WO1999059978A1

WO1999059978A1 - Substituted nitrogen heterocycles and their use as pesticides

Info

Publication number: WO1999059978A1
Application number: PCT/EP1999/003092
Authority: WO
Inventors: Ralf Braun; Harald Jakobi; Matthias Eckhardt; Gerhard Krautstrunk; Oswald Ort; Wolfgang Schaper; Ulrich Sanft; Maria-Theresia Thönessen; Bonin Bonin
Original assignee: Aventis Cropscience Gmbh
Priority date: 1998-05-20
Filing date: 1999-05-06
Publication date: 1999-11-25
Also published as: GB9810860D0; AU4037599A

Abstract

Compounds of formula (I), in which A is CH and D is N+R; or A is nitrogen and D is N+R; or A is N+R and D is nitrogen, where R is CR?4R5DaR6, Qn-¿ is an inorganic or organic anion, n being 1, 2, 3 or 4; X, Y, Z, and R?1, R2 and R3¿ have various meanings as defined in the claims, are useful pesticidal, especially insecticidal activity.

Description

SUBSTITUTED NITROGEN HETEROCYCLES AND THEIR USE AS

PESTICIDES

The invention relates to novel substituted pyridines and pyrimidines and condensed systems derived therefrom, processes for their preparation and their use as pesticides, especially insecticides and acaricides.

It is already known that certain 4-amino- and 4-alkoxy-heterocycles have fungicidal, acaricidal and insecticidal activity (for example WO-A-93/19 050, DE-A-43 43 250, WO-A-95/07 890, WO-A-94/21 613). However, the biological activity of these compounds, in particular at low application rates and concentrations, is not satisfactory in all use examples.

Novel, positively charged heterocycles of the formula I have been found

/^γ-^z

X

in which the radicals and groups are as defined below, which, while showing good tolerance by plants and favourable toxicity in respect of warm-blooded animals, are highly suitable for controlling insects and acarids.

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

(1) A is CH and D is N⁺R or

A is nitrogen and D is N⁺R or

A is N⁺R and D is nitrogen, where

R is CR R⁵D^aR⁶, (2) Qⁿ" is an inorganic or organic anion, n being 1 , 2, 3 or 4;

(3) R¹ is hydrogen, halogen, (C-i-Csr-alkyl, (C_π-C8)-haloalkyl, (C_π-C8)-alkoxy or

(C₃-C₆)-cycloalkyl;

(4) R² and R³ are identical or different and are each hydrogen, (Ci-Csr-alkyl,

(C2-C8)-alkenyl, (C2-C8)-alkynyl, (C-j-CβJ-alkoxy, halogen, hydroxy, cyano, nitro, thiocyanato, (C-i-Cβr-alkoxycarbonyl, (C_π-C8)-alkylthio,

(C-|-C8)-alkylsulfinyl, (C-j-CsJ-alkylsulfonyl, amino; (C-i-C_βr-alkylamino,

(C-j-CβJ-dialkylamino or (C3-C6)-cycloalkyl, and in which in the alkyl, cycloalkyl, alkenyl, alkynyl groups or the groups derived from them, such as alkoxy, alkylfyl, alkanoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, a saturated carbon unit can be replaced by a hetero atom unit such as oxygen, S(O)_x, where x = 0, 1 or 2 or by dimethylsilyl and further in these groups or derived groups up to 3 hydrogen atoms can be replaced by halogen and in the case of fluorine also all hydrogen atoms can be replaced by fluorine; or

R2 and R³ together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered carbocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH2, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C-J-C4)- alkyl, (C_η-C4)-haloalkyl, preferably trifluoromethyl, halogen, (C1-C4)- alkoxy or (Cι-C4)-haloalkoxy; or

R² and R³ together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered carbocyclic ring which may contain oxygen and/or sulfur instead of one or two CH2 groups and which may be substituted by 1, 2 or 3 (C-|-C4)-alkyl groups; (5) X is O, S(O)_q where q = 0, 1 or 2, NR⁷, NR CO, NR⁷CS or CR⁸R⁹, where R⁷ is hydrogen and R⁸ and R⁹ independently of one another are each hydrogen or (C_π_C4)-alkyl,

(6) Y - Z together are a (C₁-C2θ)-hy^drocarDθn radical which is straight-chain or branched and in which one or more, preferably up to three, CH2 may be replaced by hetero atom radicals such as O, NR¹⁰, S, SO, SO2 or

SiR^{1 1}R¹², where R¹⁰ is hydrogen, (C_π-C4)-alkyl or (C-_|-C4)-acyl, and

R¹¹ and R¹² are identical or different and are each independently of the other (C-|-C4)-alkyl, phenyl or substituted phenyl, and where this (C_π-C2θ)-hydrocarbon radical with the possible abovementioned variations may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of (C-i-CyJ-alkyl,

(C2-C4)-alkenyl,

(C2-C4)-alkynyl,

(C3-C7)-cycloalkyl,

(C3-C7)-cycloalkenyl, halogen, halo-(C_π-C4)-alkyl, halo-(C-|-C4)-alkoxy, hydroxy and

(C_π-C4)-acyl; or, if not included in the above definitions,

(7) Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms which may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of

(C^CyJ-alkyl,

(C2-C4)-alkenyl,

(C₃-C₇)-alkynyl,

(C3-C7)-cycloalkyl,

(C3-C7)-cycloalkenyl, halogen, halo-(C-|-C4)-alkyl, halo-(C-_|-C4)-alkoxy, hydroxyl and

(8) Z is aryl or O-aryl, where aryl is preferably a naphthyl or phenyl group, heterocycyl or heterocyclyloxy, each of which may be substituted by one or more, preferably up to five, in particular up to three, identical or different radicals selected from the group consisting of halogen, (C3-C8)-cycloalkyl,

(C3-C8)-cycloalkenyl , phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, optionally substituted heterocyclyl, optionally substituted heterocyclylthio

NO₂,

-C(O)-R¹³, acetoxy, hydroxyl, cyano,

SiRl R¹⁵R¹⁶,

O-SiR¹⁴R¹⁵R¹⁶,

NR17_R18

S(O)R¹⁹, SO₂R¹⁹,

(C2-Ci2)-alkenyl, (Cι-Ci2)-^a'koxy and (Ci-C-^r-alkyltt-i⁰; and R¹³ is (C-_|-C7)-alkyl, halo-(C-|-C7)-alkyl, (C3-C7)-cycloalkyl, halo-

(C-C7)-cycloalkyl, (Cι-C7)-alkoxy, phenyl or substituted phenyl;

R¹⁴, R^η5 and R^η6 are identical or different and are each independently of one another (C-|-C4)-alkyl, phenyl and/or substituted phenyl;

R¹⁷ and R¹⁸ are identical or different and are each independently of the other hydrogen, (C_π-C4)-alkyl and/or (C<|-C4)-acyl;

R¹⁹ is (C_π-Cιo)-^a'kyl, phenyl or substituted phenyl; wherein (C-|-C-|2)-alkyl, (Ci-C^J-alkoxy, (Cη-C-^r-alkylthio and (C2-C_π2)-alkenyl one or more, preferably up to 3, CH2 groups may be replaced by hetero atom radicals such as O, S, SO, SO₂, R10' or SiRU'Rl²'; _R10'_ _R11" _{and R}12' _have the meanings of R¹⁰, R^{1 1} , R¹²; the (Ci-C^J-alkyl radical with or without the abovementioned variations may also be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group below consisting of halogen, halo-(Cι-C4)-alkoxy, hydroxyl, (C3-C8)- cycloalkyl, (C3-C8)-cycloalkenyl, (Cι-C4)-acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (C-|-C7)-alkoxy and (C1-C7)- alkylthio radicals, one or more, preferably up to three, CH2 groups may be replaced by O, and these radicals may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, phenyl, substituted phenyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, phenoxy and substituted phenoxy; or, if not included in the above definitions,

(9) Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms, preferably methylene, which is substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of

(C-i-CyJ-alkyl.

(C2-C4)-alkenyl,

(C₃-C₇)-alkynyl,

(C3-C7)-cycloalkyl,

(C3-C7)-cycloalkenyl, halogen, halo-(C-_j-C4)-alkyl, halo-(Cι-C4)-alkoxy, hydroxyl and (C_π-C4)-acyl; and

(10) Z is (C3-C8)-cycloalkyl or (C5-C8)-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR²^;

R20 j_s phenyl or substituted phenyl and the (C3-C8)-cycloalkyl or (C5- C_βJ-cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (Cι-C ₈)-alkyl,

(C3-C8)-cycloalkyl,

(C3-C8)-cycloalkoxy,

(C₂-C₁₈)-alkenyl,

(C₂-C₁₈)-alkynyl,

(C-_|-C-|2)-alkoxy,

(Cι-C-|2)-alkanoyloxy, formyl, (C₂-C₁₂)-acyl,

(C-_|-C-_|2)-alkoxycarbonyl,

SiR²l R²²R²³,

NR²⁴R 5,

C(O)NR²⁴R²⁵, hydroxyl, halogen, aryl, heteroaryl,

O aryl,

O heteroaryl,

CH2θaryl,

CH2θheteroaryl,

(C_π-Ci8)-alkanediyldioxy,

(C_η-C 3)-alkoximino and

(C2-C-|8.-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH2 groups in the (Cι_C-|8h (C2-C-18)-. (C-|.C-|2)"> (C2-C-|2r- ^and (C-|-C-|3)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as O, NR^π0" or SiR^{η ι}"R^{l 2}", these hetero atom radicals preferably not being adjacent to one another, where R¹⁰", R^{1 1}" and R¹²" have the meanings of R¹⁰,

R¹1, R¹² and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, optionally substituted heterocyclyl, phenylthio and substituted phenylthio; where heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R²⁴ and R ^ are identical or different and are each independently of the other hydrogen, (C-_|-C4)-alkyl, (C_π-C4)-acyl, (C3-

Ce)-cycloalkyl, phenyl and substituted phenyl and where R²¹, R²²,

R²³ are identical or different and are each independently of the others (Cι-Ci8)-alkyl, (C-_|-C-_|8)-alkoxy, (C3-C8)-cycloalkyl and aryl, where in the (Cι-Ci8)-hydrocarbon radicals more than one, preferably up to three, non-adjacent CH2 groups may be replaced by oxygen and where

3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it also being possible for two of the carbon radicals (for example R²¹ and

R²²) attached to silicon together to form a cycle, the silicon atom in this case being a ring atom of this cycle, and where additionally these (Cι-C-_|8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the cycloalkyl or cycloalkenyl radicals defined under (10) may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1 ,4 position, preference is given to the cis configuration; or

(11) Y is a bond; and

(12) Z is (a) a group of the formula II

where each X^"1 independently of the other is sulfur or oxygen; R^z is hydrogen, (C_π-C4)-alkyl, trifluoromethyl or (C-|-C4)-alkoxy; or

Ry is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x, where x = 0, 1 or 2, NR²⁶ or SiR²⁷R²⁸, where R²⁶ is hydrogen, (C_η-C4)-alkyl, (C_π-C4)-alkoxy or (C_π-C4)-alkanoyl and R²⁷ and R²⁸ are each (C-_|-C4)-alkyl, preferably methyl; and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as mentioned above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkyl- alkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyanato or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where R and R^z together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the hetero atoms χ1 and where one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2 or NR²⁹, where R²⁹ is hydrogen, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by Ry and R^z may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, aralkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry 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, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; in particular those groups of the formula II where

Ry is (C-|-C2θ)-^alkyl, (C2-C2θ)-^a'kenyl, (C2-C2o)"^alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x, where x = 0, 1 or

2, NR²⁶ or SiR²⁷R²⁸ where R²⁶ is hydrogen, (C_π-C4)-alkyl,

(C-j-C4)-alkoxy or (C<_|-C4)-alkanoyl and R²⁷ and R²⁸ are each

(C_η-C4)-alkyl, preferably methyl, and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, (C3-C8)- cycloalkoxy, (C3-C8)-cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio,

(C3-C8)- cycloalkanoyl, (C2-C_π2)-haloalkanoyl, aroyl, aryl-(C_π-C4)- alkanoyl, (C3-C8r-cycloalkyl-(C-|-C4)-alkanoyl, heterocyclyl-(C_η-

C4)-alkanoyl, (C-|-C-j2)-alkoxycarbonyl, (C-1-C12)- haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C3-C8)- cycloalkyl-(C_π-C4)-alkoxycarbonyl, aryl-(C-j-C4)-alkoxycarbonyl, heterocyclyl-(C-|-C4)-alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, (C_π-C<i2r-alkanoyloxy, (C2-C12)- haloalkanoylalkoxy, (C3-C8)-cycloalkanoyloxy, (C3-C8)- cycloalkyl-(Cι-C4)-alkanoyloxy, aroyloxy, aryl-(C-_|-C4)-alkanoyl- oxy, heterocyclyl-(C-|-C4)-alkanoyloxy, (Cι-Ci2.-alkyl- sulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyanato or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where Ry and R^z together form a three- to eight-membered ring system, which is spirocyclically linked to the ring system containing the hetero atoms χ1 and where one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2 or NR²⁹, where R²⁹ is hydrogen, (C-|-C8)-alkyl, (C-|-C8)-alkoxy, (C-i-C_β)- alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents and where the ring system formed by Ry and R^z may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C-i-Cs)- alkyl, (C-j-CβJ- aloalkyl, (Cη-CβJ-alkoxy, (C-j-CsJ-alkylthio, (C3-

C8)-cycloalkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkylthio, aryl, aryloxy, arylthio, aryl-(C_π-C4)-alkyl, aryl-(C-_|-C4)-alkoxy, aryl-

(C-j-C4)-alkylthio, heterocycyl, heterocyclyloxy, heterocyclylthio,

(C-)-C8)-trialkylsilyl, preferably (C-|-C8)-alkyldimethylsilyl, or

(C_π-C8)-alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and R^z, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydro- naphthalene, decahydronaphthalene or benzocycloheptane system and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where among the compounds where the carbon atom between the hetero atoms X^ carries only the substituent Ry, the substituents X and Ry are preferably cis to each other;

R^z is hydrogen, (C-_|-C4)-alkyl, trifluoromethyl or (C-_|-C4)-alkoxy; or

(b) a group of formula

where

Y^π, Y² and Y³ independently of one another are each a group of the formula -O-, -CO-, -CNR³⁰-, -S(O)_r where r = 0, 1 or 2,

-N(O)|R³⁰- where I = 0 or 1 or a group of the formula CR³¹R³²; or γ1 or Y³ stands in place of a direct bond, where

R30 J_S hydrogen, (C-|-C4)-alkyl, (C-|-C4)-haloalkyl, (C₂-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (C_π- C4)-alkoxy, (C_π-C4)-haloalkoxy,

(C_π-C4)-halo- alkylthio, (Cη-C^-alkanoyl, (C2-C4)-haloalkanoyl, (C3-C5)- cycloalkyl, (C_π-C4)-alkylsulfonyl, (C<|-C4)-haloalkylsulfonyl, (C_π -C4)-alkoxy-(C-| -C4)-alkyl, (C-| -C4)-alkoxycarbonyl;

R31 and R³² independently of the other are each hydrogen, hydroxyl, halogen, cyano, (C-|-C4)-alkyl, (Cι-C4)-haloalkyl, (C2-C4)- alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkenyl, (C3-C5)-cycloalkyl, (C-|-C4)-alkanoyl, (C-1-C4)- haloalkanoyl,

(C_π-C4)-haloalkoxy, (C1-C4)- alkylthio or (C_π-C4)-haloalkylthio; m¹ is 0, 1, 2, 3 or 4, preferably 1 or 2; n¹ is 0, 1 , 2, 3 or 4, preferably 1 or 2; Z¹ is a direct bond, NR³³, O, S(O)_s where s = 0, 1 or 2, OSO2,

