EP1068197A1 - Piperidines substituees, leur procede de preparation et leur utilisation comme parasiticides et fongicides - Google Patents

Piperidines substituees, leur procede de preparation et leur utilisation comme parasiticides et fongicides

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Publication number
EP1068197A1
EP1068197A1 EP99916871A EP99916871A EP1068197A1 EP 1068197 A1 EP1068197 A1 EP 1068197A1 EP 99916871 A EP99916871 A EP 99916871A EP 99916871 A EP99916871 A EP 99916871A EP 1068197 A1 EP1068197 A1 EP 1068197A1
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EP
European Patent Office
Prior art keywords
alkyl
group
radicals
fluorine
halogen
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Withdrawn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
EP99916871A
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German (de)
English (en)
Inventor
Wolfgang Schaper
Ralf Braun
Harald Jakobi
Gerhard Krautstrunk
Martin Märkl
Oswald Ort
Manfred Kern
Ulrich Sanft
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
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Aventis CropScience GmbH
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Filing date
Publication date
Application filed by Aventis CropScience GmbH filed Critical Aventis CropScience GmbH
Publication of EP1068197A1 publication Critical patent/EP1068197A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07D401/12—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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D405/14—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
    • 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
    • C07D409/14—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

Definitions

  • the invention relates to substituted piperidines, processes for their preparation and their use as pesticides and fungicides.
  • residues and groups are defined as below, which, with good plant tolerance and favorable warm-blood toxicity, are very good for combating animal pests, such as insects, arachnids, nematodes, helminths and molluscs, for combating endo- and ectoparasites in the veterinary field and for combat harmful fungi.
  • the invention therefore relates to compounds of the formula (I) in which R 1 is hydrogen, halogen, (C r C 8 ) alkyl, (C r C 8 ) haloalkyl, (C ⁇ C ⁇ J-alkoxy or (C 3 -C 6 ) cycloalkyl;
  • R 2 and R 3 are identical or different and are each hydrogen, (C r C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C ⁇ C ⁇ alkoxy, Halogen, Hydroxy, Cyano, Nitro, Thiocyano, (C r C 8 ) -alkanoyl, (C r C 8 ) -alkoxycarbonyl, (C.-C ⁇ J-Akylthio, (C r C 8 ) -alkylsulfinyl, (C 1 -C 8 ) -Alkylsulfonyl, amino, (C CgJ-alkylamino, (C r C 8 ) -dialkylamino or (C 3 -C 6 ) -cycloalkyl mean, wherein in the alkyl, cycloalkyl, alkenyl, alkynyl radicals or the groups derived there
  • 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 may contain or which, if it is a 6-ring, may 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 (CC 4 ) -alkyl, (C 1 -C 4 -haloalkyl, preferably trifluoromethyl, halogen, (C 1 -C 4 -alkoxy or (C 1 -C 4 ) -haloalkoxy); or
  • R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered isocyclic ring which may contain oxygen and / or sulfur instead of one or two CH 2 groups and which is optionally substituted by 1, 2 or 3 (C r C 4 ) alkyl groups;
  • A represents CH or N; 3
  • Y and Z are identical or different and each represent oxygen, sulfur or a group NR 5 ' or NR 5 " , where R 5' and R 5" are identical or different and each has the meanings given below for R 5 ; or in the event that Y is sulfur or a group NR 5, Z can also be a direct bond, or in the event that Y is a group NR 5 ' , R 5' also additionally nitro, cyano, hydroxy, alkoxy or a group NR 5 " R 5"' , where R 5 * " and R 5'” are the same or different and each may have the meanings given below for R 5 , m and n are the same or different and the numbers 1 , 2, 3, 4 or 5 mean and the sum of m and n does not exceed the number 6;
  • R 4 and R 4 ' are the same or different and each represents hydrogen, (CC 4 ) alkyl, (C 1 -C 4 ) haloalkyl, halogen or (CC 4 ) alkoxy;
  • R 5 denotes alkyl, alkenyl, alkynyl, aryl, heterocyclyl, where the listed
  • R 1 is hydrogen, halogen, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl or (C 3 -C 5 ) cycloalkyl;
