WO1999015511A1 - Triazines substituees, procedes permettant de les preparer et leur utilisation comme agents de lutte contre les parasites et comme fongicides - Google Patents

Triazines substituees, procedes permettant de les preparer et leur utilisation comme agents de lutte contre les parasites et comme fongicides Download PDF

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Publication number
WO1999015511A1
WO1999015511A1 PCT/EP1998/005985 EP9805985W WO9915511A1 WO 1999015511 A1 WO1999015511 A1 WO 1999015511A1 EP 9805985 W EP9805985 W EP 9805985W WO 9915511 A1 WO9915511 A1 WO 9915511A1
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alkyl
aryl
alkoxy
cycloalkyl
general formula
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PCT/EP1998/005985
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German (de)
English (en)
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Wolfgang Schaper
Ralf Braun
Harald Jakobi
Gerhard Krautstrunk
Martin Märkl
Oswald Ort
Herbert Stark
Manfred Kern
Ulrich Sanft
Werner Bonin
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Hoechst Schering Agrevo Gmbh
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Priority to AU96268/98A priority Critical patent/AU9626898A/en
Publication of WO1999015511A1 publication Critical patent/WO1999015511A1/fr

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    • 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
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/40—Six-membered ring containing nitrogen and carbon only
    • C10M133/42—Triazines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/04—Non-macromolecular organic compounds
    • C09K2200/0458—Nitrogen-containing compounds
    • C09K2200/0476—Heterocyclic nitrogen compounds, e.g. melamine
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C10M2215/222—Triazines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

