AU7300598A

AU7300598A - Quaternary nitrogen heterocycles, method for their production and thei r use as pesticides

Info

Publication number: AU7300598A
Application number: AU73005/98A
Authority: AU
Inventors: Werner Bonin; Ralf Braun; Harald Jakobi; Manfred Kern; Gerhard Krautstrunk; Martin Markl; Ulrich Sanft; Wolfgang Schaper; Herbert Stark; Marie-Theresia Thonessen
Original assignee: Hoechst Schering Agrevo GmbH
Current assignee: Bayer CropScience AG
Priority date: 1996-11-15
Filing date: 1997-10-24
Publication date: 1998-06-10
Also published as: CN1237964A; TR199901076T2; ZA9710242B; KR20000053315A; EP0938478A1; JP2001504472A; DE19647413A1; WO1998022444A1; BR9712954A

Description

WO 98/22444 1 PCT/EP97/05886 QUARTERNARY NITROGEN HETEROCYCLES, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS PESTICIDES 5 Substituted nitrogen heterocycles, processes for their preparation and their use as pesticides The invention relates to novel substituted pyridines and pyrimidines and condensed systems derived therefrom, processes for their preparation and 10 their use as pesticides and fungicides. 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). 15 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 nitrogen heterocycles of the formula I have been 20 found Y--Z x R3() A Qn 25 n R2: D Ri in which the radicals and groups are as defined below, which, while showing good tolerance by plants and favorable toxicity in 30 respect of warm-blooded animals, are highly suitable for controlling animal pests, such as insects, arachnids, nematodes, helminths and molluscs, for controlling endoparasites and ectoparasites in the veterinary field and for controlling harmful fungi.

2 The invention therefore relates to compounds of the formula I in which (1) A is CH and D is N*R 5 or A is nitrogen and D is N*R or 10 A is N*R and D is nitrogen, where R is E R6 15 R 4

R

5 (2) Qn- is any inorganic or organic anion, n being 1, 2, 3 or 4; (3) R 1 is hydrogen, halogen, (Cl-C 4 )-alkyl, (C-C 4 )-haloalkyl or 20

(C

3

-C

5 )-cycloalkyl; (4) R 2 and R 3 are identical or different and are each hydrogen, (CC4) alkyl, (Cl C 4 )-haloalkyl, (C 2

-C

4 )-alkenyl, (C 2

-C

4 )-haloalkenyl,

(C

2

-C

4 )-alkynyl, (C 2

-C

4 )-haloalkynyl, (Cl C 8 )-trialkylsilyl 25 alkynyl, preferably dimethyl-(0 1

-C

8 )-alkylsilylalkynyl, (Cl-C4) alkoxy, (Cl-C4)-haloalkoxy, (C1-C4)-alkoxy-(C-C4)-alkyl, (Cl-C4)-haloalkoxy-(Cl-C4)-alkyl, (Cl-C4)-alkoxy-(Cl C4) haloalkyl, (Cl-C4)-haloalkoxy-(Cl-C4)-haloalkyl, amino, monosubstituted amino, disubstituted amino, halogen, 30 hydroxyl, (Cl-C4)-hydroxyakyl, (Cl-C4)-alkanoyl, (Cl C4) alkanoyl-(C-C4)-alkyl, (Cl-C4)-haloalkanoyl,

(C

3

-C

5 )-cyclo alkyl, (C 3

-C

5 )-halocycloalkyl, cyano, (Cl-C4)-cyanoalkyl, nitro, (Ci-C4)-nitroalkyl, thiocyano, (Cl-C4)-thiocyanoalkyl, (Cl C4) alkoxycarbonyl, (Cl-C4)-alkoxycarbonyl-(Cl-C4)-alkyl, 3 (Cl-C 4 )-haloalkoxycarbonyl, (Cl-C 4 )-alkylthio, (Ci-C 4 )-alkyl thio-(Cl-C4)-alkyl, (Cl-C4)-haloalkylthio, (Cl-C4)-alkylsulfinyl,

(C-C

4 )-haloalkylsulfinyl, (Ci-C 4 )-alkylsulfonyl or (Cl-C4) haloalkylsulfonyl; or 5 R 2 and R 3 join with the linking carbon atoms to form an unsaturated 5- or 6-membered isocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of

CH

2 , 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 10 may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (ClC 4 )-alkyl, (Cl-C 4 )-haloalkyl, preferably trifluoromethyl, halogen, (CC - 4 )-alkoxy or (Cl-C 4 )-haloalkoxy; or

R

2 and R 3 join with the linking carbon atoms to form a saturated 5-, 15 6- or 7-membered isocyclic ring which may contain oxygen and/or sulfur instead of one or two CH 2 groups and which may be substituted by 1, 2 or 3 (Cr-C 4 )-alkyl groups; (5) X is 0, S(O)q where q = 0, 1 or 2, NR 7 or CR 8

R

9 , where R 7 is 20 hydrogen and R 8 and R 9 independently of one another are each hydrogen or (ClC 4 )-alkyl, (6) Y - Z together are a (Cl-C 20 )-hydrocarbon radical which is straight chain or branched and in which one or more, preferably up to three, 25 CH 2 may be replaced by hetero atom radicals such as 0, NR 1 O, S, SO, SO 2 or SiR 1 R 12 , where R1 0 is hydrogen, (C-C 4 )-alkyl or

(C-C

4 )-acyl, and R" and R 12 are identical or different and are each independently of the other (C.-C 4 )-alkyl, phenyl or substituted phenyl, and where this (Cl-C 20 )-hydrocarbon radical with the 30 possible abovementioned variations may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of 4 (Ci-C 7 )-alkyl,

(C

2

-C

4 )-alkenyl,

(C

2

-C

4 )-alkynyl,

(C

3

-C

7 )-cycloalkyl, 5 (C 3

-C

7 )-cycloalkenyl, halogen, halo-(Cl-C 4 )-alkyl, halo-(C-C 4 )-alkoxy, hydroxyl and 10 (Cl-C 4 )-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 15 three, identical or different radicals selected from the group consisting of (C-C)-alkyl,

(C

2 -0 4 )-alkenyl, 20 (C 3

-C

7 )-alkynyl,

(C

3

-C

7 )-cycloalkyl,

(C

3

-C

7 )-cycloalkenyl, halogen, halo-(Cl-C 4 )-alkyl, 25 halo-(Cl C 4 )-alkoxy, hydroxyl and (Cl-C 4 )-acyl; and (8) Z is aryl or O-aryl, where aryl is preferably a naphthyl or phenyl 30 group 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 5 halogen,

(C

3

-C

8 )-cycloalkyl,

(C

3

-C

8 )-cycloalkenyl, phenoxy, 5 substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, 10

NO

2 , 0 -C-R13 acetoxy, 15 hydroxyl, cyano, SiR 14 R1 5

R

16 , 0-SiR4R R

NR

17

R

18 20 S(O)R19,

SO

2 R1 9, (C1-C1 2 )-alkyl, (C2-C1 2 )-alkenyl, (C1-C1 2 )-alkoxy and 25 (Cl-C1 2 )-alkylthio; and

R

13 is (C-Cy)-alkyl, halo-(Cl-C 7 )-alkyl, (C 3

-C

7 )-cycloalkyl, halo-(C 3

-C

7 )-cycloalkyl, (C,-C 7 )-alkoxy, phenyl or substituted phenyl; 30 R 14 , R 15 and R1 6 are identical or different and are each independently of one another (Cl-C 4 )-alkyl, phenyl and/or substituted phenyl; R1 7 and R 18 are identical or different and are each independently of the other hydrogen, (Cl-C 4 )-alkyl and/or 6

(C

1

C

4 )-acyl;

R'

9 is (C 1

C

10 )-alkyl, phenyl or substituted phenyl; where in (CI-C1 2 )-alkyl, (C-C1 2 )-alkoxy, (C-C1 2 )-alkylthio 5 and (C 2

-C

12 )-alkenyl one or more, preferably up to 3, CH 2 groups may be replaced by hetero atom radicals such as 0, S, SO, SO2, NR 1 O' or SiR 1

"R

12 '; R10', R"' and R 12 ' have the meanings of R1 0 , R 11 , R 12 ; the (Cl-C 12 )-alkyl radical with or without the abovementioned 10 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 1

C

4 )-alkoxy, hydroxyl, (C 3 -C)-cycloalkyl,

(C

3

-C

8 )-cycloalkenyl, (Cl C4) 15 acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (Cl-C7) alkoxy and (CC 7 )-alkylthio radicals, one or more, preferably up to three, CH 2 groups may be replaced by 0, and these radicals may be substituted by one or more, preferably up to 20 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, (C 3

-C

8 )-cycloalkenyl, phenoxy and substituted phenoxy; or, if not included in the above definitions, 25 (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 30 (1-Cy)-alkyl,

(C

2

-C

4 )-alkenyl,

(C

3

-C

7 )-alkynyl,

(C

3 -Cy)-cycloalkyl, 7

(C

3

-C

7 )-cycloalkenyl, halogen, halo-(C-C 4 )-alkyl, halo-(Cl-C 4 )-alkoxy, 5 hydroxyl and

(C

1

C

4 )-acyl; and (10) Z is (C 3

-C

8 )-cycloalkyl or (C 5

-C

8 )-cycloalkenyl, where a CH 2 group of the carbocycle may be replaced by NR 20 ; 10 R 20 is phenyl or substituted phenyl and the (C 3

-C

8 )-cycloalkyl or (C 5

-C

8 )-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 15

(C-C

18 )-alkyl,

(C

3 -C)-cycloalkyl,

(C

3 -C)-cycloalkoxy, (C2-C18 )-alkenyl, 20

(C

2 -C1 8 )-alkynyl, (CrC12)-alkoxy, (C1 -C1 2 )-alkanoyloxy, formyl, (C2-C1 2 )-acyl, 25 (ClC1 2 )-alkyl-oxycarbonyl, SiR 2 1

R

22

R

23 , N R 2 4

R

25 , 0 30 C-NR 24

R

25 , hydroxyl, halogen, aryl, heteroaryl, 8 o aryl, o heteroaryl,

CH

2 0 aryl,

CH

2 0 heteroaryl, 5

(C

1 C1 8 )-alkanediyldioxy,

(C

1

-

3 )-alkyl-oximino and

(C

2

-C

18 )-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH 2 groups in the (C1C18)-, (C2-C18)-, (C1C12)-, (C2-012)- and 10 (C 1 -0 13 )-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as 0, NR 10 " or SiR 11

"R

12 ", these hetero atom radicals preferably not being adjacent to one another, where R10", R1" and R 12 " have the meanings of

R

10 , R 11 , R 12 and where additionally 3 to 6 carbon atoms of 15 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 20 hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, 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) 25 identical or different substituents; where aryl is as defined under (8); where R 24 and R 25 are identical or different and are each independently of the other hydrogen,

(C

1

C

4 )-alkyl, (C1C4) 30 acyl, (C 3

-C

6 )-cycloalkyl, phenyl and substituted phenyl and where R 21 , R 22 , R 23 are identical or different and are each independently of the others (C-C1 8 )-alkyl, (C1C1 8 )-alkoxy,

(C

3

-C

8 )-cycloalkyl and aryl, where in the (C-C1 8 )-hydro carbon radicals more than one, preferably up to three, non- 9 adjacent CH 2 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 21 and R 22 ) attached to silicon together to form 5 a cycle, the silicon atom in this case being a ring atom of this cycle, and where additionally these (C-Cl 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 10 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 15 1,4 position, preference is given to the cis configuration; or (11) Y is a bond; and (12) Z (a) is a group of the formula 11 20

X

1 Rz where X 1 independently of the other is sulfur or 25 oxygen; Rz is hydrogen,

(C

1

C

4 )-alkyl, trifluoromethyl or (C1C4) alkoxy; or RY is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be 30 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 10 replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x, where x = 0, 1 or 2, NR 26 or SiR 27

R

28 , where R 26 is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkoxy or (Cl-C 4 )-alkanoyl and R 27 and R 28 5 are each (C-C 4 )-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 10 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, hetero 15 cyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxy carbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, 20 heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkyl sulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano 25 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 RV 30 and Rz 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 CH 2 groups, preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S(O)n 11 where n = 0, 1 or 2 or NR 29 , where R 29 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 5 of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by RY and Rz may be unsubstituted or substi tuted by up to three, but preferably one, substituents and where these substituents are identical or different 10 and are each alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or alkoxycarbonyl, where the cycloaliphatic, aromatic or 15 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 Rz, together with a 20 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 25 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 il where 30 RY is (C-C 20 )-alkyl, (C 2 -C2 0 )-alkenyl, (C 2 -0 20 )-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 12 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 5 oxygen, S(O)x, where x = 0, 1 or 2, NR 26 or SiR 27

R

28 , where R 26 is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkoxy or (Cl-C 4 )-alkanoyl and R 27 and R 28 are each (ClC4) alkyl, preferably methyl, and where additionally 3 to 12 atoms of these hydro 10 carbon 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), 15 identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, (C3-C8) cycloalkoxy, (C 3

-C

8 )-cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (C-C1 2 )-alkanoyl,

(C

3

-C

8 )-cycloalkanoyl, (C 2

-C

12 )-haloalkanoyl, aroyl, 20 aryl-(C 1

C

4 )-alkanoyl,

(C

3 -0 8 )-cycloalkyl-(C 1

C

4

)

alkanoyl, heterocyclyl-(Cl

C

4 )-alkanoyl, (C1 C12) alkoxycarbonyl, (Cl-C1 2 )-haloalkoxycarbonyl, (C3-C8) cycloalkoxycarbonyl,

(C

3

-C

8 )-cycloalkyl-(C 1 -C4) alkoxycarbonyl, aryl-(C-C 4 )-alkoxycarbonyl, 25 heterocyclyl-(C-C 4 )-alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl,

(C-C

12 )-alkanoyloxy,

(C

2

-C

12 )-haloalkanoylalkoxy,

(C

3

-C

8 )-cycloalkanoyl oxy, (C 3 -C)-cycloalkyl-(C-C 4 )-alkanoyloxy, aroyloxy, aryl-(C-C 4 )-alkanoyloxy, heterocyclyl-(Cl C4) 30 alkanoyloxy, (Ci-C1 2 )-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 13 of fluorine up to the maximum number) identical or different substituents, or where RV and Rz together form a three- to eight membered ring system, which is spirocyclically linked 5 to the ring system containing the hetero atoms X 1 and where one or two CH 2 groups, preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR 29 , where R 29 is hydrogen,

(C

1 C-)-alkyl, (C-C)-alkoxy, (C1C8) 10 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 15 formed by RV and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (0 1

-C

8 )-alkyl, (C1C8) haloalkyl, (Cl-C)-alkoxy, (C-Cs)-alkylthio, (C3-C8) 20 cycloalkyl, (C 3

-C

8 )-cycloalkoxy, (C 3

-C

8 )-cycloalkylthio, aryl, aryloxy, arylthio, aryl-(Cl-C4)-alkyl, aryl-(C-C4) alkoxy, aryl-(Cl-C4)-alkylthio, heterocycyl, heterocyclyloxy, heterocyclylthio,

(C

1

C

8 )-trialkylsilyl, preferably

(C-C

8 )-alkyldimethylsilyl, or (Cl C8) 25 alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned and substituted or may be substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, 30 or where the ring system formed by RV and Rz, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decahydro naphthalene or benzocycloheptane system and where 14 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, 5 where among the compounds where the carbon atom between the hetero atoms X 1 carries only the substituent RY, the substituents X and RY are preferably cis to each other; Rz is hydrogen, (Cl-C 4 )-alkyl, trifluoromethyl or (C1C4) 10 alkoxy; or (b) is a group of the formula IlIl 15 r (Z - Ry

)

3 n 15

Y

1 where Yl, Y 2 and Y 3 independently of one another are each a group 20 of the formula -0-, -CO-, -CNR 30 -, -S(O)r- where r = 0, 1 or 2, -N(O)IR 30 - where I = 0 or 1 or a group of the formula CR 31

R

32 ; or Y' or Y 3 stands in place of a direct bond, where 25 R 30 is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (C2-C4) alkenyl, (C 2

-C

4 )-haloalkenyl,

(C

2

-C

4 )-alkynyl, (C2-C4) haloalkynyl, (C1-C 4 )-alkoxy, (C1-C 4 )-haloalkoxy, (Cl-C 4 )-alkylthio, (Cl-C 4 )-haloalkylthio, (Cl C4) alkanoyl, (C 2

-C

4 )-haloalkanoyl, (C 3

-C

5 )-cycloalkyl, 30 (Cl-C 4 )-alkylsulfonyl, (Cl-C 4 )-haloalkylsulfonyl, (C1 C 4 )-alkoxy-(Cj C 4 )-alkyl, (Cl-C 4 )-alkoxycarbonyl;

R

31 and R 32 independently of the other are each hydrogen, hydroxyl, halogen, cyano, (Cl-C 4 )-alkyl, (Ci-C 4 )-halo alkyl, (C 2

-C

4 )-alkenyl,

(C

2

-C

4 )-haloalkenyl, (C2-C4)- 15 alkynyl, (C 2

-C

4 )-haloalkenyl, (C 3 -C)-cycloalkyl, (Cl-C 4 )-alkanoyl, (Cl-C 4 )-haloalkanoyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy,

(C

1

-C

4 )-alkylthio or (Cl C4) haloalkylthio; 5 mi is 0, 1, 2, 3 or 4, preferably 1 or 2; ni is 0, 1, 2, 3 or 4, preferably 1 or 2;

Z

1 is a direct bond, NR 33 , 0, S(O)s where s = 0, 1 or 2, OS02, SO20, NR 34

SO

2 , S0 2

NR

35 , SiR 36

R

37 or U-C-V, 10 11 W where

R

36 and R 37 are each (Cl-C 4 )-alkyl or phenyl, preferably methyl; 15 U is a direct bond, NR 38 or 0; W is oxygen or sulfur, preferably oxygen; V is a direct bond, NR 39 or oxygen, where

R

33 , R 34 , R 35 , R 38 and R 39 are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl; 20 Rq are substituents which are independent of one another and each is halogen, cyano, nitro, (C-C2 0 )-alkyl,

(C

2

-C

20 )-alkenyl, (C 2

-C

20 )-alkynyl, (C 3

-C

8 )-cycloalkyl,

(C

4

-C

8 )-cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated 25 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, NR 40 or SiR 41

R

42 and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three 30 (in the case of fluorine up to the maximum number), identical or different radicals D 1

R

43 , or Rq 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 16 or different radicals D 2

R

44 , or two adjacent radicals Z1-Rq 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 5 selected from the group consisting of 0, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Cl-C 4 )-alkyl and oxo, or

R

33 , R 35 or R 39 independently of one another may combine 10 with the Rq located at Z to form a 4- to 8-membered ring system in which one or two CH 2 groups, preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S(O)t where t = 0, 1 or 2 or NR45, 15 where

R

40 is hydrogen,

(C

1

C

4 )-alkyl, (Cl-C 4 )-alkoxy or (Cl-C4) alkanoyl;

R

4 1 and R 42 independently of the other are each (C0-04) alkyl, preferably methyl; 20 D' and D 2 are independent of each other and each is a direct bond, oxygen, S(O)k, SO20, OS02, CO, OCO, Coo,

NR

46 , SO 2

NR

46 , NR 46 S0 2 , ONR 46 , NR 46 0, NR 46 CO,

CONR

46 or SiR 47

R

48 , and k = 0, 1 or 2, where

R

46 independently of the others is hydrogen, (C 1

C

4 )-alkyl, 25

(C-C

4 )-alkanoyl or (C 3

-C

5 )-cycloalkyl;

R

47 and R 48 independently of the other are each (C1C4) alkyl;

R

43 and R 44 independently of the other are each hydrogen, cyano, nitro, halogen, (C-C)-alkyl, (Cl-C 8 )-haloalkyl, 30

(C

2

-C

8 )-alkenyl, (C 2

-C

8 )-haloalkenyl,

(C

2

-C

8 )-alkynyl,

(C

2

-C

8 )-haloalkynyl, (Cl-C)-alkoxy-(C 1

C

4 )-alkyl, (Cl-C 8 )-haloalkoxy-(C-C 4 )-alkyl, (C 1

C

8 )-alkylthio

(C-C

4 )-alkyl, (Ci-C 8 )-haloalkylthio-(Cl-C 4 )-alkyl,

(C

3

-C

8 )-cycloalkyl,

(C

4

-C

8 )-cycloalkenyl, (C3-C8)- 17 cycloalkyl-(C-C 4 )-alkyl, (C 4

-C

8 )-cycloalkenyl-(Cl C4) alkyl, aryl, heterocyclyl, aryl-(C 1

C

4 )-alkyl or heterocyclyl-(CC 4 )-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring 5 systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R 49 , or

R

43 and R 44 located at the same carbon atom together are an oxo group, 10 where

R

49 is (C-C 4 )-alkyl, (C-C 4 )-haloalkyl, (C 1

C

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

R

45 is hydrogen,

(C-C

8 )-alkyl, (C-C4)-haloalkyl, (C1C4) alkoxy, (Cl-C 4 )-alkylthio,

(C

3

-C

5 )-cycloalkyl, (C2-C4) 15 alkenyl, (C 2 -0 4 )-alkynyl, (Cl-C 4 )-alkanoyl,

(C

2

-C

4

)

haloalkanoyl, (C 2

-C

4 )-alkoxyalkyl, phenyl-(C-C 4 )-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 20 different substituents R 50 , where

R

50 is (C 1

-C

4 )-alkyl, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy,

(C

1

-C

4 )-alkylthio, halogen or cyano; or, if not included in the above definitions, 25 (c) is a group of the formula IV

Y

4

W

1 -Rt

Z

2 Ru where 30

Y

4 is a direct bond or CH 2 ;

Z

2 is oxygen, NR 51 , S(O)m where m = 0, 1 or 2; Ru and W1-Rt are substituents of the heteroaliphatic ring system, where Ru is hydrogen, halogen, cyano, (Cl-C 4 )-alkyl, (C1C4)- 18 haloalkyl, (C 2

-C

4 )-alkenyl, (C 2

-C

4 )-haloalkenyl,

(C

2

-C

4 )-alkynyl, (C 2

-C

4 )-haloalkynyl,

(C

3

-C

6 )-cyclo alkyl, (C 4

-C

6 )-cycloalkenyl, (Cl-C 4 )-alkoxy,

(C

1 C4) haloalkoxy, (Cl-C4)-alkanoyloxy,

(C

1

-C

4 )-haloalkanoyl 5 oxy, (Cl-C4)-alkylthio or (Cl-C 4 )-haloalkylthio; W1 is a direct bond, oxygen, -NR 52 -, -CO-, -COO-,

CONR

52 -, sulfur, -C=N-, -C=N-0- or -NR520-; Rt is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, where in the last 5 radicals one or more, 10 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, NR 53 or SiR 54

R

55 , and where these last 5 radicals with or without the variations mentioned may 15 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 3

R

56 , or Rt may be aryl or heterocyclyl, where both of these radicals may be unsubstituted or substituted by up to 20 three (in the case of fluorine up to the maximum number) identical or different radicals D 4

R

57 , or Ru and Rt together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the hetero atoms Y 4 and Z 2 and in 25 which one or two CH 2 groups, preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S(0)n where n = 0, 1 or 2, or NR38, where

R

51 is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (C2-04) 30 alkenyl, (C 2