  • R 2 and R 3 are the same or different and each is hydrogen; (C ⁇ C ⁇ alkyl, (d-CJ-haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4) haloalkynyl, Trimethylsilylalkinyl, (C r C4) alkoxy, (C r C4) - haloalkoxy, (C r C4) alkoxy- (C r C alkyl 4), (CC ⁇ haloalkoxy CCRC - alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) haloalkyl, (C r C 4 ) -haloalkoxy- (C r C 4 ) - 5 haloalkyl, halogen, hydroxy, (CC 4 ) hydroxyalky
  • 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, (CC 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 may contain oxygen and / or sulfur instead of one or two CH 2 groups and which is optionally substituted by 1, 2 or 3 (CC 4 ) alkyl groups, and
  • R 1 represents hydrogen, fluorine, chlorine or methyl
  • R 2 (C r C 4 ) -alkyl, (C.-C ⁇ alkenyl, (C ⁇ C ⁇ -alkynyl, (C r C 4 ) -haloalkyl,
  • R 3 is hydrogen, halogen, methyl, ethyl, ethynyl, vinyl, halovinyl, (C r C 2 ) -
  • R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 5- or 6-membered ring which instead of a CH 2 -
  • Unit may contain a sulfur or an oxygen atom;
  • A represents CH or N;
  • X represents NH or oxygen;
  • Y and Z are the same or different and are each oxygen, sulfur or one
  • Group NR 5 ' or NR 5 " ; R 4 and R 4' are identical or different and each represents hydrogen or methyl; m and n each represent the number 2;
  • R 1 represents hydrogen
  • R 2 is methyl, ethyl, propyl, isopropyl, (C r C 2 ) fluoroalkyl, cyclopropyl or
  • R 3 is halogen, methyl, ethyl, ethynyl, vinyl, fluorovinyl, methoxy, ethoxy or
  • R 2 and R 3 together with the ring system to which they are attached form the quinazoline or quinoline system, which may be substituted by fluorine in the carbocyclic part; or R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 6-membered ring which may contain an oxygen or sulfur atom instead of a CH 2 group; R 4 and R 4 ' means hydrogen.
  • R 1 represents hydrogen
  • R 2 represents methyl, ethyl, propyl, isopropyl, 1-fluoroethyl or methoxymethyl
  • R 3 represents fluorine, chlorine, bromine, cyano, vinyl, ethynyl or methoxy; or for 8 when A is nitrogen, R 2 and R 3 together with the ring system to which they are attached form the quinazoline system, which may be substituted with a fluorine atom;
  • X represents NH;
  • Y and Z represent oxygen or sulfur; R 4 and R 4 'represents hydrogen; m and n means the number 2.
  • R 1 represents hydrogen
  • R 2 represents ethyl or methoxymethyl
  • R 3 is fluorine, chlorine, bromine, ethynyl or methoxy, preferably fluorine, chlorine, bromine or methoxy;
  • AN means;
  • X represents NH;
  • Y and Z are oxygen or sulfur, preferably oxygen; R 4 and R 4 'are hydrogen; m and n represent the number 2;
  • R 5 denotes (CVC-ac ⁇ -alkyl, (C 2 -C 20 ) alkenyl, (C 2 -C 20 ) alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals listed are unsubstituted or with up to three, in the case of fluorine, the same or different radicals can also be provided up to the maximum number and one or more, preferably up to three, non-adjacent saturated carbon units by heteroatom units, such as oxygen, in the alkyl, alkenyl or alkynyl radicals mentioned or SiR 7 R 8 , where R 7 and R 8 are (C 1 -C 4 ) -alkyl, preferably methyl, and in addition 3 to 6 atoms of these hydrocarbon radicals, optionally modified as above, form a cycle can and these hydrocarbon residues with or without the specified 9
  • Variations optionally with one or more, preferably up to three, in the case of halogen up to the maximum number of identical or different radicals from the halogen series, preferably fluorine, aryl, aryioxy, arylthio, (C 3 -C 8 ) -cycloalkoxy, ( C 3 -C 8 ) -cycloalkylthio, heterocyclyl, heterocyclyloxy or (C 1 -C 2 ) -alkoxycarbonyl may be substituted, where the cycloaliphatic, aromatic or heterocyclic ring systems are unsubstituted or with up to three, in the case of the substituents just mentioned fluorine can also be provided with up to the maximum number of identical or different substituents;
  • R 5 (C 1 -C 15 ) alkyl, aryl or heterocyclyl in the sense of heteroaromatic
  • Ring system means that the aryl or heterocyclyl radical 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 radicals and in the alkyl radical mentioned one or more, preferably up to three, not adjacent saturated carbon units can be replaced by oxygen, and in addition 3 to 8 atoms of this optionally modified alkyl radical as above 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, or can be substituted with an aryl radical and this aryl radical 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.