  • the invention relates to new substituted 1,3,5-triazines, processes for their preparation and their use as pesticides and fungicides.
  • the invention therefore relates to compounds of formula (I) and their N-oxides and / or salts, preferably acid addition salts, wherein
  • R 1 and R 2 are identical or different and each is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C r C 6 ) haloalkyl, (C 3 -C 6 ) - Halocycloalkyl, halogen, Are (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl or (C 1 -C 4 ) cyanoalkyl;
  • X represents oxygen or NH
  • Q is a radical of the general formula Q 2 , Q 3 , Q 4 , Q 5 or Q 6 ;
  • n represents an integer from 2 to 7;
  • R 3 and R 4 are identical or different and denote hydrogen or methyl and R 5 is hydrogen, (C 1 -C 20 -alkyl, (C 1 -C 20 ) haloalkyl, (C 2 -C 20 ) alkenyl, (C 2 -C 20 ) - Alkynyl, (C r C 20 ) hydroxyalkyl, (C r C 20 ) cyanoalkyl, (C r C 20 ) nitroalkyl, (C r C 20 ) thiocyanalkyl, (C 3 -C 8 ) cycloalkyl , (C 3 -C 8 ) cycloalkenyl, (C 3 -C 8 ) cycloalkyl- (CC 4 ) alkyl, (C r C 4 ) alkyl- (C 3 -C 8 ) cycloalkyl, (C r C 20 ) alkoxy, (C r C 20 ) alkoxyalky,
  • R 6 , R 6 ' , R 7 are identical or different and are hydrogen, (C 1 -C 20 ) -alkyl, (C ⁇ C ⁇ ) - haloalkyl, (C 3 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl- (C r C 4 ) -alkyl, (C 2 -C 20 ) -alkenyl, (C 2 -C 20 ) -alkynyl, aryl, aryl- (C r is C 4 ) -alkyl, aryl- (C 2 -C 4 ) -alkenyl, aryl- (C 2 -C 4 ) -alkynyl, heteroaryl, heteroaryl- (C r C 4 ) -alkyl or R 6 and R 7 together form a ring system of the formula (III
  • D is saturated or aromatic;
  • m is an integer from 2 to 7;
  • q and r are identical or different and are integers between 0 and 4, the sum of which gives a number from 2 to 4, and in (III) a —CH 2 unit is optionally replaced by oxygen, sulfur or a grouping NR 9 , R 8 and R 9 are the same or different and are hydrogen, (C ⁇ Czoi-alkyl, (CC 20 ) -
  • Haloalkyl (C 3 -C 8 ) cycloalkyl, (C 1 -C 20 ) alkoxy, (C ⁇ C ⁇ alkylthio, phenyl-
  • R 4 has the meanings given above;
  • U is a direct bond or the group -CH 2 O-;
  • R 4 has the meanings given above
  • V is a direct bond, oxygen, S (O) 01 2 , OSO 2 or SO 2 O or VR 11 is one
  • R 6 and R 6 " have the meanings given above for R 6 ; and in the aromatic part of the condensed ring system of Q 3 optionally up to three, in the case of fluorine all hydrogen atoms are replaced by identical or different substituents;
  • R 4 has the meanings given above
  • A is a direct bond, oxygen or sulfur
  • B represents CH 2 , oxygen or sulfur, where in Q 4 at least one of the units A or B is oxygen or
  • R 12 has the meanings given above for R 6 , and if Q 4 is a
  • the radical R 12 is preferably in the cis position with respect to the pyrimidinyl-amino or -oxy radical, Q 5
  • R 13 represents aryl, heteroaryl, -CO-OR 14 , -CS-OR 14 or -CS-SR 14 ;
  • R 14 (C r C 20 ) alkyl, (C ⁇ C ⁇ haloalkyl, aryl- (C 1 -C 4 ) alkyl, aryl or
  • Heteroaryl means; where in all compounds of the formula (I) phenyl, aryl and heteroaryl radicals can be unsubstituted or substituted with up to three, in the case of fluorine as a substituent also up to the maximum number, further radicals, and in all to Q 1 - Q 6 , preferably Q 1 - Q 4 called alkyl, cycloalkyl, alkenyl or alkynyl groups and all groups derived therefrom which hydrogen atoms can partly, in the case of fluorine also completely, be replaced by halogen atoms, and in all to Q 1 - Q 6 , preferably Q. 1 - Q 4 , alkyl, alkenyl and alkynyl groups up to three non-adjacent saturated carbon units can be replaced by oxygen or the grouping S (O) 0 ⁇ 2 or Si (CH 3 ) 2 .
  • R 1 is preferably hydrogen or methyl, particularly preferably hydrogen.
  • R 2 is preferably (C r C 4 ) alkyl, (C r C 4 ) haloalkyl or (C 1 -C 4 ) alkoxyalkyl, particularly preferably methyl, ethyl, n-propyl or isopropyl.
  • R 3 , R 4 are preferably hydrogen.
  • X is preferably NH.
  • Q is preferably Q 1 .
  • Residues Q 1 in which the carbocycle is saturated are preferred.
  • R 5 is preferably (C r C 12 ) alkyl. (C 1 -C 8 ) haloalkyl, (C 3 -C 6 ) cycloalkyl, methyl (C 3 -C 8 ) cycloalkyl, (CC 8 ) alkoxy, (C 1 -C 8 ) alkoxy- ( C 1 -C 4 ) alkyl, (C r C 8 ) alkoxy, tri- (C 1 -C 5 ) alkylsilyl, preferably dimethyl- (C 1 -C 5 ) alkylsilyl, di- (C r C 5 ) alkyl- (C 3 -C 6 ) cycloalkylsilyl, preferably dimethylcyclohexylhexylsilyl, dimethyl- [mono-, di- or tris-oxa- (C 1 -C 12 ) alkyl] -silyl, - (C r C 5 ) -al
  • Aryl, aryl (C 1 -C 4 ) alkyl, aryloxy (C r C 4 ) alkyl, aryl (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, the above listed aryl or heteroaryl radicals and the radicals derived therefrom may be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals, -CO-R 6 , -COOR 6 , -CO-NR ⁇ R 7 .