-C

4 )-haloalkenyl,

(C

2

-C

4 )-alkynyl, (C2-C4) haloalkynyl, (Ci-C 4 )-alkoxy, (Cl-C 4 )-alkanoyl, (C2-C4) haloalkanoyl, (Ci-C 4 )-alkoxy- (Cl-C 4 )-alkyl, (Ci C4) alkylthio-(C-C 4 )-alkyl, (Ci-C 4 )-alkoxycarbonyl, (Cl-C 4 )-alkylsulfonyl, (Cl-C 4 )-haloalkylsulfonyl, 19 phenylcarbonyl, phenyl-(C 1

-C

4 )-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 5 R9, or

R

51 is CONR 6 0

R

61 where

R

60 and R 61 independently of the other are each hydrogen, (Cl-C 4 )-alkyl or phenyl, where the phenyl group may be unsubstituted or substituted by up to three (in the 10 case of fluorine up to the maximum number) identical or different substituents R 62 , and

R

62 and R 59 independently of the other are each (CC4) alkyl, (Cl-C4)-haloalkyl, (Cl-C4)-alkoxy, (Cl-C4) haloalkoxy, (Cl-C4)-alkylthio or halogen; 15

R

52 is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkanoyl or (C3-C5) cycloalkyl;

R

53 is hydrogen, (Cl C 4 )-alkyl, (C 1

C

4 )-alkoxy or (Cl-C4) alkanoyl;

R

54 and R 55 independently of the other are (Cl-C 4 )-alkyl, 20 preferably methyl;

R

58 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 25 different substituents R 63 ; R63 may be (C 1

C

4 )-alkyl, (C 1

C

4 )-haloalkyl, (C1C4) alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro or halogen, and the ring system formed by Ru and Rt may be unsubstituted or substituted by up to three, but 30 preferably one, substituents D 5

R

64 , or the ring system formed by Ru and Rt, 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, 20 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 Res, where 5

D

3 , D 4 , D 5 and D 6 are independent of one another and are each a direct bond, oxygen, S(O)k, S0 2 0, OS0 2 , CO, OCO, COO, S0 2

NR

66 , NR 66

SO

2 , NR 66 0, ONR 66 ,

NR

66 , NR 66 CO, CONR 66 or SiR 67

R

68 , where k = 0, 1 or 2; and 10

R

56 , R 57 , R 64 and R 65 independently of one another are each hydrogen, cyano, nitro, halogen, (C-C)-alkyl, (Cl-C 8 )-haloalkyl, (C 2

-C

8 )-alkenyl, (C 2

-C

8 )-haloalkenyl,

(C

2 -C)-alkynyl, (C 2

-C

8 )-haloalkynyl, (Cl-C 8 )-alkoxy (Cl-C 4 )-alkyl, (C 1

C

8 )-haloalkoxy-(Cl-C4)-alkyl, 15 (Cl-C 8 )-alkylthio-(Cl-C 4 )-alkyl, (Cl-C 8 )-haloalkylthio (Cl-C4)-alkyl, (C 3

-C

8 )-cycloalkyl, (C 4

-C

8 )-cycloalkenyl,

(C

3

-C

8 )-cycloalkyl-(Cl-C 4 )-alkyl, (C 4

-C

8 )-cycloalkenyl (Cl-C 4 )-alkyl, aryl, heterocyclyl, aryl-(Cl-C 4 )-alkyl or heterocyclyl-(C-C 4 )-alkyl, where in the last 8 radicals 20 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 R 69 , where

R

66 independently of the others is hydrogen, (Cl-C 4 )-alkyl, 25 (C-C4)-alkanoyl or (C 3

-C

5 )-cycloalkyl and

R

67 and R 68 independently of the other are each (C1C4) alkyl, and R69 independently of the others may be (Cl-C 4 )-alkyl, (Ci

C

4 )-haloalkyl, (Cl-C 4 )-alkoxy, (C 1

-C

4 )-haloalkoxy, 30 cyano, nitro, halogen,

(C

1

C

4 )-alkanoyl or (C2-C4) haloalkanoyl, or two of the radicals

R

56 , R 57 , R 64 , R 65 , R 69 which are located at the same carbon atom together, and in each case independently of the others, are an oxo group; 21 in particular those groups of the formula IV where Rt is hydrogen, (Cl-C 8 )-alkyl, (C 2

-C

8 )-alkenyl,

(C

2

-C

8

)

alkynyl, (C 3

-C

8 )-cycloalkyl or (C 4 -C)-cycloalkenyl and where in the last 5 radicals one or more, preferably up 5 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, NR 53 or SiR 54

R

5 5 , and where these last 5 radicals with or without the variations mentioned may be substituted 10 by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D 3

R

56 , or Rt may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in 15 the case of fluorine up to the maximum number) identical or different radicals D 4

R

57 , or Ru and Rt together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms Y 4 and Z 2 , and in 20 which one CH 2 group may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or

NR

58 , where

R

53 is hydrogen, (Cl-C 4 )-alkyl, (C 1

C

4 )-alkoxy or (C1C4) alkanoyl and 25

R

54 and R 55 independently of the other are (C 1

C

4 )-alkyl, preferably methyl;

R

58 is hydrogen, (0 1

-C

8 )-alkyl, (Cl-C 8 )-alkanoyl, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case 30 of fluorine up to the maximum number) identical or different substituents R 63 , and R63 may be (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (C1C4) alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro or halogen, and the ring system formed by Ru and Rt may be 22 unsubstituted or substituted by up to three, but preferably one, substituents D 5

R

64 , or the ring system formed by Ru and Rt, together with a further benzene ring or cyclohexane ring, forms a condensed ring 5 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) 10 identical or different substituents D Res, where in the compounds where the carbon atom between Y 4 and

Z

2 where Y = CH 2 only carries the substituent W1-Rt, the substituents X and W 1 -Rt are cis to each other;

D

3 , D 4 , D 5 and D 6 are independent of one another and are 15 each a direct bond, oxygen, S(O)k, S0 2 0, OS0 2 , CO, OCO, COO, S0 2

NR

66 , NR 66

SO

2 , NR 66 0, ONR 66 ,

NR

6 6 , NR 66 CO or CONR 66 , and k = 0, 1 or 2,

R

66 independently of the others is hydrogen, (Cl-C 4 )-alkyl, (Cl C 4 )-alkanoyl or (C 3

-C

5 )-cycloalkyl and 20

R

56 , R 57 , R 64 and R 65 independently of one another are each hydrogen, cyano, nitro, halogen, preferably fluorine, (C-C)-alkyl, (C 3

-C

8 )-cycloalkyl, aryl, heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or 25 substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R 69 , where

R

69 independently of the others may be (Cl-C 4 )-alkyl, (Cl

C

4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, 30 cyano, nitro, halogen, or two of the radicals

R

56 , R 57 , R 64 , R 65 , R 69 which are located at the same carbon atom, together and in each case independently of the others, are an oxo group; 23 (13) R 4 is hydrogen, halogen, (C-C 4 )-alkyl; (14) R 5 is hydrogen, halogen, (Cl-C 8 )-alkyl, (C 2

-C

8 )-alkenyl, (C2-C8) alkynyl, aryl or (C 3

-C

8 )-cycloalkyl, where aryl is as defined under (8); 5 M II (15) E is -C-, where M is oxygen, sulfur or NR 0 and R 70 is aryl, heteroaryl, substituted heteroaryl, hydroxyl, (Cl-C 8 )-alkoxy, aryloxy, heteroaryloxy, substituted heteroaryloxy, mono- or 10 disubstituted amino, where aryl is as defined under (8); (16) R 6 is (C 1

-C

20 )-alkyl, (C 2

-C

20 )-alkenyl,

(C

2

-C

20 )-alkynyl, (C3-C8) cycloalkyl, aryl or heteroaryl; and, if not included in the above definitions, the carbon radicals mentioned under (13) to (16) may be substituted by 15 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, cycloalkyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, and the aryl and heteroaryl radicals mentioned under (16) 20 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 Z"-R , where

Z

1 ' is a direct bond, NR 33 , 0, S(O)s where s = 0, 1 or 2, OSO2, SO20, NR 34

'SO

2 , S0 2

NR

35 ', SiR 36

'R

37 ' or U'-C-V', 25 || W' where

R

36 ' and R 37 ' are each (Cl-C 4 )-alkyl or phenyl, preferably methyl; U' is a direct bond, NR 38 ' or 0; 30 W' is oxygen or sulfur, preferably oxygen; V' is a direct bond, NR 39 ' or oxygen, where

R

33 ', R 34 ', R 35 ', R 38 ' and R 39 ' are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl; Rq are substituents which are independent of one another, and 35 each is halogen, hydroxyl, cyano, nitro, (Cl-C 20 )-alkyl, 24

(C

2

-C

20 )-alkenyl, (C 2

-C

20 )-alkynyl, (C 3

-C

8 )-cycloalkyl,

(C

4

-C

8 )-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 5 units such as oxygen, S(O)x where x = 0, 1 or 2, NR 40 ' or SiR 41

'R

42 ', 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 Dl'R 43 , or 10 Rq 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 D2'R 44 , or two adjacent radicals Z"-Rq may, together with the carbon atoms that they are attached to, 15 form a fused cycle having 4 to 6 ring atoms which is carbocyclic or contains hetero ring atoms selected from the group consisting of 0, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Cl-C 4 )-alkyl and oxo, or 20 R 33 ', R 35 ' or R 39 ' may, independently of one another, together with the Rq located at Z' form a 4- to 8-membered ring system in which one or two CH 2 groups, preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S( 0 )t where t = 0,1 or 2 or NR 25 where

R

40 ' is hydrogen, (Cl-C4)-alkyl,

(C

1

C

4 )-alkoxy or (C1C4) alkanoyl;

R

41 and R 42 ' independently of the other are each (C-C 4 )-alkyl, preferably methyl; 30 D' and D2' are independent of each other and each is a direct bond, oxygen, S(O)k, S0 2 0, OSO 2 , CO, OCO, COO, NR 4 6 ' S0 2

NR

46 ', NR 46

'SO

2 , ONR 46 ', NR 46 0, NR 46 'CO, CONR 46 ' or SiR 47

'R

48 ', and k = 0, 1 or 2, where

R

46 ' independently of the others is hydrogen, (Cl-C 4 )-alkyl, 25 (Cl-C4)-alkanoyl or (C 3

-C

5 )-cycloalkyl;

R

47 ' and R 48 ' independently of the other are each (C-C 4 )-alkyl;

R

43 ' and R 44 ' independently of the other are each hydrogen, cyano, nitro, halogen, (C-C)-alkyl, (Cl-C 8 )-haloalkyl, (C2-C8) 5 alkenyl, (C 2

-C

8 )-haloalkenyl,

(C

2

-C

8 )-alkynyl, (C2-Cs) haloalkynyl, (C1-C 8 )-alkoxy-(C 1

-C

4 )-alkyl, (Cl-C 8 )-haloalkoxy (Cl-C4)-alkyl, (Cl-C8)-alkylthio-(Cl-C4)-alkyl, (Cl-C8) haloalkylthio-(Cl-C 4 )-alkyl, (C 3

-C

8 )-cycloalkyl, (C4-C8) cycloalkenyl,

(C

3

-C

8 )-cycloalkyl-(Cl-C 4 )-alkyl, (C 4

-C

8

)

10 cycloalkenyl-(Cl-C 4 )-alkyl, aryl, heterocyclyl, aryl-(Cl-C4) alkyl or heterocyclyl-(Cl-C 4 )-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 15 substituents R 49 , or

R

43 ' and R 44 ' located at the same carbon atom together are an oxo group, where

R

49 ' is (C-C 4 )-alkyl, (Cl-C4)-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C4) 20 haloalkoxy, cyano, nitro or halogen;

R

45 ' is hydrogen, (C-C)-alkyl, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-alkylthio,

(C

3

-C

5 )-cycloalkyl,

(C

2

-C

4 )-alkenyl, (C2-C4) alkynyl, (Cl-C 4 )-alkanoyl,

(C

2

-C

4 )-haloalkanoyl, (C2-C4) alkoxyalkyl, phenyl-(C 1

C

4 )-alkyl or phenyl and the phenyl 25 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 5 o, where

R

50 ' is (C 1

C

4 )-alkyl, (C 1

C

4 )-haloalkyl,

(C

1

C

4 )-alkoxy, (C1C4) alkylthio, halogen or cyano. 30 An inorganic anion is an anion of an inorganic acid, for example F, C, Br~, I~, N0 3 ~, SO 4 2 -, HSO4, P0 4 3 -, HP0 4 2 -, H2PO4~, PO3 ~ or

N

3 ~, or a complex anion, for example BF 4 ~, PF6~ or tetraphenylborate.

26 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, 5 anions of mono- or bifunctional carboxylic acids and hydroxy 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 10 1,5-naphthalenedisulfonic acid, or saccharine. 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 15 N*R and D is nitrogen). If Z is (C 3

-C

8 )-cycloalkyl or (C-C)-cycloalkenyl, it is preferably substituted by one or more, preferably up to 3, identical or different substituents selected from the group consisting of (Cl-C 12 )-alkyl, 20 (C 3

-C

8 )-cycloalkyl, (C 3

-C

8 )-cycloalkyl-(C-C 4 )-alkyl, (Cl-C,)-alkoxy,

(C

3

-C

8 )-cycloalkoxy, (C1 C 4 )-alkoxy-(C 1

-C

4 )-alkyl, (C 3

-C

8 )-cyclo alkyl-(Cl-C 4 )-alkoxy, tri-(0 1

-C

8 )-alkylsilyl, preferably dimethyl (Cl -C 8 )-alkylsilyl or triethylsilyl, di-(Cl -C 8 )-alkyl-(C 3

-C

8 )-cycloakyl silyl, preferably dimethylcyclohexylsilyl, di-(Cj C 8 )-alkyl-(phenyl 25 (Cl-C 4 )-alkyl)-silyl, preferably dimethyl(phenyl-(C-C 4 )-alkyl)silyl, di-(Cl-C 8 )-alkyl-(Cl-C 4 )-haloalkylsilyl, preferably dimethyl-(C C4) haloalkylsilyl, dimethylphenylsilyl, (Cl-C 4 )-haloalkyl, halogen, (Cl-C 4 )-haloalkoxy, heteroaryl, phenyl, phenyl-(Cl-C 4 )-alkyl, benzyloxy, benzyloxy-(Cl-C 4 )-alkyl, benzylthio, phenylthio and 30 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 (Cl 0)-alkyl, (C 3

-C

8 )-cycloalkyl (Cl-C 4 )-haloalkyl, preferably trifluoromethyl, halogen, (Cl-C 4 )-dialkylamino, (Cl-C 4 )-alkylthio, 27

(

0 i-C 8 )-alkoxy, (C C 4 )-haloalkoxy, (C1 C 4 )-alkoxy-(C 1

-C

4 )-alkoxy,

H

5

C

2

-O-[CH

2

-CH

2 -0-]x, 2-(tetrahydro-2H-pyran-2-yloxy)ethoxy,

(C

2

-C

8 )-alkenyl, (C 2

-C

8 )-alkynyl, benzyloxy, which may carry one or two identical or different substituents selected from the group 5 consisting of (Cl-C 4 )-alkyl, (C-C 4 )-haloalkyl, (Cl-C4)-alkoxy, (Cl-C 4 )-haloalkoxy and halogen in the phenyl moiety, tri-(Cl-C 4

)

alkylsilylmethoxy, preferably dimethyl-(Cl-C 4 )-alkylsilylmethoxy,

(C

3

-C

8 )-cycloalkyl-(Cl-C 4 )-alkoxy, 1,3-dioxolan-2-ylmethoxy, tetra hydrofuran-2-ylmethoxy and tetrahydro-2H-pyran-2-ylmethoxy. 10 Preference is given to compounds of the formula I in which 15 A isCHandDisN*R or A is nitrogen and D is N+R; 20 Qn- is an anion such as Hal~, NO 3 ~, BF4~, BPh 4 ~ or PF63 R' is hydrogen, methyl, fluorine or chlorine;

R

2 and R 3 are each hydrogen, (Cl-C 4 )-alkyl, (C 2

-C

4 )-alkenyl, (C2-C4) alkynyl, amino, (Cl-C 4 )-alkylamino, (Cl-C 4 )-dialkylamino, trimethyl 25 silylethynyl, methoxycarbonyl, (Cl-C 4 )-haloalkyl,

(C

2

-C

4

)

haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or

R

2 and R 3 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 CH 2 30 unit; or

R

2 and R 3 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 CH 2 unit; X is NH or oxygen.

28 Equally, preference is given to compounds of the formula I in which Y is a bond or a methylene group which is substituted by one or two, preferably by one, (Cl-C4)-alkyl radical; and 5 Z is (0 3

-C

8 )-cycloalkyl or (0 5

-C

8 )-cycloalkenyl, where a CH 2 group of the carbocycle may be replaced by NR 20 ;

R

20 is phenyl or substituted phenyl and the (C 3

-C

8 )-cycloalkyl or

(C

5

-C

8 )-cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum 10 number), identical or different radicals selected from the group consisting of (ClC,,)-alkyl,

(C

3 -C)-cycloalkyl, 15 (C 3

-C

8 )-cycloalkoxy, (C2-C1,)-alkenyl, (C2-C1 8 )-alkynyl, (C-C12 )-alkoxy, (Cl-C 12 )-alkanoyloxy, 20 formyl, (C2-C1 2 )-acyl, (Cl-C1 2 )-alkyl-oxycarbonyl, SiR21 R 22

R

2 3

NR

2 4

R

25 , 25 0

C-NR

2 4

R

25 , hydroxyl, halogen, 30 aryl, heteroaryl, 0 aryl, 0 heteroaryl,

CH

2 0 aryl, 29

CH

2 0 heteroaryl, (C1-C,)-alkanediyldioxy, (C-C1 3 )-alkyl-oximino and

(C

2

-C

18 )-alkylidene and where, if not included in the 5 above definitions, one or more, preferably up to three, CH 2 groups in the (C01-018)-, (C2-C18)-, (C1-C12)-, (C2-C12)- and (C1-C13) hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as 0, NR'O" or SiR 11

"R

12 ", these hetero atom radicals preferably not being adjacent to one another, where R 10 ", R"" and 10 R 12 " have the meanings of R 1 O, R 11 , R 12 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 15 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 20 three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R 24 and R 25 are identical or different and are each independently of the other hydrogen, (Cl-C 4 )-alkyl, (C-C 4 )-acyl, 25 (C 3

-C

6 )-cycloalkyl, phenyl and substituted phenyl and where R 2 1,

R

22 , R 23 are identical or different and are each independently of the others (C-C1 8 )-alkyl, (C-C1 8 )-alkoxy, (C 3

-C

8 )-cycloalkyl and aryl, where in the (C-C1 8 )-hydrocarbon radicals more than one, preferably up to three, CH 2 groups may be replaced by oxygen and 30 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 21 and R 22 ) attached to silicon together to form a cycle, the silicon atom possibly being part of this cycle, and where additionally these (Cl-C1 8 )-hydrocarbon radicals with or without the 30 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 (C 3

-C

8 )-cycloalkyl or (C 5

-C

8 )-cyclo 5 alkenyl 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 10 Y is a bond; and Z (a) is a group of the formula il

X

1 RY 15 Rz where X 1 is oxygen; RY is (Cl-C 20 )-alkyl, (C 2 -0 20 )-alkenyl, (C 2

-C

20 )-alkynyl, aryl or hetero cyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up 20 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 SiR 27

R

28 , where

R

27 and R 28 are each (Cl-C 4 )-alkyl, preferably methyl, 25 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 30 radicals selected from the group consisting of halogen, preferably fluorine, aryl, aryloxy, arylthio, (C 3

-C

8 )-cycloalkoxy,

(C

3

-C

8 )-cyclo alkylthio, heterocyclyl, heterocyclyloxy or (Cl-C 2 )-alkoxycarbonyl, where the where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be 31 unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or RV and Rz together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system 5 containing the hetero atoms X 1 , and where one CH 2 group may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR where R 29 is hydrogen, (C 1 -C)-alkyl, (C1-C 8 )-alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be 10 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 RV and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C1 15 C 8 )-alkyl, (C 3

-C

8 )-cycloalkyl, aryl or aryl-(Cl-C 4 )-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, 20 or where the ring system formed by RV and Rz, 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 25 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 30 Rz is hydrogen or (b) is a group of the formula (Ill) 32 (

Y

3 5 where yl, y 2 and Y 3 are each a group of the formula -0-, -S(O)r-, where r = 0, 1 or 2 or is a group of the formula CR31 R 32 , or Y' or y3 stands in place of a direct bond, where 10 R 31 and R 32 independently of the other are each hydrogen or methyl; m 1 is 1 or 2; n 1 is 1 or 2;

Z

1 is a direct bond, NR 33 , 0, S(O)s where s = 0, 1 or 2, OS0 2 , 15 S0 2 0, NR 34

SO

2 , S0 2

NR

35 , S1R 36

R

37 or U-C-V, where 11 W U is a direct bond, NR 38 or 0; W is oxygen; 20 V is a direct bond, NR 39 or oxygen; and

R

36 and R 37 are each (Cl-C 4 )-alkyl or phenyl, preferably methyl;

R

33 , R 34 , R 35 , R 38 and R 39 are identical or different and are each hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkoxy, (C1-C 4 )-alkanoyl or 25

(C

3 -C)-cycloalkyl; Rq independently of the others is (Cl-C 8 )-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, 30 preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D 1

R

43 , or Rq 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 33 radicals D 2

R

44 ; D' and D 2 are independent of one another and are each a direct bond, -0-, -S(O)k-, -S0 2 0-, -OSO 2 -, -Co-, -OCO-, -COO-,

-NR

4 6 -, -S0 2

NR

46 -, -NR 46 S0 2 -, -ONR 4 6 -, -NR 46 0-, 5 -NR 46 CO-, -CONR 46 -, and k = 0, 1 or 2, and where

R

46 independently of the others is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkanoyl or (C 3

-C

5 )-cycloalkyl;

R

43 and R 44 independently of the other are each hydrogen, halogen, preferably fluorine, (Cl-C 8 )-alkyl, (C 3

-C

8 )-cycloalkyl, aryl or 10 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 R 49 , where 15 R 4 9 independently of the others may be (Cl-C4)-alkyl, (C1C4) haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro, halogen; or, 20 (c) is a group of the formula IV Y4 W1-Rt _ZK Ru (IV) 25 where

Y

4 is a direct bond or CH 2 ;

Z

2 is oxygen; Ru is hydrogen, (Cl-C 4 )-alkyl, tirfluoromethyl or (Cl-C 4 )-alkoxy; 30 W1 is a direct bond, oxygen, -CO-, -COO-, CONR 52 , sulfur, -C=N-, -C=N-0- where R 5 2 is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkanoyl and (C 3

-C

5 )-cycloalkyl, and Rt is as defined above under (12 c).

