DE19719590A1 - Substituted nitrogen heterocycles, processes for their preparation and their use as pesticides - Google Patents

Abstract

The invention relates to substituted heterocyclic nitrogens, methods for producing same and their use as pest control agent. In formula (I), A represents CH and D represents N<+>R, A represents nitrogen and D represents N<+>R, or A represents N<+>R and D represents nitrogen, R represents -CR<4>R<5>-E-R<6>, Q<n>- is an inorganic or organic anion, n is 1, 2, 3 or 4 and R<1>-R<6>, E, X, Y and Z have the meanings assigned to them in the description. The invention also relates to a method for producing said heterocyclic nitrogens and their use as pest control agents.

Description

The invention relates to new substituted pyridines and pyrimidines and the like derived condensed systems, processes for their production and their Use as pesticides and fungicides.

It is already known that certain 4-amino and 4-alkoxy heterocycles Show fungicidal, acaricidal and insecticidal activity (e.g. WO-A-93/19 050, DE-A-43 43 250, WO-A-95/07 890, WO-A-94/21 613). The biological effect of these compounds, however, especially at low application rates and Concentrations, not satisfactory in all application examples.

New positively charged nitrogen heterocycles of the general formula I have been found

where the radicals and groups are as defined below, which is very good with good plant tolerance and favorable warm-blood toxicity to control animal pests, such as insects, arachnids, Nematodes, helminths and mollusks, to combat endo- and Ectoparasites in the veterinary field and for the control of Harmful fungi are suitable.  

