WO2002050035A2 - Dichloropyridylmethylamides - Google Patents

Dichloropyridylmethylamides Download PDF

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Publication number
WO2002050035A2
WO2002050035A2 PCT/EP2001/014573 EP0114573W WO0250035A2 WO 2002050035 A2 WO2002050035 A2 WO 2002050035A2 EP 0114573 W EP0114573 W EP 0114573W WO 0250035 A2 WO0250035 A2 WO 0250035A2
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
butyl
butoxy
propyl
tert
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PCT/EP2001/014573
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German (de)
English (en)
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WO2002050035A8 (fr
WO2002050035A3 (fr
Inventor
Ernst Rudolf F. Gesing
Gerd Hänssler
Karl-Heinz Kuck
Ulrike Wachendorff-Neumann
Christoph Erdelen
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Bayer Cropscience Ag
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Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to EP01991825A priority Critical patent/EP1345494A2/fr
Priority to JP2002551532A priority patent/JP2004524287A/ja
Priority to KR10-2003-7006897A priority patent/KR20030060952A/ko
Priority to AU2002231690A priority patent/AU2002231690A1/en
Publication of WO2002050035A2 publication Critical patent/WO2002050035A2/fr
Publication of WO2002050035A3 publication Critical patent/WO2002050035A3/fr
Publication of WO2002050035A8 publication Critical patent/WO2002050035A8/fr

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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
    • A01N43/34—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
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • 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
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • C07D213/61—Halogen atoms or nitro radicals