  • R 5 is particularly preferred (C ⁇ C ⁇ alkyl, (C ⁇ C ⁇ haloalkyl, (C 3 -C 6 ) cycloalkyl, methyl (C 3 -C 8 ) cycloalkyl, (C r C 8 ) - Alkoxy, (C 1 -C 8 ) alkoxy- (C 1 -C 4 ) alkyl, tri- (C 1 -C 5 ) alkylsilyl, preferably dimethyl- (C 1 -C 5 ) alkylsilyl, dimethyl- [ mono-, di-, or tris-oxa - ⁇ - C ⁇ -alkylj-silyl, a group of the formula (II)
  • R 6 , R 6 ' , R 7 are preferably identical or different hydrogen, (C 1 -C 5 ) alkyl, aryl or R e and R 7 together form a ring system of the formula (III) or (IV), in the case of Formula (IV) preferably a tetrahydroisoquinoline system; m is preferably 4 or 5.
  • R 8 is preferably hydrogen, (C 1 -C 5 ) alkyl, benzyl or phenyl.
  • Phenyl, aryl or heteroaryl radicals and radicals derived therefrom are preferably unsubstituted or provided with one or more, preferably up to three, substituents.
  • alkyl, cycloalkyl, alkenyl or alkynyl groups mentioned in Q 1 and all groups derived therefrom hydrogen atoms can be replaced in part, in the case of fluorine completely, by halogen atoms, and - in all alkyl mentioned in Q 1 , Alkenyl and alkynyl groups up to three non-adjacent carbon units can be replaced by oxygen or the grouping S (O) 0> 1 ⁇ 2 or Si (CH 3 ) 2 .
  • Q 1 is particularly preferably a cyclohexyl group
  • R 3 and R 4 are hydrogen
  • the radical R 5 is in the 4-position with respect to the triazinylamino or alkoxy radicals and the two radicals on the cyclohexyl ring are in the cis position.
  • the following groups of compounds of the formula (Ia) - (If) are also preferred.
  • halogen means a fluorine, chlorine, bromine or iodine atom; under the expression “(C 1 -C 4 ) alkyl” an unbranched or branched
  • Hydrocarbon residue with 1 to 4 carbon atoms e.g. the methyl, ethyl,
  • Hexyl, heptyl, octyl or 1, 1, 3,3-tetramethylbutyl radical under the expression "(C 1 -C 12 )" - alkyl ", the aforementioned radical and, for example, the
  • Nonyl, decyl, undecyl or dodecyl radical under the expression "(C 1 -C 20 ) alkyl" the aforementioned alkyl radicals and, for example, the
  • Pentadecyl or eicosyl residue under the expression "(C 1 -C 4 ) haloalkyl” one under the expression “(C 1 -C 4 ) alkyl” Said alkyl group in which one or more hydrogen atoms are replaced by the above halogen atoms, preferably chlorine or fluorine, such as the trifluoromethyl group, the 1-fluoroethyl group, the
  • 2-fluoroethyl group the 1-fluoroisopropyl group, the 2,2,2-trifluoroisopropyl group, the 3,3,3-trifluoro-n-propyl group, the 2,2,2-trifluoroethyl group, the chloromethyl,
  • Fluoromethyl group the difluoromethyl group or the 1,2,2-tetrafluoroethyl group; 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
  • Nitroalkyl (CC 20 ) -thiocyanalkyl "eg one of the aforementioned (C r C 2 o) -
  • Alkyl groups in which one hydrogen is replaced by the nitro, cyano, thiocyano or hydroxyl group under the expression "(C 3 -C 8 ) cycloalkyl" the cyclopropyl, cyclobutyl or Cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical; under the expression "(C 3 -C 8 ) cycloalkenyl", for example a cyclobutenyl, cyclopentenyl,
  • Oxygen is replaced, e.g. the methoxy-methyl, -ethyl, -propyl-, -butyl-, -hexyl-,
  • Cyclohexylmethylthiomethyl or ethyl group under the term "DimethyHC ⁇ C ⁇ alkylsilyl" e.g. the trimethylsilyl,
  • Dimethyloctylsilyl group under the expression "dimethyl-tphenyl ⁇ C ⁇ C ⁇ -alkylj-silyl", for example the dimethylbenzylsilyl or the dimethylphenylethylsilyl group; under the expression “dimethyl- [mono-, di- or tris-oxa- (C 1 -C 12 ) alkyl] silyl, for example the
  • Phenylethyl the 1-methyl-1-phenylethyl group, the 3-phenylpropyl, the 4- Phenylbutyl group, the 2-methyl-2-phenyl-ethyl group or the 1-methyl or 2-
  • Methylnaphthyl group under the expression "aryl- (C 2 -C 4 ) -alkenyl" preferably the cinnamyl or styryl
  • aryl- (C 2 -C 4 ) alkynyl for example phenyl-ethynyl or
  • heteroaryl a heteroaromatic ring system
  • heteromatic ring system means 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 are replaced, e.g. a residue of thiophene, furan, pyrrole,
  • Benzisoxazole Benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole,
  • aryl preferably a carbocyclic aromatic radical
  • 6 to 14 in particular 6 to 12 carbon atoms, for example phenyl, naphthyl or
  • Biphenylyl preferably phenyl; under the term "heteroaryloxy” e.g. one of the heteroaryl
  • Residues linked via an oxygen atom under the expression "aryl (C 1 -C 4 ) alkoxy", for example the benzyloxy, phenyl ethoxy