SO₂O, NR³ SO₂, SO₂NR³⁵, SiR³⁶R³⁷ or

U-C(W)-V, where R36 _and R37 _{are eaC} (C_η-C4)-alkyl or phenyl, preferably methyl;

U is a direct bond, NR³⁸ or O;

W is oxygen or sulfur, preferably oxygen;

V is a direct bond, NR³⁹ or oxygen, where R33 R34 R35 R38 _and R³⁹ are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;

R°. are substituents which are independent of one another and each is halogen, cyano, nitro, (Cι-C2θ)-alkyl, (C2-C2o)-alkenyl,

(C2-C2o)-3lkynyl, (C3-C₈)-cycloalkyl, (C4-C8)-cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x where x = 0, 1 or 2, NR⁴⁰ or SiR⁴¹R⁴² and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D¹R⁴³, or

R°. is aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D²R⁴⁴, or two adjacent radicals zl-R⁰- may combine with the carbon atoms to which they are attached to form a fused cycle having 4 to 6 ring atoms which is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C-_|-C4)-alkyl and oxo, or

R³³, R³^ or R³⁹ independently of one another may combine with the

R°. located at Z to form a 4- to 8-membered ring system in which one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)t_ι where t =

0, 1 or 2 or NR⁴⁵, where

R⁴⁰ is hydrogen, (C_π-C4)-alkyl, (C-|-C4)-alkoxy or (C-|-C4)-alkanoyl;

R⁴1 and R⁴² independently of the other are each (C<_|-C4)-alkyl, preferably methyl; D¹ and D² are independent of each other and each is a direct bond, oxygen, S(O)_k, SO₂O, OSO₂, CO, OCO, COO, NR⁴⁶,

SO₂NR⁴⁶, NR⁴⁶SO₂, ONR⁴⁶, NR ⁶O, NR ⁶CO, CONR⁴⁶ or

SiR⁴⁷R⁴⁸, and k = 0, 1 or 2, where R46 independently of the others is hydrogen, (C_π-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl;

R⁴⁷ and R⁴⁸ independently of the other are each (C-|-C4)-alkyl; R⁴³ and R⁴⁴ independently of the other are each hydrogen, cyano, nitro, halogen, (C<|-C8)-alkyl, (C_π-C8)-haloalkyl, (C2-C8)- alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)- haloalkynyl, (C₁-C8)-alkoxy-(C-|-C4)-alkyl, (C-_|-C8)-haloalkoxy- (Cι-C4)-alkyl. (C<\-Cs)-a\ky o-(C C₄)-a\\<s/\, (Cη-Cβ)- haloalkylthio-(C-|-C4)-alkyl, (C3-C8)-cycloalkyl, (C4-C8)- cycloalkenyl, (C3-C8)-cycloalkyl-(C_π-C4)-alkyl, (C4-C8)- cycloalkenyl-(C-|-C4)-alkyl, aryl, heterocyclyl, aryl-(C-_|-C4)-alkyl or heterocyclyl-(C-|-C4)-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁴⁹, or R43 and R⁴⁴ located at the same carbon atom together are an oxo group, where

R⁴⁹ is (Cι-C )-alkyl, (C₁-C₄)-haloalkyl, (C-_|-C4)-alkoxy, (C-_|-C )- haloalkoxy, cyano, nitro or halogen;

R⁴⁵ is hydrogen, (C-_j-CsJ-alkyl, (C_π-C4)-haloalkyl, (C-|-C4)-alkoxy,

(C_π-C4)-alkylthio, (C3-C5)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)- alkynyl, (C_π-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C2-C4)- alkoxyalkyl, phenyl-(C-|-C4)-alkyl or phenyl where the phenyl groups may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^O, where

R⁵⁰ is (Cι-C₄)-alkyl, (C_π-C4)-haloalkyl, (C-i^-alkoxy, (C-j^)- alkylthio, halogen or cyano; or, if not included in the above definitions,

(c) is a group of the formula IV

where

Y⁴ is a direct bond or CH2;

Z² is oxygen, NR⁵¹ , S(O)_m where m = 0, 1 or 2;

R^U and wl-Rt are substituents of the heteroaliphatic ring system, where

R^u is hydrogen, halogen, cyano, (C<|-C4)-aIkyl, (C-_|-C4)-haloalkyl,

(C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkynyl, (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C-1-C4)- alkoxy, (C-|-C4)-haloalkoxy, (C-i^J-alkanoyloxy, (C-1-C4)- haloalkanoyloxy, (C-|-C4)-alkylthio or (C-_|-C4)-haloalkylthio;

W is a direct bond, oxygen, -NR⁵²-, -CO-, -COO-, CONR⁵²-, sulfur, -C=N-, -C=N-O- or -NR⁵²O-;

R* is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x where x = 0, 1 or 2, NR⁵³ or SiR⁵ R⁵⁵, and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D³R⁵⁶, or

R* may be aryl or heterocyclyl, where both of these radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D⁴R⁵⁷ or

R^u and R* together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the hetero atoms Y⁴ and Z² and in which one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2, or NR⁵⁸, where

R51 j_s hydrogen, (Cf-C^alkyl, (C-_|-C4)-haloalkyl, (C2-C4)-alkenyl,

(C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (C_π-

C4)-alkoxy, (C_π-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C1-C4)- alkoxy- (C_π-C4)-alkyl, (C_π-C4)-alkylthio-(C-|-C4)-alkyl, (C1-C4)- alkoxycarbonyl, (C-|-C4)-alkylsulfonyl,

phenylcarbonyl, phenyl-(C_π-C4)-alkyl or phenyl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁵⁹, or

R⁵¹ is CONR⁶⁰R⁶¹ where

R6° and R^6<l independently of the other are each hydrogen, (C-1-C4)- alkyl or phenyl, where the phenyl group may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^², and R⁶² and R⁵⁹ independently of the other are each (C₁-C4)-alkyl, (C-|-

C4)-haloalkyl, (C-|-C4)-alkoxy, (Cι-C4)-haloalkoxy, (C-1-C4)- alkylthio or halogen; R52 J_S hydrogen, (C_η-C4)-alkyl, (C-j-O^-alkanoyl or (C3-C5)-cycloalkyl; R53 J_S hydrogen, (C«_|-C4)-alkyl, (C-|-C4)-alkoxy or (C_π-C4)-alkanoyl;

R⁵⁴ and R⁵⁵ independently of the other are (C-|-C4)-alkyl, preferably methyl;

R58 j_S hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^³;

R⁶³ may be (C-|-C4)-alkyl, (C_π-C4.-haloalkyl, (C_π-C4)-alkoxy, (C-1-C4)- haloalkoxy, cyano, nitro or halogen, and the ring system formed by R^u and R* may be unsubstituted or substituted by up to three, but preferably one, substituents D⁵R⁶⁴, or the ring system formed by R^u and R , together with a further 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 may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D⁶R⁶⁵, where

D³, D⁴, D⁵ and D⁶ are independent of one another and are each a direct bond, oxygen, S(O)|<, SO2O, OSO2, CO, OCO, COO,

SO₂NR⁶⁶, NR⁶⁶SO₂, NR⁶⁶O, ONR⁶⁶, NR⁶⁶, NR⁶⁶CO, CONR⁶⁶ or SiR⁶⁷R⁶⁸, where k = 0, 1 or 2; and R56₍ R57_J R64 _and R⁶⁵ independently of one another are each hydrogen, cyano, nitro, halogen, (Ci-CsJ-alkyl, (Cη-Cs)- haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (C-j-C8)-alkoxy-(C₁-C4)-alkyl, (C-i-C_β)- haloalkoxy-(C-|-C4)-alkyl, (C₁-C8)-alkylthio-(C₁-C4)-alkyl, (C<_|-C8)-haloalkylthio-(C-_|-C4)-alkyl, (C3-C8)-cycloalkyl, (C4- C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C-|-C4)-alkyl, (C4-C8)- cycloalkenyl-(C-|-C4)-alkyl, aryl, heterocyclyl, aryl-(C₁-C4)-alkyl or heterocyclyl-(Cι-C4)-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁶⁹, where

R⁶⁶ independently of the others is hydrogen, (C_π-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and

R^⁷ and R⁶⁸ independently of the other are each (C_π-C4)-alkyl, and

R6⁹ independently of the others may be (C-ι-C4)-alkyl, (C1-C4)- haloalkyl, (C-|-C4)-alkoxy, (C-|-C4)-haloalkoxy, cyano, nitro, halogen, (C-|-C4)-alkanoyl or (C2-C4)-haloalkanoyl, or two of the radicals R⁵⁶, R⁵⁷, R⁶⁴, R⁶⁵, R⁶⁹ which are located at the same carbon atom together, and in each case independently of the others, are an oxo group; in particular those groups of the formula IV where

R^l is hydrogen, (Cι-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C3-

C8)-cycloalkyl or (C4-C8)-cycloalkenyl and where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x where x = 0, 1 or 2,

NR⁵³ or SiR⁵⁴R⁵⁵, and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D³R56 ₀r

R may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D⁴R⁵⁷ or

R^u and R* together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms Y⁴ and Z², and in which one CH2 group may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2 or NR⁵⁸, where R53 J_S hydrogen, (Cι-C4)-alkyl, (C_π-C4)-alkoxy or (C_π-C4)-alkanoyl and R⁵⁴ and R⁵⁵ independently of the other are (Cι-C4)-alkyl, preferably methyl;

R58 J_S hydrogen, (C-_|-C8)-alkyl, (C-_|-C8)-alkanoyl, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^³, and

R⁶³ may be (C-|-C4)-alkyl, (C_π-C4)-haloalkyl, (C_π-C4)-alkoxy,

(C-_|-C4)-haloalkoxy, cyano, nitro or halogen, and the ring system formed by R^u and R* may be unsubstituted or substituted by up to three, but preferably one, substituents

ΓJ5R64_I or the ring system formed by R^u and R*, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydro- naphthalene, decalin or benzocycloheptane system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D⁶R⁶⁵, where in the compounds where the carbon atom between Y⁴ and Z² where Y = CH2 only carries the substituent W^R*, the substituents X and W^R* are cis to each other;

SO₂NR⁶⁶, NR⁶⁶SO₂, NR⁶⁶O, ONR⁶⁶, NR⁶⁶, NR⁶⁶CO or

CONR⁶⁶, and k = 0, 1 or 2, R66 independently of the others is hydrogen, (C-_|-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and

R56_ R57 R64 _and R^5 independently of one another are each hydrogen, cyano, nitro, halogen, preferably fluorine, (C-i-Cs)- alkyl, (C3-C8)-cycloalkyl, aryl, heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁶⁹, where R⁶⁹ independently of the others may be (C-|-C4)-alkyl, (C1-C4)- haloalkyl, (C_π-C4)-alkoxy, (C-j-C4)-haloalkoxy, cyano, nitro, halogen, or two of the radicals R56_ R57 R64 R65 R69 which are located at the same carbon atom, together and in each case independently of the others, are an oxo group; (13) R⁴ is a) hydrogen, halogen or optionally substituted alkyl or

(b) a negative charge, which can represent Qⁿ"

(14) R⁵ is hydrogen, halogen, CN, nitro, (C_π-C4)-alkoxycarbonyl, (C1-C4)- alkylcarbamoyl, di-(C_η-C4)-alkylcarbamoyl, (C-j-CsJ-alkoxy, (C-j-C_β)- alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, aryl or (C3-C₈)-cycloalkyl;

(15) D^a is c) a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SO₂, C(=W^a), OC(=W^a) or d) U^a(C=W^a)V^a (U^a and V^a are a direct bond, NR⁷⁰, S or O, except V^a is not a bond when U^a is bond or O), SiR⁷²R⁷³, U^b(P=W^b)V V^c, U^b(SO2)U^c (one of U^b and U^c is a direct bond, NR⁷⁰, S or O and the other is NR⁷⁰), U^a(CW^a)(CW^a)V^b, NR⁷⁰O, O NR⁷⁰, NR⁷⁰ NR⁷⁰,

N=N, -N=, - NR⁷⁰-N= or -O-N= , and

W^a is O, S or NR⁷¹;

W^b is O or S;

U^a, V^b and V^c, independently of each other are a direct bond, NR⁷⁰, S or O each R⁷⁰, which may be the same or different from any other R⁷⁰, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted a ino, optionally substituted acyloxy, and may also form a 4 to 8 membered with R⁶, Rl ^{I 2} or R1 ^{I 3}, respectively with the Da, D^"!² or. D^{π 3} to which they are attached, and in the case D^a is U^bP(=W^b)V^bV^c, the two R⁶ groups together with the V^bPV^c, to which they are attached can form a 4 to 8 membered ring

each R⁷¹ , which may be the same or different from any other R⁷¹ , is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;

R⁷² and R⁷³ are alkyl or optionally substituted aryl; (16) R⁶ is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to three CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR⁷⁰ or Si R⁷²R⁷³ and can also be substituted by nitro, halogen, SF5 or D¹²R^{1 12} and in the case D^a is U^bP(=W^b)V V^c, the two R⁶ groups together with the V PV^c, to which they are attached can form a 4 to 8 membered ring

D ² is e) a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SiR ²R⁷³, U'(CW)V, or f) U¹'(PW ^,)V^{1 ,}V^2, _I U²'(SO₂)U³', Si(OR⁷²)R⁷³, Si(OR⁷²)(OR⁷³),NR⁷⁰O,

ONR⁷⁰, NR⁷⁰NR⁷⁰, N=N, =N-, =N-NR70- =N-O-, -N=, -NR⁷⁰-N= or - O-N= and

U',1)¹' V, V¹' and V²', independently of each other are a direct bond,

NR⁷⁰, S or O

W' is O, S or NR⁷ ;

W ' is O or S;

U²' and U³', independently of each other are a direct bond, NR⁷⁰ or O;

(g) R^{1 π2} is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2,

NR⁷⁰ or SiR⁷²R⁷³ and can also be substituted by nitro, halogen, SF5 or D^{l 3}R^{π 13} and in which two adjacent D¹²Rl1² together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C-_|-C4-alkyl; or

(h) R1¹² is a negative charge for D¹² = (CO)O, (SO₂)O, U¹'(PW')V¹'θ which replaces the ion Qⁿ-; or R ¹² is hydrogen for D¹² = O(CO)NH, NR ⁰(CO)NH, O(CS)NH, NR⁷⁰(CS)NH, (CO)NH, (CS)NH, O(CO), NR⁷⁰(CO), SO2NH;

D^{l 3} has the same meaning as D^l2 and R^{π π 3} has the same meaning as Rl 1 ; and in paragaraphs (13) - (16), aryl is as defined under (8) and, if it is not encompassed by the definition the carbon containing groups named under (13) to (16) can be substituted by one or more, preferably up to three (in the case of halogen up to the maximim number) of the same or different groups selected from halogen, cycloalkyl, phenoxy, substituted phenoxy, phenyl or substituted phenyl, with the proviso that at least one of the parameters defined in 13b, 15d or 16f or 16h applies.

An inorganic anion is an anion of an inorganic acid, for example F-, CI-, Br-, I-, NO3-,

SO4²-, HSO4-, PO4³-, HPO4²-, H2PO4-, PO3³- or N3-, or a complex anion, for example BF4-, PF_β- or tetraphenylborate.

An organic anion is an anion of an organic acid (carboxylic acid, sulfonic acid, phosphonic acid and the like) or an aromatic or heteroaromatic phenol-like compound. These are, for example, anions of mono- or bifunctional carboxylic acids and carboxylic 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, and sulfonic acids such as p-toluenesulfonic acid, dodecylsulfonic acid or 1 ,5-naphthalenedisulfonic acid, or saccharin.