The invention therefore relates to compounds of the general formula I in which

• 1) A CH and DN⁺R
  or
  A nitrogen and DN⁺R
  or
  AN⁺R and D means nitrogen, in which
  R for
  stands;
• 2) Q ^{n- is} any inorganic or organic anion, where n is 1, 2, 3 or 4;
• 3) R ^{1 is} hydrogen, halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl or (C ₃ -C ₅ ) cycloalkyl;
• 4) R ² and R ^{3 are} identical or different and are each hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) -Halogenalkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₂ -C ₄ ) -haloalkynyl, (C ₁ -C ₈ ) -trialkylsilylalkynyl, preferably dimethyl- (C ₁ -C ₈ ) -alkyl-silyl- alkynyl, (C ₁ -C ₄₎ alkoxy, (C ₁ -C ₄₎ - haloalkoxy, (C ₁ -C ₄₎ alkoxy- (C ₁ -C ₄₎ alkyl, (C ₁ -C ₄₎ - Haloalkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) - haloalkoxy- (C ₁ -C ₄ ) - haloalkyl, amino, monosubstituted amino, disubstituted amino, halogen, hydroxy, (C ₁ -C ₄ ) hydroxyalkyl, (C ₁ -C ₄ ) alkanoyl, (C ₁ -C ₄ ) alkanoyl- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkanoyl, (C ₃ -C ₅ ) cycloalkyl, (C ₃ -C ₅ ) halocycloalkyl, cyano, (C ₁ -C ₄ ) cyanoalkyl, nitro, (C ₁ -C ₄ ) nitroalkyl, thiocyano, (C ₁ -C ₄ ) thiocyanoalkyl, (C ₁ -C ₄ ) alkoxycarbonyl, (C ₁ -C ₄ ) alkoxycarbonyl (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkoxycarbonyl, (C ₁ -C ₄ ) - Alkylthio, (C ₁ -C ₄ ) alkylthio- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkylthio, (C ₁ -C ₄ ) alkylsulfinyl, (C ₁ -C ₄ haloalkylsulfinyl , (C ₁ -C ₄ alkylsulfonyl or (C ₁ -C ₄ ) haloalkylsulfonyl; or
  R ² and R ³ together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered isocyclic ring which, if it is a 5-ring, instead of CH _{2, represents} an oxygen or sulfur atom or which, if it is a 6-ring, can contain one or two nitrogen atoms instead of one or two CH units and which is optionally substituted by 1, 2 or 3 identical or different radicals and these radicals (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, preferably trifluoromethyl, halogen, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) haloalkoxy; or
  R ² and R ³ together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered isocyclic ring which may contain oxygen and / or sulfur instead of one or two CH ₂ groups and which is optionally substituted by 1, 2 or 3 (C ₁ -C ₄ ) alkyl groups;
• 5) XO, S (O) _q with q = 0, 1 or 2, NR ⁷ or CR ⁸ R ⁹ , where R ^{7 is} hydrogen and R ⁸ and R ⁹ independently of one another are hydrogen or (C ₁ -C ₄ ) -Alkyl mean.
• 6) YZ together means a (C ₁ -C ₂₀ ) hydrocarbon radical which is unbranched or branched and in which one or more, preferably up to three, CH ₂ by heteroatom units such as O, NR ¹⁰ , S, SO, SO ₂ or SiR ¹¹ R ¹² can be replaced, where R ^{10 is} hydrogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -acyl, and R ¹¹ and R ¹² , which are the same or different, independently of one another (C ₁ -C ₄ ) alkyl, phenyl or substituted phenyl, and wherein this (C ₁ -C ₂₀ ) hydrocarbon radical with the possible above-mentioned variations optionally with one or more, preferably up to three identical or different radicals from the series
  (C ₁ -C ₇ ) alkyl,
  (C ₂ -C ₄ ) alkenyl,
  (C ₂ -C ₄ ) alkynyl,
  (C ₃ -C ₇ ) cycloalkyl,
  (C ₃ -C ₇ ) cycloalkenyl,
  Halogen,
  Halogen (C ₁ -C ₄ ) alkyl,
  Halogen (C ₁ -C ₄ ) alkoxy,
  Hydroxy and
  (C ₁ -C ₄ ) acyl is substituted; or, if not covered by the above definitions,
• 7) Y is a bond or a divalent hydrocarbon chain with 1 to 6 carbon atoms, optionally with one or more, preferably up to three identical or different radicals from the series
  (C ₁ -C ₇ ) alkyl,
  (C ₂ -C ₄ ) alkenyl,
  (C ₃ -C ₇ ) alkynyl,
  (C ₃ -C ₇ ) cycloalkyl,
  (C ₃ -C ₇ ) cycloalkenyl,
  Halogen,
  Halogen (C ₁ -C ₄ ) alkyl,
  Halogen (C ₁ -C ₄ ) alkoxy,
  Hydroxy and
  (C ₁ -C ₄ ) acyl is substituted; and
• 8) Z means aryl or O-aryl, where aryl is preferably a naphthyl or phenyl group, which may have one or more, preferably up to five, in particular up to three identical or different radicals from the series
  Halogen,
  (C ₃ -C ₈ ) cycloalkyl,
  (C ₃ -C ₈ ) cycloalkenyl,
  Phenoxy,
  substituted phenoxy,
  Phenylthio,
  substituted phenylthio,
  Phenyl,
  substituted phenyl,
  NO ₂ ,
  Acetoxy,
  Hydroxy,
  Cyano,
  SiR ¹⁴ R ¹⁵ R ¹⁶ ,
  O-SiR ¹⁴ R ¹⁵ R ¹⁶
  NR ¹⁷ R ¹⁸
  S (O) R ¹ 9,
  SO ₂ R ¹⁹ ,
  (C ₁ -C ₁₂ ) alkyl,
  (C ₂ -C ₁₂ ) alkenyl,
  (C ₁ -C ₁₂ ) alkoxy and
  (C ₁ -C ₁₂ ) alkylthio is substituted; and
  R ¹³ (C ₁ -C ₇ ) alkyl, halogen (C ₁ -C ₇ ) alkyl, (C ₃ -C ₇ ) cycloalkyl, halogen (C ₃ -C ₇ ) cycloalkyl, (C ₁ - C ₇ ) alkoxy, phenyl or substituted phenyl;
  R ¹⁴ , R ¹⁵ and R ^{16 are} identical or different and independently of one another are (C ₁ -C ₄ ) alkyl, phenyl and / or substituted phenyl;
  R ¹⁷ and R ^{18 are} identical or different and independently of one another are hydrogen, (C ₁ -C ₄ ) -alkyl and / or (C ₁ -C ₄ ) -acyl;
  R ^{19 represents} (C ₁ -C ₁₀ ) alkyl, phenyl or substituted phenyl;
  wherein in (C ₁ -C _{1 2)} alkyl, (C ₁ -C ₁₂₎ alkoxy, (C ₁ -C ₁₂₎ alkylthio and (C ₂ -C ₁₂₎ alkenyl, optionally one or more, preferably up to 3 CH ₂ groups are replaced by heteroatom units such as O, S, SO, SO ₂ , NR ¹⁰ or SiR ^{11 '} R ^12' ; R ^{10 '} , R ^11' and R ^{12 '} have the same meaning as R ¹⁰ , R ¹¹ , R ¹² ; the (C ₁ -C ₁₂ ) -alkyl radical with or without the abovementioned variations also with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different of the radicals from the series halogen, halogen- (C ₁ -C ₄ ) alkoxy, hydroxy, (C ₃ -C ₈ ) cycloalkyl, (C ₃ -C ₈ ) cycloalkenyl, (C ₁ -C ₄ ) acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, Phenylthio and substituted phenylthio may be substituted; in the (C ₁ -C ₇ ) alkoxy and (C ₁ -C ₇ ) alkylthio radicals one or more, preferably up to three, CH ₂ groups may be replaced by O and these radicals may be replaced by one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals from the series halogen, phenyl, substituted phenyl, (C ₃ -C ₈ ) cycloalkyl, (C ₃ -C ₆ ) cycloalkenyl, phenoxy and substituted phenoxy are substituted; or if not covered by the above definitions,
• 9) Y is a bond or a divalent hydrocarbon chain with 1 to 6 carbon atoms, preferably methylene, which may or may not have one or more, preferably up to three, identical or different radicals from the series
  (C ₁ -C ₇ ) alkyl,
  (C ₂ -C ₄ ) alkenyl,
  (C ₃ -C ₇ ) alkynyl,
  (C ₃ -C ₇ ) cycloalkyl,
  (C ₃ -C ₇ ) cycloalkenyl,
  Halogen,
  Halogen (C ₁ -C ₄ ) alkyl,
  Halogen (C ₁ -C ₄ ) alkoxy,
  Hydroxy and
  (C ₁ -C ₄ ) acyl is substituted; and
• 10) Z is (C ₃ -C ₈ ) cycloalkyl or (C ₅ -C ₈ ) cycloalkenyl, where a CH ₂ group of the carbocycle can be replaced by NR ²⁰ ;
  R ²⁰ denotes phenyl or substituted phenyl and the (C ₃ -C ₈ ) cycloalkyl or (C ₅ -C ₈ ) cycloalkenyl radical, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number same or different residues from the series
  (C ₁ -C _{1 8} ) alkyl,
  (C ₃ -C ₈ ) cycloalkyl,
  (C ₃ -C ₈ ) cycloalkoxy,
  (C ₂ -C _{1 8} ) alkenyl,
  (C ₂ -C _{1 8} ) alkynyl,
  (C ₁ -C _{1 2} ) alkoxy,
  (C ₁ -C _{1 2} ) alkanoyloxy,
  Formyl,
  (C ₂ -C _{1 2} ) acyl,
  (C ₁ -C ₁₂ ) alkyloxycarbonyl,
  SiR ²¹ R ²² R ²³
  NR ²⁴ R ²⁵ ,
  Hydroxyl,
  Halogen,
  Aryl,
  Heteroaryl,
  OAryl,
  OHeteroaryl,
  (C ₁ -C ₁₈ ) alkanediyldioxy,
  (C ₁ -C ₁₃ ) alkyl oximino and
  (C ₂ -C ₁₈ ) alkylidene are substituted and, if not covered by the above definitions, in the (C ₁ -C ₁₈ ) -, (C ₂ -C ₁₈ ) -, (C ₁ -C ₁₂ ) - , (C ₂ -C ₁₂ ) and (C ₁ -C ₁₃ ) hydrocarbon radicals one or more, preferably up to three, CH ₂ groups by heteroatom units, such as O, NR ^{10 ''} , or SiR ^{11 '"} R ^12" can be replaced and these heteroatom units are preferably not adjacent, where R ^{10 "} , R ^11" and R ^{12 "have} the same meaning as R ¹⁰ , R ¹¹ , R ¹² and also 3 to 6 carbon atoms of these hydrocarbon radicals can form a cycle and these hydrocarbon radicals with or without these variations, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different hydroxyl radicals, Halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio are substituted;
  Heteroaryl can be unsubstituted or can be provided with up to three, in the case of fluorine also up to the maximum number, identical or different substituents;
  Aryl has the meanings as under (8);
  R ²⁴ and R ^{25 are the} same or different and are independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) acyl, (C ₃ -C ₆ ) cycloalkyl, phenyl and substituted phenyl and R ²¹ , R ²² , R ^{23 are the} same or different and independently of one another are (C ₁ -C ₁₈ ) alkyl, (C ₁ -C ₁₈ ) alkoxy, (C ₃ -C ₈ ) cycloalkyl and aryl, where in the (C ₁ -C ₁₈ ) hydrocarbon radicals several, preferably up to three, non-adjacent CH ₂ groups can be replaced by oxygen and 3 to 6 C atoms of these hydrocarbon radicals can form a cycle, two of them also the carbon residues bonded to the silicon (for example R ¹ and R ²² ) can together form a cycle, as a result of which the silicon atom is then a ring atom of this cycle and moreover these (C ₁ -C ₁₈ ) hydrocarbon residues with or without the variations, optionally with one or more in the case of halogen up to the maximum number of the same or different radicals the series halogen, haloalkyl, cycloalkyl, may be substituted, where the substituents on the cycloalkyl or cycloalkenyl radicals defined under (10) may be cis or trans with respect to the unit (XY) and in the event that the cycloalkyl group is the Is cyclohexyl radical and the above-mentioned units occupy the 1,4-position, the cis configuration is preferred; or
• 11) Y is a bond; and
• 12) Z (a) denotes a group of the formula II
  wherein X ^{1 is} independently sulfur or oxygen;
  R ^{z represents} hydrogen, (C ₁ -C ₄ ) alkyl, trifluoromethyl or (C ₁ -C ₄ ) alkoxy; or
  R ^{y is} alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals listed may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different radicals and in the alkyl mentioned Alkenyl or alkynyl radicals one or more, preferably up to three, non-adjacent saturated carbon units by a carbonyl group or by heteroatom units, such as oxygen, S (O) _x , with x = 0, 1 or 2, NR ²⁶ or SiR ²⁷ R ²⁸ can be replaced, where R ^{26 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl and R ²⁷ and R ^{28 is} (C ₁ -C ₄ ) alkyl, preferably methyl; and in which, in addition, 3 to 12 atoms of these hydrocarbon radicals, optionally modified as above, can form a cycle, and these hydrocarbon radicals with or without the stated variations, optionally with one or more, preferably up to three, in the case of fluorine, up to the maximum number on identical or different radicals from the series halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyloxycarbonyl, cycloalkoxyalkoxy, carbonyl, alkoxyloxyyloxycarbonyl Heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, arylsulfanoyloxy, hydroxyls in the cycloaliphatic, aromatic or heterocyclic ring systems under the just mentioned substituents are unsubstituted or can be provided with up to three, in the case of fluorine also up to the maximum number of identical or different substituents, or R ^y and R ^z together form a three to eight form a membered ring system which is spirocyclically linked to the ring system containing the heteroatoms X ¹ and in which one or two CH ₂ groups, preferably a CH ₂ group, are formed by heteroatom units such as oxygen, S (O) _n with n = 0, 1 or 2 or NR ²⁹ can be replaced, where R ^{29 is} hydrogen, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals are unsubstituted or with up to three, in the case of fluorine can also be provided up to the maximum number of identical or different substituents, and the ring system formed from R ^y and R ^{z is} unsubstituted or with up to three, but preferably one, substituent nten can be provided and these substituents are the same or different and each represents alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthyl, alkoxycarbonyl or trialkyl where the cycloaliphatic, aromatic or heterocyclic ring systems can be unsubstituted under the just mentioned substituents or can be provided with up to three in the case of fluorine up to the maximum number of identical or different substituents, or the ring system formed from R ^y and R ^z with a further benzene ring or cyclohexane ring together forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system and the benzene ring in these condensed systems unsubstituted or with up to three, in the case of fluorine also up to Maximum number of identical or different substitutes can be provided;
  in particular those groups of the formula II for which
  R ^{y is} (C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals listed are unsubstituted or with bis to three, in the case of fluorine also up to the maximum number of identical or different radicals and in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, non-adjacent saturated carbon units by a carbonyl Group or by heteroatom units, such as oxygen, S (O) _x , with x = 0, 1 or 2, NR ²⁶ or SiR ²⁷ R ²⁸ can be replaced, where R ^{26 is} hydrogen, (C ₁ -C ₄ ) alkyl , (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl and R ²⁷ and R ^{28 are} (C ₁ -C ₄ ) alkyl, preferably methyl, and in which in addition 3 to 12 atoms these hydrocarbon radicals, optionally modified as above, can form a cycle, and these hydrocarbon radicals with or without the specified variations, if appropriate s with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals from the series halogen, aryl, aryloxy, arylthio, (C ₃ -C ₈ ) - cycloalkoxy, (C ₃ -C ₈ ) -Cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (C ₁ -C ₁₂ ) alkanoyl, (C ₃ -C ₈ ) cycloalkanoyl, (C ₂ -C ₁₂ ) haloalkanoyl, aroyl, aryl- (C ₁ -C ₄ ) - alkanoyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkanoyl, heterocyclyl- (C ₁ - C ₄ ) -alkanoyl, (C ₁ -C ₁₂ ) -alkoxycarbonyl, (C ₁ - C ₁₂ ) - haloalkoxycarbonyl, (C ₃ -C ₈ ) -cycloalkoxycarbonyl, (C ₃ -C ₈ ) - cycloalkyl- (C ₁ -C ₄ ) -alkoxycarbonyl-, aryl- (C ₁ -C ₄ ) - alkoxycarbonyl, heterocyclyl - (C ₁ -C ₄ ) alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, (C ₁ -C ₁₂ ) alkanoyloxy, (C ₂ -C ₁₂ ) haloalkanoylalkoxy, (C ₃ -C ₈ ) - cycloalkanoyloxy, (C ₃ -C ₈ ) -Cycloalkyl- (C ₁ -C ₄ ) alkanoyloxy, aroyloxy, aryl- (C ₁ -C ₄ ) alkanoyloxy, heterocyclyl- (C ₁ -C ₄ ) alkanoyloxy, (C ₁ -C ₁₂ ) alkylsulfonylox y, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro can be substituted, the cycloaliphatic, aromatic or heterocyclic ring systems being unsubstituted under the just mentioned substituents or provided with up to three, in the case of fluorine also up to the maximum number of identical or different substituents can, or R ^y and R ^z together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the heteroatoms X ¹ and in which one or two CH ₂ groups, preferably a CH ₂ group, by heteroatom units such as oxygen, S (O) _{n can be replaced} with n = 0, 1 or 2 or NR ²⁹ , where R ^{29 is} hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -alkoxy, (C ₁ -C ₈ ) -alkanoyl, benzoyl, aryl or heteroaryl, it being possible for the benzoyl, aryl or heteroaryl radicals to be unsubstituted or provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents NEN and the ring system formed from R ^y and R ^z can be unsubstituted or can be provided with up to three, but preferably one, substituent and these substituents are identical or different and are each (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) alkylthio, (C ₃ -C ₈ ) cycloalkyl, (C ₃ -C ₈ ) cycloalkoxy, (C ₃ -C ₈ ) -cycloalkylthio, aryl, aryloxy, arylthio, aryl- (C ₁ -C ₄ ) -alkyl, aryl- (C ₁ -C ₄ ) -alkoxy, aryl- (C ₁ -C ₄ ) -alkylthio, heterocycyl, heterocyclyloxy , Heterocyclylthio, (C ₁ -C ₈ ) -trialkylsilyl, preferably (C ₁ -C ₈ ) -alkyldimethylsilyl or (C ₁ -C ₈ ) -alkoxycarbonyl, the cycloaliphatic, aromatic or heterocyclic ring systems under the just mentioned substituents and may be substituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents, or the ring system formed from R ^y and R ^z with a further benzene ring or cyclohexane ring together forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decahydronaphthalene or benzocycloheptane system and the benzene ring in these condensed systems unsubstituted or with up to three, in the case of fluorine also up to the maximum number may be provided on the same or different substituents, wherein among the compounds for which the carbon atom between the heteroatoms X ¹ carries only the substituent R ^y , the substituents X and R ^{y are} preferably cis to one another;
  R ^{z represents} hydrogen, (C ₁ -C ₄ ) alkyl, trifluoromethyl or (C ₁ -C ₄ ) alkoxy; or
  b) is a group of the formula III
  wherein
  Y ¹ , Y ² and Y ³ independently of one another a group of the formula -O-, -CO-, -CNR ³⁰ -, -S (O) _r - with r = 0, 1 or 2, -N (O) _l R ³⁰ - with l = 0 or 1 or a group of the formula CR ³¹ R ³² ; or
  Y ¹ or Y ^{3 are} in place of a direct bond, where
  R ^{30 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) haloalkenyl, (C ₂ -C ₄ ) Alkynyl, (C ₂ -C ₄ ) haloalkynyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₄ ) Haloalkylthio, (C ₁ -C ₄ ) alkanoyl, (C ₂ -C ₄ ) haloalkanoyl, (C ₃ -C ₅ ) cycloalkyl, (C ₁ -C ₄ ) alkylsulfonyl, (C ₁ -C ₄ ) Haloalkylsulfonyl, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxycarbonyl;
  R ³¹ and R ³² independently of one another are hydrogen, hydroxy, halogen, cyano, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄₎ haloalkenyl, (C ₂ -C ₄₎ -alkynyl, (C ₂ -C ₄₎ - haloalkenyl, (C ₃ -C ₅₎ cycloalkyl, (C ₁ -C ₄₎ alkanoyl, (C ₁ -C ₄ ) - haloalkanoyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkylthio or (C ₁ -C ₄ ) haloalkylthio;
  m ^{1 represents} 0, 1, 2, 3 or 4, preferably 1 or 2;
  n ^{1 represents} 0, 1, 2, 3 or 4, preferably 1 or 2;
  Z ^{1 is} a direct bond, NR ³³ , O, S (O) _s with s = 0, 1 or 2, OSO ₂ , SO ₂ O, NR ³⁴ SO ₂ , SO ₂ NR ³⁵ , SiR ³⁶ R ³⁷ or
  means
  in which
  R ³⁶ and R ^{37 are} (C ₁ -C ₄ ) alkyl or phenyl, preferably methyl;
  U is a direct bond, NR ³⁸ or O;
  W represents oxygen or sulfur, preferably oxygen;
  V is a direct bond, NR ³⁹ or oxygen, where R ³³ , R ³⁴ , R ³⁵ , R ³⁸ and R ^{39 are the} same or different and each represents hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
  R ^q are independent substituents and are halogen, cyano, nitro, (C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, (C ₃ -C ₈ ) -Cycloalkyl, (C ₄ -C ₈ ) -cycloalkenyl means and in the latter 5 radicals one or more, preferably up to three non-adjacent saturated carbon units by a carbonyl group or by heteroatom units, such as oxygen, S (O) _x with x = 0, 1 or 2, NR ⁴⁰ or SiR ⁴¹ R ⁴² can be replaced and these last 5 residues with or without the specified variations, optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number identical or different radicals D ¹ R ⁴³ may be substituted, or
  R ^q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine up to the maximum number of identical or different radicals D ² R ⁴⁴ , or two adjacent radicals
  Z ¹ -R ^q together with the C atoms carrying these can form a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group of O, S and N and which is unsubstituted or by one or more radicals from the Group of halogen, (C ₁ -C ₄ ) alkyl and oxo is substituted, or
  R ³³ , R ³⁵ or R ^39, independently of one another, can form a 4- to 8-membered ring system with the R ^q located on Z, in which one or two CH ₂ groups, preferably a CH ₂ group, are formed by heteroatom units such as oxygen , S (O) _{t can be replaced} with t = 0, 1 or 2 or NR ⁴⁵ ,
  in which
  R ^{40 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl;
  R ⁴¹ and R ⁴² independently of one another are (C ₁ -C ₄ ) -alkyl, preferably methyl;
  D ¹ and D ^{2 are} each independently and a direct bond, oxygen, S (O) _k , SO ₂ O, OSO ₂ , CO, OCO, COO, NR ⁴⁶ , SO ₂ NR ⁴⁶ , NR ⁴⁶ SO ₂ , ONR ⁴⁶ , NR ⁴⁶ O, NR ⁴⁶ CO, CONR ⁴⁶ or SiR ⁴⁷ R ⁴⁸ , and k = 0, 1 or 2, where
  R ^{46 is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
  R ⁴⁷ and R ⁴⁸ independently of one another are (C ₁ -C ₄ ) -alkyl;
  R ⁴³ and R ⁴⁴ independently of one another hydrogen, cyano, nitro, halogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) -Halogenalkenyl, (C ₂ -C ₈ ) alkynyl, (C ₂ -C ₈ ) - haloalkynyl, (C ₁ -C ₈ ) alkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) - Haloalkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) alkylthio- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) haloalkylthio- (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₈ ) -cycloalkyl, (C ₄ -C ₈ ) -cycloalkenyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkyl, (C ₄ -C ₈ ) - Cycloalkenyl- (C ₁ -C ₄ ) -alkyl, aryl, heterocyclyl, aryl- (C ₁ -C ₄ ) -alkyl or heterocyclyl- (C ₁ -C ₄ ) -alkyl, wherein in the latter 8 residues the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁴⁹ , or
  R ⁴³ and R ^{44 together} on the same C atom represent an oxo group,
  in which
  R ^{49 is} (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro or halogen ;
  R ^{45 is} hydrogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkylthio, (C ₃ -C ₅ ) -Cycloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, (C ₁ -C ₄ ) alkanoyl, (C ₂ -C ₄ ) haloalkanoyl, (C ₂ -C ₄ ) -Alkoxyalkyl, phenyl- (C ₁ -C ₄ ) -alkyl or phenyl and the phenyl groups may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁵⁰ , where
  R ^{50 represents} (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkylthio, halogen or cyano;
  or, if not covered by the above definitions,
  c) is a group of the formula IV
  wherein
  Y ^{4 is} direct bond or CH ₂ ;
  Z ^{2 represents} oxygen, NR ⁵¹ , S (O) _m with m = 0, 1 or 2;
  R ^u and W ¹ -R ^{t are} substituents of the heteroaliphatic ring system, where
  R ^{u is} hydrogen, halogen, cyano, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) haloalkenyl, (C ₂ -C ₄ ) alkynyl, (C ₂ -C ₄ ) haloalkynyl, (C ₃ -C ₆ ) cycloalkyl, (C ₄ -C ₆ ) cycloalkenyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkanoyloxy, (C ₁ -C ₄ ) haloalkanoyloxy, (C ₁ -C ₄ ) alkylthio or (C ₁ -C ₄ ) haloalkylthio;
  W ¹ denotes direct bond, oxygen, -NR ⁵² -, -CO-, -COO-, CONR ⁵² -, sulfur, -C = N-, -C = NO- or -NR ⁵² O-;
  R ^t denotes hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl and in the latter 5 radicals one or more, preferably up to three, non-adjacent saturated carbon units through a carbonyl group or through heteroatom units, such as oxygen, S (O) _{x can be replaced} with x = 0.1 or 2, NR ⁵³ or SiR ⁵⁴ R ⁵⁵ , and these last 5 residues with or without the specified variations, optionally with one or more, preferably up to three, in the case of fluorine up to Maximum number of identical or different radicals D ³ R ⁵⁶ can be substituted, or
  R ^t can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ⁴ R ⁵⁷ , or
  R ^u and R ^t together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the heteroatoms Y ⁴ and Z ² and in which one or two CH ₂ groups, preferably a CH ₂ group, are formed by a hetero atom Units such as oxygen, S (O) _n with n = 0.1 or 2, or NR ⁵⁸ can be replaced
  in which
  R ^{51 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) haloalkenyl, (C ₂ -C ₄ ) Alkynyl, (C ₂ -C ₄ ) haloalkynyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkanoyl, (C ₂ -C ₄ ) haloalkanoyl, (C ₁ -C ₄ ) -Alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkylthio- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) - Alkylsulfonyl, (C ₁ -C ₄ ) -haloalkylsulfonyl, phenylcarbonyl, phenyl- (C ₁ -C ₄ ) -alkyl or phenyl, the latter 3 radicals being unsubstituted or with up to three, in the case of fluorine also up to Maximum number of identical or different substituents R ⁵⁹ can be substituted, or
  R ^{51 means} CONR ⁶⁰ R ⁶¹ , wherein
  R ⁶⁰ and R ⁶¹ independently of one another are hydrogen, (C ₁ -C ₄ ) -alkyl or phenyl, where the phenyl group can be unsubstituted or substituted by up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁶² , and
  R ⁶² and R ⁵⁹ independently of one another (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) - alkylthio or halogen;
  R ^{52 represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
  R ^{53 represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl;
  R ⁵⁴ and R ⁵⁵ independently of one another are (C ₁ -C ₄ ) -alkyl, preferably methyl;
  R ^{58 is} hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, the latter 3 radicals being unsubstituted or having up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁶³ ;
  R ⁶³ (C ₁ -C ₄₎ -alkyl, (C ₁ -C ₄₎ -haloalkyl, (C ₁ -C ₄₎ alkoxy, (C ₁ -C ₄₎ - may be haloalkoxy, cyano, nitro or halogen, and the ring system formed from R ^u and R ^t can be unsubstituted or can be provided with up to three, but preferably one, substituent D ⁵ R ⁶⁴ , or the ring system formed from R ^u and R ^t together with another benzene ring or cyclohexane ring forms a condensed ring system , preferably the indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system and the benzene ring in these condensed systems unsubstituted or with up to three, in the case of fluorine also up to the maximum number of identical or different substituents D ⁶ R ⁶⁵ can be provided, wherein
  D ³ , D ⁴ , D ⁵ and D ^{6 are} each independently and a direct bond, oxygen, S (O) _k , SO ₂ O, OSO ₂ , 99999 00070 552 001000280000000200012000285919988800040 0002019719590 00004 99880 CO, OCO, COO, SO ₂ NR ⁶⁶ , NR ⁶⁶ SO ₂ , NR ⁶⁶ O, ONR ⁶⁶ , NR ⁶⁶ , NR ⁶⁶ CO, CONR ⁶⁶ or SiR ⁶⁷ R ⁶⁸ mean and k = 0, 1 or 2; and
  R ⁵⁶ , R ⁵⁷ , R ⁶⁴ and R ⁶⁵ each independently of one another hydrogen, cyano, nitro, halogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₂ -C ₈ ) - Alkenyl, (C ₂ -C ₈ ) haloalkenyl, (C ₂ -C ₈ ) alkynyl, (C ₂ -C ₈ ) haloalkynyl, (C ₁ -C ₈ ) alkoxy (C ₁ -C ₄ ) alkyl , (C ₁ -C ₈ ) haloalkoxy (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) alkylthio (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) haloalkylthio, ( C ₁ -C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ - C ₈ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkyl, ( C ₄ -C ₈ ) - Cycloalkenyl- (C ₁ -C ₄ ) -alkyl, aryl, heterocyclyl, aryl- (C ₁ -C ₄ ) -alkyl or heterocyclyl- (C ₁ -C ₄ ) -alkyl, where in the latter 8 radicals, the cycloaliphatic, aromatic or heterocyclic ring systems are unsubstituted or can be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁶⁹ , where
  R ⁶⁶ are independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl and
  R ⁶⁷ and R ⁶⁸ independently of one another are (C ₁ -C ₄ ) -alkyl, and
  R ⁶⁹ independently of one another (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro, halogen, Can be (C ₁ -C ₄ ) alkanoyl or (C ₂ -C ₄ ) haloalkanoyl, or two of the radicals
  R ⁵⁶ , R ⁵⁷ , R ⁶⁴ , R ⁶⁵ , R ⁶⁹ , which are located on the same C atom, together and each independently represent an oxo group;
  in particular those groups of the formula IV for which
  R ^{t is} hydrogen, (C ₁ -C ₈ ) alkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl or (C ₄ -C ₈ ) -Cycloalkenyl and in the latter 5 radicals one or more, preferably up to three non-adjacent saturated carbon units by a carbonyl group or by heteroatom units, such as oxygen, S (O) _x with x = 0, 1 or 2, NR ⁵³ or SiR ⁵⁴ R ⁵⁵ can be replaced, and these latter 5 residues with or without the specified variations, optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number of identical or different residues D ³ R ⁵⁶ may be substituted, or
  R ^t can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ⁴ R ⁵⁷ , or
  R ^u and R ^t together form a five- or six-membered ring system which is preferably spirocyclically linked to the ring system containing the heteroatoms Y ⁴ and Z ² and in which a CH ₂ group is formed by heteroatom units such as oxygen, S ( O) _{n can be replaced} with n = 0, 1 or 2 or NR ⁵⁸ , where
  R ^{53 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl and
  R ⁵⁴ and R ⁵⁵ independently of one another are (C ₁ -C ₄ ) -alkyl, preferably methyl;
  R ^{58 is} hydrogen (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkanoyl, benzoyl, aryl or heteroaryl, the latter 3 radicals being unsubstituted or with up to three, in the case of fluorine also up to the maximum number may be provided on the same or different substituents R ⁶³ , and
  R ⁶³ (C ₁ -C ₄₎ -alkyl, (C ₁ -C ₄₎ -haloalkyl, (C ₁ -C ₄₎ alkoxy, (C ₁ -C ₄₎ - may be haloalkoxy, cyano, nitro or halogen, and the ring system formed from R ^u and R ^t can be unsubstituted or can be provided with up to three, but preferably one, substituent D ⁵ R ⁶⁴ , or the ring system formed from R ^u and R ^t together with a further benzene ring or cyclohexane ring is a condensed ring system forms, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system and the benzene ring in these condensed systems unsubstituted or with up to three, in the case of fluorine also up to the maximum number of the same or different Substituents D ⁶ R ⁶⁵ can be provided, wherein among the compounds for which the carbon atom between Y ⁴ and Z ² with Y = CH ₂ only carries the substituents W ¹ -R ^t , the substituents X and W ^1- R ^t are cis to one another - are permanent;
  D ³ , D ⁴ , D ⁵ and D ^{6 are} each independently and a direct bond, oxygen, S (O) _k , SO ₂ O, OSO ₂ , CO, OCO, COO, SO ₂ NR ⁶⁶ , NR ⁶⁶ SO ₂ , NR ⁶⁶ O, ONR ⁶⁶ , NR ⁶⁶ , NR ⁶⁶ CO or CONR ⁶⁶ and where k = 0, 1 or 2,
  R ⁶⁶ independently of one another are hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkanoyl or (C ₃ -C ₅ ) -cycloalkyl and
  R ⁵⁶ , R ⁵⁷ , R ⁶⁴ and R ⁶⁵ each independently represent hydrogen, cyano, nitro, halogen, preferably fluorine, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, aryl, heterocyclyl, in the latter 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems are unsubstituted or can be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁶⁹ , where
  R ^{69 is} independently (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro, halogen can, or two of the leftovers
  R ⁵⁶ , R ⁵⁷ , R ⁶⁴ , R ⁶⁵ , R ⁶⁹ , which are located on the same C atom, together and each independently represent an oxo group;
• 13) R ^{4 represents} hydrogen, halogen, (C ₁ -C ₄ ) alkyl;
• 14) R ^{5 is} hydrogen, halogen, CN, nitro, (C ₁ -C ₄ ) alkoxycarbonyl, (C ₁ -C ₄ ) alkylcarbamoyl, di- (C ₁ -C ₄ ) alkylcarbamoyl, (C ₁ -C ₈ ) -Alkoxy, (C ₁ -C ₈ ) -alkyl, (C ₂ -C ₈ ) -alkenyl, (C ₂ -C ₈ ) -alkynyl, aryl or (C ₃ -C ₈ ) -cycloalkyl, where aryl is like is defined under (8) and, if not covered by the above definitions, the carbon radicals mentioned under (13) and (14) optionally with one or more, preferably up to three, in the case of halogen up to the maximum number, the same or different Radicals from the series halogen, cycloalkyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, may be substituted;
  R ^{6 is} aryl or heteroaryl, which can optionally be substituted by one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals Z ^{1 '} -R ^q' , where
  Z ¹ , a direct bond, NR ^{33 '} , O, S (O) _s with s = 0, 1 or 2, OSO ₂ , SO ₂ O, NR ^34' SO ₂ , SO ₂ NR ³⁵ ,, SiR ^{36 '} R ^{37 '} or
  means
  wherein R ^{36 '} and R ^{37' are} (C ₁ -C ₄ ) alkyl or phenyl, preferably methyl;
  U 'is a direct bond, NR ^38' or O;
  W 'represents oxygen or sulfur, preferably oxygen;
  V 'is a direct bond, NR ^39' or oxygen, where R ^{33 '} , R ^34' , R ^{35 '} , R ^38' and R ^{39 'are the} same or different and each represents hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
  R ^{q '} are mutually independent substituents and are halogen, hydroxy, cyano, nitro, (C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, (C ₃ - C ₈ ) -cycloalkyl, (C ₄ -C ₈ ) -cycloalkenyl and in the latter 5 radicals one or more, preferably up to three non-adjacent saturated carbon units by a carbonyl group or by heteroatom units, such as oxygen, S ( O) _{x can be replaced} with x = 0, 1 or 2, NR ^{40 '} or SiR ^41' R ^{42 '} and these last 5 residues with or without the specified variations, if appropriate with one or more, preferably up to three, in the case can be substituted by fluorine up to the maximum number of identical or different radicals D ^{1 '} R ^43' , or
  R ^{q '} denotes aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ^2' R ^{44 '} , or two adjacent radicals Z ^1' - R ^{q '} together with the carbon atoms bearing these can form a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group of O, S and N and which is unsubstituted or by one or more radicals from the group of Halogen, (C ₁ -C ₄ ) alkyl and oxo is substituted, or
  R ^{33 '} , R ^35' or R ^{39 '} independently of one another can form a 4- to 8-membered ring system with the R ^q ' located on Z ', in which one or two CH ₂ groups, preferably a CH ₂ group, are formed by Heteroatom units such as oxygen, S (O) _{t can be replaced} with t = 0, 1 or 2 or NR ^{45 '} ,
  in which
  R ^{40 'represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl;
  R ^{41 '} and R ^42' independently of one another are (C ₁ -C ₄ ) -alkyl, preferably methyl;
  D ^{1 '} and D ^{2' are} each independently and a direct bond, oxygen, S (O) _k , SO ₂ O, OSO ₂ , CO, OCO, COO, NR ^{46 '} , SO ₂ NR ^46' , NR ^{46 '} SO ₂ , ONR ^{46 '} , NR ^46' O, NR ^{46 '} CO, CONR ^46' or SiR ^{47 '} R ^48' mean, and k = 0, 1 or 2, wherein
  R ^{46 'is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
  R ^{47 '} and R ^48' independently of one another are (C ₁ -C ₄ ) alkyl;
  R ^{43 '} and R ^44' independently of one another are hydrogen, cyano, nitro, halogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) - haloalkenyl, (C ₂ -C ₈ ) alkynyl, (C ₂ -C ₈ ) haloalkynyl, (C ₁ -C ₈ ) - alkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) -haloalkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₈ ) -alkylthio- (C ₁ -C ₄ -alkyl, (C ₁ -C ₈ ) -haloalkylthio- (C ₁ - C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkyl, (C ₄ - alkyl or heterocyclyl- (C ₁ -C ₄₎ -alkyl, where in the latter 8 - C ₈₎ cycloalkenyl (C ₁ -C ₄₎ alkyl, aryl, heterocyclyl, aryl- (C ₁ -C ₄₎ Radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or may be provided with up to three, in the case of fluorine also up to the maximum number of identical or different substituents R ^{49 '} , or
  R ^{43 '} and R ^44' sitting on the same C atom together mean an oxo group
  in which
  R ^{49 'is} (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro or halogen ;
  R ^{45 'is} hydrogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkylthio, (C ₃ -C ₅ ) -Cycloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, (C ₁ -C ₄ ) alkanoyl, (C ₂ -C ₄ ) haloalkanoyl, (C ₂ -C ₄ ) -alkoxyalkyl, phenyl- (C ₁ -C ₄ ) -alkyl or phenyl and the phenyl groups may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ^{50 ′} , where
  R ^{50 'is} (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkylthio, halogen or cyano.

