Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/81—Amides; Imides
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • 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
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
  • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
  • A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
  • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
  • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/10—Antimycotics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/10—Anthelmintics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/14—Ectoparasiticides, e.g. scabicides
• • 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
• • 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
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/08—Bridged systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0803—Compounds with Si-C or Si-Si linkages
  • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
  • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

• Heterocyclic amides processes for their preparation, compositions containing them and their use
• the invention relates to heterocyclic amides, processes for their preparation, compositions containing them and their use for controlling animal pests, in particular arthropods, such as insects and acarina, and helminths.
• insecticides or repellents are still indispensable because of the enormous damage that insects cause, for example, by eating crops, food supplies, wood and textiles or by transmitting disease to humans, pets and crops.
• Insecticides are an important part of integrated pest control and make a decisive contribution to crop yield and continuity of harvests all over the world.
• X is CH or N; Y is O or S; n is 0 or 1;
• R 1 is (C 1 -C 4 ) haloalkyl
• R 2 , R 3 are independently hydrogen, (C 1 -C 4 ) alkyl, (CC 4 ) haloalkyl or halogen;
• R 4 is hydrogen, (CrC-alkyl, (C 3 -C 10 ) -cycloalkyl, (C 3 -C 10 ) -alkenyl, or (C 3 -C 10 ) -alkynyl, in which alkyl-, cycloalkyl- , Alkenyl or alkynyl groups up to three hydrogen atoms can be replaced by halogen, preferably fluorine or chlorine, in the case of fluorine also up to the maximum number;
• R 5 is an aliphatic heterocycle, which is preferably four to eight-membered, containing at least one Oxygen, sulfur, nitrogen and / or silicon ring atom, and which can optionally be part of a spirocyclic, condensed or bicyclic ring system.
• R 5 is preferably a four- to eight-membered aliphatic heterocycle which has an oxygen ring atom, a sulfur ring atom, a nitrogen ring atom, a silicon ring atom, two oxygen ring atoms or two sulfur ring atoms, the sulfur ring atoms being in the form -S (0) p -, and p 0 , 1 or 2 means.
• R 5 is very particularly preferably a four- to eight-membered heteroaliphatic radical of the formula (II),
• a and / or B is a unit containing at least one oxygen, sulfur, nitrogen or silicon ring atom, preferably -O-, -S (O) 01 2 -, -NR 8 - or -SiR 9 R 10 -, and the Ring can additionally contain one or two carbonyl groups, which together with the hetero units optionally form a lactone, lactam or imide unit; and, if A is oxygen and B is -NR 8 -, these units can be immediately adjacent and in all other cases for which A and B are heteroatom units they must be separated by at least one saturated carbon unit; m denotes 0 or 1 to 6, preferably 0, 1 or 2,
• R 6 is the same or different depending on m and each represents a monovalent substituent of the heterocycloaliphatic ring, such as (CC 10 ) alkyl, (C 2 -C 10 ) alkenyl, (C 2 -C 10 ) alkynyl, (C 3 -C 10 ) - cycloalkyl, (C 4 -C 10 ) cycloalkenyl or (C 8 -C 10 ) cycloalkynyl, which can each be substituted by one or more identical or different radicals, or a radical R 7 , where R 7 Halogen, cyano, nitro, hydroxy, thio, amino, (C 1 -C 10 ) alkanoyl, (C 3 -
• R 11 has the meanings given above for R 7 ;
• R 8 is hydrogen, (C 1 -C 10 ) alkyl, (C 3 -C 10 ) alkenyl, (C 3 -C 10 ) alkynyl, (C 3 -C 10 ) -
• X is preferably -CH-.
• Y is preferably -O-.
• n is preferably 0.
• R 1 is preferably substituted one or more times by F and / or Cl
• R 2 , R 3 are preferably hydrogen.
• R 4 is preferably hydrogen and methyl, particularly preferred
• R 6 (C 1 -C 10 ) alkyl, (C 2 -C 10 ) alkenyl, (C 2 -C 10 ) alkynyl, (C 3 -C 10 ) cycloalkyl, (C '4,
• R 5 is preferably a five- to seven-membered aliphatic heterocycle having one or two heteroatom units A and / or B, very particularly preferably a five- to seven-membered aliphatic Heterocycle with one or two heteroatom unit (s) and optionally additionally a carbonyl group in the ring, which together with a hetero unit forms a lactone or lactam unit.
• C 4 ) -alkyl-arylamino the N- (C 1 -C 4 ) -alkylamino analogues of the latter two radicals, AryI- (C 1 -C 4 ) -alkoxy, aryl- (C 3 -C 4 ) -alkenyloxy , Aryl- (C 1 -C 4 ) -alkylthio, aryl- (C 3 -C 4 ) -alkenylthio, aryl- (C 1 -C 4 ) -alkylamino, aryl- (C 3 -C 4 ) -alkenylamino, the N- (C 1 -C 4 ) -alkylamino analogs of the latter radical, aryl- (C 1 -C 8 ) -dialkylsilyl, diaryl- (C 1 -C 8 ) -alkylsilyl, triarylsilyl, heterocyclyl, heterocycly
• R 8 is (C, -C 4 ) -alkyl, (C r C 4 ) -alkanoyl, (C 1 -C 4 ) -alkoxycarbonyl, (C r C 4 ) -
• Alkylsulfonyl or (C ⁇ C -dialkylcarbamoyl means.
