AU7300698A - Quaternary nitrogen heterocycles, method for their production and thei r use as pesticides - Google Patents

Quaternary nitrogen heterocycles, method for their production and thei r use as pesticides Download PDF

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Publication number
AU7300698A
AU7300698A AU73006/98A AU7300698A AU7300698A AU 7300698 A AU7300698 A AU 7300698A AU 73006/98 A AU73006/98 A AU 73006/98A AU 7300698 A AU7300698 A AU 7300698A AU 7300698 A AU7300698 A AU 7300698A
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alkyl
substituted
radicals
cycloalkyl
group
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AU73006/98A
Inventor
Werner Bonin
Ralf Braun
Harald Jakobi
Manfred Kern
Gerhard Krautstrunk
Martin Markl
Ulrich Sanft
Wolfgang Schaper
Herbert Stark
Marie-Theresia Thonessen
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Bayer CropScience AG
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Hoechst Schering Agrevo GmbH
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Publication of AU7300698A publication Critical patent/AU7300698A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

WO 98/22445 1 PCT/EP97/05887 QUATERNARY NITROGEN HETEROCYCLES, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS PESTICIDES The invention relates to novel substituted pyridines and pyrimidines and 5 condensed systems derived therefrom, processes for their preparation and 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 10 WO-A-93/19 050, DE-A-43 43 250, WO-A-95/07 890, WO-A-94/21 613). However, the biological activity of these compounds, in particular at low application rates and concentrations, is not satisfactory in all use examples. 15 Novel, positively charged nitrogen heterocycles of the formula I have been found x R3() 20 A 1 n R2 D Ri in which the radicals and groups are as defined below, 25 which, while showing good tolerance by plants and favorable toxicity in 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. 30 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 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, (C-C 4 )-alkyl, (Cl-C 4 )-haloalkyl or 20
(C
3
-C
5 )-cycloalkyl; (4) R 2 and R 3 are identical or different and are each hydrogen, (C0-04) 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-(C 1
-C
8 )-alkylsilylalkynyl, (Cl-C4) alkoxy, (Cl-C 4 )-haloalkoxy, (C1-C 4 )-alkoxy-(C 1
-C
4 )-alkyl, (Cl C 4 )-haloalkoxy-(C-C 4 )-alkyl, (Cl-C 4 )-alkoxy-(C C4) haloalkyl, (Cl-C 4 )-haloalkoxy-(Cl-C 4 )-haloalkyl, amino, monosubstituted amino, disubstituted amino, halogen, 30 hydroxyl, (Cl-C 4 )-hydroxyalkyl, (Cl-C 4 )-alkanoyl, (Ci C4) alkanoyl-(Cl-C 4 )-alkyl, (Ci-C 4 )-haloalkanoyl,
(C
3
-C
5 )-cyclo alkyl, (C 3
-C
5 )-halocycloalkyl, cyano, (Ci-C 4 )-cyanoalkyl, nitro, (Ci-C 4 )-nitroalkyl, thiocyano, (Cl-C 4 )-thiocyanoalkyl, (C C4) alkoxycarbonyl, (Ci C 4 )-alkoxycarbonyl-(Cl-C 4 )-alkyl, 3 (Cl-C 4 )-haloalkoxycarbonyl, (Cl-C 4 )-alkylthio, (Cl-C 4 )-alkyl thio-(Cl-C4)-alkyl, (Cl-C4)-haloalkylthio, (Cl-C4)-alkylsulfinyl,
(C-C
4 )-haloalkylsulfinyl,
(C-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 (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, preferably trifluoromethyl, halogen, (Cl -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-, 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 (Cl-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 (Cl-C 4 )-alkyl, (6) Y - Z together are a (Cl-C2 0 )-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 R 10 is hydrogen, (Cl-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 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
(C-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-(Cl-C 4 )-alkoxy, hydroxyl and 10
(C-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
2 -C)-alkyl, (C2-C4)-alkenyl, 20 (C 3
-C
7 )-alkynyl, (C3-C7)-cycloalkyl,
(C
3
-C
7 )-cycloalkenyl, halogen, halo-(Cl-C 4 )-alkyl, 25 halo-(Cl-C4)-alkoxy, hydroxyl and (Cl-C4)-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 -0 8 )-cycloalkenyl, phenoxy, 5 substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, 10
NO
2 , 0 11 -C-R13 acetoxy, 15 hydroxyl, cyano, SiR 14
R
15
R
16 , 0-SiR 14
R
1 5
R
6 ,
NR
17
R
18 20 S(O)R19,
SO
2 R19, (Cl-C12)-alkyl, (C2-C1 2 )-alkenyl, (Cl-C 12 )-alkoxy and 25 (Cl-C 12 )-alkylthio; and R1 3 is (C -Cy-alkyl, halo-(C-C 7 )-alkyl, (C 3
-C
7 )-cycloalkyl, halo-(C 3
-C
7 )-cycloalkyl, (CC 7 )-alkoxy, phenyl or substituted phenyl; 30 R 14 , R 15 and R 16 are identical or different and are each independently of one another (C-C 4 )-alkyl, phenyl and/or substituted phenyl;
R
1 7 and R 18 are identical or different and are each independently of the other hydrogen, (C 1
C
4 )-alkyl and/or 6 (Cl-C 4 )-acyl;
R
19 is (C-C 10 )-alkyl, phenyl or substituted phenyl; where in (C-C 1 2)-alkyl, (Cl-C 12 )-alkoxy, (C-C12)-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 ' or SiR 11
R
12 '; R10', R 11 ' and R 12 ' have the meanings of R 10 , R 11 , R 12 ; the (C1C1- 2 )-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-(Cl-C 4 )-alkoxy, hydroxyl,
(C
3 -0 8 )-cycloalkyl,
(C
3 -C)-cycloalkenyl, (Cl C4) 15 acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (C1C7) 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 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,)-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 (CrCy)-alkyl, (C2-C4)-alkenyl,
(C
3
-C
7 )-alkynyl, (C3-C7)-cycloalkyl, 7
(C
3 -Cy)-cycloalkenyl, halogen, halo-(C 1
-C
4 )-alkyl, halo-(C 1
-C
4 )-alkoxy, 5 hydroxyl and (Cl-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 -Cs)-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 (CrC18)-alkyl,
(C
3 -C)-cycloalkyl,
(C
3
-C
8 )-cycloalkoxy, (C2-C1 8 )-alkenyl, 20
(C
2
-C
18 )-alkynyl, (CrC12)-alkoxy, (Cl-C 12 )-alkanoyloxy, formyl, (C2-C1 2 )-acyl, 25 (Cl-C1 2 )-alkyl-oxycarbonyl, SiR 2 1
R
22
R
2 3 , N24R25, 0 30 C-NR2R hydroxyl, halogen, aryl, heteroaryl, 8 O aryl, o heteroaryl,
CH
2 0 aryl,
CH
2 0 heteroaryl, 5
(C
1 -0 1 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 (C1-018)-, (C2-C18)-, (C1-C12)-, (C2-C12)- and 10 (C 1 -0 1 3 )-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as 0, NR 10 " or SiR' 1
"R
12 , these hetero atom radicals preferably not being adjacent to one another, where R 10 ", R 11 " and R 12 " have the meanings of
R
10 , R 11 , R 1 2 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, (Ci1 8 )-alkoxy,
(C
3
-C
8 )-cycloalkyl and aryl, where in the (C 1
-
1 )-hydro carbon radicals more than one, preferably up to three, 9 nonadjacent 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 5 together to form a cycle, the silicon atom in this case being a ring atom of this cycle, and where additionally these (C0-018) 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 10 from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the cycloalkyl or cycloalkenyl radicals defined under (10) may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units 15 are in the 1,4 position, preference is given to the cis configuration; or (11) Y is a bond; and 20 (12) Z (a) is a group of the formula l1
X
1 Ry 25 where X 1 independently of the other is sulfur or oxygen; Rz is hydrogen,
(C
1
C
4 )-alkyl, trifluoromethyl or (C1C4) alkoxy; or RY is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the 30 aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up 10 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 1
-C
4 )-alkyl, 5 (C 1
-C
4 )-alkoxy or (C 1
-C
4 )-alkanoyl and 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 mentioned above, may form a cycle and where these 10 hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, 15 aryloxy, arylthio, cycloalkoxy, cycloalkylthio, hetero cyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxy carbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, 20 cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkyl 25 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 30 number) identical or 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 X1 and where one or two CH 2 groups, preferably one CH 2 group, may be 11 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, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be 5 unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by RY and Rz may be unsubstituted or substi tuted by up to three, but preferably one, substituents 10 and where these substituents are identical or different and are each alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or 15 alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where 20 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 tetrahydronapthalene, decalin or benzocycloheptane system, and where the benzene ring in these 25 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; 30 in particular those groups of the formula 11 where RY is (Cl-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 (in the case of fluorine up to 12 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 5 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, (C-C 4 )-alkoxy or (Cl-C 4 )-alkanoyl and R 27 and R 28 , are each (C0-C 4 )-alkyl, preferably methyl, 10 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 with or without the variations mentioned may be substituted by one or more, preferably up to three (in 15 the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, (C3-C8) cycloalkoxy, (C 3
-C
8 )-cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (Cl-C1 2 )-alkanoyl, 20
(C
3
-C
8 )-cycloalkanoyl, (C2-Cl2)-haloalkanoyl, aroyl, aryl-(C 1
C
4 )-alkanoyl,
(C
3
-C
8 )-cycloalkyl-(C 1
C
4
)
alkanoyl, heterocyclyl-(Cl-C 4 )-alkanoyl, (C1 C12) alkoxycarbonyl, (Cl-C 12 )-haloalkoxycarbonyl, (C3-C8) cycloalkoxycarbonyl,
(C
3
-C
8 )-cycloalkyl-(C 1 C4) 25 alkoxycarbonyl, aryl-(C-C 4 )-alkoxycarbonyl, heterocyclyl-(Cl-C 4 )-alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl,
(C
1
-C
12 )-alkanoyloxy,
(C
2
-C
12 )-haloalkanoylalkoxy,
(C
3 -C,)-cycloalkanoyl oxy, (C 3
-C
8 )-cycloalkyl-(Cl-C 4 )-alkanoyloxy, aroyloxy, 30 aryl-(Cl-C 4 )-alkanoyloxy, heterocyclyl-(Cl C4) alkanoyloxy, (Cl-C1 2 )-alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be 13 unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where RY and Rz together form a three- to eight 5 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 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 10 is hydrogen,
(C
1 -C)-alkyl, (0 1
-C
8 )-alkoxy, (C1C8) 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 15 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 (C 1
C
8 )-alkyl, (C1C8) 20 haloalkyl,
(C
1
C
8 )-alkoxy, (C-C,)-alkylthio, (C3-08) cycloalkyl, (C 3 -C)-cycloalkoxy, (C 3
-C
8 )-cycloalkylthio, aryl, aryloxy, arylthio, aryl-(C-C4)-alkyl, aryl-(Cl C4) alkoxy, aryl-(C 1
C
4 )-alkylthio, heterocycyl, heterocyclyloxy, heterocyclylthio, (C -C 8 )-trialkylsilyl, 25 preferably (Cl C 8 )-alkyldimethylsily, or (C, C-) 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 30 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-tetrahydronapthalene, decahydro- 14 naphthalene 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 5 different substiuents, where among the compounds where the carbon atom between the hetero atoms X 1 carries only the substituent RY, the substituents X and RV are preferably cis to each other; 10 Rz is hydrogen, (Cl-C 4 )-alkyl, trifluoromethyl or (C1C4) alkoxy; or (b) is a group of the formula IlIl y3 15
(Y
2 )m(Z-R)n where 20 Yi, Y 2 and Y 3 independently of one another are each a group of the formula -0-, -CO-, -CNR 3 0-, -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 3 1R 32 ; or Y' or Y 3 stands in place of a direct bond, 25 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) haloalkynyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, (Cl-C 4 )-alkylthio,
(C,-C
4 )-haloalkylthio, (C, C4) 30 alkanoyl, (C 2
-C
4 )-haloalkanoyl, (C 3
-C
5 )-cycloalkyl, (Cl-C 4 )-alkylsulfonyl, (Cl-C 4 )-haloalkylsulfonyl, (C, C 4 )-alkoxy-(C1 C 4 )-alkyl, (Cl-C 4 )-alkoxycarbonyl;
R
3 1 and R 32 independently of the other are each hydrogen, hydroxyl, halogen, cyano, (C, C 4 )-alkyl, (C,-C 4 )-halo- 15 alkyl, (C 2
-C
4 )-alkenyl,
(C
2
-C
4 )-haloalkenyl, (C2-04) alkynyl, (C 2
-C
4 )-haloalkenyl, (C 3
-C
5 )-cycloalkyl, (C0-C 4 )-alkanoyl, (Cl C 4 )-haloalkanoyl, (Cl-C4)-alkoxy,
(C-C
4 )-haloalkoxy, (Cl-C4)-alkylthio or (Cr-C4) 5 haloalkylthio; mi is 0, 1, 2, 3 or 4, preferably 1 or 2; n 1 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, S020, NR 34
SO
2 , S0 2
NR
35 , SiR 36
R
37 or 10 U-C-V, 11 W where
R
36 and R 37 are each (Cl-C 4 )-alkyl or phenyl, preferably 15 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
R
33 , R 34 , R 35 , R 38 and R 39 are identical or different and are 20 each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl; Rq are substituents which are independent of one another and each is halogen, cyano, nitro, (C 1
C
20 )-alkyl,
(C
2
-C
20 )-alkenyl, (C 2 -C2 0 )-alkynyl, (C 3
-C
8 )-cycloalkyl,
(C
4
-C
8 )-cycloalkenyl, where in the last 5 radicals one 25 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 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 30 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 16 case of fluorine up to the maximum number) identical 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 5 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, (C0-C 4 )-alkyl and oxo, or 10 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, 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 15 NR where
R
40 is hydrogen, (C 1
C
4 )-alkyl, (Cl C 4 )-alkoxy or (C1C4) alkanoyl;
R
4 ' and R 42 independently of the other are each (C1C4) 20 alkyl, preferably methyl; D' and D 2 are independent of each other and each is a direct bond, oxygen, S(O)k, S0 2 0, OS 0 , 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 25 R 46 independently of the others is hydrogen, (Cl-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) alkyl;
R
43 and R 44 independently of the other are each hydrogen, 30 cyano, nitro, halogen, (C C)-alkyl, (C -C 8 )-haloalkyl,
(C
2 -C)-alkenyl, (C 2
-C
8 )-haloalkenyl, (C 2
-C
8 )-alkynyl,
(C
2 -C,)-haloalkynyl, (C1-C,)-alkoxy-(C 1
-C
4 )-alkyl, (C-C)-haloalkoxy-(ClC 4 )-alkyl, (Cl-C8)-alkylthio (ClrC4)-alkyl, (Cl-C8)-haloalkylthio-(ClrC4)-alkyl, 17
(C
3 -C)-cycloalkyl,
(C
4
-C
8 )-cycloalkenyl,
(C
3
-C
8
)
cycloalkyl-(C-C 4 )-alkyl, (C 4
-C
8 )-cycloalkenyl-(C-C4) alkyl, aryl, heterocyclyl, aryl-(C-C4)-alkyl or heterocyclyl-(C-C 4 )-alkyl, where in the last 8 radicals 5 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 , or
R
43 and R 44 located at the same carbon atom together are 10 an oxo group, where
R
49 is (C 1
-C
4 )-alkyl, (C-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro or halogen;
R
45 is hydrogen, (C-C)-alkyl,
(C
1
C
4 )-haloalkyl, (C1C4) 15 alkoxy, (C 1
C
4 )-alkylthio, (C 3 -C)-cycloalkyl, (C2-C4) alkenyl, (C 2
-C
4 )-alkynyl, (Cl C 4 )-alkanoyl,
(C
2
-C
4
)
haloalkanoyl, (C 2
-C
4 )-alkoxyalkyl, phenyl-(CC 4 )-alkyl or phenyl where the phenyl groups may be unsubstituted or substituted by up to three (in the case 20 of fluorine up to the maximum number) identical or different substituents R 50 , where