  • phrasesylbutoxy or naphthylmethoxy group under the expression "heteroaryl (C 1 -C 4 ) alkyl", for example a thienyimethyl, furylmethyl, pyridinylmethyl, pyrimidinylmethyl or thiazolylmethyl group; under the expression “heteroaryl- (C 1 -C 4 ) alkoxy", for example a thienylmethoxy,
  • arylthio for example the phenylthio or the 1- or 2-naphthylthio Group
  • aryloxy for example the phenoxy or 1- or 2-naphthyloxy
  • heteroarylthio one of the heteroaromatic mentioned above
  • Residues linked by a sulfur atom under the expression "aryl (C 1 -C 4 ) alkylthio", for example the benzylthio, naphthylmethylthio or the phenylethylthio group; under the expression "HeteroaryKC ⁇ C ⁇ alkylthio" for example the thienylmethyl or
  • Phenylthioethyl, phenylthiobutyl or naphthylthiomethyl group under the expression "AryI- (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl", for example the benzylthiomethyl,
  • Benzylthioethyl or naphthylmethylthiomethyl group under the expression "heteroarylthio- (C 1 -C 4 ) alkyl", for example a pyridylthiomethyl,
  • the substituents (residues) with which the various aliphatic, aromatic and heterocyclic ring systems can be provided preferably include halogen, nitro, cyano, di- (C r C 4 ) -alkylaminio, (C r C 4 ) -alkyl, (C 3 -C 8 ) - Cycloalkyl, (CC 4 ) alkanoyl, (CrC ⁇ alkoxycarbonyl, (C 1 -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] 1 2 ethoxy, (C r C 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (C r C 4 ) -Alkylsulfonyl,
  • Haloalkyl groups such as the fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, 1-fluoroethyl, 2-fluoroethyl, 1, 1-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 3,3, 3-trifluoropropyl or the 1, 1, 1-trifluoroisopropyl group;
  • Haloalkoxy groups such as the difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy or the 2,2,2-trifluoroethoxy group;
  • Haloalkenyl residues such as the 1-fluoroethenyl, 2-fluoroethenyl, 1-fluoropropenyl, 2-
  • Halocycloalkyl radicals such as the 2,2-dichlorocyclopropyl or the 2,2-dichlorocyclopropyl or the 2,2-dichlorocyclopropyl or the 2,2-dichlorocyclopropyl or the 2,2-dichlorocyclopropyl or the 2,2-dichlorocyclopropyl or the 2,2-
  • Haloalkylthio residues such as the trifluoromethylthio residue
  • Haloalkylsulfinyl residues such as the trifluoromethylsulfinyl residue
  • Haloalkylsulfonyl radicals such as the trifluoromethylsulfonyl radical
  • Alkoxyalkyl radicals such as the methoxymethyl, ethoxymethyl, propoxymethyl
  • Alkoxyalkoxy radicals such as the methoxyethoxy or the ethoxyethoxy radical
  • Alkoxy-alkoxyalkyl radicals such as the ethoxy-ethoxymethyl radical
  • Alkoxyalkenyl radicals such as the 3-methoxy-propenyl or the 3-ethoxypropenyl radical
  • Alkoxy-alkynyl radicals such as the 3-methoxypropynyl or the 3-ethoxypropynyl radical;
  • Alkoxy-haloalkyl groups such as the 1-methoxy-2,2,2-trifluoroethyl; 1-ethoxy-2,2,2-trifluoroethyl-, 1-propoxy-2,2,2-thfluoroethyl-, 2-methoxy-1,1,1-trifluoro-2-propyl-, 2-
  • Haloalkoxy-alkyl groups such as the 2,2,2-trifluoroethoxymethyl or the
  • Haloalkox-haloalkyl groups such as the 2- (2,2,2-trifluoroethoxy) -1, 1,1-trifluoro-2-propyl group,
  • Aryloxy-haloalkyl groups such as the 2-phenoxy-1,1,1-trifluoro-2-propyl group or the 2- (p-tolyloxy) -1,1,1 -trifluoro-2-propyl group
  • Trialkylsilylalkyl residues such as the trimethylsilylmethyl, trimethylsilylethyl or the
  • the present invention relates to the compounds of formula (I) in the form of the free base or a salt, preferably an acid addition salt.
  • Acids which 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, trifluoroacetic acid, methanesulfonic acid , Benzenesulfonic acid, camphorsulfonic acid or toluenesulfonic acid.
  • the compounds of the formula I in some cases 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. by selective crystallization from suitable solvents or by chromatography, into which the components are separated. Racemates can be separated into the enantiomers by conventional methods, e.g. by salt formation with an enantiomer of a chiral 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
  • R 1 and R 2 have the meanings given under formula I and L represents a leaving group, with a nucleophile of the formula (VI), HX-Q (VI) in which X and Q have the meanings given above under formula I, and further derivatize the compounds of the formula I obtained in this way or otherwise, optionally on the heterocycle or in the side chain Q, and the compounds of the formula thus obtained (I) optionally converted into their salts.
  • the leaving group L can be varied within further 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, or alkoxy, such as methoxy, ethoxy, propoxy or isopropoxy or aryloxy, such as phenoxy or the trichloromethyl group.