Definitions

  • the present invention relates to new dichloropyridylmethylamides, a process for their production and their use to combat undesirable ones
  • Microorganisms and animal pests are Microorganisms and animal pests.
  • R 1 represents hydrogen, alkyl, haloalkyl, optionally substituted heterocyclyl or optionally substituted heterocyclylalkyl and
  • R 2 represents alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aryloxyalkyl or for optionally substituted heterocyclylalkyl, found.
  • dichloropyridylmethylamides of the formula (I) can be prepared by using dichloropyridylmethylamines of the formula
  • R 1 has the meaning given above
  • R 2 has the meaning given above and
  • dichloropyridylmethylamides of the formula (I) according to the invention have a significantly better fungicidal and insecticidal action than the constitutionally most similar, known substances of the same action.
  • heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member has a hetero atom, i.e. is an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, these are not adjacent.
  • dichloropyridylmethylamides according to the invention are generally defined by the formula (I).
  • R 1 represents hydrogen, alkyl having 1 to 4 carbon atoms or haloalkyl
  • Carbon atoms or represents three- to six-membered heterocyclyl with 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, it being possible for these radicals to be monosubstituted to trisubstituted, identical or different, by halogen, Cyano, nitro, alkyl with 1 to 4 carbon atoms and / or alkoxy with 1 to 4 carbon atoms, or for heterocyclylalkyl with three to six ring members and 1 to 3 heteroatoms, such as oxygen, nitrogen and / or sulfur, in the heterocycle and 1 to 4 carbon atoms is in the alkyl part, where these radicals can be substituted once to three times, identically or differently by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, and
  • alkyl with 1 to 4 carbon atoms for alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkenyl with 2 to 6 carbon atoms or for cycloalkyl with 3 is up to 7 carbon atoms, where the cycloalkyl radicals can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4 carbon atoms, or aryl having 6 to 10 carbon atoms , where these radicals can be substituted one to three times, in the same way or differently, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to
  • R 1 for hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, sec.- or tert-
  • -Butoxy and / or tert-butoxy or represents phenoxyalkyl having 1 to 4 carbon atoms in the alkyl part, where these radicals can be substituted one to three times, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy and or tert.-
  • butoxy or stands for pyridyl, furyl, thienyl, oxetanyl or pyrimidyl, where these radicals can be substituted one to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n -Butyl, i-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy and or tert.-butoxy, or for Pyridylmethyl, furylmethyl, thienylmethyl, oxetanyl ethyl or pyrimidylmethyl, where these radicals can be substituted one to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, e
  • Formula (II) provides a general definition of the dichloropyridylmethylamines required as starting materials when carrying out the process according to the invention.
  • R 1 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • the Dichlo ⁇ yridylmethylamine of formula (II) are known or can be prepared by known methods (cf. Rec. Trav. Chim. Pays-Bas 52 (1933), 55-56).
  • Formula (III) provides a general definition of the halocarbonyl compounds required as starting materials when carrying out the process according to the invention.
  • R 2 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • X preferably represents chlorine.
  • halocarbonyl compounds of the formula (III) are known or can be prepared by known methods.
  • Suitable diluents for carrying out the process according to the invention are all customary inert, organic solvents.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether,
  • Dioxane tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide
  • Esters such as methyl acetate or ethyl acetate. Mixtures of the aforementioned can also be used
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or Sodium bicarbonate, also ammonium compounds, such as ammonium acetate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylamline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmo ⁇ holin, N, N-Di - methylaminopyridine, diazabicyclooctane (DAB)
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 120 ° C, preferably between 0 ° C and 80 ° C.
  • the process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure, e.g. at pressures between 0.1 bar and 10 bar.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and
  • Bacteria can be used in crop protection and material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • pathogens of fungal and bacterial are exemplary but not limiting
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans; Erwinia species, such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae
  • Pellicularia species such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; Pseudocercosporella species, such as, for example, Pseudocercosporella he ⁇ otrichoides.
  • Plants on. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as those substances which are able to stimulate the immune system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
  • undesirable microorganisms include phytopathogenic
  • the substances according to the invention can therefore be used to protect plants against attack by the named pathogens within a certain period of time after the treatment.
  • the period of time within which protection is provided generally ranges from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the
  • the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • the active compounds according to the invention can be used with particularly good success in combating cereal diseases, for example against Erysiphe species.
  • the active compounds according to the invention are also suitable for increasing the crop yield.
  • the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and products for the synthesis of further active ingredients.
  • the active substances are suitable for controlling animal pests, especially insects,
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Diplopoda e.g. Blaniulus guttulatus.
  • Chilopoda e.g. Geophilus ca ⁇ ophagus, Scutigera spp ..
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera for example Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • the Blattaria for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
  • the Dermaptera for example, Forficula auricularia.
  • From the order of the Isoptera for example Reticuliterm.es spp ..
  • Phthiraptera From the order of the Phthiraptera, for example Pediculus humanus co ⁇ oris, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phros
  • Anthonomus spp. Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meliginusus seneus.
  • Gibbium psylloides Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala,
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention adhesives, glues, paper and cardboard, textiles, leather, wood, paints and
  • Plastic items, cooling lubricants and other materials that are organisms can be attacked or decomposed.
  • parts of production plants, for example cooling water circuits are also mentioned which can be impaired by the multiplication of microorganisms.
  • the preferred technical materials are adhesives, glues, papers and cartons, leather, wood
  • Bacteria, fungi, yeasts, algae and, for example, are microorganisms which can cause degradation or a change in the technical materials
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucus organisms and algae.
  • microorganisms of the following genera may be mentioned:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma such as Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds can be converted into the customary formulations, such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm mist formulations.
  • customary formulations such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm mist formulations.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone
  • aliphatic hydrocarbons such as cyclohexane or paraffins
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and
  • Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates.
  • natural rock meals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • synthetic rock meals such as highly disperse silica, aluminum oxide and silicates.
  • the following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite,
  • Possible emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are, for example, lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used as such or in their formulations, also in a mixture with known fungicides, bactericides, acaricides, nematicides or insect cides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Aldimo ⁇ h ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (TBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione, Iprovalicarb,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,
  • Thicyofen Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,
  • Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin,
  • Insecticides / acaricides / nematicides Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb,
  • Mecarbam Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
  • Tefluthrin Tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensine, tralocythrin, tralomate-zeniazin
  • the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and shoot fungi, mold and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillichophystonus fumigatus fumigatus such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi in no way represents a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • Application takes place in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to apply the active ingredient preparation or the active ingredient itself to the soil to inject.
  • the seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • Active ingredient characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates.
  • the agents used to protect industrial materials generally contain the active substances in an amount between 5 and 95% by weight, preferably between
  • the application concentrations of the active substances according to the invention depend on the type and occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimal amount can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
  • the effectiveness and the spectrum of action of the active ingredients to be used according to the invention in the material protection or of the agents, concentrates or formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active ingredients are used to increase the Spectrum of effects or achieving special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
  • plants and their parts can be treated according to the invention.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • the treatment according to the invention can also result in superadditive (“synergistic”) effects.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, contain genetic material which gives these plants particularly advantageous properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting,
  • transgenic plants Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • Bt plants As traits, special features are raised the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Bt plants As properties
  • Traits are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT” gene).
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Examples of “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • Examples of herbicide-tolerant plants are maize, cotton and
  • Soybean varieties named under the trade names Roundup Ready® tolerance to glyphosate e.g. corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, e.g. rapeseed
  • IMI® tolerance to imidazolinones
  • STS® tolerance to sulfonylureas e.g. corn ) to be expelled.
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants.
  • Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the preparation and use of substances according to the invention are illustrated by the following examples.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and with larvae of the horseradish beetle
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella xylostella) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Solvent 31 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentrations with water containing emulsifier.
  • Broad bean seedlings (Vicia faba), which are infested with the green peach aphid (Myzus persicae), are immersed in a preparation of active compound of the desired concentration and placed in a plastic can.
  • the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • Solvent 50 parts by weight of N, N-dimethylformamide emulsifier: 1.2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted to the desired concentration with water and the stated amount of emulsifier.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Abstract