R
50 is (C 1
C
4 )-alkyl, (C 1
C
4 )-haloalkyl, (C-C 4 )-alkoxy, (CrC 4 )-alkylthio, halogen or cyano; or, if not included in the above definitions, 25 (c) is a group of the formula IV
V
4
W
1 -RO Z2<Ru (IV) 30 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 system, where 18 Ru is hydrogen, halogen, cyano, (C 1
C
4 )-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,
(C
1
C
4 )-alkoxy, (Cl-C 4
)
5 haloalkoxy, (Cl-C 4 )-alkanoyloxy, (Cl-C 4 )-haloalkanoyl oxy, (Cl C 4 )-alkylthio or (Cl-C 4 )-haloalkylthio;
W
1 is a direct bond, oxygen, -NR 52 -, -00-, -COo-,
CONR
52 -, sulfur, -C=N-, -C=N-0- or -NR520-; Rt is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or 10 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 15 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 20 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 25 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 where 30 R 51 is hydrogen, (Cl-C 4 )-alkyl, (C-C 4 )-haloalkyl, (C2-C4) alkenyl, (C 2
-C
4 )-haloalkenyl,
(C
2
-C
4 )-alkynyl, (C2-C4) haloalkynyl, (Cl C 4 )-alkoxy, (Ci-C 4 )-alkanoyl, (C2-C4) haloalkanoyl, (Cl C 4 )-alkoxy- (Cl-C 4 )-alkyl, (C C4) alkylthio-(Cl-C 4 )-alkyl, (C-C 4 )-alkoxycarbonyl, 19 (Cl-C 4 )-alkylsulfonyl, (Cl-C 4 )-haloalkylsulfonyl, phenylcarbonyl, phenyl-(C-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 5 maximum number) identical or different substituents R 5,'or
R
51 is CONR 60
R
61 where
R
60 and R 61 independently of the other are each hydrogen,
(C
1
C
4 )-alkyl or phenyl, where the phenyl group may 10 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 (C1C4) alkyl, (Cl-C4)-haloalkyl, (Cl-C4)-alkoxy, (Cl-C4) 15 haloalkoxy, (Cl-C 4 )-alkylthio or halogen;
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-C 4 )-alkoxy or (C1C4) alkanoyl; 20
R
54 and R 55 independently of the other are (C 1
-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 25 of fluorine up to the maximum number) identical or different substituents R 63 ; R63 may be (C 1 -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 30 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 system, preferably the indane, 1,2,3,4- 20 tetrahydronapthalene, 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 5 number) identical or different substituents D 6
R
6 s, 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, S0 2 0, OS0 2 , CO, OCO, COO, SO 2 NR66 , NR 66 S0 2 , NR 66 0, ONR 66 , 10 NR 66 , NR 6CO, CONR 66 or SiR 67
R
68 , where k = 0, 1 or 2; and
R
56 , R 57 , R 64 and R 65 independently of one another are each hydrogen, cyano, nitro, halogen, (CrO0)-alkyl, (Cl-C,)-haloalkyl, (C 2 -C)-alkenyl, (C 2 -C,)-haloalkenyl, 15 (C 2
-C
8 )-alkynyl, (C 2
-C
8 )-haloalkynyl, (Cl C 8 )-alkoxy (Cl-C 4 )-alkyl, (Cl-C 8 )-haloalkoxy-(Cl-C 4 )-alkyl, (Cl-C 8 )-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 20 (Cl-C 4 )-alkyl, aryl, heterocyclyl, aryl-(Cl-C 4 )-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 25 number) identical or different substituents R 69 , where
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 68 independently of the other are each (C0-04) alkyl, and 30 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, (Cl-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 21 atom together, and in each case independently of the others, are an oxo group; in particular those groups of the formula IV where 5 Rt is hydrogen, (C -C,)-alkyl,
(C
2
-C
8 )-alkenyl,
(C
2
-C,)
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 10 such as oxygen, S(O)x where x = 0, 1 or 2, NR 53 or SiR 5 4
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 15 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 the case of fluorine up to the maximum number) identical or different radicals D 4
R
57 , or 20 Ru and Rt together form a five- or six-membered ring system 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 25
NR
58 , where
R
53 is hydrogen, (Cl-C4)-alkyl,
(C
1
C
4 )-alkoxy or (C1C4) alkanoyl and
R
54 and R 55 independently of the other are (Cl-C 4 )-alkyl, preferably methyl; 30
R
58 is hydrogen, (0 1
-C
8 )-alkyl, (C-C,)-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 22 R63 may be (CC-0 4 )-alkyl, (Cl-C 4 )-haloalkyl, (C1C4) alkoxy, (C-C4)-haloalkoxy, cyano, nitro or halogen, and the ring system formed by Ru and Rt may be unsubstituted or substituted by up to three, but 5 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 tetrahydronapthalene, decalin or benzocycloheptane 10 system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D Res, where in the compounds where the carbon atom 15 between Y 4 and Z 2 where Y = CH 2 only carries the substituent Wl-Rt, 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, 20 OCO, COO, S0 2
NR
66 , NR 66 SO NR660, ONR66,
NR
66 , NR 66 CO or CONR 66 , and k = 0, 1 or 2,
R
66 independently of the others is hydrogen, (C-C 4 )-alkyl,
(C-C
4 )-alkanoyl or (C 3
-C
5 )-cycloalkyl and
R
56 , R 57 , R 64 and R 65 independently of one another are each 25 hydrogen, cyano, nitro, halogen, preferably fluorine, (Cl-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 substituted by up to three (in the case of fluorine up to 30 the maximum number) identical or different substituents R 69 , where
R
69 independently of the others may be (CC-0 4 )-alkyl, (Cl
C
4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl C 4 )-haloalkoxy, cyano, nitro, halogen, or two of the radicals 23
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; 5 (13) R 4 and R 5 are identical or different and are each hydrogen, halogen,
(C
1
C
20 )-alkyl with or without substitution, (C 2 -C2 0 )-alkenyl with or without substitution, (C 2 -0 20 )-alkynyl with or without substitution, aryl, substituted aryl or (C 3
-C
8 )-cycloalkyl with or without substitution; 10 (14) E is oxygen, NR 70 , S(O)q where q = 0, 1 or 2, R 70 being hydrogen, (Cl-C 4 )-alkyl, (C 1
C
4 )-alkenyl or (C 1
C
4 )-acyl; (15) R 6 is (C 1
-C
20 )-alkyl, (C 2 -C2 0 )-alkenyl, (C 2 -C2 0 )-alkynyl, (C0-C20) 15 M || haloalkyl, (C 3
-C
8 )-cycloalkyl, aryl or -C-R 71 , where M is oxygen or sulfur and R 71 is (C 1
C
20 )-alkyl, (C 2
-C
20 )-alkenyl,
(C
2
-C
20 )-alkynyl, aryl, heterocyclyl, (Cl C 20 )-haloalkyl, 20 (C 2 -C2 0 )-haloalkenyl, (C 2
-C
20 )-haloalkynyl, (C 3
-C
8 )-cycloalkyl,
(C
3 -C)-halocycloalkyl,
(C
5
-C
8 )-cycloalkenyl, (C 5
-C
8
)
halocycloalkenyl and where, if not included in the definitions above, in the (C1C20)- and (C 2
-C
20 )-hydrocarbon radicals mentioned under (13) and (15) one or more, preferably up to 25 three, nonadjacent CH 2 groups may be replaced by a carbonyl group or by hetero atom radicals such as 0, S(0)x where x = 0, 1 or 2, NR 1 O'" or SiR'R 12 ", where R 10 ', R 1 ' and R 12 "' have the meanings of R 10 , R 11 and R 12 and where additionally 3 to 6 carbon atoms of these hydrocarbon 30 radicals may form a cycle and where these hydrocarbon radicals with or without the abovementioned 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 35 hydroxyl, alkyl, halogen, haloalkyl, cycloalkyl, acyl, phenoxy, 24 substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio and NR 72
R
73 , where aryl is as defined under (8), where the heterocyclyl radicals listed may be unsubstituted or substituted by up to three (in the case of 5 fluorine up to the maximum number) identical or different radicals and where R 72 and R 73 independently of the other are each hydrogen,
(C
1
-C
8 )-alkyl, (C 2
-C
8 )-alkenyl, (C1-C8) acyl, aryl, heteroaryl or benzoyl; or 0 10 7 1 7 (16) if E is NR 0 and R 6 is -C-R 71 ,
R
70 and R 71 together are also (C 3
-C
6 )-alkanediyl, where a CH 2 group adjacent to the nitrogen may be replaced by CO and/or where ethanediyl may be replaced by ethenediyl or 15 o-phenylene, preferably
(C
3
-C
6 )-alkanediyl,
-CO-CH
2
-CH
2 -, -CO-CH=CH- or -c . 20 An inorganic anion is an anion of an inorganic acid, for example F, CL-, Br, I~, NO3, SO 4 2 -, HSO4, P0 4 3 -, HP0 4 2 ~, H2PO4-, PO33- or
N
3 ~, or a complex anion, for example BF 4 -, PF 6 ~ or tetraphenylborate. 25 An organic anion is an anion of an organic acid (carboxylic acid, sulfonic acid, phosphonic acid and the like) or an aromatic or heteroaromatic phenol-like compound. These are, for example, anions of mono- or bifunctional carboxylic acids and hydroxy 30 carboxylic acids such as acetic acid, propionic acid, maleic acid, succinic acid, glycolic acid, oxalic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and sulfonic acids such as p-toluenesulfonic acid, dodecylsulfonic acid or 1,5-naphthalenedisulfonic acid, or saccharine.
25 If A and D are part of a pyrimidine system, it is assumed that A is nitrogen and D is N*R. However, it cannot be excluded with absolute certainty that the radical R is in position 3 (i.e. that A is N*R and D is nitrogen). 5 If Z is (C 3 -C.)-cycloalkyl or (C 5
-C
8 )-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,
(C
3 -C)-cycloalkyl,
(C
3
-C
8 )-cycloalkyl-(Cl-C 4 )-alkyl, (C-C)-alkoxy, 10
(C
3 -C)-cycloalkoxy, (C1-C 4 )-alkoxy-(C 1
-C
4 )-alkyl, (C 3
-C
8 )-cyclo alkyl-(Cl-C 4 )-alkoxy, tri-(Cl-C 8 )-alkylsilyl, preferably dimethyl (Cl -C,)-alkylsilyl or triethylsilyl, di-(Cl -C 8 )-alkyl-(C 3
-C
8 )-cycloalkyl silyl, preferably dimethylcyclohexylsilyl, di-(0 1
-C
8 )-alkyl-(phenyl (Cl-C 4 )-alkyl)-silyl, preferably dimethyl-(phenyl-(Cl-C 4 )-alkyl)-silyl, 15 di-(Cl -C 8 )-alkyl-(Cl
-C
4 )-haloalkylsilyl, preferably dimethyl-(Cl
-C
4
)
haloalkylsilyl, dimethylphenylsilyl,
(C
1
-C
4 )-haloalkyl, halogen,
(C
1
-C
4 )-haloalkoxy, heteroaryl, phenyl, phenyl-(Cl-C 4 )-alkyl, benzyloxy, benzyloxy-(Cl-C 4 )-alkyl, benzylthio, phenylthio and phenoxy, where heteroaryl or phenyl in the last eight radicals may 20 be unsubstituted or substituted by one or two substituents, these substituents being identical or different and being in each case
(C
1
C
8 )-alkyl, (C 3
-C
8 )-cycloalkyl, (Cl-C 4 )-haloalkyl, preferably trifluoromethyl, halogen, (Cl-C 4 )-dialkylamino,
(C
1
-C
4 )-alkylthio,
(C-C
8 )-alkoxy, (Cl-C 4 )-haloalkoxy, (C1-C 4 )-alkoxy-(Cj-C 4 )-alkoxy, 25 H 5
C
2 -0-[CH 2
-CH
2 -0-]x, 2-(tetrahydro-2H-pyran-2-yloxy)ethoxy,
(C
2 -C)-alkenyl,
(C
2
-C
8 )-alkynyl, benzyloxy, which may carry one or two identical or different substituents selected from the group consisting of (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy and halogen in the phenyl moiety, tri-(Cl-C 4
)
30 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. Preference is given to compounds of the formula I 26 in which A is CH and D is N*R 5 or A is nitrogen and D is N*R; Qn- is an inorganic or organic anion such as Hal, N0 3 ~, BF4~, BPh 4 ~ or 10 PF
R
1 is hydrogen, methyl, fluorine or chlorine;
R
2 and R 3 are each hydrogen,
(C-C
4 )-alkyl, (C 2
-C
4 )-alkenyl, (C2-C4) alkynyl, amino, (Cl-C4)-alkylamino, (Cl-C 4 )-dialkylamino, trimethyl silylethynyl, methoxycarbonyl, (Cl C 4 )-haloalkyl, (C2-C4) 15 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 unit; or 20 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. 25 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-C 4 )-alkyl radical; and Z is (C 3
-C
8 )-cycloalkyl or (C 5
-C
8 )-cycloalkenyl, where a CH 2 group of 30 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 number), identical or different radicals selected from the group 27 consisting of (Cl-C18)-alkyl,
(C
3
-C
8 )-cycloalkyl, 5 (C 3
-C
8 )-cycloalkoxy,
(C
2
-C
1 ,)-alkenyl, (C2-C18 )-alkynyl, (CgC12)-alkoxy, (Cl-C1 2 )-alkanoyloxy, 10 formyl, (C2-C1 2 )-acyl, (C1 -C1 2 )-alkyl-oxycarbonyl, SiR 2 1 1R 22
R
23 ,
NR
2 4
R
25 , 15 0
C-NR
24
R
25 , hydroxyl, halogen, 20 aryl, heteroaryl, o aryl, o heteroaryl,
CH
2 0 aryl, 25
CH
2 heteroaryl, (Ci-C18 )-alkanediyldioxy, (C1-C1 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 30 in the (C1-C18)-, (C2-C18)-, (C1-C12)-, (C2-C12)- and (C1-C13) hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as 0, NR 1 O" or SiR 11
"R
12 , these hetero atom radicals preferably not being adjacent to one another, where R 10 ", R'1" and
R
12 " have the meanings of R 10 , R 11 , R 12 and where additionally 3 to 28 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 5 radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio; where heteroaryl may be unsubstituted or substituted by up to three 10 (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, 15 (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 1
-C
18 )-alkyl, (C-C 18 )-alkoxy, (C 3 -C,)-cycloalkyl and aryl, where in the (Cl-C 1 8 )-hydrocarbon radicals more than one, preferably up to three, CH 2 groups may be replaced by oxygen and 20 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-Cl 8 )-hydrocarbon radicals with or without the 25 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 (C5-C8) cycloalkenyl radicals defined above may be cis or trans with respect 30 to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1,4 position, preference is given to the cis configuration; or Y is a bond; and 29 Z (a) is a group of the formula il X1 Ry 5 X1 Rz where X 1 is oxygen; RY is (C0-C 20 )-alkyl, (C 2
-C
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 10 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 (C 1
C
4 )-alkyl, preferably methyl, 15 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 20 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 25 unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different 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 30 replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 orNR where R 29 is hydrogen, (C 1
C
8 )-alkyl, (C 1
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 30 to the maximum number) 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 (Ci 5
C
8 )-alkyl, (C 3 -C,)-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, 10 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-tetrahydronapthalene, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to 15 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 20 Rz is hydrogen or (b) is a group of the formula (Ill) '_ y 3 25 (2 ( Z' - Rq ) n' ii where Yl, Y 2 and Y 3 are each a group of the formula -O-, -S(O)r-, where 30 r = 0, 1 or 2 or is a group of the formula CR31 R 32 , or Y' or y3 stand in place of a direct bond, where R31 and R 32 independently of the other are each hydrogen or methyl; mi is 1 or 2; 31 ni is 1 or 2;
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, where II 5 W U is a direct bond, NR 38 or 0; W is oxygen; V is a direct bond, NR 39 or oxygen; and 10 R 36 and R 37 are each (C-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, (C 1
C
4 )-alkyl, (Cl-C 4 )-alkoxy, (C-C 4 )-alkanoyl or
(C
3 -Cs)-cycloalkyl; Rq independently of the others is (Cl-C 8 )-alkyl where one or 15 more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen and which, with or without the variations mentioned, may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D 1
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 ;
D
1 and D 2 are independent of one another and are each a direct 25 bond, -0-, -S(O)k-, -SO20-, -OS0 2 -, -CO-, -OCO-, -Coo-,
-NR
4 6 -, -S0 2
NR
46 -, -NR 46 SO2-, -ONR46-, -NR460.
