EP1211940A1 - Composes azabicyclo et azacyclo oximes et amines utilises comme pesticides - Google Patents

Composes azabicyclo et azacyclo oximes et amines utilises comme pesticides

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Publication number
EP1211940A1
EP1211940A1 EP00962385A EP00962385A EP1211940A1 EP 1211940 A1 EP1211940 A1 EP 1211940A1 EP 00962385 A EP00962385 A EP 00962385A EP 00962385 A EP00962385 A EP 00962385A EP 1211940 A1 EP1211940 A1 EP 1211940A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
straight
spp
branched
formulae
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00962385A
Other languages
German (de)
English (en)
Inventor
Stephen Lindell
Ulrich Sanft
Maria-Theresia Thönessen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Aventis CropScience GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Aventis CropScience GmbH filed Critical Aventis CropScience GmbH
Priority to EP00962385A priority Critical patent/EP1211940A1/fr
Publication of EP1211940A1 publication Critical patent/EP1211940A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • 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
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C09D5/025—Preservatives, e.g. antimicrobial agents

Definitions

  • the invention relates to the field of pest control, especially the control of animal pests like arthropods, e.g. insects and arachnids, ecto- and endoparasites, helminths, nematodes and mollusks.
  • arthropods e.g. insects and arachnids, ecto- and endoparasites, helminths, nematodes and mollusks.
  • Carbamates of quinuclidinone 3-oximes are known as pesticides from FR-A 2 086 292 and carbamates of piperidine 4-oximes are known as pesticides from GB 1 ,244,483.
  • R 1 and R 2 are independently hydrogen or a straight or branched lower alkyl group having from 1 to 4 carbon atoms, which is optionally substituted by one or more fluorine atoms;
  • R 3 is hydrogen, a straight or branched lower alkyl group having from 1 to 6 carbon atoms, (C 3 -C 6 )-cycloalkyl, hydroxy, a straight or branched lower alkoxy group having from 1 to 4 carbon atoms, an acyloxy group, wherein the acyl moiety has from 2 to 5 carbon atoms, or -(CH 2 ) q NR 4 R 5 ; q is zero, one, two, three or four;
  • R 4 and R 5 are independently hydrogen or a straight or branched lower alkyl group having from 1 to 4 carbon atoms;
  • Y is a bond or a straight or branched hydrocarbon chain having from 1 to 20 carbon atoms and optionally containing one to three double and/or triple bonds;
  • Z is
  • R 6 , R 7 are independently hydrogen or a straight or branched alkyl group having from 1 to 4 carbon atoms;
  • R 8 is a straight or branched alkyl group having from 1 to 6 carbon atoms
  • R 9 is hydrogen, a straight or branched lower alkyl group having from 1 to 6 carbon atoms or benzyl;
  • R 10 is a straight or branched hydrocarbon having from 1 to 6 carbon atoms and optionally containing 1 or 2 double and/or triple bonds; with the proviso that compounds of formula (I) and (IV) wherein n or p is 2;
  • Z is C(O)NR 6 R 7 are excluded.
  • Illustrative examples of lower alkoxy groups having from 1 to 4 carbon atoms are methoxy, trifluoromethoxy, ethoxy and n-propoxy.
  • Illustrative examples of a saturated straight or branched hydrocarbon chain having from 1 to 8 carbon atoms include n-octyl, n-heptyl, and all the illustrative examples of straight or branched lower alkyl groups having from 1 to 6 carbon atoms set forth above.
  • Illustrative examples of straight or branched unsaturated hydrocarbon chains which contain from 1 to 3 unsaturations which are double or triple bonds are ethenyl, 2,4-pentadienyl, 1 ,4-pentadienyl, 2,4-pentadiynyl, 1 ,4-pentadiynyl, (E&Z)-2-penten- 4-ynyl, 2-pentyn-4-enyl, 2-propenyl, 3-butenyl, 1-methyl-2-propenyl, 2-pentenyl, 2-ethyl-3-butenyl, 4-hexenyl, ethynyl, 2-propynyI, l-methyl-2-propynyl, 1 -ethyl-2- propynyl, 1-methyl-3-butynyl, 3-butynyl, or 4-pentynyl.
  • Agrochemically acceptable acid addition salts of the compounds of Formulae (I), (II), (III) and (IV) are illustratively hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, benzoic, citric, malonic, salicylic, malic, fumaric, oxalic, succinic, tartaric, lactic, gluconic, ascorbic, maleic, asparatic, benzenesulfonic, methane- and ethanesulfonic, hydroxymethane- und hydroxyethanesulfonic.
  • Preferred compounds of the present invention are those of Formulae (I) and (III) with the compounds of Formula (I) being more preferred.
  • the most preferred compounds of this invention are those of Formula (I) wherein n is one, i.e., compounds of the following Formula (V):
  • Compounds of the present invention may exist in either of two Z and E isomeric forms.
  • the present invention includes both forms of the compounds as well as mixtures of the Z and E forms.
  • both the Z and E forms of the olefins are included in the present invention.
  • the compounds of Formulae (I), (III), and (IV) can be prepared by reacting a ketone of the following Formulae (IX), (X) and (XI) with an amine of the formula NH 2 OR*HCI wherein Y, Z and R 3 have the meanings defined in Formulas (I), (II), (III) and (IV) as depicted below:
  • the salts can be prepared by contacting the free base form of the compounds of the invention with a sufficient amount of the desired acid to produce the salt in the conventional manner.
  • the free base forms may be regenerated, if desired, by treating the salt form with a base.
