated control) 100% = total destruction 15 In this test, a clearly superior activity and crop plant selectivit,v is shown by the compounds of l~cp~lion Examples (1), (6) and (12), for exarnple in wheat crops at application rates of 250 g per hectare when used against weeds such as Datura (90-100 %), Heli~nthll~ (90-100 %), Portulaca (90-100 %), Sinapis (100 /0) and Solanurn (80-100 %), the wheat l~",~it~ g -~h~ A (0 %).

Le A 29 565 - 50 -- 2iS~9~
Table IV

Post-emergence test/greenhouse Active Appli- Wheat Datura Helian- Portu- Sinapis Solan-~ol"~ul,d tion thus laca urn rate in g/ha 2s0 o 90 90 90 Ioo 80 ~ ~. (12) ~l 2s0 o loo loo loo loo loo 0~

.,.
2s0 o loo loo loo loo loo OC~

LeA29 565 - 51-21 i8~9~
Exan~le C:

l~edon lan~ae test Solvent: 7 parts by weight of dimethylro~ de Emulsifier: 1 part by weight of alkylaryl polyglycol ether s To produce a suitable ~lc~ ion of active compond, one part by weight of active compound is mixed with the stated amount of solvent and the stated amount of e~ ifier, and the conr~trate is diluted with water to the desired co~ .~ion.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the ~lc~ lion of active compound of the desired concentration and are infested with mustard beetle o larvae (Phaedon cochleariae) while the leaves are still moist.

After the specified periods of time, the destruction in % is ~l~t~nin~l 100% means that all the beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

In this test, for example the compound of P'l~p~ion Exarnple (1) shows a degree of destruction of 100 % after 7 days at an active compound concentration 0.1 %.

Le A 29 565 - 52 -215g99G
Table V

Phaedon larvae test (plant-injurious insects) Active com~ounds Active Degree of compound des~uction in %
concentration afcer 7d in %
N 0.1 100 H3C O N~Br F3C N (1 ) Le A 29 565 - 53 -21~j8~9~
- Examnle D:

Plutella test Solvent:S parts by weight of dimethylformamide Emulsifier:1 part by weight of alkylaryl polyglycol ether S To produce a suitable ple~ Lion of active compond, one part by weight of active compound is mixed with the stated amount of solvent and the stated amount of ~m~ ifier, and the cQn~Pn~ate is diluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the ~ lion of active compound of the desired ccn~ntration and are infested with caterpillars of the 10 tli~montl-back moth (Plutella m~clllir~ennis) while the leaves are still moist.

After the specified periods of time, the destruction in % is ~let~rminffl 100% means that all the caterpillars have been killed; 0% means that none of the caterpillars have been killed.

In this test, for exarnple the compound of P~ ion Example (1) shows a degree of destruction of 100 % ai'~er 7 days at an active compound concentration of 0.1 %.

Le A 29 565- 54 -Table V~ 215 8~9 ~

Plutella test (plant-injurious insects) Active com~ounds Active Degree of com~ound destruction in %
concentration af~er 7d in%
N 0.1 100 5 H3C O N ~Rr F3ClN (1) LeA29 565 - 55 -- 2 1 ~
ExamDle E:

Nephotefflx test Solvent: 7 parts by weight of dimethyll~l,llan~ide Emulsifier: 1 part by weight of alkylaryl polyglycol ether 5 To produce a suitable ~ ion of active compond, one part by weight of active compound is mixed with the stated amount of solvent and the stated amount of ifier, and the c )n(~P.n~ate is diluted with water to the desired concentration.
Rice se~llin~ (Oryza sativa) are treated by being dipped into the ple~alion of active compound of the desired concentration and are infested with larvae of the green rice 10 leafhopper (N~ lelli~ cincticeps) while the leaves are still moist.

After the specified periods of time, the destruction in % is det~nnined. 100% means that all the leafhoppers have been killed; 0% means that none of the leafhoppers have ; been killed.

In this test, for example the following compounds of pl~lion examples (1) and (10) 15 show degrees of destruction of up to 100 % after 6 days at an active compound concentration of 0.1 /O.