• Heteroatom unit is A or B and this heteroatom unit preferably oxygen; Is sulfur, S (O) or S (0) 2 and, if A or B is oxygen, optionally with an additional one
• Lactone group forms.
• halogen includes fluorine, chlorine, bromine, iodine.
• (C 1 -C 4 ) alkyl is to be understood as an unbranched or branched aliphatic and saturated hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as. B. the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, isobutyl or tert-butyl radical.
• alkyl radicals with a larger range of carbon atoms are understood to mean an unbranched or branched aliphatic and saturated hydrocarbon radical which contains a number of carbon atoms which corresponds to this range specification.
• the expression "(C 1 -C 10 ) alkyl” accordingly includes the aforementioned alkyl radicals, and z. B. the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl, octyl, tert-octyl, nonyl or decyl radical.
• (CC 4 ) -Haloalkyl is to be understood as an alkyl group mentioned under the expression "(C 1 -C 4 ) alkyl” in which one or more hydrogen atoms are represented by the same number of identical or different halogen atoms, preferably chlorine or fluorine, are replaced, such as the trifluoromethyl, the 1- or 2-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl or the 1, 1, 2,2-tetrafluoroethyl group.
• halogen atoms preferably chlorine or fluorine
• alkenyl and alkynyl with a prefixed range of carbon atoms mean a straight-chain or branched hydrocarbon radical with a number of carbon atoms corresponding to this range, which contains at least one multiple bond, where it can be located at any position of the unsaturated residue in question.
• (C 3 -C 10 ) alkenyl thus stands for example for the allyl, 2-methylpropenyl, 1- or 2-butenyl, pentenyl, 2-methylpentenyl, hexenyl, heptenyl, octenyl, nonenyl - or decenyl group.
• (C 2 -C 10 ) alkenyl is e.g. B. for the aforementioned groups, and in addition the vinyl group.
• (C 3 -C 10 ) Alkynyl stands for example for the propargyl, 2-methylpropinyl, 2-butynyl, pentynyl, 2-methylpentynyl, hexynyl, heptynyl, octynyl, nonynyl or the decynyl - Group.
• (C 2 -C 10 ) Alkynyl means the radicals mentioned above and the ethynyl group.
• (C 3 -C 10 ) cycloalkyl stands for monocyclic and saturated alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl or cyclodecyl radical; for bicyclic and saturated alkyl radicals, such as the norbornyl or bicyclo [2.2.2] octyl radical, or also for condensed and saturated systems, such as. B. the decahydronaphthyl residue.
• (C 3 -C 10 ) cycloalkenyl stands for monocyclic alkyl radicals containing at least one multiple bond, such as the cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl or cyclodecenyl radical; for bicyclic alkyl radicals containing at least one multiple bond, such as de ⁇ norbomenyl or bicyclo [2.2.2] octenyl radical, or also for condensed systems containing at least one multiple bond, such as, for. B. the tetra, hexa or octahydronaphthyl radical.
• Cycloalkinyf stands for the cyclooctinyl, cyclononinyl or cyclodecinyl radical.
• (C 1 -C 10 ) alkanoyl stands for example for the formyl, acetyl, propionyl, butyryl, 2-methylbutyryl, pivaloyl, octanoyl or decanoyl group.
• (C 3 -C 10 ) alkenoyl stands for example for the acrylic, methacrylic, crotonoyl, dimethylacryl or octenoyl group.
• (C 3 -C 10 ) alkynoyl stands for example for the propinoyl, butinoyl, hexinoyl or octinoyl group.
• (C 3 -C 10 ) Cycloalkanoyl stands for example for cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl or cyclooctylcarbonyl.
• (C 3 -C 10 ) alkenyloxy "(C 3 -C 10 ) alkynyloxy", “(C 3 -C 10 ) cycloalkoxy” and “(C 4 -C 10 ) cycloalkenyloxy” are alkoxy groups to understand, the hydrocarbon radicals of which under the terms "(C 3 -C 10 ) alkenyl", “(C 3 -C 10 ) alkynyl", “(C 3 -C 10 ) cycloalkyl” and "(C 4 - C 10 ) -cycloalkenyl "have meanings.
• (C 4 -C 8 ) cycloalkenyl (C r C 4 ) alkoxy represents, for example, the cyclobutenyl methoxy, cyclopentenyl methoxy, cyclohexenyl methoxy or the cyclohexenylethoxy group.
• (C 3 -C 8 ) Cycloalkyl- (C 3 -C 4 ) alkenyloxy stands for example for the cyclopropylallyloxy, cyclobutylallyloxy or the cyclopentylallyloxy group.
• (C 4 -C 8 ) Cycloalkenyl- (C 3 -C 4 ) alkenyloxy represents, for example, the cyclobutenylallyloxy or the cyclopentenylallylpxy group.
• (C 1 -C 4 ) Alkyl (C 3 -C 8 ) cycloalkoxy represents, for example, the methylcyclopentyloxy, ethylcyclopentyloxy, methylcyclohexyloxy or the ethylcyclohexyloxy group.
• (C 2 -C 4 ) alkenyl (C 3 -C 8 ) cycloalkoxy represents, for example, the vinylcyclopentyloxy, allylcyclopentyloxy, vinylcyclohexyloxy or the allylcyclohexyloxy group.
