EP0981518A1 - Heterocycles d'azote substitues, procedes permettant de les preparer et leur utilisation comme agents de lutte contre les parasites - Google Patents

Heterocycles d'azote substitues, procedes permettant de les preparer et leur utilisation comme agents de lutte contre les parasites

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Publication number
EP0981518A1
EP0981518A1 EP98921486A EP98921486A EP0981518A1 EP 0981518 A1 EP0981518 A1 EP 0981518A1 EP 98921486 A EP98921486 A EP 98921486A EP 98921486 A EP98921486 A EP 98921486A EP 0981518 A1 EP0981518 A1 EP 0981518A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
radicals
hydrogen
halogen
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98921486A
Other languages
German (de)
English (en)
Inventor
Ralf Braun
Harald Jakobi
Wolfgang Schaper
Gerhard Krautstrunk
Martin Märkl
Herbert Stark
Oswald Ort
Ulrich Sanft
Maria-Theresia Thönessen
Manfred Kern
Werner Bonin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Hoechst Schering Agrevo GmbH
Aventis CropScience GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst Schering Agrevo GmbH, Aventis CropScience GmbH filed Critical Hoechst Schering Agrevo GmbH
Publication of EP0981518A1 publication Critical patent/EP0981518A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N43/48—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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to new substituted pyridines and pyrimidines and condensed systems derived therefrom, processes for their preparation and their use as pesticides and fungicides.
  • AN + R and D means nitrogen, in which
  • Q n is any inorganic or organic anion, where n is 1, 2, 3 or 4;
  • R 1 is hydrogen, halogen, (CC 4 ) -alk 1, (C r C 4 ) -haloalkyl or
  • R 2 is hydrogen, (C 1 -C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl,
  • R 3 is hydrogen, (C r C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4 ) -Alkynyl, (C 2 -C 4 ) -haloalkynyl, (C r C 8 ) - trialkylsilylalkynyl, preferably dimethyl- (C r C 8 ) -alkyl-silylalkynyl, (C r C 4 ) -alkoxy, (C r C 4 ) haloalkoxy, (CC alkoxy-CC C alkyl), (C r C 4 ) haloalkoxy, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C r C 4 ) - haloalkoxy ⁇ CC
  • R 2 and R 3 together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered isocyclic ring which, if it is a 5-ring, instead of CH 2, represents an oxygen or sulfur atom or which, if it is a 6-ring, can contain one or two nitrogen atoms instead of one or two CH units and which is optionally substituted by 1, 2 or 3 identical or different radicals and these radicals (C ⁇ C ⁇ alkyl, (C r C 4 ) haloalkyl, preferably Trifluoromethyl, halogen, (C 1 -C 4 ) alkoxy or (CC 4 ) haloalkoxy; or R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered isocyclic ring which can contain oxygen and / or sulfur instead of one or two CH 2 groups and which is optionally substituted by 1, 2 or 3 (C 1 -C 4 ) alkyl groups;
  • R 8 and R 9 are independently hydrogen or (C 1 -C 4 ) alkyl.
  • Y - Z together means a (0, -0 20 ) hydrocarbon radical which is unbranched or branched and in which one or more, preferably up to three, CH 2 by heteroatom units such as O, NR 10 , S, SO, SO 2 or SiR 11 R 12 can be replaced, where R 10 is hydrogen, (C r C 4 ) alkyl or (C r C 4 ) acyl, and R 11 and R 12 , which are the same or different, independently of one another ( C 1 -C 4 ) -Alkyl, phenyl or substituted phenyl, and this (CC j r -hydrocarbon radical with the possible above-mentioned variations optionally with one or more, preferably up to three identical or different radicals from the series
  • Y is a bond or a divalent hydrocarbon chain with 1 to 6 carbon atoms, optionally with one or more, preferably up to three identical or different radicals from the series
  • Z means aryl or O-aryl, with aryl preferably one
  • Is naphthyl or phenyl group optionally with one or more, preferably up to five, in particular up to three identical or different radicals from the series
  • R 13 (C r C 7 ) alkyl, halogen - ⁇ - C ⁇ alkyl, (C 3 -C 7 ) cycloalkyl, halogen -
  • R 14 , R 15 and R 16 are identical or different and independently of one another are (C 1 -C 4 ) alkyl, phenyl and / or substituted phenyl;
  • R 17 and R 18 are the same or different and independent of each other
  • R 19 represents (C 1 -C 10 ) alkyl, phenyl or substituted phenyl
  • Y is a bond or a divalent hydrocarbon chain with 1 to 6
  • (10) Z is (C 3 -C 8 ) cycloalkyl or (C 5 -C 8 ) cycloalkenyl, where a CH 2 group of the carbocycle can be replaced by NR 20 ;
  • R 20 is phenyl or substituted phenyl and the (C 3 -C 8 ) cycloalkyl or (C 5 -C 8 ) cycloalkenyl radical, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number same or different residues from the series
  • (C 2 -C 18 ) alkylidene are substituted and, if not covered by the above definitions, in the (C r C 18 ) -, (C 2 -C 18 ) -, (C ⁇ C ⁇ ) -, ( C 2 -C 12 ) and (CC 13 ) hydrocarbon radicals one or more, preferably up to three, CH 2 groups can be replaced by heteroatom units such as O, NR 10 " or SiR 11" R 12 " and these heteroatom units are preferably not adjacent, where R 10 " , R 11" and R 12 "have the same meaning as R 10 , R 11 , R 12 and, moreover, 3 to 6 C atoms of these hydrocarbon radicals can form a cycle and these hydrocarbon radicals with or without these variations, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals from the series hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl,
  • Heteroaryl can be unsubstituted or can be provided with up to three, in the case of fluorine also up to the maximum number, of identical or different substituents;
  • Aryl has the meanings as under (8);
  • R 24 and R 25 are identical or different and independently of one another are hydrogen, (C r C 4 ) -alkyl, (C 1 -C 4 ) -acyl, (C 3 -C 6 ) -cycloalkyl, phenyl and substituted phenyl and R 21 , R 22 , R 23 are the same or different and independently of one another denote (CC 18 ) alkyl, (CC 18 ) alkoxy, (C 3 -C 8 ) cycloalkyl and aryl, in which (CC 18 ) - hydrocarbon Residues of several, preferably up to three non-adjacent CH 2 groups can be replaced by oxygen and 3 to 6 carbon atoms of these hydrocarbon residues form a cycle can, whereby two of the carbon residues bonded to the silicon (for example R 1 and R 22 ) can together form a cycle, as a result of which the silicon atom is then a ring atom of this cycle and moreover these (C 1 -C 4
  • Z (a) represents a group of the formula II
  • w -orinr X 1 independently of one another denotes sulfur or oxygen
  • R z represents hydrogen, (C 1 -C 4 ) alkyl, trifluoromethyl or (C r C 4 ) alkoxy; or
  • Y 1 or Y 3 are in place of a direct bond
  • R 30 is hydrogen, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) - Alkynyl, (C 2 -C 4 ) haloalkynyl, (C 1 -C 4 alkoxy, (C r C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C r C 4 ) haloalkylthio, (C 1 -C 4 ) Alkanoyl, (C 2 -C 4 ) haloalkanoyl, (C 3 -C 5 ) cycloalkyl, (C 1 -C 4 ) alkylsulfonyl, (C r C 4 ) haloalkylsulfonyl, (C r C 4 ) - Alkoxy
