EP1044188A1 - Derives de 4-aminopyridine acyles utilises comme pesticides et fongicides - Google Patents

Derives de 4-aminopyridine acyles utilises comme pesticides et fongicides

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Publication number
EP1044188A1
EP1044188A1 EP98954472A EP98954472A EP1044188A1 EP 1044188 A1 EP1044188 A1 EP 1044188A1 EP 98954472 A EP98954472 A EP 98954472A EP 98954472 A EP98954472 A EP 98954472A EP 1044188 A1 EP1044188 A1 EP 1044188A1
Authority
EP
European Patent Office
Prior art keywords
spp
alkyl
formula
alkoxy
compounds
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Withdrawn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
EP98954472A
Other languages
German (de)
English (en)
Inventor
Thomas Bretschneider
Markus Heil
Bernd Alig
Gerd Kleefeld
Christoph Erdelen
Andreas Turberg
Norbert Mencke
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 AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1044188A1 publication Critical patent/EP1044188A1/fr
Withdrawn legal-status Critical Current

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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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • A01N47/18—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, directly attached to a heterocyclic or cycloaliphatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present application relates to new acylated 4-aminopyridine derivatives, processes for their preparation and their use in combating animal pests and as fungicides.
  • R 1 represents alkyl, haloalkyl, alkoxy, alkylthio, alkoxyalkyl, alkylthioalkyl or optionally substituted cycloalkyl,
  • R 2 represents hydrogen, alkyl, alkoxy, halogen, cyano, aminothiocarbonyl or optionally substituted aryl,
  • R 3 represents alkyl, alkenyl, optionally substituted cycloalkyl or for optionally substituted aryl or arylalkyl
  • R 5 to R 12 independently of one another represent hydrogen or alkyl
  • A represents CH, CX 2 or N,
  • X 1 and X 2 independently of one another represent halogen, alkyl, alkoxy or haloalkyl and
  • n 0, 1, 2, 3 or 4
  • the new compounds of the formula (I) have highly pronounced biological properties and above all as fungicides and for combating animal pests, in particular insects, arachnids and ⁇ ematodes, which are used in agriculture, in the forests, in the stockpile. and material protection as well as in the hygiene sector are suitable
  • acylated 4-aminopyridines according to the invention show a considerably better activity against animal pests than known Neritatien similar in constitution
  • the Neritatien invention are generally defined by the formula (I)
  • R 1 preferably represents C r C 4 alkyl, C r C 4 alkoxy, C 1 -C 4 alkylthio, C r C -
  • R 2 preferably represents hydrogen, C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy, chlorine, bromine, cyano, aminothiocarbonyl or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, with halogen, C j - C 4 as substituents - Alkyl, -C-alkoxy and -C-C 4 haloalkyl with 1 to 5 identical or different halogen atoms come into question
  • R 3 is preferably C ⁇ -C alkyl, C 2 -C 4 alkenyl, which is optionally monosubstituted to trisubstituted by identical or different C j -C 4 alkyl or halogen substi- tuiert C 5 -C6 cycloalkyl or for phenyl or benzyl which is optionally monosubstituted to trisubstituted identically or differently, the substituents being halogen, Cj- alkyl, C r C 4 -alkoxy and C 1 -C 4 -haloalkyl having 1 to 5 identical or different halogen atoms come into question
  • R 5 to R independently represent hydrogen or C j -C 4 alkyl 12
  • R 4 also preferably represents an optionally mono- or disubstituted by identical or different substituents from halogen, C ⁇ -C 4 - alkyl, C ⁇ - alkoxy, or C 1 -C 4 -
  • Haloalkyl with 1 to 5 identical or different halogen atoms substituted 5- or 6-membered, saturated or unsaturated heterocycle with oxygen and / or sulfur and / or nitrogen as heteroatoms for example 1,2,4-oxadiazol-3-yl, 1,3 -Th ⁇ azol-2-yl or l, 4,2-D ⁇ oxazin-3-yl
  • A preferably represents CH or N.