  • halogen means a fluorine, chlorine, bromine or iodine atom
  • Hydrocarbon residue with 1 to 4 carbon atoms e.g. the methyl, ethyl,
  • Pentyl 2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl, octyl, or the
  • cycloalkyl preferably (C 3 -C 8 ) cycloalkyl
  • cycloalkoxy preferably (C 3 -C 8 ) cycloalkoxy
  • cycloalkylthio preferably (C 3 -C 8 ) cycloalkylthio
  • (C 3 -C 3 ) cycloalkyl the cyclopropyl, cyclobutyl or
  • Cyclopentyl group under the expression "(C 3 -C 6 ) cycloalkyl” the radicals mentioned above under “(C 3 -C 5 ) cycloalkyl” and the cyclohexyl radical; under the expression “(C 3 -C 8 ) cycloalkyl” the radicals mentioned above under “(C 3 -C 6 ) cycloalkyl” and the cycloheptyl or cyclooctyl radical; under the expression “(C 3 -C 5 ) halocycloalkyl" one of those listed above
  • Chlorine are replaced, such as the 2,2-difluoro or 2,2-dichlorocyclopropane
  • Halogen preferably fluorine or chlorine, are replaced; under the expression "(C 2 -C 4 ) alkynyl", for example the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group; under the expression “(C 2 -C 8 ) alkynyl”, for example, the abovementioned radicals and, for example, the 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl or the 1-octynyl group, under which Expression "(C 2 -C 20 ) alkynyl" the radicals mentioned above, and for example the 1-decynyl or the 2-decynyl group; under the expression "(C 2 -C 4 ) haloalkynyl" a (C 2 -C 4 ) alkynyl group in which the
  • Halogen atoms preferably fluorine or chlorine, are replaced; under the expression "(C r C 4 ) -hydroxyalkyl", for example the hydroxymethyl,
  • Valeroyl, pivaloyl, hexanoyl, heptanoyl or octanoyl group under the expression "(CC ⁇ -alkanoyl", for example, the abovementioned radicals and, for example, the nonanoyl, decanoyl or the dodecanoyl group; under the expression "(C 2 -C 4 ) haloalkanoyl” a (C 1 -C 4 ) -Alkanoyl group, in which the hydrogen atoms partially, in the case of fluorine also completely, by 12
  • Halogen atoms preferably fluorine or chlorine, are replaced; under the expression "(C 2 -C 12 ) -haloalkanoyl" a (CC ⁇ -alkanoyl group) in which the hydrogen atoms partially, in the case of fluorine also completely, by
  • Halogen atoms preferably fluorine or chlorine, are replaced; under the expression "cyano (C r C 4 ) alkyl" a cyanoalkyl group, the
  • 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 "(C ⁇ C -alkylthio") an alkylthio group, the
  • Alkylsulfinyl groups e.g. the pentylsulfinyl, 2-methylbutylsulfinyl,
  • Hexylsulfinyl or octylsulfinyl group under the expression "(C r C 4 ) alkylsulfonyl", for example the methyl, ethyl, propyl,
  • Haloalkylsulfonyl "(C 1 -C 4 -alkylsulfinyl- and -sulfonyl radicals with the meanings given above, in which one or more, in the case of fluorine, if appropriate also all, hydrogen atoms of the hydrocarbon part through
  • Halogen especially chlorine or fluorine, are replaced; under the terms “fluoromethylsulfinyl” and “fluoromethylsulfonyl” the mono-, di- and trifluoromethyl-sulfinyl and -sulfonyl group; under the expression "(C ⁇ C -alkoxy”) an alkoxy group, the
  • Alkylsulfonyl groups e.g. the pentyl, 2-methylbutyl, hexyl, heptyl or
  • Octylsulfonyl group under the expression "(C C ⁇ alkylamino" for example the methylamino, ethylamino,
  • Alkylamino groups and for example the pentylamino, hexylamino, heptylamino or 14