An inorganic anion is an anion of an inorganic acid, such as, for example, F⁻, Cl⁻, Br⁻, I⁻, NO ₃ ² , SO ₄ ² ⁻, HSO ₄ ⁻, PO ₄ ^3- , HPO ₄ ^2- , H ₂ PO _4- , PO ₃ ^3- or N ₃ ⁻, or a complex anion such as BF ₄ ⁻, PF ₆ ⁻ or tetraphenylborate.

An organic anion is an anion of an organic one Acid (carboxylic acid, sulfonic acid, phosphonic acid and the like) or  an aromatic or heteromatic phenolic compound. This are, for example, anions mono- or bifunctional carboxylic acids and Hydroxycarboxylic acids such as acetic acid, propionic acid, maleic acid, Succinic acid, glycolic acid, oxalic acid, fumaric acid, tartaric acid, Citric acid, salicylic acid, sorbic acid or lactic acid, as well Sulfonic acids such as p-toluenesulfonic acid, dodecylsulfonic acid or 1,5-naphthalenedisulfonic acid, or saccarin.

If A and D are part of a pyrimidine system, it is assumed that A is nitrogen and D is N⁺R. But it cannot be absolute Security can be excluded that the rest R is in the 3 position (i.e., A is N⁺R and D is nitrogen).

If Z is (C ₃ -C ₈ ) cycloalkyl or (C ₅ -C ₈ ) cycloalkenyl, it is preferably with one or more, preferably up to 3 identical or different substituents from the series (C ₁ -C ₁₂ ) alkyl, (C ₃ -C ₈₎ - cycloalkyl, (C ₃ -C ₈₎ -cycloalkyl- (C ₁ -C ₄₎ alkyl, (C ₁ -C ₈₎ -alkoxy, (C ₃ -C ₈₎ - Cycloalkoxy, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkoxy, tri- (C ₁ -C ₈ ) -alkylsilyl, preferably dimethyl- (C ₁ -C ₈ ) alkylsilyl or triethylsilyl, di- (C ₁ -C ₈ ) -alkyl- (C ₃ -C ₈ ) -cycloalkylsilyl, preferably dimethylcyclohexylsilyl, di- (C ₁ - C ₈ ) -alkyl- (phenyl- (C ₁ -C ₄ ) -alkyl) -silyl, preferably dimethyl- (phenyl- (C ₁ -C ₄ ) -alkyl) -silyl, di- (C ₁ -C ₈ ) -alkyl- (C ₁ -C ₄ ) -haloalkylsilyl, preferably dimethyl- (C ₁ -C ₄ ) -haloalkylsilyl, dimethylphenylsilyl, (C ₁ -C ₄ ) -haloalkyl, halogen, (C ₁ -C ₄ ) -haloalkoxy, Heteroaryl, phenyl, phenyl- (C ₁ -C ₄ ) alkyl, benzyloxy, benzyloxy- (C ₁ -C ₄ ) alkyl, benzylthio, phenylthio and phenoxy, it being possible for heteroaryl or phenyl to be unsubstituted or to be provided with one or two substituents in the eight last-mentioned radicals and these substituents are identical or different and are each (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₈ ) - Cycloalkyl (C ₁ -C ₄ ) haloalkyl, preferably trifluoromethyl, halogen, (C ₁ -C ₄ ) dialkylamino, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₈ ) alkoxy, (C ₁ - C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkoxy, H ₅ C ₂ -O- [CH ₂ -CH ₂ -O-] _x , 2- (tetrahydro- 2H-pyran-2-yloxy) ethoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, benzyloxy, which may contain one or two identical or different substituents from the series (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) - haloalkoxy and halogen carries, tri- (C ₁ -C ₄ ) - alkylsilylmethoxy, preferably dimethyl- (C ₁ -C ₄ ) alkylsilylmethoxy, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkoxy, 1,3-dioxolan-2-ylmethoxy, tetrahydrofuran-2-ylmethoxy and can mean tetrahydro-2H-pyran-2-ylmethoxy.

Compounds of the formula I are preferred
in which
A CH and DN⁺R
or
A represents nitrogen and DN⁺R;
Q ^{n is} an anion such as Hal⁻, NO ₃ ⁻, BF ₄ ⁻, BPh ₄ ⁻ or PF ₆ ⁻;
R ^{1 is} hydrogen, methyl, fluorine or chlorine;
R ² and R ^{3 are} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, amino, (C ₁ -C ₄ ) alkylamino, ( C ₁ -C ₄ ) dialkylamino, trimethylsilylethynyl, methoxycarbonyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or
R ² and R ³ together with the carbon atoms to which they are attached form an optionally substituted unsaturated 5- or 6-membered ring which, in the case of the 5-ring, may contain a sulfur atom instead of a CH ₂ unit; or
R ² and R ³ together with the carbon atoms to which they are attached form a saturated 5- or 6-membered ring which can contain a sulfur or an oxygen atom instead of a CH ₂ unit;
X means NH or oxygen.

Likewise preferred are compounds of formula I in which
Y is a bond or a methylene group which is optionally substituted with one or two, preferably with a (C ₁ -C ₄ ) -alkyl radical; and
Z is (C ₃ -C ₈ ) cycloalkyl or (C ₅ -C ₅ ) cycloalkenyl, it being possible for a CH ₂ group of the carbocycle to be replaced by NR ²⁰ ; R ^{20 is} phenyl or substituted phenyl and the (C ₃ -C ₈ ) cycloalkyl or (C ₅ -C ₈ ) cycloalkenyl radical, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number same or different residues from the series
(C ₁ -C ₁₈ ) alkyl,
(C ₃ -C ₈ ) cycloalkyl,
(C ₃ -C ₈ ) cycloalkoxy,
(C ₂ -C ₁₈ ) alkenyl,
(C ₂ -C ₁₈ ) alkynyl,
(C ₁ -C ₁₂ ) alkoxy,
(C ₁ -C ₁₂ ) alkanoyloxy,
Formyl,
(C ₂ -C ₁₂ ) acyl,
(C ₁ -C ₁₂ ) alkyloxycarbonyl,
SiR ²¹ R ²² R ²³ ,
NR ²⁴ R ²⁵ ,

Hydroxyl,
Halogen,
Aryl,
Heteroaryl,
OAryl,
OHeteroaryl,
(C ₁ -C ₁₈ ) alkanediyldioxy,
(C ₁ -C ₁₃ ) alkyl oximino and
(C ₂ -C ₁₈ ) alkylidene are substituted and, if not covered by the above definitions, in the (C ₁ -C ₁₈ ) -, (C ₂ -C ₁₂ ) -, (C ₁ -C ₁₂ ) - , (C ₂ -C ₁₂ ) and (C ₁ -C ₁₃ ) hydrocarbon radicals one or more, preferably up to three, CH ₂ groups by heteroatom units, such as O, NR ^{10 ″} or SiR ^{11 ″} R ^{12 ″} can be replaced and these heteroatom units are preferably not adjacent, where R ^{10 ″} , R ^{11 ″} and R ^{12 ″ have} the meanings such as R ¹⁰ , R ¹¹ , R ¹² and in addition 3 to 6 C atoms of these hydrocarbon radicals can form a cycle and these hydrocarbon radicals with or without these variations, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals from the series hydroxyl, halogen , Alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio are substituted;
Heteroaryl can be unsubstituted or can be provided with up to three, in the case of fluorine also up to the maximum number, identical or different substituents; Aryl has the meanings as under (8);
R ²⁴ and R ^{25 are} identical or different and independently of one another are hydrogen, (C ₁ -C ₄ -alkyl, (C ₁ -C ₄ ) -acyl, (C ₃ -C ₆ ) -cycloalkyl, phenyl and substituted phenyl and R ²¹ , R ²² , R ^{23 are the} same or different and independently of one another are (C ₁ -C ₁₈ ) alkyl, (C ₁ -C ₁₈ ) alkoxy, (C ₃ -C ₈ ) cycloalkyl and aryl, where in the (C ₁ -C ₁₈ ) hydrocarbon radicals, several, preferably up to three, CH ₂ groups can be replaced by oxygen and 3 to 6 carbon atoms of these hydrocarbon radicals can form a cycle, two of which are on the silicon bonded hydrocarbon residues (e.g. R ²¹ and R ²² ) can together form a cycle, as a result of which the silicon atom can optionally be part of this cycle and moreover these (C ₁ -C ₁₈ ) hydrocarbon residues with or without the variations, optionally with one or more in the case of halogen up to the maximum number of the same or different residues from de r series halogen, haloalkyl, cycloalkyl, may be substituted, it being possible for the substituents on the (C ₃ -C ₈ ) -cycloalkyl or (C ₅ -C ₈ ) -cycloalkenyl radicals defined above to be cis or trans with respect to the unit (XY) and in the event that the cycloalkyl group is the cyclohexyl radical and the above-mentioned units occupy the 1,4-position, the cis configuration is preferred; or
Y is a bond; and
Z (a) represents a group of formula II

wherein X ^{1 is} oxygen;
R ^{y is} (C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals listed are unsubstituted or with bis to three, in the case of fluorine also up to the maximum number of identical or different radicals and in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, non-adjacent saturated carbon units by heteroatom units , such as oxygen or SiR ²⁷ R ²⁸ can be replaced, where R ²⁷ and R ^{28 are} (C ₁ -C ₄ ) -alkyl, preferably methyl, and in addition 3 to 6 atoms of these hydrocarbon radicals, optionally modified as above, form a cycle can form and these hydrocarbon radicals with or without the specified variations, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals from the halogen series, preferably Fluorine, aryl, aryloxy, arylthio, (C ₃ -C ₈ ) -cycloalkoxy, (C ₃ -C ₈ ) -cycloalkylthio, heterocyclyl, heterocyclyloxy or (C ₁ -C ₂ ) -alkoxycarbonyl, which may be the cycloaliphatic , aromatic or heterocyclic ring systems under the just mentioned substituents may be unsubstituted or may be provided with up to three, in the case of fluorine also up to the maximum number of identical or different substituents, or R ^y and R ^z together form a five- or six-membered ring system , which is preferably spirocyclically linked to the ring system containing the heteroatoms X ¹ and in which a CH ₂ group can be replaced by heteroatom units such as oxygen, S (O) _n with n = 0, 1 or 2 or NR ²⁹ , where R ^{29 is} hydrogen (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkanoyl, benzoyl, aryl or heteroaryl, the benzoyl, aryl or heteroaryl radicals being unsubstituted or with up to three, in the case of fluorine also up to the maximum number en or different substituents can be provided, and the ring system formed from R ^y and R ^z can be unsubstituted or can be provided with up to three, but preferably one, substituent and these substituents are identical or different and in each case (C ₁ -C ₈ ) - Alkyl, (C ₃ -C ₈ ) -cycloalkyl, aryl or aryl- (C ₁ -C ₄ ) -alkyl mean, the cycloaliphatic, aromatic or heterocyclic ring systems under the just mentioned substituents unsubstituted or with up to three in the case of fluorine can also be provided with up to the maximum number of identical or different substituents, or the ring system formed from R ^y and R ^z together with a further benzene ring or cyclohexane ring forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, Dekalin or benzocycloheptane system, and the benzene ring in these condensed systems unsubstituted or with up to three, in the case of fluorine also up to the maximum number of the same or various substituents can be provided, wherein among the compounds for which the carbon atom between the heteroatoms X ¹ carries only the substituent R ^y , the substituents X and R ^y on the heteroaliphatic six-membered ring are preferably cis to one another; and
R ^{z is} hydrogen or
b) is a group of the formula (III)

wherein
Y ¹ , Y ² and Y ^{3 represent} a group of the formula -O-, -S (O) _r -, where r = 0, 1 or 2 or a group of the formula CR ³¹ R ³² , or Y ¹ or Y ³ stand in the place of a direct bond, whereby
R ³¹ and R ^{32 are} independently hydrogen or methyl;
m ^{1 represents} 1 or 2;
n ^{1 represents} 1 or 2;
Z ^{1 is} a direct bond, NR ³³ , O, S (O) _s with s = 0, 1 or 2, OSO ₂ , SO ₂ O, NR ³⁴ SO ₂ , SO ₂ NR ³⁵ , SiR ³⁶ R ³⁷ or

means where
U is a direct bond, NR ³⁸ or O;
W represents oxygen;
V represents a direct bond, NR ³⁹ or oxygen; and
R ³⁶ and R ^{37 are} (C ₁ -C ₄ ) alkyl or phenyl, preferably methyl;
R ³³ , R ³⁴ , R ³⁵ , R ³⁸ and R ^{39 are the} same or different and are each hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) - Is alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
R ^{q is} mutually independent (C ₁ -C ₈ ) -alkyl, in which one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by oxygen, and with or without the stated variations, optionally with one or several, preferably up to three, in the case of fluorine up to the maximum number of identical or different radicals D ¹ R ⁴³ may be substituted, or
R ^q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ² R ⁴⁴ .
D ¹ and D ^{2 are} each independently and a direct bond, -O-, -S (O) _k -, -SO ₂ O-, -OSO ₂ -, -CO-, -OCO-, -COO-, - NR ⁴⁶ -, -SO ₂ NR ⁴⁶ -, -NR ⁴⁶ SO ₂ -, -ONR ⁴⁶ -, -NR ⁴⁶ O-, -NR ⁴⁶ CO-, -CONR ⁴⁶ , and k = 0, 1 or 2, and where
R ^{46 is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
R ⁴³ and R ⁴⁴ independently of one another are hydrogen, halogen, preferably fluorine, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, aryl or heterocyclyl, the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁴⁹ , where
R ^{49 is} independently (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro, halogen can; or,
c) is a group of the formula IV

wherein
Y ^{4 represents} a direct bond or CH ₂ ;
Z ^{2 represents} oxygen;
R ^{u is} hydrogen, (C ₁ -C ₄ ) alkyl, tirfluoromethyl or (C ₁ -C ₄ ) alkoxy
W ¹ denotes direct bond, oxygen, -CO -, - COO-, CONR ⁵² , sulfur, -C = N-, -C = NO- and R ^{52 is} hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) - Alkanoyl and (C ₃ -C ₅ ) cycloalkyl means, and
R ^{t is} as defined under (12c) above.

Compounds of the formula I in which R ^{1 is} hydrogen are particularly preferred;
R ² and R ^{3 are} hydrogen, methyl, ethyl, propyl, methoxy, (C ₂ -C ₃ ) alkenyl, amino, (C ₁ -C ₄ ) alkylamino, (C ₁ -C ₄ ) dialkylamino, (C ₂ -C ₃ ) -chloro or -fluoro-alkenyl, (C ₂ -C ₃ ) -alkynyl, trimethylsilylethynyl, (C ₁ -C ₃ ) -chloro or -fluoroalkyl, methoxymethyl, halogen or cyano; or
R ² and R ³ together with the ring system to which they are attached form the quinazoline or quinoline system, which may be substituted by fluorine in the carbocyclic part; or
R ² and R ³ together with the carbon atoms to which they are attached form a saturated 6-membered ring which may contain an oxygen or sulfur atom instead of a CH ₂ group; in particular those compounds in which
R ^{1 represents} hydrogen;
R ^{2 is} methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (C ₁ -C ₂ ) fluoroalkyl or methoxymethyl;
R ^{3 is} fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C ₁ -C ₂ ) fluoroalkyl, amino, (C ₁ -C ₂ ) alkylamino, (C ₁ -C ₂ ) dialkylamino or methoxy; or if A is nitrogen,
R ² and R ³ together with the ring system to which they are attached form the quinazoline system, which can be substituted with a fluorine atom.