  • R 31 and R 32 independently of one another are hydrogen, hydroxy
  • R 36 and R 37 are (C r C 4 ) alkyl or phenyl, preferably methyl;
  • U is a direct bond, NR 38 or O;
  • W represents oxygen or sulfur, preferably oxygen
  • V represents a direct bond, NR 39 or oxygen,
  • R 33 , R 34 , R 35 , R 38 and R 39 are the same or different and each represents hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
  • R q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D 2 R 44 , or two adjacent radicals
  • Z 1 -R q together with the C atoms carrying these can form a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group of O, S and N and which is unsubstituted or by one or more radicals from the Group of halogen, (C 1 -C 4 ) alkyl and oxo is substituted, or
  • R 40 is hydrogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy or (C, -C 4 ) alkanoyl;
  • R 41 and R 42 independently of one another are (C r C 4 ) -alkyl, preferably methyl;
  • R 46 is independently hydrogen, (CC 4 ) alkyl, (CC 4 ) alkanoyl or (C 3 -C 5 ) cycloalkyl;
  • R 47 and R 48 independently of one another are (CC 4 ) -alkyl
  • R 43 and R 44 independently of one another are hydrogen, cyano, nitro,
  • R 43 and R 44 together on the same C atom mean an oxo group
  • R 49 is (C r C 4 ) alkyl, (CrC ⁇ haloalkyl, (C 1 -C 4 ) alkoxy, (C r C 4 ) haloalkoxy, cyano, nitro or halogen;
  • R 45 is hydrogen, (C r C ⁇ ) ⁇ alkyl. (C r C 4 ) haloalkyl, (C r C 4 ) alkoxy, (C r C 4 ) alkylthio, (C 3 -C 5 ) cycloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) -alkynyl, (C r C 4 ) -alkanoyl, (C 2 -C 4 ) -haloalkanoyl, (C 2 - C 4 ) -alkoxyalkyl, phenyl- (CC 4 ) -alkyl or phenyl and the phenyl groups unsubstituted or with up to three, in the case of fluorine also up to the maximum number of identical or different substituents R 50 , where
  • R 50 represents (C-CJ-alkyl, (C r C 4 ) -haloalkyl, (C r C 4 ) -alkoxy, (C r C 4 ) -alkylthio, halogen or cyano; or, if not covered by the above definitions ,
  • Y 4 is direct bond or CH 2 ;
  • R u hydrogen, halogen, cyano, (C r C 4 ) alkyl, (C r C 4 ) -
  • Haloalkyl (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) - Cycloalkyl, (C 4 -C 6 ) cycloalkenyl, (C ⁇ C ⁇ alkoxy, (C r C 4 ) haloalkoxy, (C r C 4 ) alkanoyloxy, (C r C 4 ) haloalkanoyloxy, (CC 4 ) Alkylthio or (C r C 4 ) haloalkylthio;
  • R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or
  • R ' can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine up to a maximum number of identical or different radicals D 4 R 57 , or
  • R 51 is hydrogen, (C r C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) -Alkynyl, (C 2 -C 4 ) - haloalkynyl, (C r C 4 ) -alkoxy, (C r C 4 ) -alkanoyl, (C 2 -C 4 ) - haloalkanoyl, (C r C 4 ) -alkoxy- (C r C 4 ) alkyl, (C r C 4 ) alkylthio- (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl, (C ⁇ C ,,) - alkylsulfonyl, (CC 4 ) -Halogenalkyl
  • R 51 means CONR ⁇ R 61 , wherein
  • R 60 and R 61 independently of one another are hydrogen, (C r C 4 ) -alkyl or phenyl, where the phenyl group can be unsubstituted or substituted by up to three, in the case of fluorine also up to the maximum number of identical or different substituents R 62 , and
  • R 62 and R 59 independently of one another (C ⁇ C ⁇ -Alky !, (C r C 4 ) -
  • Haloalkyl (C r C 4 ) alkoxy, (C r C 4 ) haloalkoxy, (C r C 4 ) alkylthio or halogen;
  • R 52 represents hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkanoyl or (C 3 -C 5 ) cycloalkyl;
  • R 53 represents hydrogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy or (C r C 4 ) alkanoyl;
  • R 54 and R 55 independently of one another are (C 1 -C 4 -alkyl, preferably methyl;
  • R 58 is hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or Heteroaryl means, the latter 3 radicals being unsubstituted or having up to three, in the case of fluorine, up to the maximum number of identical or different substituents R 63 ;
  • R 63 (C r C4) alkyl, (C r C 4) haloalkyl, (C r C4) alkoxy, (C r C 4) - may be haloalkoxy, cyano, nitro or halogen, and for R Ring system u and R 'formed may be unsubstituted or may be provided with up to three, but preferably one, substituent D 5 R 64 , or the ring system formed from R u and R * together with a further benzene ring or cyclohexane ring forms a condensed ring system, preferably indane -, 1, 2,3,4- tetrahydronaphthalene, decalin or benzocycloheptane system and the benzene ring in these condensed systems unsubstituted or with up to three, in the case of fluorine also up to the maximum number of identical or different substituents D 6 R 65 can be provided, wherein
  • R 56 , R 57 , R 64 and R 65 are each independently hydrogen
  • Alkanoyl or (C 3 -C 5 ) cycloalkyl and R 67 and R 68 independently of one another are (C, -C 4 ) alkyl, and R 69 independently of one another are (C 1 -C 4 ) alkyl, (C r C 4 ) Haloalkyl,
  • R * is hydrogen
  • R 53 is hydrogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy or (C r C 4 ) alkanoyl and
  • R 54 and R 55 independently of one another are (C 1 -C 4 ) -alkyl, preferably methyl;
  • R 58 is hydrogen, (C r C 8 ) -alkyl, (d-C ⁇ J-alkanoyl, benzoyl, aryl or heteroaryl, the latter 3 radicals being unsubstituted or with up to three, in the case of fluorine also up to the maximum number of the same or various substituents R 63 can be provided, and
  • R 83 can be (C r C 4 ) alkyl, (C ⁇ C ⁇ haloalkyl, (CrC alkoxy, (C r C 4 ) haloalkoxy, cyano, nitro or halogen), and that formed from R u and R l Ring system unsubstituted or with up to three, but preferably one, substituent D 5 R 64 , or the ring system formed from R u and R * together with a further benzene ring or cyclohexane ring forms a condensed ring system, preferably the indane, 1, 2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system and the benzene ring in these condensed systems can be unsubstituted or can be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents D 6 R 65 , where among the compounds for which the carbon atom between Y 4 and
  • R 66 are independently hydrogen, (CC 4 ) alkyl, (CC 4 ) alkanoyl or (C 3 -C 5 ) cycloalkyl and
  • R 56 , R 57 , R 64 and R 85 are each independently hydrogen
  • R 89 can independently be (dC ⁇ alkyl, (C r C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, cyano, nitro, halogen, or two of the Leftovers
  • R 56 , R 57 , R 64 , R 65 , R 69 which are located on the same C atom, together and each independently represent an oxo group
  • R 4 represents hydrogen, halogen, (C r C 4 ) alkyl
  • R 5 hydrogen, halogen, CN, nitro, (C r C 4 ) alkoxycarbonyl, (C r C 4 ) -
  • Alkylcarbamoyl, di (C 1 -C 4 ) alkylcarbamoyl, (C r C 8 ) alkoxy, (C r C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) - Alkynyl, aryl or (C 3 -C 8 ) -cycloalkyl means, where aryl is as defined under (8) and, if not covered by the above definitions, the carbon radicals mentioned under (13) and (14) optionally with one or more , preferably up to three, in the case of halogen up to the maximum number, may be substituted on identical or different radicals from the series halogen, cycloalkyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl; R 6 is aryl or heteroaryl, optionally with one or several, preferably up to three, in the case of halogen up to