34 Particular preference is given to compounds of the formula I in which

R

1 is hydrogen;

R

2 and R 3 are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3) alkenyl, amino, (Cl C 4 )-alkylamino,

(C

1

C

4 )-dialkylamino, (C2-C3) 5 chloro- or -fluoroalkenyl, (C 2

-C

3 )-alkynyl, trimethylsilylethynyl,

(C-C

3 )-chloro- or -fluoroalkyl, methoxymethyl, halogen or cyano; or

R

2 and R 3 together with the ring system to which they are attached form the quinazoline or quinoline system, which may be fluorine substituted in the carbocyclic moiety; or 10 R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 6-membered ring, which may contain an oxygen or sulfur atom instead of a CH 2 group; in particular those compounds where 15 R 1 is hydrogen;

R

2 is methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (Cl-C 2 )-fluoroalkyl or methoxymethyl;

R

3 is fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C-C2)-fluoro alkyl, amino, (Cl-C 2 )-alkylamino, (Cl-C 2 )-dialkylamino or methoxy; 20 or, in the case that A is nitrogen,

R

2 and R 3 form, together with the ring system to which they are attached, the quinazoline system, which may be substituted by one fluorine atom. 25 Likewise, particular preference is given to compounds of the formula I in which X is NH; Y is a bond; and Z (a) is cyclopentyl or cyclohexyl, where both radicals may be 30 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 1i 35 X RY X Rz 5 where

X

1 is oxygen; Rz is hydrogen; or (c) is a group of the formula Ill 10 3 (y 2 )(Z - R )W where 15 Y1 is CH 2 ;

Y

2 is CH 2 ;

Y

3 is CH 2 , O or a direct bond; mi is 1 or 20 (d) is a group of the formula IV y4 W1-Rt :ZK Ru (IV) 25 where

Y

4 is a direct bond or CH 2 ; z 2 is oxygen; Ru is hydrogen or methyl; 30 in particular those compounds where Z (a) is cyclohexyl which is preferably substituted by a radical selected from the group consisting of (CS-C 8 )-alkyl, 35

(C

3 -C)-cycloalkyl, 36

(C

3 -C)-cycloalkoxy,

(C

2

-C

8 )-alkenyl,

(C

2 -C)-alkynyl, (Cl-C 8 )-alkoxy, 5 (C 1

-C

8 )-alkyloxycarbonyl, SiR 2

'R

22

R

23 , 0

-C-NR

24

R

25 , 10 aryl, heteroaryl, O aryl, o heteroaryl,

CH

2 0 aryl, 15 CH 2 0 heteroaryl, (Cl-C 8 )-alkanediyldioxy and (Cl-C 1 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 20 more, preferably up to three, CH 2 groups in the (C1-C8)-,

(C

2 -CO)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals, such as 0, or SiR 11

"R

12 , where R 1 1 and R 12 " have the meanings of R 11 , R 12 , and where additionally 3 to 6 carbon atoms of these hydrocarbon 25 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, 30 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); 37

R

24 and R 25 are identical or different and independently of one another are each hydrogen, (Cl-C 4 )-alkyl, phenyl and substituted phenyl, and R 21 , R 22 , R 23 are identical or different and independently of one another are each (C 1 C-)-alkyl, 5 (C-C)-alkoxy, (C 3

-C

8 )-cycloalkyl and aryl, where in the

(C

1

C

8 )-hydrocarbon radicals more than one, preferably up to three, CH 2 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 10 cycle, and where additionally these (Cl-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; 15 or (b) is a group of the formula (II) X RY

-

XK RZ 20 where

X

1 is oxygen; Rz is hydrogen; RY is (C 1 -0 15 )-alkyl, aryl or heterocyclyl meaning a hetero 25 aromatic 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 30 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 38 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 5 the heteroaliphatic six-membered ring are preferably cis to one another; or (c) is a group of the formula (Ill) -y 3 10 (Z'-Rq)n where n' 1 is 1 or 2; 15 Rq independently of the others is (C 1

-C

8 )-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 20 the case of fluorine up to the maximum number), identical or different radicals D R 43 , or Rq 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), 25 identical or different radicals D 2

R

44 . or (d) is a group of the formula IV y4 W1-Rt 30 Z Ru (IV) where Ru is hydrogen; Rt is (Cl-C 8 )-alkyl in which one or more, preferably up to three, nonadjacent saturated carbon units may be 39 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 5 D 3

R

56 , or Rt 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 4

R

57 10 Furthermore, particular preference is given to compounds of the formula I in which A is CH and D is N*R or 15 A is nitrogen and D is N*R; Q~ is an inorganic or organic anion, such as Hal~, NO 3 ~, BF4-, BPh , PFel4

R

4 is hydrogen; 20 R 5 is hydrogen, halogen, (0 1

-C

8 )-alkyl, (Cl-C 8 )-haloalkyl, (C2-C8) alkenyl, (C 2

-C

8 )-alkynyl; M || E is -C- , where M is oxygen or sulfur; 25 R 6 is aryl or heteroaryl, where the aryl and heteroaryl 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 Z"-Rq, where

Z

1 is a direct bond, 0, OS0 2 or U'-C-V', where 30 11 W' U' is a direct bond, or 0; W' is oxygen; V' is a direct bond, NR 39 ' or oxygen; 35 and 40

R

39 ' is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-alkanoyl or

(C

3 -C.)-cycloalkyl; Rq are substituents which are independent of one another and are each (Cl-C 20 )-alkyl or (C 2

-C

20 )-alkenyl and may be substituted by one or 5 more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D 1

R

43 ', or Rq is halogen, hydroxyl, nitro or cyano, or Rq may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up 10 to the maximum number) identical or different radicals D 2

'R

44 '; D" and D 2 ' are independent of one another and are each a direct bond, -O-, -S(O)k-, -S0 2 0-, -OSO 2 -, -CO-, -OCO-, -COO-, -NR 46 '-, -S0 2

NR

46 '-, -NR 46

'SO

2 -, -ONR 46 '-, -NR 46 'O-, -NR 46 'CO-, -CONR 46

'_

and k = 0, 1 or 2, and where 15 R 46 ' independently of the others is hydrogen, (Cl-C 4 )-alkyl, (C1C4) alkanoyl or (C 3

-C

5 )-cycloalkyl;

R

43 ' and R 44 ' independently of each other are each hydrogen, halogen, preferably fluorine, (Cl-C 8 )-alkyl, (C 3

-C

8 )-cycloalkyl, aryl or heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic 20 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 R 49 , where

R

49 ' independently of the others is (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (C 1

-C

4 )-haloalkoxy, cyano, nitro, halogen. 25 Most particularly preferred are those compounds of the formula I in which

R

1 is hydrogen;

R

2 is ethyl or methoxymethyl;

R

3 is chlorine, bromine or methoxy, preferably those for which R2 is 30 ethyl and R 3 is chlorine;

R

4 is hydrogen;

R

5 is hydrogen or methyl; M 11 41 E is -C- , where M is oxygen;

R

6 is aryl or heteroaryl, where the aryl and heteroaryl 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 5 Z"-Rq, where

Z

1 , is a direct bond, 0 or U'-C-V', where || W' U' is a direct bond, or 0; 10 W' is oxygen; V' is a direct bond, NR 39 ' or oxygen; and

R

39 ' is hydrogen, (C-C 4 )-alkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-alkanoyl or

(C

3

-C

5 )-cycloalkyl; 15 Z"-Rq together are halogen, nitro or cyano, or Rq are substituents which are independent of each other and are each

(C

1

C

12 )-alkyl or (C 2

-C

12 )-alkenyl and which 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 R 43 , or 20 Rq 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 2

R

44 '; DE 2 are independent of one another and are each a direct bond, -0-, -S(O)k-, -S0 2 0-, -OSO 2 -, -CO-, -OCO-, -COO-, -NR 4 '-, 25 -S0 2

NR

46 '-, -NR 46

'SO

2 -, -ONR 46 '-, -NR 46 '0-, -NR 46 'CO-, -CONR 46 ', and k = 0, 1 or 2, and where

R

46 ' independent of the others is hydrogen, (C 1

C

4 )-alkyl, (Cl-C4) alkanoyl or (C 3 -C)-cycloalkyl;

R

43 ' and R 44 ' independently of the other are each hydrogen, halogen, 30 preferably fluorine, (C-C)-alkyl, (C 3

-C

8 )-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 R 4 9 , where 42

R

49 ' independently of the others may be (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro, halogen. In the above formulae (1) to (IV), the radicals alkyl, alkoxy, haloalkyl, 5 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. 10 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 15 unsaturated radicals which are possible and which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methyl prop-2-en-1 -yl, but-2-en-1 -yl, but-3-en-1 -yl, 1 -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. 20 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. 25 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 30 monohaloalkyl, perhaloalkyl, CF 3 , CHF 2 , CH 2 F, CF 3

CF

2 , CH 2 FCHCI, CC13, CHC1 2 , CH 2

CH

2 Cl; haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F,

CF

3

CF

2 0, OCH 2

CF

3 and OCH 2

CH

2 Cl; the same applies analogously to haloalkenyl and other halogen-substituted radicals.

43 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, cyclo 5 alkenyl 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 hydrocarbonoxy radical. 10 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 15 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, 0, S, SO, SO 2 ; 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 20 hetero units. The heterocyclic radical can be, for example, a hetero aromatic 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 25 up to 3, -CH=CH-units is replaced by NH, S or 0, 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 30 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.

44 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 5 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 10 dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkyl sulfonyl and, in the case of cyclic radicals, also alkyl, cycloalkyl and halo alkyl; 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 15 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, (C-C 4 )-alkyl, 20 preferably methyl or ethyl, (Cl-C 4 )-haloalkyl, preferably trifluoromethyl, (Cl-C 4 )-alkoxy, preferably methoxy or ethoxy, (Cl-C 4 )-haloalkoxy, nitro and cyano. Especially preferred are the substituents methyl, methoxy and chlorine. 25 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 30 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 (Cl-C 4 )-alkanoyl. The same applies analogously to substituted hydroxylamino or hydrazino.

45 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, (Cl-C 4 )-alkyl, (Cl-C4)-alkoxy, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-halo 5 alkoxy 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 10 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 [(Cl-C 4 )alkyl] 15 carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxy carbonyl, 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, 20 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-(Cl-C 8 )-alkylsilyl 25 ethynyl" denotes, for example, the trimethylsilylethynyl or the tert-butyl dimethylsilylethynyl group; the term "(Cl-C 4 )-hydroxyalkyl" denotes, for example, the hydroxymethyl, 1 -hydroxyethyl, 2-hydroxyethyl, 1 -hydroxy-1 -methylethyl or the 1 -hydroxy propyl group; 30 the term "(Cl-C 4 )-alkanoyl" denotes, for example, the formyl, acetyl, propionyl, 2-methylpropionyl or butyryl group; the term "(Cl-C 12 )-alkanoyl" denotes, for example, the abovementioned radicals and, for example, the valeroyl, pivaloyl, hexanoyl, decanoyl or the dodecanoyl group; 46 the term "(C 2

-C

4 )-haloalkanoyl" denotes a (Cl-C 4 )-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 "(C 2

-C

12 )-haloalkanoyl" denotes a (C-C 20 )-alkanoyl group in 5 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 1

-C

4 )-alkyl" denotes a cyanoalkyl group whose hydrocarbon radical has the meanings given for the term "(C 1

-C

4 )-alkyl"; the term "(Cl-C 4 )-alkylamino" denotes, for example, methylamino, 10 ethylamino, isopropylamino; the term "(C 1

-C

4 )-dialkylamino" denotes, for example, dimethylamino, N-ethyl-N-methylamino, diethylamino, the term "(Cl-C 4 )-alkoxycarbonyl" denotes, for example, the methoxy carbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxy 15 carbonyl group; the term "(C 1

-C

12 )-alkoxycarbonyl" denotes the abovementioned radicals and, for example, the hexyloxycarbonyl, 2-methylhexyloxycarbonyl, decyloxycarbonyl or dodecyloxycarbonyl group; the term "(Cl-C 4 )-haloalkoxycarbonyl" denotes a (Cl-C 4 )-alkoxycarbonyl 20 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 "(Cl-C 4 )-haloalkylthio" denotes a (Cl-C 4 )-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 25 fluorine; the term "(Cl-C 4 )-alkylsulfinyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group; the term "(Cl-C 4 )-alkylsulfonyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group; 30 the terms "(Cl-C 4 )-haloalkylsulfinyl" and "(Cl-C 4 )-haloalkylsulfonyl" denote (Cl-C 4 )-alkylsulfinyl 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; 47 the term "(C 1

-C

4 )-alkoxy-(C 1

-C

4 )-alkyl" denotes, for example, a 1-methoxy ethylene group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a methoxy methyl or ethoxymethyl group, a 3-methoxypropyl group or a 4-butoxybutyl group; 5 the terms "(Ci-C 4 )-haloalkoxy-(Cl-C 4 )-alkyl", "(C1-C 4 )-alkoxy-(C 1

-C

4 )-halo alkyl" and "(Cl-C 4 )-haloalkoxy-(C-C4)-haloalkyl" denote (Cl-C 4 )-alkoxy (Cl-C 4 )-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 10 chlorine or fluorine; the term "(Cl-C4)-alkylthio-(Cl-C 4 )-alkyl" denotes, for example, methylthio methyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthio ethyl or 3-methylthiopropyl; the term "arylthio" denotes, for example, the phenylthio or the 1- or 15 2-naphthylthio group; the term "aryloxy" denotes, for example, the phenoxy- or 1- or 2-naphthyl oxy group; the term "heterocyclyloxy" or "heterocyclylthio" denotes one of the abovementioned heterocyclic radicals which are linked via an oxygen or 20 sulfur atom; the term "cycloalkoxy" or "cycloalkylthio" denotes one of the above mentioned cycloalkyl radicals which are linked via an oxygen or sulfur atom; the term "aroyl" denotes, for example, the benzoyl, naphthoyl or the 25 biphenylcarbonyl group; the term "aryl-(Cj-C 4 )-alkanoyl" denotes, for example, the phenylacetyl, 3-phenylpropionyl, 2-phenylpropionyl, 2-methyl-2-phenylpropionyl, 4-phenylbutyryl or the naphthylacetyl group; the term "(C 3

-C

8 )-cycloalkyl-(Cl-C 4 )-alkanoyl" denotes, for example, the 30 cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexyl carbonyl, cyclohexylacetyl or the cyclohexylbutyryl group; the term "heterocyclyl-(Cl-C 4 )-alkanoyl" denotes, for example, the thenoyl, furoyl, nicotinoyl, thienylacetyl or the pyridinepropionyl group; the term "(C 3

-C

8 )-cycloalkoxycarbonyl" denotes, for example, the 48 cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or the cycloheptyloxycarbonyl group; the term "(C 3

-C

8 )-cycloalkyl-(Cl-C 4 )-alkoxycarbonyl" denotes, for example, the cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentyl 5 oxymethoxycarbonyl, cyclohexyloxymethoxycarbonyl, 1-(cyclohexyl) ethoxycarbonyl or the 2-(cyclohexyl)ethoxycarbonyl group; the term "aryl-(C-C 4 )-alkoxycarbonyl" denotes, for example, the benzyl oxycarbonyl, 1-naphthylmethoxycarbonyl, 2 -naphthylmethoxycarbonyl, 1 -phenylethoxycarbonyl or the 2-phenylethoxycarbonyl group; 10 the term "heterocyclyl-(Cl-C 4 )-alkoxycarbonyl" denotes, for example, the thienylmethoxycarbonyl, furylmethoxycarbonyl, tetrahydrofurylmethoxy carbonyl or the pyridylethoxycarbonyl group; the term "aryloxycarbonyl" denotes, for example, the phenoxycarbonyl, naphthoxycarbonyl or the biphenyloxycarbonyl group; 15 the term "heterocyclyloxycarbonyl" denotes, for example, the tetrahydro pyran-4-oxycarbonyl group; the term "(Cl-C 20 )-alkanoyloxy" denotes, for example, the formyloxy, acetoxy, propionyloxy, butyryloxy, pivaloyloxy, valeroyloxy or the hexanoyloxy group; 20 the term "(C 2

-C

20 )-haloalkanoyloxy" denotes a (C 2 -C2 0 )-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 "(C 3

-C

8 )-cycloalkanoyloxy" denotes, for example, the cyclo 25 propanoyloxy, cyclobutanoyloxy, cyclopentanoyloxy, cyclohexanoyloxy or the cycloheptanoyloxy group; the term "(C 3

-C

8 )-cycloalkyl-(Cl-C 4 )-alkanoyloxy" denotes, for example, the cyclopropylcarbonyloxy, cyclopropylacetoxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cyclohexylacetoxy or the 30 4-cyclohexylbutyryloxy group; the term "aroyloxy" denotes, for example, the benzoyloxy or the naphthoyloxy group; the term "aryl-(Cl-C 4 )-alkanoyloxy" denotes, for example, the benzoyloxy, naphthoyloxy, biphenylcarbonyloxy, phenylacetoxy or the phenylbutyryloxy 49 group; the term "heterocyclyl-(C-C 4 )-alkanoyloxy" denotes, for example, the thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or the pyrimidinylcarbonyloxy group; 5 the term "(Cl-C 20 )-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 10 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 1 -C1,)-alkanediyldioxy" denotes a bivalent radical derived from (C -C 18 )-alkanes by replacement of two hydrogen atoms by two -O 15 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 20 such as oxygen, S(O)x where x = 0, 1 or 2, NR 26 or SiR 27

R

28 , where R 26 is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkoxy or (C-C 4 )-alkanoyl and where R 27 and R 28 are each (Cl-C 4 )-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 25 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, hetero cyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, 30 arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, halo alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxy carbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxy carbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkyl alkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkyl- 50 sulfonyloxy, 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 5 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: 10 alkoxyalkyl radicals, for example the methoxymethyl, methoxyethyl or ethoxyethyl group; or alkoxyalkoxyalkyl radicals, for example the methoxy- or the ethoxyethoxy ethyl group; or alkylthioalkyl radicals, for example the methyl- or the ethylthioethyl group; 15 or alkylsulfinylalkyl radicals, for example the methyl- or ethylsulfinylethyl group; or alkylsulfonylalkyl radicals, for example the methyl- or ethylsulfonylethyl group; or 20 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 octyldimethyl silyl group; or 25 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 30 example the benzyldimethylsilyl or the phenylethyldimethylsilyl group; or alkanoylalkyl radicals, for example the acetylmethyl or the pivaloylmethyl group; or 51 cycloalkanoylalkyl radicals, for example the cyclopropylcarbonylmethyl or the cyclohexylcarbonylmethyl group; or haloalkanoylalkyl radicals, for example the trifluoro- or trichloroacetylmethyl group; or 5 aroylalkyl radicals, for example the benzoyl- or naphthoylalkyl radicals, for example the phenylacetylmethyl group; or heterocyclylcarbonylalkyl radicals, for example the thienyl- or pyridylacetyl methyl group; or arylalkyl radicals, for example the benzyl, the 2-phenylethyl, the 10 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 15 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 20 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-butylcyclo hexyl group or the 1 -methylcyclopropyl, -cyclobutyl, -cyclopentyl- or -cyclohexyl group; 25 cycloalkylalkyl radicals, for example the cyclohexylmethyl or -ethyl group; or else haloalkyl derivatives of the appropriate groups, for example halo alkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkylcycloalkyl or halocycloalkyl radicals. This applies correspondingly to similar definitions. 30 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 stereo- 52 isomers 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 5 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. 10 The invention furthermore relates to a process for preparing compounds of the formula I which comprises reacting a compound of the formula (V) X-Y-Z 15 (V) R2 N R where G is CH or N and R 1 , R 2 , R 3 , X, Y and Z are each as defined under formula I, with an electrophile of the formula (VI) 20 L E -- 6 R (VI) R 4 R 25 where R 4 , R 5 , R 6 and E are each 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, AgBF 4 , AgNO 3 or Nal, replacing, if appropriate, the anion of the compounds obtained in 30 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].

53 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]. 5 The structures (V) and (VI) can be varied within wide limits. The abovementioned reaction is carried out in a temperature range from 20 to 1500C, if appropriate in an inert organic solvent such as acetonitrile, 10 acetone, 2-butanone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene. It is also possible to use mixtures of the solvents mentioned. 15 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 20 methods. Compounds of the formula (VI) are commercially available, or they can be obtained by processes known in principle [for example: Verh6, De Kimpe, in "The Chemistry of Functional Groups, Supplement D" (Patai, Rappoport, 25 Eds.), Part 1, p. 813 ff., Wiley, New York, 1983]. While being tolerated well by plants and having favorable toxicity toward warm-blooded animals, the active substances are suitable for controlling animal pests, especially insects, arachnids, helminths and molluscs, and 30 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: 54 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., 5 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. 10 From the order of the Chilopoda, for example, Geophilus carpophagus 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. 15 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. 20 From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp. From the order of the Mallophaga, for example, Trichodecte spp. and Damalinea spp. 25 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. 30 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 55 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, 5 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, 10 Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa 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. 15 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 20 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 25 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., 30 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 56 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 5 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. 10 From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp. From the class of the Bivalva, for example, Dreissena spp. 15 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 20 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), 25 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 30 (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 57 and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (leaf-gall nematodes, such as Anguina tritici). 5 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 10 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 15 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 20 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 25 described, for example, in: Winnacker-KOchler, "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. 30 London. The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in: 58 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 5 Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Sch6nfeldt, "Grenzflichenaktive Athylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker KOchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 10 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 15 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, polyoxy ethylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2' 20 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 25 alkylarylsulfonates, such as calcium 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, polyoxy ethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters. 30 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 adsorptive, granulated inert material or 59 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 5 granulated in the fashion conventional for the preparation of fertilizer granules, if desired as a mixture with fertilizers. In wettable powders, the concentration of active substance is, for example, from approximately 10 to 90% by weight, the remainder to 100% by weight 10 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 15 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 20 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 25 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. 30 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.