-NR
46 CO-, -CONR 46 -, and k = 0, 1 or 2, and where
R
46 independently of the others is hydrogen, (C 1
C
4 )-alkyl, (Cl C 4 )-alkanoyl or (C 3
-C
5 )-cycloalkyl; 30 R 43 and R 44 independently of the other are each hydrogen, halogen, 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 32 maximum number) identical or different substituents R 49 where
R
49 independently of the others may be (C 1
-C
4 )-alkyl, (C1-C4) haloalkyl, (C1-C 4 )-alkoxy, (C1-C4)-haloalkoxy, cyano, nitro, 5 halogen; or, (c) is a group of the formula IV Y4 Wi-Rt 10 10 ZK Ru (IV) where 15
Y
4 is a direct bond or CH 2 ;
Z
2 is oxygen; Ru is hydrogen, (C 1
-C
4 )-alkyl, tirfluoromethyl or (C 1
-C
4 )-alkoxy;
W
1 is a direct bond, oxygen, -CO-, -C00-, CONR 52 , sulfur, -C=N-, -C=N-0- where R 52 is hydrogen, (C 1
-C
4 )-alkyl, 20 (C-C 4 )-alkanoyl and (C 3
-C
5 )-cycloalkyl, and Rt is as defined above under (12 c). Particular preference is given to compounds of the formula I, in which
R
1 is hydrogen; 25 R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3) alkenyl, amino, (Cl C 4 )-alkylamino, (Cl C 4 )-dialkylamino, (C2-C3) 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 30 the quinazoline or quinoline system, which may be fluorine substituted in the carbocyclic moiety; or
R
2 and R 3 together with the carbon atoms to which they are attached form a saturated 6-membered ring, which may contain an oxygen or sulfur atom instead of a CH 2 group; 33 in particular those compounds where
R
1 is hydrogen;
R
2 is methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (C 1
-C
2 )-fluoroalkyl 5 or methoxymethyl;
R
3 is fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C-C 2 )-fluoro alkyl, amino, (Cl C 2 )-alkylamino, (C1-C 2 )-dialkylamino or methoxy; or, in the case that A is nitrogen,
R
2 and R 3 form, together with the ring system to which they are attached, 10 the quinazoline system, which may be substituted by one fluorine atom. Likewise, particular preference is given to compounds of the formula 1, in which 15 X is NH; Y is a bond; and Z (a) is cyclopentyl or cyclohexyl, where both radicals may be substituted as above under (10) and where, in the case of cyclohexyl, 1,4-substitution is preferred, the substituents 20 being cis to one another; or (b) is a group of the formula 11 X R 25 (I X RZ where
X
1 is oxygen; Rz is hydrogen; 30 or (c) is a group of the formula Ill
Y
3
Y
1 34 where Y1 is CH 2 ;
Y
2 is CH2;
Y
3 is CH 2 , 0 or a direct bond; 5 mi is 1 or (d) is a group of the formula IV y4 W1-Rt 10 Z RU (IV) where Y4 is a direct bond or CH 2 ; z2 is oxygen; 15 Ru is hydrogen or methyl; in particular those compounds where Z (a) is cyclohexyl which is preferably substituted by a radical 20 selected from the group consisting of (Ci-C)-alkyl,
(C
3
-C
8 )-cycloalkyl,
(C
3 -C)-cycloalkoxy,
(C
2
-C
8 )-alkenyl, 25 (C 2
-C
8 )-alkynyl, (Ci-C)-alkoxy, (C1 -C 8 )-alkyloxycarbonyl, SiR 21
R
22
R
23 , 0 30 1 42 -C-NR24R25 aryl, heteroaryl, 0 aryl, 35 0 heteroaryl, 35
CH
2 0 aryl,
CH
2 0 heteroaryl, (C0-c 8 )-alkanediyldioxy and
(C
1
-
3 )-alkyloximino, where this substituent is in position 4 5 of the cyclohexyl ring and cis with respect to the -(X-Y)- unit and where, if not included in the definitions above, one or more, preferably up to three, CH 2 groups in the (C1C8)-,
(C
2 -C)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals, such as 0, or SiR'l'R 1 2 ", where R"' 10 and R 12 " have the meanings of R 1 1 , 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 the variations may be substituted by one or more, preferably up to three (in the case of halogen up 15 to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl; heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical 20 or different substituents; aryl is as defined under (8);
R
24 and R 25 are identical or different and independently of one another are each hydrogen, (C 1
C
4 )-alkyl, phenyl and substituted phenyl, and R 21 , R 22 , R 23 are identical or different 25 and independently of one another are each (C-C)-alkyl, (C-C)-alkoxy, (C 3 -C)-cycloalkyl and aryl, where in the (C0-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 30 cycle, it being possible for the silicon atom to be part of this cycle, and where additionally these (C 1
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 36 consisting of halogen, haloalkyl, cycloalkyl; or (b) is a group of the formula (11) X RY 5 X RZ where
X
1 is oxygen; 10 Rz is hydrogen; RY is (C 1
-C
15 )-alkyl, aryl or heterocyclyl meaning a hetero 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 15 number) identical or different radicals and where in the alkyl radical mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and where additionally 3 to 8 atoms of this alkyl 20 radical, which may be modified as above, may form a cycle, and where this alkyl radical with or without the variations mentioned may be substituted by one or more halogen atoms (in the case of fluorine up to the maximum number of identical or different 25 substituents), and where the substituents X and RY on the heteroaliphatic six-membered ring are preferably cis to one another; or (c) is a group of the formula (Ill) 30 - y 3 where (Z - R )n where 37 ni is 1 or 2; 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 5 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 1
R
43 , or Rq is aryl or heterocyclyl, where these two radicals may 10 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 (d) is a group of the formula IV 15 4 W1Rt Ru (IV) where 20 Ru is hydrogen; Rt is (C-C,)-alkyl in which one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and which with or without the variations mentioned may be substituted by one or 25 more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D3R56,'or Rt may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in 30 the case of fluorine up to the maximum number) identical or different radicals D 4
R
57 Furthermore, particular preference is given to compounds of the formula I in which 38 A is CH and D is N*R or A is nitrogen and D is N*R; 5 Q"~ is an inorganic or organic anion such as Hal-, NO 3 ~, BF 4 , BPh4~,
PF
6 ;
R
4 is hydrogen, halogen or methyl;
R
5 is hydrogen, halogen, (C 1
C-
8 )-alkyl, (C 2
-C
8 )-alkenyl, (C 2
-C
8 )-alkynyl, phenyl, substituted phenyl or (C 3
-C
8 )-cycloalkyl; 10 E is oxygen, NR 70 , S(O)q where q = 0, 1 or 2, where R 70 is hydrogen, methyl or acetyl;
R
6 is (C-C4)-alkyl, (C 2
-C
4 )-alkenyl, (Cl-C 4 )-haloalkyl, (C 3
-C
6 )-cyclo M 15 || alkyl, phenyl or -C-R 71 , where M is oxygen or sulfur and R 7 1 is (Cl-C 8 )-alkyl, (C 2
-C
8 )-alkenyl, (C 2
-C
8 )-alkynyl, aryl, heterocyclyl,
(C
1 C-)-haloalkyl, (C 2
-C
8 )-haloalkenyl,
(C
2
-C
8 )-haloalkynyl, (C3-C6) cycloalkyl, (C 3
-C
6 )-halocycloalkyl,
(C
5
-C
6 )-cycloalkenyl, (C5-C6) 20 halocycloalkenyl and where the hydrocarbon radicals mentioned may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of alkyl, haloalkyl, cycloalkyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl and NR 72
R
73 , where aryl is as defined under (8), 25 where the 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 R 72 and R 73 independently of the other are each hydrogen, (C 1
C
8 )-alkyl,
(C
2
-C
8 )-alkenyl, (C 1
C
8 )-acyl, aryl, heteroaryl or benzoyl; or 30 0 (16) if E is NR 0 and Re is -C-R 71 ,
R
70 and R 71 together are also (C 3
-C
6 )-alkanediyl, where a CH 2 group adjacent to the nitrogen may be replaced by CO and/or 35 where ethanediyl may be replaced by ethenediyl or 39 o-phenylene, preferably (C 3
-C
6 )-alkanediyl, -CO-CH 2
-CH
2 -, -CO-CH=CH- or -C 5 Most particularly preferred are those compounds of the formula 1, in which
R
1 is hydrogen;
R
2 is ethyl or methoxymethyl; 10 R 3 is chlorine, bromine or methoxy, preferably those for which R 2 is ethyl and R 3 is chlorine; X is NH;
R
4 is hydrogen;
R
5 is hydrogen or (C 1
-C
8 )-alkyl; 15 E is oxygen or NR , where R 70 is hydrogen; M R- is -C-R 71 , where M is oxygen. 20 In the above formulae (1) to (IV), the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless specifically mentioned, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or, in the case of 25 unsaturated groups, 2 to 6 carbon atoms, are preferred for these radicals. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl radicals, hexyl radicals, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyl radicals, such as n-heptyl, 1 -methylhexyl and 30 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1 -yl, but-2-en-1 -yl, but-3-en-1 -yl, 1 -methylbut-3-en-1 -yl and 1-methylbut-2-en-1-yl; alkynyl is, for example, propargyl, but-2-yn-1-yl, 40 but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Cycloalkyl is a carbocyclic saturated ring system preferably having 3 8 carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl, but 5 also bicyclic systems, for example the norbornyl group or the bicyclo[2.2.2] octane radical and tricyclic systems, for example the adamantyl group. Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, 10 which are partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example monohaloalkyl, perhaloalkyl, CF 3 , CHF 2 , CH2F, 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 correspondingly 15 to haloalkenyl and other halogen-substituted radicals. A hydrocarbon radical is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic 20 hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl; preferably, a hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl; the same applies correspondingly to a hydrocarbon radical in a hydrocarbonoxy radical. 25 Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl. 30 A heterocyclic radical or ring (heterocycle) can be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, i.e. hetero atoms or ring members, including substituted hetero atoms, preferably selected from the group consisting of N, 0, S, SO, SO 2 ; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a 41 heteroaromatic radical having 5 or 6 ring atoms and it contains 1, 2 or 3 hetero units. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl), for example a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more 5 hetero atoms, in particular an aromatic system in which at least 1, preferably up to 4, in particular up to 2 CH are replaced by N and/or at least 1, preferably up to 3, -CH=CH units are replaced by NH, S or 0, adjacent oxygen atoms being excluded, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl 10 and imidazolyl, or it is a partially or fully hydrogenated radical such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Substituents which are suitable for a substituted heterocyclic radical are the substituents mentioned further below, and additionally oxo. The oxo group can also be present on the hetero ring 15 atoms, which can exist at various oxidation levels, for example in the case of N and S. Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl or heteroaryl, are, for example, a substituted radical derived 20 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 25 dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkyl sulfonyl and, in the case of cyclic radicals, also alkyl, cycloalkyl and haloalkyl; the term "substituted radicals" such as substituted alkyl etc. includes as substituents, in addition to the saturated hydrocarbon containing radicals mentioned, corresponding unsaturated aliphatic and 30 aromatic radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy, etc., with or without substitution. Preferred among the radicals having carbon atoms are those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms. Preferred substituents are generally selected from the group consisting of halogen, for example fluorine and chlorine, 42 (Cl-C 4 )-alkyl, preferably methyl or ethyl, (CC-0 4 )-haloalkyl, preferably trifluoromethyl, (C 1
-C
4 )-alkoxy, preferably methoxy or ethoxy, (Cl-C 4 )-haloalkoxy, nitro and cyano. Especially preferred are the substituents methyl, methoxy and chlorine. 5 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 10 monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; preference is given to alkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; acyl is defined as indicated further below and is preferably (Cl-C 4 )-alkanoyl. The same applies analogously to substituted hydroxylamino or hydrazino. 15 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-C 4 )-alkoxy, (C-C 4 )-haloalkyl, (C-C4) 20 haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyl radicals, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl. 25 An acyl radical is the radical of an organic acid, for example the radical of a carboxylic acid and radicals of acids derived therefrom, such as thiocarboxylic acid, iminocarboxylic acids with or without N-substitution, or the radical of carbonic monoesters, carbamic acid with or without N-substitution, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic 30 acids. Acyl is, for example, formyl, alkylcarbonyl such as [(C 1
C
4 )alkyl] 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 43 more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents already mentioned further above in general for substituted phenyl. 5 Furthermore, in the above formulae the term "dimethyl-(0 1
-C
8 )-alkylsilyl ethynyl" denotes, for example, the trimethylsilylethynyl or the tert-butyl dimethylsilylethynyl group; the term "(Cl-C 4 )-hydroxyalkyl" denotes, for example, the hydroxymethyl, 10 1 -hydroxyethyl, 2-hydroxyethyl, 1 -hydroxy-1 -methylethyl or the 1 -hydroxy propyl group; 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 15 radicals and, for example, the valeroyl, pivaloyl, hexanoyl, decanoyl or the dodecanoyl group; 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; 20 the term "(C 2
-C
12 )-haloalkanoyl" denotes a (Cl-C 20 )-alkanoyl group in which the hydrogen atoms are partly, in the case of fluorine partly or wholly, replaced by halogen atoms, preferably fluorine or chlorine; the term "cyano-(C 1
-C
4 )-alkyl" denotes a cyanoalkyl group whose hydrocarbon radical has the meanings given for the term "(Cl-C 4 )-alkyl"; 25 the term "(Cl-C 4 )-alkylamino" denotes, for example, methylamino, ethylamino, isopropylamino; the term "(Cl-C 4 )-dialkylamino" denotes, for example, dimethylamino, N-ethyl-N-methylamino, diethylamino, the term "(C 1
C
4 )-alkoxycarbonyl" denotes, for example, the methoxy 30 carbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonyl group; the term "(Cl-C 12 )-alkoxycarbonyl" denotes the abovementioned radicals and, for example, the hexyloxycarbonyl, 2-methylhexyloxycarbonyl, decyloxycarbonyl or dodecyloxycarbonyl group; 44 the term "(CilC 4 )-haloalkoxycarbonyl" denotes a (Ci-C 4 )-alkoxycarbonyl group in which one or more, in the case of fluorine possibly all, hydrogen atoms are replaced by halogen, preferably fluorine or chlorine; the term "(Cl-C 4 )-haloalkylthio" denotes a (Cl-C 4 )-alkylthio group in which 5 one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine; the term "(Cl-C 4 )-alkylsulfinyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group; 10 the term "(Cl-C 4 )-alkylsulfonyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group; the terms "(Cl-C 4 )-haloalkylsufinyl" and "(C 1
-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, 15 hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine; 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 20 group; the terms "(Cl C 4 )-haloalkoxy-(Cl-C 4 )-alkyl", "(C1-C 4 )-alkoxy-(C 1 C4) haloalkyl" and "(Cl-C 4 )-haloalkoxy-(Cl-C 4 )-haloalkyl" denote (Cl-C4) alkoxy-(CrC 4 )-alkyl radicals having the abovementioned meanings where one or more, in the case of fluorine possibly all, hydrogen atoms of the 25 appropriate hydrocarbon moieties are replaced by halogen, preferably chlorine or fluorine; the term "(Cl-C 4 )-alkylthio-(ClrC 4 )-alkyl" denotes, for example, methylthio methyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthio ethyl or 3-methylthiopropyl; 30 the term "arylthio" denotes, for example, the phenylthio or the 1- or 2-naphthylthio group; the term "aryloxy" denotes, for example, the phenoxy- or 1- or 2-naphthyl oxy group; the term "heterocyclyloxy" or "heterocyclylthio" denotes one of the 45 abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom; the term "cycloalkoxy" or "cycloalkylthio" denotes one of the above mentioned cycloalkyl radicals which are linked via an oxygen or sulfur 5 atom; the term "aroyl" denotes, for example, the benzoyl, naphthoyl or the biphenylcarbonyl group; the term "aryl-(C 1
C
4 )-alkanoyl" denotes, for example, the phenylacetyl, 3-phenylpropionyl, 2-phenylpropionyl, 2-methyl-2-phenylpropionyl, 10 4-phenylbutyryl or the naphthylacetyl group; the term "(C 3
-C
8 )-cycloalkyl-(C-C 4 )-alkanoyl" denotes, for example, the cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexyl carbonyl, cyclohexylacetyl or the cyclohexylbutyryl group; the term "heterocyclyl-(C 1
C
4 )-alkanoyl" denotes, for example, the thenoyl, 15 furoyl, nicotinoyl, thienylacetyl or the pyridinepropionyl group; the term "(C 3
-C
8 )-cycloalkoxycarbonyl" denotes, for example, the cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or the cycloheptyloxycarbonyl group; the term "(C 3
-C
8 )-cycloalkyl-(Cl-C 4 )-alkoxycarbonyl" denotes, for example, 20 the cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentyl oxymethoxycarbonyl, cyclohexyloxymethoxycarbonyl, 1-(cyclohexyl) ethoxycarbonyl or the 2-(cyclohexyl)ethoxycarbonyl group; the term "aryl-(C 1
C
4 )-alkoxycarbonyl" denotes, for example, the benzyl oxycarbonyl, 1-naphthylmethoxycarbonyl, 2-naphthylmethoxycarbonyl, 25 1 -phenylethoxycarbonyl or the 2-phenylethoxycarbonyl group; the term "heterocyclyl-(C-C 4 )-alkoxycarbonyl" denotes, for example, the thienylmethoxycarbonyl, furylmethoxycarbonyl, tetrahydrofurylmethoxy carbonyl or the pyridylethoxycarbonyl group; the term "aryloxycarbonyl" denotes, for example, the phenoxycarbonyl, 30 naphthoxycarbonyl or the biphenyloxycarbonyl group; the term "heterocyclyloxycarbonyl" denotes, for example, the tetrahydro pyran-4-oxycarbonyl group; the term "(C-C 20 )-alkanoyloxy" denotes, for example, the formyloxy, acetoxy, propionyloxy, butyryloxy, pivaloyloxy, valeroyloxy or the 46 hexanoyloxy group; the term "(C 2