  • R 38 and R 3T are (CC 4 ) alkyl or phenyl, preferably methyl;
  • U represents a direct bond, NR 38 ' or O;
  • W represents oxygen or sulfur, preferably oxygen
  • V represents a direct bond, NR 39 ' or oxygen,
  • R 33 ' , R 34' , R 35 ' , R 38' and R 3ff are the same or different and each represents hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
  • R q ' denotes aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ⁇ R 44' , or two adjacent radicals Z 1 ' -R q ' together with the carbon atoms bearing these can form a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group of O, S and N and which is unsubstituted or substituted by one or more radicals from the group of halogen, (C ⁇ C ⁇ alkyl and oxo, or
  • R 40 ' is hydrogen, (C r C 4 ) alkyl, (C, -C 4 ) alkoxy or (C 1 -C 4 ) alkanoyl;
  • R 41 ' and R 42' independently of one another are (CC 4 ) -alkyl, preferably methyl;
  • D 1 ' and D 2' are each independent and direct
  • R 46 * is independently hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkanoyl or (C 3 -C 5 ) cycloalkyl;
  • R 47 " and R 48 ' independently of one another are (C r C 4 ) alkyl
  • R 43 ' and R 44' are independently hydrogen, cyano, nitro, halogen, (C r C 8 ) alkyl, (C r C 8 ) haloalkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) alkynyl, (C 2 -C 8 ) haloalkynyl, alkyl, (C r C 8 ) haloalkoxy- (C r C 4 ) alkyl, (C 1 -C 8 ) alkylthio- (C 1 -C 4 ) alkyl, (CC ⁇ haloalkylthio-fCrC ⁇ alkyl , (C 3 -C 8 ) cycloalkyl, (C 4 -C 8 ) cycloalkenyl, (C 3 -C 8 ) cycloalkyl- (C r C 4 )
  • R 43 ' and R 44' sitting on the same C atom together mean an oxo group
  • R 49 ' is (CC 4 ) alkyl, (C r C 4 ) haloalkyl, (dC ⁇ alkoxy, (C r C 4 ) haloalkoxy, cyano, nitro or halogen;
  • R 45 ' is hydrogen, (C 1 -C 4 -alky !, (C r C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy,
  • An inorganic anion is an anion of an inorganic acid, such as, for example, F “ , CI “ , Br “ , I “ , NO 3 “ , SO 4 2 -, HSO 4 “ , PO 4 3 “ , HPO 4 2” , H 2 PO 4 “ , PO 3 3” or N 3 " , or a complex anion such as BF 4 " , PF 6 " or tetraphenylborate.
  • An organic anion means an anion of an organic acid (carboxylic acid, sulfonic acid, phosphonic acid and the like) or an aromatic or heteroamatic phenolic compound.
  • organic acid carboxylic acid, sulfonic acid, phosphonic acid and the like
  • aromatic or heteroamatic phenolic compound an organic acid (carboxylic acid, sulfonic acid, phosphonic acid and the like) or an aromatic or heteroamatic phenolic compound.
  • These are, for example, anions of monofunctional or bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, propionic acid, maleic acid, Succinic acid, glycolic acid, oxalic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and also sulfonic acids such as p-toluenesulfonic acid, dodecylsulfonic acid or 1,5-naphthalenedisulfonic acid, or sac
  • a and D are part of a pyrimidine system, it is assumed that A is nitrogen and DN + R. However, it cannot be ruled out with absolute certainty that the remainder R is in the 3 position (ie that AN + R and D are nitrogen).
  • Z is (C 3 -C 8 ) -cycloalkyl or (C 5 -C 8 ) -cycloalkenyl, it is preferably with one or more, preferably up to 3 identical or different substituents from the series (C ⁇ C ⁇ J- Alkyl, (C 3 -C ") cycloalkyl, (C 3 -C 8 ) cycloalkyl- (C 1 -C 4 ) alkyl, (CrC ⁇ J-alkoxy, (C 3 -C 8 ) - cycloalkoxy, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 3 -C 8 ) cycloalkyl- (C r C 4 ) alkoxy, TrKC C ⁇ J-alkylsilyl, preferably dimethyl- (C r C 8 ) alkylsilyl or triethylsilyl, di- (CC 8 ) -alky
  • A represents nitrogen and DN + R;
  • Q n " is an anion such as shark ' , NO 3 -, BF 4 ' , BPh 4 " or PF 6 " ;
  • R 1 is hydrogen, methyl, fluorine or chlorine
  • R 2 is hydrogen, (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl,
  • Y is a bond or a methylene group which is optionally substituted with one or two, preferably with a (CC 4 ) -alkyl radical; and Z represents (C 3 -C 8 ) cycloalkyl or (C 5 -C 8 ) cycloalkenyl, it being possible for a CH 2 group of the carbocycle to be replaced by NR 20 ; R 20 is phenyl or substituted phenyl and the (C 3 -C 8 ) cycloalkyl or (C 5 -C 8 ) cycloalkenyl radical, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number same or different residues from the series
  • Aryl has the meanings as under (8);
  • R 24 and R 25 are the same or different and are independent of each other
  • (C r C 4 ) alkyl, (C r C 4 ) acyl, (C 3 -C 6 ) cycloalkyl, phenyl and substituted phenyl and R 21 , R 22 , R 23 are identical or different and independently of one another denote the meaning (C 1 -C 18 ) -alkyl, (C 1 -C 18 -alkoxy, (C 3 -C 8 ) -cycloalkyl and aryl, where in the (CC 18 ) - hydrocarbon radicals several, preferably up to three CH 2 groups can be replaced by oxygen and 3 to 6 carbon atoms of these hydrocarbon radicals can form a cycle, two of the hydrocarbon radicals bonded to the silicon (for example R 21 and R 22 ) also together forming a cycle can form, whereby the silicon atom can optionally be part of this cycle and also these (C r C 18 ) hydrocarbon radicals with or without the variations, optionally with one or more in the case of hal
  • Z (a) represents a group of formula II
  • R y is (C r C 20 ) alkyl, (C 2 -C 20 ) alkenyl, (C 2 -C 20 ) alkynyl, aryl or heterocyclyl, the aryl or heterocyclyl radicals listed being unsubstituted or with up to three, in the case of fluorine can also be provided up to the maximum number of identical or different radicals and in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by heteroatom units, such as oxygen or SiR 27 R 28 , where R 27 and R 28 are (C 1 -C 4 ) alkyl, preferably methyl, and in addition 3 to 6 atoms of these optionally modified hydrocarbon as above Residues can form a cycle and these hydrocarbon residues with or without the specified variations, optionally with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different
  • R 31 and R 32 are independently hydrogen or methyl; m 1 represents 1 or 2; n 1 represents 1 or 2;
  • U is a direct bond, NR 38 or O;
  • W represents oxygen
  • V represents a direct bond, NR 39 or oxygen
  • R 36 and R 37 are (C 1 -C 4 ) alkyl or phenyl, preferably methyl;
  • R 33 , R 34 , R 35 , R 38 and R 39 are the same or different and each
  • R q independent of each other means in which one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by oxygen, and with or without the stated variations, optionally with one or more, preferably up to three, in the case of fluorine to Maximum number of identical or different radicals D ⁇ 43 can be substituted, or
  • R q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D 2 R ⁇ .