60 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, 5 nematicides, fungicides, growth regulators or herbicides. The pesticides include, for example, phosphates, carbamates, carboxylates, formamidines, tin compounds and substances produced by microorganisms, inter alia. 10 Preferred mixture components are 1. from the group of the phosphorus compounds acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, 15 bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos methyl, demeton, demeton-S-methyl, demeton-5-methylsulfphone, dialifos, diazinon, dichlorvos, dicrotophos, 0,0-1,2,2,2-tetrachloroethyl phosphoro thioate (SD 208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, 20 fonofos, formothion, heptenophos, isozophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, pirimiphos, pirimiphos-ethyl, pirimiphos 25 methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tetra chlorvinphos, thiometon, triazophos, trichlorphon, vamidothion; 2. from the group of the carbamates 30 aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbo furan, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6,9-triaza 4-benzyl-6,1 0-dimethyl-8-oxa-7-oxo-5, 11 -dithia-9-dodecenoate (OK 135), 61 1 -methylthio(ethylideneamino)-N-methyl-N-(morpholinothio)carbamate (UC 51717); 3. from the group comprising the carboxylates 5 allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1 R)-cis-2,2-dimethyl 3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bioallethrin, bioallethrin ((S)cyclopentyl isomer), bioresmethrin, biphenate, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methy (1RS)-trans-3-(4-tert-butyl phenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, 10 cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D-isomers), permethrin, phenothrin ((R)-isomers), d-prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, tralomethrin; 15 4. from the group of the amidines amitraz, chlordimeform; 5. from the group of the tin compounds 20 cyhexatin, fenbutatin oxide; 6. others abamectin, Bacillus thuringiensis, bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron, 25 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), clorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazine, ethyl N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl) carbamoyl)-2-chlorobenzocarboximidate, DDT, dicofol, N-(N-(3,5-dichloro 4-(1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,6-difluorobenzamide 30 (XRD 473), diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene) 2,4-xylidine, dinobuton, dinocap, endosulfan, ethofenprox, (4-ethoxy phenyl) (dimethyl)(3-(3-phenoxyphenyl)propyl)silane, (4-ethoxyphenyl)(3 (4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane, fenoxycarb, 2-fluoro-5 (4-(4-ethoxyphenyl)-4-methyl- 1 -pentyl)diphenyl ether (MTI 800), granulosis 62 and nuclear polyhedrosis viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217300), ivermectin, 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitro methyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan 5 3-ylcarbamaldehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron and imidacloprid. The active substance content of the use forms prepared from the commercially customary formulations can be from 0.00000001 to 95% by 10 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 15 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, 20 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 25 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 30 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 63 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. 5 The compounds of the formula I according to the invention are also distinguished by an outstanding 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 10 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 15 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 20 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. 25 Examples of fungicides which are known from the literature and which can be combined, in accordance with the invention, with the compounds of the formula I are the following products: aldimorph, andoprim, anilazine, BAS 480F, BAS 450F, BAS 490F, 30 benalaxyl, benodanil, benomyl, binapacryl, bitertanol, bromuconazole, buthiobate, captafol, captan, carbendazim, carboxin, CGA 173506, cyprodinil, cyprofuram, dichlofluanid, dichlomezin, diclobutrazol, diethofencarb, difenconazol (CGA 169374), difluconazole, dimethirimol, dimethomorph, diniconazole, dinocap, dithianon, dodemorph, dodine, 64 edifenfos, ethirimol, etridiazole, epoxiconazole, fenbuconazole, fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferimzone (TF164), fluazinam, fluobenzimine, fludioxinil, fluquinconazole, fluorimide, flusilazole, flutolanil, flutriafol, folpet, fosetyl 5 aluminum, fuberidazole, fulsulfamide (MT-F 651), furalaxyl, furconazole, furmecyclox, guazatine, hexaconazole, ICI A5504, imazalil, imibenconazole, iprobenfos, iprodione, isoprothiolane, KNF 317, copper compounds, such as Cu oxychloride, oxine-Cu, Cu oxide, mancozeb, maneb, mepanipyrim (KIF 3535), metconazol, mepronil, metalaxyl, 10 methasulfocarb, methfuroxam, MON 24000, myclobutanil, nabam, nitrothalidopropyl, nuarimol, ofurace, oxadixyl, oxycarboxin, penconazole, pencycuron, PP 969, probenazole, propineb, prochloraz, procymidon, propamocarb, propiconazole, prothiocarb, pyracarbolid, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, rabenzazole, RH7592, sulfur, 15 tebuconazole, TF 167, thiabendazole, thicyofen, thiofanatemethyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, triflumizol, triforine, trifionazol, validamycin, vinchlozolin, XRD 563, zineb, sodium dodecylsulfonate, sodium dodecyl sulfate, sodium C13/C15 alcohol ether sulfonate, sodium cetostearyl 20 phosphate ester, sodium dioctylsulfosuccinate, sodium isopropylnaphtha lenesulfonate, sodium methylenebisnaphthalenesulfonate, cetyltrimethylammonium chloride, salts of long-chain primary, secondary or tertiary amines, alkylpropyleneamines, laurylpyrimidinium bromide, ethoxylated quaternized fatty amines, alkyldimethylbenzylammonium 25 chloride and 1-hydroxyethyl-2-alkylimidazoline. The abovementioned components for combinations are known active substances of which many are described in Ch.R. Worthing, S.B. Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council. 30 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 65 use forms. The examples which follow illustrate the invention without limiting it thereto. 5 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. 10 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 15 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 20 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. 25 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. 30 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 66 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.

67 B. Preparation examples Example 1 5 H 3 C CH 3 + H CH 3 Br C1 N HN 10 N

H

3 C 0 15 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-ethyl-1 -(4-phenyl 20 phenacyl)pyrimidinium bromide 2.00 g (6.76 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-ethyl pyrimidine and 2.79 g (10.15 mmol) of bromo-4-phenylacetophenone were stirred in boiling ethanol for 18 h. The solvent was removed under reduced 25 pressure. Chromatography (silica gel; methylene chloride/methanol = 98:2) gave 1.87 g (48%) of light-yellow crystals of m.p. 126-1280C.

68 Example 2 H 3 C CH 3 + 5 CH 3 HN Br~ CI N 10

H

3 C 0 HN 15 0 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-ethyl-1 -[2-oxo-2-(2-oxo 1,2,3,4-tetrahydroquinolin-6-yl)ethyl]pyrimidinium bromide 20 1.50 g (5.07 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-ethyl pyrimidine and 1.36 g (5.07 mmol) of 6-(bromoacetyl)-2-oxo-1,2,3,4-tetra hydroquinoline were stirred in dimethylformamide at 800C for 10 h. The solvent was removed under reduced pressure (0.1 mbar). Chromatography of the residue (silica gel; ethyl acetate/methanol) gave 0.44 g (15%) of a 25 greenish solid of m.p. 122-126*C.

69 Example 3 5 HN Br~ H N N 10

H

3 C 0 O 15 0 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-ethyl-1 -(4-pivaloyl oxyphenacyl)pyrimidinium bromide 20 1.20 g (4.06 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-ethyl pyrimidine and 1.21 g (4.06 mmol) of bromo-4-pivaloyloxyacetophenone were refluxed in acetonitrile for 10 h. The solvent was removed under reduced pressure. Chromatography (silica gel; ethyl acetate/methanol) gave 1.60 g (66%) of beige-colored crystals of m.p. 1690C. 25 Preparation of the starting material bromo-4-pivaloyloxyacetophenone At 25 - 300C, 4.43 g (36.76 mmol) of pivaloyl chloride were added slowly to 5.00 g (36.76 mmol) of 4-hydroxyacetophenone, 2.91 g (36.76 mmol) of 30 pyridine and 0.45 g (3.67 mmol) of N,N-dimethylaminopyridine in 30 ml of DMF. The reaction mixture was stirred at 900C for 9 h and then poured into water. The mixture was extracted repeatedly with CH 2 Cl 2 and the organic phases were washed with 2N HCI and water and dried over Na 2

SO

4 . The solvent was removed and the residue was purified by chromatography 70 (silica gel; petroleum ether/ethyl acetate = 7:3). This gave 6.10 g of light yellow crystals which were dissolved in chloroform and treated with 1.52 ml (29.99 mmol) of bromine. The mixture was stirred at 250C for 4 h and washed two times with water, the organic phases were dried over Na 2

SO

4 5 and the solvent was removed under reduced pressure. Chromatography (silica gel; CH 2 Cl 2 ) gave 3.00 g of beige-colored crystals of m.p. 590C. The compounds of the tables below were obtained similarly to Examples 1 to 3. 10 Definition of the heterocycle radicals Het": Het' R a X CI N Rb

H

3 C Het 2 R a AXX x a N R b 71 Het 3 a x CIb

H

3 C N R Het 4 R a x H C

H

3 C O N R b Het 5 R a Br Br R b H3C 72 Het 6 ) R a Rb H 3 c Het 7 *) R N IN Rb Het 8 - N 73 Het 9 *) R x IN N R b F Het'o *) R a X H N - Rb

H

3 C Het 1 *) R a CI b

H

3 C N R 74 Het'1 2 R a

H

3 Cb

H

3 C Het 13 * R a x0 Br N

H

3 C Het 14 *) R a Br

H

3 C )N~ Rb 75 Het 15 * R a o0e

H

3 C,"l'

H

3 C N Rb Het 16 * x cI N Rb

H

3 C Het 17 * R a 0 x N Rb H 3 76 Het'1 8 Ra x N + b N Rb

H

3 0 Het 19 * Ra x N + N N Rb Het 20 * Ra x N N+.- R b

F

77 Het 2 1 *) 5 Ra x O + N

H

3 C Rb 10 It is highly probable that these heterocycle radicals have the stated constitution. However, it cannot be excluded with absolute certainty that the radical R is attached to an N* in position 3 of the pyrimidine 15 system, instead of to an N' in position 1 of this ring system. Other abbreviations used: Ph phenyl 20 Me methyl Et ethyl nPr n-propyl iPr isopropyl tBu tert-butyl Ts 4-toluylsulfonyl Definition of the radicals T: 10 1 10 Y T z= 78

X

1 0 Y10 Zbo U1 0

V'

0 T' H H H 0 -CH 3 T2 H H H 0 -CH 2

CH

3 T3 H H H 0 n-propyl T4 H H H 0 i-propyl T5 H H H 0 t-butyl

T

6 H H H 0 phenyl T H H H 0 2-pyridyl T8 H H H 0 3-pyridyl T9 H H H 0 4-pyridyl Tlo H H H 0 -CH 2 Ph T" H H H 0 -CH 2 -(4-chlorophenyl) T12 H H H 0 2-methylphenyl T13 H H H 0 2,6-dimethylphenyl T14 H H H 0 4-nitrophenyl T15 H H H 0 2,4-dichlorophenyl T16 H H H 0 4-chlorophenyl T17 H H H 0 2,6-dimethoxyphenyl T H H H 0 2,6-dichlorophenyl T19 H H H 0 2-nitrophenyl T20 H H H 0 4-methoxyphenyl T21 H H H 0 2,4-dimethoxyphenyl T22 H H H 0 cyclohexyl T23 H H H 0 4-pyrimidyl T24 H H H 0 4-(5-chloropyrimidyl)

T

25 H Cl H 0 phenyl

T

26 H Br H 0 phenyl T27 Cl Cl H 0 phenyl T28 H H H N t-butyl T29 H H H 0 -N(CH3_2 79 X10 Y10 ZlO U 10

V

10 T H H H 0 -N-piperidyl T31 H H H 0 cyclopropyl T32 H H H 0 4-t-butylphenyl T33_ . H Me H 0 phenyl T34 H H F 0 phenyl T35 Br Br H 0 phenyl T36 H NO 2 H 0 phenyl T37 H H H 0 -0-phenyl T38 H H H 0 -N(CH 3 )phenyl T39 H H H 0 -N(H)phenyl T40 H H H 0 -0-ethyl T41 H H H 0 -N(ethyl) 2 T42 H H H 0 -OCH 3 T43 H H H 0 morpholino 80 TI= 20 20 Yo x20 y20 u20 v2o T51 H H 0

-CH

3 T52 H H 0

-CH

2

CH

3 T53 H H 0 n-propyl T54 H H 0 i-propyl T55 H H 0 t-butyl T H H 0 phenyl T57 H H 0 2-pyridyl T58 H H 0 3-pyridyl T59 H H 0 4-pyridyl T60 H H 0 -CH 2 Ph T H H 0 -CH 2 -(4-chlorophenyl) T62 H H 0 2-methylphenyl T63 H H 0 2,6-dimethylphenyl T64 H H 0 4-nitrophenyl Te65 H H 0 2,4-dichlorophenyl ~ T66 H H 0 4-chlorophenyl T67 H H 0 2,6-dimethoxyphenyl T H H 0 2,6-dichlorophenyl T69 H H 0 2-nitrophenyl T H H 0 4-methoxyphenyl T H H 0 2,4-dimethoxyphenyl T72 H H 0 cyclohexyl T73 H H 0 4-pyrimidyl 81 x20 y20 u20 v20 T74 H H 0 4-(5-chloropyrimidyl) T75 H CI 0 phenyl

T

76 H Br 0 phenyl T77 CI CI 0 phenyl T78 H H N t-butyl T_ H H 0 -N(CH3)2 T__ H H 0 -N-piperidyl 82 Table 1 LHet - CH- E --- R6] 1 5 R Q No. Het" X Ra Rb E R 5

R

6 0 Physical properties 4 Het' NH tBu H C=O H Ph I 5 Het' NH tBu CH 3 C=O H (4-CI)Ph I 6 Het' NH tBu H C=O H (4-Cl)Ph Br 7 Het' NH tBu H C=O H (4-CI)Ph

NO

3 8 Het' NH tBu H C=S H (4-Ci)Ph

NO

3 9 Het 1 NH tBu H C=O H (4-OCF 3 )Ph NO 3 10 Het 2 NH Ph H C=O H (4-OCF 3 )Ph Br 11 Het 2 NH Ph CH, C=0 H (4-00F,)Ph 1 12 Het 2 NH tBu H C=S H (4-OCF 3 )Ph NO 3 13 Het 2 NH iPr H C=O H (4-OCF 3 )Ph NO 3 14 Het 3 NH Ph H C=0 H (4-OCF 3 )Ph Br 15 Het 3 NH Ph H C=O H (2-NO 2 )Ph I 16 Het 4 NH Ph H C=S H (2-NO 2 )Ph NO 3 17 Het 5 NH Ph

CH

3 C=S H (4-NO 2 )Ph NO 3 18 Het' NH Ph H C=O H (4-NO 2 )Ph Br 19 Het' NH Ph H C=O H (4-NO 2 )Ph I 20 Het' NH Ph H C=O H (2-NO 2 )Ph I 21 Het' NH Ph H C=0 H T' Br 22 Het' NH Ph H C=O H T 2 Br 23 Het' NH Ph H C=O H T 3 Br 24 Het' NH Ph H C=O H T 4 Br 25 Het' NH Ph H C=0 H T 5 Br 26 Het' NH Ph H C=O H T 6 Br m.p. >220*C 27 Het' NH Ph H C=O H T 6 1 28 Het' NH Ph H C=0 H T 7 Br 29 Het' NH Ph H C=O H T 12 Br 83 No. Het" X Ra Rb E R 5

R

6 Q Physical I I properties 30 Het' NH Ph H C=O H T1 4 Br 31 Het' NH Ph H C=O H T 1 7 Br 32 Het 1 NH Ph H C=NPh H T 4 Br 33 Het' NH Ph H C=O H T 56 Br 34 Het' NH Ph H C=O H T 55 Br 35 Het' NH Ph H C=O H T 77 Br 36 Het' NH Ph H C=S H T 6 Br 37 Het' NH Ph H C=O H T1 3 Br 38 Het 6 NH tBu H C=NPh H TS Br 39 Het 6 NH tBu H C=O H Ph Br m.p. 2160C 40 Het 6 NH tBu H C=O H (4-CI)Ph Br m.p. 2060C 41 Het6 NH tBu H C=O H (4-F)Ph Br m.p. 189*C 42 Het 6 NH tBu H C=O H (4-CH 3 )Ph Br m.p. 1820C 43 Het 6 NH tBu H C=O H (4-OCH 3 )Ph Br m.p. 132*C 44 Het 6 NH tBu H 0=0 H (2-Cl, Br m.p. 2060C I _ 4-CI)Ph 45 Het 6 NH tBu H C=O H (4-OCF 3 )Ph I 46 Het 6 NH tBu H C=O H (4-OCF 3 )Ph Br m.p. 1250C 47 Het 6 NH tBu H C=O H (4-OCF 2 H)-Ph Br m.p. 1350C 48 Het 6 NH tBu H C=O H T' Br m.p. 1460C 49 Het 6 NH tBu H C=O H T 6 I 50 Het 6 NH tBu H C=O H (4-CN)Ph Br m.p. 1730C 51 Het 6 NH tBu H C=0 H (2-NO 2 )Ph Br m.p. 1840C 52 Het 6 NH tBu H 0=0 H (3-NO 2 )Ph Br m.p. 224*C 53 Het6 NH tBu H C=O H (3-CH 3 , Br m.p. 1800C 4-CI)Ph 54 Het 6 NH tBu H 0=0 H (3-NO 2 , Br m.p. 1950C 4-CI)Ph 55 Het 6 NH tBu H C=O H (4-NO2)Ph Br m.p. 1270C 56 Het 6 NH tBu H C=O H (4-Br)Ph Br m.p. 1530C 57 Het 6 NH tBu H C=O H (4-CF 3 )Ph Br m.p. 1780C 58 Het 6 NH tBu H C=O H 1-naphthyl Br m.p. 2170C 59 Het 6 NH tBu H C=O H (3-tBu, 5-tBu, Br m.p. 154*C 4-OH)Ph 60 Het 6 NH tBu H C=O H T 2 Br m.p. 127*C 61 Het 6 NH tBu H C=O H T 4 Br m.p. 189C 84 No. Het" X Ra Rb E R 5

R

6 Q Physical I I _ properties 62 Het 6 NH tBu H C=O H T 6 Br m.p. 162 0 C 63 Het 6 NH tBu H C=O H T 10 Br 64 Het 6 NH tBu H C=0 H T 12 Br m.p. 220C 65 Het 6 NH tBu H C=0 H T 13 Br m.p. 217 0 C 66 Het 6 NH tBu H C=O H (3-Cl, BF 4 m.p. 178 0 C 4-CI)Ph 67 Het 6 NH tBu H C=0 H T 9 Br 68 Het 6 NH tBu H 0=0 H (4-OCF 3 )Ph I m.p. 180 0 C 69 Het 6 NH tBu H C=0 H (2-Cl, I m.p. 130*C 4-CI)Ph 70 Het 6 NH tBu H C=0 H (4-OH)Ph Br m.p. >220*C 71 Het 6 NH tBu H C=S H T 6 Br 72 Het 6 NH tBu H C=S H TS Br 73 Het 6 NH tBu H C=0 H T 14 Br 74 Het 7 0 tBu H C=O H T" NO 3 75 Het 8 0 tBu H C=0 H T 6 6 76 Het 9 0 tBu H 0=0 H T 6 77 Het 6 NH tBu CH 3 C=O H T 6 Br 78 Het 6 NH tBu CH 3 C=0 H T 6 Br 79 Het 6 NH tBu CH 3 C=O H T 5 Br 80 Het 6 NH tBu CH 3 C=O H T 4 Br 81 Het 6 NH tBu Cl C=O H T 5 Br 82 Het 6 NH tBu Cl C=O H T 6 Br 83 Hetl 0 NH tBu H 0=0 H T 6 Br 84 Het' NH tBu H 0=0 H T 5 Br 85 Het' NH tBu H C=O H T 16 Br 86 Het' NH tBu H C=O H T 17 Br 87 Het' NH tBu H C=O H T 18 Br 88 Het" NH tBu H C=O H T 19 Br 89 Het" NH tBu H C=O H T 12 Br 90 Het" NH tBu H C=O H T 13 Br 91 Het' NH tBu H 0=0 H T 4 Br m.p. 2090C 92 tBu H C=O H T 5 Br m.p. 222*C 93 Het tBu H 0=0 H T 6 Br m.p. 207C 85 No. Het" X Ra Rb E R 5

R

6 Q Physical properties 94 Het' NH tBu H C=O H T 7 Br 95 Het' NH tBu H C=O H Ta Br 96 Het" NH tBu H C=0 H T 3 Br 97 Het" NH tBu H C=O H (2-NO 2 )Ph Br 98 Het 1 NH tBu H 0=0 H T 20 Br 99 Het 1 1 NH tBu H C=O H T 2 1 Br 100 Het" NH tBu H C=O H T 22 Br 101 Het 12 NH tBu H C=O H - 5 Br 102 Het 6 NH tBu F C=O H T 6 Br 103 Het 13 NH tBu H C=O H T 6 Br 104 Het 14 NH tBu H 0=0 H T 4 Br 105 Het 1 4 NH tBu H C=0 H T 6 Br 106 Het 1 4 NH tBu H C=O H T 23 Br 107 Het 14 NH tBu H C=O H T 5 Br 108 Het 14 NH tBu H C=O H T 3 Br 109 Het 14 NH tBu H C=0 H T 2 4 Br 110 Het 1 5 NH tBu H C=O H Ph Br m.p. 157*C 111 Het 15 NH tBu H C=O H (4-CI)Ph Br m.p. 143 1460C 112 Het 1 5 NH tBu H 0=0 H (4-F)Ph Br m.p. 1110C 113 Het 15 NH tBu H C=0 H (4-CH 3 )Ph Br m.p. 1150C 114 Het 6 NH nPr H C=O H T 4 Br m.p. 201*C 115 Het 6 NH nPr H C=O H T 5 Br m.p. 2020C 116 Het 6 NH nPr H C=0 H T 6 Br m.p. 208 0 C 117 Het 6 NH nPr H C=O H T 12 Br 118 Het 6 NH nPr H C=O H T 13 Br 119 Het 6 NH nPr H C=O H T 25 Br 120 Het 6 NH nPr H C=O H T 26 Br 121 Het 6 NH nPr H 0=0 H T 27 Br 122 Het 6 NH nPr H 0=0 H (4-OS0 2 - Br

CF

3 )Ph 123 Het 9 0 nPr H 0=0 H T 6 Br 124 Het 6 NH nPr OH 3 C=O H T 6 Br 125 Het 6 NH nPr CH 3 0=0 H T 5 Br 126 Het" NH nPr H 0=0 H T 6 Br m.p. 2250C 86 No. Het" X Ra Rb E R 5

R

6 0 Physical I______ properties 127 Het 14 NH nPr H 0=0 H T 6 Br 128 Het 6 NH iPr H C=O H T 6 Br m.p. 2141C 129 Het 6 NH iPr H C=O H T 5 Br m.p. 1880C 130 Het 6 NH iPr H C=O H T 4 Br m.p. 2000C 131 Het 6 NH iPr H C=O H T' Br 132 Het 6 NH iPr H 0=0 H T 7 Br 133 Het 6 NH iPr H C=O H T 12 Br 134 Het 6 NH iPr H C=O H T1 3 Br 135 Het 6 NH iPr H C=O H T 14 Br 136 Het 6 NH iPr H 0=0 H T 17 Br 137 Het 6 NH iPr H 0=0 H T 18 Br 138 Het 6 NH iPr H C=O H T 29 Br 139 Het 6 NH iPr H C=O H T 30 Br 140 Het 6 NH iPr H C=O H T 28 Br 141 Het 6 NH iPr H 0=0 H T 77 Br 142 Het 6 NH iPr CH 3 0=0 H T 6 Br 143 Het" NH iPr H C=0 H T 6 Br m.p. 1980C 144 Het 14 NH iPr H C=O H T 6 Br 145 Het 14 NH iPr H 0=0 H T 5 Br 146 Het 13 NH iPr H C=O H T 12 Br 147 Het 6 NH -0(0H 3 )sF 3 H C=O H T 5 Br 148 Het 6 NH -(CH 3

)CF

3 H C=O H T 6 Br m.p. 2020C 149 Het 6 NH -C(CH 3

)CF

3 H C=O H T 4 Br 150 Het 6 NH -C(CH 3

)CF

3 H C=O H T 56 Br 151 Het' NH -C(CH 3

)CF

3 H C=O H T 55 Br 152 Het 6 NH -C(CH 3

)CF

3

CH

3 0=0 H T 54 Br 153 Het 6 NH -C(CH 3

)CF

3

CH

3 C=O H T 6 Br 154 Het 1 4 NH -C(0H 3 )0F 3 H 0=0 H T 6 Br 155 Hat 6 NH -C(CH 3

)CF

3 CI 0=0 H T 6 Br 156 Het 6 NH SiMe 3 H 0=0 H T 4 Br 157 Het 6 NH SiMe 3 H 0=0 H T 5 Br m.p. 2030C 158 Het 6 NH SiMe 3 H C=O H T 6 Br m.p. 1350C 159 Het 6 NH SiMe 3 H C=O H T 12 Br 160 Het 6 NH SiMe 3