• (C 2 -C 4 ) Alkynyl (C 3 -C 8 ) cycloalkoxy stands for example for the ethynylcyclopentyloxy, propynylcyclopentyloxy, ethynylcyclohexyloxy or the propynylcyclohexyloxy group.
• (C 1 -C 4 ) Alkyl (C 4 -C 8 ) cycloalkenyloxy stands for example for the methylcyclopentenyloxy, ethylcyclopentenyloxy, methylcyclohexenyloxy or the ethylcyclohexenyloxy group.
• (C 2 -C 4 ) alkenyl (C 3 -C 8 ) cycloalkoxy represents, for example, the vinylcyclopentyloxy, allylcyclopentyloxy, vinylcyclohexyloxy or the allylcyclohexyloxy group.
• (C 2 -C 4 ) alkenyl (C 3 -C 8 ) cycloalkenyloxy represents, for example, the vinylcyclopentenyloxy, allylcyclopentenyloxy, vinylcyclohexenyloxy or the allylcyclohexenyloxy group.
• (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkoxy means an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, the ethoxy methoxy, 1 - Methoxyethoxy, 1-ethoxyethoxy or the 1-methoxypropoxy group.
• (C 1 -C 4 ) alkoxy- (C 3 -C 4 ) alkenyloxy means e.g. B. the methoxyallyloxy or the ethoxyallyloxy group.
• (C 1 -C 8 ) mono- or dialkylcarbamoyl means, for example, the methyl, ethyl, propyl, isopropyl, butyl or tert-butyl carbamoyl group or the dimethyl, diethyl, Methyl ethyl or the diisopropylcarbamoyl group, but also cyclic derivatives such as. B. the pyrrolidino or the piperidino carbamoyl group.
• (C 3 -C 8 ) mono- or dicycloalkylcarbamoyl means, for example, the cyclopropyl, cyclobutyl, cyclopentyl or cyclohexylcarbamoyl group, or the dicyclopropyl, dicyclobutyl, dicyclopentyl or dicyclohexylcarbamoyl group.
• (C 1 -C 8 ) alkoxycarbonyl means e.g. B. the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarboiyl or the tert. Butoxycarbonyl group.
• (C 3 -C 8 ) cycloalkoxycarbonyl means e.g. B. the cyclopropoxycarbonyl, cyclobutoxycarbonyl, cyclopentyloxycarbonyl or the cyclohexyloxycarbonyl group.
• (C ⁇ C ⁇ -alkanoyloxy) means, for example, the acetoxy, propionyloxy, butanoyloxy or the pivaloyloxy group.
• (C 3 -C 8 ) cycloalkanoyloxy means e.g. B. the cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or the cyclohexylcarbonyloxy group.
• (C 1 -C 8 ) alkanoylamino means e.g. B. the formylamino, acetylamino, propionylamino, isopropionylamino, butanoylamino or the pivaloylamino group.
• (C 3 -C 8 ) alkenoylamino means e.g. B. the acrylamino, methacrylamino, dimethylacrylamino or the crotonylamino group.
• (C 3 -C 8 ) -CycIoalkanoyIamino means e.g. B. the cyclopropanoylamino, cyclobutanoylamino, cyclopentanoylamino or the cyclohexanoylamino group.
• (C 3 -C 8 ) cycloalkyl (CC 4 ) alkanoylamino means e.g. B. the cyclopropylacetylamino or the cyclopentylacetylamino group.
• (C 1 -C 10 ) Alkylthio stands for an alkylthio group whose hydrocarbon radical has the meaning given under the expression “(C ⁇ C ⁇ alkyl”).
• (C 3 -C 10 ) alkenylthio stands for an alkenylthio group whose hydrocarbon radical has the meaning given under the expression "(C 3 -C 10 ) alkenyl”.
• (C 3 -C 10 ) alkynylthio stands for an alkynylthio group whose hydrocarbon radical has the meaning given under the expression "(C 3 -C 10 ) alkynyl”.
• (C 3 -C 10 ) cycloalkylthio stands for a cycloalkylthio group whose hydrocarbon radical has the meaning given under the expression "(C 3 -C 10 ) cycloalkyl”.
• (C 4 -C 10 ) cycloalkenylthio stands for a cycloalkenylthio group whose hydrocarbon radical has the meaning given under the expression "(C 4 -C 10 ) cycloalkenyl”.
• (C 3 -C 8 ) Cycloalkyl- (C r C 4 ) alkylthio stands for example for the cyclopropylmethylthio, cyclopropylethylthio, cyclopentylmethylthio or the cyclohexylmethylthio group.
• (C 4 -C 8 ) -CycloaIkenyl- (CC 4 ) alkylthio stands for example for the cyclopentenylmethylthio or the cyclohexenylmethylthio group.
• (C 3 -C 8 ) Cycloalkyl- (C 3 -C 4 ) alkenylthio stands for example for the cyclopropylallylthio, cyclopentylallylthio or the cyclohexylallylthio group.
• (C 4 -C 8 ) Cycloalkenyl- (C 3 -C 4 ) alkenylthio stands for example for the cyclopentenylallylthio or the cyclohexenylallylthio group.
• (C 1 -C 4 ) alkyl (C 3 -C 8 ) cycloalkylthio stands for example for the methylcyclopentylthio or the methylcyclohexylthio group.
• (C 1 -C 4 ) Alkyl- (C 4 -C 8 ) -cycloalkenylthio stands for example for the methylcyclopentenylthio or the methylcyclohexenylthio group.