  • D 1 and D 2 are each independent of one another and a direct bond
  • R 46 is independently hydrogen, (C 1 -C 4 ) alkyl, (CC 4 ) alkanoyl or (C 3 -C 5 ) cycloalkyl;
  • R 43 and R 44 independently of one another are hydrogen, halogen, preferably fluorine, (C r C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, aryl or heterocyclyl, the cycloaliphatic, aromatic or heterocyclic in the latter 3 radicals Ring systems can be unsubstituted or can be provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents R 49 , where
  • R 49 independently of one another (C 1 -C 4 -alkyl, (CC 4 ) -haloalkyl, (C r C 4 ) - Can be alkoxy, (C r C 4 ) haloalkoxy, cyano, nitro, halogen; or,
  • Y 4 represents a direct bond or CH 2 ;
  • Z 2 represents oxygen
  • Means -C NO- and R 52 is hydrogen, (C r C 4 ) -alkyl, (C r C 4 ) -
  • Alkanoyl and (C 3 -C 5 ) cycloalkyl means, and R 4 is as defined under (12 c) above.
  • R 1 represents hydrogen
  • R 2 is hydrogen, methyl, ethyl, propyl, methoxy, (C 2 -C 3 ) alkenyl, (C 2 -C 3 ) chlorine or
  • Fluorine may be substituted; 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;
  • R 1 represents hydrogen
  • R 2 is methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (CC 2 ) fluoroalkyl or
  • R 3 Means methoxymethyl; R 3 fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C ⁇ C j J-fluoroalkyl, amino,
  • Form quinazoline system which can be substituted with a fluorine atom.
  • X represents NH
  • Z denotes (a) cyclopentyl or cyclohexyl, where both radicals can optionally be substituted as above under (10) and, in the case of cyclohexyl, the 1,4-substitution is preferred, the substituents being in the cis position relative to one another; or
  • X 1 represents oxygen
  • R z represents hydrogen
  • Y 1 represents CH 2 ;
  • Y 2 represents CH 2 ;
  • Y 4 represents a direct bond or CH 2 ;
  • Z 2 represents oxygen
  • R u represents hydrogen or methyl
  • Z (a) means cyclohexyl, optionally as above in (10), but preferably with a radical from the series
  • Residues one or more, preferably up to three, CH 2 groups can be replaced by heteroatom units, such as O or SiR or R 12 " , where R 11" and R 12 "have the same meaning as R 11 , R 12 and beyond 3 to 6 carbon atoms these hydrocarbon residues
  • Heteroaryl can be unsubstituted or can be provided with up to three, in the case of fluorine also up to the maximum number, of identical or different substituents;
  • Aryl has the meanings as under (8);
  • R 24 and R 2S are the same or different and independent of each other
  • (CC 4 ) -alkyl, phenyl and substituted phenyl and R 21 , R 22 , R 23 are identical or different and independently of one another are (CC 8 ) -alkyl, (CC 8 ) -alkoxy, (C 3 - C 8 ) -
  • Cycloalkyl and aryl mean, in which in the (CC 8 ) hydrocarbon Residues of several, preferably up to three, CH 2 groups can be replaced by oxygen and 3 to 6 carbon atoms of these hydrocarbon residues can form a cycle, the silicon atom optionally being part of this cycle and moreover this (C ⁇ C ⁇ hydrocarbon radicals with or without the variations, optionally with one or more in the case of halogen up to the maximum number of identical or different radicals from the series halogen, haloalkyl, cycloalkyl, or (b) a group of the formula (II) means
  • X 1 represents oxygen
  • R 2 represents hydrogen
  • R y is (C 1 -C 15 ) alkyl, aryl or heterocyclyl in the sense of heteroaromatic ring system, the aryl or heterocyclyl radical being unsubstituted or having up to three, in the case of fluorine, up to the maximum number of identical or different radicals can be provided and in the alkyl radical mentioned one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by oxygen, and in addition 3 to 8 atoms of this optionally modified alkyl radical can form a cycle and this alkyl radical with or without the specified variations, optionally with one or more halogen atoms, in the case of fluorine also up to the maximum number may be provided on the same or different substituents, and the substituents X and R y on the heteroaliphatic six-membered ring are preferably cis to one another; or (c) denotes a group of the formula (IM),
  • n 1 represents 1 or 2;
  • R q is independent of one another means in which one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by oxygen, and with or without the stated variations, optionally with one or more, preferably up to three, in the case of fluorine to Maximum number of identical or different radicals D ⁇ 3 can be substituted, or
  • R q can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D 2 R ⁇ ; or (d) represents a group of formula IV
  • R u represents hydrogen
  • R 4 means (C r C 8 ) -alkyl in which one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by oxygen, and which can be substituted with or without the specified variations, optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number of identical or different radicals D 3 R 56 , or R 4 aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals DR 57 .
  • A represents nitrogen and DN + R;
  • Q represents an inorganic or organic anion such as shark “ , NO 3 " , BF 4 “ , BPh 4 “ , PF 6 “ ;
  • R 4 represents hydrogen;
  • R 5 is hydrogen, halogen, cyano, (C 1 -C 8 ) alkoxy, (C r C 8 ) alkyl, (CC 8 ) -
  • Haloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) alkynyl means;
  • R 6 denotes aryl or heteroaryl, the aryl and heteroaryl radicals optionally having one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals
  • Z 1 ' is a direct bond, O, OSO 2 or U'-CV, where i W
  • W represents oxygen
  • V represents a direct bond, NR 39 ' or oxygen
  • R 39 ' is hydrogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, (C r C 4 ) alkanoyl or (C 3 -C 5 ) - Means cycloalkyl;
  • R q ' are mutually independent substituents and is (C CjoJ-alkyl or (C 2 -C 20 ) alkenyl and optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number of identical or different radicals D r R 43 ' may be substituted, or
  • R q ' is halogen, hydroxy, nitro or cyano, or
  • R q ' can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ⁇ R 44' ;
  • R 46 * is independently hydrogen, (CC 4 ) alkyl, (C 1 -C 4 ) alkanoyl or (C 3 -C 5 ) cycloalkyl;
  • R 43 ' and R 44' independently of one another are hydrogen, halogen, preferably fluorine,
  • R 49 independently of one another means (C 1 -C 4 ) alkyl, (CC 4 ) haloalkyl, (C r C 4 ) alkoxy, (CC 4 ) haloalkoxy, cyano, nitro, halogen.
  • R 1 represents hydrogen
  • R 2 represents ethyl or methoxymethyl
  • R 3 is chlorine, bromine or methoxy, preferably those for which R 2 is ethyl and R 3
  • R 4 means hydrogen
  • R 5 means hydrogen
  • R 6 denotes aryl or heteroaryl, where the aryl and heteroaryl radicals may optionally be substituted by one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals Z 1 ′ -R q ′ , where
  • Z 1 ' is a direct bond, O or U'-CV, lw
  • W represents oxygen
  • V represents a direct bond, NR 39 ' or oxygen
  • R 39 ' is hydrogen, (C 1 -C 4 ) alkyl, (C r C 4 ) alkoxy, (C 1 -C 4 ) alkanoyl or (C 3 -C 5 ) cycloalkyl;
  • Z 1 ' -R q " together represent halogen, nitro or cyano, or
  • R q ' are mutually independent substituents and is (C r C 12 ) -alkyl or (C 2 -C 12 ) -alkenyl and optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number of the same or different R 43 ' radicals can be substituted, or
  • R q ' can mean aryl or heterocyclyl, where these two radicals can be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals D ⁇ R 44' ;
  • R 46 is independently hydrogen, (C 1 -C 4 ) alkyl, (C r C 4 ) alkanoyl or (C 3 -C 5 ) cycloalkyl;
  • R 43 ' and R 44' independently of one another are hydrogen, cyano, nitro, halogen, preferably fluorine, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, aryl or heterocyclyl, where in the latter 3 Residues the cycloaliphatic, aromatic or heterocyclic ring systems can be unsubstituted or provided with up to three, in the case of fluorine also up to the maximum number of identical or different substituents R 49 ' , where
  • R 49 ' are independently (C ⁇ C alkyl, (C r C 4) haloalkyl, (CC 4) - alkoxy, (CC haloalkoxy, cyano, nitro, can be halogen.