  • Octylamino group under the expression "(C 1 -C 4 ) dialkylamino", for example the dimethylamino, methylethylamino, diethylamino, dipropylamino or the dibutylamino group, but also cyclic systems, such as the pyrrolidino or piperidino group Group, under the expression "(C r C 8 ) dialkylamino" one of the above (C r C 4 ) -
  • Dialkylamino groups e.g. the dipentyl, dihexyl or dioctylamino
  • Halogen hydrocarbon radical has the meaning given under the expression “(CC 4 ) -haloalkyl”; 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 - ⁇ - OJ-alkyl radicals with the meanings given above, in which one or more, in the case of fluorine, if appropriate also all, hydrogen atoms of the corresponding hydrocarbon portions are replaced by halogen, preferably chlorine or fluorine; under the expression "(C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl" for example
  • aryl is an isocyclic aromatic radical having preferably 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or
  • Biphenylyl preferably phenyl; under the expression “heterocyclyl” preferably a heteroaromatic or heteroaliphatic ring system, under “heteroaromatic ring system” preferably an aryl radical in which at least one CH group is replaced by N and / or at least two adjacent CH groups are replaced by S, NH or O. is to be understood, for example a residue of thiophene, furan, pyrrole, thiazole, oxazole, 15
  • Imidazole isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole,
  • Benzisothiazole benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran,
  • aryl 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
  • heterocyclyloxy or "heterocyclylthio” one of the abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom
  • heterocyclyloxy or "heterocyclylthio” one of the abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom
  • (C 3 -C 8 ) -cycloalkoxy or "(C 3 -C 8 ) -cycloalkylthio" one of the above-mentioned (C 3 -C 8 ) -cycloalkyl radicals, which via an oxygen or
  • Phenylbutyryl or the naphthylacetyl group under the expression "(C 3 -C 8 ) cycloalkyl (C r C 4 ) alkanoyr for example the
  • Nicotinoyl, thienylacetyl or the pyridine propionyl group under the expression "(C 3 -C 8 ) cycloalkoxycarbonyl", for example the cyclobutyloxycarbonyl,
  • heterocyclyl ⁇ C ⁇ C alkoxycarbonyl e.g. the thienylmethoxycarbonyl
  • Naphthoxycarbonyl or the biphenyloxycarbonyl group under the expression "hetercyclyloxycarbonyl", for example the tetrahydropyran-4-oxycarbonyl group; under the expression "(C 1 -C 20 ) alkanoyloxy M, for example formyloxy, acetoxy,
  • Hydrogen atoms of the hydrocarbon part are replaced by halogen, in particular fluorine or chlorine; under the expression "(C 3 -C 8 ) cycloalkanoyloxy", for example the cyclopropanoyloxy,
  • the thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or the pyrimidinylcarbonyloxy group for example, the methane, ethane, butane or hexanesulfonyloxy group under the expression "(C ⁇ CjoJ-alkylsulfonyloxy”; under the term “arylsulfonyloxy” for example the phenylsulfonyloxy or the toluenesulfonyloxy group; under the term “halovinyl” a vinyl group, in of which the hydrogen atoms are partially or completely replaced by halogen, preferably fluorine or chlorine, under the term “fluorovinyl” a vinyl group in which the hydrogen atoms are partly or completely replaced by fluorine.