Also particularly preferred are compounds of formula I, in which
X represents NH;
Y represents a bond; and
Z (a) denotes cyclopentyl or cyclohexyl, where both radicals can optionally be substituted as above under (10) and in the case of cyclohexyl the 1,4-substitution is preferred, the substituents being in the cis position with respect to one another;
or
b) denotes a group of the formula II,

wherein
X ^{1 represents} oxygen;
R ^{z represents} hydrogen;
or
c) is a group of the formula III

wherein
Y ^{1 represents} CH ₂ ;
Y ^{2 represents} CH ₂ ;
Y ^{3 represents} CH ₂ , O or a direct bond;
m means ¹ 1
or
d) is a group of the formula IV

wherein
Y ^{4 represents} a direct bond or CH ₂ ;
Z ^{2 represents} oxygen;
R ^{u represents} hydrogen or methyl;
in particular those compounds in which
Z (a) denotes cyclohexyl, which may optionally be as above under (10), but preferably with a radical from the series (C ₁ -C ₈ ) -alkyl,
(C ₃ -C ₈ ) cycloalkyl,
(C ₃ -C ₈ ) cycloalkoxy,
(C ₂ -C ₈ ) alkenyl,
(C ₂ -C ₈ ) alkynyl,
(C ₁ -C ₈ ) alkoxy,
(C ₁ -C ₈ ) alkyloxycarbonyl,
SiR ²¹ R ²² R ²³ ,

Aryl,
Heteroaryl,
OAryl,
OHeteroaryl,
(C ₁ -C ₈ ) alkanediyldioxy and
(C ₁ -C ₁₃ ) -Alkyl-oximino is substituted, this substituent being in the 4-position of the cyclohexyl ring and being cis -containing with respect to the (XY) unit and, if not covered by the above definitions, in the above-mentioned (C ₁ -C ₈ ), (C ₂ -C ₈ ) hydrocarbon radicals one or more, preferably up to three, CH ₂ groups can be replaced by heteroatom units, such as O or SiR ^{11 ″} R ^{12 ″} can, where R ^{11 ''} and R ^{12 '' have} the same meaning as R ¹¹ , R ¹² and in addition 3 to 6 carbon atoms, these hydrocarbon radicals can form a cycle and these hydrocarbon radicals with or without the variations, if appropriate with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals from the series hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, are substituted;
Heteroaryl can be unsubstituted or can be provided with up to three, in the case of fluorine also up to the maximum number, identical or different substituents;
Aryl has the meanings as under (8);
R ²⁴ and R ^{25 are} identical or different and independently of one another are hydrogen, (C ₁ -C ₄ ) -alkyl, phenyl and substituted phenyl and R ²¹ , R ²² , R ^{23 are} identical or different and are independently of one another the meaning (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkoxy, (C ₃ -C ₈ ) cycloalkyl and aryl mean, in the (C ₁ -C ₈ ) hydrocarbon radicals several, preferably up to three CH ₂ groups can be replaced by oxygen and 3 to 6 carbon atoms of these hydrocarbon radicals can form a cycle, the silicon atom optionally being part of this cycle and moreover these (C ₁ -C ₈ ) hydrocarbon Radicals with or without the variations, optionally with one or more in the case of halogen up to the maximum number of identical or different radicals from the series halogen, haloalkyl, cycloalkyl, can be substituted;
or
b) denotes a group of the formula (II),

wherein
X ^{1 represents} oxygen;
R ^{z represents} hydrogen;
R ^{y is} (C ₁ -C ₁₅ ) alkyl, aryl or heterocyclyl in the sense of heteroaromatic ring system, the aryl or heterocyclyl radical being unsubstituted or having up to three, in the case of fluorine, up to the maximum number of identical or different radicals can be provided and in the alkyl radical mentioned one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by oxygen, and in addition 3 to 8 atoms of this optionally modified alkyl radical can form a cycle and this alyl radical can be provided with or without the specified variations, optionally with one or more halogen atoms, in the case of fluorine also up to the maximum number of identical or different substituents, and the substituents X and R ^y on the heteroaliphatic six-membered ring are preferably cis- are constant;
or
c) denotes a group of the formula (III),

wherein
n ^{1 represents} 1 or 2;
R ^{q is} independently of one another (C ₁ -C ₈ ) -alkyl, in which one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by oxygen, and with or without the stated variations, optionally with one or several, preferably up to three, in the case of fluorine up to the maximum number of identical or different radicals D ¹ R ⁴³ may be substituted, or
R ^q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ² R ⁴⁴ ; or
d) is a group of the formula IV

wherein
R ^{u represents} hydrogen;
R ^t denotes (C ₁ -C ₈ ) -alkyl, in which one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by oxygen, and which with or without the stated variations, optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number of identical or different radicals D ³ R ⁵⁶ can be substituted, or
R ^t can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ⁴ R ⁵⁷ .

Furthermore, particular preference is given to compounds of the formula I in which
A CH and DN⁺R
or
A represents nitrogen and DN⁺R;
Q⁻ represents an inorganic or organic anion, such as Hal⁻, NO⁻, BF ₄ ⁻, BPh ₄ ⁻, PF ₆ ⁻;
R ^{4 represents} hydrogen;
R ^{5 is} hydrogen, halogen, cyano, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl;
R ⁶ denotes aryl or heteroaryl, where the aryl and heteroaryl radicals may optionally be substituted by one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals Z ^{1 ′} -R ^{q ′} , where
Z ^{1 'is} a direct bond, O, OSO ₂ or

means where
U 'is a direct bond, or O;
W 'represents oxygen;
V 'represents a direct bond, NR ^39' or oxygen;
and
R ^{39 'represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
R ^{q '} are mutually independent substituents and is (C ₁ -C ₂₀ ) alkyl or (C ₂ -C ₂₀ ) alkenyl and optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number of the same or different radicals D ^{1 '} R ^43' may be substituted, or
R ^{q 'is} halogen, hydroxy, nitro or cyano, or
R ^{q 'can be} aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ^2' R ^{44 '} ;
D ^{1 '} and D ^{2' are} each independent of one another and are a direct bond, -O-, S (O) _k -, -SO ₂ O-, -OSO ₂ -, -CO-, -OCO-, -COO-, -NR ^46, -, -SO ₂ NR ^{46 '} -, -NR ^46' SO ₂ -, -ONR ^{46 '} , -NR-O-, -NR-CO-, -CONR ^46' - means, and k = 0 , 1 or 2, and wherein
R ^{46 'is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
R ^{43 '} and R ^44' independently of one another are hydrogen, halogen, preferably fluorine, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, aryl or heterocyclyl, the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ^{49 ′} , where
R ^{49 '} independently of one another (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro, halogen means.

Most preferred are those compounds of the formula I in which
R ^{1 represents} hydrogen;
R ^{2 represents} ethyl or methoxymethyl;
R ^{3 is} chlorine, bromine or methoxy, preferably those for which R ^{2 is} ethyl and R ^{3 is} chlorine;
R ⁴ means hydrogen
R ⁵ means hydrogen
R ⁶ denotes aryl or heteroaryl, where the aryl and heteroaryl radicals may optionally be substituted by one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals Z ^{1 ′} -R ^{q ′} , where
Z ^{1 'is} a direct bond, O or

means where
U 'is a direct bond, or O;
W 'represents oxygen;
V 'represents a direct bond, NR ^39' or oxygen;
and
R ^{39 'represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
Z ^{1 '} -R ^q' together represent halogen, nitro or cyano, or
R ^{q '} are mutually independent substituents and is (C ₁ -C ₁₂ ) alkyl or (C ₂ -C ₁₂ ) alkenyl and optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number of the same or different radicals R ^{43 '} may be substituted, or
R ^{q 'can be} aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ^2' R ^{44 '} ;
D ^{2 '} , are each independent of one another and a direct bond, -O-, -S (O) _k -, -SO ₂ O-, -OSO ₂ -, -CO-, -OCO-, -COO-, -NR ^{46 '} -, -SO ₂ NR ^46' -, -NR ^{46 '} SO ₂ -, -ONR ^46' -, -NR ^{46 '} O-, -NR ^46' CO-, -CONR ^{46 '} - means, and k = Is 0, 1 or 2, and 'where
R ^{46 'is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
R ^{43 '} and R ^44' independently of one another are hydrogen, cyano, nitro, halogen, preferably fluorine, (C ₁ -C ₈ ) -alkyl (C ₃ -C ₈ ) -cycloalkyl, aryl or heterocyclyl, in the latter 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems can be unsubstituted or can be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ^{49 '} , where
R ^{49 '} independently of one another are (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ haloalkoxy, cyano, nitro, halogen) can.

In the above formulas (I) to (IV), the radicals alkyl, alkoxy, haloalkyl, Halogenalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or be branched. Unless specifically stated, these residues are the lower carbon frameworks, e.g. B. with 1 to 6 carbon atoms or unsaturated Groups with 2 to 6 carbon atoms, preferred. Alkyl residues, also in the composite meanings such as alkoxy, haloalkyl, etc. mean z. B. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the Possible unsaturated radicals corresponding to alkyl radicals; Alkenyl means e.g. B. Allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; Alkynyl means e.g. B. propargyl, But-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.

Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, e.g. B. cyclopropyl, cyclopentyl or cyclohexyl, but also bicyclic systems, such as. B. the norbornyl group or the bicyclo [2.2.2] octane radical;
Halogen means, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, partially or completely substituted alkyl, alkenyl or alkynyl, for. B. monohalalkyl, perhaloalkyl, CF ₃ , CHF ₂ , CH ₂ F, CF ₃ CF ₂ , CH ₂ FCHCl, CCl ₃ , CHCl ₂ , CH ₂ CH ₂ Cl; Haloalkoxy is e.g. B. OCF ₃ , OCHF ₂ , OCH ₂ F, CF ₃ CF ₂ O, OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl; the same applies to haloalkenyl and other halogen-substituted radicals.

A hydrocarbon residue is a straight chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic Hydrocarbon residue, e.g. As alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or Aryl; preferably a hydrocarbon radical means alkyl, alkenyl or alkynyl  with up to 12 carbon atoms or cycloalkyl with 3, 4, 5, 6 or 7 ring atoms or Phenyl; the same applies to a hydrocarbon residue in one Hydrocarbonoxy group.

Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, Fluorenyl and the like, preferably phenyl.

A heterocyclic radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, ie heteroatoms or ring members, which also include substituted heteroatoms, preferably from the group N, O, S, SO, SO ₂ ; it is preferably an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms and contains 1, 2 or 3 hetero units. The heterocyclic radical can e.g. B. a heteroaromatic radical or ring (heteroaryl), such as. B. a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms, in particular an aromatic system in which at least 1, preferably up to 4, in particular up to 2 CH are replaced by N and / or at least 1, preferably up to 3-CH = CH units is replaced by NH, S or O, with the exclusion of adjacent O atoms, such as pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, Pyrazolyl and imidazolyl, or is a partially or fully hydrogenated radical such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo. The oxo group can also be attached to the hetero ring atoms, which can exist in different oxidation states, e.g. B. N and S occur.

Substituted radicals, such as substituted hydrocarbon radicals, e.g. B. substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl or heteroaryl mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals from the group halogen , Alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl Haloalkylsulfonyl and, in the case of cyclic radicals, also mean alkyl, cycloalkyl and haloalkyl; in the term "substituted radicals" such as substituted alkyl, etc., corresponding unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy, etc., are included as substituents in addition to the saturated hydrocarbon-containing radicals mentioned. In the case of radicals with carbon atoms, those with 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred. Preferred are usually substituents from the group halogen, z. B. fluorine and chlorine, (C ₁ -C ₄ ) alkyl, preferably methyl or ethyl, (C ₁ -C ₄ ) haloalkyl, preferably trifluoromethyl, (C ₁ -C ₄ ) alkoxy, preferably methoxy or ethoxy, (C ₁ -C ₄ ) -Haloalkoxy, nitro and cyano. The substituents methyl, methoxy and chlorine are particularly preferred.

Mono- or disubstituted amino means a chemically stable radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred; Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (C ₁ -C ₄ ) -alkanoyl. The same applies to substituted hydroxylamino or hydrazino.

Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, ( C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) haloalkoxy and nitro, e.g. B. o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and trichlorophenyl, 2,4-, 3,5-, 2, 5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.

An acyl residue means the residue of an organic acid, e.g. B. the rest of a carboxylic acid and residues derived therefrom, such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the rest of carbonic acid monoesters, optionally N-substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl means, for example, formyl, alkylcarbonyl such as [(C ₁ -C ₄ ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic acids. The radicals in each case in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy; Examples of substituents in the phenyl part are the substituents already mentioned above generally for substituted phenyl.

Furthermore, in the above formulas under the expression "dimethyl (C ₁ -C ₈ ) alkyl silyl-ethynyl" z. B. to understand the trimethylsilylethynyl or tert-butyldimethylsilylethynyl group;
under the expression "(C ₁ -C ₄ ) hydroxyalkyl" e.g. B. the hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-1-methyl-ethyl or the 1-hydroxypropyl group;
under the expression "(C ₁ -C ₄ ) alkanoyl" z. B. the formyl, acetyl, propionyl, 2-methylpropionyl or butyryl group; under the expression "(C ₁ -C ₁₂ ) alkanoyl" z. B. the aforementioned radicals and, for example, the valeroyl, pivaloyl, hexanoyl, decanoyl or the dodecanoyl group;
under the expression "(C ₂ -C ₄ ) haloalkanoyl" a (C ₁ -C ₄ ) alkanoyl group in which the hydrogen atoms are partially, in the case of fluorine also completely, replaced by halogen atoms, preferably fluorine or chlorine;
under the expression "(C ₂ -C ₁₂ ) haloalkanoyl" a (C ₁ -C ₂₀ ) alkanoyl group in which the hydrogen atoms are partially, in the case of fluorine also completely, replaced by halogen atoms, preferably fluorine or chlorine ;
under the term "cyan (C ₁ -C ₄ ) alkyl" a cyanoalkyl group whose hydrocarbon radical has the meanings given under the term "(C ₁ -C ₄ ) alkyl";
under the expression "(C ₁ -C ₄ ) alkylamino", for example methylamino, ethylamino, isopropylamino;
under the expression "(C ₁ -C ₄ ) dialkylamino", for example dimethylamino, N-ethyl-N-methylamino, diethylamino;
under the expression "(C ₁ -C ₄ ) alkoxycarbonyl" z. B. the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonyl group;
under the expression "(C ₁ -C ₁₂ ) alkoxycarbonyl" the above radicals and z. B. the hexyloxycarbonyl, 2-methylhexyloxycarbonyl, decyloxycarbonyl or dodecyloxycarbonyl group;
under the expression "(C ₁ -C ₄ ) haloalkoxycarbonyl" a (C ₁ -C ₄ ) alkoxycarbonyl group in which one or more, in the case of fluorine also optionally all hydrogen atoms, is replaced by halogen, preferably fluorine or chlorine are;
under the expression "(C ₁ -C ₄ ) haloalkylthio" a (C ₁ -C ₄ ) alkylthio group in which one or more, in the case of fluorine, if appropriate, all the hydrogen atoms of the hydrocarbon part by halogen, in particular chlorine or fluorine are replaced;
under the expression "(C ₁ -C ₄ ) alkylsulfinyl" e.g. B. the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butylsulfinyl group; under the expression "(C ₁ -C ₄ ) alkylsulfonyl" e.g. B. the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butylsulfonyl group; under the terms "(C ₁ -C ₄ ) haloalkylsulfinyl" and "(C ₁ -C ₄ ) haloalkylsulfonyl" (C ₁ -C ₄ ) alkylsulfinyl and sulfonyl radicals with the meanings given above, in which one one or more, in the case of fluorine, optionally all the hydrogen atoms in the hydrocarbon part are replaced by halogen, in particular chlorine or fluorine;
under the expression "(C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl", for example a 1-methoxyethylene group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a methoxymethyl or ethoxymethyl group, a 3-methoxypropyl group or a 4-butoxybutyl group;
under the terms "(C ₁ -C ₄ ) haloalkoxy- (C ₁ -C ₄ ) alkyl," (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) haloalkyl "and" (C ₁ -C ₄ ) haloalkoxy- (C ₁ -C ₄ ) haloalkyl "(C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl radicals with the meanings given above, in which one or more, in the case of fluorine, all of the hydrogen atoms in the corresponding hydrocarbon portions are optionally replaced by halogen, preferably chlorine or fluorine;
under the expression "(C ₁ -C ₄ ) alkylthio- (C ₁ -C ₄ ) alkyl" for example methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or 3-methylthiopropyl;
under the expression "arylthio" z. B. the phenylthio or the 1- or 2-naphthylthio group;
under the term "aryloxy" z. B. the phenoxy or 1- or 2-naphthyloxy group;
under the expression "heterocyclyloxy" or "heterocyclylthio" one of the abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom;
under the term "cycloalkoxy" or "cycloalkylthio" one of the cycloalkyl radicals mentioned above which are linked via an oxygen or sulfur atom; under the expression "aroyl" z. B. the benzoyl, naphthoyl or the biphenylcarbonyl group;
under the expression "aryl- (C ₁ -C ₄ ) alkanoyl" z. B. the phenylacetyl, 3-phenylpropionyl, 2-phenylpropionyl, 2-methyl-2-phenyl-propionyl, 4-phenylbutyryl or the naphthylacetyl group;
under the expression "(C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkanoyl" e.g. B. the cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclohexylacetyl or the cyclohexylbutyryl group;
under the expression "heterocyclyl- (C ₁ -C ₄ ) alkanoyl" z. B. the Thenoyl, Furoyl, Nicotinoyl, Thienylacetyl or the pyridine-propionyl group;
under the expression "(C ₃ -C ₈ ) cycloalkoxycarbonyl" z. B. the cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or the cycloheptyloxycarbonyl group;
under the expression "(C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkoxycarbonyl" e.g. B. the cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentyloxymethoxycarbonyl, cyclohexyloxymethoxycarbonyl, 1 - (cyclohexyl) ethoxycarbonyl or the ² - (cyclohexyl) ethoxycarbonyl group;
under the expression "aryl- (C ₁ -C ₄ ) alkoxycarbonyl" z. B. the benzyloxycarbonyl, 1-naphthylmethoxycarbonyl, 2-naphthylmethoxycarbonyl, 1-phenyl-ethoxycarbonyl or the 2-phenyl-ethoxycarbonyl group;
under the expression "heterocyclyl- (C ₁ -C ₄ ) alkoxycarbonyl", e.g. B. the thienylmethoxycarbonyl, furylmethoxycarbonyl, tetrahydrofurylmethoxycarbonyl or the pyridylethoxycarbonyl group;
under the term "aryloxycarbonyl" z. B. the phenoxycarbonyl, naphthoxycarbonyl or the biphenyloxycarbonyl group;
under the term "hetercyclyloxycarbonyl" z. B. the tetrahydropyran-4-oxycarbonyl group;
under the expression "(C ₁ -C ₂₀ ) alkanoyloxy" e.g. B. the formyloxy, acetoxy, propionyloxy, butyryloxy, pivaloyloxy, valeroyloxy or the hexanoyloxy group;
under the expression "(C ₂ -C ₂₀ ) haloalkanoyloxy" a (C ₂ -C ₂₀ ) alkanoyloxy group in which one or more, in the case of fluorine, if appropriate, all the hydrogen atoms of the hydrocarbon part by halogen, in particular fluorine or Chlorine are replaced;
under the expression "(C ₃ -C ₈ ) cycloalkanoyloxy" z. B. the cyclopropanoyloxy, cyclobutenoyloxy, cyclopentanoyloxy, cyclohexanoyloxy or the cycloheptanoyloxy group;
under the expression "(C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkanoyloxy" e.g. B. the cyclopropylcarbonyloxy, cyclopropylacetoxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cyclohexylacetoxy or the 4-cyclohexyl-butyryloxy group;
under the term "aroyloxy" e.g. B. the benzoyloxy or naphthoyloxy group;
under the expression "aryl- (C ₁ -C ₄ ) alkanoyloxy" z. B. benzoyloxy, naphthoyloxy, biphenylcarbonyloxy, phenylacetoxy or phenylbutyryloxy, under the expression "heterocyclyl- (C ₁ -C ₄ ) alkanoyloxy" z. B. the thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or the pyrimidinylcarbonyloxy group;
under the expression "(C ₁ -C ₂₀ ) alkylsulfonyloxy" e.g. B. the methane, ethane, butane or hexanesulfonyloxy group;
under the term "arylsulfonyloxy" e.g. B. the phenylsulfonyloxy or the toluenesulfonyloxy group;
a "bivalent hydrocarbon chain" means a radical derived from n-alkanes or n-alkenes by removing one hydrogen atom from each of the two terminal carbon atoms in the chain, such as methylene, ethanediyl, trimethylene, tetramethylene;
under the expression "(C ₁ -C ₁₈ ) alkanediyldioxy" one of (C ₁ -C ₁₈ ) alkanes by replacing two hydrogen atoms by two-O radicals derived divalent radical.