Le A 29 565 - 56 -21~9~6 Table VII

Nephotefflx test (plant-injurious ir~ects) Active compounds Active Degree of compound destruction in %
concentration after 6d in %
N O.l lOO
5 H3C O N ~Br F3C N (1 ) F,C~N 0.1 100 ~ ~N ~Br (10) H3C ~>

Le A 29 565 - 57 -

Claims (10)

Patent Claims

1. New substituted hetero-fused imidazoles of the general formula (I) in which R1 represents hydrogen or a straight-chain or branched, in each case optionallyunsubstituted or substituted, radical from the series consisting of alkyl, alkoxy and aryl, R2 represents hydroxyl, cyano or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylcarbonyloxy and (hetero)arylamino-carbonylaminocarbonyloxy, R3 represents cyano, halogen or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkinyloxy, dialkoxyphosphonyl, amino, aminocarbonyl and aryl, A1, A2, A3 and A4 in each case represent N(nitrogen), N-CHR1R2 or CX, the hetero-fused ring having at least one, but not more than two, nitrogen atoms simultaneously and all positional isomers being possible, so that CX1, CX2, CX3 exist in the case of one nitrogen atom and CX1 and CX2 exist in the case of two nitrogen atoms, and, when either A1, A2, A3 or A4 represent N-CHR1R2, the imidazole ring exists only in monosubstituted form (R3), where X1, X2 and X3 in each case independently of one another represent hydrogen, halogen, cyano, nitro or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl and cycloalkyl, or represents hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl-oxycarbonyl, or represents in each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substitutents X1, X2 or X3 represents halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkylsulphonyl, or represents optionally substituted fused dioxyalkylene, or represents hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, or represents in each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl.

2. New substituted hetero-fused imidazoles of the general formula (I) according to Claim 1, characterized in that R1 represents hydrogen or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl and alkoxy, each of which has 1 to 8 carbon atoms, or represents phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being:

halogen, cyano, nitro in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or divalent dioxyalkylene having 1 to 5 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 6 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, or phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 6 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, R2 represents hydroxyl, cyano or a straight-chain or branched radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each of which has up to 8 carbon atoms in the individual alkyl or alkenyl or alkinyl moieties and each of these radicals optionally being monosubstituted or polysubstituted by identical or different substitutents, suitable substituents in each case being:

fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 8 carbon atoms, or aryl having 6 to 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 5 hetero atoms (in particular nitrogen, oxygen and/or sulphur), these aryl or heteroaryl substituents in each case optionally being monosubstituted or polysubstituted by identical or different substituents and suitable aryl or heteroaryl substituents being those mentioned in the case of R1, R2 furthermore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, carbamoyl, thiocarbamoyl or sulphamoyl, each of which is monosubstituted or disubstituted by identical or different straight-chain or branched alkyl substituents having 1 to 8 carbon atoms, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 8 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 8 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkanediyl moiety, arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1, R2 furthermore represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1, R2 furthermore represents heteroaryl, heteroarylcarbonyl, hetero-aryloxycarbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonyl-aminocarbonyloxy, each of which has 2 to 9 carbon atoms and 1 to 5 identical or different hetero atoms (in particular nitrogen, oxygen and/or sulphur) in the heteroaryl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable heteroaryl substituents in each case being the aryl substituents mentioned in the case of R1, R3 represents cyano, fluorine, chlorine, bromine, iodine or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of cycloalkyl, alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkenyloxy, each of which has up to 8 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties, suitable substituents in each case being: fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 8 carbon atoms, or aryl having 6 to 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 5 hetero atoms (in particular nitrogen, oxygen and/or sulphur ), each of these aryl or heteroaryl radicals optionally being monosubstituted or polysubstituted by identical or different substituents and suitable aryl or heteroaryl substituents being those mentioned in the case of R1, R3 furthemore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, carbamoyl, thiocarbamoyl or sulphamoyl, each of which is monosubstituted or disubstituted by identical or different straight-chain or branched alkyl substituents having 1 to 8 carbon atoms, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 8 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 8 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkanediyl moiety, arylalkyl, aryalkylcarbonyl or arylalkyloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1, R3 furthermore represents aryl having in each case 6 to 10 carbon atoms in the aryl moiety which is in each case optionally monosubstituted or polysubstituted by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1, A1, A2, A3 and A4 in each case represent N(nitrogen), N-CHR1R2 or CX, the hetero-fused ring having at least one, but not more than two, nitrogen atoms simultaneously and all positional isomers being possible, so that CX1, CX2, CX3 exist in the case of one nitrogen atom and CX1 and CX2 exist in the case of two nitrogen atoms, and, when either A1, A2, A3 or A4 represent N-CHR1R2, the imidazole ring exists only in monnsubstituted form (R3), and X1, X2 and X3 in each case independently of one another represent hydrogen,fluorine, chlorine, bromine, iodine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, or divalent dioxyalkylene having 1 to 5 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthermore represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case straight-chain or branched alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl, arylaminocarbonyl or arylmethylsulphonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1;