• (C 2 -C 4 ) alkenyl (C 3 -C 8 ) cycloalkylthio stands for example for the vinylcyclopentylthio, allylcyclopentylthio, vinylcyclohexylthio or the allylcyclohexylthio group.
• (C 2 -C 6 ) Alkynyl (C 3 -C 8 ) cycloalkylthio stands for example for the ethynylcyclopentylthio, propargylcyclopentylthio, ethynylcyclohexylthio or the propargylcyclohexylthio group.
• (C 2 -C 4 ) alkenyl (C 4 -C 8 ) cycloalkenylthio stands for example for the allylcyclopentenylthio or the allylcyclohexenylthio group.
• (C ⁇ C ⁇ alkylsulfinyl) represents the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl or octylsulfinyl group.
• (C 3 -C 8 ) alkenylsulfinyl stands for example for the allyl, methylallyl, butenyl or octenylsulfinyl group.
• (C 3 -C 8 ) Alkynylsulfinyl stands for example for the propargyl, butynyl or octynylsulfinyl group.
• (C 3 -C 10 ) Cycloalkylsulfinyl stands for a cycloalkylsulfinyl group whose hydrocarbon radical has the meaning given under the expression "(C 3 -C 10 ) cycloalkyl”.
• (C 4 -C 10 ) Cycloalkenylsulfinyl stands for a cycloalkenylsulfinyl group, the hydrocarbon radical of which has the meaning given under the expression "(C 4 -C 10 ) Cycloalkenyl”.
• (C 3 -C 8 ) Cycloalkyl- (CC 4 ) alkylsulfinyl stands for example for the cyclopropylmethylsulfinyl, cyclopropylethylsulfinyl, cyclopentylmethylsulfinyl or the cyclohexylmethylsulfinyl group.
• (C 4 -C 8 ) -cycloalkenyl- (C r C 4 ) -alkylsulfinyl stands for example for the cyclopentenylmethylsulfinyl or the cyclohexenylmethylsulfinyl group.
• (C 3 -C 8 ) Cycloalkyl- (C 3 -C 4 ) alkenylsulfinyl stands for example for the cyclopropylallylsulfinyl, cyclopentylallylsulfinyl or the cyclohexylallylsulfinyl group.
• (C 4 -C 8 ) -cycloalkenyl- (C 3 -C 4 ) -alkenylsulfinyl stands for example for the cyclopentenylallylsulfinyl or the cyclohexenylallylsulfinyl group.
• (CC 4 ) alkyl (C 3 -C 8 ) cycloalkylsulfinyl stands for example for the methylcyclopentylsulfinyl or the methylcyclohexylsulfinyl group.
• (C 2 -C 4 ) alkenyl (C 3 -C 8 ) cycloalkylsulfinyl stands for example for the vinylcyclopentylsulfinyl, allylcyclopentylsulfinyl, vinylcyclohexylsulfinyl or the allylcyclohexylsulfinyl group.
• (C 2 -C 4 ) Alkynyl (C 3 -C 8 ) cycloalkyisulfinyl stands for example for the ethynylcyclopentylsulfinyl, propargylcyclopentylsulfinyl, ethynylcyclohexylsulfinyl or the propargylcyclohexylsulfinyl group.
• (C 2 -C 4 ) alkenyl (C 4 -C 8 ) cycloalkenylsulfinyl stands for example for the vinylcyclopentenylsulfinyl, allylcyclopentenylsulfinyl, vinylcyclohexenylsulfinyl or the allylcyclohexenylsulfinyl group.
• (CC 10 ) alkylsulfonyl stands for example for the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl or octylsulfonyl group.
• (C 3 -C 10 ) alkenylsulfonyl stands for example for the allyl, methylallyl, butenyl or octenylsulfonyl group.
• (C 3 -C 10 ) alkynylsulfonyl stands for example for the propargyl, butynyl or octynylsulfonyl group.
• (C 3 -C 10 ) cycloalkylsulfonyl stands for a cycloalkylsulfonyl group whose hydrocarbon radical has the meaning given under the expression "(C 3 -C 10 ) cycloalkyl”.
• (C 4 -C 10 ) Cycloalkenylsulfonyl stands for a cycloalkenylsulfonyl group whose hydrocarbon radical has the meaning given under the expression "(C 4 -C 10 ) cycloalkenyl”.
• Cycloalkyl- (C, -C 4 ) alkylsulfonyr stands for example for the cyclopropylmethylsulfonyl, cyclopropylethylsulfonyl, cyclopentylmethylsulfonyl or the cyclohexylmethylsulfonyl group.
• (C 4 -C 8 ) Cycloalkenyl- (C 1 -C 4 ) alkylsulfonyl stands for example for the cyclopentenylmethylsulfonyl or the cyclohexenylmethylsulfonyl group.
• (C 3 -C 8 ) Cycloalkyl- (C 3 -C 4 ) alkenylsulfonyl stands for example for the cyclopropylallylsulfonyl, cyclopentylallylsulfonyl or the cyclohexylallylsulfonyl group.
• (C 4 -C 8 ) Cycloalkenyl (C 3 -C 4 ) alkenylsulfonyl stands for example for the cyclopentenylallylsulfonyl or the cyclohexenylallylsulfonyl group.
• (C 1 -C 4 ) -Alkyl- (C 3 -C 8 ) -cycloalkylsulfonyl stands for example for the methylcyclopentylsulfonyl or the methylcyclohexylsulfonyl group.