In addition, for example, under the definition that "in said alkyl, alkenyl or alkynyl radicals one or more, preferably up to three non-adjacent saturated carbon units by a carbonyl group or by heteroatom units such as oxygen, S (O) _x , with x = 0, 1 or 2, NR ²⁶ or SiR ²⁷ R ²⁸ can be replaced, where R ^{26 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or Is (C ₁ -C ₄ ) alkanoyl and R ²⁷ and R ^{28 are} (C ₁ -C ₄ ) alkyl, preferably methyl, and in addition 3 to 12 atoms of these hydrocarbon radicals, optionally modified as above, can form a cycle and these hydrocarbon radicals with or without the specified variations, optionally with one or more, preferably up to three, in the case of fluorine, up to the maximum number of identical or different radicals from the series halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, Heterocyclyl, heterocyclyloxy, He terocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, Halogenalkanoyloxy, cycloalkanoyloxy, Cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, Heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, Hydroxy, cyano, thiocyano or nitro can be substituted, it being possible for the cycloaliphatic, aromatic or heterocyclic ring systems to be unsubstituted or substituted with up to three, in the case of fluorine, up to a maximum number of the same or different substituents, where the Cycloaliphatic, aromatic or heterocyclic ring systems under the just mentioned substituents are unsubstituted or with up to three, in the case of fluorine also up to the maximum number of the same Chen or different substituents can be provided "z. B. to understand:
Alkoxyalkyl radicals, such as. B. the methoxymethyl, methoxyethyl or ethoxyethyl group; or
Alkoxy-alkoxy-alkyl radicals, such as. B. the methoxy or the ethoxy-ethoxyethyl group; or
Alkylthioalkyl radicals, such as. B. the methyl or ethylthioethyl group; or
Alkylsulfinyl-alkyl radicals, such as. B. the methyl or ethylsulfinylethyl group; or
Alkylsulfonyl-alkyl radicals, such as. B. the methyl or ethylsulfonylethyl group; or
Alkyl-dialkylsilyl-alkyl, preferably alkyl-dimethylsilyl-alkyl radicals, such as, for. B. the trimethylsilylmethyl or the trimethylsilylethyl group; or
Trialkylsilyl, preferably alkyldimethylsilyl radicals, such as. B. the trimethylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl or the octyldimethylsilyl group; or
Cycloalkyldialkylsilyl-, preferably Cycloalkyldimethylsilyl residues, such as. B. the cyclohexyldimethylsilyl group; or
Aryldialkylsilyl-, preferably aryldimethylsilyl radicals such as. B. phenyldimethylsilyl group; or
Arylalkyldialkylsilyl, preferably aryldimethylsilyl radicals such as. B. the benzyldimethylsilyl or the phenylethyldimethylsilyl group; or
Alkanoylalkyl radicals such as. B. the acetylmethyl or the pivaloylmethyl group; or
Cycloalkanoylalkyl radicals such as. B. the cyclopropylcarbonylmethyl or the cyclohexylcarbonylmethyl group; or
Halogenalkanoylalkyl residues such as. B. the trifluoro or trichloroacetylmethyl group; or
Aroylalkyl radicals such as. B. the benzoyl or naphthoylalkyl radicals such as. B. the phenylacetylmethyl group; or
Heterocyclylcarbonylalkyl residues such as. B. the thienyl or pyridylacetylmethyl group; or
Aryl-alkyl radicals, such as. B. the benzyl, the 2-phenylethyl, the 1-phenylethyl, the 1-methyl-1-phenylethyl group, the 3-phenylpropyl, the 4-phenylbutyl group, the 2-methyl-2-phenylethyl group or the 1-methyl or 2-methyl-naphthyl group; or
Heterocyclylalkyl residues, such as. B. the thienylmethyl, pyridylmethyl, furfuryl, tetrahydrofurfuryl, tetrahydropyranylmethyl or the 1,3-dioxalane-2-methyl group; or
Aryloxyalkyl radicals, such as. B. the phenoxymethyl or naphthoxymethyl group; or
Cycloalkyl residues, monocyclic such as. B. the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical, bicyclic such as. B. the norbornyl radical or the bicyclo [2,2,2] octane radical or condensed like the decahydronaphthyl radical;
Alkyl cycloalkyl radicals such as. B. the 4-methyl or 4-tert-butylcyclohexyl group or the 1-methyl-cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group;
Cycloalkyl-alkyl radicals such as. B. the cyclohexylmethyl or ethyl group;
or also haloalkyl derivatives of the corresponding groups, such as, for example, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkylcycloalkyl or halocycloalkyl radicals. The same applies to similar definitions.

Unless otherwise defined in detail, CH ₂ groups or saturated carbon units which are replaced by heteroatom units are preferably not adjacent.

The explanation given above applies accordingly to homologues or their derived residues.

In addition to the cis / trans isomerism mentioned, the compounds of the formula I have Share one or more asymmetric carbon atoms or stereoisomers Double bonds. Enantiomers or diastereomers can therefore occur. The invention encompasses both the pure isomers and their mixtures. The Mixtures of diasteromers can be made using common methods, e.g. B. by selective crystallization from suitable solvents or by chromatography be separated into the components. Racemates can be made according to usual Methods are separated into the enantiomers, such as. B. by salt formation  an optically active acid, separation of the diastereomeric salts and release the pure enantiomers using a base.

The invention further relates to a process for the preparation of compounds of the formula I, which is characterized in that a compound of the formula (V)

wherein G is CH or N and R ¹ , R ² , R ³ , X, Y and Z have the meanings given under formula I, with an electrophile of the formula (VI),

wherein R ⁴ , R ⁵ , R ⁶ and E have the meaning given under formula I and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, preferably halogen, optionally with addition of salts such as AgBF ₄ , AgNO ₃ or Nal and the anion of the compounds obtained in this way, if necessary, analogously to known methods [e.g. B. Liebigs Ann. Chem. 1978, 1937; Methods of Org. Chemie / Houben-Weyl (D. Klamann, Ed.), 4th edition, Vol. E16a, Part 2, S 1008 ff, Thieme, Stuttgart 1990] replaced by other anions.

The substitution reaction described above is known in principle [e.g. B. Methods the Org. Chemie / Houben-Weyl (D. Klamann, Ed.), 4th ed., Vol. E16a, Part 2, p. 997 ff, Thieme, Stuttgart 1990, Liebigs Ann. Chem. 621 (1959) 106.

The structures (V) and (VI) can be varied within wide limits.  

The above reaction is carried out in a temperature range of 20 to 150 ° C, optionally in an inert organic solvent such as acetonitrile, acetone, 2-butanone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, N- Methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, Ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene. Mixtures of the solvents mentioned can also be used be used.

The compounds of the formula (V) required as starting products are mostly known from the literature [e.g. B. DE-A-44 38 807, WO-A-96 11 913, WO-A- 96 11 924, DE-43 43 250, WO-A-95 07 890, WO-A-94 21 613, DE-A-42 08 254] or can be prepared analogously to known methods.

Compounds of formula (VI) are commercially available or can according to Principle known methods can be obtained [z. E.g. P.L. Spargo in Comprehensive Organic Functional Group Transformations (Katritzky, Meth-Cohn, Rees, Eds.), Vol. 2, pp. 1 ff, Pergamon, 1995].

With good plant tolerance and favorable toxicity to warm-blooded animals, the active substances are suitable for controlling animal pests, in particular insects, arachnids, helminths and molluscs, very particularly preferably for combating insects and arachnids, which are used in agriculture, in animal husbandry, in forests, in stocks and material protection as well as in the hygiene sector. They are effective against normally sensitive and resistant species as well as all or individual stages of development. The pests mentioned above include:
From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp.
From the order of the Isopoda z. B. Oniscus asselus, Armadium vulgar, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus.
From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spp.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Anoplura z. B. Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
From the order of the Mallophaga z. B. Trichodectes pp., Damalinea spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci, Frankliniella spp.
From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phoralososumum, pador, phorodoniphasum, pad. Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiis sppia, Fpp , Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Caulioacuaiaella, Galleria mellella Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cuaphalocrocis spp., Manduca spp.
From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Spp Psylloides chrysocephala, Epilachna varivestis, Atomaria., Oryzaephilus surinamensis spp, Anthonumus., Sitophilus spp. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucuslo, Gibb., Gibb , Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptus spp.
From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
From the order of the Siphonaptera z. B. Xenopsylla cheopsis, Ceratophyllus spp. From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans. From the class of the Helminth z. B. Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis as well as Fasciola.
From the class of the Gastropoda z. B. Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp. From the class of the Bivalva z. B. Dreissena spp.
The plant-parasitic nematodes that can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for. B. of the genera Meloidogyne (root-bile nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifoliihol, and the genus Radis such as Radisop such as Radis Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus), Tylenchulus (such as Tylenchulus semipenetrans), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (such as Rotylenchus robustusimususonusonoctonotinotoneus) (Heliocidonononotinusus) (Heliocidonotinonotinus) (Heliocidonotinonotinus) (Heliocidonotinonotinus) such as Longidorus elongatus), Trichodorus (like Trichodorus primitivus) and Xiphinema (like Xiphinema index).

Furthermore, with the compounds according to the invention Nematode genera Ditylenchus (stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (flower nematodes, such as Anguina tritici).

The invention also relates to agents, especially insecticidal and acaricidal agents, which the compounds of the formula I in addition to suitable formulation auxiliaries contain.

The agents according to the invention contain the active ingredients of the formulas I in generally 1 to 95% by weight.

They can be formulated in different ways, depending on how it is specified by the biological and / or chemical-physical parameters. Possible formulations are therefore:
Wettable powder (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil or water-based dispersions (SC), suspoemulsions (SE), dusts (DP), mordants, granules in the form of , Spray, elevator and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for example, in:
Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker NY, 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:
Watkins, "Handbook of Insecticide Dust Diluents and Garriers," 2nd Ed., Darland Books, Caldwell NJ; H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, NY; Marsden, Solvents Guide, 2nd Ed., Interscience, NY 1950; McCutcheon's, Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1967; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, combinations with others can also be made pesticidal substances, fertilizers and / or growth regulators produce, e.g. B. in the form of a finished formulation or as a tank mix. Are wettable powders preparations which are uniformly dispersible in water and which, in addition to the active ingredient a diluent or inert wetting agent, e.g. B. polyoxethylated Alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and Dispersants, e.g. B. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'- contain disulfonic acid sodium.

Emulsifiable concentrates are made by dissolving the active ingredient in one organic solvents, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. Can be used as emulsifiers for example: alkylarylsulfonic acid calcium salts such as Cadodecylbenzene sulfonate or nonionic emulsifiers such as Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,  Propylene oxide-ethylene oxide condensation products, alkyl polyethers, Sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or Polyoxethylene sorbitol ester.

Dusts are obtained by grinding the active ingredient with finely divided solid Fabrics, e.g. B. talc, natural clays such as kaolin, bentonite, pyrophillite or Diatomaceous earth. Granules can either by spraying the active ingredient adsorbable, granulated inert material or by Applying active ingredient concentrates using adhesives, e.g. B. polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of Carriers such as sand, kaolinite or granulated inert material. Can too suitable active ingredients in the usual for the production of fertilizer granules Way - if desired in a mixture with fertilizers - granulated.

In wettable powders, the active ingredient concentration is e.g. B. about 10 to 90 wt .-% of The remainder to 100 wt .-% consists of conventional formulation components. At emulsifiable concentrates, the active ingredient concentration can be about 5 to Amount to 80% by weight. Dust-like formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%. At Granules, the active ingredient content depends in part on whether the effective Connection is liquid or solid and which granulation aids, fillers etc. be used.

In addition, the active ingredient formulations mentioned optionally contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetrating agents, solvents, Fillers or carriers.

The concentrates available in commercial form are used optionally diluted in a conventional manner, e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and sometimes also in the case of microgranules using water. Dust-like and granulated preparations as well as sprayable solutions Usually not diluted with other inert substances before use.  

With the external conditions such as temperature, humidity and. a. varies the required application rate. It can fluctuate within wide limits, e.g. B. between 0.0005 and 10.0 kg / ha or more of active substance, is preferably however between 0.001 and 5 kg / ha.

The active compounds according to the invention can be in their commercially available Formulations as well as those prepared from these formulations Forms of use in mixtures with other active ingredients, such as insecticides Attractants, sterilants, acaricides, nematicides, fungicides, growth regulating substances or herbicides.

The pesticides include, for example, phosphoric acid esters, Carbamates, carboxylic acid esters, formamidines, tin compounds Microorganisms manufactured substances u. a.

Preferred mixing partners are

• 1. from the group of phosphorus compounds
  Acephate, Azamethiphos, Azinphos-ethyl-, Azinphosmethyl, Bromophos, Bromophos-ethyl, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Demeton, Demeton-S-methyl, Demeton-S-methyl sulfphone, Dialifos, Diazinon, Dichlorophos, Dicrotophos O, O-1,2,2,2-tetrachloroethylphosphorthioate (SD 208 304), Dimethoate, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitriothion, Fensulfothion, Fenthion, Fonofos, Formothion, Heptenophos, Isozophos, Isioophos , lsoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidim, phosimos, phoximim, phoxim, phoximim , Pirimiphos-methyl, Profenofos, Propaphos, Proetamphos, Prothiofos, Pyraclofos, Pyridapenthion, Quinalphos, Sulprofos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorphon, Vamidothion;
• 2. from the group of carbamates
  Aldicarb, 2-sec.-butylphenylmethylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl) carbamate, oxamoxuryl, pirimicanoxarbox , Ethyl-4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5, 11-dithia-9-dodecenoate (OK 135), 1-methylthio (ethylideneamino) - N-methyl-N- (morpholinothio) carbamate (UC 51717);
• 3. from the group of carboxylic acid esters
  Allethrin, alphametrin, 5-benzyl-34urylmethyl- (E) - (1R) -cis, 2,2-di-methyl-3- (2-oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate, bioallethrin, bioallethrin ((S) - cyclopentyl isomer ), Bioresmethrin, biphenates, (RS) -1-cyano-1- (6-phenoxy-2-pyridyl) methyl- (1RS) -trans-3- (4-tert.butylphenyl) -2,2-dimethylcyclopropane decarboxylate (NCI 85193), Cycloprothrin, Cyhalothrin, Cythithrin, Cypermethrin, Cyphenothrin, Deltamethrin, Empenthrin, Esfenvalerate, Fenfluthrin, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, Fluvalinate (D-Isomer), Prethrinin (R) -hrinethrinin , Pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, tralomethrin;
• 4. from the group of amidines
  Amitraz, chlorodime form;
• 5. from the group of tin compounds
  Cyhexatin, fenbutatin oxides;
• 6. Other
  Abamectin, Bacillus thuringiensis, Bensultap, Binapacryl, Bromopropylate, Buprofezin, Camphechlor, Cartap, Chlorobenzilate, Chlorfluazuron, 2- (4-Chlorphenyl) -4,5-diphenylthiophene (UBI-T 930), Chlorfentezine, Cyclopropancarbonsäurem (2-naphthylmethyl) ester (Ro12-0470), cyromazine, N- (3,5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propyloxy) phenyl) carbamoyl) -2-chlorobenzcarboximidic acid ethyl ester, DDT, Dicofol, N- (N- (3,5-di-chloro-4- (1,1,2,2-tetrafluoroethoxy) phenylamino) carbonyl) -2,6-difluorobenzamide (XRD 473), diflubenzuron, N- (2nd , 3-dihydro-3-methyl-1,3-thiazol-2-ylidenes) -2,4-xylidines, dinobutone, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl) - (dimethyl) (3- (3-phenoxyphenyl ) propyl) silane, (4-ethoxyphenyl) (3- (44luoro-3-phenoxyphenyl) propyl) dimethylsilane, fenoxycarb, 2-fluoro-5- (4- (4-ethoxyphenyl) -4-methyl-1-pentyl) diphenyl ether (MTI 800), Granulose and Kernpolyedei viruses, Fenthiocarb, Flubenzimine, Flucycloxuron, Flufenoxuron, Gamma-HCH, Hexythiazox, Hydramethylnon (AC 217300), Ivermectin, 2- Nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehydes (WL 108477), propargite, Teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron, imidacloprid.

The active substance content of those prepared from the commercially available formulations Forms of use can range from 0.00000001 to 95% by weight of active ingredient, preferably between 0.00001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms Wise.

The active compounds according to the invention are also suitable for combating endo- and ectoparasites in the veterinary field and in the field of Livestock farming.

The active compounds according to the invention are used here in a known manner Way as by oral use in the form of e.g. tablets, capsules, Soaking, granules, by dermal application in the form of, for example Diving (dipping), spraying (spraying), pouring (pour-on and spot-on) and des Powdering and parenteral use in the form of, for example Injection.

The new compounds of formula I according to the invention can accordingly particularly beneficial in livestock farming (e.g. cattle, sheep, pigs and Poultry such as chickens, geese, etc.) can be used. In a preferred one Embodiment of the invention, the animals the new compounds, if necessary in suitable formulations (see above) and if necessary with  administered orally to drinking water or feed. Because an excretion in the feces in done effectively, the development of Prevent insects in animal droppings. The appropriate dosages and Formulations are particularly of the type and stage of development Farm animals and also dependent on the infestation pressure and can be according to the usual Easily identify and determine methods. The new connections can be made at Cattle z. B. in doses of 0.01 to 1 mg / kg body weight.

The compounds of the formula I according to the invention are also notable for excellent fungicidal activity. Already in the plant tissue Invaded fungal pathogens can be successfully curated fight. This is particularly important and beneficial in such fungal diseases, no longer after infection with the usual fungicides can be effectively combated. The spectrum of effects of the claimed Compounds covers various economically important, phytopathogenic Mushrooms such as B. Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Piricularia oryzae, Pyrenophora teres, Leptosphaerea nodorum and Pellikularia sasakii and Puccinia recondita.

The compounds of the invention are also suitable for use in technical areas, for example as wood preservatives, as Preservatives in paints, in cooling lubricants for the Metalworking or as a preservative in drilling and cutting oils.

The active compounds according to the invention can be in their commercially available Formulations either alone or in combination with other Fungicides known from the literature are used.