-C
20 )-haloalkanoyloxy" denotes a (C 2
-C
20 )-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 5 chlorine; the term "(C 3
-C
8 )-cycloalkanoyloxy" denotes, for example, the cyclo propanoyloxy, cyclobutanoyloxy, cyclopentanoyloxy, cyclohexanoyloxy or the cycloheptanoyloxy group; the term "(C 3
-C
8 )-cycloalkyl-(Cl-C 4 )-alkanoyloxy" denotes, for example, the 10 cyclopropylcarbonyloxy, cyclopropylacetoxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cyclohexylacetoxy or the 4 -cyclohexylbutyryloxy group; the term "aroyloxy" denotes, for example, the benzoyloxy or the naphthoyloxy group; 15 the term "aryl-(C 1
-C
4 )-alkanoyloxy" denotes, for example, the benzoyloxy, naphthoyloxy, biphenylcarbonyloxy, phenylacetoxy or the phenylbutyryloxy group; the term "heterocyclyl-(Cl-C 4 )-alkanoyloxy" denotes, for example, the thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or the 20 pyrimidinylcarbonyloxy group; the term "(Cl-C2 0 )-alkylsulfonyloxy" denotes, for example, the methane-, ethane-, butane- or hexanesulfonyloxy group; the term "arylsulfonyloxy" denotes, for example, the phenylsulfonyloxy or the toluenesulfonyloxy group; 25 a "bivalent hydrocarbon chain" denotes a radical which is derived from n-alkanes or n-alkenes by removal of in each case one hydrogen atom from each of the two terminal carbon atoms of the chain, such as methylene, ethanediyl, trimethylene, tetramethylene; the term "(C 1
-C
18 )-alkanediyldioxy" denotes a bivalent radical derived from 30 (Cl-C 18 )-alkanes by replacement of two hydrogen atoms by two -0 radicals. Furthermore, the definition that "in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated 47 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, (Cl-C 4 )-alkoxy or (Cl-C 4 )-alkanoyl and where R 27 and R 28 are each (C 1
C
4 )-alkyl, preferably methyl, and where additionally 3 5 to 12 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals selected from the group consisting of halogen, 10 aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyl oxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, 15 heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to 20 three (in the case of fluorine up to the maximum number) identical or different substituents, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents" 25 denotes, for example: alkoxyalkyl radicals, for example the methoxymethyl, methoxyethyl or ethoxyethyl group; or 30 alkoxyalkoxyalkyl radicals, for example the methoxy- or the ethoxyethoxy ethyl group; or alkylthioalkyl radicals, for example the methyl- or the ethylthioethyl group; or alkylsulfinylalkyl radicals, for example the methyl- or ethylsulfinylethyl 48 group; or alkylsulfonylalkyl radicals, for example the methyl- or ethylsulfonylethyl group; or alkyldialkylsilylalkyl radicals, preferably alkyldimethylsilylalkyl radicals, for 5 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 cycloalkyldialkylsilyl radicals, preferably cycloalkyldimethylsilyl radicals, for 10 example the cyclohexyldimethylsilyl group; or aryldialkylsilyl radicals, preferably aryldimethylsilyl radicals, for example the phenyldimethylsilyl group; or arylalkyldialkylsilyl radicals, preferably aryldimethylsilyl radicals, for example the benzyldimethylsilyl or the phenylethyldimethylsilyl group; or 15 alkanoylalkyl radicals, for example the acetylmethyl or the pivaloylmethyl group; or cycloalkanoylalkyl radicals, for example the cyclopropylcarbonylmethyl or the cyclohexylcarbonylmethyl group; or haloalkanoylalkyl radicals, for example the trifluoro- or trichloroacetylmethyl 20 group; or 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 25 arylalkyl radicals, for example the benzyl, the 2-phenylethyl, the 1-phenylethyl, the 1-methyl-1-phenylethyl group, the 3-phenylpropyl, the 4-phenylbutyl group, the 2 -methyl-2-phenylethyl group or the 1-methyl- or 2-methylnaphthyl group; or heterocyclylalkyl radicals, for example the thienylmethyl, pyridylmethyl, 30 furfuryl-, tetrahydrofurfuryl-, tetrahydropyranylmethyl- or the 1,3-dioxalane 2-methyl group; or aryloxyalkyl radicals, for example the phenoxymethyl or naphthoxymethyl group; or cycloalkyl radicals, monocyclic such as, for example, the cyclopropyl, 49 cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical, bicyclic such as, for example, the norbornyl radical or the bicyclo[2.2.2]octane radical or condensed such as the decahydronaphthyl radical; alkylcycloalkyl radicals, for example the 4-methyl- or the 4-tert-butylcyclo 5 hexyl group or the 1 -methylcyclopropyl, -cyclobutyl, -cyclopentyl- or -cyclohexyl group; cycloalkylalkyl radicals, for example the cyclohexylmethyl or -ethyl group; or else haloalkyl derivatives of the appropriate groups, for example halo alkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkylcycloalkyl or halocycloalkyl 10 radicals. This applies correspondingly to similar definitions. The illustration given above applies correspondingly to homologs or to radicals derived therefrom. 15 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 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 compounds 20 by conventional methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by conventional methods, for example by salt formation with an optically active acid, separation of the diastereomeric salts and liberation of the pure enantiomers using a base. 25 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 30 R 3 SG (V) R N R 50 where G is CH or N and R', R 2 , R 3 , X, Y and Z are each as defined under formula I, with an electrophile of the formula (VI) 5 L E R 6 R 4 R 5(I 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 10 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 this manner by other anions according to known methods [for example Liebigs Ann. Chem. 1978, 1937; Methoden der Org. Chemie/Houben-Weyl 15 (D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 1008 ff., Thieme, Stuttgart 1990]. The substitution reaction described above is known in principle [for example Methoden der Org. Chemie/Houben-Weyl (D. Klamann, Ed.), 20 4th Edition, Vol. E16a, Part 2, p. 997 ff., Thieme, Stuttgart 1990, Liebigs Ann. Chem. 621 (1959) 106; Arch. Pharm. (Weinheim) 328 (1995) 531]. The structures (V) and (VI) can be varied within wide limits. 25 The abovementioned reaction is carried out in a temperature range from 20 to 1500C, if appropriate in an inert organic solvent such as acetonitrile, acetone, 2-butanone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4 methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol, ethylene 30 glycol dimethyl ether, toluene, chlorobenzene or xylene. It is also possible to use mixtures of the solvents mentioned. Most of the compounds of the formula (V) required as starting materials are known from the literature [for example DE-A-4 438 807, WO-A- 51 96 11 913, WO-A-96 11 924, DE-4 343 250, WO-A-95 07 890, WO-A 94 21 613, DE-A-4 208 254], or they can be prepared similarly to known methods. 5 Compounds of the formula (VI) are commercially available, or they can be obtained by processes known in principle [for example: Acta Chem. Scand. 20 (1966) 1273; Chem. Ber. 92 (1959) 1599; J. Am. Chem. Soc. 95 (1973) 7813; Zh. Obshch. Khim, 28 (1958) 1930; J. Am. Chem. Soc. 43 (1921) 660]. 10 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 very preferably for controlling insects and arachnids, which are 15 encountered in agriculture, in animal breeding, in forestry, in the protection of stored products and materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or certain stages of development. The abovementioned pests include: From the order of the Acarina, for example, Acarus siro, Argas spp., 20 Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.. 25 From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.. 30 From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example, Lepisma saccharina. From the order of the Collembola, for example, Onychiurus armatus. From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus, 52 Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. From the order of the Isoptera, for example, Reticulitermes spp.. From the order of the Anoplura, for example, Phylloera vastatrix, 5 Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.. From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.. From the order of the Thysanoptera, for example, Hercinothrips femoralis, 10 Thrips tabaci and Frankliniella spp.. From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.. From the order of the Homoptera, for example, Aleurodes brassicae, 15 Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arandinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, 20 Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.. From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, 25 Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria 30 mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp.. From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, 53 Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, 5 Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogorma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conorus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptus spp.. 10 From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.. From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., 15 Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. From the order of the Siphonaptera, for example, Xenopsylla cheopsis and 20 Ceratophyllus spp.. From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. From the class of the Helminthes, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, 25 Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis and also Fasciola. From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., 30 Bulinus spp. and Oncomelania spp.. From the class of the Bivalva, for example, Dreissena spp.. The plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil nematodes such 54 as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii) and of the 5 genera Radopholus, such as Radopholus similis, Pratylenchus, such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus, Tylenchulus, such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus 10 such as Rotylenchus robustus, Heliocotylenchus, such as Heliocotylenchus multicinctus, Belonoaimus, such as Belonoaimus longicaudatus, Longidorus, such as Longidorus elongatus, Trichodorus, such as Trichodorus primitivus, and Xiphinema, such as Xiphinema index. 15 The compounds according to the invention can also be used to control the nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (leaf-gall nematodes, such as Anguina tritici). 20 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. 25 The compositions according to the invention comprise the active substances of the formulae I in general in a proportion of from 1 to 95% by weight. They can be formulated in various ways depending on the biological and/or 30 chemicophysical parameters which prevail. Possible formulations which are suitable are therefore: wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusts (DP), seed-dressing products, granules in the 55 form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits. 5 These individual types of formulation are known in principle and are 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; 10 K. Martens, "Spray Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd. London. The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for 15 example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, N.Y.; Marsden, "Solvents Guide", 2nd ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and 20 Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Sch6nfeldt, "Grenzfldchenaktive Athylenoxidaddukte" [Surface-Active Ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker KOchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 25 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 30 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 polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium lignosulfonate or sodium 2,2'-dinaphthylmethane- 56 6,6'-disulfonate. Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclo hexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers. As emulsifiers, the 5 following can be used, for example: calcium salts of 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, polyoxyethylene sorbitan fatty 10 acid esters or polyoxethylene sorbitol esters. Dusting agents are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, poryphillite or diatomaceous earth. Granules can be prepared 15 either by atomizing the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of carrier materials such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or alternatively mineral oils. Suitable active substances can 20 also be 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 25 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. Formulations in dust form 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 30 granules, the content of active substance depends partly on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc. are being used. In addition, the abovementioned formulations of active substance 57 comprise, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are customary in each case. 5 The concentrates, which are in the commercially customary form, are if appropriate diluted in the customary manner for their use, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and some microgranules. Dust and granule preparations, and also sprayable solutions, are normally not diluted any further with other 10 inert substances before being used. The application rate required varies with the external conditions, such as temperature and humidity among others. It can fluctuate within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, 15 but is preferably between 0.001 and 5 kg/ha. The active substances according to the invention may be present in their commercially customary formulations, and in the application forms prepared from these formulations, as mixtures with other active 20 substances, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides. The pesticides include, for example, phosphates, carbamates, carboxylates, formamidines, tin compounds and substances produced by 25 microorganisms, inter alia. Preferred mixture components are 1. from the group of the phosphorus compounds 30 acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos methyl, demeton, demeton-S-methyl, demeton-S-methylsulphone, dialifos, diazinon, dichlorvos, dicrotophos, 0,0-1, 2 ,2,2-tetrachloroethyl phosphoro thioate (SD 208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos, 58 etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isozophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, 5 parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, pirimiphos, pirimiphos-ethyl, pirimiphos methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tetra chlorvinphos, thiometon, triazophos, trichlorphon, vamidothion; 10 2. from the group of the carbamates aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbo furan, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, 15 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), 1-methylthio(ethylideneamino)-N-methyl-N-(morpholinothio)carbamate (UC 51717); 20 3. from the group comprising the carboxylates 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)methyl (1 RS)-trans-3-(4-tert-butyl 25 phenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, 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, 30 tefluthrin, tetramethrin, tralomethrin; 4. from the group of the amidines amitraz, chlordimeform; 59 5. from the group of the tin compounds cyhexatin, fenbutatin oxide; 6. others 5 abamectin, Bacillus thuringiensis, bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron, 2
-(
4 -chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), clorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazin, ethyl N-(3,5-dichloro-4-(1,1, 2
,
3 ,3,3-hexafluoro-1 -propyloxy)phenyl)carbamoyl) 10 2 -chlorobenzocarboximidate, DDT, dicofol, N-(N-(3,5-dichloro-4-(1,1,2,2 tetrafluoroethoxy)phenylamino)carbonyl)-2,6-difluorobenzamide (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 15 ( 4 -fluoro-3-phenoxyphenyl)propyl)dimethylsilane, fenoxycarb, 2-fluoro-5
(
4
-(