• (C r C 4 ) alkyl (C 4 -C 8 ) cycloalkenylsulfonyr represents, for example, the methylcyclopentenylsulfonyl or methylcyclohexenylsulfonyl group.
• (C 2 -C 4 ) alkenyl (C 3 -C 8 ) cycloalkylsulfonyl stands for example for the vinylcyclopentylsulfonyl, allylcyclopentylsulfonyl, vinylcyclohexylsulfonyl or the allylcyclohexylsulfonyl group.
• (C 2 -C 4 ) alkynyl (C 3 -C 8 ) cycloalkylsulfonyl stands for example for the ethynylcyclopentylsulfonyl, propargylcyclopentylsulfonyl, ethynylcyclohexylsulfonyl or the propargylcyclohexylsulfonyl group.
• (C 2 -C 4 ) alkenyl (C 4 -C 8 ) cycloalkenylsulfonyl stands for example for the vinylcyclopentenylsulfonyl, allylcyclopentenylsulfonyl, vinylcyclohexenylsulfonyl or the allylcyclohexenylsulfonyl group.
• (C 1 -C 10 ) alkylamino stands for a nitrogen atom which is substituted by one or two, identical or different alkyl radicals of the above definition.
• (C 3 -C 10 ) alkenylamino represents a nitrogen atom which is substituted by one or two, identical or different alkenyl radicals of the above definition.
• (C 3 -C 10 ) Alkynylamino represents a nitrogen atom which is substituted by one or two, identical or different alkynyl radicals of the above definition.
• (C 3 -C 8 ) Cycloalkylamino stands for a nitrogen atom which is substituted by one or two, identical or different cycloalkyl radicals of the above definition.
• (C 3 -C 8 ) Cycloalkyl- (C 1 -C 4 ) alkylamino stands for example for the cyclopropylmethylamino, cyclopropylethylamino, cyclopentylmethylamino or the cyclohexylmethyamino group.
• (C 4 -C 8 ) Cycloalkenyl- (C 1 -C 4 ) alkylamino stands for example for the cyclopentenylmethylamino or the cyclohexenylmethylamino group.
• (C 3 -C 8 ) Cycloalkyl- (C 3 -C 4 ) alkenylamino stands for example for the cyclopropylallylamino-cyclopentylallylamino or the cyclohexylallylamino group.
• (C 4 -C 8 ) Cycloalkenyl- (C 3 -C 4 ) alkenylamino stands for example for the cyclopentenylallylamino or the cyclohexenylallylamino group.
• (C 1 -C 4 ) Alkyl- (C 3 -C 8 ) -cycloalkylamino stands for example for the methylcyclopentylamino or the methylcyclohexylamino group.
• (C 1 -C 8 ) Alkyl- (C 4 -C 8 ) -cycloalkenylamino stands for example for the methylcyclopentenylamino or the methylcyclohexenylamino group.
• (C 2 -C 4 ) alkenyl (C 3 -C 8 ) cycloalkylamino stands for example for the vinylcyclopentylamino, allylcyclopentylamino, vinylcyclohexylamino or the allylcyclohexylamino group.
• (C 2 -C 4 ) Alkynyl (C 3 -C 8 ) cycloalkylamino stands for example for the ethynylcyclopentylamino, propargylcyclopentylamino, ethynylcyclohexylamino or the propargylcyclohexylamino group.
• (C 2 -C 4 ) alkenyl (C 4 -C 8 ) cycloalkenylamino stands for example for the vinylcyclopentenylamino, allylcyclopentenylamino, vinylcyclohexenylamino or the allylcyclohexenylamino group.
• N-substituted amino groups In addition to simply N-substituted amino groups, the corresponding N, N-disubstituted derivatives are also included, in particular derivatives in which a hydrogen is replaced by a (C 1 -C 4 ) -alkyl group.
• (C ⁇ C ⁇ J-trialkylsilyl means a silicon atom which carries three identical or different alkyl radicals as defined above.
• aryl- (C 1 - C 6 ) -dialkylsilyl stand for a silicon atom which is an aryl radical and carries two identical or different alkyl radicals as defined above
• diaryl- (C 1 -C 6 ) alkylsilyl for a silicon atom which carries an alkyl radical and two identical or different aryl radicals as defined above
• triarylsilyl for a Silicon atom bearing three identical or different aryl radicals as defined above.
• aryl is a carbocyclic, i.e. aromatic radical composed of carbon atoms and preferably having 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl.
• Aroyl therefore means an aryl radical as defined above which is bonded via a carbonyl group, such as e.g. the benzoyl group.
• four- to eight-membered aliphatic heterocycle containing at least one oxygen, sulfur, nitrogen and / or silicon ring atom stands for a cyclic radical which can be completely saturated or partially unsaturated but not aromatic and which can be substituted by one or more, The same or different, preferably one or two, atoms from the group nitrogen, sulfur, oxygen and silicon is interrupted, but not two Oxygen atoms may be directly adjacent.
• the heterocycle has four to eight ring atoms, which are carbon atoms in addition to the heteroatoms mentioned above.