As fungicides known in the literature which, according to the invention, with the compounds of Formula I can be combined, for. B. to name the following products: Aldimorph, Andoprim, Anilazine, BAS 480F, BAS 450F, BAS 490F, Benalaxyl, Benodanil, Benomyl, Binapacryl, Bitertanol, Bromuconazol, Buthiobate, Captafol, Captan, Carbendazim, Carboxin, CGA 173506, Cyprodinil, Cyprofuram,  Dichlofluanide, dichlomezin, diclobutrazole, diethofencarb, difenconazole (CGA 169374), difluconazole, dimethirimol, dimethomorph, diniconazole, dinocap, Dithianon, dodemorph, dodine, edifenfos, ethirimol, etridiazole, epoxiconazole, Fenbuconazole, fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, Fentin Acetate, Fentihydroxide, Ferimzone (TF1 64), Fluazinam, Fluobenzimine, Fludioxinil, fluquinconazole, fluorimide, flusilazole, flutolanil, flutriafol, folpet, Fosetylaluminium, Fuberidazole, Fulsulfamide (MT-F 651), Furalaxyl, Furconazole, Furmecyclox, Guazatine, Hexaconazole, ICI A5504, Imazalil, Imibenconazole, Iprobefos, iprodione, isoprothiolane, KNF 317, copper compounds such as Cu oxychloride, oxine-Cu, Cu-oxide, Mancozeb, Maneb, Mepanipyrim (KIF 3535), Metconazole, mepronil, metalaxyl, methasulfocarb, methfuroxam, MON 24000, Myclobutanil, Nabam, Nitrothalidopropyl, Nuarimol, Ofurace, Oxadixyl, Oxycarboxin, Penconazole, pencycuron, PP 969, probenazole, propineb, prochloraz, procymidone, Propamocarb, propiconazole, prothiocarb, pyracarbolide, pyrazophos, pyrifenox, Pyrimethanil, Pyroquilon, Rabenzazole, RH7592, Sulfur, Tebuconazole, TF 167, Thiabendazole, thicyofen, thiofanatemethyl, thiram, tolclofos-methyl, tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Tricyclazole, Tridemorph, Triflumizol, Triforine, Trifionazole, validamycin, vinchlozolin, XRD 563, Zineb, sodium dodecyl sulfonates, Sodium dodecyl sulfate, sodium C13 / C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester, dioctyl sodium sulfosuccinate, sodium isopropyl naphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, cetyl trimethyl ammonium chloride, salts of long-chain primary, secondary or tertiary Amines, alkyl propylene amines, lauryl pyrimidinium bromide, ethoxylated quaternized fatty amines, alkyl-dimethyl-benzyl-ammonium chloride and 1- Hydroxyethyl-2-alkyl imidazoline.

The above-mentioned combination partners are known active ingredients that are used for large part in Ch.R Worthing, S.B. Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council.

The active substance content of those prepared from the commercially available formulations Forms of use can vary widely, the active ingredient concentration the use forms can be from 0.0001 to 95% by weight of active compound, preferably are between 0.0001 and 1% by weight. The application takes place in a  Application forms customary usual way.

The following examples serve to illustrate the invention without this would be limited to this.

A. Examples of formulation

• a) A dusting agent is obtained by adding 10 parts by weight of active ingredient and 90 Parts by weight of talc as an inert substance and comminuted in a hammer mill.
• b) A wettable powder which is readily dispersible in water is obtained by using 25 parts by weight of active ingredient, 65 parts by weight of kaolin-containing quartz as Inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight oleoylmethyltauric acid sodium as a wetting and dispersing agent and grinds in a pin mill.
• c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active ingredient with 7 parts by weight of one Sulfosuccinic acid half ester, 2 parts by weight of a lignosulfonic acid Sodium salt and 51 parts by weight of water and mixed in one Grinding ball mill ground to a fineness of less than 5 microns.
• d) An emulsifiable concentrate can be prepared from 15 parts by weight Active ingredient, 75 parts by weight of cyclohexane as a solvent and 10 parts by weight ethoxylated nonylphenol (10 EO) as an emulsifier.
• e) Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or Quartz sand. A suspension of the is expediently used Spray powder from Example b) with a solids content of 30% and sprayed these onto the surface of an attapulgite granulate, dry and mix intimate. The proportion by weight of the wettable powder is about 5% and that of the inert carrier material approx. 95% of the finished granulate.

B. Production examples Example 1

1-benzyl-4- (cis-4-tert-butylcyclohexylamino) -5-chloro-6-ethyl-pyrimidinium bromide

2.00 g (6.77 mmol) 4- (cis-tert-butylcyclohexylamino) -5-chloro-6-ethyl-pyrimidine and 1.16 g (6.77 mmol) of benzyl bromide were stirred in boiling methanol for 8 h. The Solvent was removed in vacuo, the residue was stirred with ethyl acetate Aspirated crystals and recrystallized from toluene.

Yield 0.52 g (16%) crystals with mp. 207 ° C.

Example 2

4- (cis-4-tert-butylcyclohexylamino) -5-chloro-6-ethyl-1- (4-nitrobenzyl) - pyrimidinium bromide

0.7 g (2.37 mmol) of 4- (cis-tert-butylcyclohexylamino) -5-chloro-6-ethyl-pyrimidine and 0.56 g (2.61 mmol) of 4-nitrobenzyl bromide were placed in 10 ml of acetonitrile for 36 h Reflux stirred. The solvent was removed in vacuo, the residue with The ethyl acetate is stirred and the crystals are suctioned off.

Yield 0.68 g (56%) crystals with mp. 181 ° C.

Example 3

4- (cis-4-tert-butylcyclohexylamino) -5-chloro-6-ethyl-1- (4-pivaloyloxybenzyl) - pyrimidinium bromide

0.7 (2.37 mmol) 4- (cis-4-tert-butylcyclohexylamino) -5-chloro-6-ethyl-pyrimidine and 0.71 g (2.61 mmol) of (4-pivaloyloxy) benzyl bromide were placed in 10 ml of acetonitrile for 12 h heated to reflux. The solvent was removed in vacuo, the residue stirred with ethyl acetate and the crystals suctioned off.

Yield 0.84 g (63%) crystals with mp. 193 ° C.

Preparation of the educt (4-pivaloyloxy) benzyl bromide

5 g (0.46 mol) of p-cresol dissolved in 10 ml of DMF are added at 0 ° C. to a suspension of 2 g of sodium hydride (60%, 50 mmol) in 20 ml of dimethylformamide. The mixture is stirred at 0 ° C. for 10 min, 6.56 g (0.55 mol) of pivalic acid chloride is added dropwise and the mixture is warmed to 100 ° C. (TLC control). After cooling, the mixture is diluted with ether and washed with 2N NaOH, sat. NaHCO ₃ solution and sat. Saline. The organic phase is dried and concentrated, and the residue is purified by column chromatography on silica gel using petroleum ether / ethyl acetate (95: 5).

Yield 7.93 g 90%.

The product obtained is dissolved in 40 ml of carbon tetrachloride, containing 7.34 g (1 eq, 41 mmol) of N-bromosuccinimide and 0.32 g (4 mol%) of benzoyl peroxide were added and Reflux heated. After completion of the reaction (DC control), this will be Solvent removed and the residue with petroleum ether / ethyl acetate (9: 1) purified by column chromatography on silica gel. Yield 11 g (88%) of crystals Mp 46 ° C.

The compounds in the tables below were analogous to Examples 1 received to 3.

Definition of heterocycle residues Het ⁿ :

Het ¹

Het ²

Het ³

Het ⁴

Het ⁵

Het ⁶ *)

Het ⁷ *)

Het ⁸ *)

Het ⁹ *)

Het ¹⁰ *)

Het ¹¹ *)

Het ¹² *)

Het ¹³ *)

Het ¹⁴ *)

Het ¹⁵ *)

Het ¹⁶ *)

Het ¹⁷ *)

Het ¹⁸ *)

Het ¹⁹ *)

Het ²⁰ *)

*) These heterocycle residues have a high probability of specified constitution. But it cannot be with absolute certainty be excluded that the rest R instead of with an N + in the 1 position of the pyrimidine system with an N⁺ in the 3-position of this ring system is linked.

Other abbreviations used:
Ph phenyl
Me methyl
nPr n-propyl
iPr isopropyl
tBu tert-butyl

Defining the residues T

Table 1

C. Biological examples Use as an insecticide / acaricide / nematicide example 1

Cut stem with a leaf of bean plants (Phaseolus vulgaris) are transferred into amber glass bottles filled with tap water and then covered with about 100 spider mites (Tetranychus urticae). Plant leaf and spider mites are treated with an aqueous solution of the test and formulated preparation sprayed until it begins to drip. After this The plants and animals are drained in a climatic chamber (16 hours Light / day, 25 ° C, 40-60% RH). After 6 days of storage, the mortality of the Specimen found at all stages of the spider mite. With a concentration of 300 ppm (based on the active ingredient content) causes the preparation according to Example # 63 90-100% mortality.

Example 2

Germinated broad bean seeds (Vicia faba) with germ roots are in with Transfer tap water filled amber glass bottles and then with approx. 100 black bean aphids (Aphis fabae) coated. Plants and aphids with an aqueous solution of the preparation to be tested and formulated sprayed until drip starts. After draining, the plant and Animals stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 3 and 6 days of storage, the effect of the preparation on the aphids detected. At a concentration of 300 ppm (based on the content of Active ingredient) causes the preparation according to Example No. 63 90-100% mortality the aphids.

Example 3

Rice seed is germinated on moist cotton wool in glass jars. After this The leaves grow with an aqueous stem length of about 8 cm Solution of the preparation to be tested and formulated until the beginning Dripping sprayed. After draining, the rice plants treated in this way  placed in breeding containers and with 10 larvae (L3 stage) of the leafhopper species Nilaparvata lugens occupied. After draining, plants and animals are combined in one Climatic chamber stored (16 hours light / day, 25 ° C, 40-60% RH). At a Concentration of 300 ppm (based on the content of active ingredient) shows that Preparation according to Example No. 63 a 90-100% mortality in those used Laboratory animals.

Example 4

A petri dish, the bottom of which is half covered with filter paper and one Germinated grain of corn on a damp cotton swab is prepared. On the filter paper will be about 50, 4-5 day old eggs of the corn rootworm (Diabrotica undecimpunctata). The petri dish with the eggs and the corn kernel will then with an aqueous solution of the preparation to be tested and formulated sprayed. After the Petri dish is closed, it is placed in one at approx. 25 ° C Climate chamber stored. After 6 days of storage, the mortality of the preparation found on the eggs and possibly hatched larvae. At a Concentration of 300 ppm (based on the content of active ingredient) does this Preparation according to Example No. 63 a 90-100% mortality.

Example 5

Test part A (contact effect): In a glass vessel with an aqueous solution of the testing and formulated preparations are about 5000 newly hatched, active (Mobile) larvae (2nd stage of development) of the root gall nematode (Meloidogyne incognita) added. After 2 days of permanent exposure Nematode larvae is the percentage of exposure to the Specimens that have become motionless (immobile) in comparison to the untreated controls determined (percent nematicidal contact effect).

Test part B (soil drench effect): For this, the entire solution is made Test part A (active ingredient and pretreated nematode larvae) in a soil filled and planted with three 9-day-old cucumber plants (Cucumis sativus) Poured pot. The active substance content is reduced by this drench application based on the soil volume to one third of the active substance content from the test part  A. After two weeks in the greenhouse at approx. 26 ° C (watering twice a day) the root balls of the cucumber plants are contaminated with nematodes Carefully washed out soil mixture. The number of root galls per plant is counted and compared with the infestation of untreated control plants. The Calculation of the percentage reduction in infestation as a criterion for the Impact assessment is carried out according to the Abbott formula (percent nematicidal soil-drench effect).

At a concentration of 3 ppm in test part A or 1 ppm in test part B (in each case based on the content of active ingredient) effects the preparation according to the example No. 63 a 90-100% activity against the root bile nematode Meloidogyne incognita.

Example 6

Cut stem with a leaf of bean plants (Phaseolus vulgaris) are transferred into amber glass bottles filled with tap water and then covered with about 100 spider mites (Tetranychus urticae). Plant leaf and spider mites are then placed in an aqueous solution of the for 5 seconds testing and formulated preparation immersed. After draining Plant and animals stored in a climatic chamber (16 hours light / day, 25 ° C, 40- 60% RH). After 6 days of storage, the mortality of the preparation is reduced to all Stages of spider mites identified. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Example No. 71, 86, 111, 202, 208, 211, 212, 213, 214, 220, 221, 246, 259 a 90-100% Mortality.

Example 7

Germinated broad bean seeds (Vicia faba) with germ roots are in with Transfer tap water filled amber glass bottles and then with approx. 100 black bean aphids (Aphis fabae) coated. Plants and aphids are then placed in an aqueous solution of the test sample for 5 seconds formulated preparation immersed. After draining, plants and animals stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 3  and 6 days of storage will see the effect of the preparation on the aphids detected. At a concentration of 300 ppm (based on the content of Active ingredient) effect the preparations according to Example No. 73,111, 208, 211, 212, 213, 246 90-100% aphid mortality.

Example 8

The leaves of 12 rice plants with a stem length of 8 cm are used for 5 Seconds in an aqueous solution of the preparation to be tested and formulated submerged. After draining, the rice plants treated in this way are placed in a Petri dish placed and with about 20 larvae (L3 stage) of the leafhopper species Nilaparvata lugens occupied. After closing the Petri dish, it is placed in stored in a climatic chamber ((16 hours light / day, 25 ° C, 40-60% RH). After 6 The mortality of the cicada larvae is determined after days of storage. At a Concentration of 300 ppm (based on the content of active ingredient) cause the Preparations according to Example No. 72, 73, 74, 85, 86,111,124, 207, 208, 209, 212, 213, 220, 221, 246, 259 90-100% mortality.

Example 9

A petri dish, the bottom of which is covered with filter paper and approx. 5 ml nutrient medium contains, is being prepared. Filter paper pieces with approx. 30, 24 hour old eggs from the American tobacco bud owl (Heliothis virescens) are in for 5 seconds immersed in an aqueous solution of the preparation to be tested and formulated and then laid out in the petri dish. Another 200 ul of the aqueous solution are distributed over the nutrient medium. After closing the petri dish stored in a climatic chamber at approx. 25 ° C. After 6 days of storage, the Mortality of the preparation on the eggs and any larvae hatched from them detected. At a concentration of 300 ppm (based on the content of Active ingredient) effect the preparations according to Example No. 62, 85, 86,111, 212, 213, 214, 220, 221, 246, 259 a 90-100% mortality.

Example 10

A petri dish, the bottom of which is covered with filter paper and approx. 5 ml nutrient medium contains, is being prepared. Ten L2 larvae of the Egyptian cottonworm  (Spodoptera litoralis) are counted in a small cup. 200 µl one Aqueous solution of the preparation to be tested and formulated is placed in the beaker pipetted. Then the traded larvae are poured into the Petri dish and a further 200 ul of the aqueous solution are distributed over the nutrient medium. After the Petri dish is closed, it is placed in one at approx. 25 ° C Climate chamber stored. After 6 days of storage, the effect of the preparation found on the larvae. At a concentration of 300 ppm (based on the Active ingredient content) effect the preparations according to Example No. 68, 212, 221, 246 a 90-100% mortality of the larvae.

Example 11

A petri dish, the bottom of which is half covered with filter paper and one Germinated grain of corn on a damp cotton swab is prepared. On the filter paper will be about 50, 4-5 day old eggs of the corn rootworm (Diabrotica undecimpunctata). Three drops of 200 ul of an aqueous solution of preparation to be tested and formulated is on the eggs and the rest on the Pipetted corn kernel. After closing the Petri dish, it is at approx. 25 ° C stored in a climatic chamber. After 6 days of storage, the mortality of the Specimen found on the eggs and possibly hatched larvae. At a concentration of 300 ppm (based on the content of active ingredient) the preparations according to Example No. 62, 64, 65, 67, 68, 70, 71, 72, 73, 74, 85, 86, 111, 209, 212, 213, 220, 221, 246 a 90-100% mortality.

Example 12

Test part A (contact effect): In a glass jar, about 5000 newly hatched, active (mobile) larvae (2nd stage of development) of the Root gall nematodes (Meloidogyne incognita) an aqueous solution of the testing and formulated preparation added (final volume 20 ml). After 6- Daily exposure of the nematode larvae is the percentage of the influence of the preparation immobile individuals in the Comparison to the untreated controls determined (percent nematicidal Contact effect).  

Test part B (soil drench effect): For this, the entire solution is made Test part A (active ingredient and pretreated nematode larvae) in a 60 ml Soil filled with three 9 day old cucumber plants (Cucumis sativus) planted pot poured. This drench application reduces the Active substance content based on the soil volume to one third of the active substance content from test part A. After two weeks in the greenhouse at approx. 26 ° C (twice watering daily) are the root balls of the cucumber plants from the Carefully washed out nematode contaminated soil mixture. The number of Root gall per plant is counted and untreated with the infestation Control plants compared. The calculation of the percentage infestation reduction as The criterion for the impact assessment is based on the Abbott formula (Percent nematicidal soil-drench effect).

At a concentration of 3 ppm in test part A or 1 ppm in test part B (each based on the active ingredient content) effect the preparations according to Example Nos. 221, 246 a 90-100% effect over that Root bile nematodes Meloidogyne incognita.