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

If Z is (C3-C8)-cycloalkyl or (Cs-CβJ-cycloalkenyl, it is preferably substituted by one or more, preferably up to 3, identical or different substituents selected from the group consisting of (C<|-Ci2)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C-|-C4)-alkyl, (C-_|-

C8)-alkoxy, (C3-C8)-cycloalkoxy, (C-|-C4)-alkoxy-(C₁-C4)-alkyl, (C3-C8.-cycloalkyl-

(C₁-C4)-alkoxy, tri-(C-|-C8)-alkylsilyl, preferably dimethyl-(C_π-C8)-alkylsilyl or triethylsilyl, di-(C-|-C8)-alkyl-(C3-C8)-cycloalkylsilyl, preferably dimethylcyclohexylsilyl, di-(C-_|-C8)-alkyl-(phenyl-(C_π-C4)-alkyl)-silyl, preferably dimethyl(phenyl-(C-_|-C4)- alkyl)silyl, di-(C_π-C8)-alkyl-(Cι-C4)-haloalkylsilyl, preferably dimethyl-(C-|-C4)- haloalkylsilyl, dimethylphenylsilyl), (C-j-Cs. -haloalkyl, halogen, (C-j-C4)-haloalkoxy, heteroaryl, phenyl, phenyl-(Cι-C4)-alkyl, benzyloxy, benzyloxy-(C-_|-C4)-alkyl, benzylthio, phenylthio and phenoxy, where heteroaryl or phenyl in the last eight radicals may be unsubstituted or substituted by one or two substituents, these substituents being identical or different and being in each case (C<_|-C8)-alkyl, (C3-

CβJ-cycloalkyl (Cι-C4)-haloalkyl, preferably trifluoromethyl, halogen, (C1-C4)- dialkylamino, (C-|-C4)-alkylthio, (C-j-Csr-alkoxy, (C_π-C4)-haloalkoxy, (C_η-C4)-alkoxy-

(C₁-C4)-alkoxy, H5C2-O-[CH2-CH2-O-]_x, 2-(tetrahydro-2H-pyran-2-yloxy)ethoxy,

(C2-C8)-alkenyl, (C2-C8)-alkynyl, benzyloxy, which may carry one or two identical or different substituents selected from the group consisting of (C«|-C4)-alkyl, (C-1-C4)- haloalkyl, (C_π-C4)-alkoxy, (C_π-C4)-haloalkoxy and halogen in the phenyl moiety, tri-

(Cι-C4)-alkylsilylmethoxy, preferably dimethyl-(Cι-C4)-alkylsilylmethoxy, (C3-C8)- cycloalkyl-(C-|-C4)-alkoxy, 1,3-dioxolan-2-ylmethoxy, tetrahydrofuran-2-ylmethoxy and tetrahydro-2H-pyran-2-ylmethoxy.

Preferred compounds of formula I are those in which

R1 is hydrogen, halogen, (C-|-C4)-alkyl, (C_π-C4)-haloalkyl or (C3-C5)-cycloalkyl;

R² and R³ are identical or different and are each hydrogen, (C-|-C4)-alkyl, (C1-C4)- haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkynyl, trimethylsilylalkynyl, (C_η-C4)-alkoxy, (C<|-C4)-haloalkoxy, (C₁-C4)-alkoxy-(C₁-C4)-alkyl, (C-|-C4)-haloalkoxy-(C-_|-C4)-alkyl, (C1-C4)- alkoxy-(C-|-C4)-haloalkyl, (C-_|-C4)-haloalkoxy-(C_π-C4)-haloalkyl, halogen, hydroxy, (C-|-C4)-hydroxyalkyl, (C_π-C4)-alkanoyl, (C<|-C4)-haloalkanoyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, cyano, (C-|-C4)-cyanoalkyl, nitro, (C-_|-C4)-nitroalkyl, thiocyanato, (C-|-C4)-thiocyanatoalkyl, (C1-C4)- alkoxycarbonyl, (C-|-C4)-alkoxycarbonyl-(C-_|-C4)-alkyl, (C1-C4)- haloalkoxycarbonyl, (C_π-C4)-alkylthio, (C-|-C4)-alkylthio-(C-_|-C4)-alkyl, (C_π- C4)-haloalkylthio, (C_π-C4)-alkylsulfinyl, (Cι-C4)-haloalkylsulfinyl, (C1-C4)- alkylsulfonyl (Cι-C4)-haloalkylsulfonyl; amino, (C-ι-C4)-alkylamino or C-_j- C4)-dialkylamino

R² and R³ together with the linking carbon atoms form an unsaturated 5- or 6- membered carbocyclic ring which, if it is a 5-membered ring, may contain an oxygen or sulfur atom in the place of a CH2 or which, or which may, if it is a

6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C_π-C4)-alkyl,

preferably trifluoromethyl, halogen, (C-|-C4)-alkoxy or (C_π-C4)-haloalkoxy; or

R² and R³ together with the linking carbon atoms form a 5-, 6- or 7-membered alicyclic ring which may contain oxygen and/or sulfur in the place of one or two carbon ring members and which is, if desired, substituted by 1 , 2 or 3 (C-j-C4)-alkyl groups;

Preferred compounds of formula I also are those in which

A is CH and D is N⁺R or

A is nitrogen and D is N⁺R;

Q^n_ is an anion such as Hal", NO3", BF4", BPh4" or PFQ~;

It is also preferred that

Rl is hydrogen, methyl, fluorine or chlorine;

R² and R³ are each hydrogen, (C-_|-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, amino, (Cι-C4)-alkylamino, (C-ι-C4)-dialkylamino, trimethylilylethynyl, methoxycarbonyl, (C-|-C4)-haloalkyl, (C2-C4)-haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or

R² and R³ join with the linking carbon atoms to form an unsaturated 5- or 6- membered ring with or without substitution which may, in the case of the 5- membered ring, contain a sulfur atom instead of a CH2 unit; or

R² and R³ join with the linking carbon atoms to form a saturated 5- or 6-membered ring, which may contain a sulfur or oxygen atom instead of a CH2 unit;

X is NH or oxygen.

Other preferred compounds are those I in which

Y is a bond or a methylene group which is substituted by one or two, preferably by one, (C-|-C4)-alkyl radical; and Z is (C3-C8)-cycloalkyl or (Cs-CsJ-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR²⁰;

R20 J_S phenyl or substituted phenyl and the (C3-Cs)-cycloalkyl or (C5-C8)- cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (C«|-C₁₈)-alkyl,

(C3-C8)-cycloalkyl,

(C3-C8)-cycloalkoxy,

(C₂-C₁₈)-alkenyl,

(C₂-C₁₈)-alkynyl,

(C_π-Ci2)-alkoxy,

(Cη-C-^-alkanoyloxy, formyl, (C₂-C₁₂)-acyl,

SiR²¹R²²R²³, NR²⁴R²5,

CONR² R²⁵, hydroxy, halogen, aryl, heteroaryl,

O aryl,

O heteroaryl,

CH2θaryl,

CH2θheteroaryl,

(C-_|-C-|8)-alkanediyldioxy,

(C-_|-C-|3)-alkyloximino and

(C2-C-|8)-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH2 groups in the (C«|-C_π8)-. (C2-C18)-, (C1-C12)-. (C2-C12)- and (Cι-C-|3)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as O, NR^{π 0}" or

SiR^{1 '}' "R^{I 2} ", these hetero atom radicals preferably not being adjacent to one another, where R¹⁰", R^{1 1}" and R¹²" have the meanings of R¹⁰, R^{1 1}, R¹² and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio; where heteroaryl is unsubstituted or may be substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R²⁴ and R²⁵ are identical or different and are each independently of the other hydrogen, (C<_|-C4)-alkyl, (C-_|-C4)-acyl, (C3-C6)-cycloalkyl, phenyl and substituted phenyl and where R²¹, R²², R²³ are identical or different and are each independently of the others (C-|-C<_|8)-alkyl, (C-|-C-|8)-alkoxy, (C3_C8)-cycloalkyl and aryl, where in the (C-_|-C-_|8)-nydrocarbon radicals more than one, preferably up to three, CH2 groups may be replaced by oxygen and where 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it also being possible for two of the carbon radicals (for example R²^ and R²²) attached to silicon together to form a cycle, the silicon atom possibly being part of this cycle, and where additionally these (C-|-C_n8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the (C3-C8)-cycloalkyl or (Cs-CsJ-cycloalkenyl radicals defined above may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1 ,4 position, preference is given to the cis configuration; or

Y is a bond; and

Z (a) is a group of the formula II

where X¹ is oxygen;

Ry is (C₁-C2θ)-alkyl, (C2-C2θ)-alkenyl, (C2-C2θ)-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by hetero atom units such as oxygen or SiR²⁷R²⁸, where R²⁷ and R²⁸ are each (C₁-C4)-alkyl, preferably methyl, and where additionally 3 to 6 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle, and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably by up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, preferably fluorine, aryl, aryloxy, arylthio, (C3-C8)-cycloalkoxy, (C3-

CsJ-cycloalkylthio, heterocyclyl, heterocyclyloxy or (C-_|-C2)-alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or Ry and R^z together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms χ1 , and where one CH2 group may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2 or NR²⁹, where R²⁹ is hydrogen, (C_η-C8)-alkyl, (C-_|-C8)-alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by Ry and R^z may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C-|-C8)-alkyl, (C3-C8)-cycloalkyl, aryl or aryl-(C_π-C4)- alkyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry 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, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where in the compounds where the carbon atom between the hetero atoms X^"l only carries the substituent Ry, the substituents X and Ry on the heteroaliphatic six-membered ring are preferably cis to each other; and is hydrogen or (b) is a group of the formula (III)

where

Y¹ , Y² and Y³ are each a group of the formula -O-, -S(O)_r, where r = 0, 1 or 2 or is a group of the formula CR^3lR³² , or Y¹ or Y³ stands in place of a direct bond, where

R31 and R³² independently of the other are each hydrogen or methyl; m¹ is 1 or 2; n¹ is 1 or 2;

Z1 is a direct bond, NR³³, O, S(O)_s where s = 0, 1 or 2, OSO2, SO2O,

NR³⁴SO₂, SO₂NR³⁵, SiR³⁶R³⁷ or U-C(W)-V, where

U is a direct bond, NR³⁸ or O; W is oxygen;

V is a direct bond, NR³⁹ or oxygen; and R36 and R³⁷ are each (C_π-C4)-alkyl or phenyl, preferably methyl;

R³³, R34_ R35 R38 _and R³⁹ are identical or different and are each hydrogen, (C-_|-C4)-alkyl, (C-|-C4)-alkoxy, (C-|-C4)-alkanoyl or (C3-C5)-cycloalkyl;

R°. independently of the others is (Cι-Cs)-alkyl where one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen and which, with or without the variations mentioned, may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D R⁴³, or

R⁰. may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D²R⁴⁴;

D^"! and D² are independent of one another and are each a direct bond, -O-,

-S(O)_k-, -SO₂O-, -OSO₂-, -CO-, -OCO-, -COO-, -NR⁴⁶-, -SO₂NR⁴⁶-,

-NR ⁶SO₂-, -ONR⁴⁶-, -NR⁴⁶O-, -NR⁴⁶CO-, -CONR⁴⁶-, and k = 0, 1 or 2, and where R46 independently of the others is hydrogen, (C-_|-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl;

R43 and R44 independently of the other are each hydrogen, halogen, preferably fluorine, (C-|-C8_. -alkyl, (C3-C8)-cycloalkyl, aryl or heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R4⁹, where R⁴⁹ independently of the others may be (C₁-C4)-alkyl, (C_π-C4)-haloalkyl,

(C-_|-C4)-alkoxy, (Ci-C4)-haloalkoxy, cyano, nitro, halogen; or,

(c) is a group of the formula IV

where

Y⁴ is a direct bond or CH2;

Z² is oxygen;

R^u is hydrogen, (C_π-C4)-alkyl, trifluoromethyl or (C_η-C4)-alkoxy;

W¹ is a direct bond, oxygen, -CO-, -COO-, CONR⁵², sulfur, -C=N-,

-C=N-O- where R⁵² is hydrogen, (C-|-C4)-alkyl, (C-|-C4)-alkanoyl and (C3-C5)-cycloalkyl, and

R* is as defined above under (12 c).

Particularly preferred are those compounds of formula I in which

Rl is hydrogen;

R² and R³ are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3)-alkenyl, amino, (C_π-C4)-alkylamino, (C-|-C4)-dialkylamino, (C2-C3)-chloro- or - fluoroalkenyl, (C2-C3)-alkynyl, trimethylsilylethynyl, (C-_|-C3)-chloro- or - fluoroalkyl, methoxymethyl, halogen or cyano; or

R² and R³ together with the ring system to which they are attached form the quinazoline or quinoline system, which may be fluorine-substituted in the carbocyclic moiety; or

R² and R³ 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 CH2 group;

Especially preferred compounds are those compounds where R1 is hydrogen;

R² is methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (C-_|-C2)-fluoroalkyl or methoxymethyl; R³ is fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C-_|-C2)-fluoroalkyl, amino,

(C-_|-C2)-alkylamino, (C_π-C2)-dialkylamino or methoxy; or, in the case that A is nitrogen,

R² and R³ form, together with the ring system to which they are attached, the quinazoline system, which may be substituted by one fluorine atom.

Other preferred compounds are those in which

X is NH;

Y is a bond; and

Z is (a) cyclopentyl or cyclohexyl, where both radicals may be substituted as above under (10) and where, in the case of cyclohexyl, 1 ,4-substitution is preferred, the substituents being cis to one another; or

(b) is a group of the formula II

where χ1 is oxygen;

R^z is hydrogen; or

(c) is a group of the formula

where

Y¹ is CH₂;

Y² is CH₂;

Y³ is CH2, O or a direct bond; m¹ is 1 or

(d) is a group of the formula IV

where

Y⁴ is a direct bond or CH2;

Z² is oxygen;

R^u is hydrogen or methyl;

in particular those compounds where

Z (a) is cyclohexyl which is preferably substituted by a radical selected from the group consisting of

(C-i-C-βJ-alkyl,

(C₃-C₈)-cycloalkyl,

(C3-C8)-cycloalkoxy,

(C2-C8)-alkenyl,

(C₂-C₈)-alkynyl,

(C-i-Csr-alkoxy,

(C-|-C8)-alkoxycarbonyl,

SiR²lR²²R²³,

-CO-NR² R²⁵, aryl, heteroaryl,

O aryl,

O heteroaryl,

CH2θaryl,

CH2θheteroaryl,

(C_η-C8)-alkanediyldioxy and

(C-|-C-|3)-alkyloximino, where this substituent is in position 4 of the cyclohexyl ring and cis with respect to the -(X-Y)- unit and where, if not included in the definitions above, one or more, preferably up to three, CH2 groups in the (C-i-Cβ)-, (C2-C8)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals, such as O, or SiR^"! 1"R^l2", where R^{ι π}" and R^π2" have the meanings of R^{1 1}, R^{l 2}, and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, and where these hydrocarbon radicals with or without the variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl; heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; aryl is as defined under (8);

R²⁴ and R²⁵ are identical or different and independently of one another are each hydrogen, (C-|-C4)-alkyl, phenyl and substituted phenyl, and R ^ , R²², R²³ are identical or different and independently of one another are each (C-|-Cg)-alkyl, (C-|-C8)-alkoxy, (C3-C8)- cycloalkyl and aryl, where in the (C<_|-C8)-hydrocarbon radicals more than one, preferably up to three, CH2 groups may be replaced by oxygen and 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it being possible for the silicon atom to be part of this cycle, and where additionally these (C-|-C8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl; or (b) is a group of the formula (II)

where

X¹ is oxygen; R^z is hydrogen;

Ry is (C- -Ci5)-alkyl, aryl or heterocyclyl meaning a heteroaromatic ring system, where the aryl or heterocyclyl radical may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl radical mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and where additionally 3 to 8 atoms of this alkyl radical, which may be modified as above, may form a cycle, and where this alkyl radical with or without the variations mentioned may be substituted by one or more halogen atoms (in the case of fluorine up to the maximum number of identical or different substituents), and where the substituents X and Ry on the heteroaliphatic six-membered ring are preferably cis to one another; or (c) is a group of the formula (III)

where nl is 1 or 2;

R°. independently of the others is (Cι-Cs)-alkyl where one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and which with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D¹ R⁴³, or

R°. may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number), identical or different radicals D²R⁴⁴; or (d) is a group of the formula IV

where

R^u is hydrogen;

R* is (C_π-C8)-alkyl in which one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and which with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D³R⁵6 or

R* may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D R⁵⁷.