  • dilute aqueous solutions of such bases as sodium hydroxide, potassium carbonate, ammonia, and sodium bicarbonate may be utilized for this purpose.
  • the free base forms of the compounds of this invention differ somewhat from their respective salt forms in such physical properties as melting point and solubility in polar solvents, but the salts are otherwise equivalent to their respective free acid or base forms for the use according to the invention.
  • the starting materials represented by Formulae (IX), (X) and (XI) are known in the art or can be prepared by procedures generally known in the art. See, for example, K. Nador et al., Arzneim. Forsch., 1962, 12, 305 and J.Sauders et al., J. Chem. Soc, Chem. Comm. 1988, 1618 and R.J. Snow and L.J. Street, Tet. Lett. 1989, 30, 5795 and L. J.
  • amines represented by NH 2 O-Y-Z are commercially available or may be prepared by procedures generally known in the art. See for example H. Tecle et al., J. Med. Chem., 1998, 41 , 2524.
  • Collections of compounds of the formulae (I) to (IV) which can be synthesized by the abovementioned schemes may also be prepared in a parallel manner, and this may be effected manually or in a semiautomated or fully automated manner.
  • this is to be understood as meaning a procedure as it is described, for example, by S.H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated synthesis", Volume 1 , Verlag Escom 1997, pages 69 to 77.
  • compounds of the formulae (I) to (IV) may be prepared in part or fully by solid-phase-supported methods.
  • individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin.
  • Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998.
  • the compounds of the Formulae (I) to (IV) are suitable for controlling animal pests, in particular arthropods, e.g. insects and arachnids, helminths, nematodes, ecto- and endoparasites and mollusks, especially for controlling insects and arachnids which are encountered in agriculture, in livestock breeding, in forests, in the protection of stored goods and materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or individual developmental stages.
  • arthropods e.g. insects and arachnids, helminths, nematodes, ecto- and endoparasites and mollusks
  • the abovementioned pests include: from the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,
  • Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp.
  • Chilopoda for example, Geophilus carpophagus, Scutigera spp.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura for example, Lepisma saccharina.
  • Orthoptera for example, Blatta orientalis, Periplanata americana, Leucophaea maderae, Blattella germanica, Arace domesticus,
  • Gryllotalpa spp. Locusta migratoria migratorioides, Melanoplus differentialis,
  • Thysanoptera for example, Hercinothrips femoralis, Thrips tabaci.
  • Homoptera for example, Aleurodes brassicae, Bemisia tabaci,
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Hymenoptera From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • helminths for example, Haemonchus, Trichostrongulus
  • Gastropoda for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp.
  • Bivalva for example, Dreissena spp.
  • the plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil-dwelling nematodes such as, for example, those of the genera Meloidogyne (root knot nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii) and of the genera Radopholus, such as Radopholus similis, Pratylenchus such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus;
  • the root-parasitic soil-dwelling nematodes such as, for example, those of the genera Meloidogyne (root knot nema
  • 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 longicaudatus, Longidorus such as Longidorus elongatus, Trichodorus such Trichodorus primitivus and Xiphinema such as Xiphinema index.
  • Ditylenchus stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor
  • Aphelenchoides foliar nematodes, such as Aphelenchoides ritzemabosi
  • Anguina seed nematodes, such as Anguina tritici
  • the invention also relates to compositions, for example crop protection compositions, preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluskicidal or helminthicidal, especially preferably insecticidal and acaricidal, compositions which comprise one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
  • crop protection compositions preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluskicidal or helminthicidal, especially preferably insecticidal and acaricidal, compositions which comprise one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
  • compositions according to the invention comprise 1 to 95% by weight of one or more active substances of the Formulae (I) to (IV).
  • compositions according to the invention To prepare the compositions according to the invention, the active substance and the other additives are combined and brought into suitable use form.
  • WP Wettable powders
  • EC emulsifiable concentrates
  • SC aqueous solutions
  • SC oil- or water-based dispersions
  • SE suspoemulsions
  • SE dusts
  • WG water- dispersible granules
  • ULV formulations, microcapsules, waxes or baits.
  • Wettable powders are preparations which are uniformly dispersible in water which, besides the active substance, also comprise wetters, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkylsulfonates or alkylphenolsulfonates and dispersants, for example sodium lignosulfonate or sodium 2,2'- dinaphthylmethane-6,6'-disulfonate, in addition to a diluent or inert material.