4 -ethoxyphenyl)-4-methyl-1 -pentyl)diphenyl ether (MTI 800), granulosis 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 20 methyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan 3-ylcarbamaldehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron and imidacloprid. The active substance content of the use forms prepared from the 25 commercially customary formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1 % by weight. Application is effected in a conventional fashion, matched to the use forms. 30 The active substances according to the invention are also suitable for controlling ecto- and endoparasites in the veterinary medical sector or in the sector of animal husbandry. The active substances according to the invention are in this case applied in 60 a known fashion, such as by oral application in the form of, for example, tablets, capsules, potions or granules, by dermal application in the form of, for example, dipping, spraying, pouring-on and spotting-on and powdering, and also by parenteral application in the form of, for example, injection. 5 The novel compounds, according to the invention, of the formula I can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.). In a preferred embodiment of the invention, the novel 10 compounds, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since excretion in the droppings occurs in an effective fashion, the development of insects in the animal droppings can be prevented very simply in this fashion. The dosages and formulations suitable in each case 15 are particularly dependent on the type and stage of development of the productive animals and also on the degree of infestation, and can easily be determined and fixed by conventional methods. In the case of cattle, the novel compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight. 20 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 25 case of those fungal diseases which can no longer be controlled effectively with the otherwise customary fungicides when infection has taken place already. The spectrum of action of the claimed compounds embraces various economically important phytopathogenic fungi, for example Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Piricularia 30 oryzae, Pyrenophora teres, Leptosphaeria nodorum, Pellicularia sasakii and Puccinia recondita. In addition, the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as 61 preservatives in paints, in cooling lubricants for metalworking, or as preservatives in drilling and cutting oils. The active substances according to the invention in their commercially 5 customary formulations can be employed either alone or in combination with other fungicides known from the literature. Examples of fungicides which are known from the literature and which can be combined, in accordance with the invention, with the compounds of the 10 formula I are the following products: aldimorph, andoprim, anilazine, BAS 480F, BAS 450F, BAS 490F, benalaxyl, benodanil, benomyl, binapacryl, bitertanol, bromuconazole, buthiobate, captafol, captan, carbendazim, carboxin, CGA 173506, cyprodinil, cyprofuram, dichlofluanid, dichlomezin, diclobutrazol, 15 diethofencarb, difenconazole (CGA 169374), difluconazole, dimethirimol, dimethomorph, diniconazole, dinocap, dithianon, dodemorph, dodine, edifenfos, ethirimol, etridiazole, epoxiconazole, fenbuconazole, fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferimzone (TF164), fluazinam, fluobenzimine, fludioxinil, 20 fluquinconazole, fluorimide, flusilazole, flutolanil, flutriafol, folpet, fosetyl aluminium, 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, 25 maneb, mepanipyrim (KIF 3535), metconazol, mepronil, metalaxyl, methasulfocarb, methfuroxam, MON 24000, myclobutanil, nabam, nitrothalidopropyl, nuarimol, ofurace, oxadixyl, oxycarboxin, penconazole, pencycuron, PP 969, probenazole, propineb, prochloraz, procymidon, propamocarb, propiconazole, prothiocarb, pyracarbolid, pyrazophos, 30 pyrifenox, pyrimethanil, pyroquilon, rabenzazole, RH7592, sulfur, tebuconazole, TF 167, thiabendazole, thicyofen, thiofanatemethyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxid, tricyclazole, tridemorph, triflumizol, triforine, trifionazol, validamycin, vinchlozolin, XRD 563, zineb, sodium dodecylsulfonate, sodium dodecyl sulfate, sodium 62 C13/C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester, sodium dioctylsulfosuccinate, sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, cetyltrimethylammonium chloride, salts of long-chain primary, secondary or tertiary amines, 5 alkylpropyleneamines, laurylpyrimidinium bromide, ethoxylated quaternized fatty amines, alkyldimethylbenzylammonium chloride and 1-hydroxyethyl 2-alkylimidazoline. The abovementioned components for combinations are known active 10 substances of which many are described in Ch.R. Worthing, S.B. Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council. The active substance content of the use forms prepared from commercially customary formulations can vary within wide limits, and the concentration of active substance in the use forms can be from 0.0001 up to 95% by 15 weight of active substance, preferably between 0.0001 and 1% by weight. The formulations are applied in a customary manner adapted to suit the use forms. The examples which follow illustrate the invention without limiting it thereto. 20 A. Formulation Examples a) A dusting agent is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as inert material and 25 comminuting in a hammer mill. b) A wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of 30 kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding in a pinned disk mill.
63 c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium lignosulfonate and 51 parts by weight of water and grinding 5 in a ball mill to a fineness of below 5 microns. d) An emulsifiable concentrate can be prepared from 15 parts by weight of active substance, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of ethoxylated nonylphenol (10 EO) 10 as emulsifier. e) Granules can be prepared from 2 to 15 parts by weight of active substance and an inert granule carrier material such as attapulgite, granulated pumice and/or quartz sand. It is advantageous to use a 15 suspension of the wettable powder of Example b) with a solids content of 30% which is sprayed onto the surface of attapulgite granules which are then dried and intimately mixed. The proportion by weight of the wettable powder in this case is about 5% and that of the inert carrier material is about 95% of the finished granules. 20 B. Preparation examples Example 1
OH
3
CH
7 + 25
CH
3 HN N0 3 ~ H3C,-, O N ~~~0 30 H3C N S
CH
3 64 4 -(cis-4-tert-butylcyclohexylamino)-5-methoxy-6-methoxymethyl- 1-methyl thiomethylpyrimidinium nitrate 0.76 g (2.44 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-5-methoxy-6 5 methoxymethylpyrimidine and 0.23 g (2.44 mmol) of chloromethyl methyl sulfide in 40 ml of acetonitrile were admixed with 0.41 g (2.44 mmol) of silver nitrate. The mixture was stirred at 250C for 1 hour and then filtered. The residue was washed with methylene chloride and the filtrate was concentrated. Crystallization from petroleum ether/ethyl acetate gave 10 0.36 g (34%) of colorless crystals of m.p. 1550C. Example 2 CH3 15
CH
3 HN CI N 20 H 3 C CH3
H
3 C CH 3 5-chloro-6-ethyl-4-(cis-4-tert-butylcyclohexylamino)-1 -pivaloyloxymethyl pyrimidinium iodide 25 1.00 g (3.38 mmol) of 5-chloro-6-ethyl-4-(cis-4-tert-butylcyclohexylamino) pyrimidine and 0.82 g (3.38 mmol) of iodomethyl pivalate in 40 ml of acetonitrile were refluxed for 8 hours. The solvent was removed under reduced pressure. Chromatography (silica gel; ethyl acetate/methanol) 30 gave 0.51 g (28%) of yellowish crystals of mp. 98 0 C. Preparation of the starting material iodomethyl pivalate 5.00 g (33.2 mmol) of chloromethyl pivalate and 29.8 g (199.2 mmol) of 65 sodium iodide in 50 ml of acetone were stirred at 25*C for 24 h. The acetone was removed, the residue was taken up in H 2 0/CH 2
C
2 , the organic phase was separated off and the aqueous phases were extracted three times with 50 ml of CH 2 Cl 2 each time. The combined organic phases 5 were dried and the solvent was removed. Distillation of the residue at 0.65 mbar gave 4.23 g (53%) of an orange-brown oil of bp. 37*C. The compounds listed in the tables below were obtained similarly to Examples 1 and 2. 10 Definition of the heterocycle radicals Hetn: Het R a X C1 N Rb
H
3 C Het 2 Ra x N Rb Het 3 66 Het 3 Ra x cI
H
3 C N R b Het 4 R a H 3 c N+~S Rb Het 5 R a :37 Br N 'R b
H
3
C
67 Het 6) R a X cI R b
H
3 C Het 7 *) Ra N Rb Het *)R oR a Ax N Rb Het 9 ) xa N IN Rb
F
Hetlo68 R a H NKR
H
3 C Het 1 ) Ra N R Het 1 2 * R a N~ R
H
3
C
69 Het 13 * R a Br N
H
3 C Het 14 * R a Br N
H
3 N~ ~R Het' 5 * R a 0
H
3 C N HC N Rb 3 I 70 Het'1 6 Ra owR x N Rb H 3 c Het 17 * Ra 0 x N Rb Het 18 *) Ra NN CII Nk R b
H
3
C
71 H e t 9 * ) x R a N N Rb Het 20 Ra N N R b F Het 21 ) Ra R 5 +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 system, instead to an N* in position 1 of this ring system. 15 72 Other abbreviations used: Ph phenyl Me methyl 5 Et ethyl nPr n-propyl iPr isopropyl tBu tert-butyl 73 Table 1 LHet - CH- E - R6] 15 R Q No. Het" X Ra Rb E R 5
R
6 0 Physical I_ I properties 3 Het' NH Ph H 0 H -C(O)tBu CI 4 Het' NH tBu H 0 H -C(O)tBu 5 Het' NH tBu CH 3 0 H -C(O)tBu 6 Het' NH tBu H 0 H -CH 2
CH
3 Cl 7 Het' NH tBu H SO H -CH3
NO
3 8 Het' NH tBu H S H -CH 3
NO
3 9 Het' NH tBu H SO2 H -CH 3
NO
3 10 Hee NH Ph H 0 H -CH 2
CH
3 CI 11 Het NH Ph CH 3 0 H -C(O)Ph 12 Hef NH tBu H S H -CH 3
NO
3 13 HeF NH iPr H SO H -CH 3
NO
3 14 Het 3 NH Ph H 0 H -C(O)iPr Cl 15 Het 3 NH Ph H 0 H -C(O)Ph 16 Het 4 NH Ph H S H -CH 3
NO
3 17 Het 5 NH Ph CH 3 S H -CH 3 NO 3 18 Het' NH Ph H 0 H -CH 2
CH
3 C 19 Het' NH Ph H 0 H -C(O)CH 2
CH
3 I 'H-NMR (CDC1 3 ): 6 = 1.1 (t,3H), 1.4 (t, 3H), 6.4 (s, 2H), 6.5 (d, NH), 8.8 (d, 1H). 20 HetI NH Ph H 0 H -C(O)CH 2 Ph 1 21 Het' NH Ph H 0 H -C(O)C(CH 3 )= 0l
CH
2 22 Het' NH Ph H 0 H -C(O)Ph C1 23 Het' NH Ph H 0 H -C(O)Ph I mp. 198*C 24 Het' NH Ph H 0 H -C(O)Ph Br 25 Het' NH Ph H 0 H -C(O)-2-methyl- I phenyl 26 Het' NH Ph H 0 H -C(O)-2-pyridyl CI 74 No. Hetn X Ra Rb E R 5
R
6 Q Physical I ______ I________ ___ properties 27 Het' NH Ph H 0 H -C(O)-2,6-di- I methylphenyl 28 Het' NH Ph H 0 H -C(O)nPr 29 Het' NH Ph H 0 H -C(O)-4-nitro- I phenyl 30 Het' NH Ph H 0 H -C(O)-4-pyridyl CI 31 Het' NH Ph H 0 H -C(O)-2,4-di- I chlorophenyl 32 Het NH Ph H NH H C(O)Ph Br 33 Het' NH Ph H 0 H -C(O)-2,6-di- I methoxyphenyl 34 Het NH Ph H 0 H -C(O)-3-pyridyl I 35 Het' NH Ph H 0 H -C(O)iPr I 'H-NMR (CDCl 3 ): 6 = 1.2 (d, 6H), 6.4 (s, 2H), 6.5 (d, NH), 7.3 (m, 6H), 8.8 (d, 1H). 36 Het' NH Ph H S H -CH 3
NO
3 37 Het NH Ph H SO H -CH 3
NO
3 38 Het 6 NH tBu H NH H -C(O)Ph Br 39 Het 6 NH tBu H 0 H -C(O)CH 2
CH
3 I mp. 101*C 40 Het 6 NH tBu H 0 H C(O)C(CH 3 )=
CH
2 41 Hets NH tBu H 0 H -C(O)Ph I mp. 128-130*C 42 Het 6 NH tBu H 0 H -C(O)Ph CI 43 Het 6 NH tBu H 0 H -C(O)-2-methyl- I mp. 117*C phenyl 44 Het 6 NH tBu H 0 H -C(O)-Ph Br 45 Het 6 NH tBu H 0 H -C(O)-2,6- I mp. 109*C dimethylphenyl 46 Het 6 NH tBu H 0 H -C(O)-2-pyridyl I 47 Het 6 NH tBu H 0 H -C(O)-4-nitro- I I I_ pheny 48 Het 6 NH tBu H 0 H -C(O)-4-pyridyl Br 49 Het 6 NH tBu H 0 H -C(O)-2-nitro- I mp. 1210C I _phenyl 50 Het 6 NH tBu H 0 H -C(O)-3-pyridyl Cl 51 Het 6 NH tBu H 0 H -C(O)-2,4- I I_ I dichlorophenyl 52 Het 6 NH tBu H 0 H -C(O)-CH 2 Ph I 53 Het 6 NH tBu H 0 H -C(O)-2,6- I mp. 151*C dichlorophenyl 75 No. Het" X Ra Rb E R 5
R
6 Q Physical properties 54 Het 6 NH tBu H 0 H -C(O)CH 2 -(4- I chlorophenyl) 55 Het 6 NH tBu H 0 H -C(O)-2,4- I dinitrophenyl 56 Het 6 NH tBu H 0 H -C(O)CH 2 -(4-tert- I butylphenyl) 57 Het 6 NH tBu H 0 H -C(O)-4-chloro- I mp. 172*C phenyl 58 Het 6 NH tBu H 0 H -C(0)-2 methoxyphenyl 59 Het 6 NH tBu H 0 H -C(O)-2,4- I mp. 920C dimethoxyphenyl 60 Het 6 NH tBu H 0 H -C(O)-2,6-di- I mp. 172*C methoxyphenyl 61 Het 6 NH tBu H 0 H -C(O)-1-methyl- I cyclohexyl 62 Het 6 NH tBu H 0 H -C(O)iPr I mp. 67-69"C 63 Het 6 NH tBu H 0 H -C(O)cyclohexyl I 64 Het 6 NH tBu H 0 H -C(O)tBu Cl 65 Hete NH tBu H 0 H -C(O)tBu Br 66 Het 6 NH tBu H 0 H -C(O)tBu BF4 67 Het 6 NH tBu H NH H -C(O)tBu Br 68 Het 6 NH tBu H 0 H -C(O)tBu NO 3 mp. 104*C 69 Het 6 NH tBu H so H -CH 3
NO
3 70 Het 6 NH tBu H S H -CH 3
NO
3 mp. 1380C 71 Het 6 NH tBu H S H -CH 2
CH
3
NO
3 72 Het 6 NH tBu H S H -CH 3
BF
4 mp. 1320C 73 Het 6 NH tBu H S H -CH 2
CH
3
NO
3 74 Het 7 0 tBu H S H -CH 3
NO
3 75 Het 8 0 tBu H 0 H -C(O)Ph 76 Het 9 0 tBu H 0 H -C(O)Ph I 77 Het 6 NH tBu OH 3 0 H -C(O)Ph Cl 78 Het 6 NH tBu OH 3 0 H -C(O)Ph I 79 Het 6 NH tBu OH 3 0 H -C(O)tBu 80 Het 6 NH tBu OH 3 0 H -C(O)iPr 81 Het 6 NH tBu C 0 H -C(O)tBu Cl 82 Het 6 NH tBu Cl 0 H -C(O)Ph I 83 Het 1 0 NH tBu H 0 H -C(O)Ph I 84 Het" NH tBu H NH H -C(O)-4-tert- Br butylphenyl 85 ,Het' NH tBu H .0 H -C(O)CH 2
CH
3
I
76 No. Het" X Ra Rb E R 5
R
6 Q Physical properties 86 Het' 1 NH tBu H 0 H -C(O)cyclohexyl I 87 Het" NH tBu H 0 H -C(O)iPr I mp. 184"C 88 Hetl NH tBu H 0 H -C(O)-i-methyl- I cyclohexyl 89 Het 1 NH tBu H 0 H -C(O)Ph Cl 90 Het" NH tBu H NH H -C(O)Ph Cl 91 Het" NH tBu H 0 H -C(O)Ph I mp. 193*C 92 Het" NH tBu H 0 H -C(O)-3-pyridyl 93 Het' NH tBu H 0 H -C(O)-2-methyl phenyl 94 Het' NH tBu H 0 H -C(O)-2,6 dimethylphenyl 95 Het" NH tBu H 0 H -C(O)-2-nitropheny I 96 Het" NH tBu H 0 H -C(O)-2,6 dimethoxyphenyl 97 Het NH tBu H NH H -C(O)tBu 98 Het NH tBu H 0 H -C(O)tBu Cl 99 Het" NH tBu H 0 H -C(O)tBu I mp. 201*C 100 Het' 1 NH tBu H 0 H -C(O)C(CH 3 ) Cl
=CH
2 101 Het1 2 NH tBu H 0 H -C(O)tBu 102 Het 6 NH tBu F 0 H -C(O)Ph 103 Het1 3 NH tBu H 0 H -C(O)Ph 104 Het' 4 NH tBu H 0 H -C(O)iPr 105 Het1 4 NH tBu H 0 H -C(O)Ph Cl 106 Het1 4 NH tBu H 0 H -C(O)Ph 107 Het1 4 NH tBu H 0 H -C(O)-2-methyl- I phenyl 108 Het1 4 NH tBu H 0 H -C(O)-2-nitrophenyl I 109 Het1 4 NH tBu H 0 H -C(O)-2,6-di methoxyphenyl 110 Het1 4 NH tBu H 0 H -C(O)tBu Cl 111 Het1 4 NH tBu H 0 H -C(O)tBu 112 Het' 5 NH tBu H S H
-CH
3 BF4 113 Het1 5 NH tBu H S02 H
-CH
3 BF4 114 Hat' NH nPr H 0 H -C(O)iPr I mp. 1300C 115 Het 6 NH nPr H 0 H -C(O)C(CH 3
)CH
2 I 116 Het 6 NH nPr H H -C(O)tBu 117 Het 6 NH nPr H 0 H -C(O)tBu CI 118 Het 6 NH nPr H NH H -C(O)Ph Br 77 No. Het" X Ra Rb E R 5
R
6 Q Physical properties 119 Het 6 NH nPr H 0 H -C(O)Ph I mp. 89*C 120 Het 6 NH nPr H 0 H -C(O)-2-methyl- I phenyl 121 Het' NH nPr H 0 H -C(O)-2-nitrophenyl 1 122 Het 6 NH nPr H 0 H -C(O)-2,6-di- I methoxyphenyl 123 Het 9 0 nPr H 0 H -C(O)Ph I 124 Het 6 NH nPr CH 3 0 H -C(O)Ph 125 Het 6 NH nPr CH 3 NH H -C(O)Ph 126 Hetl NH nPr H 0 H -C(O)Ph 127 Het' 4 NH nPr H 0 H -C(O)Ph 128 Het 6 NH iPr H 0 H -C(O)Ph CI 129 Het 6 NH iPr H 0 H -C(O)-2-pyridyl I 130 Het 6 NH iPr H 0 H -C(O)Ph I mp. 115*C 131 Het 6 NH iPr H 0 H -C(O)-3-pyridyl I 132 Het 6 NH iPr H 0 H -C(O)-2-methyl- I I _phenyl 133 Het 6 NH iPr H 0 H -C(O)-1-naphthyl I 134 Het 6 NH iPr H 0 H -C(O)-2,6-di- I methylphenyl 135 Het 6 NH iPr H 0 H -C(O)-4-nitrophenyl I 136 Het 6 NH iPr H 0 H -C(O)-4-pyridyl 1 137 Het 6 NH iPr H 0 H -C(O)-2-nitrophenyl I 138 Het 6 NH iPr H 0 H -C(O)-2,6-di- I I _chlorophenyl 139 Het 6 NH iPr H 0 H -C(O)-2,6-di- I methoxyphenyl 140 Het 6 NH iPr H 0 H -C(O)tBu I mp. 660C 141 Het 6 NH iPr H 0 H -C(O)iPr I mp. 115*C 142 Het 6 NH iPr CH 3 0 H -C(O)Ph _ 143 Hetl NH iPr H 0 H -C(O)Ph 144 Het 14 NH iPr H 0 H -C(O)tBu 1 145 Het 14 NH iPr H 0 H -C(0)Ph I 146 Het 13 NH iPr H 0 H -C(O)Ph I mp.71*C 147 Het 6 NH -C(CH 3
)CF
3 H 0 H -C(O)tBu C1 148 Het 6 NH -C(CH 3
)CF
3 H 0 H -C(O)tBu 1 149 Het 6 NH -C(CH 3
)CF
3 H 0 H -C(O)Ph I mp. 1190C 150 Het 6 NH -C(CH 3
)CF
3 H 0 H -C(O)iPr _ 151 Het 1 NH -C(CH 3
)CF
3 H 0 H -C(O)Ph 152 Het 6 NH -C(CH 3
)CF
3
CH
3 0 H -C(O)iPr I 78 No. Hetn X Ra Rb E R 5
R
6 O Physical - X I -properties 153 Het 6 NH -C(CH 3
)CF
3
CH
3 0 H -C(O)Ph 154 Het1 4 NH -C(CH 3
)CF
3 H 0 H -C(O)Ph 155 Het 6 NH -C(CH 3
)CF
3 Cl 0 H -C(O)Ph 156 Het 6 NH SiMe 3 H 0 H -C(O)tBu C 157 Het 6 NH SiMe 3 H 0 H -C(O)tBu 158 Het 6 NH SiMe 3 H 0 H -C(O)Ph I mp. 135*C 159 Het 6 NH SiMe 3 H 0 H -C(O)iPr 160 Het 6 NH SiMe 3
CH
3 0 H -C(O)Ph 161 Het 1 NH SiMe 3 H 0 H -C(O)Ph I mp. 164*C 162 Het1 3 NH SiMe 3 H 0 H -C(O)Ph I mp. 160*C 163 Het' 0 NH SiMe 3 H 0 H -C(O)Ph MP. 194C 164 Het' 0 NH SiMe 3 H 0 H -C(O)iPr 165 Het 10 NH SiMe 3 H 0 H -C(O)tBu I mp. 162*C 166 Het 15 NH SiMe 3 H S H -CH 3 NO 3 167 Het 6 NH Ph H S H -CH 3
NO
3 mp. 79-81*C 168 Het 6 NH Ph H SO H -CH 3 Cl 169 Het 6 NH Ph H 0 H -C(O)CH 2
CH
3 I 'H-NMR (CDC1 3 ): 6 = 3.2 (q,2H), 6.4 (s,2H), 6.9 (d,NH), 9.1 (s,1 H). 170 Het 6 NH Ph H 0 H -C(O)Ph mp. 169 ---. _ _170*C 171 Hat 6 NH Ph H 0 H -C(O)Ph C 172 Het 6 NH Ph H 0 H -C(O)Ph 173 Het 6 NH Ph H 0 H -C(O)-2-methyl- I mp. 1830C I _ _ ,phenyl 174 Het 6 NH Ph H 0 H
-C(O)C(CH
3 )=
OH
2 ____ 175 Het 6 NH Ph H 0 H -C(O)-2,6-di- I mp. 19600 methylphenyl 176 Het 6 NH Ph H 0 H -C(O)CH 2 Ph I 177 Het 6 NH Ph H 0 H -C(O)-2-nitrophenyl I mp. 11800 178 Hat 6 NH Ph H 0 H -C(O)-2-pyridyl I 179 Het 6 NH Ph H 0 H -C(O)-2,4 dichlorophenyl 180 Het 6 NH Ph H 0 H -C(O)CH 2 -(4- Br chlorophenyl) 181 Het 6 NH Ph H 0 H -C(O)-2,6- C I I dichlorophenyl 182 Hat 6 NH Ph H 0 H -C(O)CH 2 -(4-tert- I butylphenyl) 79 No. Het" X Ra Rb E RR Q Physical Properties 183 Het 6 NH Ph H 0 H -O)-2,6 ___________dinitrophenyl 184 Het 6 NH Ph H 0 H -O)-3-pyridyl 185 Het NH Ph H 0 H -O)-4-chloro I mp. 18700 ______I__, phenyl 186 Het 6 NH Ph H 0 H -C(0)-4-pyridyl 187 Het 6 NH Ph H 0 H -O)-2-naphthyl CI 188 Het 6 NH Ph H 0 H C(0)-1-naphthA I 189 Het 6 NH Ph H 0 H ______I___ methoxyphenyl 190 Het 6 NH Ph H 0 H -C(0)Cyclohexyl CI 191 Het 6 NH Ph H 0 H -C(0)-2,4-di- mp. 87*C I methoxyphenyl 192 Het 6 NH Ph H 0 H -C(0)-1-methyl I I cyclohexyl 193 Het 6 NH Ph H 0 H -C(7)-2,6-d- 1mp. __________methoxyphenyl 197-199*C 194 Het 6 NH Ph H 0 H *C(0)cyclopentyl 1 195 Het 6 NH Ph H 0 H -C(0)iPr mp. 61-64*C 196 Het 6 NH Ph H H -C()nBu 197 Het 6 TNH Ph H 0 H -C(C)tBu cl 198 Het 6 NH Ph H o H -C(0)tBu Br 199 Het 6 NH Ph H 0 H -C(0)tBu mp. 122*C 200 Het 6 NH Ph H NH H -C(0)tBu 201 Het 7 NH Ph H 0 H -C(0)Ph 202 Het 8 0 Ph H 0 H -C(0)Ph 203 Het 9 NH Ph H 0 H -C(0)Ph 204 Het 6 NH Ph H 0 H -C(0)C(CH 3
)-CH
2 1 205 Het 6 NH Ph CH 3 0 H -C(0)iPr 206 Het 6 NH Ph CH 3 NH H -C(0)iPr 207 Het 6 NH Ph OH 3 0 H -O)tBu 208 Het 6 NH Ph
CH
3 0 H -O)CH 2 Ph 209 Het 6 NH Ph CH 3 0 H *O)Ph 210 Het 6 NH Ph CH 3 0 H -CO)Ph Of 211 Het 6 NH Ph C10 H O)iPr 212 Het 6 NH Ph Of 0 H
-C(O)C(CH
3 )= ______ O H 2 213 Het 6 NH Ph O 0 H -O)tBu 214 Het 6 NH Ph O 0 H -O)Ph 215 Het 6 NH Ph O 0 H -COi)Ph 01 80 No. Het"' X Ra Rb E R 5 R0 Physical I _____I_ properties 216 Het' 0 NH Ph H 0 H -C(O)Ph Cl 217 Het' 0 NH Ph H 0 H -C(O)Ph 218 Hetl NH Ph H 0 H -O(O)iPr mp. 17800 219 Het" NH Ph H 0 H -C(O)tBu mp. 197*C 220 Het' NH Ph H 0 H -C(O)Ph mp. 18300 221 Het' NH Ph H 0 H -C(O)Ph CI 222 Het' 2 NH Ph H 0 H C(O)Ph 223 Het 6 NH Ph F 0 H -C(O)Ph 224 Het 13 NH Ph H 0 H -C(O)Ph 225 Het 14 NH Ph H 0 H -C(O)iPr 226 Het 14 NH Ph H 0 H -C(O)Ph 227 Het1 NH Ph H 0 H -C(0)Ph C 228 Het 14 NH Ph H 0 H -C(O)tBu 229 Het 14 NH Ph H 0 H -C(O)tBu Cl 230 Het 15 NH Ph H s H -OH 3 NO 3 231 Het' 5 NH Ph H 0 H -C(O)Ph 232 Het1 5 0 Ph H 0 H -C(O)Ph 233 Het 15 NH Ph H 0 H -C(O)Ph Br 234 Het 15 0 Ph H 0 H -C(O)Ph Br 235 Het' 5 NH Ph H S H -OH 3 NO 3 236 Het' 5 NH Ph H SO H -OH 3 NO 3 237 Het1 5 NH Ph H S H -OH 3 NO 3 238 Het 15 0 Ph H S H -CH 2
CH
3 CI 239 Het15 NH Ph H S H -cyclohexyl
NO
3 240 Het 6 NH -C(CH 3
)
2 H 0 H -C(O)cyclohexyl I
CH
2 tBu 241 Hete NH *O(OH 3
)
2 H 0 H -C(O)iPr 242 Het 6 NH -CCH 3
)
2 H 0 H -C(O)tBu
CH
2 tBu 243 Het 6 NH -CCH 3
)
2 H 0 H -C(O)Ph I H 2 tBu1 244 Het 6 NH -CCH 3
)
2 H 0 H -C(O)CH 2 Ph I H 2 tBuI 245 Het 6 0 -CCH 3
)
2 H 0 H -C(O)Ph I H 2 tBu 246 Het 7 0 -CCH 3
)
2 H 0 H -C(O)Ph
OCH
2 tBu 247 Het 7 0 -O(OH 3
)