  • the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the carbon skeleton can each be straight-chain or branched.
  • the lower carbon skeletons e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl etc., mean e.g.
  • Alkynyl means e.g. Propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
  • Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, e.g. Cyclopropyl, cyclopentyl or cyclohexyl, but also bicyclic systems, such as e.g. the norbornyl group or the bicyclo [2.2.2] octane radical;
  • Halogen means, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkyl, -alkenyl and -alkynyl are partially or completely substituted alkyl, alkenyl or alkynyl, for example monohalogenalkyl, perhalogenalkyl, CF 3 , CHF 2 , CH by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine 2 F, CF 3 CF 2 , CH 2 FCHCI, CCI 3 , CHCI 2 , CH 2 CH 2 CI;
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 CI; corresponding applies to haloalkenyl and other halogen-substituted radicals.
  • a hydrocarbon residue is a straight chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon residue, e.g. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl; a hydrocarbon radical is preferably 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 to a hydrocarbon residue in a hydrocarbonoxy residue.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, ie heteroatoms or ring members, which also include substituted heteroatoms, preferably from the group N, O, S, SO, SO 2 ; it is preferably an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms and contains 1, 2 or 3 hetero units.
  • oxo groups can also occur on the hetero ring atoms, which can exist in different oxidation states, 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, mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents being, for example, one or more, preferably 1, 2 or 3 radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in
  • radicals with carbon atoms those with 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
  • Substituents from the group halogen for example fluorine and chlorine, (C 1 -C 4 alkyl, preferably methyl or ethyl, (C 1 -C 4 ) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 alkoxy, preferably methoxy or Ethoxy, (C 1 -C 4 ) haloalkoxy, nitro and cyano, the substituents methyl, methoxy and chlorine being particularly preferred.
  • Mono- or disubstituted amino means a chemically stable radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; there are alkyl residues with 1 up to 4 carbon atoms preferred;
  • Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (C 1 -C 4 ) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group halogen, (C 1 -C 4 ) alkyl, (C r C 4 ) alkoxy, (C 1 - C 4 ) haloalkyl, (CC 4 ) haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and - Trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
  • An acyl residue means the residue of an organic acid, for example the residue of a carboxylic acid and residues derived therefrom, such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the residue of carbonic acid monoesters, optionally N-substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
  • acyl means formyl, alkylcarbonyl such as [(C 1 -C 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic acids.
  • radicals in each case in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy;
  • substituents in the phenyl part are the substituents already mentioned above generally for substituted phenyl.
  • dimethyl (CC 8 ) alkylsilylethynyl is, for example, trimethylsilylethynyl or tert-butyldimethylsilylethynyl-
  • Halogen atoms preferably fluorine or chlorine, are replaced; under the expression "(C 2 -C 12 ) haloalkanoyl" a (C 1 -C 20 ) alkanoyl group in which the hydrogen atoms are partially, in the case of fluorine, completely
  • Halogen atoms preferably fluorine or chlorine, are replaced; under the term "cyano (C 1 -C 4 ) alkyl" a cyanoalkyl group whose
  • Alkoxycarbonyl group in which one or more, in the case of fluorine optionally also all hydrogen atoms, by halogen, preferably fluorine or
  • Chlorine are replaced; under the expression "(CC 4 ) -haloalkylthio" a (C 1 -C 4 ) -alkylthio group in which one or more, in the case of fluorine, optionally all hydrogen atoms of the hydrocarbon part are replaced by halogen, in particular chlorine or fluorine are; under the expression “(C r C 4 ) alkylsulfinyl", for example the methyl, ethyl, propyl,
  • Halogenoalkylsulfonyl (CC 4 ) alkylsulfinyl and sulfonyl radicals with the meanings given above, in which one or more, in the case of fluorine, optionally also all the hydrogen atoms of the hydrocarbon part
  • Halogen especially chlorine or fluorine are replaced; for example, under the expression "(C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl"
  • Methoxymethyl or ethoxymethyl group a 3-methoxypropyl group or one
  • Alkoxy- (CC 4 ) -alkyl radicals with the meanings given above, in which one or more, in the case of fluorine, if appropriate also all the hydrogen atoms of the corresponding hydrocarbon moieties, have been replaced by halogen, preferably chlorine or fluorine; under the expression "(C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl" for example
  • arylthio e.g. the phenylthio or the 1- or
  • 2-naphthylthio group under the term "aryloxy” e.g. the phenoxy or 1- or 2-naphthyloxy
  • heterocyclyloxy or “heterocyclylthio” one of the abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom
  • cycloalkoxy or "cycloalkylthio” one of the above Cycloalkyl radicals which are linked via an oxygen or sulfur atom
  • aroyl for example the benzoyl, naphthoyl or biphenylcarbonyl
  • Nicotinoyl, thienylacetyl or the pyridine propionyl group under the expression "(C 3 -C 8 ) cycloalkoxycarbonyl", for example the cyclobutyloxycarbonyl,
  • Naphthoxycarbonyl or the biphenyloxycarbonyl group under the expression "hetercyclyloxycarbonyl”, for example the tetrahydropyran-4-oxycarbonyl group; under the expression “(C 1 -C 20 ) alkanoyloxy”, for example formyloxy, acetoxy,
  • alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, non-adjacent saturated carbon units by a carbonyl group or can be replaced by heteroatom units, such as oxygen, S (O) x , with x 0, 1 or 2, NR 26 or SiR 27 R 28 , where R 26 is hydrogen, (C r C 4 ) -alkyl, (C r is C 4 ) -alkoxy or (C 1 -C 4 ) -alkanoyl and R 27 and R 28 are (C 1 -C 4 ) -alkyl, preferably methyl, and furthermore 3 to 12 atoms of these optionally modified as above Hydrocarbon radicals can form a cycle and these hydrocarbon radicals with or without the specified variations, optionally with one or more, preferably up to three, in the case of fluorine up to the maximum number of identical or different radicals from the series halogen, aryl,
  • Alkoxyalkyl radicals such as e.g. the methoxymethyl, methoxyethyl or ethoxyethyl
  • Alkoxy-alkoxy-alkyl radicals such as e.g. the methoxy or the ethoxy ethoxyethyl
  • Alkylthioalkyl radicals such as, for example, the methyl or the ethylthioethyl group; or Alkylsulfinyl-alkyl radicals, such as, for example, the methyl or ethylsulfinylethyl group; or
  • Alkylsulfonyl-alkyl radicals such as e.g. the methyl or ethylsulfonylethyl group; or
  • Alkyl-dialkylsilyl-alkyl preferably alkyl-dimethylsilyl-alkyl radicals, such as e.g. the
  • Trimethylsilylmethyl or the trimethylsilylethyl group Trimethylsilylmethyl or the trimethylsilylethyl group
  • Trialkylsilyl preferably alkyldimethylsilyl, e.g. the trimethylsilyl,
  • Cycloalkyldialkylsilyl preferably cycloalkyldimethylsilyl, such as e.g. the
  • Aryldialkylsilyl preferably aryldimethylsilyl residues such as e.g. the
  • Arylalkyl dialkylsilyl preferably aryldimethylsilyl residues such as e.g. the
  • Alkanoylalkyl residues such as e.g. the acetylmethyl or pivaloylmethyl group; or
  • Cycloalkanoylalkyl residues such as e.g. the cyclopropylcarbonylmethyl or the
  • Halogenalkanoylalkyl residues such as e.g. the trifluoro or trichloroacetylmethyl group; or
  • Aroylalkyl residues such as e.g. the benzoyl or naphthoylalkyl residues such as e.g. the
  • Heterocyclylcarbonylalkyl residues such as e.g. the thienyl or pyridylacetylmethyl
  • Aryl-alkyl residues e.g. the benzyl, the 2-phenylethyl, the 1-phenylethyl, the
  • Heterocyclylalkyl residues e.g. the thienylmethyl, pyridylmethyl, furfuryl,
  • Aryloxyalkyl radicals such as e.g. the phenoxymethyl or naphthoxymethyl group.