• heterocyclyl preferably stands for a cyclic radical which can be completely saturated, partly unsaturated or completely unsaturated and which can be interrupted by at least one or more identical or different, preferably one to three, atoms from the group consisting of nitrogen, sulfur or oxygen , but two oxygen atoms must not be directly adjacent and at least one carbon atom must be present in the ring, such as a residue of thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1, 3,4-oxadiazole, 1, 3,4-thiadiazole, 1, 3,4-triazole, 1, 2,4 -Oxadiazole, 1, 2,4-thiadiazole, 1, 2,4-triazole, 1, 2,3-triazole, 1,2,3,4-tetrazole, benzo [b] thiophene, benzo [b] furan, indole , Benzo [c
• Heterocyclyl particularly preferably means a saturated, partially saturated or aromatic ring system with 3 to 6 ring members and 1 to 4 heteroatoms from the group O, S and N, where at least one carbon atom must be present in the ring.
• Heterocyclyl very particularly preferably denotes a radical of pyridine, pyrimidine, (1, 2,4) -oxadiazole, (1, 3,4) -oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, Imidazole, pyrazole, isoxazole, 1, 2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane and oxetane.
• Aryloxy therefore means an aryl radical as defined above which is bonded via an oxygen atom, such as e.g. the phenoxy or naphthyloxy group.
• Arylthio means an aryl residue linked via a sulfur atom, e.g. the phenylthio or the 1- or 2-naphthy ⁇ thio radical.
• Arylamino means an aryl residue linked via a nitrogen atom, e.g. the anilino or the 1- or 2-naphthamino radical.
• N - ⁇ - C alkyl arylamino means the N-methyl or N-ethyl-anilino radical.
• Aryl- (C 1 -C 4 ) alkoxy stands for an aryl radical linked via a (C 1 -C 4 -alkoxy group), for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.
• Aryl- (C 3 -C 4 ) alkenyloxy stands for an aryl radical linked via a (C 3 -C 4 ) alkenyloxy group, for example the 1-, 2- or 3-phenylallyloxy radical.
• Aryl- (C 1 -C 4 ) alkylthio stands for an aryl radical which is linked via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the 1- or 2-phenylethylthio radical.
• Aryl- (C 3 -C 4 ) -alkenylthio stands for an aryl radical linked via a (C 3 -C 4 ) -alkenylthio group, for example the 1, 2- or 3-phenylallylthio radical.
• Aryl- (C 3 -C 4 ) alkenylamino stands for an aryl radical linked via a (C 3 -C 4 ) alkenylamino group, for example the 1-, 2- or 3-phenylallylamino radical.
• Aryl- (CC 8 ) -dialkylsilyl stands for. B. for a phenyl or naphthyldimethylsilyl group.
• Diaryl- (C 3 -C 4 ) alkylsilyl is e.g. B. for a diphenyl, phenyl-naphthyl, or dinaphthyl-methylsilyl group.
• Triarylsiiyl stands for example for a triphenyl, diphenyl-naphthyl or trinaphthylsilyl group.
• Haloalkyl e.g. the 1- or 2-fluoroethyl, the trifluoromethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl or the 1, 1, 2,2-tetrafluoroethyl group;
• Haloalkenyl e.g. the 1-, 2- or 3-fluoroalyl group or the 1, 1-difluoropropen-3-yl group;
• Haloalkoxy such as e.g. B. trifluoromethoxy or 2,2,2-trifluoroethoxy;
• Haloalkylthio e.g. trifluoromethylthio
• Haloalkylsulfinyl e.g. trifluoromethylsulphinyl
• Haloalkylsulfonyl e.g. trifluoromethylsulfonyl
• Halocyclopropyl such as. B. 1,1-difluorocycloprop-2-yl.
• the compounds of the general formula (I) have acidic or basic properties and can form salts. If the compounds of the general formula (I) carry, for example, groups such as hydroxyl, carboxy or other groups which induce acidic properties, these compounds can be reacted with bases to form salts.
• Suitable bases are, for example, hydroxides, carbonates, hydrogen carbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines with (G, -C 4 ) alkyl radicals and mono-, di - and trialkanolamines of (C 1 -C 4 -alkanols.
• the compounds of the general formula (I) carry, for example, groups such as amino, alkylamino or other groups which induce basic properties, these compounds can be reacted with acids to form salts.
• Suitable acids are, for example, mineral acids , such as hydrochloric, sulfuric and phosphoric acid, organic acids such as acetic acid or oxalic acid, and acidic salts such as NaHS0 4 and KHS0 4.
• mineral acids such as hydrochloric, sulfuric and phosphoric acid
• organic acids such as acetic acid or oxalic acid
• acidic salts such as NaHS0 4 and KHS0 4.
• the salts thus obtainable also have insecticidal, acaricidal and miticidal properties.
• the compounds of the general formula (I) can 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 diastereomers can be made by conventional methods, e.g. be separated into the isomers by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods.
• the compounds according to the invention are prepared by methods known per se from the literature, as are described in standard works on organic synthesis, for example Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart. The preparation takes place under reaction conditions which are known and suitable for the reactions mentioned. Use can also be made of variants which are known per se and are not mentioned here in detail.
• the starting materials can also be formed in situ, in such a way that they are not isolated from the reaction mixture, but instead are immediately reacted further to give the compounds of the formula (I).
• the present invention also relates to processes for the preparation of compounds of the general formula (I).