2 H 0 H -O(O)tBu 01 I - CHAIU ______ I___________
___
81 No. Het" X Ra Rb E R 5
R
6 O Physical - -- .
properties 248 Het 8 0 -C(CH 3
)
2 H 0 H -C(O)Ph
CH
2 tBu 249 Het 9 0 -C(CH 3
)
2 H 0 H -C(O)Ph
CH
2 tBu 250 Hetl 5 0 -C(CH 3
)
2 H 0 H -C(O)Ph
CH
2 tBu 251 Het 15 NH -C(CH 3
)
2 H 0 H -C(O)Ph
CH
2 tBu 252 Het1 3 NH -C(CH 3
)
2 H 0 H -C(O)Ph
CH
2 tBu 253 Het 3 NH -C(CH 3
)
2 H 0 H -C(0)iPr Cl
CH
2 tBu 254 Het 6 NH 4-trifluoro- H 0 H -C(O)Ph methylphenyl 255 Het 6 NH 4-trifluoro- H 0 H -C(O)-2-methyl- I methylphenyl phenyl 256 Het' NH 4-trifluoro- H 0 H -C(O)tBu C1 methylpheny 257 Het 13 NH 4-trifluoro- H 0 H -C(O)Ph methylphenyl 258 Het 6 NH 4-fluorophenyl H 0 H -C(O)Ph 259 Het1 3 NH 4-methyl- H 0 H -C(O)Ph phenyl 260 Het 6 NH 4-methyl- H 0 H -C(O)Ph mp. 164*C phenyl 261 Hett 5 NH 4-methyl- H 0 H -C(O)Ph phenyl 262 Het 6 NH 4-methyl- H 0 H -C(O)tBu phenyl 263 Het 6 NH 4-isopropyl- H 0 H -C(O)tBu oxyphenyl 264 Het 6 NH 4-isopropyl- H 0 H -C(O)iPr oxypheny 265 Het 6 NH 4-isopropyl- H 0 H -C(O)Ph oxyphenyl 266 Het 6 NH 4-isopropyl- H 0 H -C(O)tBu Cl oxyphenyl 267 Het 6 NH 4-isopropyl- H 0 H
-C(O)C(CH
3 ) oxyphenyl
CH
2 268 Het 13 NH 4-isopropyl- H 0 H -C(O)Ph oxyphenyl 269 Het 7 NH 4-isopropyl- H 0 H -C(O)Ph oxyphenyl 270 Het 15 0 4-isopropyl- H 0 H -C(O)Ph oxyphenyl 271 Het 6 NH 4-ethoxy- H 0 H -C(O)Ph phenyl 272 Het 6 NH 4-ethoxy- H 0 H -C(O)iPr phenyl 82 No. Het" X Ra Rb E R 5
R
6 Q Physical properties 273 Het 6 NH 4-ethoxy- H 0 H -C(O)CH 2 Ph I phenyl 274 Het 15 NH 4-ethoxy- H 0 H -C(O)Ph I phenyl I 275 Het 15 0 4-ethoxy- H 0 H -C(O)iPr C phenyl 276 Het 15 NH 4-ethoxy- H 0 H -C(O)iPr I phenyl 277 Het 6 NH -C(CH 3
)
2 0H H 0 H -C(O)Ph I 278 Het1 5 NH -C(CH 3
)
2 0H H 0 H -C(O)Ph I 279 Het 6 NH -CH 2 0CH 2 H 0 H -C(O)Ph I
CH
3 _ 280 Het 6 NH -CH 2 0CH 3 H 0 H -C(O)Ph I 281 Het 6 NH -CH 2 0CH 2 H 0 H -C(O)iPr
CH
3 282 Het 15 NH -CH 2 0CH 2 H 0 H -C(O)Ph I
CH
3 I I 283 Het 15 NH -COOtBu H 0 H -C(O)Ph I 284 Het1 5 NH -COOtBu H 0 H -C(O)CH 2 Ph I 285 Het 6 NH -COOtBu H 0 H -C(O)Ph I 286 Het 6 NH -CON(CH 3 ) H 0 H -C(0)Ph I Ph _ 287 Het 15 NH -CON(CH 3 ) H 0 H -C(O)Ph I Ph 288 Het 13 NH -CON(CH 3 ) H 0 H -C(O)Ph I Ph 289 Het 9 NH -CON(CH 3 ) H 0 H -C(O)Ph Ph 290 Het 6 NH Ph H 0 -CH 3 -C(O)Ph I mp. 183*C 291 Het 6 NH Ph H 0 tBu -C(O)Ph I 292 Het 6 NH Ph H 0 -CH 2
CH
3 -C(O)Ph i 293 Het 6 NH tBu H 0 -CH 3 -C(O)Ph I mp. 169 173*C 294 Het 6 NH tBu H 0 nPr -C(O)Ph I 295 Het 6 NH tBu H 0 iPr -C(O)Ph I 296 Het 6 NH Ph H 0 -CH 3 -C(O)-2-methyl phenyl 297 Het 6 NH Ph H 0 H -C(0)cyclopropy I mp. 129*C 298 Het' NH tBu H 0 H -C(O)cyclopropyl I 299 Het' NH Ph H 0 H -C(O)cyclopropyl 1 300 Het' NH Ph H 0 -CH 3 -C(O)cyclopropyl 1 301 Het 16 NH tBu H 0 H -C(O)tBu I 302 Het 16 NH tBu - 0 H -C(O)tBu I
_________CH
3 ____ _______ ____ ____ 83 No. Hetn X Ra Rb E R 5
R
6 a Physical properties 303 Het 16 NH tBu H 0 H -C(O)Ph I 'H-NMR
(CDCI
3 ): 6 = 0.92 (s, 9H), 1.43 (t, 3H), 4.08 (m, 4H), 6.72 (s, 2H), 9.25 (s, 1H) 304 Het1 6 NH 4-fluorophenyl H 0 H -C(O)Ph _ 305 Het 16 NH 4-fluorophenyl H 0 H -C(O)tBu 1 306 Het 16 NH 4-fluorophenyl H 0 H -C(O)iPr I 307 Het 1 6 NH 4-fluorophenyl H 0 H -C(O)-2-pyridyl I 308 Het 1 6 NH Ph H 0 -CH 3 -C(O)Ph Cl 309 Het1 6 NH Ph H 0 H -C(O)tBu I 310 Het 1 6 NH Ph H 0 H -C(O)cyclopropyl I 311 Het1 6 NH Ph H 0 H -C(O)iPr Cl 312 Het 16 NH Ph H 0 H -C(O)Ph I 313 Het1 6 NH 2-thienyl H 0 H -C(O)tBu I 314 Het 16 NH 2-thienyl H 0 H -C(O)Ph 315 Het 16 NH 2-thienyl H 0 H -C(O)Ph Cl 316 Het1 8 NH -OCH 2
CH
3 H 0 H -C(O)Ph 317 Het1 8 NH -OSO 2
CH
3 H 0 H -C(O)Ph 318 Het 1 8 NH -OSO 2
CH
3 H 0 H -C(O)iPr 319 Het 18 NH -OS0 2
CH
3 H 0 H -C(O)tBu 320 Het 18 NH -OC(O)- H 0 H -C(O)Ph
N(CH
3
)
2 321 Het 18 NH -OCH 2
CH
3 H 0 H -C(O)Ph Cl 322 Het 18 NH -OSO 2
CF
3 H 0 H -C(O)Ph I 323 Het 1 8 NH -OC(O)- F 0 H -C(O)Ph
N(CH
3
)
2 324 Het 18 0 -OCH 2
CH
3 H 0 H -C(O)Ph I 325 Het 18 NH -OCH 2
CH
3 H 0 H -C(O)iPr 326 Het1 8 NH -OSO 2
CF
3 H 0 H -C(O)iPr I 327 Het' 8 NH -OSO 2
CF
3 H 0 H -C(O)iPr Cl 328 Het 8 NH -OCH 2
CH
3 H 0 H -C(O)tBu I 329 Het 18 NH -OCH 2
CH
3 H 0 H -C(O)tBu Cl 330 Het 18 NH -OC(O)- H 0 H -C(O)tBu
N(CH
3
)
2 331 Het 17 NH nPr H 0 H -C(O)iPr I 332 Het 17 NH nPr H 0 H -C(O)CH 2 Ph I 333 Het1 7 NH nPr H 0 H -C(O)C(CH 3 )= CH 2 Cl 334 Het 17 INH nPr H 0 H -C(O)Ph C 84 No. Hetn X Ra Rb E R 5 R6 0 Physical I - -properties 335 Het1 7 NH nPr H 0 H -C(O)Ph 336 Het 17 NH nPr H 0 CH 3 -C(0)Ph 337 Het 17 NH nPr H 0 H -C(0)tBu 338 Het 17 NH Ph H 0 H -C(0)tBu C1 339 Het 17 NH Ph H 0 H -C(O)tBu I mp. 72-78*C 340 He0 17 NH Ph H 10 H -C(0)iPr 341 Het 17 NH Ph H 0 H -C(O)Ph I mp. 73-82*C 342 Het 17 NH Ph H 0 H -C(0)Ph Cl 343 Het 17 NH Ph H 0 H *C(O)cyclopropyl I 344 Het' 7 NH Ph H NH H C(0)Ph Br 345 Het 17 NH tBu H 0 H -C(0)Ph 346 Het' 7 NH tBu H 0 H -C(0)tBu 347 Het 19 0 -OCH 2
CH
3 H 0 H -C(0)tBu 348 Het' 9 0 -OCH 2
CH
3 H 0 H -C(0)tBu Cl 349 Het' 9 0 -OCH 2
CH
3 H 0 H -C(0)Ph 350 Het 1 9 0 -OCH 2
CH
3 H 0 H -C(0)iPr 351 Het' 9 0 -OCH 2 Ph H 0 H -C(O)Ph 352 Het 19 0 -O(CH 2
)
2 H 0 H -C(O)Ph
OCH
3 O H 1C_ 353 Het2 9 0 -OCH 2 Ph H 0 H -C(O)Ph Cl 354 Hetf 0 0 -OCH 2 Ph H 0 H -C(O)Ph 355 Het2 0 0 -OCH 2 Ph H 0 H -C(0)tBu 356 Het 20 10 -OCH 2 Ph H 0 H -C(0)iPr 357 Het' 9 0 -OCH 2 Ph H 0 H *C(0)tBu C 358 Het 19 10 -OS 2
CH
3 H 0 H -C(O)Ph 359 Het 1 9 0 -OS0 2
CF
3 H 0 H -C(O)Ph 360 Het 19 0 -OCH 2
CH
3 H NH H -C(O)-4-tert- Br I _ _ Ibutylphenyl 361 Het 19 0 *OCH 2
CH
3 H 0 H -C(0)CH 2
CH
3 362 Het' 9 0 -O(CH 2
)
2 H 0 H -C(O)tBu
OCH
3 363 Het' 9 0 -O(CH 2
)
2 H 0 H -C(O)iPr I OCH 3 II 364 Het 20 0 -O(CH 2
)
2 H 0 H -C(0)Ph I OCH 3 1 ___ 365 Het 2 O 0 -O(CH 2
)
2 H 0 H -C(O)Ph Cl I OCH 3 1 ____ 366 Het 2 0 0 -OCH 2
CH
3 H NH H -C(0)Ph Cl 367 Het 2 0 0 -OCH 2
CH
3 H 0 H -C(0)Ph I 85 No. Het" X Ra Rb E R 5 R6 a Physical I I properties 368 Het 20 0 -OSO 2
CH
3 H 0 H -C(O)-3-pyridyl 1 369 Het 20 0 -OS02CH 3 H 0 H -C(O)-2-methyl- I I _phenyl 370 Het2O 0 -OS0 2
CF
3 H 0 H -C(0)-2,6 dimethyiphenyl 371 Het 6 NH =NOtBu H 0 H -C(O)Ph 372 Het 6 NH =NOtBu H 0 H -C(O)tBu 373 Het 6 NH =NOCH 2
CH
3 H 0 H -C(O)Ph Cl 374 Het' 5 NH =NOtBu H 0 H -C(O)Ph 375 Het 6 NH =NOCH 2 Ph H 0 H -C(O)Ph 376 Het 6 NH -O(CH 2
)
2 0- H 0 H -C(O)Ph 377 Het 6 NH -OCH 2 CH H 0 H -C(O)Ph (tBu)O 378 Het 6 NH -OCH 2 CH H 0 H -C(O)tBu (tBu)O 379 Het 13 NH -OCH 2 CH H 0 H -C(O)Ph (tBu)O 380 Het 6 NH -OCH 2 CH H 0 H -C(O)iPr (tBu)O 381 Het 6 NH -OCH 2 CH H 0 H -C(O)cyclohexyl I (Ph)O 382 Het 6 NH -OCH 2 CH H 0 H -C(O)tBu CI (Ph)O 383 Het 6 NH -OCH 2 CH H 0 H -C(O)tBu I (Ph)O 384 Het 6 NH -OCH 2 CH H 0 H -C(O)Ph (Ph)O 385 Het 6 NH -OCH 2 CH H NH H -C(0)iPr (Ph)O 386 Het 15 NH -OCH 2 CH H 0 H -C(0)tBu (Ph)O 387 Het' 3 NH -OCH 2 CH H 0 H -C(O)Ph (Ph)O- )Ph 86 Table 2 No. Het" X Ra Rb R 5
E-R
6 Q Physical I properties 388 Het 6 NH tBu H H 0 Br mp. 123*C -N 389 Het 5 NH Ph H H 0 Br --N N 390 Het 13 NH tBu H H 0 Br -NI N 0 391 Het 6 NH Ph H H 0 Br -N 0 392 Het 6 NH tBu H H 0 Br -N 0 393 Het 6 NH Ph H H 0 Br -- N 0 394 Het1 6 NH tBu H H 0 Br -N 0 395 Het 13 NH tBu H H O0 ______- N 87 No. Het" X Ra Rb R 5 E-R' Q Physical properties 396 Het 13 NH Ph H H 0 Br - N | 0 397 Het 6 NH Ph H H 0 Br - N | 0 398 Het 6 NH tBu H H 0 Br -N| 0 399 Het 6 NH tBu H H 0 Br -Nb 400 Het 6 NH Ph H H 0 Br -- N 401 Het 6 NH tBu H H 0 Br -N 402 Het 6 NH Ph H H 0 Br
-N
88 No. Het" X Ra Rb E R 5
R
6 Q Physical properties 403 Het 13 NH nPr H 0 H -C(O)tBu I mp. 1580C 404 Het 1 3 NH nPr H 0 H -C(O)iPr I mp. 131*C 405 Het 1 3 NH nPr H 0 H -C(O)Ph I mp. 88*C 406 Het 1 3 NH -C(CH 3
)
2 H 0 H -(CO)Ph I mp. 650C Et 407 Het 6 NH -C(CH 3
)
2 H 0 H -C(O)tBu I mp. 142*C Et 408 Het 13 NH -C(CH 3
)
2 H 0 H -C(O)tBu I mp. 1340C Et 409 Het 6 NH Ph H 0 H -C(0)-2,6- I mp. 1750C dichloro phenyl 410 Het 13 NH -C(CH 3
)
2 H 0 H -C(O)iPr I mp. 1470C Et 411 Het 13 NH iPr H 0 H -C(O)iPr I mp. 1360C 412 Het 1 3 NH iPr H 0 H -C(O)tBu I mp. 153*C 413 Het 6 NH tBu H 0 H -C(O)cyclo- I mp. 960C propyl 414 Het 6 NH Ph H 0 H -C(0)-4- I mp. 172*C methoxy phenyl 415 Het 6 NH tBu H 0 H -C(0)-4- I mp. 153*C methoxy phenyl 416 Het 6 NH tBu H 0 H -C(O)-4-tert- I mp. 142 butylphenyl 1510C 417 Het 6 NH Ph H 0 H -C(0)-4-tert- I mp. 1690C butylphenyl 418 Het 2 1 NH SiMe 3 H 0 H -C(O)Ph I mp. 232*C 419 Het 2 1 NH SiMe 3 H 0 H -C(O)tBu I mp. 200*C 420 Het 1 NH Ph H 0 CH 3 -C(O)Ph I mp. I I__II >200*C 421 Het 1 NH SiMe 3 H 0 H -C(0)tBu I mp. 1740C 422 Het 1 3 NH SiMe 3 H 0 H -C(0)tBu I mp. 1500C 89 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 10 preparation to be examined. After the solution has run off, the treated rice plants 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, 250C, 40 - 60% relative atmospheric 15 humidity). At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples No. 1 and 70 show an activity resulting in 90 - 100% mortality of the test species used. Example 2 20 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 com rootworm (Diabrotica undecimpunctata). After having been kept for 2 days 25 in a 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 No. 1 and 70 show an activity resulting in 90 100% mortality of the test species used. 30 Example 3 Germinated field bean seeds (Vicia faba) with radicles are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae). Plants and aphids are 90 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 3 and 6 days storage, the 5 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 Examples No. 1 and 70 causes a 90 - 100% mortality of the aphids. Example 4 10 Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 spider mites (Tetranychus urticae). The plant leaf and the spider mites are sprayed to run-off point with an aqueous 15 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 6 days storage, the mortality of the preparation on all stages of the spider mites is determined. At a concentration of 300 ppm (based on the content 20 of active compound), the preparations of Examples No. 1 and 70 cause a mortality of 90 - 100%. Example 5 25 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. After the nematode larvae have been continuously exposed for 2 days, the 30 percentage of the specimens which have ceased to move (been immobilized) owing to the effect of the preparation is determined by comparison with the untreated controls (percent nematicidal contact activity).
91 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 5 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 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 10 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 15 test, respectively, (based in each case on the content of active compound), the preparations of Example No. 1 had a 90 - 100% activity against the root gall nematode Meloidogyne incognita. *Example 6 20 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 leafworm (Spodoptera litoralis) are counted into a small beaker. 200 pl of an aqueous solution of the formulated preparation to be 25 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 30 (based on the content of active compound), the preparations of Examples No. 167,199,19, 35, 23,169,195,170, 39, 409, 53, 260, 49,175, 177, 193, 290, 140, 162, 158 and 388 effect a mortality of 90 - 100% among the larvae.