  • Cycloalkyl residues monocyclic such as cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, cycloheptyl or cyclooctyl radical
  • bicyclic such as, for example, the norbomyl radical or the bicyclo [2,2,2] octane radical or condensed like the decahydronaphthyl radical;
  • Alkyl-cycloalkyl residues such as e.g. the 4-methyl or the 4-tert-butylcyclohexyl group or the 1-methylcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group; Cycloalkyl-alkyl residues such as e.g. the cyclohexylmethyl or ethyl group; or also haloalkyl derivatives of the corresponding groups, such as, for example, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkylcycloalkyl or halocycloalkyl radicals. The same applies to similar definitions.
  • CH 2 groups or saturated carbon units which are replaced by heteroatom units are preferably not adjacent.
  • the compounds of the formula I have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers can therefore occur.
  • the invention encompasses both the pure isomers and their mixtures.
  • the mixtures of diasteromers can be prepared using conventional methods, e.g. be separated into the components by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by conventional methods, e.g. by salt formation with an optically active acid, separation of the diastereomeric salts and release of the pure enantiomers using a base.
  • the invention further relates to a process for the preparation of compounds of the formula I, which is characterized in that a compound of the formula (V)
  • R 4 , R 5 , R 6 and E have the meaning given under formula I and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, preferably halogen, optionally with the addition of salts such as AgBF 4 , AgNO 3 or NaI and the anion of the compounds obtained in this way, if necessary, analogously to known methods [eg Liebigs Ann. Chem. 1978, 1937; Methods of Org. Chemie / Houben-Weyl (D. Klamann, Ed.), 4th edition, Vol. E16a, Part 2, S 1008 ff, Thieme, Stuttgart 1990] replaced by other anions.
  • salts such as AgBF 4 , AgNO 3 or NaI
  • the above reaction is carried out in a temperature range from 20 to 150 ° C, optionally in an inert organic solvent such as acetonitrile, acetone, 2-butanone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one , Dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, Ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene. Mixtures of the solvents mentioned can also be used.
  • 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-
  • the compounds of formula (V) required as starting products are largely known from the literature [e.g. DE-A-4438 807, WO-A-96 11 913, WO-A-96 11 924, DE-4 343 250, WO-A-95 07 890, WO-A-9421 613, DE-A-4208254] or can be prepared analogously to known methods.
  • the active ingredients are suitable for good plant tolerance and cheaper
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros 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., Eutetranychus spp ..
  • Thysanura e.g. Lepisma saccharina.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
  • Cacoecia podana Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp ..
  • Oestrus spp. Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
  • Siphonaptera e.g. Xenopsylla cheopsis, Ceratophyllus spp ..
  • Arachnida e.g. Scorpio maurus
  • Latrodectus mactans From the class of the helminths e.g. Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis as well as Fasciola.
  • Gastropoda e.g. Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp ..
  • Bivalva e.g. Dreissena spp ..
  • the plant-parasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such 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) as well as the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratususchatatus), such as Pratususchatatus, and Pratylenchat
  • the genera Radopholus such as Radopholus similis
  • Pratylenchus such as Pratususchatatus
  • Pratususchatatus such as Prat
  • Tylenchulus such as Tylenchulus semipenetrans
  • Tylenchorhynchus such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni
  • Rotylenchus such as Rotylenchus robustus
  • Heliocotylenchus such as Haliocotylenchus multicinctus
  • Belonoaimus long such as Belonatusitidor Long
  • Xiphinema like Xiphinema index
  • the compounds of the invention can also be used to combat the nematode genera Ditylenchus (stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes such as Aphelenchoides ritzemabosi) and Anguina (flower nematodes such as Anguina tritici).
  • Ditylenchus stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor
  • Aphelenchoides leaf nematodes such as Aphelenchoides ritzemabosi
  • Anguina flower nematodes such as Anguina tritici
  • the invention also relates to compositions, in particular insecticidal and acaricidal compositions, which contain the compounds of the formula I in addition to suitable formulation auxiliaries.
  • the agents according to the invention generally contain 1 to 95% by weight of the active compounds of the formulas I.
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • SC oil or water-based dispersions
  • SE Suspoemulsions
  • SE dusts
  • DP pickling agents
  • water-dispersible granules WG
  • ULV formulations, microcapsules, waxes or baits.
  • the necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also wetting agents, for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, for example sodium lignosulfonate, 2,2'-dinaphthylmethane-6, Contain 6'- disulfonic acid sodium.
  • wetting agents for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, for example sodium lignosulfonate, 2,2'-dinaphthylmethane-6, Contain 6'- disulfonic acid sodium.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons.
  • alkylarylsulfonic acid calcium salts such as cadodecylbenzene sulfonate
  • 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 or ester polyesters, polyoxyacetyl sorboxate, polyoxyacetyl sorboxate, polyoxyacetyl sorboxate, polyoxyacetyl sorboxate, polyoxyacetyl sorboxate, polyoxyacetyl sorboxate, polyoxyacetyl sorboxate, polyoxyacetyl oresorbate, polyoxyacetyl sorboxate, polyoxyacetyl oresorbate, polyoxyacetyl sorboxate, polyoxyacetyl oresorbate, polyoxyacetyl sorboxate, polyoxyacety
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite, pyrophyllite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • the active ingredient concentration in wettable powders is, for example, about 10 to 90% by weight, the remainder to 100% by weight consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 5 to 80% by weight. Dust-like formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%. In the case of granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulation aids, fillers, etc. are used. In addition, the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • the concentrates present in the commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules using water. Dust-like and granulated preparations as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate varies. It can fluctuate within wide limits, e.g. between 0.0005 and 10.0 kg / ha or more of active substance, but is preferably between 0.001 and 5 kg / ha.
  • the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms, etc.
  • Preferred mixing partners are
  • the active substance content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active compounds according to the invention are also suitable for combating endoparasites and ectoparasites in the veterinary field or in the field of animal husbandry.
  • the active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, drinkers, granules, by dermal use in the form of, for example, dipping (dipping), spraying (spraying), pouring on (pour-on and spot) -on) and the pump and by parenteral use in the form of, for example, the injection.
  • the new compounds of formula I according to the invention can accordingly also be used particularly advantageously in livestock farming (e.g. cattle, sheep, pigs and poultry such as chickens, geese, etc.)
  • livestock farming e.g. cattle, sheep, pigs and poultry such as chickens, geese, etc.