Most particularly preferred are those compounds of the formula I in which

R¹ is hydrogen;

R² is ethyl or methoxymethyl; and

R³ is chlorine, bromine or methoxy, preferably those for which R² is ethyl and R³ is chlorine; Other preferred compounds are those where

R4 and R⁵, which may be the same or different, are hydrogen, halogen, nitro, cyano, a negative charge, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heterocyclyl or optionally substituted cycloalkyl.

Particularly preferred are those compounds where

R is hydrogen, halogen, nitro, cyano, a negative charge, optionally substituted C-_|-C20-alkyl, optionally substituted C2-C20-alkenyl, optionally substituted

C2^_C20"^a,kynyl, and R⁵ is hydrogen, halogen, nitro, cyano, optionally substituted C-|.C20"^a'kyl. optionally substituted C2-C20-^a'kenyl, optionally substituted C2-C20"^a'kyⁿyl. optionally substituted aryl, and optionally substituted Cs-Cg-cycloalkyl.

Especially preferred are compounds where

R⁴ is hydrogen, halogen, C-|-C4-alkyl or a negative charge if R⁵ = COR⁵', and

R⁵ is hydrogen, halogen, C-j-Cβ-alkyl, Ci-Cβ-haloalkyI, C2-C8-alkenyl, C2-C8-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C_π-C4-alkyl, aryl, C-_j-Cβ-alkoxy, (CO)R⁵' where R⁵' is Cη-Cβ-alkoxy or NR⁵"R⁵'", in which R⁵" and R⁵'", which may be the same or different, are hydrogen or C_π-C8 alkyl or the two groups can form a ring in which optionally a CH2 is replaced by O, S or NR5"" with R5"" = C-_|- C4-alkyl, hydrogen or phenyl.

Generally

R⁴ is hydrogen and

R⁵ is hydrogen or methyl

It is also preferred that

D^a is a direct bond, NR⁷⁰, O, S, SO, SO2 or U^a(CW^a)V^a, and especially a direct bond, NR⁷⁰, O, S, O(CO), NR⁷⁰(CO), (CO) or (CNR⁷""), preferably a direct bond, S, NR⁷⁰(CO),O(CO) or (CO).

Preferred compounds also are those where

R ³ is hydrogen, cyano, C-|-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C_η-C_β-alkoxy-

Cι-C4-alkyl, C-|-C8-alkylthio-C«|-C4-alkyl, C3-C8-cycloalkyl, C4-C8- cycloalkenyl, C3-C8-cycloalkyl-C-|-C-alkyl, C4-C8-cycloalkenyl-C_π-C4-alkyl, aryl, aryl-C_π-C4-alkyl, heterocyclyl, heterocyclyl-Cι-C4-alkyl, in which the carbon containing can be substituted by one or more, preferably up to three, and in the case of halogen up to the maximum number of the same different groups selected from nitro, halogen cyano, hydroxy or R^η1⁴, in which

R^{1 4}is C-j-C4-alkyl, Cι-C4-haloalkyl, C-|-C4-alkoxy, C<|-C4-haloalkoxy; or R¹¹³ is a negative charge when D¹³ = (CO)O, (SO2)O, U1"(PW1")V1"O, which replaces Qⁿ"; each R⁷⁰, which may be the same or different from any other R⁷⁰, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyloxy, and optionally and may also form a 4 to 8 membered with R⁶, R^{1 12} or R^{l 13}, respectively with the Da, D¹² or. D¹³ to which they are attached, and each R⁷¹, which may be the same or different from any other R^7π, is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;

R⁷² and R⁷³ are alkyl or optionally substituted aryl; and especially

R⁶ is cyano, C-|-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C8-cycloalkyl, C4-C8- cycloalkenyl, aryl or heterocyclyl, in which up to three CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR⁷⁰ or Si R⁷²R⁷³ and these groups or their variations can also be substituted by up to three and in the case of halogen up the maximum number, of the same or different groups selected from nitro, halogen, SF5 or D^²R^{1 12} and these groups and their named variations should also be substituted by one or more of the same or different _D12'_R112 j_{n w}hj_Ch

D¹² is a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SiR⁷²R⁷³, U'fCWJV, U¹'(PWT)V V²', U²'(SO₂)U³', Si(OR⁷²)R⁷³, Si(OR⁷²)(OR⁷³),NR ⁰O,

ONR⁷⁰, NR⁷⁰NR⁷⁰, N=N, =N-, =N-NR⁷⁰-, =N-O-, -N=, -NR ⁰-N= or -O-N= and

U',U¹' V, V¹' and V²', independently of each other are a direct bond, NR⁷⁰, S or O,

W is O, S or NR⁷¹;

W¹' is O or S; U²' and U³', independently of each other are a direct bond, NR⁷⁰ or O; and D¹²' is N(O)R⁷⁰, SiOR⁷²R⁷³, SiOR⁷²OR⁷³, U'(CNR⁷ )V', S(CW')V, U'(CW')S,

U1'(PW¹')V¹'V²', U²'(SO₂)U³', NR⁷⁰O, ONR⁷⁰, NR⁷⁰NR⁷⁰, N=N, =N-, =N-

NR⁷⁰-, =N-O-, -N=, -NR⁷⁰-N=, -O-N=, or D¹²' is COO or SO2O on which R^{1 12} is a negative charge or hydrogen, or

D¹²' is O(CO)NH, NR⁷⁰(CO)NH, O(CS)NH, NR ⁰(CS)NH, (CO)NH, (CS)NH, O(CO), NR⁷⁰(CO), SO₂NH in which R^{1 12} is hydrogen;

U' and U¹', independently of each other, are a direct bond, NR⁷⁰, S or O

W is O, S or NR⁷¹

W¹' is O or S

V, V¹' and V²', independently of each other, are a direct bond, NR⁷⁰, S or O'

U²' and U³', independently of each other, are NR⁷⁰ or O

R 12 j_s hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR⁷⁰ or

SiR⁷²R⁷³ and can also be substituted by nitro, halogen, SF5 or

D13R113 and in which two adjacent D1²/D¹²'R^{1 12} together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C«|-C4-alkyl; or

(h) R^{1 12} is a negative charge for D ²' = (CO)O, (SO₂)O, U¹'(PW¹')V¹O which replaces the ion Q^n_; or R11² is hydrogen for D¹²' = O(CO)NH, NR ⁰(CO)NH, O(CS)NH, NR⁷⁰(CS)NH, (CO)NH, (CS)NH, O(CO), NR⁷⁰(CO), SO2NH;

D^{l 3} has the same meaning as D¹² and R^{1 13} has the same meaning as Rl ²; R112 j_s hydrogen, cyano, C-|-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C8- cycloalkyl, C4-C8-cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR⁷⁰ or SiR⁷²R⁷³ and can also be substituted by up to three, in the case of halogen up to the maximum number, of the same or different nitro, halogen, SF5 or D¹³R^{1 13} and in which two adjacent groups D¹²/D¹²'R^{1 12} with or without the named variations together with the carbons to which they are attached can form a condensed 4 bis 6 membered ring which can optionally be substituted with halogen or C-|-C4-alkyl; or

R ¹² is a negative charge when D¹²' = (CO)O, (SO2)O, U1'(PWr)V1O which replaces Qⁿ"; D^³ is a direct bond, NR⁷⁰, O, S, (SO), SiR⁷²R⁷³, U"(CW")V", U¹"(PW1")V1"V²",

U²"(SO₂)U³", NR⁷⁰O, ONR⁷⁰, NR ⁰NR⁷⁰, N=N, =N-, =N-NR⁷⁰-, =N-O-, -

N=, -NR ⁰-N= or -O-N=,

U" and U¹", independently of each other, are a direct bond, NR⁷⁰, S or O, W" is O, S or NR'

W¹" is S,

V", V¹" and V²", independently of each other, are a direct bond, NR⁷⁰, S or O,

U²" and U³ ", independently of each other, are a direct bond, NR⁷⁰ or O;

R^{l 13} is hydrogen, cyano, C-|-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C-_|-C8-alkoxy- C«|-C4-alkyl, C-|-C8-alkylthio-C^«|-C4-alkyl, C3-C8-cycloalkyl, C4-C8- cycloalkenyl, C3-C8-cycloalkyl-C-|-C4-alkyl, C4-C8-cycloalkenyl-Cι-C4-alkyl, aryl, aryl-C-_|-C4-alkyl, heterocyclyl, heterocyclyl-C_η-C4-alkyl, and the carbon containing groups can also be substituted by up to three and, in the case of halogen up the maximum number, of the same or different nitro, halogen, cyano, hydroxy or R^{1 14}, in which R^{1 14} is C_π-C4-alkyl, C_η-C4-haloalkyl, C_π-C4-alkoxy, C-|-C4-haloalkoxy; or

R^{1 13} is a negative charge when D¹³ = (CO)O, (SO2)O, U¹(PW¹)VlO, which replaces Qⁿ";

Particularly preferred are compounds where

R® is C-|-C20-alkyl, aryl or heterocyclyl, in which these groups and their named variations can also be substituted by up to three and, in the case of halogen up the maximum number, of the same or different nitro, halogen, SF5 or rj12_R112 _ano; these groups and their named variations should also be substituted by one or more of the same or different D^{I 2}'R112_ j_n which _D12' JS _R70_ι SiOR⁷²R⁷³, SiOR⁷²OR⁷³,U'(CNR)V', S(CW')V, U'(CW)S,

U (PW^{1 ,})V V2^, _l U^2,(SO2)U³', NR⁷⁰O, ONR⁷⁰, NR⁷⁰ NR⁷⁰, N=N, =N-, =N-

NR⁷⁰-, =N-O-, -N=, -NR⁷⁰-N= or -O-N=, or D¹²'is COO or SO2O, in which R¹¹² is a negative charge or hydrogen, or

D ²' is O(CO)NH, NR⁷⁰,(CO)NH, O(CS)NH, NR ⁰(CS)NH, (CO)NH, (CS)NH, O(CO), NR⁷⁰(CO) or SO2NH, in which case R ² is hydrogen,

U' and U1', independently of each other, are a direct bond, NR⁷⁰, S or O,

W is O, S or NR⁷⁰,

W¹'is O or S,

V, V¹' and V²', independently of each other, are a direct bond, NR⁷⁰, S or O,

U²' and U³', independently of each other a direct bond, NR⁷⁰ or O,

Even more preferred are compounds where

R6 is aryl or heteroaryl, in which these groups and their named variations can also be substituted by up to three and, in the case of halogen up the maximum number, of the same or different nitro, halogen, SF5 or D^{l 2}R^"! ^{l 2}> and these groups and their named variations should also be substituted by one or more of the same or different D^π2 R¹1², in which

D¹² is a direct bond, O, U'(CW')V, U (PW^{1 ,})V V²', U²'(SO₂)U³', in which

U' and U1', independently of each other, are a direct bond or O, W is O or S ,

W'is O or S,

V, V^"1' and V²', independently of each other, are a direct bond, NR⁷⁰, S or O,

U²' and U³', independently of each other are a direct bond or O, or

D¹²' is U'(CW')S, U (PW¹')Vl'v²', U²'(SO₂)U³', or

D^l2' is COO or SO2O, in which R^{π π2} is a negative charged or hydrogen, or

D¹²' is O(CO)NH, NR⁷⁰(CO)NH, O(CS)NH, NR ⁰(CS)NH, (CO)NH, (CS)NH, O(CO), NR ⁰(CO) or SO2NH in which case R^{1 2} is hydrogen,;

U' and U¹', independently of each other.are direct bond or O, W is O or S

W¹' is O or S

V¹' or V²', independently of each other, are a direct bond, NR⁷⁰, S or O,

U²' is O, and

U³' is R⁷⁰ or O.

In the above formulae (I) to (IV), the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless specifically mentioned, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or, in the case of unsaturated groups, 2 to 6 carbon atoms, are preferred for these radicals, alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl radicals, hexyl radicals, such as n-hexyl, i-hexyl and 1 ,3-dimethylbutyl, heptyl radicals, such as n-heptyl, 1-methylhexyl and 1 ,4-dimethylpentyl; alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl.

Cycloalkyl is a carbocyclic saturated ring system preferably having 3 - 8 carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl, but also bicyclic systems, for example the norbornyl group, the bicyclo[2.2.2]octane radical and tricyclic systems, for example adamantyl.

Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example monohaloalkyl, perhaloalkyl, CF3, CHF2, CH2F,

CF₃CF₂, CH₂FCHCI, CCI3, CHCI₂, CH₂CH₂CI; haloalkoxy is, for example, OCF3,

OCHF₂, OCH2F, CF3CF2O, OCH2CF3 and OCH2CH2CI; the same applies analogously to haloalkenyl and other halogen-substituted radicals. A hydrocarbon radical is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl; preferably, a hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl; the same applies analogously to a hydrocarbon radical in a hydro- carbonoxy radical.

aryl is 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 (heterocycle) can be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, i.e. hetero atoms or ring members, including substituted hetero atoms, preferably selected from the group consisting of N, O, S, SO, SO2; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and it contains 1 , 2 or 3 hetero units. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl), for example a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more hetero atoms, 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, adjacent oxygen atoms being excluded, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or it is a partially or fully hydrogenated radical such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Substituents which are suitable for a substituted heterocyclic radical are the substituents mentioned further below, and additionally oxo. The oxo group can also be present on the hetero ring atoms, which can exist at various oxidation levels, for example in the case of N and S. Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl or heteroaryl, are, for example, a substituted radical derived from the unsubstituted skeleton, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkyl- sulfonyl and, in the case of cyclic radicals, also alkyl, cycloalkyl and haloalkyl; the term "substituted radicals" such as substituted alkyl etc. includes as substituents, in addition to the saturated hydrocarbon-containing radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy, etc., with or without substitution. Preferred among the radicals having carbon atoms are those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms. Preferred substituents are generally selected from the group consisting of halogen, for example fluorine and chlorine, (Cι-C4)-alkyl, preferably methyl or ethyl, (C<_j-C4)-haloalkyl, preferably trifluoromethyl, (C-_|-C4)-alkoxy, preferably methoxy or ethoxy, (C-_|-C4)-haloalkoxy, nitro and cyano. Especially preferred are the substituents methyl, methoxy and chlorine.

Mono- or disubstituted amino is a chemically stable radical selected from the group consisting of the substituted amino radicals which are N-substituted, for example by one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; preference is given to alkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; acyl is defined as indicated further below and is preferably (C_π-C4)-alkanoyl. The same applies analogously to substituted hydroxylamino or hydrazino.