Claims (23)

1. Compounds of the formula I
in which

• 1) A CH and DN⁺R
  or
  A nitrogen and DN⁺R
  or
  AN⁺R and D means nitrogen, in which
  R for
  stands;
• 2) Q ^{n- is} any inorganic or organic anion, where n is 1, 2, 3 or 4;
• 3) R ^{1 is} hydrogen, halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl or (C ₃ -C ₅ ) cycloalkyl;
• 4) R ² and R ^{3 are} identical or different and are each hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) -Halogenalkenyl, (C ₂ -C ₄ ) alkynyl, (C ₂ -C ₄ ) -haloalkynyl, (C ₁ -C ₈ ) -trialkylsilylalkynyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -Halogenalkoxy, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) haloalkoxy- (C ₁ -C ₄ ) haloalkyl, amino, monosubstituted amino, disubstituted amino, halogen, hydroxy, (C ₁ -C ₄ ) hydroxyalkyl, (C ₁ -C ₄ ) alkanoyl, (C ₁ -C ₄ ) alkanoyl- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkanoyl, (C ₃ -C ₅ ) cycloalkyl, (C ₃ -C ₅ ) halocycloalkyl, cyano, (C ₁ -C ₄ ) cyanoalkyl, nitro, (C ₁ C ₄ ) nitroalkyl, thiocyano, (C ₁ C ₄ ) thiocyanoalkyl , (C ₁ -C ₄ ) alkoxycarbonyl, (C ₁ -C ₄ ) alkoxycarbonyl- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkoxycarbonyl, (C ₁ -C ₄ ) alkylthio , (C ₁ -C ₄ ) alkylthio- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) - Haloalkylthio, (C ₁ -C ₄ ) alkylsulfinyl, (C ₁ -C ₄ ) haloalkylsulfinyl, (C ₁ -C ₄ ) alkylsulfonyl or (C ₁ -C ₄ ) haloalkylsulfonyl; or
  R ² and R ³ together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered isocyclic ring which, if it is a 5-ring, instead of CH _{2, represents} an oxygen or sulfur atom or which, if it is a 6-ring, can contain one or two nitrogen atoms instead of one or two CH units and which is optionally substituted by 1, 2 or 3 identical or different radicals and these radicals (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, halogen, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) haloalkoxy; or
  R ² and R ³ together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered isocyclic ring which may contain oxygen and / or sulfur instead of one or two CH ₂ groups and which is optionally substituted by 1, 2 or 3 (C ₁ -C ₄ ) alkyl groups;
• 5) XO, S (O) _q with q = 0, 1 or 2, NR ⁷ or CR ⁸ R ⁹ , where R ^{7 is} hydrogen and R ⁸ and R ⁹ independently of one another are hydrogen or (C ₁ -C ₄ ) -Alkyl mean.
• 6) YZ together means a (C ₁ -C ₂₀ ) hydrocarbon radical which is unbranched or branched and in which one or more CH _{2 can be} replaced by heteroatom units, where R ^{10 is} hydrogen, (C ₁ -C ₄ ) alkyl or (C ₁ -C ₄ ) acyl, and R ¹¹ and R ¹² , which are the same or different, independently of one another are (C ₁ -C ₄ ) alkyl, phenyl or substituted phenyl, and wherein this (C ₁ -C ₂₀ ) -hydrocarbon residue with the possible aforementioned variations, optionally with one or more identical or different residues from the series
  (C ₁ -C ₇ ) alkyl,
  (C ₂ -C ₄ ) alkenyl,
  (C ₂ -C ₄ ) alkynyl,
  (C ₃ -C ₇ ) cycloalkyl,
  (C ₃ -C ₇ ) cycloalkenyl,
  Halogen,
  Halogen (C ₁ -C ₄ ) alkyl,
  Halogen (C ₁ -C ₄ ) alkoxy,
  Hydroxy and
  (C ₁ -C ₄ ) acyl is substituted; or, if not covered by the above definitions,
• 7) Y is a bond or a divalent hydrocarbon chain with 1 to 6 carbon atoms, optionally with one or more identical or different radicals from the series
  (C ₁ -C ₇ ) alkyl,
  (C ₂ -C ₄ ) alkenyl,
  (C ₃ -C ₇ ) alkynyl,
  (C ₃ -C ₇ ) cycloalkyl,
  (C ₃ -C ₇ ) cycloalkenyl,
  Halogen,
  Halogen (C ₁ -C ₄ ) alkyl,
  Halogen (C ₁ -C ₄ ) alkoxy,
  Hydroxy and
  (C ₁ -C ₄ ) acyl is substituted; and
• 8) Z means aryl or O-aryl, optionally with one or more identical or different radicals from the series
  Halogen,
  (C ₃ -C ₈ ) cycloalkyl,
  (C ₃ -C ₆ ) cycloalkenyl,
  Phenoxy,
  substituted phenoxy,
  Phenylthio,
  substituted phenylthio,
  Phenyl,
  substituted phenyl,
  NO ₂ ,
  Acetoxy,
  Hydroxy,
  Cyano,
  SiR ¹⁴ R ¹⁵ R ¹⁶ ,
  O-SiR ¹⁴ R ¹⁵ R ¹⁶ ,
  NR ¹⁷ R ¹⁸ ,
  S (O) R ¹⁹ ,
  SO ₂ R ¹⁹ ,
  (C ₁ -C ₁₂ ) alkyl,
  (C ₂ -C ₁₂ ) alkenyl,
  (C ₁ -C ₁₂ ) alkoxy and
  (C ₁ -C ₁₂ ) alkylthio is substituted; and
  R ¹³ (C ₁ -C ₇ ) alkyl, halogen (C ₁ -C ₇ ) alkyl, (C ₃ -C ₇ ) cycloalkyl, halogen (C ₃ -C ₇ ) cycloalkyl, (C ₁ - C ₇ ) alkoxy, phenyl or substituted phenyl;
  R ¹⁴ , R ¹⁵ and R ^{16 are} identical or different and independently of one another are (C ₁ -C ₄ ) alkyl, phenyl and / or substituted phenyl;
  R ¹⁷ and R ^{18 are} identical or different and independently of one another are hydrogen, (C ₁ -C ₄ ) -alkyl and / or (C ₁ -C ₄ ) -acyl;
  R ^{19 represents} (C ₁ -C ₁₀ ) alkyl, phenyl or substituted phenyl;
  where in (C ₁ -C ₁₂ ) alkyl, (C ₁ -C ₁₂ ) alkoxy, (C ₁ -C ₁₂ ) alkylthio and (C ₂ -C ₁₂ ) alkenyl, optionally one or more CH ₂ groups are replaced by heteroatom units; R ^{10 '} , R ^11' and R ^{12 '} have the same meaning as R ¹⁰ , R ¹¹ , R ¹² ;
  the (C ₁ -C ₁₂ ) alkyl radical with or without the abovementioned variations and also with one or more identical or different of the following radicals from the series halogen, halogen (C ₁ -C ₄ ) alkoxy, hydroxy, (C ₃ - C ₈ ) cycloalkyl, (C ₃ -C ₈ ) cycloalkenyl, (C ₁ -C ₄ ) acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio may be substituted; in the (C ₁ -C ₇ ) alkoxy and (C ₁ -C ₇ ) alkylthio residues one or more CH ₂ groups can be replaced by O and these residues may be replaced by one or more identical or different residues from the Halogen, phenyl, substituted phenyl, (C ₃ -C ₈ ) cycloalkyl, (C ₃ - C ₈ ) cycloalkenyl, phenoxy and substituted phenoxy are substituted; or if not covered by the above definitions,
• 9) Y is a bond or a divalent hydrocarbon chain with 1 to 6 carbon atoms, optionally with one or more, preferably up to three identical or different radicals from the series
  (C ₁ -C ₇ ) alkyl,
  (C ₂ -C ₄ ) alkenyl,
  (C ₃ -C ₇ ) alkynyl,
  (C ₃ -C ₇ ) cycloalkyl,
  (C ₃ -C ₇ ) cycloalkenyl,
  Halogen,
  Halogen (C ₁ -C ₄ ) alkyl,
  Halogen (C ₁ -C ₄ ) alkoxy,
  Hydroxy and
  (C ₁ -C ₄ ) acyl is substituted; and
• 10) Z is (C ₃ -C ₈ ) cycloalkyl or (C ₅ -C ₈ ) cycloalkenyl, where a CH ₂ group of the carbocycle can be replaced by NR ²⁰ ;
  R ²⁰ is phenyl or substituted phenyl and (C ₃ - C ₈₎ cycloalkyl or (C ₅ -C ₈₎ cycloalkenyl radical optionally substituted with one or more identical or different radicals from the series
  (C ₁ -C ₁₈ ) alkyl,
  (C ₃ -C ₈ ) cycloalkyl,
  (C ₃ -C ₈ ) cycloalkoxy,
  (C ₂ -C ₁₈ ) alkenyl,
  (C ₂ -C ₁₈ ) alkynyl,
  (C ₁ -C ₁₂ ) alkoxy,
  (C ₁ -C ₁₂ ) alkanoyloxy,
  Formyl,
  (C ₂ -C ₁₂ ) acyl,
  (C ₁ -C ₁₂ ) alkyloxycarbonyl,
  SiR ²¹ R ²² R ²³
  NR ²⁴ R ²⁵ ,
  Hydroxyl,
  Halogen,
  Aryl,
  Heteroaryl,
  OAryl,
  OHeteroaryl,
  (C ₁ -C ₁₈ ) alkanediyldioxy,
  (C ₁ -C ₁₃ ) alkyl oximino and
  (C ₂ -C ₁₈ ) alkylidene are substituted and, if not covered by the above definitions, in the (C ₁ -C ₁₈ ) -, (C ₂ -C ₁₈ ) -, (C ₁ -C ₁₂ ) - , (C ₂ -C ₁₂ ) - and (C ₁ -C ₁ -) - hydrocarbon radicals one or more CH ₂ groups can be replaced by heteroatom units, where R ^{10 ″} , R ^{11 ″} and R ^{12 '' have} the same meaning as R ¹⁰ , R ¹¹ , R ¹² and moreover 3 to 6 carbon atoms of these hydrocarbon radicals can form a cycle and these hydrocarbon radicals with or without these variations, if appropriate with one or more identical or different radicals from the series hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio;
  Heteroaryl can be unsubstituted or can be provided with up to three, in the case of fluorine also up to the maximum number, identical or different substituents;
  Aryl has the meanings as under (8);
  R ²⁴ and R ^{25 are the} same or different and are independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) acyl, (C ₃ -C ₆ ) cycloalkyl, phenyl and substituted phenyl and R ²¹ , R ²² , R ^{23 are the} same or different and independently of one another are (C ₁ -C ₁₈ ) alkyl, (C ₁ -C _{1 8} ) alkoxy, (C ₃ -C ₈ ) cycloalkyl and aryl , where in the (C ₁ -C ₁₈ ) hydrocarbon radicals several non-adjacent CH ₂ groups can be replaced by oxygen and 3 to 6 carbon atoms of these hydrocarbon radicals can form a cycle, two of which are also bonded to the silicon Carbon residues can together form a cycle, whereby the silicon atom is then a ring atom of this cycle and furthermore these (C ₁ -C ₁₈ ) hydrocarbon residues with or without the variations, optionally with one or more in the case of halogen up to the maximum number of identical or different radicals from the series halogen, haloalkyl, cycloalkyl, see may be substituted, where the substituents on the cycloalkyl or cycloalkenyl radicals defined under (10) may be cis or trans with respect to the unit (XY) or
• 11) Y is a bond; and
• 12) Z (a) denotes a group of the formula II
  wherein X ^{1 is} independently sulfur or oxygen;
  R ^{z represents} hydrogen, (C ₁ -C ₄ ) alkyl, trifluoromethyl or (C ₁ -C ₄ ) alkoxy; or
  R ^{y is} alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals listed may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different radicals and in the alkyl mentioned , Alkenyl or alkynyl radicals one or more non-adjacent saturated carbon units can be replaced by a carbonyl group or by heteroatom units, where R ^{26 is} hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl and R ²⁷ and R ^{28 represent} (C ₁ -C ₄ ) alkyl;
  and in which, in addition, 3 to 12 atoms of these hydrocarbon radicals, optionally modified as above, can form a cycle and these hydrocarbon radicals with or without the stated variations, optionally with one or more identical or different radicals from the series halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, Halogenalkanoyloxy, cycloalkanoyloxy, Cycloalkylalkanoyloxy, Aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxy, cyano, thiocyano or nitro can be substituted, the cycloaliphatic, aromatic or heterocyclic ring system teme may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents, or R ^y and R ^z together form a three- to eight-membered ring system, which with the the ring system containing heteroatoms X ¹ is linked spirocyclically and in which one or two CH ₂ groups can be replaced by heteroatom units, where R ²⁹ denotes hydrogen, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, the benzoyl, Aryl or heteroaryl radicals can be unsubstituted or can have up to three, in the case of fluorine, up to the maximum number of identical or different substituents, and the ring system formed from R ^y and R ^z can be unsubstituted or can have up to three substituents and these substituents are identical or different and are each alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, Arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or alkoxycarbonyl, the cycloaliphatic, aromatic or heterocyclic ring systems being unsubstituted or with up to three different numbers of the same or up to three in the case of fluorine Substituents can be provided, or the ring system formed from R ^y and R ^z together with a further benzene ring or cyclohexane ring forms a condensed ring system and the benzene ring in these condensed systems is unsubstituted or with up to three, in the case of fluorine, up to the maximum number of the same or can be provided with various substituents; or
• b) is a group of the formula III
  wherein
  Y ¹ , Y ² and Y ³ independently of one another a group of the formula -O-, -CO -, - CNR ³⁰ -, -S (O) _r - with r = 0, 1 or 2, -N (O) _l R ³⁰ - with l = 0 or 1 or a group of the formula CR ³¹ R ³² ; or
  Y ¹ or Y ^{3 are} in place of a direct bond,
  in which
  R ^{30 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) haloalkenyl, (C ₂ -C ₄ ) Alkynyl, (C ₂ -C ₄ ) haloalkynyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₄ ) Haloalkylthio, (C ₁ -C ₄ ) alkanoyl, (C ₂ -C ₄ ) haloalkanoyl, (C ₃ -C ₅ ) cycloalkyl, (C ₁ -C ₄ ) alkylsulfonyl, (C ₁ -C ₄ ) Haloalkylsulfonyl, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxycarbonyl;
  R ³¹ and R ³² independently of one another are hydrogen, hydroxy, halogen, cyano, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄₎ haloalkenyl, (C ₂ -C ₄₎ -alkynyl, (C ₂ -C ₄₎ - haloalkenyl, (C ₃ -C ₅₎ cycloalkyl, (C ₁ -C ₄₎ alkanoyl, (C ₁ -C ₄ ) - haloalkanoyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkylthio or (C ₁ -C ₄ ) haloalkylthio;
  m ^{1 represents} 0, 1, 2, 3 or 4;
  n ^{1 represents} 0, 1, 2, 3 or 4;
  Z ^{1 is} a direct bond, NR ³³ , O, S (O) _s with s = 0, 1 or 2, OSO ₂ , SO ₂ O, NR ³⁴ SO ₂ , SO ₂ NR ³⁵ , SiR ³⁶ R ³⁷ or
  means
  in which
  R ³⁶ and R ^{37 are} (C ₁ -C ₄ ) alkyl or phenyl;
  U is a direct bond, NR ³⁸ or O;
  W represents oxygen or sulfur;
  V represents a direct bond, NR ³⁹ or oxygen, where
  R ³³ , R ³⁴ , R ³⁵ , R ³⁸ and R ^{39 are the} same or different and each represents hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
  R ^q are independent substituents and are halogen, cyano, nitro, (C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, (C ₃ -C ₈ ) -Cycloalkyl, (C ₄ -C ₈ ) -cycloalkenyl means and in the latter 5 radicals one or more non-adjacent saturated carbon units can be replaced by a carbonyl group or by heteroatom units and these last 5 radicals with or without the stated variations , optionally substituted with one or more identical or different radicals D ¹ R ⁴³ , or
  R ^q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine up to the maximum number of identical or different radicals D ² R ⁴⁴ , or two adjacent radicals
  Z ¹ -R ^q together with the C atoms carrying these can form a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group of O, S and N and which is unsubstituted or by one or more radicals from the Group of halogen, (C ₁ -C ₄ ) alkyl and oxo is substituted, or
  R ³³ , R ³⁵ or R ³⁹ independently of one another can form a 4- to 8-membered ring system with the R ^q located on Z, in which one or two CH ₂ groups can be replaced by heteroatom units,
  in which
  R ^{40 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl;
  R ⁴¹ and R ⁴² independently of one another are (C ₁ -C ₄ ) -alkyl;
  D ¹ and D ^{2 are} each independently and a direct bond, oxygen, S (O) _k , SO ₂ O, OSO ₂ , CO, OCO, COO, NR ⁴⁶ , SO ₂ NR ⁴⁶ , NR ⁴⁶ SO ₂ , ONR ⁴⁶ , NR ⁴⁶ O, NR ⁴⁶ CO, CONR ⁴⁶ or SiR ⁴⁷ R ⁴⁸ , and k = 0, 1 or 2, where
  R ^{46 is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
  R ⁴⁷ and R ⁴⁸ independently of one another are (C ₁ -C ₄ ) -alkyl;
  R ⁴³ and R ⁴⁴ independently of one another hydrogen, cyano, nitro, halogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) haloalkenyl, (C ₂ -C ₈ ) alkynyl (C ₂ -C ₈ ) haloalkynyl, (C ₁ -C ₈ ) alkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) - Haloalkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) alkylthio- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) -haloalkylthio- (C ₁ -C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkyl, (C ₄ -C ₈ ) - Cycloalkenyl- (C ₁ -C ₄ ) -alkyl, aryl, heterocyclyl, aryl- (C ₁ -C ₄ ) -alkyl or heterocyclyl- (C ₁ -C ₄ ) -alkyl, the 8 radicals in which the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁴⁹ , or
  R ⁴³ and R ^{44 together} on the same C atom represent an oxo group,
  in which
  R ^{49 is} (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro or halogen ;
  R ^{45 is} hydrogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkylthio, (C ₃ -C ₅ ) -Cycloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, (C ₁ -C ₄ ) alkanoyl, (C ₂ -C ₄ ) haloalkanoyl, (C ₂ -C ₄ ) -Alkoxyalkyl, phenyl- (C ₁ -C ₄ ) -alkyl or phenyl and the phenyl groups may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁵⁰ , where
  R ^{50 represents} (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkylthio, halogen or cyano;
  or, if not covered by the above definitions,
• c) is a group of the formula IV
  wherein
  Y ^{4 is} direct bond or CH ₂ ;
  Z ^{2 represents} oxygen, NR ⁵¹ , S (O) _m with m = 0, 1 or 2;
  R ^u and W ¹ -R ^{t are} substituents of the heteroaliphatic ring system, where
  R ^{u is} hydrogen, halogen, cyano, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) haloalkenyl, (C ₂ -C ₄ ) alkynyl, (C ₂ -C ₄ ) haloalkynyl, (C ₃ -C ₆ ) cycloalkyl, (C ₄ -C ₆ ) cycloalkenyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkanoyloxy, (C ₁ -C ₄ ) haloalkanoyloxy, (C ₁ -C ₄ ) alkylthio or (C ₁ -C ₄ ) haloalkylthio;
  W ¹ denotes direct bond, oxygen, -NR ⁵² -, -CO-, -COO-, CONR ⁵² -, sulfur, -C = N-, -C = NO- or -NR ⁵² O-;
  R ^{t is} hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl and in the latter 5 radicals one or more non-adjacent saturated carbon units can be replaced by a carbonyl group or by heteroatom units, and these latter 5 radicals with or without the indicated variations, may optionally be substituted with one or more identical or different radicals D ³ R ⁵⁶ , or
  R ^t can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ⁴ R ⁵⁷ , or
  R ^u and R ^t together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the heteroatoms Y ⁴ and Z ² and in which one or two CH ₂ groups can be replaced by heteroatom units,
  in which
  R ^{51 is} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) haloalkenyl, (C ₂ -C ₄ ) Alkynyl, (C ₂ -C ₄ ) haloalkynyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkanoyl, (C ₂ -C ₄ ) haloalkanoyl, (C ₁ -C ₄ ) -Alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkylthio- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) - Alkylsulfonyl, (C ₁ -C ₄ ) -haloalkylsulfonyl, phenylcarbonyl, phenyl- (C ₁ -C ₄ ) -alkyl or phenyl, the latter 3 radicals being unsubstituted or with up to three, in the case of fluorine also up to Maximum number of identical or different substituents R ⁵⁹ can be substituted, or
  R ^{51 means} CONR ⁶⁰ R ⁶¹ , wherein
  R ⁶⁰ and R ⁶¹ independently of one another are hydrogen, (C ₁ -C ₄ ) -alkyl or phenyl, where the phenyl group can be unsubstituted or substituted by up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁶² , and
  R ⁶² and R ⁵⁹ independently of one another (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) - alkylthio or halogen;
  R ^{52 represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
  R ^{53 represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkanoyl;
  R ⁵⁴ and R ^{55 are} independently (C ₁ -C ₄ ) alkyl;
  R ^{58 is} hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, the latter 3 radicals being unsubstituted or having up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁶³ ;
  R ⁶³ (C ₁ -C ₄₎ -alkyl, (C ₁ -C ₄₎ -haloalkyl, (C ₁ -C ₄₎ alkoxy, (C ₁ -C ₄₎ - may be haloalkoxy, cyano, nitro or halogen, and the ring system formed from R ^u and R ^t may be unsubstituted or provided with up to three substituents D ⁵ R ⁶⁴ , or the ring system formed from R ^u and R ^t together with a further benzene ring or cyclohexane ring forms a condensed ring system and the benzene ring in these condensed systems may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents D ⁶ R ⁶⁵ , where
  D ³ , D ⁴ , D ⁵ and D ^{6 are} each independently and a direct bond, oxygen, S (O) _k , SO ₂ O, OSO ₂ , CO, OCO, COO, SO ₂ NR ⁶⁶ , NR ⁶⁶ SO ₂ , NR ⁶⁶ O, ONR ⁶⁶ , NR ⁶⁶ , NR ⁶⁶ CO, CONR ⁶⁶ or SiR ⁶⁷ R ⁶⁸ mean and k = 0, 1 or 2; and
  R ⁵⁶ , R ⁵⁷ , R ⁶⁴ and R ⁶⁵ each independently of one another hydrogen, cyano, nitro, halogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₂ -C ₈ ) - Alkenyl, (C ₂ -C ₈ ) haloalkenyl, (C ₂ -C ₈ ) alkynyl, (C ₂ -C ₈ ) haloalkynyl, (C ₁ -C ₈ ) alkoxy (C ₁ -C ₄ ) alkyl , (C ₁ -C ₈ ) haloalkoxy (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) alkylthio (C ₁ -C ₄ ) alkyl, (C ₁ -C ₈ ) haloalkylthio, ( C ₁ -C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ - C ₈ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkyl, ( C ₄ -C ₈ ) - Cycloalkenyl- (C ₁ -C ₄ ) -alkyl, aryl, heterocyclyl, aryl- (C ₁ -C ₄ ) -alkyl or heterocyclyl- (C ₁ -C ₄ ) -alkyl, where in the latter 8 radicals, the cycloaliphatic, aromatic or heterocyclic ring systems are unsubstituted or can be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁶⁹ , where
  R ⁶⁶ are independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl and
  R ⁶⁷ and R ⁶⁸ independently of one another are (C ₁ -C ₄ ) -alkyl, and
  R ⁶⁹ independently of one another (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro, halogen, Can be (C ₁ -C ₄ ) alkanoyl or (C ₂ -C ₄ ) haloalkanoyl, or two of the radicals
  R ⁵⁶ , R ⁵⁷ , R ⁶⁴ , R ⁶⁵ , R ⁶⁹ , which are located on the same C atom, together and each independently represent an oxo group.