  • the animals are given the new compounds, if appropriate in suitable formulations (see above) and if appropriate with the drinking water or feed orally. Since excretion in the faeces is effective, the development of insects in the faeces of the animals can be prevented very easily in this way.
  • the appropriate dosages and formulations depend in particular on the type and stage of development of the livestock and also on the infestation pressure and can be easily determined and determined using the usual methods.
  • the new compounds can e.g. in doses of 0.01 to 1 mg / kg body weight.
  • the compounds of the formula I according to the invention are also notable for an excellent fungicidal action.
  • Fungal pathogens that have already penetrated into the plant tissue can be successfully combated curatively. This is particularly important and advantageous in the case of those fungal diseases which can no longer be effectively combated with the usual fungicides after infection has occurred.
  • the spectrum of activity of the claimed compounds covers various economically important phytopathogenic Fungi such as Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Pyricularia oryzae, Pyrenophora teres, Leptosphaerea nodorum and Pellicularia sasakii and Puccinia recondita.
  • the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking or as preservatives in drilling and cutting oils.
  • the active compounds according to the invention can be used in their commercially available formulations either alone or in combination with other fungicides known from the literature.
  • fungicides known from the literature which can be combined according to the invention with the compounds of the formula I include the following products: aldimorph, andoprim, anilazines, BAS 480F, BAS 450F, BAS 490F, benalaxyl, benodanil, benomyl, binapacryl, bitertanol, bromuconazole, Buthiobate, captafol, captan, carbendazim, carboxin, CGA 173506, cyprodinil, cyprofuram, dichlofluanid, dichlomezin, diclobutrazole, diethofencarb, difenconazole (CGA 169374), difluconazole, dimethirimol, dimethomorph, dinapod, dodinodimole, dinododirol, dinododirol, dinododirol, dinododirol, dinododo
  • the above-mentioned combination partners are known active ingredients, which are largely 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 the commercially available formulations can vary within wide ranges, the active substance concentration of the use forms can be from 0.0001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • a dusting agent is obtained by mixing 10 parts by weight of active ingredient and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as the inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the wetting agent. and dispersant mixes and grinds in a pin mill.
  • a dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and in a attritor ground to a fineness of less than 5 microns.
  • An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.
  • Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or quartz sand.
  • a suspension of the wettable powder from example b) having a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately.
  • the proportion by weight of the wettable powder is approximately 5% and that of the inert carrier material approximately 95% of the finished granulate.
  • Cut stems with a leaf of bean plants are transferred to amber glass bottles filled with tap water and then covered with about 100 spider mites (Tetranychus urticae).
  • the plant leaf and spider mites are sprayed with an aqueous solution of the preparation to be tested and formulated until they begin to drip.
  • plants and animals are stored in a climatic chamber (16 hours light day, 25 ° C, 40-60% RH). After 6 days of storage, the effect of the preparation on all stages of the spider mite is determined.
  • the preparation according to Example No. 63 causes 90-100% mortality.
  • Germinated field bean seeds (Vicia faba) with germ roots are transferred to amber glass bottles filled with tap water and then coated with approx. 100 black bean aphids (Aphis fabae). Plants and aphids are sprayed with an aqueous solution of the preparation to be tested and formulated until they begin to drip. After draining, plants and animals are stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 3 and 6 days of storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparation according to Example No. 63 causes 90-100% mortality of the aphids.
  • Rice seeds are germinated on moist cotton wool in glass jars. After this, Rice seeds are germinated on moist cotton wool in glass jars. After this, Rice seeds are germinated on moist cotton wool in glass jars. After this, Rice seeds are germinated on moist cotton wool in glass jars. After this, Rice seeds are germinated on moist cotton wool in glass jars. After this, Rice seeds are germinated on moist cotton wool in glass jars. After this
  • the rice plants treated in this way are placed in breeding containers and populated with 10 larvae (L3 stage) of the leafhopper species Nilaparvata lugens.
  • plants and animals are stored in a climatic chamber (16 hours light day, 25 ° C, 40-60% RH).
  • a concentration of 300 ppm (based on the active ingredient content), the preparation according to Example No. 63 shows 90-100% mortality in the test animals used.
  • a Petri dish is prepared, half of which is covered with filter paper and contains a germinated grain of corn on a damp cotton swab. About 50, 4-5 day old eggs of the corn rootworm (Diabrotica undecimpunctata) are transferred to the filter paper. The petri dish with the eggs and the corn kernel is then sprayed with an aqueous solution of the preparation to be tested and formulated. After closing the Petri dish, it is stored in a climate chamber at approx. 25 ° C. After 6 days of storage, the mortality of the preparation on the eggs and any larvae hatched from them is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparation according to Example No. 63 causes 90-100% mortality.
  • Test part A Approx. 5000 freshly hatched, active (mobile) larvae (2nd stage of development) of the root bile nematode (Meloidogyne incognita) are added to a glass vessel with an aqueous solution of the preparation to be tested and formulated. After 2 days of permanent exposure of the nematode larvae, the percentage of individuals who became immobile due to the action of the preparation compared to the untreated controls is determined (percent nematicidal contact effect).
  • Test part B soil drench effect: For this purpose, the entire solution from test part A (active ingredient and pretreated nematode larvae) is poured into a pot filled with soil and planted with three 9-day-old cucumber plants (Cucumis sativus). This drench application reduces the active substance content based on the soil volume to a third of the active substance content from test part A. After two weeks in the greenhouse at approx. 26 ° C (watering twice a day), the root balls of the cucumber plants are carefully washed out of the soil mixture contaminated with nematodes. The number of root galls per plant is counted and compared with the infestation of untreated control plants. The percentage infestation reduction as a criterion for the impact assessment is calculated using the Abbott formula (percent nematicidal soil-drench effect).
  • the preparation according to Example No. 63 has a 90-100% activity against the root-bile nematode Meloidogyne incognita.
  • Cut stems with a leaf of bean plants are transferred to amber glass bottles filled with tap water and then covered with about 100 spider mites (Tetranychus urticae).
  • the plant leaf and spider mites are then immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated.
  • plants and animals are stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 6 days of storage, the mortality of the preparation is determined at all stages of the spider mite.
  • a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Example Nos.
  • Germinated field bean seeds (Vicia faba) with germ roots are transferred to amber glass bottles filled with tap water and then coated with approx. 100 black bean aphids (Aphis fabae). Plants and aphids are then immersed in an aqueous solution of the preparation to be tested and formulated for 5 seconds. After draining, plants and animals are stored in a climatic chamber (16 hours light day, 25 ° C, 40-60% RH). After 3 and 6 days of storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Example No.
  • the leaves of 12 rice plants with a stem length of 8 cm are immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated.
  • the rice plants treated in this way are placed in a Petri dish and populated with about 20 larvae (L3 stage) of the rice leafhopper species Nilaparvata lugens; after closing the Petri dish, it is stored in a climatic chamber ((16 hours light / day, 25 ° C, 40-60% RH) After 6 days of storage, the mortality of the cicada larvae is determined At a concentration of 300 ppm (based on the active ingredient content), the preparations according to Example No.
  • a petri dish the bottom of which is covered with filter paper and contains about 5 ml of nutrient medium, is prepared.
  • Pieces of filter paper with approximately 30, 24-hour-old eggs of the American tobacco bud owl (Heliothis virescens) are immersed in an aqueous solution of the preparation to be tested and formulated for 5 seconds and then placed in the petri dish.
  • a further 200 ⁇ l of the aqueous solution are distributed over the nutrient medium.