• R 1 , R 2 , R 3 , R 4 , R 5 , A, Y and n have the meanings given for the formula (I), the procedure is, for example, that a carboxylic acid of the formula (III)
• X, R 2 , R 3 and n have the meanings given above for formula (I), in the form of an activated derivative of this acid, for example an acid halide, ester or anhydride, in the presence of a base, for example at least an amine, such as triethylamine, diisopropylethylamine, pyridine or lutidine, alkali metal carbonate, alkali metal hydrogen carbonate or alkali metal hydroxide or combinations of these compounds, with a compound of the formula (IV), in which R 4 and R 5 have the meanings given above for the formula (I),
• HNR 4 R 5 (IV) is implemented and, if appropriate, the residue R 5 is then further derivatized.
• Collections of compounds of 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 as described, for example, by SH DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", Volume 1, Escom 1997, pages 69 to 77.
• a number of commercially available devices can be used for the parallel reaction and processing, for example from the companies Stern Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H + P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleissheim, Germany or the company Radleys, Shirehill, Saffron Waiden, Essex, England.
• Chromatography apparatus for example from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA, is available for the parallelized purification of compounds of the general formula (I) or of intermediate products obtained in the preparation.
• the present invention also relates to libraries which contain at least two compounds of the formula (I).
• the compounds of formula (I) are suitable with good plant tolerance and favorable warm-blood toxicity for combating animal pests, in particular insects, arachnids, helminths and molluscs, very particularly preferably for combating insects and arachnids which are used in agriculture, in animal breeding, in Forests, in the protection of stocks and materials and in the hygiene sector. They are normally sensitive and resistant Species as well as all or individual stages of development are effective.
• the pests mentioned above include:
• Acarina e.g. Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Chorioptes spp ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp. From the order of the Isopoda e.g. Oniscus aselus, Armadium vulgäre, Porcellio s
• Thysanura e.g. Lepisma saccharina.
• Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phoralonosiphumus, spp.
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phoralonosiphumus,
• Nephotettix cincticeps Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp ..
• 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.
• 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 ..
• Protozoa such as Eimeria can also be controlled.
• the plant-parasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root-gall nematodes, such as Meloidogyne) incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii) as well as the genera Radopholus such as Radopholus similis, Pratylenchus such as Pratyuschuschanschatus, and Pratychus penetratus;
• the genera Radopholus such as Radopholus similis, Pratylenchus such as Pratyuschuschanschatus, and Pratych
• 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 Trususususususinusususus longusus x longus, such as Longus x.
• 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, for example crop protection agents, preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluscicidal or fungicidal, particularly preferably insecticidal and acaricidal compositions which contain one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
• crop protection agents preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluscicidal or fungicidal, particularly preferably insecticidal and acaricidal compositions which contain one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
• the active ingredient and the other additives are combined and brought into a suitable form of use.
• the invention also relates to compositions, in particular insecticidal and acaricidal compositions, which contain the compounds of the formula (!) 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). They can be formulated in different ways depending on how it is specified by the biological and / or chemical-physical parameters. Possible formulation options include:
• 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 i.e. Carrier and / or surface-active substances, such as inert materials, surfactants, solvents and other additives, are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J .; H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiiey & Sons, N.Y .; Marsden, “Solvent Guide,” 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual", MC Publ.
• Carrier and / or surface-active substances such as inert materials, surfactants, solvents and other additives
• combinations with other pesticidally active substances, fertilizers and / or growth regulators can also be produced, for example in the form of a finished formulation or as a tank mix.
• wettable powders preparations which are uniformly dispersible in water and which, in addition to the active substance, contain a diluent or an inert substance and also wetting agents, for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, for example sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6 ' - contain sodium disulfonic acid.
• 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, sorbitan acid ester fatty acid sorbitol polyesters, polyoxyethylene esters or polyoxyethylene sorbitates or polyoxyethylene sorbitates
• 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 as a mixture with fertilizers.
• the active substance concentration in wettable powders is usually about 10 to 90% by weight, the remainder to 100% by weight consists of customary 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% by weight % 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 required application rate varies. It can fluctuate within wide limits, e.g. between 0.0005 and 10.0 kg / ha or more of active substance, but it is preferably between 0.001 and 5 kg / ha of active substance.
• 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 and substances produced by microorganisms.
• Preferred mix partners are: 1. from the group of phosphorus compounds
• Alanycarb (OK-135), Aldicarb, 2-sec-ButylphenyImethylcarbamate (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;
• Methyl) ester (Ro12-0470), cyromazine, CM-002X, DBI-3204, diacloden ( Thiamethoxam), diafenthiuron, N- (3,5-dichloro-4- (1, 1, 2,3,3,3-hexafluo-propyloxy) phenyl) -carbamoyl) -2-chlorobenzcarboximidic acid ethyl ester, DDT, dicofol, diflubenzuron , N- (2,3-dihydro-3-methyl-1,3-thiazol-2-ylidenes) -2,4-xylidines, dinobutone, dinocap, diofenolan, DPX-062, emamectin benzoates (MK-244), Endosulfan, Ethiprole (Sulfethiprole), Ethofenprox, Etoxazole (YI-5301), Fenazaquin, F
• fungicides which can be combined with the compounds of the formula (I) according to the invention are, for example to name the following products:
• 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 invention therefore relates to the use of compounds of the formula (I) and their salts for controlling harmful organisms.
• the invention furthermore relates to a method for controlling harmful insects, arachnids and / or nematodes, in which a effective amount of a compound of formula (I) or its salts applied to the pests or the location of the desired effect.