Unsubstituted or substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals selected from the group consisting of halogen, (C-|-C4)-alkyl, (C-|-C4)-alkoxy,

(Cι-C4)-haloalkyl, (C_π-C4)-haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyl radicals, 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 radical is the radical of an organic acid, for example the radical of a carboxylic acid and radicals of acids derived therefrom, such as thiocarboxylic acid, iminocarboxylic acids with or without N-substitution, or the radical of carbonic monoesters, carbamic acid with or without N-substitution, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl is, for example, formyl, alkylcarbonyl such as [(C-j-C4)alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids. In each case, the radicals may be substituted even further in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents already mentioned further above in general for substituted phenyl.

Furthermore, in the above formulae the term "dimethyl-(C-|-C8)-alkylsilylethynyr denotes, for example, the trimethylsilylethynyl or the tert-butyldimethylsilylethynyl group; the term "(C_η-C4)-hydroxyalkyl" denotes, for example, the hydroxymethyl,

1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-1-methylethyl or the 1-hydroxypropyl group; the term "(C-|-C4)-alkanoyl" denotes, for example, the formyl, acetyl, propionyl,

2-methylpropionyl or butyryl group; the term "(C«|-C<_|2)-alkanoyl" denotes, for example, the abovementioned radicals and, for example, the valeroyl, pivaloyl, hexanoyl, decanoyl or the dodecanoyl group; the term "(C2-C4)-haloalkanoyl" denotes a (C-|-C4)-alkanoyl group in which the hydrogen atoms are partly, in the case of fluorine partly or wholly, replaced by halogen atoms, preferably fluorine or chlorine; the term "(C2-C_π2)-haloalkanoyl" denotes a (C-_|-C2o)-alkanoyl group in which the hydrogen atoms are partly, in the case of fluorine partly or wholly, replaced by halogen atoms, preferably fluorine or chlorine; the term "cyano-(C-|-C4)-alkyl" denotes a cyanoalkyl group whose hydrocarbon radical has the meanings given for the term "(C-|-C4)-alkyl"; the term "(C-_|-C4)-alkylamino" denotes, for example, methylamino, ethylamino, isopropylamino; the term "(C_π-C4)-dialkylamino" denotes, for example, dimethylamino, N-ethyl-N- methylamino, diethylamino, the term "(C₁-C4)-alkoxycarbonyl" denotes, for example, the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonyl group; the term "(C_π-Ci2)-alkoxycarbonyl" denotes the abovementioned radicals and, for example, the hexyloxycarbonyl, 2-methylhexyloxycarbonyl, decyloxycarbonyl or dodecyloxycarbonyl group; the term "(C-_|-C4)-haloalkoxycarbonyl" denotes a (C-|-C4)-alkoxycarbonyl group in which one or more, in the case of fluorine possibly all, hydrogen atoms are replaced by halogen, preferably fluorine or chlorine; the term "(C<_|-C4)-haloalkylthio" denotes a (C-|-C4)-alkylthio group in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine; the term "(Cι-C4)-alkylsulfinyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group; the term "(Cι-C4)-alkylsulfonyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group; the terms "(C₁-C4)-haloalkylsulfinyl" and "(C-|-C4)-haloalkylsulfonyl" denote (C-J-C4)- alkylsuifinyl and -sulfonyl radicals having the abovementioned meanings in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine; the term "(C_π-C4)-alkoxy-(C₁-C4)-alkyl" denotes, 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; the terms "(Cι-C4)-haloalkoxy-(C₁-C4)-alkyl", "(C₁-C4)-alkoxy-(Cι-C )-haloalkyr and

"(Cι-C4)-haloalkoxy-(C-_|-C4)-haloalkyl" denote (C«|-C4)-alkoxy-(Cι-C4)-alkyl radicals having the abovementioned meanings where one or more, in the case of fluorine possibly all, hydrogen atoms of the appropriate hydrocarbon moieties are replaced by halogen, preferably chlorine or fluorine; the term "(C-_|-C4)-alkylthio-(C-|-C4)-alkyr denotes, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or

3-methylthiopropyl; the term "arylthio" denotes, for example, the phenylthio or the 1- or 2-naphthylthio group; the term "aryloxy" denotes, for example, the phenoxy- or 1- or 2-naphthyloxy group; the term "heterocyclyloxy" or "heterocyclylthio" denotes one of the abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom; the term "cycloalkoxy" or "cycloalkylthio" denotes one of the abovementioned cycloalkyl radicals which are linked via an oxygen or sulfur atom; the term "aroyl" denotes, for example, the benzoyl, naphthoyl or the biphenylcarbonyl group; the term "aryl-(Cι-C4)-alkanoyl" denotes, for example, the phenylacetyl,

3-phenylpropionyl, 2-phenylpropionyl, 2-methyI-2-phenylpropionyl, 4-phenylbutyryl or the naphthylacetyl group; the term "(C3-C8)-cycloalkyl-(C_π-C4)-alkanoyl" denotes, for example, the cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclohexylacetyl or the cyclohexylbutyryl group; the term "heterocyclyl-(C-_|-C4)-alkanoyl" denotes, for example, the thenoyl, furoyl, nicotinoyl, thienylacetyl or the pyridinepropionyl group; the term "(C3-C8)-cycloalkoxycarbonyl" denotes, for example, the cyclobutyl- oxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or the cycloheptyloxycarbonyl group; the term "(C3-C8)-cycloalkyl-(Cι-C4)-alkoxycarbonyl" denotes, for example, the cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentyloxy- methoxycarbonyl, cyclohexyloxymethoxycarbonyl, 1-(cyclohexyl)-ethoxycarbonyl or the 2-(cyclohexyl)ethoxycarbonyl group; the term "aryl-(C_π-C4)-alkoxycarbonyl" denotes, for example, the benzyloxycarbonyl,

1-naphthylmethoxycarbonyl, 2-naphthylmethoxycarbonyl, 1-phenylethoxycarbonyl or the 2-phenylethoxycarbonyl group; the term "heterocyclyl-(C-|-C4)-alkoxycarbonyl" denotes, for example, the thienylmethoxycarbonyl, furylmethoxycarbonyl, tetrahydrofurylmethoxycarbonyl or the pyridylethoxycarbonyl group; the term "aryloxycarbonyl" denotes, for example, the phenoxycarbonyl, naphthoxycarbonyl or the biphenyloxycarbonyl group; the term "heterocyclyloxycarbonyl" denotes, for example, the tetrahydropyran-4- oxycarbonyl group; the term "(C<|-C2o)-alkanoyloxy" denotes, for example, the formyloxy, acetoxy, propionyloxy, butyryloxy, pivaloyloxy, valeroyloxy or the hexanoyloxy group; the term "(C2-C2θ)-haloalkanoyloxy" denotes a (C2-C2o)-alkanoyloxy group in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular fluorine or chlorine; the term "(C3-C8)-cycloalkanoyloxy" denotes, for example, the cyclopropanoyloxy, cyclobutenoyloxy, cyclopentanoyloxy, cyclohexanoyloxy or the cycloheptanoyloxy group; the term "(C3-C8)-cycloalkyl-(C-|-C4)-alkanoyloxy" denotes, for example, the cyclopropylcarbonyloxy, cyclopropylacetoxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cyclohexylacetoxy or the 4-cyclohexylbutyryloxy group; the term "aroyloxy" denotes, for example, the benzoyloxy or the naphthoyloxy group; the term "aryl-(C-_|-C4)-alkanoyioxy" denotes, for example, the benzoyloxy, naphthoyloxy, biphenylcarbonyloxy, phenylacetoxy or the phenylbutyryloxy group; the term "heterocyclyl-(Cι-C4)-alkanoyloxy" denotes, for example, the thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or the pyrimidinylcarbonyloxy group; the term "(C-|-C2θ)-alkylsulfonyloxy" denotes, for example, the methane-, ethane-, butane- or hexanesulfonyloxy group; the term "arylsulfonyloxy" denotes, for example, the phenylsulfonyloxy or the toluenesulfonyloxy group; a "bivalent hydrocarbon chain" denotes a radical which is derived from n-alkanes or n- alkenes by removal of in each case one hydrogen atom from each of the two terminal carbon atoms of the chain, such as methylene, ethanediyl, trimethylene, tetramethylene; the term "(C_π-Ci8)-alkanediyldioxy" denotes a bivalent radical derived from (C-_|-C_π8)- alkanes by replacement of two hydrogen atoms by two -O- radicals.

Furthermore, the definition that "in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x where x = 0, 1 or

2, NR²⁶ or SiR²⁷R²⁸, where R²⁶ is hydrogen, (C-|-C4)-alkyl, (C_π-C4)-alkoxy or

(C-j-C4)-alkanoyl and where R²⁷ and R²⁸ are each (C₁-C4)-alkyl, preferably methyl, and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals selected from the group consisting of 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, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents" denotes, for example: alkoxyalkyl radicals, for example the methoxymethyl, methoxyethyl or ethoxyethyl group; or alkoxyalkoxyalkyl radicals, for example the methoxy- or the ethoxyethoxyethyl group; or alkylthioalkyl radicals, for example the methyl- or the ethylthioethyl group; or alkylsulfinylalkyl radicals, for example the methyl- or ethylsulfinylethyl group; or alkylsulfonylalkyl radicals, for example the methyl- or ethylsulfonylethyl group; or alkyldialkylsilylalkyl radicals, preferably alkyldimethylsilylalkyl radicals, for example the trimethylsilylmethyl or the trimethylsilylethyl group; or trialkylsilyl radicals, preferably alkyldimethylsilyl radicals, for example the trimethylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl or the octyldimethylsilyl group; or cycloalkyldialkylsilyl radicals, preferably cycloalkyldimethylsilyl radicals, for example the cyclohexyldimethylsilyl group; or aryldialkylsilyl radicals, preferably aryldimethylsilyl radicals, for example the phenyldimethylsilyl group; or arylalkyldialkylsilyl radicals, preferably aryldimethylsilyl radicals, for example the benzyldimethylsilyl or the phenylethyldimethylsilyl group; or alkanoylalkyl radicals, for example the acetylmethyl or the pivaloylmethyl group; or cycloalkanoylalkyl radicals, for example the cyclopropylcarbonylmethyl or the cyclohexylcarbonylmethyl group; or haloalkanoylalkyl radicals, for example the trifluoro- or trichloroacetylmethyl group; or aroylalkyl radicals, for example the benzoyl- or naphthoylalkyl radicals, for example the phenylacetylmethyl group; or heterocyclylcarbonylalkyl radicals, for example the thienyl- or pyridylacetylmethyl group; or arylalkyl radicals, for example 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-methylnaphthyl group; or heterocyclylalkyl radicals, for example the thienylmethyl, pyridylmethyl, furfuryl-, tetrahydrofurfuryl-, tetrahydropyranylmethyl- or the 1 ,3-dioxalane-2-methyl group; or aryloxyalkyl radicals, for example the phenoxymethyl or naphthoxymethyl group; or cycloalkyl radicals, monocyclic such as, for example, the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical, bicyclic such as, for example, the norbornyl radical or the bicyclo[2.2.2]octane radical or condensed such as the decahydronaphthyl radical; alkylcycloalkyl radicals, for example the 4-methyl- or the 4-tert-butylcyclohexyl group or the 1-methylcyclopropyl, -cyclobutyl, -cyclopentyl- or -cyclohexyl group; cycloalkylalkyl radicals, for example the cyclohexylmethyl or -ethyl group; or else haloalkyl derivatives of the appropriate groups, for example haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkylcycloalkyl or halocycloalkyl radicals. This applies correspondingly to similar definitions.

The illustration given above applies correspondingly to homologs or to radicals derived therefrom.

In addition to the cis/trans isomerism mentioned, some of the compounds of the formula I have one or more asymmetric carbon atoms or stereoisomers at double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. Mixtures of diastereomers can be separated into the components by conventional methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by conventional methods, for example by salt formation with an optically active acid, separation of the diastereomeric salts and liberation of the pure enantiomers using a base. The invention furthermore relates to a process for preparing compounds of the formula I which comprises reacting a compound of the formula (V)

where G is CH or N and R¹ , R², R³ X, Y and Z are each as defined under formula I, with an electrophile of the formula (VI)

L-R (VI) where R is as defined under formula I and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, preferably halogen, if appropriate with the addition of salts such as, for example, AgBF4, AgNO3 or Nal, replacing, if appropriate, the anion of the compounds obtained in this manner by other anions, similarly to known methods [for example Liebigs Ann. Chem. 1978, 1937; Methoden der Org. Chemie/Houben-Weyl (D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 1008 ff., Thieme, Stuttgart 1990].

The substitution reaction described above is known in principle [for example Methoden der Org. Chemie/Houben-Weyl (D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 997 ff., Thieme, Stuttgart 1990, Liebigs Ann. Chem. 621 (1959) 106; Arch. Pharm. (Weinheim) 328 (1995) 531].

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

The abovementioned reaction is carried out in a temperature range from 20 to 150"C, if appropriate in an inert organic solvent such as acetonitrile, acetone, 2-butanone, N.N-dimethylforrnamide, 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. It is also possible to use mixtures of the solvents mentioned.

Most of the compounds of the formula (V) required as starting materials are known from the literature [for example DE-A-4 438 807, WO-A-96 11 913, WO-A-96 11 924, DE-4 343 250, WO-A-95 07 890, WO-A-94 21 613, DE-A-4 208 254], or they can be prepared similarly to known methods.

Compounds of the formula (VI) are commercially available, or they can be obtained by processes known in principle [for example: Verhe, De Kimpe, in "The Chemistry of Functional Groups, Supplement D" (Patai, Rappoport, Eds.), Part 1, p. 813 ff., Wiley, New York, 1983].

While being tolerated well by plants and having favorable toxicity toward warmblooded animals, the active substances are suitable for controlling animal pests, especially insects, arachnids, helminths and molluscs, and very particularly preferably for controlling insects and arachnids, which are encountered in agriculture, in animal breeding, in forestry, in the protection of stored products and materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or certain stages of development. The abovementioned pests include:

From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,

Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,

Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp..

From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and

Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus caφophagus and Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus,

Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and

Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp. From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus coφoris, Haematopinus spp. and Linognathus spp. From the order of the Mallophaga, for example, Trichodecte spp. and Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci and Frankliniella spp.

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

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arandinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Caφocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogorma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conorus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptus spp. From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp.,

Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp.,

Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hyporma spp., Tabanus spp., Tannia spp., Bibio hortulanus,

Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and

Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis and

Ceratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

From the class of the helminths, for example, Haemonchus, Trichostrongulus,

Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus,

Ancylostoma, Ascaris and heterakis and also Fasciola.

From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomeiania spp.

From the class of the Bivalva, for example, Dreissena spp.

The plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil nematodes such as, for example, those of the genera Meloidogyne (root-knot nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, heterodera trifolii) and of the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus),

Tylenchulus (such as Tylenchulus semipenetrans), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (such as Rotylenchus robustus), Helicotylenchus (such as Helicotylenchus multicinctus), Belonoaimus (such as Belonoaimus longicaudatus), Longidorus (such as Longidorus elongatus), Trichodorus (such as Trichodorus primitivus) and Xiphinema (such as Xiphinema index). The compounds according to the invention can also be used to control the nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (leaf-gall nematodes, such as Anguina tritici).

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

The compositions according to the invention comprise the active substances of the formulae I in general in a proportion of from 1 to 95% by weight. They can be formulated in various ways depending on the biological and/or chemicophysical parameters which prevail. Possible formulations which are suitable are therefore:

wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusts (DP), seed-dressing products, granules in the form of microgranules, spray granules, coated granules 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-Kϋchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, N.Y.; Marsden, "Solvents Guide", 2nd ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Coφ., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schόnfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Kϋchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, it is also possible to produce combinations with other pesticidally active substances, fertilizers and/or growth regulators, for example in the form of a readymix or a tank mix. Wettable powders are preparations, uniformly dispersible in water, which contain, beside the active substance and in addition to a diluent or inert material, wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6^,-disulfonate. Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers. As emulsifiers, the following can be used, for example: calcium salts of alkylaryl- sulfonates, such as Ca dodecylbenzenesulfonate, 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 polyoxyethylene sorbitol esters.

Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth. Granules can be prepared either by atomizing the active substance onto adsoφtive, granulated inert material or by applying active substance concentrates onto the surface of carrier materials such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or alternatively mineral oils. Suitable active substances can also be granulated in the fashion conventional for the preparation of fertiliser granules, if desired as a mixture with fertilisers.

In wettable powders, the concentration of active substance is, for example, from approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the concentration of active substance may be from approximately 5 to 80% by weight. Dust formulations comprise in most cases from 5 to 20% by weight of active substance, sprayable solutions from about 2 to 20% by weight. In the case of granules, the content of active substance depends partly on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc. are being used.

In addition, the abovementioned formulations of active substance comprise, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are customary in each case.

The concentrates, which are in the commercially customary form, are if appropriate diluted in the customary manner for their use, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and some microgranules. Dust and granule preparations, and also sprayable solutions, are normally not diluted any further with other inert substances before being used.

The application rate required varies with the external conditions, such as temperature and humidity among others. It can fluctuate within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha.

The active substances according to the invention may be present in their commercially customary formulations, and in the application forms prepared from these formulations, as mixtures with other active substances, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides.

The active substance content of the use forms prepared from the commercially customary formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.

Application is effected in a conventional fashion, matched to the use forms.

The active substances according to the invention are also suitable for controlling ecto- and endoparasites in the veterinary medicine sector or in the sector of animal husbandry. The active substances according to the invention are in this case applied in a known fashion, such as by oral application in the form of, for example, tablets, capsules, potions or granules, by dermal application in the form of, for example, dipping, spraying, pouring-on and spotting-on and powdering, and also by parenteral application in the form of, for example, injection.

The novel compounds, according to the invention, of the formula I can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.). In a preferred embodiment of the invention, the novel compounds, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since they are excreted in active form in the droppings, the development of insects in the animal droppings can be prevented very simply in this fashion. The dosages and formulations suitable in each case are particularly dependent on the type and stage of development of the productive animals and also on the degree of infestation, and can easily be determined and fixed by conventional methods. In the case of cattle, the novel compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight.

Some compounds of the formula I according to the invention are also distinguished by an fungicidal action. Fungal pathogens which have already penetrated the plant tissue can be successfully subjected to curative control. This is particularly important and advantageous in the case of those fungal diseases which can no longer be controlled effectively with the otherwise customary fungicides when infection has taken place already. The spectrum of action of the claimed compounds embraces various economically important phytopathogenic fungi, for example Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Piricularia oryzae, Pyrenophora teres, Leptosphaeria nodorum, Pellicularia sasakii and Puccinia recondita.

In addition, the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking, or as preservatives in drilling and cutting oils.

The active substances according to the invention in their commercially customary formulations can be employed either alone or in combination with other fungicides known from the literature. The abovementioned components for combinations are known active substances of which many are described in The Pesticide Manual, edited by C D S Tomlin, 11th edition (1997), bublished by the British Crop Protection Council. The active substance content of the use forms prepared from commercially customary formulations can vary within wide limits, and the concentration of active substance in the use forms can be from 0.0001 up to 95% by weight of active substance, preferably between 0.0001 and 1 % by weight. The formulations are applied in a customary manner adapted to suit the use forms.

The examples which follow illustrate the invention without limiting it thereto.

A. Formulation Examples

a) A dust is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as inert material and comminuting in a hammer mill.

b) A wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding in a pinned disk mill.

c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding in a ball mill to a fineness of below 5 microns.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active substance, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of ethoxylated nonylphenol (10 EO) as emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active substance and an inert granule carrier material such as attapulgite, granulated pumice and/or quartz sand. It is advantageous to use a suspension of the wettable powder of Example b) with a solids content of 30% which is sprayed onto the surface of attapulgite granules which are then dried and intimately mixed. The proportion by weight of the wettable powder in this case is about 5% and that of the inert carrier material is about 95% of the finished granules.

B. Preparation examples

Example 1

5-chloro-1-{4-[(diphenoxyphosphoryl)oxy]phenacyl)-6-ethyl- 4-(cis-phenylcyclohexylamino)pyrimidinium bromide

2.00 g of 5-chloro-6-ethyl-4-(cis-4-phenylcyclohexylamino)pyrimidine and 1.94 g of 4-(2-bromoacetyl)phenyl diphenyl phosphate were stirred in boiling acetone for 10 h. The solvent was removed under reduced pressure. Recrystallisation from methylene chloride/ethyl acetate gave the title product, m.p. 179-182°C.

Preparation of the starting material

4-(2-bromoacetyl)phenyl diphenyl phosphate

To 5.00 g of 4-acetylphenyl diphenyl phosphate dissolved in chloroform was added 0.69 ml of bromine, slowly, with stirring. The mixture was stirred at room temperature for 30 minutes and then quenched with water. The organic layer was washed twice with water and dried with sodium sulfate. Evaporation of the solvent gave the crude title product as a yellow oil, which was pure enough for further reactions. 4-acetylphenyl diphenyl phosphate

To 20 g of 4-hydroxyacetophenone dissolved in dimethylformamide were added 16.33 g of triethylamine followed by 39.46 g of O,O-diphenyl chlorophosphate. The reaction mixture was stirred at room temperature for 3J hours and then poured into water. The mixture was extracted repeatedly with dichloromethane and the combined organic layers were washed with water and dried with sodium sulfate. The solvent was removed and the residue purified by chromatography (silica gel: dichloromethane/methanol = 95:5), to give the title product as a yellow oil.

The compounds of the tables below were obtained similarly to [Examples 1 to 3.

In a similar manner the following compounds are obtained:

The formula implies that although the substituted methyl radical is shown attached to the 1 -position, it cannot be excluded that the attachment is to the nitrogen in position 3

There was also obtained:

5-chloro1-(cyanomethyl)-6-ethyl-4-(cis-4-phenylcyclohexylamino)pyrimidinium bromide, m.p. 180°C (compound 481) and 4-(cis-4-tert.-butylcyclohexylamino)-5-chloro-1-(cyanomethyl)-6- ethylpyrimidinium bromide, m.p. 207°C (compound 482)

C. Biological examples

Use as insecticide/acaricide

Example 1

A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Pieces of filter paper with about 30, 24-hour-old eggs of the tobacco budworm (Heliothis virescens) are dipped into an aqueous solution of the formulated preparation to be examined for about 5 seconds and subsequently placed into the Petri dish. A further 200 μl of the aqueous solution are spread over the culture medium. The Petri dish is sealed and then kept at about 25°C in a controlled climate chamber. After 6 days storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191,199 and 439 caused a mortality of 90-100%.

Example 2

Germinated field bean seeds (Vicia fabae) with radicles are transferred into brown bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae). Plants and aphids are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a controlled climate chamber (16 hours of light/day, 25"C, 40 - 60% relative atmospheric humidity). After 3 and 6 days storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191 and199 caused an aphid mortality of 90-100%.

Example 3

The leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, the rice plants treated in this manner are placed in a Petri dish and populated with about 20 larvae (L3 stage) of the rice leafhopper species Nilaparvata lugens. The Petri dish is sealed and then stored in a controlled climate chamber (16 hours of light/day, 25"C, 40 - 60% relative atmospheric humidity). After 6 days storage, the mortality among the leafhopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191,199 and 439 caused a mortality of 90-100%.

Example 4

A Petri dish, half of whose bottom is covered with filter paper and contains a germinated maize corn on a moist cotton pad, is prepared. About 50, 4 - 5-day-old eggs of the southern corn rootworm (Diabrotica undecimpunctata) are transferred onto the filter paper. Three drops of 200 μl of an aqueous solution of the formulated preparation to be examined are pipetted onto the eggs, and the rest is pipetted onto the maize corn. The Petri dish is sealed and then stored at about 25"C in a controlled climate chamber. After 6 days storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132 and 199 caused a mortality of 90-100%.

Example 5

Cut stems of bean plants (Phaseolus vulgaήs) carrying one leaf are transferred into brown bottles filled with tap water and subsequently populated with approximately 100 spider mites (Tetranychus urticae). Plant leaf and spider mites are then dipped for

5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a controlled climate chamber (16 hours of light/day, 25°C, 40 - 60% relative atmospheric humidity). After

6 days storage, the effect of the preparation on all stages of the spider mites is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191,199 and 439 caused a mortality of 90-100%.

Claims

PATENT CLAIMS:

1. A compound of formula

in which

(1) A is CH and D is N⁺R or

A is nitrogen and D is N⁺R or

A is N⁺R and D is nitrogen, where

R is CR⁴R⁵D^aR⁶,

(2) Qⁿ" is an inorganic or organic anion, n being 1 , 2, 3 or 4;

(3) R¹ is hydrogen, halogen, (C-|-C8)-alkyl, (C-|-C8)-haloalkyl, (C╬╖-CsJ-alkoxy or

(C₃-C₆)-cycloalkyl;

(4) R² and R³ are identical or different and are each hydrogen, (C-|-C8)-alkyl,

(C2-C8)-alkenyl,

(Ci-C╬▓r-alkoxy, halogen, hydroxy, cyano, nitro, thiocyanato, (C_╧Ç-C8)-alkoxycarbonyl, (C-_|-C8)-alkylthio,

(C_╬╖-C8)-alkylsulfinyl, (C╬╖-CsJ-alkylsulfonyl, amino; (C-_|-C8)-alkylamino,

(C-╬╣-C8)-dialkylamino or (C3-C6)-cycloalkyl, and in which in the alkyl, cycloalkyl, alkenyl, alkynyl groups or the groups derived from them, such as alkoxy, alkylfyl, alkanoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, a saturated carbon unit can be replaced by a hetero atom unit such as oxygen, S(O)_x, where x = 0, 1 or 2 or by dimethylsilyl and further in these groups or derived groups up to 3 hydrogen atoms can be replaced by halogen and in the case of fluorine also all hydrogen atoms can be replaced by fluorine; or R² and R³ together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered carbocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH2, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C-1-C4)- alkyl, (C-_|-C4)-haloalkyl, preferably trifluoromethyl, halogen, (C1-C4)- alkoxy or (C_╧Ç-C4)-haloalkoxy; or

R² and R³ together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered carbocyclic ring which may contain oxygen and/or sulfur instead of one or two CH2 groups and which may be substituted by 1, 2 or 3 (C-|-C4)-alkyl groups;

(5) X is O, S(O)_q where q = 0, 1 or 2, NR⁷, NR⁷CO, NR⁷CS or CR⁸R⁹, where R⁷ is hydrogen and R⁸ and R⁹ independently of one another are each hydrogen or (C_╧Ç_C4)-alkyl,

(6) Y - Z together are a (C₁-C2╬╕)-hydrocarbon radical which is straight-chain or branched and in which one or more, preferably up to three, CH2 may be replaced by hetero atom radicals such as O, NR^{l 0}, S, SO, SO2 or

SiR ¹R¹², where R ⁰ is hydrogen, (C-|-C4)-alkyl or (C┬½|-C4)-acyl, and

R^╬╖ 1 and R¹² are identical or different and are each independently of the other (C_╧Ç-C4)-alkyl, phenyl or substituted phenyl, and where this

(C_n-C2o)-hydrocarbon radical with the possible abovementioned variations may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of

(C-i-CyJ-alkyl,

(C2-C4)-alkenyl,

(C₂-C₄)-alkynyl,

(C3-C7)-cycloalkyl,

(C3-C7)-cycloalkenyl, halogen, halo-(C╬╣-C4)-alkyl, halo-(C-_j-C4)-alkoxy, hydroxy and

(C_╧Ç-C4)-acyl; or, if not included in the above definitions,

(7) Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms which may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of (Ci-C ╧è-alkyl,

(C2-C4)-alkenyl,

(C₃-C₇)-alkynyl,

(C3-C7)-cycloalkyl,

(C3-C7)-cycloalkenyl, halogen, halo-(C-_|-C4)-alkyl, halo-(C_╧Ç-C4)-alkoxy, hydroxyl and (C-_|-C4)-acyl; and

(8) Z is aryl or O-aryl, where aryl is preferably a naphthyl or phenyl group, heterocycyl or heterocyclyloxy, each of which may be substituted by one or more, preferably up to five, in particular up to three, identical or different radicals selected from the group consisting of halogen,

(C3-C8)-cycloalkyl,

(C3-C8)-cycloalkenyl, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, optionally substituted heterocyclyl, optionally substituted heterocyclylthio

NO₂,

-C(O)-R¹³, acetoxy, hydroxyl, cyano,

SiRl⁴Rl⁵Rl6,

R¹³ is (C╬╣-C7)-alkyl, halo-(C -C )-alkyl, (C₃-C₇)-cycloalkyl, halo-

(C-C7)-cycloalkyl, (C<|-C7)-alkoxy, phenyl or substituted phenyl;

R^l4, R¹⁵ and R¹⁶ are identical or different and are each independently of one another (C-|-C4)-alkyl, phenyl and/or substituted phenyl;

R^{╧Ç 7} and R^⁸ are identical or different and are each independently of the other hydrogen, (C-_|-C4)-alkyl and/or (C-_|-C4)-acyl;

R¹⁹ is (C_╧Ç-C-_|o)-alkyl, phenyl or substituted phenyl; wherein (C-|-C<|2r-alkyl, (C_╬╖-C-|2)-alkoxy,

and (C2-C_╬╖2)-alkenyl one or more, preferably up to 3, CH2 groups may be replaced by hetero atom radicals such as O, S, SO, SO₂, NR1┬░' or SiRll'Rl²'; R1┬░', RH' and R1²' have the meanings of R¹⁰, R , R¹²; the (C_╧Ç-C-|2)-alkyl radical with or without the abovementioned variations may also be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group below consisting of halogen, halo-(C-_|-C4)-alkoxy, hydroxyl, (C3-C8)- cycloalkyl, (C3-C8)-cycloalkenyl, (C-_|-C4)-acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (C_╧Ç-C7)-alkoxy and (C-1-C7)- alkylthio radicals, one or more, preferably up to three, CH2 groups may be replaced by O, and these radicals may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, phenyl, substituted phenyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, phenoxy and substituted phenoxy; or, if not included in the above definitions,

(C-i-C^-alkyl,

(C2-C4)-alkenyl,

(C₃-C₇)-alkynyl,

(C3-C7)-cycloalkyl,

(C3-C7)-cycloalkenyl, halogen, halo-(C_╧Ç-C4)-alkyl, halo-(C_╧Ç-C4)-alkoxy, hydroxyl and

(10) Z is (C3-C8)-cycloalkyl or (C5-C8)-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR²⁰;

R²⁰ is phenyl or substituted phenyl and the (C3~C8)-cycloalkyl or (C5-

C_╬▓J-cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (C-i-C-is_.-alkyl,

(C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy,

(C₂-C₁₈)-alkenyl,

(C₂-C₁₈)-alkynyl,

(Cl-C_╧Ç2)-alkoxy,

(C-_| -C 12)-alkanoyloxy, formyl, (C₂-C₁₂)-acyl,

( -C -j 2)-alkoxycarbonyl,

SiR² R²²R²³, _NR24_R25

C(O)NR² R²⁵, hydroxyl, halogen, aryl, heteroaryl,

O aryl,

O heteroaryl,

CH2╬╕aryl,

CH2╬╕heteroaryl,

(C-╬╣-Ci8)-alkanediyldioxy,

(C-_|-C-_|3)-alkoximino and

(C2-C-_|8)-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH2 groups in the (C-j.Cis)"- (C2-C18)-. (C1.C12)-, (C2-C12)- and (C-|-Ci3)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as O, NR¹⁰" or SiR^{l 1}"R¹² ", these hetero atom radicals preferably not being adjacent to one another, where R¹⁰", R¹¹" and R¹²" have the meanings of R¹⁰,