  • the substituents with which the various aliphatic, cycloaliphatic aromatic and heterocyclic ring systems can be provided include, for example, halogen, nitro, cyano, di ⁇ C ⁇ C ⁇ alkylamino, (CC 4 ) alkyl, (C 3 -C 8 ) - Cycloalkyl, (C r C 4 ) -trialkylsilyl, (C r C 4 ) -alkoxy, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 2 ) -alkoxy- [CH 2 CH 2 O] 0 ⁇ 1 ⁇ 2 -ethoxy, (dC ⁇ -alkylthio, (CC -alkylsulfinyl, (C r C 4 ) - alkylsulfonyl, phenyl, benzyl, phenoxy, halophenoxy, (CC 4
  • Alkoxyalkyl radicals such as, for example, the methoxymethyl, methoxyethyl or ethoxyethyl group; or 19
  • Alkoxy-alkoxy-alkyl radicals such as e.g. the methoxy or the ethoxy ethoxyethyl
  • Alkylthioalkyl residues e.g. the methyl or the ethylthioethyl group;
  • Alkylsulfinyl-alkyl residues e.g. the methyl or ethylsulfinylethyl group
  • 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, such as e.g. the
  • Arylalkyldialkylsilyl preferably arylalkyldimethylsilyl, e.g. the
  • Alkanoylalkyl radicals such as e.g. the acetylmethyl or the pivaloylmethyl group; or cycloalkanoylalkyl radicals, such as e.g. the cyclopropylcarbonylmethyl or the
  • Haloalkanoylalkyl radicals such as e.g. the trifluoro or trichloroacetylmethyl group; or
  • Aroylalkyl residues e.g. the benzoyl or naphthoylalkyl residues, e.g. the
  • Heterocyclylcarbonylalkyl residues 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, e.g. the cyclopropyl, cyclobutyl, cyclopentyl,
  • Alkyl-cycloalkyl radicals such as e.g. the 4-methyl or the 4-tert-butylcyclohexyl
  • Cycloalkyl-alkyl radicals such as e.g. the cyclohexylmethyl or ethyl group
  • Cycloalkylene residues monocyclic, e.g. the cyclopentenyl, cyclohexenyl,
  • Cycloheptenyl or cyclooctenyl radical bicyclic, e.g. the norbomenyl or the bicyclo [2,2,2] octenyl radical, or condensed, such as the various dihydro or tetrahydronaphthyl radicals;
  • Cycloalkylene-alkyl radicals such as e.g. the 1-cyclohexenyl-methyl or -ethyl radical; or also haloalkyl derivatives of the corresponding groups, such as, for example
  • Haloalkyl haloalkoxyalkyl, alkoxy haloalkyl, haloalkyl cycloalkyl or
  • the present invention relates to the compounds of formula (I) in the form of the free base or an acid addition salt.
  • Acids that can be used for salt formation are inorganic acids, such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, or organic acids, such as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid. 21
  • Some of 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 a chiral enantiomerically pure acid, separation of the diastereomeric salts and release of the pure enantiomers by means of 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
  • A, R 2 and R 3 have the meanings given under formula I and L denotes a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, with a nucleophile of the formula (III),
  • the leaving group L can be varied within wide limits and can mean, for example, a halogen atom, such as fluorine, chlorine, bromine or iodine, or alkylthio, such as methyl or ethylthio, or alkanesulfonyloxy, such as methane, trifluoromethane or ethanesulfonyloxy, or arylsulfonyloxy, such as benzenesulfonyloxy or toluenesulfonyloxy , or alkylsulfonyl, such as methyl- or ethylsulfonyl, or arylsulfonyl, such as phenyl- or toluenesulfonyl.
  • a halogen atom such as fluorine, chlorine, bromine or iodine
  • alkylthio such as methyl or ethylthio
  • the aforementioned reaction is carried out in a temperature range from 20 to 150 ° C., advantageously in the presence of a base and optionally in an inert organic solvent, such as 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 N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, Dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol,
  • Suitable bases for the case where X is oxygen are, for example, alkali or alkaline earth metal carbonates, bicarbonates, amides or hydrides, such as sodium carbonate, sodium bicarbonate, potassium carbonate, sodium amide or sodium hydride; if X is NH, these are, for example Alkali or alkaline earth metal carbonates, hydrogen carbonates, hydroxides, amides or hydrides, such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium hydroxide, sodium amide or sodium hydride, or organic bases, such as triethylamine or pyridine.