  • After closing the Petri dish it is stored in a climate chamber at approx. 25 ° C. After 6 days of storage, the effect of the preparation on the eggs and any larvae hatched from them is determined.
  • a petri dish the bottom of which is covered with filter paper and contains about 5 ml of nutrient medium, is prepared.
  • Ten L2 larvae of the Egyptian cottonworm (Spodoptera littoralis) are counted in a small cup.
  • 200 ⁇ l of an aqueous solution of the preparation to be tested and formulated is pipetted into the beaker.
  • the treated larvae are then poured into the petri dish and a further 200 ⁇ l of the aqueous solution are distributed over the nutrient medium.
  • After closing the Petri dish it is stored in a climate chamber at approx. 25 ° C. After 6 days of storage, the effect of the preparation on the larvae is determined.
  • Example 11 At a concentration of 300 ppm (based on the active ingredient content), the preparations according to Example Nos. 24, 68, 83, 216, 219, 221, 227, 231, 233, 236, 245, 246, 266, 268, 276 , 300, 366, 375, 379, 390, 623, 637, 641-644, 649-651 a 90-100% mortality of the larvae.
  • Example 11 At a concentration of 300 ppm (based on the active ingredient content), the preparations according to Example Nos. 24, 68, 83, 216, 219, 221, 227, 231, 233, 236, 245, 246, 266, 268, 276 , 300, 366, 375, 379, 390, 623, 637, 641-644, 649-651 a 90-100% mortality of the larvae.
  • Example 11 Example 11
  • a Petri dish is prepared, half of which is covered with filter paper and contains a germinated grain of corn on a damp cotton swab. About 50, 4-5 day old eggs of the corn rootworm (Diabrotica undecimpunctata) are transferred to the filter paper. Three drops of 200 ⁇ l of an aqueous solution of the preparation to be tested and formulated are pipetted onto the eggs and the rest onto the corn kernel. After closing the Petri dish, it is stored in a climate chamber at approx. 25 ° C. After 6 days of storage, the mortality of the preparation on the eggs and any larvae hatched from them is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Example No.
  • Test part A An aqueous solution of the preparation to be tested and formulated (final volume 20 ml) is added to approx. 3000 freshly hatched, active (mobile) larvae (2nd stage of development) of the root bile nematode (Meloidogyne incognita) in a glass vessel. After 6 days of permanent exposure of the nematode larvae, the percentage of individuals who became immobile due to the action of the preparation compared to the untreated controls is determined (percent nematicidal contact effect).
  • Test part B soil-drench effect: For this purpose, the entire solution from test part A (active ingredient and pretreated nematode larvae) is poured into a pot filled with 60 ml of soil and planted with three 9-day-old cucumber plants (Cucumis sativus). This drench application reduces the active substance content based on the soil volume to one third of the active substance content from test part A. After two weeks in the greenhouse at approx. 26 ° C (twice daily watering), the root balls of the cucumber plants are carefully washed out of the soil mixture contaminated with nematodes. The number of root galls per plant is counted and compared with the infestation of untreated control plants. The percentage infestation reduction as a criterion for the impact assessment is calculated using the Abbott formula (percent nematicidal soil-drench effect).
  • the preparations according to Example No. 24, 81-83, 116, 169, 216-219, 221, 231, 233, 246, 268, 276, 280, 301, 303, 304, 366, 375, 379, 390, 642-644, 646-653, 657 have a 90-100% activity against the root bile nematode Meloidogyne incognita.
  • the compounds were tested for activity against one or more of the following organisms:
  • Aqueous solutions or dispersions of the compounds in the desired concentration with the addition of a wetting agent were applied to leaves or stems of the test plant.
  • the plants or parts of plants were inoculated with the respective test pathogen and kept under controlled environmental conditions suitable for plant growth and the development of the disease are. After a suitable time, the degree of infection of the infected plant was assessed visually.
  • the compounds are assessed on a scale from 1 to 3, in which 1 means a low control, 2 medium control and 3 good to complete control. At a concentration of 500 ppm (w / v) or less, the following compounds were rated 2 or higher against the fungi listed.
  • Plasmopara viticola 24, 63, 73, 86, 98, 141, 213, 220, 221, 246, 366, 643,
  • Erysiphe graminis 65, 68, 71-74, 208, 213, 216, 217, 219-221, 233, 246,
  • Leptosphaeria nodorum 24, 73, 83, 85, 86, 98, 214, 218-221, 246, 233, 259, 301,
  • Phytophtora infestans 24, 83, 86, 116, 141, 218, 219, 221, 233, 276, 301, 366,

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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)
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  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des hétérocycles d'azote substitués, des procédés permettant de les préparer et leur utilisation comme agents de lutte contre les parasites. Dans la formule (I), A désigne CH et D désigne N+R, A désigne azote et D désigne N+R ou A désigne N+R et D désigne azote, R désigne -CR?4R5-E-R6, Qn-¿ désigne un anion inorganique ou organique, n vaut 1, 2, 3 ou 4 et R1-R6 désignent E, X, Y et Z, tels qu'ils sont définis dans la description. L'invention concerne en outre des procédés permettant de les préparer et leur utilisation comme agents de lutte contre les parasites.
EP98921486A 1997-05-09 1998-04-24 Heterocycles d'azote substitues, procedes permettant de les preparer et leur utilisation comme agents de lutte contre les parasites Withdrawn EP0981518A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19719590 1997-05-09
DE19719590A DE19719590A1 (de) 1997-05-09 1997-05-09 Substituierte Stickstoff-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
PCT/EP1998/002432 WO1998051674A1 (fr) 1997-05-09 1998-04-24 Heterocycles d'azote substitues, procedes permettant de les preparer et leur utilisation comme agents de lutte contre les parasites

Publications (1)

Publication Number Publication Date
EP0981518A1 true EP0981518A1 (fr) 2000-03-01

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EP (1) EP0981518A1 (fr)
JP (1) JP2001526659A (fr)
AU (1) AU7431898A (fr)
DE (1) DE19719590A1 (fr)
WO (1) WO1998051674A1 (fr)
ZA (1) ZA983840B (fr)

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Publication number Priority date Publication date Assignee Title
GB9810860D0 (en) * 1998-05-20 1998-07-22 Hoechst Schering Agrevo Gmbh Substituted pyridine and pyrimidines, processes for their preparation and their use as pesticides
GB9816729D0 (en) * 1998-08-01 1998-09-30 Hoechst Schering Agrevo Gmbh Substituted cyclohexylaminopyrimidines

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BE588862A (fr) * 1959-03-23
NL282004A (fr) * 1961-08-25
US3260723A (en) * 1963-08-27 1966-07-12 Parke Davis & Co 4-phenoxy piperidines; alpha4-phenoxy piperideines
JPS54915B2 (fr) * 1971-11-19 1979-01-18
DE4208254A1 (de) * 1992-03-14 1993-09-16 Hoechst Ag Substituierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel und fungizid
DE4331180A1 (de) * 1993-09-14 1995-03-16 Hoechst Schering Agrevo Gmbh Substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide
DE4331181A1 (de) * 1993-09-14 1995-03-16 Hoechst Schering Agrevo Gmbh Substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide
DE4437137A1 (de) * 1994-10-18 1996-04-25 Hoechst Schering Agrevo Gmbh Substituierte Cycloalkylamino- und -alkoxy-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel

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Title
See references of WO9851674A1 *

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DE19719590A1 (de) 1998-11-12
AU7431898A (en) 1998-12-08
ZA983840B (en) 1998-11-09
WO1998051674A1 (fr) 1998-11-19

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