  • wetters for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkylsulfonates or alkylphenolsulfonates and dispersants, for example sodium lignosulfonate or sodium 2,2'- dinaphthylmethane-6,6'-disulfonate, in addition to a diluent or inert material.
  • Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers.
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons.
  • emulsifiers the following can be used, for example: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
  • calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid est
  • Dusts can be obtained, for example, by grinding the active substance with finely divided solid materials, for example talc or natural clays, such as kaolin, bentonite, pyrophyllite or diatomaceous earth.
  • Granules can be prepared either by atomizing the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of carrier materials such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or else mineral oils.
  • Suitable active substances can also be granulated in the manner which is customary for the preparation of fertilizer granules, if desired as a mixture with fertilizers.
  • the active substance concentration in wettable powders is, for example, approximately 10 to 90% by weight, the remainder to 100% by weight is composed of customary formulation auxiliaries.
  • the active substance concentration may be approximately 5 to 80% by weight.
  • Formulations in the form of dusts usually comprise 5 to 20% by weight of active substance, sprayable solutions approximately 2 to 20% by weight.
  • the active substance content depends partly on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers and the like are being used.
  • the abovementioned active substance formulations comprise, if appropriate, the tackifiers, wetters, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are conventional in each case.
  • the concentrates which are present in commercially available form, are, if desired, diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules using water. Preparations in the form of dusts and granules and sprayable solutions are usually not diluted any further with other inert substances prior to use.
  • the application rate required varies with the external conditions such as, inter alia, temperature and humidity. It may vary within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but it is preferably between 0.001 and 5 kg/ha.
  • the active substances according to the invention in their commercially available formulations and in the use forms prepared from these formulations (see the abovementioned compositions) may be present in mixtures with other active substances such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, molluskicides, growth regulatory substances or herbicides.
  • the pesticides include, for example, phosphoric esters, carbamates, carboxylic esters, formamidines, tin compounds and materials produced by microorganisms.
  • alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, HCN- 801 , isoprocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio(ethylideneamino)-N-methyl- N-(morpholinothio)carbamate (UC 51717), triazamate;
  • the active substance content of the use forms prepared from the commercially available formulations may range from 0.00000001 up to 95% by weight of active substance, preferably between 0.00001 and 1% by weight. Application is effected in a customary manner adapted to suit the use forms.
  • the invention also relates to a method of controlling animal pests, preferably harmful insects, Acarina, helminths, mollusks and/or nematodes in which an effective amount of one or more compounds of formulae (I) to (IV) or of a composition comprising of one or more compounds of formulae (I) to (IV) is applied to the animal pests or to the plants, areas or substrates infested with them.
  • the compounds of formulae (I) to (IV) are also suitable for use in the veterinary medicine sector, preferably for controlling endoparasites and ectoparasites, and in the field of animal keeping.
  • a compound of the formula (I) to (IV) in the preparation of a veterinary medicine, preferably for treating ecto- and endoparasites.
  • the active substances according to the invention may be applied in the known manner, such as by oral administration in the form of, for example, tablets, capsules, drinks or granules, by dermal application in the form of, for example, dipping, spraying, pouring on and spotting on, and dusting, and by parenteral administration in the form of, for example, an injection.
  • the compounds of formula (I) to (IV) are also suitable for use in technology, for example as wood preservative, as preservative in paints, in cooling lubricants for metalworking, or as preservative in drilling and cutting oils.
  • the compounds of formulae (I) to (IV) can also be employed particularly advantageously in livestock keeping (for example cattle, sheep, pigs and poultry such as chickens, geese and the like).
  • livestock keeping for example cattle, sheep, pigs and poultry such as chickens, geese and the like.
  • the compounds if appropriate in suitable formulations (cf. above), are administered orally to the animals, if appropriate together with the drinking water or feed. Since excretion in the feces is highly efficient, the development of insects in the animals' feces can be prevented very easily in this manner.