CH

3 C=O H T 6 Br 161 Het NH SiMe 3 H C=0 H T 13 Br 87 No. Het" X Ra Rb E R 5

R

6 0 Physical I _properties 162 Het 13 NH SiMe 3 H C=O H T 6 Br m.p. 184 0 C 163 Het 10 NH SiMe 3 H C=O H T 4 Br 164 Het 10 NH SiMe 3 H C=O H T 5 Br m.p. 2700C 165 Hetl 0 NH SiMe 3 H C=0 H T6 Br m.p. 267*C 166 Het1 5 NH tBu H C=O H (4-OCH 3 )Ph Br m.p. 160*C 167 Het 6 NH Ph H C=O H (4-Cl)Ph Br m.p. 2250C 168 Het 6 NH Ph H C=O H (4-F)Ph Br m.p. 2420C 169 Het 6 NH Ph H 0=0 H (4-OCH 3 )Ph Br m.p. 212*C 170 Het 6 NH Ph H C=O H T' Br m.p. 2150C 171 Het 6 NH Ph H 0=0 H (4-OCF 3 )Ph Br m.p. 2150C 172 Het 6 NH Ph H C=O H (3-Cl, Br m.p. 2220C 4-CI)Ph 173 Het6 NH Ph H C=O H (4-0H 3 )Ph Br m.p. 2070C 174 Het 6 NH Ph H C=O H (4-CN)Ph Br m.p. 210*C 175 Het 6 NH Ph H C=O H (4-NO 2 )Ph Br m.p. 2160C 176 Het 6 NH Ph H C=O H (4-Br)Ph Br m.p. >210*C 177 Het 6 NH Ph H C=O H (4-CF 3 )Ph Br m.p. 1940C 178 Het 6 NH Ph H C=O H (3-NO 2 )Ph Br m.p. 242*C 179 Het 6 NH Ph H C=O H (3-NO 2 , Br m.p. 2280C I_ 4-Cl)Ph 180 Het 6 NH Ph H C=O H (2-NO 2 )Ph Br m.p. 152*C 181 Het 6 NH Ph H 0=0 H (3-tBu, 5-tBu, Br m.p. 161*C 4-OH)Ph 182 Het 6 NH Ph H 0=0 H T 6 Br m.p. 2020C 183 Het 6 NH Ph H C=O H T 4 Br m.p. 205*C 184 Het 6 NH Ph H C=O H T 5 Br m.p. 2050C 185 Het 6 NH Ph H C=O H 4-(OCF 3 )Ph BF 4 m.p. 1410C 186 Het 6 NH Ph H C=O H T 12 Br m.p. 2070C 187 Het 6 NH Ph H C=O H T1 3 Br m.p. 218*C 188 Het 6 NH Ph H C=O H T 10 Br m.p. 218*C 189 Het 6 NH Ph H C=O H T 14 Br m.p. 208*C 190 Het 6 NH Ph H C=0 H T' 9 Br m.p. 1520C 191 Het 6 NH Ph H 0=0 H T 20 Br 192 Het 6 NH Ph H C=O H T1 7 Br 193 Het 6 NH Ph H 0=0 H T 54 Br 88 No. Het" X Ra Rb E R 5

R

6 Q Physical properties 194 Het 6 NH Ph H C=0 H T 55 Br 195 HetI NH Ph H C=O H T1 6 Br m.p. 199*C 196 Het 6 NH Ph H C=O H T 62 Br 197 Het 6 NH Ph H C=O H T 63 Br 198 Het 6 NH Ph H C=0 H T 60 Br 199 Het 6 NH Ph H 0=0 H T 64 Br 200 Het 6 NH Ph H C=O H T 67 Br 201 Het 7 NH Ph H 0=0 H T 6 Br 202 Het 8 0 Ph H C=O H T 6 Br 203 Het 9 NH Ph H C=O H T 6 Br 204 Het 6 NH Ph H 0=0 H T 69 Br 205 Het 6 NH Ph CH 3 C=0 H - 6 Br 206 Het 6 NH Ph CH 3 C=O H T 5 Br 207 Het 6 NH Ph CH 3 C=O H T 4 Br 208 Het 6 NH Ph H C=0 H T 70 Br 209 Het 6 NH Ph H 0=0 H T 71 Br 210 Het 6 NH Ph H C=O H T 72 Br 211 Het 6 NH Ph H C=O H T 27 Br m.p.231 0 0 212 Het 6 NH Ph C1 C=O H T 4 Br 213 Het 6 NH Ph C C=O H T 5 Br 214 Het 6 NH Ph Ci C=O H T 6 Br 215 Het 6 NH Ph Cl C=O H T 13 Br 216 Het 1 I NH Ph H C=O H T 5 Br 217 Hetl 0 NH Ph H C=O H T 6 Br 218 Het" NH Ph H C=O H T 4 Br m.p. 2220C 219 Het" NH Ph H C=O H T 5 Br m.p. 2080C 220 Het 1 1 NH Ph H C=O H T 6 Br m.p. 2130C 221 Het' 1 NH Ph H C=0 H T 12 Br 222 Het 12 NH Ph H C=O H T 6 Br 223 Het 6 NH Ph F 0=0 H T 6 Br 224 Het 13 NH Ph H C=0 H T 6 Br 225 Het 14 NH Ph H 0=0 H T 4 Br 226 Het 14 NH Ph H C=O H T 5 Br 227 Het 14 NH Ph H 0=0 H T 6 Br 228 Het 14 NH Ph H C=O H T1 2 Br 89 No. Het" X Ra Rb E R 5

R

6 Q Physical I I properties 229 Het 14 NH Ph H C=O H T 56 Br 230 Het 15 NH Ph H C=O H (4-CI)Ph Br m.p. 1520C 231 Het 15 NH Ph H C=O H (3-Cl, Br m.p. 183 0 C I_ _ _4-CI)Ph 232 Het 1 5 NH Ph H C=O H (4-OCF 3 )Ph Br m.p. 175*C 233 Het 15 NH Ph H C=O H T 5 Br 234 Het 15 NH Ph H C=0 H T 6 Br m.p. 169*C 235 Het 15 NH tBu H C=O H (3-Cl, Br m.p. 1490C I _4-CI)Ph 236 Het 15 NH tBu H C=O H (4-OCF 3 )Ph Br m.p. 146*C 237 Het 15 NH tBu H C=O H (4-Cl, Br m.p. 1450C 3-CH 3 )Ph 238 Het 15 NH tBu H C=O H T 5 Br m.p. 1150C 239 Het 15 NH tBu H C=O H T 6 Br m.p. 1220C 240 Het 6 NH -C(CH 3

)

2 H C=O H T 6 Br

CH

2 tBu 241 Het 6 NH -C(CH 3

)

2 H C=O H T 4 Br

CH

2 tBu I 242 Het 6 NH -C(CH 3

)

2 H C=O H T 5 Br

CH

2 tBu 243 Het 6 NH -C(CH 3

)

2 H C=O H T 6 Br

CH

2 tBu 244 Het 6 NH -C(CH 3

)

2 H C=O H T 5 6 Br CH 2 tBu 245 Het 6 0 -C(CH 3

)

2 H C=O H T 6 Br

CH

2 tBu 246 Het 7 0 -C(CH 3

)

2 H C=O H T 5 Br CH2 tBu 247 Het 7 0 -C(CH 3

)

2 H C=O H T 6 Br

CH

2 tBu 248 Het 8 0 -C(CH 3

)

2 H C=O H T 6 Br

CH

2 tBu 249 Het 9 0 -C(CH 3

)

2 H C=O H T 6 Br

CH

2 tBu 250 Het 15 0 -C(CH 3

)

2 H C=O H T 6 Br

CH

2 tBu 251 Het 15 NH -C(CH 3

)

2 H C=O H T 6 Br

CH

2 tBu 90 No. Het" X Ra Rb E R 5

R

6 0 Physical I properties 252 Het1 3 NH -C(CH 3

)

2 H C=O H T, Br

CH

2 tBu 253 Het 3 NH -C(CH 3

)

2 H C=O H T 6 Br CH 2 tBu 254 Het 6 NH 4-trifluoro- H C=O H T 6 Br methylphenyl 255 Het 6 NH 4-trifluoro- H C=O H T 56 Br methylphenyl 256 Het' NH 4-trifluoro- H C=O H T 6 Br methylphenyl 257 Het 13 NH 4-trifluoro- H C=O H T 6 Br methylphenyl 258 Het 6 NH 4-fluorophenyl H C=O H T 6 Br 259 Het 13 NH 4-methylphenyl H C=0 H T 6 Br 260 Het 6 NH 4-methylphenyl H C=O H T 6 Br m.p. 207*C 261 Het 15 NH 4-methylphenyl H C=O H T 6 Br 262 Het 6 NH 4-methylphenyl H C=0 H T 5 Br 263 Het 6 NH 4-isopropyl- H C=O H T 6 Br oxyphenyl 264 Het 6 NH 4-isopropyl- H C=O H T, Br oxyphenyl 265 Het 6 NH 4-isopropyl- H C=0 H T 4 Br oxyphenyl 266 Het 6 NH 4-isopropyl- H C=O H (2-NO 2 )Ph Br oxyphenyl 267 Het 6 NH 4-isopropyl- H C=O H T 56 Br oxyphenyl 268 Het 13 NH 4-isopropyl- H C=O H T 77 Br oxyphenyl 269 Het 7 NH 4-isopropyl- H C=O H T 6 Br oxyphenyl 270 Het 1 5 0 4-isopropyl- H C=O H T 6 Br oxyphenyl 271 Het 6 NH 4-ethoxyphenyl H C=O H T 6 Br 272 Het 6 NH 4-ethoxyphenyl H C=O H T1 3 Br 273 Het 6 NH 4-ethoxyphenyl H C=O H T 5 Br 274 Het 15 NH 4-ethoxyphenyl H C=O H T 14 Br 91 No. Het" X Ra Rb E R 5

R

6 0 Physical properties 275 Het 1 5 0 4-ethoxyphenyl H C=O H T 6 Br 276 Het 15 NH tBu H C=O H (3-tBu, 5-tBu, Br m.p. 153*C _ _4-OH)Ph 277 Het 6 NH -C(CH 3

)

2 0H H C=O H T 6 Br 278 Het 15 NH tBu H C=O H (4-CF 3 )Ph Br m.p. 1550C 279 Het 6 NH -CH 2 0CH 2 - H C=O H T 6 Br m.p. 2080C

CH

3 280 Het 6 NH -CH 2 0CH 3 H C=O H T 6 Br 281 Het 6 NH -CH 2

OCH

2 - H C=O H T 5 Br

CH

3 282 Het 15 NH -CH 2 0CH 2 - H C=O H T 6 Br

CH

3 283 Het 15 NH tBu H C=O H (4-NO 2 )Ph Br m.p. 1040C 284 Het 1 5 NH tBu H C=O H (4-Cl, Br m p. 1130C 3-NO 2 )Ph 285 Het 6 NH -COOtBu H C=O H T 6 Br 286 Het 6 NH -CON(CH 3 )Ph H C=O H T 6 Br 287 Het 1 5 NH -CON(CH 3 )Ph H C=O H T 6 Br 288 Het 13 NH -CON(CH 3 )Ph H C=O H T 6 Br 289 Het 9 NH -CON(CH 3 )Ph H C=O H T 6 Br 290 Het 6 NH Ph H C=0 CH 3

T

6 Br 291 Het 6 NH tBu H C=O CH 3 Ph Br m.p. 1300C 292 Het 6 NH Ph H C=O CH 2 Ph Br

CH

3 293 Het 6 NH tBu H C=O -CH 3 4-(OCH 2 Ph)- Br 'H-NMR Ph (CDC1 3 ): 6= 0.95 (s,9H), 5.1 (s,2H), 6.8 (d, NH), 7.6 (q,1H) 294 Het 6 NH tBu H C=0 H T 19 Br m.p. 2080C 295 Het 6 NH tBu H C=O H T 17 Br 296 Het 6 NH Ph H C=O H T 51 Br 297 Het 6 NH Ph H C=O H T 5 2 Br 298 Het' NH Ph H C=O H T 53 Br 299 Het' NH Ph H C=O H T 5 Br 300 Het 6 NH Ph H C=O -CH 3

T

6 Br 92 No. Het" X Ra Rb E R 5

R

6 Q Physical I properties 301 Het 16 NH tBu H C=O H T 5 Br 302 Het 16 NH tBu CH 3 C=O H T 6 Br 303 Het 16 NH tBu H C=O H T 6 Br m.p. 211*C 304 Het 16 NH 4-fluorophenyl H C=O H T 5 Br 305 Het 16 NH 4-fluorophenyl H C=O H T 4 Br 306 Het 16 NH 4-fluorophenyl H C=0 H T 6 Br 307 Het' 6 NH 4-fluorophenyl H C=O H T 12 Br 308 Het 16 NH Ph H C=O -CH 3

T

6 Br 309 Het 16 NH Ph H C=O H T 6 Br m.p. 1940C 310 Het 16 NH Ph H C=O H T 5 Br 311 Het 16 NH Ph H C=O H T 4 Br 312 Het 16 NH Ph H C=O H T" Br 313 Het 16 NH 2-thienyl H C=O H T 4 Br 314 Het 16 NH 2-thienyl H C=O H T 5 Br 315 Het 16 NH 2-thienyl H C=O H T 6 Br 316 Het 18 NH -OCH 2

CH

3 H C=O H T 6 Br 317 Het 1 8 NH -OSO 2

CH

3 H C=O H T 4 Br 318 Het 18 NH -OS02CH 3 H C=O H T 5 Br 319 Het 1 8 NH -OS02CH 3 H C=O H T 6 Br 320 Het 1 8 NH -OC(O)- H C=0 H T 6 Br

N(CH

3

)

2 321 Het 18 NH -OCH 2

CH

3 H C=O H T 5 Br 322 Het 18 NH -OS02CF 3 H C=O H T 6 Br 323 Het 18 NH -OC(0)- F C=O H T 5 Br

N(CH

3

)

2 324 Het 18 0 -OCH 2

CH

3 H C=O H T 6 Br 325 Het 1 8 NH -OCH 2

CH

3 H C=O H T 4 Br 326 Het 18 NH -OS02CF 3 H C=O H T 5 Br 327 Het 18 NH -OS02CF 3 H C=O H T 4 Br 328 Het 18 NH -OCH 2

CH

3 H C=O H T1 2 Br 329 Het 18 NH -OCH 2

CH

3 H C=0 H T1 3 Br 330 Het 18 NH -OC(O)- H C=O H T 4 Br

N(CH

3

)

2 93 No. Het" X Ra Rb E R 5

R

6 Q Physical I I_ properties 331 Het 1 7 NH nPr H C=0 H T 4 Br 332 Het 17 NH nPr H C=0 H T 5 Br 333 Het 17 NH nPr H C=O H T 6 Br 334 Het 17 NH nPr H C=O H T" Br 335 Het 17 NH nPr H C=O H T1 2 Br 336 Het 17 NH nPr H C=O CH 3

T

8 Br 337 Het 17 NH nPr H C=O H T 9 Br 338 Het 17 NH Ph H C=O H T 4 Br 339 Het1 7 NH Ph H C=O H T 5 Br m.p. 77 83*C 340 Het1 NH Ph H C=O H T 6 Br m.p. 680C 341 Het 17 NH Ph H C=O H T 54 Br 342 Het 17 NH Ph H C=O H T 55 Br 343 Het 17 NH Ph H C=O H T 56 Br 344 Het 17 NH Ph H C=0 H T 7 7 Br 345 Het 17 NH tBu H C=0 H T 5 Br 346 Het 17 NH tBu H C=O H T 6 Br 347 Het 19 0 -OCH 2

CH

3 H C=O H T 5 Br 348 Het 19 0 -OCH 2

CH

3 H C=O H T 6 Br 349 Het 19 0 -OCH 2

CH

3 H C=O H T 55 Br 350 Het 19 0 -OCH 2

CH

3 H C=O H T 56 Br 351 Het 19 0 -OCH 2 Ph H C=0 H T 6 Br 352 Het 19 0 -O(CH2) 2 H C=0 H T 6 Br

OCH

3 353 Het 1 9 0 -OCH 2 Ph H C=O H T 5 Br 354 Het 20 0 -OCH 2 Ph H C=0 H T 4 Br 355 Het 20 0 -OCH 2 Ph H C=O H T 5 Br 356 Het 20 0 -OCH 2 Ph H C=O H T 6 Br 357 Het 19 0 -OCH 2 Ph H C=O H T 55 Br 358 Het 19 0 -OS02CH 3 H C=O H T 6 Br 359 Het 1 9 0 -OS02CF 3 H C=O H T 5 Br 360 Het 19 0 -OCH 2

CH

3 H C=O H T1 2 Br 361 Het 19 0 -OCH 2

CH

3 H C=O H T1 3 Br 94 No. Het' X Ra Rb E R 5

R

6 0 Physical I properties 362 Het' 9 0 -O(CH 2

)

2 H C=O H T 56 Br

OCH

3 363 Het 1 9 0 -O(CH 2

)

2 H C=O H T 5 Br

OCH

3 364 Het 20 0 -O(CH 2

)

2 H C=O H T5 Br

OCH

3 365 Het 20 0 -O(CH 2

)

2 H C=O H T 6 Br

OCH

3 366 Het 20 0 -OCH 2

CH

3 H C=O H T 6 Br 367 Het 20 0 -OCH 2

CH

3 H C=O H T 66 Br 368 Het 20 0 -OS0 2

CH

3 H C=O H T 6 Br 369 Het 2 o 0 -OS0 2

CH

3 H C=O H T 5 Br 370 Het 20 0 -OS02CF 3 H C=O H T 6 Br 371 Het 6 NH =NOtBu H C=O H T 4 Br 372 Het 6 NH =NOtBu H C=O H T 5 Br 373 Het 6 NH =NOCH 2

CH

3 H C=O H T 6 Br 374 Het 15 NH =NOtBu H C=0 H T 6 Br 375 Het 6 NH =NOCH 2 Ph H C=O H T 6 Br 376 Het 6 NH -O(CH 2

)

2 0- H C=O H T 6 Br 377 Het 8 NH -OCH 2 CH H C=O H T 5 Br (tBu)O 378 Het 6 NH -OCH 2 CH H C=O H T 6 Br (tBu)O 379 Het 13 NH -OCH 2 CH H C=O H T 6 Br (tBu)O 380 Het 6 NH -OCH 2 CH H C=O H T 4 Br (tBu)O 381 Het 6 NH -OCH 2 CH H C=O H T 4 Br (Ph)O 382 Het 6 NH -OCH 2 CH H C=0 H T 5 Br (Ph)O 383 Het 6 NH -OCH 2 CH H C=O H T 6 Br (Ph)O 384 Het 6 NH -OCH 2 CH H C=0 H T1 9 Br (Ph)O- 95 No. Hetn X Ra Rb E R 5

R

6 0 Physical I _properties 385 Het 6 NH -OCH 2 CH H C=O H T 20 Br (Ph)O 386 Het 15 NH -OCH 2 CH H C=O H T 6 Br (Ph)O 387 Het 6 NH Ph H C=O H T 57 Br 388 Het 6 NH Ph H C=O H T 58 Br 389 Het 6 NH Ph H C=O H T 5 9 Br 390 Het 6 NH Ph H C=O H T 61 Br 391 Het 6 NH Ph H C=O H T 65 Br 392 Het 6 NH Ph H C=O H T 66 Br 393 Het 6 NH Ph H C=O H T 68 Br 394 Het 6 NH Ph H C=O H T 73 Br 395 Het 6 NH Ph H C=O H T 74 Br 396 Het 6 NH Ph H C=O H T 75 Br 397 Het 6 NH Ph H C=O H T 76 Br 398 Het 6 NH Ph H C=O H T 7 Br 399 Het 6 NH Ph H C=O H T 78 Br 400 Het 6 NH Ph H C=O H T 79 Br 401 Het 6 NH Ph H C=0 H T 80 Br 402 Het 6 NH tBu H C=O H T 8 Br 403 Het 6 NH tBu H C=O H T1 5 Br 404 Het 6 NH tBu H C=O H T 16 Br m.p. 1700C 405 Het 6 NH tBu H C=0 H T 18 Br m.p. 2040C 406 Het 6 NH tBu H C=O H T 20 Br 407 Het 6 NH tBu H C=O H T 22 Br 408 Het 6 NH tBu H C=O H T 27 Br m.p. 207*C 409 Het 6 NH tBu H C=O H T 5 4 Br 410 Het 6 NH tBu H C=O H T 55 Br 411 Het 6 NH tBu H C=0 H T 56 Br m.p. 1890C 412 Het 6 NH tBu H C=O H T 75 Br 413 Het 6 NH tBu H C=O H T 76 Br 414 Het 6 NH tBu H C=O H T 62 Br 415 Het 6 NH tBu H C=O H T 63 Br 96 No. Hetn X Ra Rb E R 5

R

6 Q Physical 41 6Iete N Hu_ C =OT_ pro p erties 416 Het 6 NH tBu H C=O H T 69 Br 417 Het 6 NH tBu H C=0 H T 7 0 Br 418 Het 6 NH Ph H C=O H T 16 Br m.p. 175*C 419 Het 6 NH tBu H C=O H T1 4 Br m.p. 1780C 420 Het 6 NH Ph H C=O H Ph Br m.p. 208 0 C 421 Het 13 NH nPr H C=O H T 6 Br m.p. 206*C 422 Het 13 NH nPr H C=O H T 5 Br m.p. 193 196*C 423 Het 6 NH Ph H C=O H T1 8 Br m.p. 207*C 424 Het 6 NH tBu H C=O H (H-OCF 3 )Ph BF 4 m.p. 128*C 425 Het 6 NH -C(CH 3

)

2 Et H C=O H T 5 Br m.p. 208*C 426 Het 6 NH -C(CH 3

)

2 Et H C=O H T 4 Br m.p. 1870C 427 Het 6 NH -C(CH 3

)

2 Et H C=O H T 6 Br m.p. 186*C 428 Het 13 NH -C(CH 3

)

2 Et H C=O H TS Br m.p. 1790C 429 Het 13 NH iPr H C=O H T 5 Br m.p. 198*C 430 Het1 3 NH iPr H C=O H T 6 Br m.p. 2190C 431 Het 13 NH -C(CH 3

)

2 Et H C=O H T 6 Br m.p. 1620C 432 Het 13 NH nPr H C=O H T 4 Br m.p. 190*C 433 Het 6 NH tBu H C=O H T 31 Br m.p. 172*C 434 Het 6 NH Ph H C=O H T 31 Br m.p. 2080C 435 Het 6 NH Ph H C=O H T 6

BF

4 m.p. 2020C 436 Het 6 NH Ph H C=O H (4-OH)Ph Br m.p. >220*C 437 Het 13 NH iPr H C=O H T 4 Br m.p. 191*C 438 Het 15 NH iPr H C=O H T 6 Br m.p. 140*C 439 Het 1 5 NH iPr H C=O H T 5 Br m.p. 1700C 440 Het1 5 NH nPr H C=O H T 5 Br m.p. 1720C 441 Het 15 NH nPr H C=O H T 6 Br m.p. 1530C 442 Het1 5 NH nPr H C=O H T 4 Br m.p. 1610C 443 Het 15 NH SiMe 3 H C=O H T 6 Br m.p. 1390C 444 Het 21 NH SiMe 3 H 0=0 H T 6 Br m.p. 2740C 97 No. Het" X Ra Rb E R 5