  • a second equivalent of an amine of formula (III) can also be used as an auxiliary base. 23
  • 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
  • A, R 1 , R 2 and R 3 have the meanings given under formula (I) and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or 24
  • Arylsulfonyloxy, alkylsulfonyl or arylsulfonyl means with a nucleophile of the formula (V)
  • Y, Z and R 5 has the meanings given for formula (I) and L 'is a leaving group, preferably fluorine, chlorine or bromine, and in the compounds of the formula (I) obtained in this way or in another way optionally the pyridine or Pyrimidine system or the piperidine side chain further derivatized.
  • Suitable protective groups Sg for formula VI are, for example, the trifluoroacetyl, tert-butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxybenzyl, dimethoxybenzyl, trityi or the 9-phenylfluorenyl group, each under basic, acidic, hydrogenolytic or oxidative Conditions can be split off (see e.g. PJ Kocienski, Protecting Groups, Georg Thieme Verlag, Stuttgart 1994).
  • reaction of the compounds of formula (II) with the compounds of formula (V) to give the compounds of formula (VI) is carried out completely analogously to the reaction of the compounds of formula (II) with the compounds of formula (III).
  • the protective group Sg is split off from the compounds of the formula (VI), for example among the methods given in the literature for the individual protective groups (see e.g. P.J. Kocienski, Protecting Groups, Georg Thieme Verlag, Stuttgart 1994).
  • a tert-butoxycarbonyl protective group is split off, e.g. by treating the compound of formula (VI) with acid in an inert solvent such as dichloromethane or toluene.
  • reaction of the compounds of formula (VII) with the compounds of formula VIII to the end products of formula (I) is conveniently carried out in the presence 26 a base such as triethylamine or pyridine or inorganic acid binders such as alkali or alkaline earth carbonates, or hydrogen carbonates such as sodium, potassium or calcium carbonate or sodium or potassium hydrogen carbonate, in an inert solvent such as dichloromethane , Trichloromethane, tetrahydrofuran, benzene, toluene or pyridine.
  • a base such as triethylamine or pyridine or inorganic acid binders such as alkali or alkaline earth carbonates, or hydrogen carbonates such as sodium, potassium or calcium carbonate or sodium or potassium hydrogen carbonate
  • an inert solvent such as dichloromethane , Trichloromethane, tetrahydrofuran, benzene, toluene or pyridine.
  • Collections of compounds of the formula (I) which can be synthesized according to the above-mentioned scheme can also be produced in a parallelized manner, this being possible in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction, the work-up or the cleaning of the products or intermediate stages. Overall, this is understood to mean a procedure such as that used by S.H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated synthesis", Volume 1, Publisher Escom 1997, pages 69 to 77.
  • Automation systems of this type can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.
  • compounds of the general formula (I) can be prepared completely or partially by methods supported by solid phases.
  • solid phase supported synthesis methods are adequately described in the specialist literature, e.g. Barry A. Bunin in "The Combinatorial Index", published by Academic Press, 1998.
  • the use of synthesis methods supported by solid phases allows a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the "teabag method” Houghten, US 4,631,211; Houghten et al., Proc. Natl. Acad.
  • the preparation according to the processes described here provides compounds of the formula (I) in the form of substance collections which are called libraries.
  • the present invention also relates to libraries which contain at least two compounds of the formula (I). 28
  • the active compounds of the formula (I) are suitable for combating animal pests, in particular insects, arachnids, helminths and molluscs, very particularly preferably for combating insects and arachnids which, in the case of good plant tolerance and favorable warm-blood toxicity
  • Acarina e.g. Acarus siro, Argas spp., Omithodoros 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.
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empouscuspspp.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp ..
  • 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 that can be controlled according to the invention include, for example, the root-parasitic soil nematodes, e.g. those of the genera Meloidogyne (root-knot nematodes such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii) and of the genera Radopholus, such as Radopholus similis, Pratylenchus such as Pratyglenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus;
  • the root-parasitic soil nematodes e.g. those of the genera Meloidogyne (root-knot nematodes such as Meloidog
  • Tylenchulus such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus such as Rotylenchus robustus, Heliocotylenchus such as Haliocotylenchus multicinctus, Belonoaimus such as Belonoaimus Trachusususus longusus x longus.
  • the compounds according to the invention can be used for the nematode genera Ditylenchus (stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes such as Aphelenchoides) 31 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 31 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 formula (I).