R¹¹ , R¹² and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, optionally substituted heterocyclyl, phenylthio and substituted phenylthio; where heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R²⁴ and R²⁵ are identical or different and are each independently of the other hydrogen, (C_╧Ç-C4)-alkyl, (C-|-C4)-acyl, (C3-

C6)-cycloalkyl, phenyl and substituted phenyl and where R²¹, R²²,

R²³ are identical or different and are each independently of the others (C-_|-C-_|8)-alkyl, (C<|-C"|8)-alkoxy, (C3-C8)-cycloalkyl and aryl, where in the (C-_|-C-_|8r-hydrocarbon radicals more than one, preferably up to three, non-adjacent CH2 groups may be replaced by oxygen and where

R²²) attached to silicon together to form a cycle, the silicon atom in this case being a ring atom of this cycle, and where additionally these (C-_|-C-_|8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the cycloalkyl or cycloalkenyl radicals defined under (10) may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1 ,4 position, preference is given to the cis configuration; or

(11) Y is a bond; and

(12) Z is (a) a group of the formula II

where each X¹ independently of the other is sulfur or oxygen; R^z is hydrogen, (C-_|-C4)-alkyl, trifluoromethyl or (C-_|-C4)-alkoxy; or

Ry is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x, where x = 0, 1 or 2, NR²⁶ or SiR²⁷R²⁸, where R²⁶ is hydrogen, (C-|-C4)-alkyl, (C_╧Ç-C4)-alkoxy or

(C-_|-C4)-alkanoyl and R²⁷ and R²⁸ are each (C_╧Ç-C4)-alkyl, preferably methyl; and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as mentioned above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyi, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkyl- alkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyanato or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where Ry and R^z together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the hetero atoms X¹ and where one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2 or NR²⁹, where R²⁹ is hydrogen, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by Ry and R^z may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, aralkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and R^z, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthaiene, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; in particular those groups of the formula II where

Ry is (C1-C20_. -alkyl, (C2-C2o)-alkenyl, (C2-C2o)-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x, where x = 0, 1 or

2, NR²⁶ or SiR²⁷R²⁸, where R²⁶ is hydrogen, (C╬╣-C₄)-alkyl,

(C_╧Ç-C4)-alkoxy or (C-|-C4)-alkanoyl and R²⁷ and R²⁸ are each

(C-|-C4)-alkyl, preferably methyl, and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, (C3-C8)- cycloalkoxy, (C3-C8)-cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (C╬╣-C-|2)-alkanoyl, (C3-C8)- cycloalkanoyl, (C2-C_╧Ç2)-^naloalkanoyl, aroyl, aryl-(C-|-C4)- alkanoyl, (C3-C8)-cycloalkyl-(C-_|-C4)-alkanoyl, heterocyclyl-(C┬½|-

C4)-alkanoyl, (C╬╣-C┬½|2)-alkoxycarbonyl, (C<|-C_╧Ç2r- haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C3-C8)- cycloalkyl-(C-_|-C4)-alkoxycarbonyl, aryl-(C-|-C4)-alkoxycarbonyl, heterocyclyl-(C-|-C4)-alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, (C-|-C_╧Ç2)-^a'kanoyloxy, (C2-C12)- haloalkanoylalkoxy, (C3-C8)-cycloalkanoyloxy, (C3-C8)- cycloalkyl-(C╬╣-C4)-alkanoyloxy, aroyloxy, aryl-(C-|-C4)-alkanoyl- oxy, heterocyclyl-(C-_|-C4)-alkanoyloxy, (C_╧Ç-C_╧Ç2)-alkyl- sulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyanato or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where Ry and R^z together form a three- to eight-membered ring system, which is spirocyclically linked to the ring system containing the hetero atoms ╧ç1 and where one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2 or NR²⁹, where R²⁹ is hydrogen, (C_╧Ç-C8)-alkyl, (C_╧Ç-C8.-alkoxy, (C-i-C╬▓)- alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents and where the ring system formed by Ry and R^z may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C╬╖-C_╬▓)- alkyl, (C-|-C8)-haloalkyl, (C_╧Ç-C8)-alkoxy, (C-|-C8)-alkylthio, (C3- C_╬▓r-cycloaikyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkylthio, aryl, aryloxy, arylthio, aryl-(C_╧Ç-C4)-alkyl, aryl-(C₁-C4)-alkoxy, aryl- (C-_|-C4)-alkylthio, heterocycyl, heterocyclyloxy, heterocyclylthio, (C-_|-C8)-trialkylsilyl, preferably (C╬╖-C_╬▓r-alkyldimethylsilyl, or (C-_|-C8)-alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and R^z, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1 ,2,3,4-tetrahydro- naphthalene, decahydronaphthalene or benzocycloheptane system and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where among the compounds where the carbon atom between the hetero atoms X¹ carries only the substituent Ry, the substituents X and Ry are preferably cis to each other; R^z is hydrogen, (C-|-C4)-alkyl, trifluoromethyl or (C-|-C4)-alkoxy; or (b) a group of formula

where ╬│1, Y² and Y³ independently of one another are each a group of the formula -O-, -CO-, -CNR³⁰-, -S(O)_r where r = 0, 1 or 2,

-N(O)_|R³⁰- where I = 0 or 1 or a group of the formula CR³¹R³²; or ╬│1 or Y³ stands in place of a direct bond, where

_R30 JS hydrogen, (C_╧Ç-C4)-alkyl, (C_╬╖-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (C_╧Ç- C4)-alkoxy, (C₁-C4)-haloalkoxy, (C-_|-C4)-alkylthio, (C_╧Ç-C4)-halo- alkylthio, (C_╧Ç-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C3-C5)- cycloalkyl, (C-|-C4)-alkylsulfonyl, (C-_|-C4)-haloalkylsulfonyl, (C-_|-C4)-alkoxy-(C-|-C4)-alkyl, (C-_|-C4)-alkoxycarbonyl;

R 1 and R³² independently of the other are each hydrogen, hydroxyl, halogen, cyano, (C-|-C4)-alkyl, (C-j-C^-haloalkyl, (C2-C4)- alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkenyl, (C3-C5)-cycloalkyl, (C-(-C4)-alkanoyl, (C1-C4)- haloalkanoyl, (C-|-C4)-alkoxy, (C-|-C4)-haloalkoxy, (C-1-C4)- alkylthio or (C_╧Ç-C4)-haloalkylthio; m is 0, 1, 2, 3 or 4, preferably 1 or 2; n is 0, 1, 2, 3 or 4, preferably 1 or 2; Z1 is a direct bond, NR³³, O, S(O)_s where s = 0, 1 or 2, OSO2,

SO₂O, NR³⁴SO₂, SO₂NR³⁵, SiR³⁶R³⁷ or U-C(W)-V, where R36 _ancj R37 _{are eac}h (C-_|-C4)-alkyl or phenyl, preferably methyl;

U is a direct bond, NR³⁸ or O;

W is oxygen or sulfur, preferably oxygen;

V is a direct bond, NR³⁹ or oxygen, where R33 R34 R35_t R38 _and R³⁹ are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;

R┬░. are substituents which are independent of one another and each is halogen, cyano, nitro, (C<|-C2o)-alkyl, (C2-C2o)-alkenyl,

(C2-C2o)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x where x = 0, 1 or 2, NR⁴⁰ or SiR ¹R⁴² and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D¹R⁴³, or

R┬░. is aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D²R⁴⁴, or two adjacent radicals zl-R⁰. may combine with the carbon atoms to which they are attached to form a fused cycle having 4 to 6 ring atoms which is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C-_|-C4)-alkyl and oxo, or

R33 R35 _or R39 independently of one another may combine with the

R┬░. located at Z to form a 4- to 8-membered ring system in which one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)t where t =

0, 1 or 2 or NR⁴⁵, where

R⁴⁰ is hydrogen, (C-|-C4)-alkyl, (C_╧Ç-C4)-alkoxy or (C-_|-C4.-alkanoyl;

R⁴¹ and R⁴² independently of the other are each (C_╧Ç-C4)-alkyl, preferably methyl; D¹ and D² are independent of each other and each is a direct bond, oxygen, S(O)_k, SO₂O, OSO₂, CO, OCO, COO, NR⁴⁶,

SO₂NR⁴⁶, NR ⁶SO₂, ONR⁴⁶, NR⁴⁶O, NR ⁶CO, CONR⁴⁶ or

_SJR47R48_I and k = 0, 1 or 2, where R46 independently of the others is hydrogen, (C-_|-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl;

R⁴⁷ and R⁴⁸ independently of the other are each (C-|-C4)-alkyl;

R43 and R⁴⁴ independently of the other are each hydrogen, cyano, nitro, halogen, (C_╧Ç-C8)-alkyl, (C-j-CsJ-haloalkyl, (C2-C8)- alkenyl, (C2-C8)-haloalkenyl, (C^-CsJ-alkynyl, (C2-C8)- haloalkynyl, (C-|-C8)-alkoxy-(C-|-C4)-alkyl, (Ci-CsJ-haloalkoxy- (C₁-C4)-alkyl,

(C-|-C₈)- haloalkylthio-(C-|-C4)-alkyl, (C3-C8)-cycloalkyl, (C4-C8)- cycloalkenyl, (C3-C8)-cycloalkyl-(C-|-C4)-alkyl, (C4-C8)- cycloalkenyl-(C-|-C4)-alkyl, aryl, heterocyclyl, aryl-(C-|-C4)-alkyl or heterocyclyl-(C-|-C4)-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁴⁹, or

R43 and R⁴⁴ located at the same carbon atom together are an oxo group, where

R⁴⁹ is (C₁-C₄)-alkyl, (C╬╖^.-haloalkyl, (C₁-C )-alkoxy, (C-1-C4)- haloalkoxy, cyano, nitro or halogen; R45 js hydrogen, (C_╧Ç-C8)-alkyl, (C-_|-C4)-haloalkyl, (C_╧Ç-C4)-alkoxy,

(C_╧Ç-C4)-alkylthio, (C3-C5)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)- alkynyl, (C<|-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C2-C4)- alkoxyalkyl, phenyl-(C-_j-C4)-alkyl or phenyl where the phenyl groups may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁵⁰, where

R⁵⁰ is (C₁-C4)-alkyl, (C₁-C₄)-haloalkyl, (C-|-C4)-alkoxy, (C-j-C₄)- alkylthio, halogen or cyano; or, if not included in the above definitions,

(c) is a group of the formula IV

where

Y⁴ is a direct bond or CH2;

Z² is oxygen, NR⁵¹, S(O)_m where m = 0, 1 or 2;

RU and wl-R* are substituents of the heteroaliphatic ring system, where

R^u is hydrogen, halogen, cyano, (C┬½|-C4)-alkyl, (C_╬╖-C4)-haloalkyl,

(C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkynyl, (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C1-C4)- alkoxy, (C┬½|-C4)-haloalkoxy, (C_╧Ç-C4)-alkanoyloxy, (C1-C4)- haloalkanoyloxy, (C_╧Ç-C4)-alkylthio or (C-|-C4)-haloalkylthio;

R* is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)_x where x = 0, 1 or 2, NR⁵³ or SiR⁵⁴R⁵⁵, and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D³R⁵⁶, or

R* may be aryl or heterocyclyl, where both of these radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D R⁵⁷ or

R⁵¹ is hydrogen, (C_╧Ç-C4)-alkyl, (C-|-C4)-haloalkyl, (C2-C4)-alkenyl,

(C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyI, (C-_j-

C4)-alkoxy, (C-|-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C1-C4)- alkoxy- (C₁-C4)-alkyl, (C₁-C4)-alkylthio-(C₁-C4)-alkyl, (C-1-C4)- alkoxycarbonyl, (C_╬╖-C4)-alkylsulfonyl, (C<|-C4)-haloalkylsulfonyl, phenylcarbonyl, phenyl-(C-|-C4)-alkyl or phenyl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁵⁹, or

R⁵ is CONR⁶⁰R⁶¹ where

R6┬░ and R⁶¹ independently of the other are each hydrogen, (C1-C4)- alkyl or phenyl, where the phenyl group may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁶², and R⁶² and R⁵⁹ independently of the other are each

(C<|-

R⁵⁴ and R⁵⁵ independently of the other are (C_╧Ç-C4)-alkyl, preferably methyl;

R⁵⁸ is hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁶³;

R⁶³ may be (C-|-C4)-alkyl, (C_╬╖-C4)-haloalkyl, (C_╬╖-C4)-alkoxy, (C1-C4)- haloalkoxy, cyano, nitro or halogen, and the ring system formed by R^u and R* may be unsubstituted or substituted by up to three, but preferably one, substituents D⁵R⁶⁴, or the ring system formed by R^u and R*, together with a further 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 may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D^R^⁵, where

D³, D4, D⁵ and D^ are independent of one another and are each a direct bond, oxygen, S(O)k, SO2O, OSO2, CO, OCO, COO,

SO₂NR⁶⁶, NR⁶⁶SO₂, NR⁶⁶O, ONR⁶⁶, NR⁶⁶, NR⁶⁶CO,

CONR⁶⁶ or SiR⁶⁷R⁶⁸, where k = 0, 1 or 2; and _R56 _R57 _R64 _ancj _R65 independently of one another are each hydrogen, cyano, nitro, halogen, (C_╧Ç-C8)-alkyl, (C-i-C╬▓)- haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (C_╧Ç-C8)-alkoxy-(C_╧Ç-C4)-alkyl, (C-|-Cs)- haloalkoxy-(C-|-C4)-alkyl, (C-|-C8)-alkylthio-(C-|-C4)-alkyl, (C╬╣-C8)-haloalkylthio-(C-_|-C4)-alkyl, (C3-C8)-cycloalkyl, (C4- C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C_╧Ç-C4)-alkyl, (C4-C8)- cycloalkenyl-(C-|-C4)-alkyl, aryl, heterocyclyl, aryl-(C-_|-C4)-alkyl or heterocyclyl-(C₁-C4)-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁶⁹, where R66 independently of the others is hydrogen, (C-j-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and R67 and R⁶⁸ independently of the other are each (C_╧Ç-C4)-alkyl, and

R⁶⁹ independently of the others may be (C_╧Ç-C4)-alkyl, (C1-C4)- haloalkyl,

(C-|-C4)-haloalkoxy, cyano, nitro, halogen, (C_╧Ç-C4)-alkanoyl or (C2-C4)-haloalkanoyl, or two of the radicals

R56 R57 R64 R65_ R69 _w ich are located at the same carbon atom together, and in each case independently of the others, are an oxo group; in particular those groups of the formula IV where

R* is hydrogen, (C-_j-Cer-alkyl, (C2-C8)-alkenyl, (Oj-CsJ-alkynyl, (C3-

NR⁵³ or SiR⁵⁴R⁵⁵, and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D³R⁵^, or

R* may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D⁴R⁵⁷, or

R^u and R* together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms Y⁴ and Z², and in which one CH2 group may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2 or NR⁵⁸, where R⁵³ is hydrogen, (C_╧Ç-C4)-alkyl, (C_╧Ç-C4)-alkoxy or (C-_|-C4)-alkanoyl and R⁵⁴ and R⁵⁵ independently of the other are (C_╧Ç-C4)-alkyl, preferably methyl;

R⁵⁸ is hydrogen, (C╬╣-Cg)-alkyl, (C╬╖-C╬▓J-alkanoyl, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^3_╬╣ and