• the active compounds according to the invention are also suitable for controlling endoparasites and ectoparasites in the human and veterinary medicine 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 powdering and by parenteral use in the form of, for example, injection.
• the invention therefore also relates to the use of a compound of the formula (I) or one of its salts for producing a human and / or veterinary medicinal product, preferably a veterinary medicinal product, in particular for controlling ectoparasites and / or endoparasites.
• the compounds of the formula (I) according to the invention can accordingly also be used particularly advantageously for the treatment of warm-blooded animals, in particular in animal husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese, etc.).
• animal husbandry for example cattle, sheep, pigs and poultry such as chickens, geese, etc.
• the compounds if appropriate in suitable formulations and if appropriate with the drinking water or feed, are administered to the animals 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 compounds can be used in cattle, for example, in doses of 0.01 to 1 mg / kg of body weight.
• the compounds of the formula (I) or their salts are also notable for a pronounced repellent effect.
• Repellent in the sense of the description is a substance or mixture of substances that has a defensive or expelling effect on other living beings, in particular pests and nuisances.
• the term also encompasses effects such as the antifeeding effect, in which food intake is disturbed or prevented (anti-fretting effect), suppression of egg laying or influencing population development.
• the invention therefore also relates to the use of compounds of the formula (I) or their salts to achieve the abovementioned effects, in particular in the pests mentioned in the biological examples.
• the invention also relates to a method for repelling or expelling harmful organisms, one or more compounds of the formula (I) or their salts being applied at the location from which the harmful organisms are to be kept or distributed.
• application can mean, for example, treatment of the plant or of the seed.
• the compounds of the formula (I) or their salts are notable for the fact that, if one wishes to take advantage of the effects mentioned above, the agent is applied at an earlier point in time than is customary in the case of direct control. The Effect often lasts for a long time, so that a duration of action of more than 2 months is achieved.
• the active compounds of the formula (I) according to the invention have an outstanding systemic action.
• the active ingredients can therefore also be introduced into the plants via parts of plants, both underground and above ground (roots, stems, leaves), if the active ingredients are applied in liquid or solid form to the immediate vicinity of the plant (e.g. granules in the soil application, application in flooded rice fields).
• the active compounds according to the invention can be used in a special way for the treatment of vegetative and generative propagation material, such as e.g. of seeds of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamental plants, of onions, cuttings and tubers of other vegetatively propagated crops and ornamental plants.
• vegetative and generative propagation material such as e.g. of seeds of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamental plants, of onions, cuttings and tubers of other vegetatively propagated crops and ornamental plants.
• the treatment for this can take place before the sowing or planting process (e.g. by special techniques of seed coating, by dressing in liquid or solid form or seed box treatment), during the sowing process or planting or after the sowing or planting process by special application techniques (eg seed row treatment).
• the amount of active ingredient used can vary over a wide range depending on the application. In general, the application rates are between 1 g and 10 kg of active ingredient per
• the compounds of formula (I) can also be used to control animal pests in crops of known or still to be developed genetically modified plants.
• the transgenic plants are usually distinguished by special advantageous properties, for example by resistance to certain crop protection agents, resistance to Plant diseases or pathogens of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses.
• Other special properties relate, for example, to 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
• crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables e.g. of cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or else 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.
• the use of the compounds according to the invention includes any other application in which compounds of the formula (I) act on the pests.
• Such indirect applications can be, for example, the use of compounds which, for example in the soil, the plant or the pest, decompose or break down to give compounds of the formula (I).
• 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 ingredient, 65 parts by weight of kaolin-containing quartz as 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 sodium lignosulfonic acid 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 cyclohexanone 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.
• compounds are considered to be active if they have an effect on the harmful organisms of 50% or more at a concentration of 500 ppm (based on the content of active ingredient) or less.
• Germinated field bean seeds Vicia faba
• germ roots were transferred to amber glass bottles filled with tap water and then coated with about 100 black bean aphids (Aphis fabae). Plants and aphids were then immersed in an aqueous solution of the compound 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 mortality of the compound on the aphids was determined.
• Germinated field bean seeds Vicia faba
• germ roots were transferred to amber glass bottles filled with tap water.
• Four milliliters of an aqueous solution of the compound to be tested and formulated were pipetted into the amber glass bottle.
• the broad bean was heavily coated with about 100 black bean aphids (Aphis fabae).
• the plant and aphids were then stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 3 and 6 days of storage, the root systemic activity of the compound was determined as aphid mortality.
• the compounds according to the following examples were active: 3, 8, 9, 10, 11, 12, 17, 18, 19, 21, -22 (ice), 22 (trans), 24, 30 (ice), 30 (trans), 31 (ice), 35, 124, 128, 134, 135, 161, 162, 163, 164, 165, 166, 203, 216, 219, 237 , 250, 353 and 356.
• Soybean plants each with three well-developed leaves, were sprayed to runoff point with an aqueous solution of the compound to be tested and formulated. After drying, a treated, an untreated and an infected with thrips of the species Frankliniella occidentalis were put together. The plants were stored in a climatic chamber (23 ° C, 50-60% relative humidity). After 14 days, leaf damage was determined in the treated and untreated plants. The degree of repellent effect resulted from the relative comparison of the leaf damage of the untreated plant (corresponds in each case to 100%) with that of the treated plant. The connection according to the following example was active in this repellent attempt: 19.

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• 2001
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• 2002
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