  • a halogen atom such as fluor
  • the aforementioned reaction is carried out in a temperature range from 20 to 150 ° C. and, if the cleavage product HL has strongly acidic properties during the substitution, expediently 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
  • 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, Akali - or alkaline earth metal carbonates, bicarbonates, 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 the formula (VI) can also be used as an auxiliary base.
  • the nucleophiles of the formula (VI) required as starting products can be prepared by known processes, for example by reducing a keto group with a suitable reducing agent, for example a complex metal hydride or else with hydrogen and a hydrogenation catalyst.
  • a suitable reducing agent for example a complex metal hydride or else with hydrogen and a hydrogenation catalyst.
  • a suitable reducing agent for example a complex metal hydride or else with hydrogen and a hydrogenation catalyst.
  • the nucleophiles of the formula (VI) required as starting products can be prepared by known processes, for example by reducing an oxime or azide with a suitable reducing agent, for example a complex metal hydride or hydrogen in the presence of a hydrogenation catalyst Amination or Leuckart-Wallach reaction of a ketone or Gabriel reaction of an alkyl halide or tosylate.
  • a suitable reducing agent for example a complex metal hydride or hydrogen in the presence of a hydrogenation catalyst Amination or Leuckart-Wallach reaction of a ketone or Gabriel reaction of an alkyl halide or tosylate.
  • nucleophiles of the formula (VI) for which Q is one of the particularly preferred 6-ring derivatives are described, for example, in DE-A-42 08 254, DE-A-43 31 178, DE-A-44 17 163, DE-A-44 36 509, DE-A-44 37 137, DE-A-195 23 906, DE-A-196 13 329 and DE- A-196 14 718.
  • the starting materials of the formula (V) are known or can be prepared analogously to known processes (see e.g. Helv. Chim. Acta SS, 1365 (1950); J. Amer. Chem. 78, 2447 (1956)).
  • the active ingredients are suitable for good plant tolerance and cheaper
  • 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.
  • 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 ..
  • the plant-parasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as those of the genera Meloidogyne (root-bile nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera, or globodera or pallid nodules, cystic nodules, Heterodera trifolii) and the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus),
  • the genera Meloidogyne root-bile nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica
  • Tylenchulus (like Tylenchulus semipenetrans), Tylenchorhynchus (like Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (like Rotylenchus robustus), Heliocotylenchus (like Haliocotylenchus multicinctus), Belonoaimus (like Belonoaimus longicaudatus), Longidorus (like Longidorus elongatus), Trichodorus (like Trichodorus primitivus) and 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 insecticides 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 from 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 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 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 wetting agents, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium.
  • wetting agents e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-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 or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, Sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.
  • 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 esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. 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, 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 generally about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components.
  • the active compound concentration can generally be about 5 to 80% by weight.
  • Dust-like formulations generally contain 5 to 20% by weight of active ingredient, sprayable solutions about 2 to 20% by weight.
  • 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, for example in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also in the case of 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.
  • 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
  • Alanylcarb (OK-135), Aldicarb, 2-sec-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;
  • Fluvalinate (D-isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, pheothrin ((R-isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin (TD , Tralomethrin, transfluthrin, zeta-cypermethrin (F-56701);