  • the dosages and formulations which are suitable in each case depend, in particular, on the species and the developmental stage of the productive livestock and also on the risk of infestation and can be determined readily and established by customary methods.
  • the compounds can be employed in cattle at dosages of 0.01 to 1 mg/kg bodyweight.
  • compositions according to the invention can be applied in combination with fungicides known from the literature.
  • fungicides known from the literature.
  • Such fungicides are described e.g. in C.D.S. Tomlin, S.B. Walker, The Pesticide Manual, 11 th ed., British Crop Protection Council, Farnham 1997.
  • the invention also relates to seed, treated or coated with an effective amount of one or more compounds of formulae (I) to (IV) or of a composition according to the invention.
  • the compounds of the formulae (I) to (IV) can also be employed for controlling harmful organisms in crops of known genetically engineered plants or genetically engineered plants yet to be developed.
  • the transgenic plants are distinguished by especially advantageous properties, for example by resistances to particular crop protection agents, resistances to plant diseases or pathogens of plant diseases, such as particular insects or microorganisms such as fungi, bacteria or viruses.
  • Other particular properties concern, for example, the harvested material with regard to quantity, quality, storage properties, composition and specific constituents.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and maize or else crops of sugar beet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and other types of vegetables.
  • the invention therefore also relates to the use of compounds of the formulae (I) to (IV) for controlling harmful organisms in transgenic crop plants.
  • the use according to the invention of compounds of the formula (I) or of compositions comprising them, for example as insecticide, acaricide, molluskicide, nematicide or helminthicide, also includes the case where the compound of the formula (I) or its salt is formed from a precursor only after application, for example in the insect, in a plant or in the soil.
  • Ph means phenyl
  • a dust is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as inert material and comminuting the mixture in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and
  • a dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium lignosulfonate and
  • An emulsifiable concentrate can be prepared from 15 parts by weight of active substance, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.
  • Granules can be prepared from 2 to 15 parts by weight of active substance and an inert granule carrier material such as attapulgite, pumice granules and/or quartz sand. It is expedient to use a suspension of the wettable powder of Example b) with a solids content of 30%, which is sprayed onto the surface of attapulgite granules, and these are dried and mixed intimately. The wettable powder amounts to approx. 5% by weight and the inert carrier material to approx. 95% by weight of the finished granules.
  • C. Biological examples such as attapulgite, pumice granules and/or quartz sand.
  • Bean plants Phaseolus vulgaris which were severely infested with a complete population of spider mites (Tetranychus urticae) were dipped into an aqueous solution of the formulated preparation to be tested. After 6 days storage in a controlled-environment cabinet at approx. 25 C C, the mortality of all mite stages was determined. At a concentration of 300 ppm (based on the active substance content) a 50 - 100 % mortality was caused by the preparations of examples 1 , 2, 4, 20, 28, 81 , 92, 117, 120, 141 and 142.
  • Filter paper sections containing approx. 30 24-hour-old eggs of the tobacco budworm (Heliothis virescens) were immersed for 5 seconds into an aqueous solution of the formulated preparation to be tested and subsequently placed in the Petri dish.
  • a further 200 ⁇ l of the aqueous solution were distributed over the nutrient medium.
  • the mortality of the preparation on the eggs and any larvae hatched from them was determined. At a concentration of 300 ppm a 50 - 100 % mortality was shown by the preparations of example 2.
  • the leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, the rice plants are placed in a Petri dish and populated with approximately 20 larvae (L3 stage) of the rice leaf hopper species Nilaparvata lugens. After 6 days' storage at approx. 25°C, the mortality among the leaf hopper larvae is determined. At a concentration of 300 ppm a 50 - 100 % mortality was shown by the preparations of examples 2 and 28.
  • Germinated broad bean seeds (Vicia faba) with radicles are transferred into brown glass bottles filled with tap water. Four milliliters of an aqueous solution of the formulated preparation to be examined are pipetted into the brown glass bottle. The broad bean is subsequently heavily populated with approximately 100 black bean aphids (Aphis fabae). After 6 days' storage at approx. 25°C, the root-systemic activity of the preparation on the aphids is determined. At a concentration of of 30 ppm a mortality of 50-100% among the aphids by root-systemic action was shown by the preparation of examples 2, 81 and 144.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Dispersion Chemistry (AREA)
  • Materials Engineering (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