  • A also preferably represents CX 2
  • X 1 and X 2 independently of one another preferably represent fluorine, chlorine, bromine,
  • n and n independently of one another are preferably 0, 1 or 2
  • Halogen stands for example for fluorine (atoms), chlorine (atoms) or bromine (atoms)
  • R 1 particularly preferably represents methyl, ethyl, methoxy, methylthio, 1-chloro-eth-1-yl, methoxymethyl or methylthiomethyl
  • R 2 particularly preferably represents hydrogen, methyl, methoxy, chlorine, bromine, cyano, aminothiocarbonyl or phenyl
  • R 3 particularly preferably represents methyl, ethyl, i-propyl, allyl, cyclohexyl, phenyl or benzyl
  • R 4 particularly preferably represents one of the radicals -CO-NH 2 , -CO-NHCH 3 ,
  • R 4 also particularly preferably represents 1, 2,4-oxadiazol-3-yl, 1, 3-thiazol-2-yl which is optionally substituted once or twice, identically or differently by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl or l, 4,2-dioxazin-3-yl
  • X 1 and X 2 independently of one another are particularly preferably fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl
  • n particularly preferably stands for 0
  • n particularly preferably represents 0 or 1
  • Preferred compounds according to the invention are substances of the formulas (IA), (IB), (IC) and (ID)
  • R 1 to R 4 , X 1 , X 2 , m and n represent the general, preferred and particularly preferred meanings mentioned above
  • Preferred compounds according to the invention are also substances of the formulas (IA-1), (IB-1), (IC-1) and (ID-1):
  • R 1 to R 4 represent the general, preferred and particularly preferred meanings mentioned above.
  • the general definitions or explanations of residues or explanations given above or in preferred areas apply accordingly to the end products and for the starting and intermediate products. These residual definitions can be combined with one another as desired, that is to say also between the respective preferred areas
  • hydrocarbon radicals such as alkyl or alkenyl - also in connection with heteroatoms such as alkoxy or alkylthio - are in each case straight-chain or branched as far as possible
  • N- (3-chloro-2-ethyl-pyrid ⁇ n-4-yl) -N-isopropoxycarbonyl-4- (4-cyanophenoxy) phenylacetic acid amide is used as the starting material and diphenyldithiophosphinic acid is used as the derivatization (sulfurization) reagent, it can be used the course of the process according to the invention can be reproduced by the following reaction scheme
  • R 1 to R 4 , A, X 1 , X 2 , m and n have the meanings given above and
  • X represents a leaving group, for example halogen, in particular chlorine or bromine
  • R is C 1 -C 4 alkyl, preferably methyl, ethyl, n- or i-propyl and
  • Y and Z for example, halogen, C ⁇ -C 4 alkyl, C j -C - alkoxy or C ⁇ -C 4 - halogenoalkyl having 1 to 5 identical or different halogen atoms, particularly preferably represents fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl stand
  • Aromatic nitriles (VI) can be converted, for example, into the carboxylic acid amides (VII) by hydrolysis (cf. for example JACS 78, 5416 (1956) and 79, 2530 (1957))
  • the 1,2,4-oxadiazoles (XI) are obtained by reaction of the aromatic nitriles (VI) with hydroxylamine to give the compounds (X) and subsequent ring closure with corresponding orthoesters
  • the pyridine-N-oxides and salts of the ner compounds of the formula (I) protonated on the pyridine nitrogen can be obtained in a generally customary and known manner, for example by the Neritatien of formula (I) with an oxidizing agent such as m-chloroperbenzoic acid or with organic or inorganic acids such as Trifluoroacetic acid, hydrogen bromide or hydrogen chloride.
  • an oxidizing agent such as m-chloroperbenzoic acid
  • organic or inorganic acids such as Trifluoroacetic acid, hydrogen bromide or hydrogen chloride.
  • the respective intermediate and end products are worked up and isolated in a generally known manner.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and ,ematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura for example Lepisma saccharina.
  • Collembola for example Onychiurus armatus
  • Orthoptera for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp,
  • Anoplura e.g. Pediculus humanus corporis, Haematopinus spp, Linognathus spp
  • Thysanoptera for example Hercinothrips femorahs, Th ⁇ ps tabaci
  • Heteroptera e.g. Eurygaster spp, Dysdercus lntermedius, Piesma quadrata, Cimex lectularius, Rhodmus pro xus, T ⁇ atoma spp
  • From the order of the Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundims, Phylloxera vastatrix, Phemphrosiphum spp humuh,
  • Rhopalosiphum padi Empoasca spp, Euscehs bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax st ⁇ atellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp, Psylla spp
  • Conoderus spp. Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Arachnida for example Scorpio maurus, Latrodectus mactans.