X1, X2 and X3 furthermore represent aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1, and where at least one of the substituents X1, X2 or X3 represents in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, halogeno-alkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, or represents straight-chain or branched alkylsulphonyl having 1 to 6 carbon atoms, or divalent dioxyalkylene having 1 to 5 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthrmore represents hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 8 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case straight-chain or branched alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl, arylaminocarbonyl or arylmethylsulphonyl, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different substihl~nh in the aryl moiety, suitable aryl substituents in each case being those mentioned in the case of R', X1, X2 and X3 furthermore represent aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 to 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1.

3. New substituted hetero-fused imidazoles of the general formula (I) according to Claim 1, characterized in that R1 represents hydrogen, or a straight-chain or branched radical from the series consisting of alkyl and alkoxy, each of which has 1 to 6 carbon atoms and each of which is unsubstituted or substituted, or represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents being:

fluorine, chlorine, bromine, iodine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which has 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally monosubstituted to hexasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or phenyl which is optionally monosubstituted to pentasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, halogen in each case representing fluorine, chlorine, bromine or iodine, R2 represents hydroxyl, cyano, or a straight-chain or branched radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and dialkoxyphosphonyl, each of which has up to 6 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted to pentasubstituted by identical or different substituents from the series consisting of fluorine, chlorine, bromine and iodine, or represents alkyl, alkenyl or alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphonyl, each of which has up to 6 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents in each case being straight-chain or branched alkoxy having 1 to 6 carbon atoms, or aryl having 6 or 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 4 hetero atoms (in particular nitrogen, oxygen and/or sulphur), each of these aryl or heteroaryl radicals optionally being monosubstituted to trisubstituted by identical or different substituents and suitable aryl or heteroaryl substituents being those mentioned in the case of R1, R2 furthermore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 6 carbon atoms, carbamoyl, thiocarbamoyl or sulphamoyl, each of which is optionally monosubstituted or disubstituted by identical or different straight-chain or branched alkyl substituents having 1 to 6 carbon atoms, or cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 6 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 5 carbon atoms in the alkanediyl moiety, arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted to trisubstituted in the aryl moiety by identical or different substituents or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to trisubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1, R2 furthermore represents aryl, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy or arylaminocarbonylaminocarbonyloxy, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to pentasubstituted by identical or different substituents suitable aryl substituents in each case being those mentioned under R1, R2 furthermore represents heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylcarbonyloxy or heteroarylamino-carbonylaminocarbonyloxy, each of which has 2 to 9 carbon atoms and 1 to 4 identical or different hetero atoms (in particular nitrogen, oxygen and/or sulphur) in the heteroaryl moiety and each of which is optionally monosubstituted to pentasubstituted by identical or different substituents, suitable heteroaryl substituents in each case being the aryl substituents mentioned in the case of R1, R3 represents cyano, fluorine, chlorine, bromine, iodine, or a straight-chain or branched radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl and alkylcarbonyloxy, each of which has up to 6 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and which is optionally monosubstituted to pentasubstituted by identical or different substituents from the series consisting of fluorine, chlorine, bromine and iodine, or represents cycloalkyl, alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxy-phosphonyl, each of which has up to 6 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents in each case being:

fluorine, chlorine, bromine, iodine, straight-chain or branched alkoxy having 1 to 6 carbon atoms, or aryl having 6 or 10 carbon atoms or heteroaryl having 2 to 9 carbon atoms and 1 to 4 hetero atoms (in particular nitrogen, oxygen and/or sulphur), each of these aryl or heteroaryl radicals optionally being monosubstituted to trisubstituted by identical or different substituents, suitable aryl or heteroaryl substituents being those mentioned in the case of R1, R3 furthermore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 6 carbon atoms, carbamoyl, thiocarbamoyl or sulphamoyl, each of which is optionally monosubstituted or disubstituted by identical or different straight-chain or branched alkyl substituents having 1 to 6 carbon atoms, or cycloalkyl, cycloalkylcarbonyl, or cycloalkyloxycarbonyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycabonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 6 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 5 carbon atoms in the alkanediyl moiety, or arylalkyl, arylalkylcarbonyl or arylalkyloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted to trisubstituted by identical or different substituents in the aryl moiety, or aryl, arylcarbonyl or aryloxycarbonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to trisubstituted in the aryl moiety by identical or different substituents, suitable aryl substiuents in each case being those mentioned in the case of R1, R3 furthermore represents aryl having in each case 6 or 10 carbon atoms in the aryl moiety which is in each case optionally monosubstituted to pentasubstituted by identical or different substituents suitable aryl substituents in each case being those mentioned in the case of R1, A1, A2, A3 and A4 in each case represent N(nitrogen), N-CHR1R2 or CX, the hetero-fused ring having at least one, but not more than two, nitrogen atoms simultaneously and all positional isomers being possible, so that CX1, CX2, CX3 exist in the case of one nitrogen atom and CX1 and CX2 exist in the case of two nitrogen atoms, and, when either A1, A2, A3 or A4 represent N-CHR1R2, the imidazole ring exists only in monosubstituted form (R3), and X1, X2 and X3 in each case independently of one another represent hydrogen,fluorine, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkyl-sulphinyl, halogenoalkylsulphonyl, each of which has 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally monosubstiuted to hexasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthermore represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 4 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 7 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case straight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl, arylaminocarbonyl or arylmethylsulphonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to pentasubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1;

X1, X2 and X3 furthermore represent aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to pentasubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1, and where at least one of the substituents X1, X2 and X3 represents in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 4 carbon atoms, or divalent dioxyalkylene having 1 to 4 carbon atoms which is optionally monosubstituted to hexasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, furthermore represents hydroxycabonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 4 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3 to 7 carbon atorns in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case straight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, or arylcarbonyl, arylsulphonyl arylaminocarbonyl, or arylmethylsulphonyl, each of which has 6 or 10 carbon atoms in the aryl moiety and each of which is optionally monosubstituted to pentasubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1;

X1, x2 and X3 furthermore represent aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylthiomethylsulphonyl or arylazo, each of which has 6 or 10 carbon atoms in the aryl moiety, such as phenyl or naphthyl, and each of which is optionally monosubstituted to pentasubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being those mentioned in the case of R1.

4. New substituted hetero-fused imidazoles of the general formula (I) according to Claim 1, characterized in that R1 represents hydrogen or a straight-chain or branched radical from the series consisting of alkyl and alkoxy, each of which has 1 to 4 carbon atoms and each of which is unsubstituted or substituted, or represents phenyl which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents being:

fluorine, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 3 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenalkylsulphonyl, each of which has 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, in each case straight-chain or branched alkoxyalkyl, alkoxyalkoxy, alkanoyl, alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, divalent dioxyalkylene having 1 to 3 carbon atoms which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 3 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consistingof halogen, straight-chain or branched alkyl having 1 to 3 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, halogen in each case representing fluorine, chlorine or bromine, R2 represents hydroxyl, cyano or a straight-chain or branched radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and dialkoxyphosphonyl, each of which has up to 4 carbon atoms in the individual alkyl, aLkenyl or alkinyl moieties and each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of fluorine, chlorine and bromine, or represents alkyl, alkenyl, alkinyl, alkoxy, aLkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, aLkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphoryl, each of which has up to 4 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties, and each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