L'invention concerne de nouveaux dichloropyridylméthylamides de formule (I) dans laquelle R1 désigne hydrogène, alkyle, halogénure d'alkyle, hétérocyclyle éventuellement substitué ou hétérocyclylalkyle éventuellement substitué et R2 désigne alkyle, halogénure d'alkyle, alcoxyalkyle, alkényle, cycloalkyle éventuellement substitué, hétérocyclyle éventuellement substitué, aryle éventuellement substitué, aralkyle éventuellement substitué, aryloxyalkyle éventuellement substitué ou hétérocyclylalkyle éventuellement substitué. L'invention concerne un procédé permettant de produire lesdites nouvelles substances et leur utilisation pour lutter contre des micro-organismes indésirables et des parasites animaux.
PCT/EP2001/014573 2000-12-20 2001-12-12 Dichloropyridylmethylamides WO2002050035A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP01991825A EP1345494A2 (fr) 2000-12-20 2001-12-12 Dichloropyridylmethylamides
JP2002551532A JP2004524287A (ja) 2000-12-20 2001-12-12 ジクロロピリジルメチルアミド類
KR10-2003-7006897A KR20030060952A (ko) 2000-12-20 2001-12-12 식물 보호제로서 사용되는 살충성 및 살진균성(2,6-디클로로-4-피리딜) 메틸카바메이트
AU2002231690A AU2002231690A1 (en) 2000-12-20 2001-12-12 Insecticidal and fungicidal (2,6-dichloro-4-pyridyl) methylcarbamates used as plant protective agents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10063486.9 2000-12-20
DE10063486A DE10063486A1 (de) 2000-12-20 2000-12-20 Dichlorpyridylmethylamide

Publications (3)

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WO2002050035A2 true WO2002050035A2 (fr) 2002-06-27
WO2002050035A3 WO2002050035A3 (fr) 2003-04-10
WO2002050035A8 WO2002050035A8 (fr) 2003-06-12

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EP (1) EP1345494A2 (fr)
JP (1) JP2004524287A (fr)
KR (1) KR20030060952A (fr)
AU (1) AU2002231690A1 (fr)
DE (1) DE10063486A1 (fr)
WO (1) WO2002050035A2 (fr)

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JP2006016355A (ja) * 2004-07-02 2006-01-19 Kureha Corp Ｎ−（置換または無置換）シクロアルキル−２，６−ジクロロ−４−ピリジルメチルアミン誘導体及び農園芸用病害防除剤。
WO2012029672A1 (fr) 2010-08-31 2012-03-08 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre des organismes nuisibles

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EP0334812A2 (fr) * 1988-03-25 1989-09-27 Ciba-Geigy Ag Agents pour la protection de plants contre des maladies
EP1016661A1 (fr) * 1997-09-10 2000-07-05 Dainippon Ink And Chemicals, Inc. Derives de 2,6-dichloro-4-pyridinemethanol et produits chimiques utilises en agriculture
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JP2006016355A (ja) * 2004-07-02 2006-01-19 Kureha Corp Ｎ−（置換または無置換）シクロアルキル−２，６−ジクロロ−４−ピリジルメチルアミン誘導体及び農園芸用病害防除剤。
WO2012029672A1 (fr) 2010-08-31 2012-03-08 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre des organismes nuisibles
CN102892290A (zh) * 2010-08-31 2013-01-23 明治制果药业株式会社 有害生物防除剂
EP2628389A1 (fr) * 2010-08-31 2013-08-21 Meiji Seika Pharma Co., Ltd. Agent de lutte contre des organismes nuisibles
EP2631235A2 (fr) 2010-08-31 2013-08-28 Meiji Seika Pharma Co., Ltd. Agents de contrôle de nuisibles
EP2628389A4 (fr) * 2010-08-31 2014-01-01 Meiji Seika Pharma Co Ltd Agent de lutte contre des organismes nuisibles
CN103960242A (zh) * 2010-08-31 2014-08-06 明治制果药业株式会社 有害生物防除剂
EP2789237A1 (fr) 2010-08-31 2014-10-15 Meiji Seika Pharma Co., Ltd. Agents de contrôle de nuisibles
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EP2959775A1 (fr) 2010-08-31 2015-12-30 Meiji Seika Pharma Co., Ltd. Agents de contrôle de nuisibles
AP3539A (en) * 2010-08-31 2016-01-13 Meiji Seika Pharma Co Ltd Pest control agent
EP2984930A1 (fr) 2010-08-31 2016-02-17 Meiji Seika Pharma Co., Ltd. Agents de contrôle de nuisibles
US9328068B2 (en) 2010-08-31 2016-05-03 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl) methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of animal parasitic pests and agricultural/horticultural pests
US9717242B2 (en) 2010-08-31 2017-08-01 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of agricultural/horticultural pests
US10085449B2 (en) 2010-08-31 2018-10-02 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2- trifluoroacetamide for control of agricultural/horticultural pests

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AU2002231690A1 (en) 2002-07-01
WO2002050035A8 (fr) 2003-06-12
WO2002050035A3 (fr) 2003-04-10
JP2004524287A (ja) 2004-08-12
EP1345494A2 (fr) 2003-09-24
DE10063486A1 (de) 2002-07-04
KR20030060952A (ko) 2003-07-16

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