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • SC oil or water-based dispersions
  • SE suspoemulsions
  • SE suspoemulsions
  • DP dusts
  • mordants granules in the form of , Spray, elevator and adsorption granules
  • WG water-dispersible granules
  • ULV formulations microcapsules, waxes or baits.
  • the necessary formulation auxiliaries 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 wetting agents, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates, and dispersants, e.g. sodium lignosulfonic acid, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium.
  • wetting agents e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates
  • dispersants e.g. sodium lignosulfonic acid, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium.
  • Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or 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, sorboxyethyl ester fatty acid sorbityl ester fatty acids, polyethylenesorbites or fatty acid sorboxy fatty acid sorbityl ester fatty acids or polyesters
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite, pyrophillite, 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, for example polyvinyl alcohol. 33 polyacrylic acid sodium 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 substance concentration in wettable powders is e.g. 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.
  • 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 application rate required varies with the external conditions such as temperature, humidity and others. It can vary within wide limits, for example between 0.0005 and 10.0 kg / ha or more of active substance, but is preferably between 0.001 and 5 kg / ha. 34
  • the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations, alone or in mixtures with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the pesticides with which compounds of the formula (I) can be combined include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms, etc.
  • Alanycarb (OK-135), Aldicarb, 2-se ⁇ -Butylphenylmethylcarbamate (BPMC), Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Benfuracarb, Ethiofencarb, Furathiocarb, HCN-801, Isoprocarb, Methomyl, 5-Methyl-m-cumenylbutyryl carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio (ethylideneamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717), triazamate;
  • 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.
  • 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 use in the veterinary field, preferably for controlling endo- and ectoparasites and in the field of animal husbandry.
  • the active compounds according to the invention are preferably 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 and spot-on) and the pump, and by parenteral use in the form of, for example, injection.
  • the compounds of the formula (I) according to the invention can accordingly also be used particularly advantageously in animal husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese).
  • animal husbandry for example cattle, sheep, pigs and poultry such as chickens, geese.
  • the compounds of the formula (I) are administered to the animals orally, if appropriate in suitable formulations (cf. above) and optionally with the drinking water or feed. Since excretion in the feces occurs effectively, the development of 38
  • 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 compounds can e.g. in doses of 0.01 to 1 mg / kg body weight.
  • the compounds of formula (I) according to the invention are also distinguished by 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 action of the claimed compounds covers various economically important phytopathogenic fungi, such as e.g. 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 in the literature which can be combined according to the invention with the compounds of the formula (I): aldimorph, andoprim, anilazines, BAS 480F, BAS 450F, benalaxyl, benodanil, benomyl, binapacryl, bitertanol, bromuconazole, buthiobate , Captafol, Captan, Carbendazim, Carboxin, CGA 173506, Cyprofuram, Dichlofluanid, Dichlomezin, 39
  • the above-mentioned combination partners are known active ingredients, which are largely described in CDS Tomlin, SB Walker, The Pesticide Manual, 11th edition (1997), 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 40 are between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the compounds of the formula (I) can also be used to control harmful organisms in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain crop protection agents, resistance to plant diseases or pathogens causing plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, storability, composition and special ingredients.
  • Transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the invention therefore also relates to the use of compounds of the formula (I) for controlling harmful organisms in transgenic crop plants.
  • 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 readily 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.
  • the compounds were tested for activity against one or more of the following
  • 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 which are suitable for plant growth and the development of the disease. After a suitable time, the degree of infection of the infected plant was assessed visually.
  • the compounds are classified on a scale from 1 to 3, in which 1 no to low control, 2 medium control and 3 good to 52 means complete control, assessed. At a concentration of 500 ppm or less, the following compounds were rated 2 or higher against the listed fungi.
  • Cut stems with a leaf of bean plants were transferred to amber glass bottles filled with tap water and then covered with about 100 spider mites (Tetranychus urticae).
  • the plant leaf and spider mite were then immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated.
  • the plants and animals were 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 was determined.
  • the preparations according to Example Nos. 2, 6, 7, 8, 10, 17, 23, 27, 46, 52, 53, 49, 62, 65, 68 , 69, 70, 75 and 77 have a 90-100% mortality.