straight-chain or branched alkoxy having 1 to 3 carbon atoms or phenyl which is optionally monosubstituted or disubstituted by identical or different substituents, suitable phenyl substituents being those mentioned in the case of R1, R2 furthermore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 4 carbon atoms, carbamoyl, thiocarbamoyl or sulphamoyl, each of which is optionally monosubstituted or disubstituted by identical or different straight-chain or branched alkyl substituents having 1 to 4 carbon atoms, cycloalkyl, cycloalkylcarbonyl or cycloalkyloxycarbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 4 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 4 carbon atoms in the alkanediyl moiety, phenylalkyl, phenylalkylcarbonyl or phenylalkyloxycarbonyl, each of which has 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or disubstituted in the phenyl moiety by identical or different substituents, or phenyl, phenylcarbonyl or phenyloxycarbonyl, each of which is optionally monosubstituted or disubstituted in the phenyl moiety by identical or different substituents, suitable phenyl substituents in each case being those mentioned in the case of R1, R2 furthermore represents phenyl, phenylcarbonyl, phenyloxycarbonyl, phenylcarbonyloxy or phenylaminocarbonylaminocarbonyloxy, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable phenyl substituents in each case being those mentioned in the case of R1, R2 furthermore represents heteroaryl, heteroarylcarbonyl, heteroaryloxy-carbonyl, heteroarylcarbonyloxy or heteroarylaminocarbonylamino-carbonyloxy, each of which have 2 to 9 carbon atoms and 1 to 3 identical or different hetero atoms (in particular nitrogen, oxygen and/or sulphur) in the heteroaryl moiety and each of which is optionally monosllbstituted to trisubstituted by identical or different substituents, suitable heteroaryl substituents in each case being the phenyl substituents mentioned in the case of R1, R3 represents cyano, fluorine, chlorine, bromine, or a straight-chain or branched radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl and alkylcarbonyloxy, each of which has up to 4 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of fluorine, chlorine and bromine, or represents alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or dialkoxyphosphoryl, each of which has up to 4 carbon atoms in the individual alkyl, alkenyl or alkinyl moieties and each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

straight-chain or branched alkoxy having 1 to 3 carbon atoms or phenyl which is optionally monosubstituted or disubstituted by identical or different substituents suitable phenyl substituents being those mentioned in the case of R1, R3 furthermore represents amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents in each case being:

formyl, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain or branched alkylsulphonyl having 1 to 4 carbon atoms, in each case optionally monosubstituted or disubstituted (identically or differently by straight-chain or branched alkyl having 1 to 4 carbon atoms) carbamoyl, thiocarbamoyl or sulphamoyl, cycloalkyl, cycloalkylcarbonyl, or cycloalkyloxycarbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl moiety, alkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio-carbonyl, alkoxy-thiocarbonyl or alkylthio-thiocarbonyl, each of which has 1 to 4 carbon atoms in the individual straight-chain or branched alkyl moieties, in each case divalent and cyclized alkanediylcarbonyl or alkanediyloxycarbonyl, each of which has 2 to 4 carbon atoms in the alkanediyl moiety, phenylalkyl, phenylalkylcarbonyl or phenylalkyloxycarbonyl, each of which has 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or disubstituted in the phenyl moiety by identical or different substituents, or phenyl, phenylcarbonyl or phenyloxycarbonyl, each of which is optionally monosubstituted or disubstituted in the phenyl moiety by identical or different substituents, suitable phenyl substituents in each case being those mentioned in the case of R1, R3 furthermore represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable phenyl substituents in each case being those mentioned in the case of R1, A1,A2, A3 and A4 in each case represent N(nitrogen), N-CHR1R2 or CX, the hetero-fused ring having at least one, but not more than two, nitrogen atoms simultaneously and all positional isomers being possible, so that CX1, CX2, CX3 exist in the case of one nitrogen atom and CX1 and CX2 exist in the case of two nitrogen atoms, and, when either A1, A2, A3 or A4 represent N-CHR1R2, the imidazole ring exists only in monosubstituted form, and X1, X2 and X3 independantly of one another in each case represent hydrogen,chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 4 carbon atoms, cycloalkyl having 3, 5 or 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, or represent divalent dioxyalkylene having 1 to 3 carbon atoms which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 3 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, furthermore represent hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 3 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3, 5 or 6 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case straight-chain or branched alkyl having 1 to 3 carbon atoms, halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, or phenylcarbonyl, phenylsulphonyl, phenylaminocarbonyl or phenylmethylsulphonyl, each of which is optionally monosubstituted to trisubstituted in the phenyl moiety by identical or different substituents, suitable phenyl substituents in each case being those mentioned in the case of R1;