R

6 Q Physical I_ I properties 445 Het" NH -C(CH 3

)

2 Et H C=O H T 6 Br m.p. 195 0 C 446 Het 1 NH -C(CH 3

)

2 Et H C=O H T, Br m.p. 218 0 C 447 Het" NH nPr H C=O H T 5 Br m.p. 219*C 448 Het 1 NH iPr H C=O H T 5 Br m.p. 219 0 C 449 Heti 1 NH SiMe 3 H C=O H T 6 Br m.p. 218 0 C 450 Het 13 NH SiMe 3 H C=O H T 5 Br m.p. 207*C 451 Het 21 NH SiMe 3 H C=O H T 5 Br m.p. 2730C 452 Het' 1 NH SiMe 3 H C=O H T 5 Br m.p. 22200 453 Het 6 NH -CH 2

CH

2

CF

3 H C=O H T 6 Br m.p. 2040C 454 Het 6 NH Ph H C=O H T 32 Br m.p. 2180C 455 Het 6 NH tBu H C=0 H T 32 Br m.p. 186 188*C 456 Het 6 NH Ph H C=0 H T 33 Br m.p. 208 210*C 457 Het 6 NH tBu H C=O H T 33 Br m.p. 158 1610C 458 Het 6 NH tBu H C=O H [3-OC(O)Ph] Br m.p. 2030C Ph 459 Het 6 NH Ph H C=O H [3-OC(O)Ph] Br m.p. 2050C Ph 460 Het 6 NH Ph H C=O H T 34 Br m.p. 205 207*C 461 Het 6 NH tBu H C=O H T 34 Br m.p. 1970C 462 Het 6 NH Ph H C=O H T 35 Br 'H-NMR (CDC1 3 ): 6 = 1.22 (t, 3H), 6.8 (d, NH), 7.08 (s, 2H), 8.62 (s, 2H), 9.65 (s, 1 H) 463 Het 6 NH tBu H C=O H T 35 Br m.p. >2200C 464 Het 6 NH Ph H C=O H T 36 Br m.p. 189*C 465 Het 6 NH tBu H C=O H T 36 Br m.p. 209 2110C 466 Het 6 NH Ph H C=0 H T 37 Br m.p. 2080C 467 Het 6 NH tBu H C=O H T 37 Br m.p. 206*C 98 No. Het" X Ra Rb E R 5

R

6 Q Physical I I properties 468 Het 6 NH tBu H C=O H T 29 Br m.p. 158 160*C 469 Het 6 NH Ph H C=O H T 29 Br m.p. 201 2030C 470 Het 6 NH Ph H C=0 H (4-OCF 2 H) Br m.p. 190 Ph 1920C 471 Het 6 NH Ph H C=O H (4-OCFCI- Br 211*C

CF

2 Cl)Ph 472 Het 6 NH tBu H C=0 H (4-OCFCI- Br m.p. >

CF

2 CI)Ph 2200C 473 Het 6 NH tBu H C=O H [4-OCF 2 - Br m.p. 1730C

CFHO-(CF

2

)

2 CF 2 H]Ph 474 Het 6 NH Ph H C=O H [4-OCF 2 -CFH- Br m.p. > O-(CF2)2- 210*C

CF

2 H]Ph 475 Het 6 NH Ph H C=O H T 38 Br m.p. >2200C 476 Het 6 NH tBu H C=0 H T 38 Br m.p. 188 191*C 477 Het 6 NH tBu H C=O H T 39 Br m.p. >210"C 478 Het 6 NH Ph H C=O H T 39 Br m.p. >210*C 479 Het 6 NH Ph H C=O H (4-OS0 2 Br m.p. 2000C

CH

3 )Ph 480 Het 6 NH tBu H C=O H (4-OS0 2 Br m.p. 2160C

CH

3 )Ph 481 Het 6 NH Ph H C=0 H T 40 Br m.p. 2030C 482 Het 6 NH tBu H C=0 H T 40 Br m.p. 143 1450C 483 Het 15 NH -CH=NOEt H C=O H T 6 Br m.p. 152 1560C 484 Het 6 NH Ph H C=O H T 41 Br > 2050C 485 Het 6 NH Ph H C=O H T 43 Br m.p. 2170C 486 Het 6 NH tBu H C=O H T 43 Br m.p. 2080C 99 No. Het" X Ra Rb E R 5

R

6 Q Physical properties 487 Hete NH tBu H C=O H T 42 Br m.p. 158 1620C 488 Het 6 NH Ph H C=O H T 42 Br m.p. 193 195 0 C 489 Het 6 NH Ph H C=O H (4-OS0 2 Br m.p.

CF

3 )Ph >215*C 490 Het 6 NH tBu H C=O H (4-OS0 2 Br m.p. 201*C

CF

3 )Ph 491 Het 6 NH tBu H C=O H (3-Cl, Br m.p. 4-OS0 2 >210*C

CF

3 )Ph 492 Het 6 NH Ph H C=0 H (3-Cl, Br m.p. 4-OSO 2

CF

3 ) >212*C Ph 493 Het 6 NH Ph H C=O H (4-OTs)Ph Br m.p. 2110C 494 Het 6 NH tBu H C=O H (4-OTs)Ph Br m.p. 1780C 495 Het 6 NH Ph H C=O H Br m.p. 206 0 C a 496 Het 6 NH tBu H C=0 H a Br m.p. 2030C 497 Het 6 NH tBu H C=O H (2-OMe, Br m.p. 188*C 5-OMe)Ph 498 Het 6 NH Ph H C=O H (2-OMe, Br m.p. 1940C 5-OMe)Ph 499 Het 6 NH Ph H C=O H (2-OMe, Br m.p. 182 4-OMe)Ph 184*C 500 Het 6 NH tBu H C=O H (2-OMe, Br m.p. 168 4-OMe)Ph 1700 501 Het 6 NH tBu H C=O H (2-OMe, Br m.p. 1510C 4-Br)Ph 502 Hets NH Ph H C=O H (2-OMe, Br m.p. 4-Br)Ph >205*C 100 No. Het" X Ra Rb E R 5

R

6 Q Physical properties 503 Het 6 NH Ph H C=O H (2-OEt, Br m.p. 194*C 4-Br)Ph 504 Het 6 NH tBu H C=O H (2-OEt, Br m.p. 132 0 C 4-Br)Ph 505 Het 13 NH SiMe 3 H C=O H T 4 Br m.p. 91 96 0 C 506 Het 6 NH CH 2 O(4-F-Ph) H C=O H T 4 Br m.p. 210*C 507 Het 6 NH CH 2 0(4-F-Ph) H C=O H T 6 Br m.p. 2290C 508 Het 13 NH C 2

H

4

CF

3 H C=0 H T 6 Br m.p. 2140C 509 Het 6 NH CHCF 3 0Et H C=O H T 6 Br m.p. 2390C 510 Het1 3 NH CHCF 3 0Me H C=O H T 6 Br m.p. 237*C 511 Het 6 NH CHNOEt H C=O H T 4 Br m.p. 1990C 512 Het 6 NH CHNOEt H C=O H T 5 Br m.p. 215*C 513 Het 6 NH CHNOEt H C=O H T 6 Br m.p. 181 1830C 514 Het 6 NH C 2

H

4

CF

3 H C=0 H T 4 Br m.p. 217 218*C 515 Het 6 NH C 2

H

4

CF

3 H C=O H T 5 Br m.p. 2190C 516 Het 6 NH CMeCF 3 0Me H C=O H T 6 Br 517 Het 13 NH CMeCF 3 0Me H C=O H T 6 Br C. Biological examples Use as insecticide/acaricide/nematicide 5 Example 1 Rice seed is germinated on moist cotton in cultivation glasses. After the plants have grown to a stem length of approximately 8 cm, the leaves are sprayed to run-off point with an aqueous solution of the formulated preparation to be examined. After the solution has run off, the rice plants 10 treated in this manner are placed in cultivation containers and populated with in each case 10 larvae (L3 stage) of the rice leafhopper species Nilaparvata lugens. After the solution has run off, plants and animals are kept in a climatized chamber (16 hours of light/day, 25*C, 40 - 60% relative 101 atmospheric humidity). At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples No. 39 and 40 show an activity resulting in 90 - 100% mortality of the test species used. 5 Example 2 1 ml of an aqueous solution of the formulated preparation to be examined is pipetted onto a filter disk. After the solution has run off, this filter is placed in a Petri dish and populated with 10 L2 larvae of the southern corn rootworm (Diabrotica undecimpunctata). After being kept for 2 days in a 10 climatized chamber at 260C, the mortality is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 39, 40 and 110 show an activity resulting in 90 - 100% mortality of the test species used. 15 Example 3 Germinated field bean seeds (Vicia faba) 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 sprayed to run-off point with an aqueous solution of the formulated 20 preparation to be examined. After the solution has run off, plants and animals are stored in a climatized chamber (16 hours of light/day, 250C, 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), the preparation of 25 Example No. 39 causes a 90 - 100% mortality of the aphids. Example 4 Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into brown bottles filled with tap water and subsequently 30 populated with approximately 100 spider mites (Tetranychus urticae). The plant leaf and the spider mites are sprayed to run-off point with an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a climatized chamber (16 hours of light/day, 250C, 40 - 60% relative atmospheric humidity). After 102 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), the preparations of Examples Nos 39 and 40 cause a mortality of 90 - 100%. 5 Example 5 Part A of the test (contact activity): Approximately 5000 recently hatched, active (mobile) larvae (2nd development stage) of the root gall nematode (Meloidogyne incognita) are placed into a glass vessel containing an 10 aqueous solution of the formulated preparation to be examined. After the nematode larvae have been permanently exposed for 2 days, the percentage of the specimen which had ceased to move (been immobilized) owing to the effect of the preparation is determined by comparison with the untreated controls (percent nematicidal contact activity). 15 Part B of the test (soil-drench activity): For this test, the entire solution from part A of the test (active compound and pre-treated nematode larvae) is poured into a pot filled with soil in which three 9-day-old cucumber plants (Cucumis sativus) have been planted. This drench application reduces the 20 active compound content, based on the volume of the soil, to one third of the active compound content in part A of the test. After two weeks in a greenhouse at about 26 0 C (the plants being watered twice a day), the root balls of the cucumber plants are carefully washed out from the soil mixture infested with nematodes. The number of root galls per plant is counted and 25 compared with the infestation of untreated control plants. The reduction of infestation in percent as activity criterion is calculated using Abbott's formula (percent nematicidal soil-drench activity). At a concentration of 3 ppm in part A of the test and 1 ppm in part B of the 30 test, respectively, (based in each case on the content of active compound), the preparations of Examples Nos 40 and 110 have a 90 - 100% activity against the root gall nematode Meloidogyne incognita. Example 6 103 A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Ten L2 larvae of the Egyptian cotton leaf worm (Spodoptera litoralis) are counted into a small beaker. 200 pl of an aqueous solution of the formulated preparation to be 5 examined are pipetted into the beaker. The treated larvae are then poured into the Petri dish and a further 200 pl of the aqueous solution are spread over the culture medium. The Petri dish is sealed and then stored at about 250C in a climatized chamber. After 6 days storage, the effect of the preparation on the larvae is determined. At a concentration of 300 ppm 10 (based on the content of active compound), the preparations of Examples Nos 43, 1, 111, 167, 169, 170, 171, 230, 172, 231, 181, 182, 188, 435, 454, 260, 462, 471 and 184 effect a mortality of 90 - 100% among the larvae. 15 Example 7 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 buttworm (Heliothis virescens) are dipped into an aqueous solution of the formulated preparation to be 20 examined for about 5 seconds and subsequently placed into the Petri dish. A further 200 pl of the aqueous solution are spread over the culture medium. The Petri dish is sealed and then kept at about 25*C in a climatized chamber. After 6 days storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is 25 determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 41, 42, 111, 167, 169, 230, 235, 172,173,50,55,237,174,175,176,177,180,181,60,61,62, 182, 183,184, 238, 239, 185, 69,2,278, 283, 284, 404, 418, 419,189, 188, 421,115,422,420,26,423,190,294,405,424,425,426,427,428, 129, 30 431, 148, 65, 433, 434, 435, 436, 64,186,187,220,218,219,158,162, 157, 450, 453, 454, 260, 456, 457, 459, 460, 461, 408, 411, 464, 466, 467, 468, 469, 470, 279, 471,472,473,474,475,476,478,479,480,481,482, 340 and 68 effect a mortality of 90 - 100%.

104 Example 8 Germinated field bean seeds (Vicia faba) 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 5 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 climatized chamber (16 hours of light/day, 250C, 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 10 300 ppm (based on the content of active compound), the preparations of Examples Nos 41, 42, 44, 46, 47, 293, 167, 171, 172, 173, 50, 52, 51, 54, 55, 56, 57,174,175,176,177,180,66,181,59,61,62,182, 183, 184, 239, 185,69,2,278,283,284,189, 188, 422, 420,190,294,405,424, 425,427,428,129,431,148,435,437,440,64,186,187,218,158,162, 15 443,157,449,450,453,454,260,455,456,457,458,459,460,461,462, 211,195,408,466,468,469,470,471,472,473,474,475,476,478,479, 480, 481 and 68 effect an aphid mortality of 90 - 100%. Example 9 20 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 25 sealed and then stored in a climatized chamber (16 hours of light/day, 250C, 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), the preparations of Examples Nos 41, 43, 44, 46, 47, 1, 48, 291, 293, 167, 168, 170, 171, 230, 30 166,172,173,50,52,51,53,54,55,57,174,175,176,180,66,181,60, 61, 62,182, 183,184,185,69,2,68,404,419,189,188,421,115,422, 420, 26, 423,190,294,405,424,425,426,427,428,429,129,128,431, 148, 65, 433, 434, 435, 436, 437, 64,186,187, 92,158,162,157, 449, 450, 452, 453, 454, 260, 455, 456, 457, 458, 459, 460, 461, 462, 211, 408, 105 464, 466, 67, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482 and 70 effect a mortality of 90 - 100%. Example 10 5 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 pl of an aqueous solution of the formulated preparation to be 10 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 250C in a climatized 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 15 compound), the preparations of Examples Nos 41, 42, 43, 44, 46, 47, 1, 111,48,291,293, 167, 170,171,230,235, 172, 50, 51, 52, 54, 55, 57, 237,174,175,176, 177,179, 180, 58, 66, 181, 59, 276, 60, 61, 62,182, 183,184,185,69,2,278,283,284,68,404,419, 188,116,421,422,420, 190, 294, 405, 424,129,130,148, 65, 433, 434, 435, 437, 440, 64,158, 20 162, 443, 448, 455, 458, 466, 468, 469, 470, 472, 473, 479, 480 and 70 effect a mortality of 90 - 100%. Example 11 Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are 25 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 climatized chamber 30 (16 hours of light/day, 250C, 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), the preparations of Examples Nos 41, 42, 43, 44, 46, 47,1,48,291,293,167,168,169,170,171,112,230,166,235,172,231, 106 173, 50, 51, 54, 55, 56, 57, 174, 175, 176, 177, 179, 180, 66, 181, 60, 61, 62,182,183 184, 238, 239,185, 69, 2, 278, 283, 284, 68, 404, 418, 419, 189,188,116,421,115,422,420,26,423,190,294,405,424,425,426, 427,428,429,129,431,114,130,148,65,433,434,435,436,437,438, 5 439,440,441,442,443,444,309,64,186,187,220,218,219,158,162, 464,466,467,468,469,470,471,472,473,474,475,476,477,478,479, 480, 481, 482, 483, 279, 339, 340 and 70 effect a mortality of 90 - 100%. Example 12 10 Part A of the test (contact activity): Approximately 5000 recently hatched, active (mobile) larvae (2nd development stage) of the root gall nematode (Meloidogyne incognita) are placed into a glass vessel containing an aqueous solution of the formulated preparation to be examined (final volume 20 ml). After the nematode larvae has been permanently exposed 15 for 6 days, the percentage of the specimen which has ceased to move (been immobilized) owing to the effect of the preparation is determined by comparison with the untreated controls (percent nematicidal contact activity). 20 Part B of the test (soil-drench activity): For this test, the entire solution from part A of the test (active compound and pre-treated nematode larvae) is poured into a pot filled with 60 ml of soil in which three 9-day-old cucumber plants (Cucumis sativus) have been planted. This drench application reduces the active compound content, based on the volume of the soil, to 25 one third of the active compound content in part A of the test. After two weeks in a greenhouse at about 260C (the plants being watered twice a day), the root balls of the cucumber plants are carefully washed out from the soil mixture infested with nematodes. The number of root galls per plant is counted and compared with the infestation of untreated control 30 plants. The reduction of infestation in percent as activity criterion is calculated using Abbott's formula (percent nematicidal soil-drench activity). At a concentration of 3 ppm in part A of the test and 1 ppm in part B of the test, respectively, (based in each case on the content of active compound), 107 the preparation of Example No. 181 has a 90 - 100% activity against the root gall nematode Meloidogyne incognita. Example 13 5 In each case 1 ml of the preparation to be examined, which has been emulsified in acetone, is applied uniformly to the inside of the lid and bottom of a Petri dish. After the coating has dried, batches of 10 adult house flies (Musca domestica) are introduced into the Petri dish. The dishes are sealed and kept at room temperature, and the mortality of the 10 test species is determined after 3 hours. At a concentration of 300 ppm (based on the content of active compound), the preparation of Example No. 39 effects a mortality of 90 - 100% in the test species used. Example 14 15 In each case 1 ml of the preparation to be examined, which has been emulsified in acetone, is applied uniformly to the inside of the lid and bottom of a Petri dish. After the coating has dried, batches of 10 larvae of the German cockroach (Blattella germanica) are introduced into the Petri dish. The dishes are sealed and kept at room temperature, and the 20 mortality of the test species is determined after 3 days. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 40 and 110 effect a mortality of 90 - 100% in the test species used. 25 Examples 15 Bean plants (Phaseolus vulgaris) are populated for 48 hours with adults of the white fly (Trialeurodes vaporariorum). After the leaves have been uniformly covered with eggs, the plants are sprayed to run-off point with an aqueous solution of the formulated preparation to be examined. After 30 11 days (development time for L2 - L3 larval stages), the ovicidal and larvicidal activity is determined. At a concentration of 300 ppm (based on the content of active compound), the preparation of Example No. 185 shows an efficacy of 90 - 100%.

108 Example 16 Field beans or bell pepper plants which were severely infested with the green peach aphid (Myzus persicae) are sprayed to run-off point with an aqueous solution of the formulated preparation to be examined. The 5 mortality of the aphids is determined after 3 days. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 46, 55, 180, 183, 184, 182, 185, 62, 68 effect a mortality of 90- 100%. 10 Example 17 A cabbage leaf is dipped for about 5 seconds into an aqueous solution of the formulated preparation to be examined. After drying, the cabbage leaf treated in this manner is transferred into a culture container and populated with ten larvae of the cabbage moth (Plutella maculipennis). The container 15 is subsequently sealed with a lid. After 3 days storage at about 230C, the effect of the preparation on the larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 55, 180, 182, 184, 185, 68, 190, 435 effect a larvae mortality of 90 - 100%. 20 Example 18 Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into brown bottles filled with tap water and then populated for 48 hours with adult white flies (Trialeurodes vaporariorum). After the leaves 25 have been uniformly covered with eggs, they are sprayed to run-off point with an aqueous solution of the formulated preparation to be examined. After 11 days (development time for L2 - L3 larvae stages), the ovicidal and larvicidal activity is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 46, 30 55, 62, 68, 180, 182, 183, 184, 190, 435 show an efficacy of 90 - 100%. Example 19 Rice seed is germinated on moist cotton in cultivation glasses. After the plants have grown to a stem length of approximately 8 cm, the leaves are 109 dipped 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 transferred into culture containers and populated with in each case 10 larvae (L3 stage) of the rice leafhopper Nephotettix cincticeps. The 5 sealed culture containers are stored at 230C, and after 4 days, the mortality of the leafhopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 46, 55, 62, 68, 180 effect a mortality of 90 - 100% in the test species used. 10 Example 20 Oats (Avena sativa) which are densely populated by the oat grain aphid (Rhopalosiphum padi) are sprayed to run-off point with an aqueous solution of the formulated preparation to be examined. The mortality of the 15 oat grain aphids is determined after 3 and 7 days. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 46, 55, 62, 68, 180, 182, 183, 184, 185, 190, 435 effect a mortality of 90 - 100%. 20 Example 21 Ten Li larvae of the codling moth (Carpocapsa pomonella) are placed in a Petri dish filled with culture medium. Culture medium and added larvae are then sprayed with an aqueous solution of the formulated preparation to be examined. The Petri dish is then sealed with a lid. After 8 days storage at 25 about 230C, the effect of the preparation on the larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 180, 182, 184 effect a larvae mortality of 90- 100%. 30 Example 22 Approximately 20 eggs of the codling moth (Carpocapsa pomonella) are placed in a Petri dish filled with culture medium. Culture medium and eggs are then sprayed with an aqueous solution of the formulated preparation to be examined. The Petri dish is then sealed with a lid. After 8 days storage 110 at about 23*C, the effect of the preparation on the eggs and the larvae which may have hatched therefrom is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples Nos 55, 62, 180, 182, 183, 184, 185, 190, 435 effect a mortality 5 of 90 - 100%. Use as fungicide Example 23-27 10 The compounds were tested for their activity against one or more of the following organisms: Plasmopara viticola 15 Erysiphe graminis f. sp. tritici Pyricularia oryzae Leptosphaeria nodorum Phytophthora infestans 20 Aqueous solutions or dispersions of the compounds at the desired con centrations, with addition of a wetting agent, were applied to leaves or stalks of the test plant. The plants or parts of plants were inoculated with the test pathogen in question and kept under controlled environmental conditions which are suitable for plant growth and disease development. 25 After a suitable time, the extent to which the diseased plant was infested was estimated visually. The compounds are assessed using a scale from 1 to 3 in which 1 means no low-level control, 2 means medium-control and 3 means good to complete control. At a concentration of 500 ppm (w/v) or less, the following compounds scored 2 or more against the 30 abovementioned fungi. Plasmopara viticola: 110, 40, 39, 48, 291,167, 166, 180,174,184, 183, 182,62,185,189,188 Erysiphe graminis: 1,41,167,172,166,180,174,66,184,183, 111 182,185,418,189,188 Pyricularia oryzae: 40, 111, 44,174, 66,184,182, 418,189,188 Leptosphaeria nodorum: 110, 39, 43,167,172,166,180,174, 66,184, 183,182,62,185,418,189,188 5 Phytophtora infestans: 110, 40, 39,180, 66, 184,183, 182, 62,185, 404, 418,419,188

Claims

1. A compound of the formula I 5 Y-Z x R3 (1)n A 1 10 R2 D Ri in which (1) A is CH and D is N*R 15 or A is nitrogen and D is N*R or 20 A is N*R and D is nitrogen, where R is E R6 25 R 4 R 5

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

(3) R 1 is hydrogen, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or 30 (C 3 -C)-cycloalkyl;