2. Compounds of formula I according to claim 1, in which
A CH and DN⁺R
or
A is nitrogen and D is N + R;
R ^{1 is} hydrogen, methyl, fluorine or chlorine;
R ² and R ^{3 are} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, amino, (C ₁ -C ₄ ) alkylamino, ( C ₁ -C ₄ ) dialkylamino, trimethylsilylethynyl, methoxycarbonyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or
R ² and R ³ together with the carbon atoms to which they are attached form an optionally substituted unsaturated 5- or 6-membered ring which, in the case of the 5-ring, may contain a sulfur atom instead of a CH ₂ unit; or
R ² and R ³ together with the carbon atoms to which they are attached form a saturated 5- or 6-membered ring which can contain a sulfur or an oxygen atom instead of a CH ₂ unit;
X means NH or oxygen. 3. A compound of formula I according to claim 1 or 2, in which
Y is a bond or a methylene group which is optionally substituted with one or two (C ₁ -C ₄ ) alkyl radicals; and
Z is optionally substituted as in claim 1 (C ₃ -C ₆ ) cycloalkyl or (C ₅ - C ₈ ) cycloalkenyl;
Y is a bond; and
Z (a) represents a group of formula II
wherein X ^{1 is} oxygen;
R ^{y is} (C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals listed are unsubstituted or with bis to three, in the case of fluorine also up to the maximum number of identical or different radicals and in the alkyl, alkenyl or alkynyl radicals mentioned one or more non-adjacent saturated carbon units can be replaced by heteroatom units, where R ²⁷ and R ^{28 are} (C ₁ -C ₄ ) -alkyl, and in addition 3 to 6 atoms of these hydrocarbon radicals, optionally modified as above, can form a cycle and these hydrocarbon radicals with or without the stated variations, optionally with one or more identical or different radicals from the series halogen, aryl, aryloxy, arylthio, (C ₃ - C ₈₎ cycloalkoxy, (C ₃ -C ₈₎ -cycloalkylthio, heterocyclyl, heterocyclyloxy or (C ₁ -C ₂₎ - Alkoxycarbonyl may be substituted k where the cycloaliphatic, aromatic or heterocyclic ring systems can be unsubstituted under the just mentioned substituents or can be provided with up to three, in the case of fluorine also up to the maximum number of identical or different substituents,
or R ^y and R ^z together form a five- or six-membered ring system in which a CH ₂ group can be replaced by heteroatom units, where R ^{29 is} hydrogen (C ₁ -C ₈ ) -alkyl, (C ₁ - C ₈ ) -alkanoyl, benzoyl, aryl or heteroaryl, it being possible for the benzoyl, aryl or heteroaryl radicals to be unsubstituted or provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents, and that Ring system formed from R ^y and R ^z can be unsubstituted or provided with up to three substituents and these substituents are identical or different and are each (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, aryl or aryl - (C ₁ -C ₄ ) -alkyl, where the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted under the just mentioned substituents or may be provided with up to three in the case of fluorine, up to the maximum number of identical or different substituents,
or the ring system formed from R ^y and R ^z together with a further benzene ring or cyclohexane ring forms a condensed ring system, and the benzene ring in these condensed systems is unsubstituted or provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents can be and
R ^z means hydrogen
or

• b) is a group of the formula (III)
  wherein
  Y ¹ , Y ² and Y ^{3 are} a group of the formula -O-, -S (O) _r -, where r = 0, 1 or 2 or a group of the formula CR ³¹ R ³² , or Y ¹ or Y ³ stand in the place of a direct bond, whereby
  R ³¹ and R ^{32 are} independently hydrogen or methyl;
  m ^{1 represents} 1 or 2;
  n ^{1 represents} 1 or 2;
  Z ^{1 is} a direct bond, NR ³³ , O, S (O) _s with s = 0, 1 or 2, OSO ₂ , SO ₂ O, NR ³⁴ SO ₂ , SO ₂ NR ³⁵ , SiR ³⁶ R ³⁷ or
  means where
  U is a direct bond, NR ³⁸ or O;
  W represents oxygen;
  V represents a direct bond, NR ³⁹ or oxygen;
  and
  R ³⁶ and R ^{37 are} (C ₁ -C ₄ ) alkyl or phenyl;
  R ³³ , R ³⁴ , R ³⁵ , R ³⁸ and R ^{39 are the} same or different and are each hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) - Is alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
  R ^{q is} mutually independent (C ₁ -C ₈ ) -alkyl, in which one or more non-adjacent saturated carbon units can be replaced by oxygen, and with or without the stated variations, optionally with one or more identical or different radicals D ¹ R ⁴³ may be substituted, or
  R ^q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ² R ⁴⁴ ;
  D ¹ and D ^{2 are} each independently and a direct bond, -O-, -S (O) _k -, -SO ₂ O-, -OSO ₂ -, -CO-, -OCO-, -COO-, - NR ⁴⁶ -, -SO ₂ NR ⁴⁶ , -NR ⁴⁶ SO ₂ -, -ONR ⁴⁶ -, -NR ⁴⁶ O-, -NR ⁴⁶ CO-, -CONR ⁴⁶ and k = 0.1 or 2, and in which
  R ^{46 is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
  R ⁴³ and R ⁴⁴ independently of one another denote hydrogen, halogen, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, aryl or heterocyclyl, the cycloaliphatic, aromatic or heterocyclic ring systems being unsubstituted in the latter 3 radicals or can be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R ⁴⁹ , where
  R ^{49 is} independently (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro, halogen can;
  or,
• c) is a group of the formula IV
  wherein
  Y ^{4 represents} a direct bond or CH ₂ ;
  Z ^{2 represents} oxygen;
  R ^{u represents} hydrogen, (C ₁ -C ₄ ) alkyl, tirfluoromethyl or (C ₁ -C ₄ ) alkoxy;
  W ^{1 means} direct bond, oxygen, -CO-, -COO-, CONR ⁵² , sulfur, -C = N-, -C = NO- and R ^{52 is} hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) - Alkanoyl and (C ₃ -C ₅ ) cycloalkyl means, and
  R ^{t is} as defined under (12c) above.

4. A compound of formula I according to any one of claims 1 to 3, in which
R ^{1 represents} hydrogen;
R ² and R ^{3 are} hydrogen, methyl, ethyl, propyl, methoxy, (C ₂ -C ₃ ) alkenyl, amino, (C ₁ -C ₄ ) alkylamino, (C ₁ -C ₄ ) dialkylamino, (C ₂ -C ₃ ) -chloro or -fluoro-alkenyl, (C ₂ -C ₃ ) -alkynyl, trimethylsilylethynyl, (C ₁ -C ₃ ) -chloro or -fluoroalkyl, methoxymethyl, halogen or cyano; or
R ² and R ³ together with the ring system to which they are attached form the quinazoline or quinoline system, which may be substituted by fluorine in the carbocyclic part; or
R ² and R ³ together with the carbon atoms to which they are attached form a saturated 6-membered ring which may contain an oxygen or sulfur atom instead of a CH ₂ group. 5. A compound of formula I according to any one of claims 1 to 4, in which
R ^{1 represents} hydrogen;
R ^{2 is} methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (C ₁ -C ₂ ) fluoroalkyl or methoxymethyl;
R ^{3 is} fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C ₁ -C ₂ ) fluoroalkyl, amino, (C ₁ -C ₂ ) alkylamino, (C ₁ -C ₂ ) dialkylamino or methoxy; or if A is nitrogen;
R ² and R ³ together with the ring system to which they are attached form the quinazoline system, which can be substituted with a fluorine atom. 6. A compound of formula I according to any one of claims 1 to 5, in which
X represents NH;
Y represents a bond; and
Z means (a) cyclopentyl or cyclohexyl, where both radicals can optionally be substituted as in (10) above
or

• b) denotes a group of the formula II,
  wherein
  X ^{1 represents} oxygen;
  R ^{z represents} hydrogen;
  or
• c) denotes a group of the formula III,
  wherein
  Y ^{1 represents} CH ₂ ;
  Y ^{2 represents} CH ₂ ;
  Y ^{3 represents} CH ₂ , O or a direct bond;
  m means ¹ 1
  or
• d) represents a group of the formula IV,
  wherein
  Y ^{4 represents} a direct bond or CH ₂ ;
  Z ^{2 represents} oxygen;
  R ^{u means} hydrogen or methyl.

7. A compound of formula I according to any one of claims 1 to 6, in which
Z (a) means cyclohexyl, which, if appropriate, as in (10) above
or

• b) denotes a group of the formula (II),
  wherein
  X ^{1 represents} oxygen;
  R ^{z represents} hydrogen;
  R ^{y is} (C ₁ -C ₁₅ ) alkyl, aryl or heterocyclyl in the sense of heteroaromatic ring system, the aryl or heterocyclyl radical being unsubstituted or having up to three, in the case of fluorine, up to the maximum number of identical or different radicals can be provided and in the alkyl radical mentioned one or more non-adjacent saturated carbon units can be replaced by oxygen, and in addition 3 to 8 atoms of this optionally modified alkyl radical can form a cycle and this alyl radical with or without the specified variations, optionally with one or more halogen atoms, in the case of fluorine also up to the maximum number of identical or different substituents,
  or
• c) denotes a group of the formula (III),
  wherein
  n ^{1 represents} 1 or 2;
  R ^{q is} independently of one another (C ₁ -C ₈ ) -alkyl, in which one or more non-adjacent saturated carbon units can be replaced by oxygen, and with or without the stated variations, optionally with one or more identical or different radicals D ¹ R ⁴³ may be substituted, or
  R ^q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ² R ⁴⁴ ;
  or
• d) is a group of the formula IV
  wherein
  R ^{u represents} hydrogen;
  R ^t denotes (C ₁ -C ₈ ) -alkyl, in which one or more non-adjacent saturated carbon units can be replaced by oxygen, and with or without the stated variations, optionally with one or more, preferably up to three, in the case of fluorine up to a maximum number of identical or different radicals D ³ R ⁶⁶ may be substituted, or
  R ^t can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ⁴ R ⁵⁷ .

8. A compound of formula I according to any one of claims 1 to 7, in which
A CH and DN⁺R
or
A represents nitrogen and DN⁺R;
R ^{4 represents} hydrogen;
R ^{5 is} hydrogen, halogen, cyano, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl;
R ⁶ denotes aryl or heteroaryl, where the aryl and heteroaryl radicals can optionally be substituted by one or more identical or different radicals Z ^{1 '} -R ^q' , where
Z ¹ , a direct bond, O, OSO ₂ or
means where
U 'is a direct bond, or O;
W 'represents oxygen;
V 'represents a direct bond, NR ^39' or oxygen;
and
R ^{39 'represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
R ^{q '} are mutually independent substituents and is (C ₁ -C ₂₀ ) -alkyl or (C ₂ -C ₂₀ ) -alkenyl and can optionally be substituted by one or more identical or different radicals D ^1' R ^{43 '} , or
R ^{q 'is} halogen, hydroxy, nitro or cyano, or
R ^{q 'can be} aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ^{2' 44 '} ;
D ^{1 '} and D ^{2' are} each independent of one another and a direct bond, -O-, -S (O) _k -, -SO ₂ O-, -OSO ₂ -, -CO-, -OCO-, -COO- , -NR ^{46 '} -, -SO ₂ NR ^46' -, -NR ^{46 '} SO ₂ -, -ONR ^46' -, -NR ^{46 '} O-, -NR ^46' CO-, -CONR ^{46 '} - means, and k = 0, 1 or 2, and wherein
R ^{46 'is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
R ^{43 '} and R ^44' independently of one another are hydrogen, halogen (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, aryl or heterocyclyl, the cycloaliphatic, aromatic or heterocyclic ring systems in the latter 3 radicals unsubstituted or with up to three, in the case of fluorine also up to the maximum number of identical or different substituents R ^{49 '} , where
R ^{49 '} independently of one another (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro, halogen means. 9. A compound of formula I according to any one of claims 1 to 8, in which
R ^{1 represents} hydrogen;
R ^{2 represents} ethyl or methoxymethyl;
R ^{3 represents} chlorine, bromine or methoxy;
R ^{4 represents} hydrogen;
R ^{5 represents} hydrogen;
R ⁶ denotes aryl or heteroaryl, where the aryl and heteroaryl radicals can optionally be substituted by one or more identical or different radicals Z ^{1 '} -R ^q' , where
Z ^{1 'is} a direct bond, O or
means where
U 'is a direct bond, or O;
W 'represents oxygen;
V 'represents a direct bond, NR ^39' or oxygen;
and
R ^{39 'represents} hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
Z ^{1 '} -R ^q' together represent halogen, nitro or cyano, or
R ^{q '} are mutually independent substituents and is (C ₁ -C ₁₂ ) alkyl or (C ₂ -C ₁₂ ) alkenyl and can optionally be substituted by one or more identical or different radicals R ^43' , or
R ^{q 'can be} aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ^2' R ^{44 '} ;
D ^{2 are} each independent of one another and a direct bond, -O-, -S (O) _k -, -SO ₂ O-, -OSO ₂ -, -CO-, -OCO-, -COO-, -NR ^{46 '} -, -SO ₂ NR ^46, -, -NR ^46' SO ₂ -, -ONR ^{46 '} -, -NR ^46' O-, -NR ^{46 '} CO-, -CONR ^46' - means, and k = 0 , 1 or 2, and wherein
R ^{46 'is} independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkanoyl or (C ₃ -C ₅ ) cycloalkyl;
R ^{43 '} and R ^44' independently of one another are hydrogen, cyano, nitro, halogen, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, aryl or heterocyclyl, the cycloaliphatic radicals in the last 3 radicals mentioned , aromatic or heterocyclic ring systems unsubstituted or provided with up to three, in the case of fluorine also up to the maximum number of identical or different substituents R ^{49 '} , where
R ^{49 '} independently of one another (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, cyano, nitro, halogen can be. 10. A process for the preparation of a compound of formula I according to any one of claims 1 to 9, characterized in that a compound of formula (V)
wherein G is CH or N and R ¹ , R ² , R ³ , X, Y and Z have the meanings given under formula I, with an electrophile of the formula (VI),
wherein R ⁴ , R ⁵ , R ⁶ and E have the meaning given under formula I and L represents a leaving group, optionally with the addition of salts and the anion of the compound of formula I obtained in this way is replaced by other anions. 11. Means containing at least one compound according to one of the claims 1 to 9 and at least one formulation agent. 12. Fungicidal composition according to claim 11 containing a fungicidally active Amount of at least one compound according to one of Claims 1 to 9 together with the usual additives for this application. 13. Insecticidal, acaricidal or nematicidal agent according to claim 11, containing an effective amount of at least one compound according to one of the Claims 1 to 9 together with the additional or customary for these applications Auxiliary materials. 14. Plant protection products containing a fungicide, insecticide, acaricide or nematicidal amount of at least one compound according to one of the Claims 1 to 9 and at least one further active ingredient, preferably from the Range of fungicides, insecticides, attractants, sterilants, acaricides, nematicides and Herbicides together with the auxiliary and common for this application Additives. 15. Agents for use in wood protection or as a preservative in Sealants, in paints, in cooling lubricants for metalworking or in drilling and cutting oils containing an effective amount of at least one A compound according to any one of claims 1 to 9 together with those for it Applications usual auxiliaries and additives. 16. A compound according to any one of claims 1 to 9 or means according to claim 11, for use as a veterinary medicinal product, preferably for combating Endo or ectoparasites. 17. A method for producing an agent according to any one of claims 11 to 15, characterized in that the active ingredient and the other additives together and brings it into a suitable form of application.   18. Use of a compound according to any one of claims 1 to 9 or Agent according to one of claims 11, 12, 14 and 15 as a fungicide. 19. Use of a compound according to any one of claims 1 to 9 or an agent according to any one of claims 11, 12 and 15 as a wood preservative or as a preservative in sealants, in paints, in cooling lubricants for metalworking or in drilling and cutting oils. 20. Process for combating phytopathogenic fungi, thereby characterized in that one looks at this or the plants infested by them, Surfaces or substrates or on seed a fungicidally effective amount of A compound according to any one of claims 1 to 5 or an agent according to one of claims 7, 8, 10 and 14 applied. 21. Procedures for controlling insect pests, acarina and nematodes, at which one on these or the plants, areas or infested by them Substrates an effective amount of a compound according to any one of claims 1 to 9 or an agent according to any one of claims 11, 13 and 14 applied. 22. Use of compounds according to one of claims 1 to 9 or an agent according to any one of claims 11, 13 and 14 for combating Insect pests, acarina and nematodes. 23. Seeds treated or coated with an effective amount of one A compound according to any one of claims 1 to 9 or an agent according to one of claims 11, 12, 14 and 15.