  • Germinated field bean seeds Vicia faba
  • Plants and aphids were then immersed in an aqueous solution of the preparation to be tested and formulated for 5 seconds. After draining, the plants and animals were 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 was determined. At a concentration of 300 ppm (based on the active substance content), the preparations according to Example Nos. 6, 7, 8, 10, 17, 23, 49, 53, 62, 64, 65, 68, 70, 75 and 76 90-100% aphid mortality. 54
  • the leaves of 12 rice plants with a stem length of 8 cm were immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated. After draining, the rice plants treated in this way were placed in a petri dish and populated with about 20 larvae (L3 stage) of the leafhopper species Nilaparvata lugens. After closing the petri dish, it was stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 6 days of storage, the mortality of the leafhopper larvae was determined. At a concentration of 300 ppm (based on the active ingredient content), the preparations according to Example Nos. 6, 7, 8, 49, 52, 53, 62, 64, 65, 68, 70, 75, 96 caused a 90-100 % mortality.
  • a petri dish the bottom of which was covered with filter paper and contained about 5 ml of nutrient medium, was prepared.
  • Pieces of filter paper with eggs of the American tobacco bud owl (Heliothis virescens) about 30, 24 hours old were immersed in an aqueous solution of the preparation to be tested and formulated for 5 seconds and then placed in the petri dish.
  • Another 200 ⁇ l of the aqueous solution were distributed over the nutrient medium.
  • After closing the petri dish it was 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 was determined.
  • the preparations according to Example Nos. 2, 6, 7, 8, 10, 17, 23, 49, 52, 53, 62, 64, 65, 68, 69 , 70, 75, 76 and 100 have a 90-100% mortality.
  • Petri dish filled with nutrient medium.
  • the nutrient medium and eggs were then sprayed with an aqueous solution of the preparation to be tested and formulated.
  • the petri dish was then closed with a lid. After 8 days
  • the active compounds were dissolved 10% (GA /) in a mixture consisting of dimethylformamide (85 g), nonylphenol polyglycol ether (3 g) and oxyethylated castor oil (7 g), and the emulsion concentrates thus obtained were diluted with water to a test concentration diluted by 1000 ppm.
  • the ticks were then dried on filter paper and then attached to the back of an adhesive film for the purpose of laying eggs.
  • the ticks were stored in a warming cabinet at 28 ° C and a humidity of 90%.

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
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  • Hydrogenated Pyridines (AREA)

Abstract

L'invention concerne des pipéridines substituées de formule (I), dans laquelle R<1> représente H, halogène, alkyle, halogénure d'alkyle ou cycloalkyle; R<2> et R<3> ont la signification donnée dans la description; A représente CH ou N; X représente NH, O ou S(O)q, q valant 0, 1 ou 2; Y et Z représentent O, S ou imino éventuellement substitué; m et n valent 1, 2, 3, 4 ou 5; R<4> et R<4'> représentent H, alkyle, halogénure d'alkyle, halogène ou alcoxy; R<5> représente l'un des radicaux suivants éventuellement substitués: alkyle, alcényle, alcynyle, aryle ou hétérocyclyle, un ou plusieurs motifs C pouvant être remplacés par CO ou par des motifs hétéroatome. L'invention concerne également un procédé pour préparer lesdits composés, des agents les contenant et leur utilisation comme parasiticides et fongicides.
EP99916871A 1998-04-03 1999-03-23 Piperidines substituees, leur procede de preparation et leur utilisation comme parasiticides et fongicides Withdrawn EP1068197A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19815026A DE19815026A1 (de) 1998-04-03 1998-04-03 Substituierte Piperidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide
DE19815026 1998-04-03
PCT/EP1999/001944 WO1999051589A1 (fr) 1998-04-03 1999-03-23 Piperidines substituees, leur procede de preparation et leur utilisation comme parasiticides et fongicides

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WO1999051589A1 (fr) 1999-10-14
US6300333B1 (en) 2001-10-09
ZA200005182B (en) 2001-09-26
DE19815026A1 (de) 1999-10-07
AU761602B2 (en) 2003-06-05
JP2002510680A (ja) 2002-04-09
AU3520799A (en) 1999-10-25
BR9909386A (pt) 2000-12-05

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