(4) R 2 and R 3 are identical or different and are each hydrogen, (C1-C 4 )-alkyl, (C1-C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-haloalkynyl, 113 (Cl-C 8 )-trialkylsilylalkynyl, preferably dimethyl-(C-C 8 )-alkyl silylalkynyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, (C C4) alkoxy-(C-C4)-alkyl, (C 1 -C 4 )-haloalkoxy-(Cl-C 4 )-alkyl, (C-C 4 )-alkoxy-(Cl-C 4 )-haloalkyl, (Cl-C 4 )-haloalkoxy-(Cl C4) 5 haloalkyl, amino, monosubstituted amino, disubstituted amino, halogen, hydroxyl, (Cl-C 4 )-hydroxyakyl, (C 1 C4) alkanoyl, (C 1 -C 4 )-alkanoyl-(C 1 -C 4 )-alkyl, (Cl-C 4 )-halo alkanoyl, (C 3 -C 5 )-cycloalkyl, (C 3 -C 5 )-halocycloalkyl, cyano, (Cr-C 4 )-cyanoalkyl, nitro, (Cr-C4)-nitroalkyl, thiocyano, 10 (Ci-C 4 )-thiocyanoalkyl, (Cl-C 4 )-alkoxycarbonyl, (Ci C4) alkoxycarbonyl-(Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkoxycarbonyl, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylthio-(Cl-C 4 )-alkyl, (C 1 -C 4 ) haloalkylthio, (C 1 -C 4 )-alkylsulfinyl, (C 1 C 4 )-haloalkylsulfinyl, (C 1 -C 4 )-alkylsulfonyl or (C 1 -C 4 )-haloalkylsulfonyl; or 15 R 2 and R 3 join with the linking carbon atoms to form an unsaturated

5- or 6-membered isocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH 2 , 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 20 may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (Cl-C4)-alkyl, (Cl-C 4 )-haloalkyl, preferably trifluoromethyl, halogen, (C 1 -C 4 )-alkoxy or (Cl-C 4 )-haloalkoxy; or R 2 and R 3 join with the linking carbon atoms to form a saturated 5-, 25

6- or 7-membered isocyclic ring which may contain oxygen and/or sulfur instead of one or two CH 2 groups and which may be substituted by 1, 2 or 3 (C 1 -C 4 )-alkyl groups; (5) X is 0, S(O)q where q = 0, 1 or 2, NR 7 or CR 8 R 9 , where R 7 is 30 hydrogen and R 8 and R 9 independently of one another are each hydrogen or (C 1 -C 4 )-alkyl, (6) Y - Z together are a (Cl-C 20 )-hydrocarbon radical which is straight chain or branched and in which one or more, preferably up to three, 114 CH 2 may be replaced by hetero atom radicals such as 0, NR 1 O, S, SO, SO2 or SiR 1 R 12 , where R 10 is hydrogen, (C 1 C 4 )-alkyl or (Cl-C 4 )-acyl, and R 11 and R 12 are identical or different and are each independently of the other (Cl-C 4 )-alkyl, phenyl or substituted 5 phenyl, and where this (C 1 -C 20 )-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 10 (C-C)-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkenyl, 15 halogen, halo-(Cl-C 4 )-alkyl, halo-(Cl-C 4 )-alkoxy, hydroxyl and (C 1 -C 4 )-acyl; or, if not included in the above definitions, 20 (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 25 (C 7 )-alkyl, (C 2 -C 4 )-alkenyl, (C 3 -C 7 )-alkynyl, (C 3 -C 7 )-cycloalkyl, 30 (C 3 -C 7 )-cycloalkenyl, halogen, halo-(Cl-C 4 )-alkyl, halo-(C-C 4 )-alkoxy, hydroxyl and 115 (C 1 -C 4 )-acyl; and (8) Z is aryl or O-aryl, where aryl is preferably a naphthyl or phenyl group which may be substituted by one or more, preferably 5 up to five, in particular up to three, identical or different radicals selected from the group consisting of halogen, (C 3 -C)-cycloalkyl, 10 (C 3 -C 8 )-cycloalkenyl, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, 15 phenyl, substituted phenyl, NO 2 , 0 20 -C-R', acetoxy, hydroxyl, cyano, SiR' 4 R 15 R 16 , 25 O-SiR 1 4 R 1 R 16 , NR 17 R 18 S(0)R19, S0 2 R 1 , (C1-C 1 2 )-alkyl, 30 (C2-C1 2 )-alkenyl, (C 1 -C 12 )-alkoxy and (C 1 -C 12 )-alkylthio; and 116 R 13 is (C C- 7 )-alkyl, halo-(C-C 7 )-alkyl, (C 3 -0 7 )-cycloalkyl, halo-(C 3 -C 7 )-cycloalkyl, (C-C 7 )-alkoxy, phenyl or substituted phenyl; R 14 , R 15 and R1 6 are identical or different and are each 5 independently of one another (C 1 C 4 )-alkyl, phenyl and/or substituted phenyl; R1 7 and R 18 are identical or different and are each independently of the other hydrogen, (C-C 4 )-alkyl and/or (Cl-C4)-acyl; 10 R 19 is (Cl-C 10 )-alkyl, phenyl or substituted phenyl; where in (Cl-C1 2 )-alkyl, (C-C1 2 )-alkoxy, (Cl-C12)-alkylthio and (C 2 -C 12 )-alkenyl one or more, preferably up to 3, CH 2 groups may be replaced by hetero atom radicals such as 0, 15 S, SO, SO 2 , NR 1 ' or SiR 1 "R 12 '; R 10 ', R"' and R1 2 . have the meanings of R1 0 , R 11 , R 12 ; the (Cl-C 1 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 20 number), identical or different radicals selected from the group below consisting of halogen, halo-(C 1 -C 4 )-alkoxy, hydroxyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkenyl, (Cl C4) acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (C1C7) 25 alkoxy and (Cl-C 7 )-alkylthio radicals, one or more, preferably up to three, CH 2 groups may be replaced by 0, 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 30 consisting of halogen, phenyl, substituted phenyl, (C3-C8) cycloalkyl, (C 3 -C 8 )-cycloalkenyl, phenoxy and substituted phenoxy; or, if not included in the above definitions, 117 (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 5 (C-Cy)-alkyl, (C2-C4)-alkenyl, (C 3 -C)-alkynyl, (C 3 -C 7 )-cycloalkyl, 10 (C 3 -C 7 )-cycloalkenyl, halogen, halo-(Cl-C 4 )-alkyl, halo-(Cl C 4 )-alkoxy, hydroxyl and 15 (C0-C 4 )-acyl; and (10) Z is (0 3 -C 8 )-cycloalkyl or (C 5 -C 8 )-cycloalkenyl, where a CH 2 group of the carbocycle may be replaced by NR 20 ; R 20 is phenyl or substituted phenyl and the (C 3 -C 8 )-cycloalkyl 20 or (C 5 -C,)-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 25 (C-C 18 )-alkyl, (C 3 -C.)-cycloalkyl, (C 3 -C)-cycloalkoxy, (C2-Cl)-alkenyl, (C2-C1 8 )-alkynyl, 30 (C-C1 2 )-alkoxy, (C1 -C 1 2 )-alkanoyloxy, formyl, (C2-C1 2 )-acyl, (Cl -C1 2 )-alkyl-oxycarbonyl, 118 SiR 21 R 22 R 23 , N24R25, 0 || 5 C-NR2R hydroxyl, halogen, aryl, heteroaryl, 10 O aryl, o heteroaryl, CH 2 0 aryl, CH 2 0 heteroaryl, (Cl-C1)-alkanediyldioxy, 15 (Cl-C 13 )-alkyl-oximino and (C 2 -C 18 )-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH 2 groups in the (C-18)-, (C2-C18)-, (C1-C12)-, (C2-C12)- and (C1-C13) hydrocarbon radicals mentioned may be replaced by hetero 20 atom radicals such as 0, NR 1 O" or SiR 1 "R 12 ", these hetero atom radicals preferably not being adjacent to one another, where R 10 ", R 11 " and R 1 2 N have the meanings of R 10 , R 1 , R1 2 and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these 25 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, 30 substituted phenyl, 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; 119 where aryl is as defined under (8); where R 24 and R 25 are identical or different and are each independently of the other hydrogen, (C 1 C 4 )-alkyl, (C1C4) acyl, (C 3 -C 6 )-cycloalkyl, phenyl and substituted phenyl and 5 where R 21 , R 22 , R 23 are identical or different and are each independently of the others (Cl-C1 8 )-alkyl, (C-C 18 )-alkoxy, (C 3 -C)-cycloalkyl and aryl, where in the (C-C1 8 )-hydro carbon radicals more than one, preferably up to three, nonadjacent CH 2 groups may be replaced by oxygen and 10 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 R 22 ) 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 (C1-C18) 15 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 20 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 25 (11) Y is a bond; and (12) Z (a) is a group of the formula ll 30 X Ry where X1 independently of the other is sulfur or oxygen; Rz is hydrogen, (C 1 C 4 )-alkyl, trifluoromethyl or (C1C4)- 120 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 5 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 10 such as oxygen, S(O)x, where x = 0, 1 or 2, NR 26 or SiR 27 R 28 , where R 26 is hydrogen, (C-C4)-alkyl, (Cl-C 4 )-alkoxy or (Cr-C 4 )-alkanoyl and R 27 and R 28 are each (C 1 C 4 )-alkyl, preferably methyl; and where additionally 3 to 12 atoms of these 15 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 20 maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, hetero cyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, 25 cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxy carbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, 30 cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkyl sulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just 121 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 RV and Rz together form a three- to eight-membered ring 5 system which is spirocyclically linked to the ring system containing the hetero atoms X1 and where one or two CH 2 groups, preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR 29 , where R 29 is hydrogen, 10 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 15 formed by RV and Rz may be unsubstituted or substi tuted 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, arylalkyl, arylalkoxy, arylalkylthio, 20 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 25 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 Rz, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4 30 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 122 substituents; in particular those groups of the formula I where RY is (Cl-C 20 )-alkyl, (C 2 -C 20 )-alkenyl, (C 2 -0 20 )-alkynyl, 5 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 10 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, NR 26 or SiR 27 R 28 , where R 26 is hydrogen, (C-C 4 )-alkyl, (C-C4)-alkoxy 15 or (C-C4)-alkanoyl and R 27 and R 28 are each (C1C4) alkyl, preferably methyl, and where additionally 3 to 12 atoms of these hydro carbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals 20 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) 25 cycloalkoxy, (C 3 -C 8 )-cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (Cl-C1 2 )-alkanoyl, (C 3 -C 8 )-cycloalkanoyl, (C2-C1 2 )-haloalkanoyl, aroyl, aryl-(Cl-C 4 )-alkanoyl, (C 3 -C 8 )-cycloalkyl-(C 1 C4) alkanoyl, heterocyclyl-(C-C 4 )-alkanoyl, (C1 C12) 30 alkoxycarbonyl, (Cl-C1 2 )-haloalkoxycarbonyl, (C3-C8) cycloalkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 C 4 ) alkoxycarbonyl, aryl-(Cl-C 4 )-alkoxycarbonyl, heterocyclyl-(C-C 4 )-alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, (Cl-C1 2 )-alkanoyloxy, 123 (C2-C 12 )-haloalkanoylalkoxy, (C 3 -C 8 )-cycloalkanoyl oxy, (C 3 -C 8 )-cycloalkyl-(Cl-C4)-alkanoyloxy, aroyloxy, aryl-(Cl-C 4 )-alkanoyloxy, heterocyclyl-(Cl C4) alkanoyloxy, (Cl-C 12 )-alkylsulfonyloxy, arylsulfonyloxy, 5 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 10 different substituents, or where RV and Rz together form a three- to eight membered ring system, which is spirocyclically linked to the ring system containing the hetero atoms X 1 and where one or two CH 2 groups, preferably one CH 2 15 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR 29 , where R 29 is hydrogen, (C-C)-alkyl, (C-C)-alkoxy, (Cl C8) alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be 20 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 RV and Rz may be unsubstituted or substituted by up to three, but preferably one, 25 substituents and where these substituents are identical or different and are each (C-C)-alkyl, (C1C8) haloalkyl, (C-C)-alkoxy, (Ci-C 8 )-alkylthio, (C 3 -C 8 ) cycloalkyl, (C 3 -C,)-cycloalkoxy, (C 3 -C 8 )-cycloalkylthio, aryl, aryloxy, arylthio, aryl-(Cl-C 4 )-alkyl, aryl-(Cl-C 4 ) 30 alkoxy, aryl-(Cl-C 4 )-alkylthio, heterocycyl, heterocyclyloxy, heterocyclylthio, (C-C)-trialkylsilyl, preferably (C 1 -C 8 )-alkyldimethylsilyl, or (Ci C8) alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just 124 mentioned may be [lacuna] 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 Rz, 5 together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decahydro naphthalene or benzocycloheptane system and where the benzene ring in these condensed systems may be 10 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 1 carries only the 15 substituent RY, the substituents X and RY are preferably cis to each other; Rz is hydrogen, (Cl-C 4 )-alkyl, trifluoromethyl or (ClC4) alkoxy; or 20 (b) is a group of the formula Ill -' Y 3 (y 2 )m (Zi - R )nI) 25 where yl, y 2 and Y 3 independently of one another are each a group of the formula -0-, -CO-, -CNR 30 -, -S(O)r- where r = 0, 1 or 2, -N(O)IR 30 - where I = 0 or 1 or a group of the 30 formula CR 31 R 32 ; or Y' or Y 3 stands in place of a direct bond, where R 30 is hydrogen, (Cl C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (C2-C4) alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C2-C4)- 125 haloalkynyl, (C-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, (Cl-C4)-alkylthio, (Cl-C4)-haloalkylthio, (Cl-C4) alkanoyl, (C 2 -C 4 )-haloalkanoyl, (C 3 -C 5 )-cycloalkyl, (C 1 -C4)-alkylsulfonyl, (Cl-C 4 )-haloalkylsulfonyl, 5 (C-C 4 )-alkoxy-(Cl-C 4 )-alkyl, (Cl-C 4 )-alkoxycarbonyl; R 31 and R 32 independently of the other are each hydrogen, hydroxyl, halogen, cyano, (Cl-C 4 )-alkyl, (Cl-C 4 )-halo alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C2-C4) alkynyl, (C 2 -C 4 )-haloalkynyl, (C 3 -C 5 )-cycloalkyl, 10 (Cr-C 4 )-alkanoyl, (C 1 -C 4 )-haloalkanoyl, (C 1 -C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, (Cl-C 4 )-alkylthio or (C1C4) haloalkylthio; mi is 0, 1, 2, 3 or 4, preferably 1 or 2; ni is 0, 1, 2, 3 or 4, preferably 1 or 2; 15 Z 1 is a direct bond, NR 33 , 0, S(O)s where s = 0, 1 or 2, OS0 2 , S0 2 0, NR 34 SO 2 , S0 2 NR 35 , SiR 36 R 37 or U-C-V, il W 20 where R 36 and R 37 are each (C-C 4 )-alkyl or phenyl, preferably methyl; U is a direct bond, NR 38 or 0; W is oxygen or sulfur, preferably oxygen; 25 V is a direct bond, NR 39 or oxygen, where R 33 , R 34 , R 35 , R 38 and R 39 are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl; Rq are substituents which are independent of one another and each is halogen, cyano, nitro, (C-C 20 )-alkyl, 30 (C 2 -C 20 )-alkenyl, (C 2 -C 20 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C)-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(0)x where 126 x = 0, 1 or 2, NR 40 or SiR 41 R 42 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), 5 identical or different radicals D R 43 , or Rq 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 D 2 R 44 , or two adjacent radicals; 10 ZV-Rq 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 0, S and N and which is unsubstituted or substituted by one or more 15 radicals selected from the group consisting of halogen, (C 1 C 4 )-alkyl and oxo, or R 33 , R 35 or R 39 independently of one another may combine with the Rq located at Z to form a 4- to 8-membered ring system in which one or two CH 2 groups, 20 preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S(O)t where t = 0, 1 or 2 or NR45 where R 40 is hydrogen, (C 1 C 4 )-alkyl, (C 1 C 4 )-alkoxy or (Cl1C4) 25 alkanoyl; R 41 and R 42 independently of the other are each (Cl1C4) alkyl, preferably methyl; D' and D 2 are independent of each other and each is a direct bond, oxygen, S(O)k, SO20, OS0 2 , CO, OCO, Coo, 30 NR 46 , S0 2 NR 46 , NR 46 SO 2 , ONR 46 , NR 46 0, NR 46 CO, CONR 46 or SiR 47 R 48 , and k = 0, 1 or 2, where R 46 independently of the others is hydrogen, (C-C 4 )-alkyl, (Cl-C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl; R 47 and R 48 independently of the other are each (C1C4)- 127 alkyl; R 43 and R 44 independently of the other are each hydrogen, cyano, nitro, halogen, (Cl-C)-alkyl, (C-C)-haloalkyl, (C 2 -C 8 )-alkenyl, (C 2 -CO)-haloalkenyl, (C 2 -C)-alkynyl, 5 (C 2 -C)-haloalkynyl, (0 1 -C 8 )-alkoxy-(C 1 -C 4 )-alkyl, (Cl-C 8 )-haloalkoxy-(Cl-C 4 )-alkyl, (C-C)-alkylthio (C-C 4 )-alkyl, (Cl-C 8 )-haloalkylthio-(Cl-C 4 )-alkyl, (C 3 -C)-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 3 -C 8 ) cycloalkyl-(Cl-C 4 )-alkyl, (C 4 -C 8 )-cycloalkenyl-(Cj-C 4 ) 10 alkyl, aryl, heterocyclyl, aryl-(Cl-C 4 )-alkyl or heterocycly-(Cl-C 4 )-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 15 number) identical or different substituents R 49 , or R 43 and R 44 located at the same carbon atom together are an oxo group, where R 49 is (C 1 C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, 20 (Cl-C 4 )-haloalkoxy, cyano, nitro or halogen; R 45 is hydrogen, (C-C 8 )-alkyl, (Cl-C 4 )-haloalkyl, (C1C4) alkoxy, (Cl-C 4 )-alkylthio, (C 3 -C 5 )-cycloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 )-alkynyl, (Cl C 4 )-alkanoyl, (C2-C4) haloalkanoyl, (C 2 -C 4 )-alkoxyalkyl, phenyl-(Cl C 4 )-alkyl 25 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 5 o, where R 50 is (C 1 -C 4 )-alkyl, (C0-C 4 )-haloalkyl, (C0 1 C 4 )-alkoxy, 30 (C 1 -C 4 )-alkylthio, halogen or cyano; or, if not included in the above definitions, 128 (c) is a group of the formula IV Y 4 W 1 --R t Z 2 Ru 5 where Y 4 is a direct bond or CH 2 ; Z 2 is oxygen, NR 51 , S(O)m where m = 0, 1 or 2; Ru and W1-Rt are substituents of the heteroaliphatic ring 10 system, where Ru is hydrogen, halogen, cyano, (Cl-C4)-alkyl, (C1C4) haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-haloalkynyl, (C 3 -C 6 )-cyclo alkyl, (C 4 -C 6 )-cycloalkenyl, (Cl-C 4 )-alkoxy, (Cl C4) 15 haloalkoxy, (Cl-C 4 )-alkanoyloxy, (Cl-C 4 )-haloalkanoyl oxy, (C C 4 )-alkylthio or (Cl-C 4 )-haloalkylthio; W 1 is a direct bond, oxygen, -NR 52 -, -CO-, -COO-, CONR 52 -, sulfur, -C=N-, -C=N-0- or -NR520-; Rt is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or 20 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, NR 53 or SiR 54 R 55 , and where these last 5 25 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 D 3 R 56 , or Rt may be aryl or heterocyclyl, where both of these 30 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 4 R 57 , or Ru and Rt together form a three- to eight-membered ring system which is spirocyclically linked to the ring 129 system containing the hetero atoms Y 4 and Z 2 and in which one or two CH 2 groups, preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2, or NR 5 where R 51 is hydrogen, (Cl-C 4 )-alkyl, (C-C4)-haloalkyl, (C2-04) alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C2-C4) haloalkynyl, (Cl-C 4 )-alkoxy, (Cl C 4 )-alkanoyl, (C2-C4) haloalkanoyl, (Cl C 4 )-alkoxy- (Cl-C 4 )-alkyl, (C-C4) 10 alkylthio-(Cl C 4 )-alkyl, (Cl-C 4 )-alkoxycarbonyl, (Cl-C 4 )-alkylsulfonyl, (C-C4)-haloalkylsulfonyl, phenylcarbonyl, phenyl-(Cl-C 4 )-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 15 maximum number) identical or different substituents R 59 ,or R 51 is CONR 60 R 61 where R 60 and R 6 1 independently of the other are each hydrogen, (Cl-C 4 )-alkyl or phenyl, where the phenyl group may 20 be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R 62 , and R 62 and R 59 independently of the other are each (CC4) alkyl, (Cl C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl C4) 25 haloalkoxy, (Cl-C 4 )-alkylthio or halogen; R 52 is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkanoyl or (C3-05) cycloalkyl; R 53 is hydrogen, (C 1 C 4 )-alkyl, (Cl C 4 )-alkoxy or (Cl-C4) alkanoyl; 30 R 54 and R 55 independently of the other are (Cl-C 4 )-alkyl, preferably methyl; R 58 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 130 of fluorine up to the maximum number) identical or different substituents R 63 . R63 may be (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (C1C4) alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro or halogen, 5 and the ring system formed by Ru and Rt may be unsubstituted or substituted by up to three, but preferably one, substituents D 5 R 64 , or the ring system formed by Ru and Rt, together with a further benzene ring or cyclohexane ring, forms a condensed ring 10 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) 15 identical or different substituents D 6 Res, where D 3 , D 4 , D 5 and D 6 are independent of one another and are each a direct bond, oxygen, S(O)k, S020, OSO2, CO, OCO, Coo, S0 2 NR 66 , NR 66 S0 2 , NR 66 0, ONR 66 , NR 66 , NR 66 CO, CONR 6 6 or SiR 67 R 6 8 , where k = 0, 1 20 or2; and R 56 , R 57 , R 6 4 and R 6 5 independently of one another are each hydrogen, cyano, nitro, halogen, (C-C)-alkyl, (C-C)-haloalkyl, (C 2 -C,)-alkenyl, (C 2 -C 8 )-haloalkenyl, (C 2 -C)-alkynyl, (C 2 -C 8 )-haloalkynyl, (C -Cs)-alkoxy 25 (Cl-C 4 )-alkyl, (C -C 8 )-haloalkoxy-(Cl-C 4 )-alkyl, (Cl C 8 )-alkylthio-(Cl-C 4 )-alkyl, (Cl C 8 )-haloalkylthio (Cl-C 4 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(Cl C 4 )-alkyl, (C 4 -C 8 )-cycloalkenyl (Cl-C 4 )-alkyl, aryl, heterocyclyl, aryl-(Cl C 4 )-alkyl or 30 heterocyclyl-(CC 4 )-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 R 69 , where 131 R 66 independently of the others is hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl and R 67 and R 6 8 independently of the other are each (CC4) alkyl, and 5 R 69 independently of the others may be (C 1 C 4 )-alkyl, (Cl C 4 )-haloalkyl, (Cl C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro, halogen, (C-C 4 )-alkanoyl or (C2-C4) haloalkanoyl, or two of the radicals R 56 , R 57 , R 64 , R 65 , R 69 which are located at the same carbon 10 atom together, and in each case independently of the others, are an oxo group; in particular those groups of the formula IV where Rt is hydrogen, (C 1 C-)-alkyl, (C 2 -0 8 )-alkenyl, (C2-C) 15 alkynyl, (C 3 -C 8 )-cycloalkyl or (C 4 -C 8 )-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, NR 53 or 20 SiR 54 R 55 , 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 D 3 R 56 , or 25 Rt 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 4 R 57 , or Ru and Rt together form a five- or six-membered ring system 30 which is linked, preferably spirocyclically, with the ring system containing the hetero atoms Y 4 and Z 2 , and in which one CH 2 group may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR 58 , where 132 R 53 is hydrogen, (C-C 4 )-alkyl, (C-C 4 )-alkoxy or (C1C4) alkanoyl and R 54 and R 55 independently of the other are (C 1 C 4 )-alkyl, preferably methyl; 5 R 58 is hydrogen, (C-C)-alkyl, (Cl-C 8 )-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 63 , and 10 R63 may be (C 1 C 4 )-alkyl, (C-C 4 )-haloalkyl, (C1C4) alkoxy, (C 1 C 4 )-haloalkoxy, cyano, nitro or halogen, and the ring system formed by Ru and Rt may be unsubstituted or substituted by up to three, but preferably one, substituents D 5 R 64 , or the ring system 15 formed by Ru and Rt, 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 20 may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D 6 Res, where in the compounds where the carbon atom between Y 4 and Z 2 where Y = CH 2 only carries the substituent W1-Rt, 25 the substituents X and W1-Rt are cis to each other; D 3 , D 4 , D 5 and D 6 are independent of one another and are each a direct bond, oxygen, S(O)k, S0 2 0, OS0 2 , CO, OCO, COO, S0 2 NR 66 , NR 66 S0 2 , NR 66 0, ONR 66 , NR 66 , NR 66 CO or CONR 66 , and k = 0, 1 or 2, 30 R 66 independently of the others is hydrogen, (Cl-C 4 )-alkyl, (C 1 C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl and R 56 , R 57 , R 6 4 and R 65 independently of one another are each hydrogen, cyano, nitro, halogen, preferably fluorine, (C C)-alkyl, (C 3 -C 8 )-cycloalkyl, aryl, heterocyclyl, 133 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 5 substituents R 69 , where R 69 independently of the others may be (Cl-C 4 )-alkyl, (Cl C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro, halogen, or two of the radicals R 56 , R 57 , R 64 , R 65 , R 69 which are located at the same carbon 10 atom, together and in each case independently of the others, are an oxo group; (13) R 4 is hydrogen, halogen, (Cl-C 4 )-alkyl; (14) R 5 is hydrogen, halogen, (C-C 8 )-alkyl, (C 2 -C)-alkenyl, (C2-C8) 15 alkynyl, aryl or (C 3 -C)-cycloalkyl, where aryl is as defined under (8); M (15) E is -C-, where M is oxygen, sulfur or NR 0 and R 70 is aryl, 20 heteroaryl, substituted heteroaryl, hydroxyl, (Cl-C 8 )-alkoxy, aryloxy, heteroaryloxy, substituted heteroaryloxy, mono- or disubstituted amino, where aryl is as defined under (8); (16) R 6 is (Cl-C 20 )-alkyl, (C 2 -C 20 )-alkenyl, (C 2 -C 20 )-alkynyl, (C3-08) cycloalkyl, aryl or heteroaryl; 25 and, if not included in the above definitions, the carbon radicals mentioned under (13) to (16) 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, cycloalkyl, 30 phenoxy, substituted phenoxy, phenyl, substituted phenyl, and the aryl and heteroaryl radicals mentioned under (16) 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 Z 1 -R , where 134 Z 1 is a direct bond, NR 33 ', 0, S(O)s where s = 0, 1 or 2, OSO2, SO20, NR 34 'SO 2 , S0 2 NR 3 5 , SiR 36 'R 37 ' or U'-C-V', 11 W' 5 where R 36 ' and R 37 are each (Cl-C 4 )-alkyl or phenyl, preferably methyl; U' is a direct bond, NR 38 ' or 0; W' is oxygen or sulfur, preferably oxygen; V' is a direct bond, NR 39 ' or oxygen, where 10 R 33 ', R 34 ', R 35 ', R 38 ' and R 39 ' are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl; Rq are substituents which are independent of one another, and each is halogen, hydroxyl, cyano, nitro, (C 1 C 20 )-alkyl, (C 2 -C 20 )-alkenyl, (C 2 -C 20 )-alkynyl, (C 3 -C)-cycloalkyl, 15 (C 4 -C 8 )-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, NR 40 ' or SiR 41 'R 42 ', and where these last 5 radicals with or without the 20 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'R 43 ', or Rq is aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of 25 fluorine up to the maximum number) identical or different radicals D 2 R 44 ', or two adjacent radicals Z"-R4 may, together with the carbon atoms that 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 30 group consisting of 0, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and oxo, or R 33 ', R 35 ' or R 39 ' may, independently of one another, together with the Rq located at Z' form a 4- to 8-membered ring system in 135 which one or two CH 2 groups, preferably one CH 2 group, may be replaced by hetero atom units such as oxygen, S(O)t where t = 0,1 or 2 or NR 45 where 5 R 40 ' is hydrogen, (C-C 4 )-alkyl, (C 1 C 4 )-alkoxy or (C1C4) alkanoyl; R 41 ' and R 42 ' independently of the other are each (C-C 4 )-alkyl, preferably methyl; D" and D2' are independent of each other and each is a direct bond, 10 oxygen, S(O)k, S0 2 0, OSO 2 , CO, OCO, COO, NR 46 ' S0 2 NR 46 ', NR 46 'SO 2 , ONR 46 ', NR 46 '0, NR 4 6 'CO, CONR 46 ' or SiR 47 'R 48 ', and k = 0, 1 or 2, where R 46 ' independently of the others is hydrogen, (C 1 C 4 )-alkyl, (Cl-C 4 )-alkanoyl or (C 3 -Cs)-cycloalkyl; 15 R 47 ' and R 48 ' independently of the other are each (C-C 4 )-alkyl; R 43 ' and R 44 ' independently of the other are each hydrogen, cyano, nitro, halogen, (COs-0)-alkyl, (Cl-C 8 )-haloalkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 )-haloalkenyl, (C 2 -C 8 )-alkynyl, (C2-08) haloalkynyl, (C1 C 8 )-alkoxy-(C-C4)-alkyl, (Cl C 8 )-haloalkoxy 20 (Ci C 4 )-alkyl, (Cl C 8 )-alkylthio-(Cl C 4 )-alkyl, (C C8) haloalkylthio-(C-C 4 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C4-C8) cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C-C 4 )-alkyl, (C4-C8) cycloalkenyl-(C-C 4 )-alkyl, aryl, heterocyclyl, aryl-(C-C4) alkyl or heterocyclyl-(Cl-C 4 )-alkyl, where in the last 8 radicals 25 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 R 4 9 , or 30 R 43 ' and R 44 ' located at the same carbon atom together are an oxo group, where R 49 ' is (C-C 4 )-alkyl, (C-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl C4) haloalkoxy, cyano, nitro or halogen; 136 R 45 ' is hydrogen, (C-C 8 )-alkyl, (Cl-C4)-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-alkylthio, (C 3 -C 5 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 ) alkynyl, (Cl-C 4 )-alkanoyl, (C 2 -C 4 )-haloalkanoyl, (C2-C4) alkoxyalkyl, phenyl-(C-C 4 )-alkyl or phenyl and the phenyl 5 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 5 o, where R 50 ' is (C-C 4 )-alkyl, (C 1 C 4 )-haloalkyl, (C 1 C 4 )-alkoxy, (C1C4) alkylthio, halogen or cyano. 10 2. A compound of the formula I as claimed in claim 1, in which 15 A isCHandDisN*R or A is nitrogen and D is N*R; 20 Qn- is an anion such as Hal~, N0 3 ~, BF 4 , BPh 4 - or PFel R 1 is hydrogen, methyl, fluorine or chlorine; R 2 and R 3 are each hydrogen, (Cl-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C2-C4) alkynyl, amino, (Cl C 4 )-alkylamino, (Cl C 4 )-dialkylamino, trimethyl 25 silylethynyl, methoxycarbonyl, (C-C 4 )-haloalkyl, (C2-C4) haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or R 2 and R 3 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 CH 2 30 unit; or R 2 and R 3 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 CH 2 unit; X is NH or oxygen. 137 3. A compound of the formula I 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, (Cl-C 4 )-alkyl radical; and 5 Z is (C 3 -C 8 )-cycloalkyl or (C 5 -C 8 )-cycloalkenyl, where a CH 2 group of the carbocycle may be replaced by NR 20 ; R 20 is phenyl or substituted phenyl and the (C 3 -C,)-cycloalkyl or (C 5 -C 8 )-cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum 10 number), identical or different radicals selected from the group consisting of (C-C1 8 )-alkyl, (C3-C.)-cycloalkyl, 15 (C 3 -C 8 )-cycloalkoxy, (C2-C1 8 )-alkenyl, (C2-C1 8 )-alkynyl, (C-C 12 )-alkoxy, (C-C1 2 )-alkanoyloxy, 20 formyl, (C2-C12 )-acyl, (C1 -C1 2 )-alkyl-oxycarbonyl, SiR 2 1 R 22 R 23 , NR 24 R 25 , 25 0 C-NR 24 R 25 hydroxyl, halogen, 30 aryl, heteroaryl, 0 aryl, 0 heteroaryl, CH 2 0 aryl, 138 CH 2 0 heteroaryl, (C1-C1 8 )-alkanediyldioxy, (C1-C1 3 )-alkyl-oximino and (C 2 -C1 8 )-alkylidene and where, if not included in the 5 above definitions, one or more, preferably up to three, CH 2 groups in the (0-C18)-, (C2-C18)-, (C1-C12)-, (C2-C12)- and (C1-013) hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as 0, NR 1 O" or SiR 1 "R 1 2 ", these hetero atom radicals preferably not being adjacent to one another, where R 10 ", R 11 " and 10 R 12 - have the meanings of R 10 , R 11 , R 12 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 15 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 20 three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R 24 and R 25 are identical or different and are each independently of the other hydrogen, (C 1 C 4 )-alkyl, (C 1 C 4 )-acyl, 25 (C 3 -C 6 )-cycloalkyl, phenyl and substituted phenyl and where R 21 R 22 , R 23 are identical or different and are each independently of the others (Cl C1 8 )-alkyl, (CC1 8 )-alkoxy, (C 3 -C 8 )-cycloalkyl and aryl, where in the (C-C1 8 )-hydrocarbon radicals more than one, preferably up to three, CH 2 groups may be replaced by oxygen and 30 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 21 and R 22 ) attached to silicon together to form a cycle, the silicon atom possibly being part of this cycle, and where additionally these (C1C1 8 )-hydrocarbon radicals with or without the 139 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 (C 3 -C 8 )-cycloalkyl or (C 5 -C 8 )-cyclo 5 alkenyl 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 10 Y is a bond; and Z (a) is a group of the formula Il X 1 RY 15 X1z where X 1 is oxygen; RY is (C 1 -C 20 )-alkyl, (C 2 -C 20 )-alkenyl, (C 2 -C 20 )-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three 20 (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 SiR 27 R 28 , where R 27 25 and R 28 are each (C 1 C 4 )-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, 30 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, (C 3 -C 8 )-cycloalkoxy, (C 3 -C 8 )-cycloalkylthio, heterocyclyl, heterocyclyloxy or (Cl C 2 )-alkoxycarbonyl, 140 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 5 substituents, or RY and Rz together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms X 1 , and where one CH 2 group may be replaced by hetero atom units such as oxygen, 10 S(O)n where n = 0, 1 or 2 or NR 2 9 , where R 29 is hydrogen, (C 1 C 8 )-alkyl, (Cl-C 8 )-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) 15 identical or different substituents, and where the ring system formed by RY and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C1C8) alkyl, (C 3 -0 8 )-cycloalkyl, aryl or aryl-(C 1 -C 4 )-alkyl, where the 20 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 Rz, together with 25 a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetra hydronaphthalene, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the 30 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 141 other; and Rz is hydrogen or 5 (b) is a group of the formula (111) M(-Z - RY ) 3 n 10 where yl, y 2 and Y 3 are each a group of the formula -0-, -S(O)r-, where r = 0, 1 or 2 or is a group of the formula CR 3 1 R 32 , or Y' or y3 stand in place of a direct bond, where R 31 and R 32 independently of the other are each hydrogen or 15 methyl; m is 1 or 2; ni is 1 or 2; Z 1 is a direct bond, NR 33 , 0, S(0)s where s = 0, 1 or 2, OS0 2 , S0 2 0, NR 34 S0 2 , S0 2 NR 35 , SiR 36 R 37 or U-C-V, where 20 i1 W U is a direct bond, NR 38 or 0; W is oxygen; V is a direct bond, NR 39 or oxygen; 25 and R 36 and R 37 are each (Cl-C 4 )-alkyl or phenyl, preferably methyl; R 33 , R 34 , R 35 , R 38 and R 39 are identical or different and are each hydrogen, (Cl-C 4 )-alkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl; 30 Rq independently of the others is (Cl-C 8 )-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 142 maximum number), identical or different radicals DiR 43 , or Rq 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 5 radicals D 2 R 44 ; D' and D 2 are independent of one another and are each a direct bond, -0-, -S(O)k-, -SO20-, -OSO2-, -Co-, -OCO-, -COO-, -NR 46 -, -So 2 NR 46 -, -NR 46 SO 2 -, -ONR 46 -, -NR 46 0-, -NR 46 CO-, -CONR 46 -, and k = 0, 1 or 2, and where 10 R 46 independently of the others is hydrogen, (C 1 C 4 )-alkyl, (Cl-C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl; R 43 and R 44 independently of the other are each hydrogen, halogen, preferably fluorine, (Cl-C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, aryl or heterocyclyl, where in the last 3 radicals the cycloaliphatic, 15 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 R 49 , where R 49 independently of the others may be (Cl-C 4 )-alkyl, (C1-C4) 20 haloalkyl, (C -C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro, halogen; or, (c) is a group of the formula IV 25 4 W1-Rt Z 2 Ru (IV) where 30 Y 4 is a direct bond or CH 2 ; Z 2 is oxygen; Ru is hydrogen, (Cl-C 4 )-alkyl, trifluoromethyl or (Cl-C 4 )-alkoxy; W 1 is a direct bond, oxygen, -CO-, -COO-, CONR 52 , sulfur, 143 -C=N-, -C=N-0- where R 52 is hydrogen, (Cl-C 4 )-alkyl, (Cl C 4 )-alkanoyl and (C 3 -C 5 )-cycloalkyl, and Rt is as defined above under (12 c). 5 4. A compound of the formula I as claimed in any of claims 1 to 3, in which R 1 is hydrogen; R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3) alkenyl, amino, (C 1 C 4 )-alkylamino, (Cl-C 4 )-dialkylamino, (C2-C3) 10 chloro- or -fluoroalkenyl, (C 2 -C 3 )-alkynyl, trimethylsilylethynyl, (Cl-C 3 )-chloro- or -fluoroalkyl, methoxymethyl, halogen or cyano; or R 2 and R 3 together with the ring system to which they are attached form the quinazoline or quinoline system, which may be fluorine substituted in the carbocyclic moiety; or 15 R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 6-membered ring, which may contain an oxygen or sulfur atom instead of a CH 2 group. 5. A compound of the formula I as claimed in any of claims 1 to 4, in 20 which X isNH; 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 25 cyclohexyl, 1,4-substitution is preferred, the substituents being cis to one another; or (b) is a group of the formula Il 30 1 Ry X Rz where 144 X 1 is oxygen; Rz is hydrogen; or (c) is a group of the formula Ill 5 - Y 3 (y 2 ) -Y M1 ( Z - R9 )W where 10 Y 1 is CH 2 ; Y 2 is CH2 Y 3 is CH 2 , O or a direct bond; mi is 1 or 15 (d) is a group of the formula IV Y4 W1-Rt _ ZK Ru (IV) 2 R 20 where Y 4 is a direct bond or CH 2 ; Z 2 is oxygen; Ru is hydrogen or methyl. 25 6. A compound of the formula I as claimed in any of claims 1 to 5, in which A is CH and D is N*R or 30 A is nitrogen and D is N*R; Q~ is an inorganic or organic anion, such as Hal-, NO 3 -, BF 4 , BPh 4 -, PFel; R 4 is hydrogen; R 5 is hydrogen, halogen, (Cl-C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C2-C8)- 145 alkenyl, (C 2 -C 8 )-alkynyl; M 5 E is -C- , where M is oxygen or sulfur; R 6 is aryl or heteroaryl, where the aryl and heteroaryl 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 Z-R where 10 Z' is a direct bond, 0, OS0 2 or U'-C-V', where || W' U' is a direct bond, or 0; W' is oxygen; 15 V' is a direct bond, NR 39 ' or oxygen; and R 39 ' is hydrogen, (Cl-C 4 )-alkyl, (C 1 C 4 )-alkoxy, (Cl-C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl; Z'-Rq' together are halogen, hydroxyl, nitro or cyano, or 20 Rq are substituents which are independent of one another and are each (Ci C 20 )-alkyl or (C 2 -C 20 )-alkenyl and 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 1 'R 43 ', or Rq' may be aryl or heterocyclyl, where these two radicals may be 25 unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D 2 R 44 '; D" and D 2 are independent of one another and are each a direct bond, -O-, -S(O)k-, 0OSO2, -CO-, -OCO-, -COO-, -NR-, -S0 2 NR 46 '-, -NR 46 'SO 2 -, -ONR 46 '-, -NR 46 '0-, -NR 46 'CO-, -CONR 46 '_, 30 and k = 0, 1 or 2, and where R 46 ' independently of the others is hydrogen, (Cl-C 4 )-alkyl, (CC4) alkanoyl or (C 3 -C 5 )-cycloalkyl; R 43 ' and R 44 ' independently of each other are each hydrogen, halogen, preferably fluorine, (Cl-C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, aryl or 35 heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic 146 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 R 4 9 , where R 49 ' independently of the others is (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (Cl 5 C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro, halogen.