  • 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 of the formula (I) according to the invention are also suitable for combating endo- 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.
  • novel compounds of the 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 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 beneficial in such fungal diseases, which can no longer be effectively combated after the infection has occurred with the usual fungicides.
  • the spectrum of activity of the claimed compounds covers various economically important phytopathogenic fungi, such as Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Piricularia oryzae, Pyrenophora teres, Leptosphaerea nodorum and Pellikularia 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, azoxystrobin, azaconazole, BAS 450F, benalaxyl, benodanil, benomyl, bethoxazine, binapacryl, bion (CGA- 245704), bitertanol, bromuconazole, buthiobate, captafol, captan, carbendazim, carboxin, carpropamide, CGA 173506, cymoxanil, cyproconazole, cyprodinil, cyprofuram, diflumetorim, dichlorfluanid, dichlormezin, diclobutazolone, diclobutrazol, diclobutrazole, (CGA 169374), Difluconazole, Dimethirimol, Dimethomorph, Diniconazole,
  • the above-mentioned combination partners are known active ingredients, which are largely described in The Pesticide Manual (Editor: Clive Tomlin), 11th edition (1997), Crop Protection Publications / ISBN 1-901396-11-8 795.
  • 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 1 and 50% by weight.
  • the application takes place in a Application forms customary usual way.
  • the compounds of formula (I) can also be used to control harmful plants 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.
  • 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 to 60 ° C RH). After 6 days of storage, the effect of the preparation on all stages of the spider mite is determined.
  • the preparations according to Example Nos. 9, 18, 23, 45, 46, 49, 50, 52, 53, 82 and 83 cause 90 to 100% mortality.
  • a petri dish the bottom of which is covered with filter paper and contains about 5 ml of nutrient medium, is prepared.
  • Five L2 larvae of the Egyptian cottonworm (Spodoptera litoralis) 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 traded 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.
  • the preparation according to Example Nos. 37, 45 and 52 cause 90 to 100% mortality of the larvae.
  • a petri dish the bottom of which is lined 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.
  • the preparations according to Example Nos. 9, 13, 24, 37, 38, 45, 49, 50, 53, 82, 306 and 307 bring about a 90 to 100% strength 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 then immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated. After draining, plants and animals are stored in a climatic chamber (16 hours light / day, 25 ° C, 40 to 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 Nos. 9, 13, 24, 37, 45, 52, 53 and 82 cause 90 to 100% mortality of the aphids.
  • Example E Example E
  • 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. After draining, the rice plants treated in this way are 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 is stored in a climatic chamber (16 hours light / day, 25 ° C, 40 to 60% RH). After 6 days of storage, the mortality of the leafhopper larvae is determined. At a concentration of 300 ppm (based on the active ingredient content), the preparation according to Example Nos. 9, 23, 37, 50, 52, 53, 82 and 83 causes 90 to 100% mortality.
  • 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, this 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 Nos. 9, 13, 24, 37, 38, 49, 50, 52 and 53 cause 90 to 100% mortality. Use as an anti-parasitic
  • the active substances were dissolved in 10% (w / v) 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 dissolved in water diluted a test concentration of 1000 ppm.
  • the ticks were then dried on filter paper and then for the purpose of laying eggs with the back on an adhesive film.
  • the ticks were stored in a warming cabinet at 28 ° C and a humidity of 90%.
  • the compounds were tested for activity against one or more of the following organisms: Plasmopora graminis f. sp. tritici Pyricularia oryzae Leptosphaeria nodorum Phytophthora infestans
  • 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 infested plant was assessed visually.
  • the compounds are rated on a scale from 1 to 3, in which 1 means no to little control, 2 medium control and 3 good to complete. At a concentration of 500 ppm or less, the following compounds were rated 2 or higher against the listed fungi.