R⁶³ may be (C-|-C4)-alkyl, (C-|-C4)-haloalkyl, (C<_|-C4)-alkoxy,

(C_╧Ç-C4)-haloalkoxy, cyano, nitro or halogen, and the ring system formed by R^u and R* may be unsubstituted or substituted by up to three, but preferably one, substituents Q5R64 _or t_{ne ╧Çn}g system formed by R^u and R*, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydro- naphthalene, decalin or benzocycloheptane system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D^R^ , where in the compounds where the carbon atom between Y⁴ and Z² where Y = CH2 only carries the substituent W^R*, the substituents X and W¹-R* are cis to each other;

D3, D⁴, D⁵ and D^ are independent of one another and are each a direct bond, oxygen, S(O)|<, SO2O, OSO2, CO, OCO, COO,

SO₂NR⁶⁶, NR⁶⁶SO₂, NR⁶⁶O, ONR⁶⁶, NR⁶⁶, NR⁶⁶CO or CONR⁶⁶, and k = 0, 1 or 2, R66 independently of the others is hydrogen, (C╬╣-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and

R56 R57 R64 _and R⁶⁵ independently of one another are each hydrogen, cyano, nitro, halogen, preferably fluorine, (C-j-Ce)- alkyl, (C3-C8)-cycloalkyl, aryl, heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁶⁹, where R69 independently of the others may be (C-_j-C4)-alkyl, (C1-C4)- haloalkyl,

(C-|-C4)-haloalkoxy, cyano, nitro, halogen, or two of the radicals R56 R57_f R64 _R65 R69 _w j_ch are located at the same carbon atom, together and in each case independently of the others, are an oxo group;

(14) R⁴ is a) hydrogen, halogen or C<|_4-alkyl or

(b) a negative charge, which can represent Q^n_

(15) R⁵ is hydrogen, halogen, CN, nitro, (C<|-C4)-alkoxycarbonyl, (C-1-C4)- alkylcarbamoyl, di-(C<|-C4)-alkylcarbamoyl, (C-|-C8)-alkoxy, (C╬╖-C_╬▓)- alkyl, (C2-C8)-alkenyl,

aryl or (C3-C8)-cycloalkyl;

(15) D^a is c) a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SO₂, C(=W^a), OC(=W^a) or d) U^a(C=W^a)V^a (U^a and V^a are a direct bond, NR⁷⁰, S or O, except V^a is not a bond when U^a is bond or O), SiR⁷²R⁷³, U^b(P=W^b)V V^c, U^b(SO₂)U^c (one of U^b and U^c is a direct bond, NR⁷⁰, S or O and the other is NR⁷⁰), U^a(CW^a)(CW^a)V^b, NR⁷⁰O, O NR⁷⁰, NR⁷⁰ NR⁷⁰,

N=N, -N=, - NR⁷⁰-N= or-O-N= , and

W^a is O, S or NR⁷¹;

W^b is O or S;

U^a, V^b and V^c, independently of each other are a direct bond, NR⁷⁰, S or O each R⁷⁰, which may be the same or different from any other R⁷⁰, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyloxy, and may also form a 4 to 8 membered with R⁶,

R¹¹² or R¹¹³, respectively with the Da, D¹² or. D¹³ to which they are attached, and in the case D^a is U^bP(=W^b)V^bV^c, the two R⁶ groups together with the V^bPV^c, to which they are attached can form a 4 to 8 membered ring

each R⁷1 , which may be the same or different from any other R⁷1 , is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;

R⁷² and R⁷³ are alkyl or optionally substituted aryl;

(16) R⁶ is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to three CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR⁷⁰ or Si R⁷²R⁷³ and can also be substituted by nitro, halogen, SF5 or D¹²R^{1 12}, and in the case D^a is U^bP(=W )V^bV^c, the two R⁶ groups together with the V^bPV^c, to which they are attached can form a 4 to 8 membered ring

D¹² is e) a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SiR⁷²R⁷³, U'(CW)V, or f) U '(PW¹')V¹'V²', U²'(SO₂)U³'_I Si(OR⁷²)R⁷³, Si(OR⁷²)(OR⁷³),NR⁷⁰O,

ONR⁷⁰, NR ⁰NR⁷⁰, N=N, =N-, =N-NR70- =N-O-, -N=, -NR⁷⁰-N= or - O-N= and

U'.U¹' V, V¹' and V²', independently of each other are a direct bond,

NR⁷⁰ S or O

W' is O, S or NR⁷¹;

W' is O or S;

U²' and U³', independently of each other are a direct bond, NR⁷⁰ or O;

(g) R^{1 12} is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR⁷⁰ or SiR⁷²R⁷³ and can also be substituted by nitro, halogen, SF5 or D^{l 3}R^{╧Ç ╧Ç 3} and in which two adjacent D^╬╖2R^{╧Ç l 2} together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C-|-C4-alkyl; or

(h) R ¹² is a negative charge for D ² = (CO)O, (SO₂)O, U¹'(PW )V¹O which replaces the ion Q^n_; or R^{1 12} is hydrogen for D¹² = O(CO)NH,

NR ⁰(CO)NH, O(CS)NH, NR⁷⁰(CS)NH, (CO)NH, (CS)NH, O(CO),

NR ⁰(CO), SO2NH;

D¹³ has the same meaning as D¹² and R^{1 13} has the same meaning as Rl1²; and in paragaraphs (13) - (16), aryl is as defined under (8) and, if it is not encompassed by the definition the carbon containing groups named under (13) to (16) can be substituted by one or more, preferably up to three (in the case of halogen up to the maximim number) of the same or different groups selected from halogen, cycloalkyl, phenoxy, substituted phenoxy, phenyl or substituted phenyl, with the proviso that at least one of the parameters defined in 13b, 15d or 16f or 16h applies.

2. A compound of the formula I as claimed in claim 1 , in which

A is CH and D is N⁺R or

A is nitrogen and D is N⁺R;

Q^n_ is an anion such as Hal-, NO3", BF4', BPh4" or PF╧ü";

R1 is hydrogen, methyl, fluorine or chlorine;

R² and R³ are each hydrogen, (C┬½|-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, amino, (C_╬╖-C4)-alkylamino, (C-|-C4)-dialkylamino, trimethylsilylethynyl, methoxycarbonyl, (C<_|-C4)-haloalkyl, (C2-C4)-haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or

R² and R³ join with the linking carbon atoms to form an unsaturated 5- or 6- membered ring with or without substitution which may, in the case of the 5- membered ring, contain a sulfur atom instead of a CH2 unit; or R² and R³ join with the linking carbon atoms to form a saturated 5- or 6-membered ring which may contain a sulfur or oxygen atom instead of a CH2 unit;

X is NH or oxygen.

3. A compound as claimed in claim 1 or 2, in which

Y is a bond or a methylene group which is substituted by one or two, preferably by one, (C₁-C4)-alkyl radical; and

Z is (C3-C8)-cycloalkyl or (C5-C8)-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR²⁰;

R²⁰ is phenyl or substituted phenyl and the (C3-C8)-cycloalkyl or (C5-C8)- cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (C-i-C-i╬▓J-alkyl,

(C₃-C₈)-cycloalkyl,

(C3-C8)-cycloalkoxy,

(C₂-C₁₈)-alkenyl,

(C₂-C₁₈)-alkynyl,

(C_╧Ç-C_╧Ç2)-alkoxy,

(Cl-C<i2)-alkanoyloxy, formyl, (C₂-C₁₂)-acyl,

(C_╧Ç-C-|2)-alkoxycarbonyl,

SiR²lR²²R²³ _NR24R25_I

CO-NR² R²⁵, hydroxyl, halogen, aryl, heteroaryl,

O aryl,

O heteroaryl,

CH2╬╕aryl, C^Oheteroaryl,

(C╬╣-Ci8)-alkanediyldioxy,

(C╬╣-Ci3)-alkyl-oximino and

(C2-C_╧Ç8)-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH2 groups in the (C-j-C-i╬▓)-.

(C2-C-18)-. (C1-C-12)-. (C2-C-12)- and (Ci-C^-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as O, NR^╧Ç " or

SiR¹¹ "R¹²", these hetero atom radicals preferably not being adjacent to one another, where R ⁰", R¹ " and R¹²" have the meanings of R¹⁰, R¹¹, R ² and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio;

where heteroaryl is unsubstituted or may be substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R²⁴ and R²⁵ are identical or different and are each independently of the other hydrogen, (C-|-C4)-alkyl, (C-|-C4)-acyl, (C3-Cg)-cycloalkyl, phenyl and substituted phenyl and where R^2╧Ç, R²², R²³ are identical or different and are each independently of the others (C-j-C-i╬▓_.-alkyl, (C<|-Ci8)-alkoxy, (C3-

C╬▓J-cycloalkyl and aryl, where in the (C╬╖-C-isJ-hydrocarbon radicals more than one, preferably up to three, CH2 groups may be replaced by oxygen and where 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it also being possible for two of the carbon radicals (for example R^2"1 and R²²) attached to silicon together to form a cycle, the silicon atom possibly being part of this cycle, and where additionally these (Ci-C^┬½|8)-hyd^rocarboⁿ radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the (C3-C8)-cycloalkyl or (Cs-C╬▓J-cycloalkenyl radicals defined above may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1 ,4 position, preference is given to the cis configuration; or

is a bond; and

(a) is a group of the formula II

where ╧ç1 is oxygen;

Ry is (C₁-C2o)-alkyl, (C2-C2╬╕)-alkenyl, (C2-C2╬╕)-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by hetero atom units such as oxygen or SiR²⁷R²⁸, where R²⁷ and R²⁸ are each (C-|-C4)-alkyl, preferably methyl, and where additionally 3 to 6 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle, and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably by up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, preferably fluorine, aryl, aryloxy, arylthio, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkylthio, heterocyclyl, heterocyclyloxy or (C_╧Ç-C2)-alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or Ry and R^z together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms X¹, and where one CH2 group may be replaced by hetero atom units such as oxygen, S(O)_n where n = 0, 1 or 2 or NR²⁹, where R²⁹ is hydrogen, (C-|-C8)-alkyl, (C_╧Ç-C8)-alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by Ry and R^z may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C-_j-CsJ-alkyl, (C3- C8)-cycloalkyl, aryl or aryl-(C-|-C4)-alkyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry 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, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where in the compounds where the carbon atom between the hetero atoms X¹ only carries the substituent Ry, the substituents X and Ry on the heteroaliphatic six-membered ring are preferably cis to each other; and

R^z is hydrogen or (b) is a group of the formula (III)

where Y¹ , Y² and Y³ are each a group of the formula -O-, -S(O)_r, where r = 0, 1 or 2 or is a group of the formula CR³¹ R³² , or Y¹ or Y³ stand in place of a direct bond, where

R^3*! and R³² independently of the other are each hydrogen or methyl; m¹ is 1 or 2; n¹ is 1 or 2;

Z is a direct bond, NR³³, O, S(O)_s where s = 0, 1 or 2, OSO2, SO2O,

NR³⁴SO₂, SO₂NR³⁵, SiR³⁶R³⁷ or U-C(W)-V, where

U is a direct bond, NR³⁸ or O;

W is oxygen;

V is a direct bond, NR³⁹ or oxygen; and

R³⁶ and R³⁷ are each (C-|-C4)-alkyl or phenyl, preferably methyl;

R33 R34 R35 R38 _and R³⁹ are identical or different and are each hydrogen, (C-|-C4)-alkyl, (C-|-C4)-alkoxy, (C_╧Ç-C4)-alkanoyl or (C3-C5)-cycloalkyl;

R┬░. independently of the others is (C -CsJ-alkyl where one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen and which, with or without the variations mentioned, may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D^ R⁴³, or

R┬░. may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D²R⁴⁴;

D¹ and D² are independent of one another and are each a direct bond, -O-,

-S(O)_k-, -SO₂O-, -OSO2-, -CO-, -OCO-, -COO-, -NR⁴⁶-, -SO₂NR⁴6-,

-NR ⁶SO₂-, -ONR⁴⁶-, -NR ⁶O-, -NR⁴⁶CO-, -CONR⁴⁶-, and k = 0, 1 or 2, and where R46 independently of the others is hydrogen, (C_╧Ç-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl; R⁴³ and R⁴⁴ independently of the other are each hydrogen, halogen, preferably fluorine, (C_╧Ç-C8)-alkyl, (C3-C8)-cycloaIkyl, aryl or heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R⁴⁹, where R49 independently of the others may be (C_╧Ç-C4)-alkyl, (C-|-C4)-haloalkyl,

(C-|-C4)-alkoxy, (C-|-C4)-haloalkoxy, cyano, nitro, halogen; or,

(c) is a group of the formula IV

where

Y⁴ is a direct bond or CH2;

Z² is oxygen;

R^u is hydrogen, (C_╧Ç-C4)-alkyl, trifluoromethyl or (C-|-C4)-alkoxy;

W¹ is a direct bond, oxygen, -CO-, -COO-, CONR⁵², sulfur, -C=N-,

-C=N-O- where R⁵² is hydrogen, (C_╧Ç-C4)-alkyl, (C_╧Ç-C4)-alkanoyl and (C3-C5)-cycloalkyl, and

R^l is as defined above under (12 c).

4. A compound as claimed in any of the preceding claims, in which

R^ is hydrogen;

R² and R³ are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3)-alkenyl, amino, (C<|-C4)-alkylamino, (C_╧Ç-C4)-dialkylamino, (C2-C3)-chloro- or - fluoroalkenyl, (C2-C3)-alkynyl, trimethylsilylethynyl, (C_╧Ç-C3)-chloro- or - fluoroalkyl, methoxymethyl, halogen or cyano; or R² and R³ together with the ring system to which they are attached form the quinazoline or quinoline system, which may be fluorine-substituted in the carbocyclic moiety; or

R² and R3 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 CH2 group.

5. A compound as claimed in any of the preceding claims, in which

X is NH;

Y is a bond; and

Z (a) is cyclopentyl or cyclohexyl, where both radicals may be substituted as above under (10) and where, in the case of cyclohexyl, 1 ,4-substitution is preferred, the substituents being cis to one another; or

( ) is a group of the formula

or (c) is a group of the formula

where

Y¹ is CH₂;

Y² is CH₂;

Y³ is CH2, O or a direct bond; 1 1 C

ml is 1 or

(d) is a group of the formula IV

where

Y⁴ is a direct bond or CH2;

Z² is oxygen;

R^u is hydrogen or methyl.

6. A compound as claimed in any of the preceding claims, in which

A is CH and D is N⁺R or

A is nitrogen and D is N⁺R;

Q^" is an inorganic or organic anion, such as Hal", NO3", BF4", BPr.4-, PF╬▓";

R⁵ is hydrogen;

R⁶ is hydrogen, halogen, (C-|-Cs)-alkyl, (C-_j-CsJ-haloalkyl, (C2-C8)-alkenyl, (C2- C₈)-alkynyl;

7. A compound as claimed in any of the preceding claims, in which R1 is hydrogen;

R² is ethyl or methoxymethyl;

R³ is chlorine, bromine or methoxy, preferably those for which R² is ethyl and R³ is chlorine;

R⁵ is hydrogen;

R⁶ is hydrogen or methyl.

8. An insecticidal or acaricidal composition comprising an effective amount of at least one compound as claimed in any one of the preceding claims together with the additives or auxiliaries which are customary for these applications.

9. A method of controlling insects or acarids, which comprises applying an effective amount of a compound as claimed in any in any one of the preceding claims to insects acarids or their loci.

10. Seed, treated or coated with an effective amount of a compound as claimed in in claim 1.

11. Seed, treated or coated with in effective amount of a composition as claimed in claim 8.