X1, X2 and X3 furthermore represent phenyl, phenyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl, phenylsulphonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulphonyl or phenylazo, each of which is optionally monosubstituted to trisubstituted in the phenyl moiety by identical or different substituents, suitable phenyl substituents in each case being those mentioned in the case of R1, and where at least one of the substituents X1, X2 and X3 represents in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, each of which has 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, or represents straight-chain or branched alkylsulphonyl having 1 to 3 carbon atoms, or represents divalent dioxyalkylene having 1 to 3 carbon atoms which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 3 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, furthermore represents hydroxycarbonyl, in each case straight-chain or branched alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 3 carbon atoms in the alkyl moiety, cycloalkyloxycarbonyl having 3, 5 or 6 carbon atoms in the cycloalkyl moiety, or amino or aminocarbonyl, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable amino substituents in each case being:

in each case straight-chain or branched alkyl having 1 to 3 carbon atoms, halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 halogen atoms, alkoxyalkyl or alkylcarbonyl, each of which has 1 to 3 carbon atoms in the individual alkyl moieties, or phenylcarbonyl, phenylsulphonyl, phenylaminocarbonyl or phenylmethylsulphonyl, each of which is optionally monnsubstituted to trisubstituted by identical or different substituents in the phenyl moiety, suitable phenyl substituents in each case being those mentioned in the case of R1;

X1, X2 and X3 furthermore represent phenyl, phenylthio, phenylsulphinyl,phenylsulphonyl, phenylsulphonyloxy, phenylcarbonyl, phenyloxycarbonyl, phenylthiomethylsulphonyl or phenylazo, each of which is optionally monosubstituted to trisubstituted in the phenyl moiety by identical or different substituents, suitable phenyl substituents in each case being those mentioned in the case of R1.

5. Process for the preparation of new substituted fused imidazoles of the general formula (I) (I) in which R1 represents hydrogen or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkoxy and aryl, R2 represents hydroxyl, cyano or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)aryl-carbonyl, (hetero)aryloxycarbonyl, (hetero)arylcarbonyloxy and (hetero)arylaminocarbonyl-aminocarbonyloxy, R3 represents cyano, halogen or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkenyloxy, alkoxy, alkinyloxy, amino, aminocarbonyl and aryl, A1, A2, A3 and A4 in each case represent N(nitrogen), N-CHR1R2 or CX the hetero-fused ring having at least one, but not more than two, nitrogen atoms simultaneously and all positional isomers being possible, so that CX1, CX2, CX3 exist in the case of one nitrogen atom and CX1 and CX2 exist in the case of two nitrogen atoms, and, when either A1, A2, A3 or A4 represent N-CHR1R2, the imidazole ring exists only in monosubstituted form, where, X1, X2 and X3 in each case independently of one another represent hydrogen, halogen, cyano, nitro or a straight-chain or branched, in each case optionally unsubstituted or substituted, radical from the series consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl and cycloalkyl, or represents hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, or represents in each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substituents X1, X2 or X3 represents halogenoalkyl, halogenoalkoxy, halogenoallcylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkylsulphonyl, or represents optionally substituted fused dioxyalkylene, or represents hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbnoyl, or represents in each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, characterized in that 1H-substituted hetero-fused imidazoles of the formula (II) (II) in which A1, A2, A3, A4 and R3 have the abovementioned meanings are reacted with compounds of the formula (III) (m) in which M represents a suitable leaving group and R1 and R2 have the abovementioned meanings, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.

6. Herbicidal compositions, characterized in that they comprise at least one substituted hetero-fused imidazole of the formula (I) according to Claims 1 to 5.

7. Method of combating undesirable 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 environment.

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

9. Process for the preparation of herbicidal and insecticidal compositions, characterized in that substituted hetero-fused 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 hetero-fused imidazoles of the general formula (I) according to Claims 1 to 5 for combinating animal pests.