92 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 5 30, 24 hour old eggs of the tobacco budworm (Heliothis virescens) are dipped into an aqueous solution of the formulated preparation to be examined for about 5 seconds and subsequently placed in 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 250C in a climatized 10 chamber. After 6 days storage, the mortality of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples No. 167, 199, 19, 35, 23, 169, 195, 170, 39, 62, 41, 403,114,404,119,405,406,407,408,409,53,43,173,149,91,260, 15 410, 411,141, 130, 412, 297, 413, 49, 99, 87, 175, 45, 60, 57, 220, 219, 218,177,185,193,290,140,161,162,158,420,293,417,191,414,415, 416, 421, 422, 165, 339, 341 and 388 cause a mortality of 90 - 100%. Example 8 20 Germinated field bean seeds (Vicia faba) with radicles are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae). Plants and aphids are then dipped for 5 seconds into an aqueous solution of the formulated 25 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 preparations of 30 Examples No. 72, 2, 167, 199, 19, 35, 23, 169, 195, 170, 39, 62, 114, 404, 119, 407, 408, 409, 53, 43,173,149,91,260,410,411,141,130,412, 297, 49,175,45, 60, 57, 177,185,193,290,140,146,161,162,158,420, 293, 417, 191, 414, 416, 422 and 41 effect an aphid mortality of 90 100%.
93 Example 9 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 5 examined. After the solution has run off, the rice plants treated in this manner are placed in a Petri dish and populated with about 20 larvae (L3 stage) of the rice leafhopper species Nilaparvata lugens. The Petri dish is sealed and stored in a climatized chamber (16 hours of light/day, 250C, 40 - 60% relative atmospheric humidity). After 6 days storage, the mortality 10 among the leafhopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples No.72,2,167,68, 199, 388,19,35,23,169,195,170,39,62,403,114, 404, 119,405,406,407,408,409,53,43,173,149,91,260,410,411, 141,130,412,297,413,49,99,87, 175, 45, 60, 57, 220, 219, 218, 177, 15 185,193,290,162,158,420,293,417,191,414,415,416,421,419,422, 339, 341 and 41 effect a mortality of 90 - 100%. Example 10 20 A Petri dish, half of whose bottom is covered with filter paper and which 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 25 examined are pipetted onto the eggs, and the rest is pipetted onto the maize corn. The Petri dish is sealed and stored at about 250C in a climatized chamber. After 6 days storage, the mortality 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 30 compound), the preparations of Examples No. 70, 72, 2, 68, 199, 388, 19, 35, 23,169,195,170,39,62,403,114,404,119,405,406,407,408,409, 53, 43,173, 149, 91, 260, 410, 411,141, 130, 412, 297, 413, 49, 99, 87, 175, 45, 60, 57,185,290,140,146, 161,162,158,293,417,415,59,416, 421, 422, 339, 341 and 41 effect a mortality of 90 - 100%.
94 Example 11 Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into brown glass bottles filled with tap water and subsequently 5 populated with approximately 100 spider mites (Tetranychus urticae). Plant leaf and spider mites are 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 6 days 10 storage, the mortality 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 No. 72, 2, 167, 68, 199, 388, 19, 35, 23, 169,195,170,39,62,403,114,404,119,405,406,407,408,409, 53,43,173,149,91,260,410,411,141,130,412,297,413,49,99,175, 15 421, 419, 422, 165, 339, 341 and 41 effect a mortality of 90 - 100%. Example 12 Part A of the test (contact activity): Approximately 5000 recently hatched, 20 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 have been continuously exposed for 6 days, the percentage of the specimens which have ceased to move 25 (been immobilized) owing to the effect of the preparation is determined by comparison with the untreated controls (percent nematicidal contact activity). Part B of the test (soil-drench activity): For this test, the entire solution from 30 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 one third of the active compound content in part A of the test. After two 95 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 5 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), 10 the preparations of Examples No. 19, 35, 23, 169, 195, 409, 173, 149, 260, 130, 297, 175, 177, 185, 193, 290 and 170 have a 90 - 100% activity against the root gall nematode Meloidogyne incognita. Example 13 15 Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into brown glass bottles filled with tap water and then populated for 48 hours with adult white flies (Trialeurodes vaporariorum). After the leaves have been uniformly covered with eggs, they are sprayed to run-off 20 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 No. 199, 35, 195, 170, 62, 114, 409, 43 show an efficacy of 90 - 100%. 25 Example 14 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 30 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 sealed culture containers are stored at 230C, and after 4 days, the mortality 96 of the leafhopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Examples No. 62, 35, 114, 409, 53, 149 effect a mortality of 90 - 100% on the test species used. 5 Example 15 Oats (Avena sativa) which are densely populated by the oat grain aphid (Rhopalosiphum padi) are sprayed to run-off point with an aqueous 10 solution of the formulated preparation to be examined. The mortality of the 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 No. 199, 35, 195, 62, 114, 409, 53 effect a mortality of 90-100%. 15 Example 16 Field beans or bell pepper plants which are severely infested with the green peach aphid (Myzus persicae) are sprayed to run-off point with an 20 aqueous solution of the formulated preparation to be examined. The 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 Example No. 199, 35, 195, 62, 409, 53 effect a mortality of 90 - 100%. 25 Example 17 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 30 be examined. The Petri dish is then sealed with a lid. After 8 days storage at about 230C, 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 No. 199, 35, 195, 170, 62, 114, 409, 53, 149 effect a mortality of 97 90-100%. Example 18 5 Ten Li larvae of the codling moth (Carpocapsa pomonella) are placed in a Petri dish filled with culture medium. Culture medium and 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 about 230C, the effect of the preparation on the larvae is determined. At a 10 concentration of 300 ppm (based on the content of active compound), the preparations of Examples No. 199, 35, 195, 170, 114, 409, 53, 149 effect a larvae mortality of 90 - 100%. Example 19 15 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 20 is subsequently sealed with a lid. After 3 days storage at about 23*C, 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 No. 35, 195, 114, 409, 53, 149 effect a larvae mortality of 90- 100%. 25 Example 20 Ten L2 larvae of the Egyptian cotton leafworm (Spodoptera litoralis) are placed in a Petri dish whose bottom is covered with filter paper and which 30 contains about 5 ml of culture medium. Filter paper, culture medium and larvae are then sprayed with an aqueous solution of the formulated preparation to be examined. The Petri dish is subsequently sealed with a lid. After 4 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 98 of active compound), the preparation of Example No. 409 effect a larvae mortality of 90 - 100%. Use as fungicide 5 Examples 21-24 The compounds were tested for their activity against one or more of the following organisms: 10 Plasmopora viticola Erysiphe graminis f. sp. tritici Pyricularia oryzae Leptosphaeria nodorum 15 Aqueous solutions or dispersions of the compounds at the desired concentrations and a wetting agent were applied to leaves or stalks of the test plants. Plants or parts of plants were inoculated with the test pathogen in question and kept under controlled environmental conditions which are 20 suitable for plant growth and disease development. After a suitable period of 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 control or low-level control, 2 means medium-level control and 3 means good to complete control. At a concentration of 500 ppm (w/v) or 25 less, the following compounds scored 2 or more against the listed fungi. Plasmopora viticola: 68, 19, 35, 23, 169, 195, 170, 39, 62, 41 Erysiphe graminis: 72, 19, 35, 23, 169, 195, 170 30 Pyricularia oryzae: 23, 195, 170 Leptosphaeria nodorum: 68, 19, 35, 23, 169, 170, 39, 62, 41

Claims (21)

1. A compound of the formula I 5 Y-Z x R3() A 1 10 R2 D R 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, (Cl-C 4 )-alkyl, (C 1 C 4 )-haloalkyl or 30 (C 3 -C 5 )-cycloalkyl;
(4) R 2 and R 3 are identical or different and are each hydrogen, (Cl-C 4 )-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, 100 (Cl-C 8 )-trialkylsilylalkynyl, preferably dimethyl-(Cl-C 8 )-alkyl silylalkynyl, (Cl-C 4 )-alkoxy, (C-C 4 )-haloalkoxy, (CrC4) alkoxy-(C-C 4 )-alkyl, (Cl-C 4 )-haloalkoxy-(Cl-C 4 )-alkyl, (Cl C 4 )-alkoxy-(Cl-C 4 )-haloalkyl, (Cl C 4 )-haloalkoxy-(C-C4) 5 haloalkyl, halogen, amino, monosubstituted amino, disubstituted amino, hydroxyl, (C-C 4 )-hydroxyalkyl, (C 1 C4) alkanoyl, (C1-C4)-alkanoyl-(C 1 C 4 )-alkyl, (C 1 -C 4 )-halo alkanoyl, (C 3 -C 5 )-cycloalkyl, (C 3 -C 5 )-halocycloalkyl, cyano, (Cl-C 4 )-cyanoalkyl, nitro, (Cl-C 4 )-nitroalkyl, thiocyano, 10 (Cl-C 4 )-thiocyanoalkyl, (Cl-C 4 )-alkoxycarbonyl, (C1C4) alkoxycarbonyl-(Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkoxycarbonyl, (Cl-C 4 )-alkylthio, (C-C 4 )-alkylthio-(Cl-C 4 )-alkyl, (Cl C4) haloalkylthio, (Cl-C 4 )-alkylsulfinyl, (Cl-C 4 )-haloalkylsulfinyl, (Cl-C 4 )-alkylsulfonyl or (Cl 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-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, preferably trifluoromethyl, halogen, (C 1 -C 4 )-alkoxy or (C 1 -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-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-C 4 )-alkyl, (6) Y - Z together are a (C 1 C 20 )-hydrocarbon radical which is straight chain or branched and in which one or more, preferably up to three, 101 CH 2 may be replaced by hetero atom radicals such as 0, NR 1 O, S, SO, S02 or SiR 1 R 12 , where R 1 0 is hydrogen, (C 1 C 4 )-alkyl or (Cr-C 4 )-acyl, and Ri 1 and R1 2 are identical or different and are each independently of the other (Cl-C 4 )-alkyl, phenyl or substituted 5 phenyl, and where this (Cl-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 7 )-alkyl, (C 2 -C4)-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkenyl, 15 halogen, halo-(Cl C 4 )-alkyl, halo-(C-C 4 )-alkoxy, hydroxyl and (C 1 C 4 )-acyl; or, if not included in the above 20 definitions, (7) Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms which may be substituted by one or more, preferably up to three, identical or different radicals selected from the group 25 consisting of (C Cy)-alkyl, (C 2 -C 4 )-alkenyl, (C 3 -C 7 )-alkynyl, 30 (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkenyl, halogen, halo-(C-C 4 )-alkyl, halo-(CC - 4 )-alkoxy, 102 hydroxyl and (C 1 -C 4 )-acyl; and (8) Z is aryl or O-aryl, where aryl is preferably a naphthyl or phenyl 5 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 halogen, 10 (C 3 -C 8 )-cycloalkyl, (C 3 -C)-cycloalkenyl, phenoxy, substituted phenoxy, phenylthio, 15 substituted phenylthio, phenyl, substituted phenyl, NO 2 , 0 20 -C-R13 acetoxy, hydroxyl, cyano, 25 SiR 4 R 15 R 16 , 0-SiR 4 R 1 5 R 16 NR 17 R 18 S(O)R19, SO 2 R' ", 30 (CS-C 1 2 )-alkyl, (C2-C1 2 )-alkenyl, (C 1 -C 12 )-alkoxy and (C 1 -C 12 )-alkylthio; and 103 R1 3 is (C 1 -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; R 1 4 , R 15 and R1 6 are identical or different and are each 5 independently of one another (Cl-C 4 )-alkyl, phenyl and/or substituted phenyl; R 17 and R 18 are identical or different and are each independently of the other hydrogen, (Cl-C 4 )-alkyl and/or (Cl-C4)-acyl; 10 R' 9 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 -C12)-alkenyl one or more, preferably up to 3, CH 2 groups may be replaced by hetero atom radicals such as 0, 15 S, SO, SO2, NR' or SiR"R12'; R10', R' and R 12 ' have the meanings of R 1 0 , R", R 12 ; the (C-C 12 )-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-(Cl-C 4 )-alkoxy, hydroxyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C)-cycloalkenyl, (Cl C4) acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (Cl-C7) 25 alkoxy and (C-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,)-cycloalkenyl, phenoxy and substituted phenoxy; or, if not included in the above definitions, 104 (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 (Cl-C7-alkyl, (C2-C4)-alkenyl, (C-C7)-alkynyl, (C 3 -C)-cycloalkyl, 10 (C 3 -C)-cycloalkenyl, halogen, halo-(Cl-C 4 )-alkyl, halo-(Cl-C 4 )-alkoxy, hydroxyl and 15 (Cl-C 4 )-acyl; and (10) Z is (C 3 -C,)-cycloalkyl or (C 5 -C,)-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 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 25 (C-C 1 8 )-alkyl, (C 3 -C)-cycloalkyl, (C 3 -C 8 )-cycloalkoxy, (2-C1 8 )-alkenyl, (C2-C1 8 )-alkynyl, 30 (C-C 1 2 )-alkoxy, (C1-C 12 )-alkanoyloxy, formyl, (C2-C1 2 )-acyl, (C 1 -C 12 )-alkyl-oxycarbonyl, 105 SiR 21 R 22 R 23 NR 24 R 2 5 0 || 5 C-NR2R hydroxyl, halogen, aryl, heteroaryl, 10 O aryl, o heteroaryl, CH 2 0 aryl, CH 2 0 heteroaryl, (C1-C1 8 )-alkanediyldioxy, 15 (C 1 -0 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 (C01-C18)-, (C2-C18)-, (0-C12)-, (C2-C12)- and (C 1 -0 1 3 )-hydrocarbon radicals mentioned may be replaced by 20 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 R 10 ", R 11 " and 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 25 these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, 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; 106 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, (CrC 18 )-alkoxy, (C 3 -0s)-cycloalkyl and aryl, where in the (C-C 18 )-hydro carbon radicals more than one, preferably up to three, non adjacent CH 2 groups may be replaced by oxygen and where 10 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 in this case being a ring atom of this cycle, and where additionally these (C 1 -0 8 )-hydrocarbon 15 radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the cycloalkyl or cycloalkenyl radicals defined 20 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 II 30 X R where X1 independently of the other is sulfur or oxygen; Rz is hydrogen, (C-C 4 )-alkyl, trifluoromethyl or (C1C4)- 107 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, non-adjacent 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, (C1-C 4 )-alkyl, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-alkanoyl and R 27 and R 28 are each (C1-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 108 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 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, 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 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 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 109 substituents; (b) is a group of the formula III , Y 3 5 (y 2 )m(Z - Rq )n1 Y 1 N where 10 Yi, 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),R 30 - where I = 0 or 1 or a group of the formula CR 31 R 32 ; or Y1 or Y 3 stands in place of a direct bond, 15 where R 30 is hydrogen, (C-C 4 )-alkyl, (C 1 C 4 )-haloalkyl, (C2-04) alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 ) haloalkynyl, (C 1 C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, (Cl C 4 )-alkylthio, (Cl C 4 )-haloalkylthio, (Cl C4) 20 alkanoyl, (C 2 -C4)-haloalkanoyl, (C 3 -C 5 )-cycloalkyl, (Cl-C 4 )-alkylsulfonyl, (Cl-C 4 )-haloalkylsulfonyl, (C1 C 4 )-alkoxy-(C-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 25 alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C4)-haloalkenyl, (C2-C4) alkynyl, (C 2 -C 4 )-haloalkenyl, (C 3 -C 5 )-cycloalkyl, (C 1 -C 4 )-alkanoyl, (Cl-C 4 )-haloalkanoyl, (Cl C 4 )-alkoxy, (Cl C 4 )-haloalkoxy, (Cl-C 4 )-alkylthio or (Cl C4) haloalkylthio; 30 mi is 0, 1, 2, 3 or 4, preferably 1 or 2; ni is 0, 1, 2, 3 or 4, preferably 1 or 2; Z1 is a direct bond, NR 33 , 0, S(O)s where s = 0, 1 or 2, OSO 2 , S0 2 0, NR 34 SO 2 , S0 2 NR 35 , SiR 36 R 37 or 110 U-C-V, W where 5 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, cyano, nitro, (Cl-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, non-adjacent 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 20 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 1 R 43 , or Rq is aryl or heterocyclyl, where these two radicals may 25 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; Z'-Rq may combine with the carbon atoms to which they are attached to form a fused cycle having 4 to 6 ring atoms 30 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, (C 1 C 4 )-alkyl and oxo, or 111 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, preferably one CH 2 group, may be replaced by hetero 5 atom units such as oxygen, S(0)t where t = 0, 1 or 2 or NR45, where R 40 is hydrogen, (C 1 C 4 )-alkyl, (Cl-C 4 )-alkoxy or (C0-04) alkanoyl; 10 R 4 1 and R 42 independently of the other are each (C1C4) alkyl, preferably methyl; D' and D 2 are independent of each other and each is a direct bond, oxygen, S(O)k, S0 2 0, OS0 2 , CO, OCO, Coo, NR 46 , S0 2 NR 46 , NR 46 SO 2 , ONR 46 , NR 46 0, NR 46 CO, 15 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, (C0-C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl; R 47 and R 48 independently of the other are each (C1C4) alkyl; 20 R 43 and R 44 independently of the other are each hydrogen, cyano, nitro, halogen, (C-C)-alkyl, (Cl-C,)-haloalkyl, (C 2 -C)-alkenyl, (C 2 -C 8 )-haloalkenyl, (C 2 -C 8 )-alkynyl, (C 2 -C)-haloalkynyl, (C1-C 8 )-alkoxy-(C 1 -C 4 )-alkyl, ( 0 i-C 8 )-haloalkoxy-(Cl-C4)-alkyl, (Cl-C 8 )-alkylthio 25 (Cl-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 ) alkyl, aryl, heterocyclyl, aryl-(Cl-C 4 )-alkyl or heterocyclyl-(Cl-C 4 )-alkyl, where in the last 8 radicals 30 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 , or R43 and R 44 located at the same carbon atom together are 112 an oxo group, where R 49 is (C 1 -C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro or halogen; 5 R 45 is