7. A compound of the formula I as claimed in any of claims 1 to 6 in which R' is hydrogen; 10 R 2 is ethyl or methoxymethyl; R 3 is chlorine, bromine or methoxy, preferably those for which R 2 is ethyl and R 3 is chlorine; R 4 is hydrogen; R 5 is hydrogen or methyl; 15 M E is -C- , where M is oxygen; R 6 is aryl or heteroaryl, where the aryl and heteroaryl radicals may be substituted by one or more, preferably up to three (in the case of 20 halogen up to the maximum number), identical or different radicals Z"-R, where Z 1 is a direct bond, 0 or U'-C-V', where W' 25 U' is a direct bond, or 0; W' is oxygen; V' is a direct bond, NR 39 ' or oxygen; and 30 R 39 ' is hydrogen, (C 1 C 4 )-alkyl, (C-C 4 )-alkoxy, (C-C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl; Rq are substituents which are independent of each other and are each (C 1 -C 12 )-alkyl or (C 2 -C 1 2)-alkenyl and which may be substituted by one or more, preferably up to three (in the case of fluorine up to the 35 maximum number), identical or different radicals R 4 3 , or 147 R4 is halogen, nitro or cyano, or R4 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 2 R 44 '; 5 D 2 ' are independent of one another and are each a direct bond, -0-, -S(O)k-, -S0 2 0-, -OS0 2 -, -CO-, -OCO-, -COO-, -NR 46 '_ -S0 2 NR 46 '-, -NR 46 'S0 2 -, -ONR 46 '-, -NR 46 '0-, -NR 4 6 0'CO-, -CONR 46 '-, and k = 0, 1 or 2, and where R 46 ' independent of the others is hydrogen, (Cl-C 4 )-alkyl, (C1C4) 10 alkanoyl or (C 3 -C 5 )-cycloalkyl; R 43 ' and R 44 ' independently of the other are each hydrogen, halogen, preferably fluorine, (Cl -C 8 )-alkyl, (C 3 -C)-cycloalkyl, aryl or heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by 15 up to three (in the case of fluorine up to the maximum number) identical or different substituents R 49 , where R 49 ' independently of the others may be (Cl-C 4 )-alkyl, (C-C4)-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro, halogen. 20

8. A process for preparing compounds of the formula I as claimed in any of claims 1 to 7, which comprises reacting a compound of the formula (V) X-Y-Z R 3 25M R 2 N R where G is CH or N and R 1 , R 2 , R 3 , X, Y and Z are each as defined under formula 1, with an electrophile of the formula (VI) 30 L E R 6 R (VI) R 4 R5 148 where R 4 , R 5 , R 6 and E are each as defined under formula I and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, if appropriate with the addition of salts, and replacing, if appropriate, the anion of the compounds obtained in this manner by other 5 anions.

9. A composition comprising at least one compound as claimed in any of claims 1 to 7 and at least one formulating agent.

10 10. A fungicidal composition as claimed in claim 9, comprising a fungicidally effective amount of at least one compound as claimed in any of claims 1 to 7 together with the additives or auxiliaries which are customary for this application. 15

11. An insecticidal, acaricidal or nematicidal composition as claimed in claim 9, comprising an effective amount of at least one compound as claimed in any of claims 1 to 7 together with the additives or auxiliaries which are customary for these applications. 20

12. A crop protection composition comprising a fungicidally, insecticidally, acaricidally or nematicidally effective amount of at least one compound as claimed in any of claims 1 to 7 and at least one further active substance, preferably selected from the group consisting of fungicides, insecticides, attractants, sterilants, acaricides, nematicides and herbicides, 25 together with the auxiliaries and additives which are customary for this application.

13. A composition for use in protecting wood or as a preservative in 30 sealing compounds, in paints, in cooling lubricants for metalworking or in drilling and cutting oils, which comprises an effective amount of at least one compound as claimed in any of claims 1 to 7 together with the auxiliaries and additives which are customary for these applications. 149

14. A compound as claimed in any of claims 1 to 7 or the composition as claimed in claim 9 for use as a veterinary pharmaceutical, preferably in the control of endo- or ectoparasites. 5

15. A process for the preparation of a composition as claimed in any of claims 9 to 14, which comprises combining the active substance and the other additives and bringing the mixture into a suitable application form.

16. The use of a compound as claimed in any of claims 1 to 7 or a 10 composition as claimed in any of claims 9, 10, 12 and 13 as fungicide.

17. The use of a compound as claimed in any of claims 1 to 7 or of a composition as claimed in any of claims 9, 10 and 13 as a wood preservative or as a preservative in sealing compounds, in paints, in 15 cooling lubricants for metalworking or in drilling and cutting oils.

18. A method of controlling phytopathogenic fungi, which comprises applying a fungicidally effective amount of a compound as claimed in any of claims 1 to 7 or of a composition as claimed in any of claims 9, 10, 12 20 and 13 to these fungi or to the plants, areas or substrates infested with them or to seed.

19. A method of controlling insect pests, acarids and nematodes, which comprises applying an effective amount of a compound as claimed in any 25 of claims 1 to 7 or of a composition as claimed in any of claims 9, 11 and 12 to these insect pests, acarids and nematodes or to the plants, areas or substrates infested with them.

20. The use of a compound as claimed in any of claims 1 to 7 or of a 30 composition as claimed in any of claims 9, 11 and 12 for controlling insect pests, acarids and nematodes.

21. Seed, treated or coated with an effective amount of a compound as claimed in any of claims 1 to 7 or of a composition as claimed in any of 150 claims 9, 10, 12 and 13.