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Abstract

L'invention concerne des cycloalkylamino- et des cycloalcoxy-1,3,5-triazines substituées de la formule générale (I), des procédés permettant de les préparer, des agents les contenant et leur utilisation pour lutter contre des parasites animaux, notamment des insectes, des tétranyques, des ectoparasites et des helminthes. Dans la formule générale (I), Q désigne cycloalkyle éventuellement substitué, X désigne O et NH, et R1 et R2 désignent différents restes organiques.
PCT/EP1998/005985 1997-09-22 1998-09-19 Triazines substituees, procedes permettant de les preparer et leur utilisation comme agents de lutte contre les parasites et comme fongicides WO1999015511A1 (fr)

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AU96268/98A AU9626898A (en) 1997-09-22 1998-09-19 Substituted triazines, method for producing said substituted triazines, and use of the same as pesticides and fungicides

Applications Claiming Priority (2)

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DE19741654.3 1997-09-22
DE19741654A DE19741654A1 (de) 1997-09-22 1997-09-22 Substituierte Triazine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010055078A1 (fr) * 2008-11-13 2010-05-20 Bayer Cropscience Sa Derives heterocyclyl-triazinyl-amine fongicides

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EP0336494A2 (fr) * 1988-04-07 1989-10-11 Shell Internationale Researchmaatschappij B.V. Triazines pour utilisation comme herbicides
EP0483985A1 (fr) * 1990-10-25 1992-05-06 Zeneca Limited Fongicides
DE4208254A1 (de) * 1992-03-14 1993-09-16 Hoechst Ag Substituierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel und fungizid
DE4417163A1 (de) * 1994-05-17 1995-11-23 Hoechst Schering Agrevo Gmbh Heterocyclylamino- und Heterocyclyloxy-cycloalkyl-Derivate, ihre 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
DE19523906A1 (de) * 1995-06-30 1997-01-02 Hoechst Schering Agrevo Gmbh Substituierte 1,3-Dioxan-5-ylamino-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
DE19613329A1 (de) * 1996-04-03 1997-10-09 Hoechst Schering Agrevo Gmbh Substituierte Pyridine/Pyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
DE19614718A1 (de) * 1996-04-15 1997-10-16 Hoechst Schering Agrevo Gmbh Substituierte Pyridine/Pyrimidine, Verfahren zu ihrer Herstellung, und ihre Verwendung als Schädlingsbekämpfungsmittel

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Publication number Priority date Publication date Assignee Title
EP0336494A2 (fr) * 1988-04-07 1989-10-11 Shell Internationale Researchmaatschappij B.V. Triazines pour utilisation comme herbicides
EP0483985A1 (fr) * 1990-10-25 1992-05-06 Zeneca Limited Fongicides
DE4208254A1 (de) * 1992-03-14 1993-09-16 Hoechst Ag Substituierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel und fungizid
DE4417163A1 (de) * 1994-05-17 1995-11-23 Hoechst Schering Agrevo Gmbh Heterocyclylamino- und Heterocyclyloxy-cycloalkyl-Derivate, ihre 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
DE19523906A1 (de) * 1995-06-30 1997-01-02 Hoechst Schering Agrevo Gmbh Substituierte 1,3-Dioxan-5-ylamino-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
DE19613329A1 (de) * 1996-04-03 1997-10-09 Hoechst Schering Agrevo Gmbh Substituierte Pyridine/Pyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
DE19614718A1 (de) * 1996-04-15 1997-10-16 Hoechst Schering Agrevo Gmbh Substituierte Pyridine/Pyrimidine, Verfahren zu ihrer Herstellung, und ihre Verwendung als Schädlingsbekämpfungsmittel

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010055078A1 (fr) * 2008-11-13 2010-05-20 Bayer Cropscience Sa Derives heterocyclyl-triazinyl-amine fongicides
CN102216287A (zh) * 2008-11-13 2011-10-12 拜尔农科股份公司 杀真菌剂杂环基-三嗪基-氨基衍生物

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