hydrogen, (C-C 8 )-alkyl, (Cl-C 4 )-haloalkyl, (C1C4) alkoxy, (Cl-C 4 )-alkylthio, (C 3 -C 5 )-cycloalkyl, (C2-C4) alkenyl, (C 2 -C 4 )-alkynyl, (Cl-C 4 )-alkanoyl, (C2-04) haloalkanoyl, (C 2 -C 4 )-alkoxyalkyl, phenyl-(Cl-C 4 )-alkyl or phenyl where the phenyl groups may be 10 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 5 0 is (Cl-C 4 )-alkyl, (Cl-C 4 )-haloalkyl, (Cl-C 4 )-alkoxy, (Cl-C4)-alkylthio, halogen or cyano; 15 or, if not included in the above definitions, (c) is a group of the formula IV .y 4 W 1 -R 20 Z2> Ru 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 25 system, where Ru is hydrogen, halogen, cyano, (Cl-C 4 )-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) 30 haloalkoxy, (Cl-C 4 )-alkanoyloxy, (Cl-C 4 )-haloalkanoyl oxy, (Cl-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-O- or -NR520-; Rt is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or 113 cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, non-adjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x where x = 0, 5 1 or 2, NR 53 or SiR 5 4 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 10 Rt may be aryl or heterocyclyl, where both of these radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D 4 R 57 , or Ru and Rt together form a three- to eight-membered ring 15 system which is spirocyclically linked to the ring 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 20 where R 51 is hydrogen, (C-C 4 )-alkyl, (C 1 C 4 )-haloalkyl, (C 2 -C 4 ) 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, (Cl-C4) 25 alkylthio-(Cl-C 4 )-alkyl, (Cl-C 4 )-alkoxycarbonyl, (C 1 -C 4 )-alkylsulfonyl, (C-C 4 )-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 30 maximum number) identical or different substituents R59, or R 51 is CON 6 0 R 6 1 where R 60 and R 6 1 independently of the other are each hydrogen, (C 1 -C 4 )-alkyl or phenyl, where the phenyl group may 114 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 (Cl-C4) 5 alkyl, (C 1 -C 4 )-haloalkyl, (C-C 4 )-alkoxy, (C1C4) haloalkoxy, (C-C 4 )-alkylthio or halogen; R 52 is hydrogen, (Cl C 4 )-alkyl, (C-C4)-alkanoyl or (C3-05) cycloalkyl; R 53 is hydrogen, (C 1 C 4 )-alkyl, (C-C 4 )-alkoxy or (C1C4) 10 alkanoyl; 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 15 unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R 63 ; R63 may be (Cl-C 4 )-alkyl, (C 1 C 4 )-haloalkyl, (Cl-C4) alkoxy, (C 1 C 4 )-haloalkoxy, cyano, nitro or halogen, 20 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 25 system, preferably the indane, 1,2,3,4 tetrahydronaphthalene, decalin or benzocycloheptane system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum 30 number) 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, S0 2 0, OS0 2 , CO, OCO, Coo, S0 2 NR 66 , NR 66 SO 2 , NR 66 0, ONR 66 , 115 NR 66 , NR 66 CO, CONR 66 or SiR 67 R 68 , where k = 0, 1 or2; and R 56 , R 57 , R 64 and R 65 independently of one another are each hydrogen, cyano, nitro, halogen, (Cl-C 8 )-alkyl, 5 (C-C)-haloalkyl, (C 2 -C)-alkenyl, (C 2 -C 8 )-haloalkenyl, (C 2 -C 8 )-alkynyl, (C 2 -C 8 )-haloalkynyl, (Cl-C 8 )-alkoxy (Cl-C4)-alkyl, (ClrC8)-haloalkoxy-(Cl-C4)-alkyl, (CI-C8)-alkylthio-(Cl-C4)-alkyl, (Cl-C8)-haloalkylthio (Cl-C 4 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, 10 (C 3 -C 8 )-cycloalkyl-(Cl-C 4 )-alkyl, (C 4 -C,)-cycloalkenyl (Cl-C 4 )-alkyl, aryl, heterocyclyl, aryl-(Cl-C 4 )-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 15 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, (Cl-C 4 )-alkanoyl or (C 3 -C 5 )-cycloalkyl and R 67 and R 68 independently of the other are each (C0-04) 20 alkyl, and R 69 independently of the others may be (Cl-C 4 )-alkyl, (Cl C 4 )-haloalkyl, (C 1 -C4)-alkoxy, (Cl-C 4 )-haloalkoxy, cyano, nitro, halogen, (Cl-C 4 )-alkanoyl or (C2-C4) haloalkanoyl, or two of the radicals 25 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; (13) R 4 and R 5 are identical or different and are each hydrogen, halogen, 30 (Cl-C2 0 )-alkyl with or without substitution, (C 2 -C 20 )-alkenyl with or without substitution, (C 2 -C 20 )-alkynyl with or without substitution, aryl, substituted aryl or (C 3 -C 8 )-cycloalkyl with or without substitution; 116 (14) E is oxygen, NR 70 , S(O)q where q = 0, 1 or 2, R 70 being hydrogen, (Cl C 4 )-alkyl, (Cl C 4 )-alkenyl or (Cl-C 4 )-acyl; (15) R 6 is (C-C 20 )-alkyl, (C 2 -C 20 )-alkenyl, (C 2 -C 20 )-alkynyl, (C1C20) 5 M haloalkyl, (C 3 -C,)-cycloalkyl, aryl or -C-R 7 , where M is oxygen or sulfur and R 7 1 is (Cl-C 20 )-alkyl, (C 2 -C2 0 )-alkenyl, (C 2 -C 20 )-alkynyl, aryl, heterocyclyl, (Cl C 20 )-haloalkyl, 10 (C 2 -C 20 )-haloalkenyl, (C 2 -C 20 )-haloalkynyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-halocycloalkyl, (C 5 -C 8 )-cycloalkenyl, (C5-C8) halocycloalkenyl and where, if not included in the definitions above, in the (C1C20)- and (C 2 -C 20 )-hydrocarbon radicals mentioned under (13) and (15) one or more, preferably up to 15 three, non-adjacent CH 2 groups may be replaced by a carbonyl group or by hetero atom radicals such as 0, S(O)x where x = 0, 1 or 2, NR 10 "' or SiR 1 "'R ", where R 10 "', R' and R 12 " have the meanings of R 10 , R" and R1 2 and where additionally 3 to 6 carbon atoms of these hydrocarbon 20 radicals may form a cycle and where these hydrocarbon radicals with or without the abovementioned 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 25 hydroxyl, alkyl, halogen, haloalkyl, cycloalkyl, acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio and NR 72 R 73 , where aryl is as defined under (8), where the heterocyclyl radicals listed may be unsubstituted or substituted by up to three (in the case of 30 fluorine up to the maximum number) identical or different radicals and where R 72 and R 73 independently of the other are each hydrogen, (Cl-C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C1C8) acyl, aryl, heteroaryl or benzoyl; or 0 35 11 117 (16) if E is NR 70 and R 6 is -C-R 71 , R 70 and R 7 1 together are also (C 3 -C 6 )-alkanediyl, where a CH 2 group adjacent to the nitrogen may be replaced by CO and/or where ethanediyl may be replaced by ethenediyl or 5 o-phenylene, preferably (C 3 -C 6 )-alkanediyl, -CO-CH 2 -CH 2 -, -CO-CH=CH- or -- C 2. A compound of the formula I as claimed in claim 1, 10 in which A is CH and D is N*R 15 or A is nitrogen and D is N*R; Q"~ is an inorganic or organic anion such as Hal~, NO 3 ~, BF4~, BPh 4 ~ or 20 PFel R 1 is hydrogen, methyl, fluorine or chlorine; R 2 and R 3 are each hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C2-C4) alkynyl, amino, (C1-C 4 )-alkylamino, (C1-C 4 )-dialkylamino, trimethyl silylethynyl, methoxycarbonyl, (C 1 -C 4 )-haloalkyl, (C2-C4) 25 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 unit; or 30 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. 118 3. A compound of the formula I as claimed in claim 1, in which Y is a bond or a methylene group which is substituted by one or two, preferably by one, (C 1 -C 4 )-alkyl radical; and Z is (C 3 -C)-cycloalkyl or (C 5 -C 8 )-cycloalkenyl, where a CH 2 group of 5 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,)-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 10 consisting of (C1-C,8)-alkyl, (C 3 -C)-cycloalkyl, (C 3 -C)-cycloalkoxy, 15 (C 2 -C1 8 )-alkenyl, (C2-C18 )-alkynyl, (CCC12)-alkoxy, (C-C1 2 )-alkanoyloxy, formyl, 20 (C 2 -C 1 2 )-acyl, (Cl -C1 2 )-alkyl-oxycarbonyl, SiR 21 R 22 R 2 3 , NR 24 R 25 , 0 25 14 C-NR 24 R 25 , hydroxyl, halogen, aryl, 30 heteroaryl, 0 aryl, 0 heteroaryl, CH 2 0 aryl, CH 2 0 heteroaryl, 119 (C,-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 5 in the (C-C1)-, (C2-C18)-, (C1-C12)-, (C2-C12)- and (C1C-3) hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as 0, NR 1 O" or SiR 11 "R 12 ", these hetero atom radicals preferably not being adjacent to one another, where R 10 ", R 11 and R 12 " have the meanings of R 10 , R 11 , R 12 and where additionally 3 to 10 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, 15 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) identical or 20 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, (Cl C 4 )-acyl, (C 3 -C)-cycloalkyl, phenyl and substituted phenyl and where R 21 , 25 R 22 , R 23 are identical or different and are each independently of the others (C-C 8 )-alkyl, (0-C 8 )-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 where 3 to 6 carbon atoms of these hydrocarbon radicals may form 30 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 (C 1 -0 8 )-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of 120 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 (C5-C8) cycloalkenyl radicals defined above may be cis or trans with respect 5 to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1,4 position, preference is given to the cis configuration; or Y is a bond; and 10 Z (a) is a group of the formula Il X1 RY X> (II) 15 where X 1 is oxygen; RY is (C-C 20 )-alkyl, (C 2 -C2 0 )-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 (in the case of fluorine up to the maximum number) identical 20 or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, non adjacent 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 30 maximum number), identical or different radicals selected from the group consisting of halogen, preferably fluorine, aryl, aryloxy, arylthio, (0 3 -C 8 )-cycloalkoxy, (C 3 -C 8 )-cycloalkylthio, heterocyclyl, heterocyclyloxy or (Cl-C 2 )-alkoxycarbonyl, where the where the cycloaliphatic, aromatic or heterocyclic 121 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, 5 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, S(O)n where n = 0, 1 or 2 or NR 10 where R 29 is hydrogen, (0 1 -C 8 )-alkyl, (Cl-C)-alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system 15 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, (0 3 -C,)-cycloalkyl, aryl or aryl-(C 1 -C 4 )-alkyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among 20 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 further benzene ring or cyclohexane ring, forms a 25 condensed ring system, preferably the indane, 1,2,3,4 tetrahydronaphthaline, 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 30 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 122 Rz is hydrogen or (b) is a group of the formula (Ill) 5 , Y 3 (y 2 ) M1(Zi - Rq )WiIII where 10 Y 1 , Y 2 and Y 3 are each a group of the formula -O-, -S(O)r-, where r = 0, 1 or 2 or is a group of the formula CR 31 R 32 , or Y1 or y3 stand in place of a direct bond, where R 31 and R 32 independently of the other are each hydrogen or methyl; 15 m 1 is 1 or 2; ni is 1 or 2; Z1 is a direct bond, NR 33 , 0, S(0), where s = 0, 1 or 2, OS0 2 , S0 2 0, NR 34 S0 2 , S0 2 NR 35 , S1R 36 R 37 or U-C-V, where 11 20 W U is a direct bond, NR 38 or 0; W is oxygen; V is a direct bond, NR 39 or oxygen; and 25 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; Rq independently of the others is (Cl-C 8 )-alkyl where one or 30 more, preferably up to three, non-adjacent saturated carbon units may be replaced by oxygen and which, with or without the variations mentioned, may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D 1 R 43 , or 123 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 ; 5 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 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 R 46 independently of the others is hydrogen, (Cl-C 4 )-alkyl, 10 (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, (C 1 C 8 )-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 15 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, (C1C4) haloalkyl, (Cl C 4 )-alkoxy, (Cl C 4 )-haloalkoxy, cyano, nitro, 20 halogen; or, (c) is a group of the formula IV y4 W1-Rt 25 __C zK2 Ru(IV) where 30 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; W 1 is a direct bond, oxygen, -CO-, -COO-, CONR 52 , sulfur, -C=N-, -C=N-0- where R 52 is hydrogen, (Cl-C 4 )-alkyl, 124 (C-C 4 )-alkanoyl and (C 3 -C 5 )-cycloalkyl, and Rt is as defined above under (12 c). 4. A compound of the formula I as claimed in any of claims 1 to 3, in 5 which R' is hydrogen; R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3) alkenyl, amino, (Cl-C 4 )-alkylamino, (Cl-C 4 )-dialkylamino, (C2-03) chloro- or -fluoroalkenyl, (C 2 -C 3 )-alkynyl, trimethylsilylethynyl, 10 (C 1 -C 3 )-chloro- or -fluoroalkyl, methoxymethyl, halogen or cyano; or R 2 and R 3 together with the ring system to which they are attached form the quinazoline or quinoline system, which may be fluorine substituted in the carbocyclic moiety; or R 2 and R 3 together with the carbon atoms to which they are attached form 15 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 which 20 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 cyclohexyl, 1,4-substitution is preferred, the substituents 25 being cis to one another; or (b) is a group of the formula 11 X RY 30 X z) X Rz where X1 is oxygen; Rz is hydrogen; 125 or (c) is a group of the formula III - y 3 (Y 2 ) 5 ~ 1 ( Z' - Rq ) n lI where Y 1 is CH 2 ; Y 2 is CH2 10 Y 3 is CH 2 , 0 or a direct bond; mi is 1 or (d) is a group of the formula IV y4 W1-Rt 15 1 Z R(IV) Cz 2 Ru where Y 4 is a direct bond or CH 2 ; 20 Z 2 is oxygen; Ru is hydrogen or methyl. 6. A compound of the formula I as claimed in any of claims 1 to 5, in which 25 A is CH and D is N*R or A is nitrogen and D is N*R; Qn is an inorganic or organic anion such as Ha[, NO 3 ~, BF4~, BPh 4 ~, 30 PF6l R 4 is hydrogen, halogen or methyl; R 5 is hydrogen, halogen, (C 1 C- 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C)-alkynyl, phenyl, substituted phenyl or (C 3 -C 8 )-cycloalkyl; E is oxygen, NR 70 , S(O)q where q = 0, 1 or 2, where R 70 is hydrogen, 126 methyl or acetyl; R 6 is (C0-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (Cl-C 4 )-haloalkyl, (C 3 -C 6 )-cyclo M || 5 alkyl, phenyl or -C-R 7 , where M is oxygen or sulfur and R 71 is (C C)-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, aryl, heterocyclyl, (Cl C 8 )-haloalkyl, (C 2 -C 8 )-haloalkenyl, (C 2 -C)-haloalkynyl, (C3-C6) cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 5 -C)-cycloalkenyl, (C5-C6) halocycloalkenyl and where the hydrocarbon radicals mentioned 10 may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of alkyl, haloalkyl, cycloalkyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl and NR 72 R 73 , where aryl is as defined under (8), where the heterocyclyl radicals mentioned may be unsubstituted or 15 substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where R 72 and R 73 independently of the other are each hydrogen, (C-C)-alkyl, (C 2 -C)-alkenyl, (C-C,)-acyl, aryl, heteroaryl or benzoyl; or 0 20 || if E is NR 70 and R 6 is -C-R 71 , R 70 and R 71 together are also (C 3 -C 6 )-alkanediyl, where a CH 2 group adjacent to the nitrogen may be replaced by CO and/or where ethanediyl may be replaced by ethenediyl or 25 o-phenylene, preferably (C 3 -C 6 )-alkanediyl, -CO-CH 2 -CH 2 -, -CO-CH=CH- or - C 0 30
7. A compound of the formula I as claimed in any of claims 1 to 6, in which R 1 is hydrogen; R 2 is ethyl or methoxymethyl; R 3 is chlorine, bromine or methoxy, preferably those for which R 2 is 35 ethyl and R 3 is chlorine; 127 X is NH; R 4 is hydrogen; R 5 is hydrogen or (0 1 -C 8 )-alkyl; E is oxygen or NR 70 , where R 70 is hydrogen; 5 M Re is -C-R 71 , where M is oxygen.
8. A process for preparing compounds of the formula I as claimed in 10 any of claims 1 to 7, which comprises reacting a compound of the formula (V) X-Y-Z R3 G (V) 15 R 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) 20 L E , 6 R (VI) R 4 R5 where R 4 , R 5 , R 6 and E are each as defined under formula I and L is a 25 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 anions. 30
9. A composition comprising at least one compound as claimed in any of claims 1 to 7 and at least one formulating agent.
10. A fungicidal composition as claimed in claim 9, comprising a fungicidally effective amount of at least one compound as claimed in any of 35 claims 1 to 7 together with the additives or auxiliaries which are customary 128 for this application.
11. An insecticidal, acaricidal or nematicidal composition as claimed in claim 9, comprising an effective amount of at least one compound as 5 claimed in any of claims 1 to 7 together with the additives or auxiliaries which are customary for these applications.
12. A crop protection composition comprising a fungicidally, insecticidally, acaricidally or nematicidally effective amount of at least one 10 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, together with the auxiliaries and additives which are customary for this application. 15
13. A composition for use in protecting wood or as a preservative in 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 20 auxiliaries and additives which are customary for these applications.
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. 25
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. 30
16. The use of a compound as claimed in any of claims 1 to 7 or a 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 129 preservative or as a preservative in sealing compounds, in paints, in cooling lubricants for metalworking or in drilling and cutting oils.
18. A method of controlling phytopathogenic fungi, which comprises 5 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 and 13 to these fungi or to the plants, areas or substrates infested with them or to seed. 10
19. A method of controlling insect pests, acarids and nematodes, which comprises applying an 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, 11 and 12 to these insect pests, acarids and nematodes or to the plants, areas or substrates infested with them. 15
20. 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, 11 and 12 for controlling insect pests, acarids and nematodes. 20
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 claims 9, 10, 12 and 13.
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EP0432894A1 (en) * 1989-12-07 1991-06-19 Ube Industries, Ltd. Fungicidal composition
DE4005178A1 (en) * 1990-02-19 1991-08-22 Henkel Kgaa New alkylamino-1-N-alkyl-pyridinium salts - are antimicrobial agents useful against bacteria, yeasts and fungi, e.g. Candida albicans
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