L'invention concerne l'utilisation de composés azabicyclo et azacyclo oximes et amines de formule (I) à (IV), les symboles et les indices étant tels que définis dans les spécifications, composés destinés à éliminer les parasites des animaux.
EP00962385A 1999-08-27 2000-08-25 Composes azabicyclo et azacyclo oximes et amines utilises comme pesticides Withdrawn EP1211940A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP00962385A EP1211940A1 (fr) 1999-08-27 2000-08-25 Composes azabicyclo et azacyclo oximes et amines utilises comme pesticides

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP99116945 1999-08-27
EP99116945 1999-08-27
PCT/EP2000/008310 WO2001015532A1 (fr) 1999-08-27 2000-08-25 Composes azabicyclo et azacyclo oximes et amines utilises comme pesticides
EP00962385A EP1211940A1 (fr) 1999-08-27 2000-08-25 Composes azabicyclo et azacyclo oximes et amines utilises comme pesticides

Publications (1)

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EP1211940A1 true EP1211940A1 (fr) 2002-06-12

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EP00962385A Withdrawn EP1211940A1 (fr) 1999-08-27 2000-08-25 Composes azabicyclo et azacyclo oximes et amines utilises comme pesticides

Country Status (7)

Country Link
EP (1) EP1211940A1 (fr)
JP (1) JP2003508412A (fr)
KR (1) KR20020029115A (fr)
CN (1) CN1370048A (fr)
AU (1) AU7413500A (fr)
BR (1) BR0013541A (fr)
WO (1) WO2001015532A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1236727A1 (fr) * 2001-03-01 2002-09-04 Bayer CropScience GmbH Composés azabicylco comme pesticides
EP1692939A1 (fr) * 2005-02-19 2006-08-23 Bayer CropScience S.A. Pipéridines substituées pesticides
CN105294674B (zh) * 2014-07-29 2018-01-02 华东理工大学 氮杂双环衍生物及其制备和应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1244483A (en) * 1967-12-04 1971-09-02 Ici Ltd Carbamoyl piperidoneoximes and pesticidal compositions containing them
DE2019536A1 (de) * 1970-04-23 1971-11-11 Basf Ag Oximcarbamate
IL97266A0 (en) * 1990-03-06 1992-05-25 Warner Lambert Co Azabicyclo and azacyclo oximes and amines,their preparation and pharmaceutical compositions containing them

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0115532A1 *

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Publication number Publication date
BR0013541A (pt) 2002-05-14
WO2001015532A1 (fr) 2001-03-08
JP2003508412A (ja) 2003-03-04
CN1370048A (zh) 2002-09-18
KR20020029115A (ko) 2002-04-17
AU7413500A (en) 2001-03-26

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