  • 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., Psoroptes Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp, Tetranychus spp ..
  • 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 ..
  • the compounds of the formula (I) according to the invention are notable in particular for high insecticidal and acaricidal activity
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents and / or solid
  • Carriers optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents
  • Aromatic solvents such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or are essentially suitable as liquid solvents Methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Solid carrier materials are suitable
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, synthetic rock powders such as highly disperse silica, aluminum oxide or silicates as solid
  • Carrier materials for granules are, for example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite or synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs or tobacco stalks, as emulsifying and / / or foam-generating 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, and dispersants include, for example, lignin sulfite - leach and methyl cellulose in question
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, or natural phospholipids, such as cephalins and lecithins or synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue or organic dyes such as alizine, 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% by weight of active compound, preferably between 0.5 and 90%
  • the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • Edifenphos epoxyconazole, ethirimol, etridiazole, Fenarimol, Fenbuconazole, Fen
  • Fen Positionam, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanyl, Fuberilafilil, Fuberri Furmecyclox,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Meth tartroxam, Metiram, Metsulfovax, Myclobutanil,
  • Pe Pe
  • azoate penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, Triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin, triticonazole,
  • Chlormephos Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,
  • Dichlofenthion dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathione, disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil,
  • Methamidophos Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
  • 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 by which the action of the active compounds is increased 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
  • the active substances according to the invention act not only against plant, hygiene and stored pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas
  • animal parasites ectoparasites
  • ectoparasites such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas
  • es include From the order of the Anoplurida, for example Haematopinus spp, Linognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp
  • Sternostoma spp Varroa spp From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp, Cheyletiella spp, Ornitrocheyletia spp, Myobia spp, Psorergates spp, Demodex spp, Trombicula spp, Listrophorus spp, Acarus spp, Tyrophlyusus spp, Caloglyphusus spp , Pterolichus spp, Psoroptes spp, Chorioptes spp, Otodectes spp., Sarcoptes spp, Notoedres spp, Knemidocoptes spp, Cytodites spp,
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are used for agricultural purposes, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese,
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes, Boh, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing , powdering and with the help of active ingredient-containing moldings, such as
  • the active compounds of the formula (I) can be formulated (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath O
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucihegus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccarina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
  • the one to be protected against insect attack is very particularly preferably
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing the same, are to be understood as examples: construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors , Plywood, chipboard, carpentry or wood products that are used in general in house construction or joinery
  • the active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and, if appropriate Dyes and pigments as well as other processing aids
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and the occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected
  • organic-chemical solvent or solvent mixture and / or an oily or oil-like difficultly volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents are preferably oily or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Suitable mineral oils or their aromatic fractions or solvent mixtures containing mineral oils are used as such low-volatility, water-insoluble, oily and oil-like solvents , preferably white spirit, petroleum and / or alkylbenzene.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C are advantageous.
  • Turpentine oil and the like are used
  • the organic slightly volatile oily or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture
  • part of the organic chemical solvent or solvent mixture is replaced by an aliphatic polar organic chemical solvent or solvent mixture.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups such as, for example, glycol ethers, esters or Like for application
  • the known organic-chemical binders are the water-thinnable and / or synthetic resins soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, eg polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as inden-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances of up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellents, odor agents and
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as organic-chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are used
  • binder mentioned can be replaced by a fixative (gem ⁇ sch) or a plasticizer (gem ⁇ sch). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. Preferably they replace 0.01 to 30% of the binder (based on to 100% of the binder used)
  • the plasticizers come from the chemical classes of phthalic acid esters such as
  • phosphoric acid esters such as T ⁇ butyl phosphate
  • adipic acid esters such as D ⁇ - (2-ethylhexyl) -ad ⁇ pat
  • stearates such as butyl stearate or Amyl stearate
  • oleates such as butyl oleate, glycerol ether or higher molecular weight glycol ether,
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumurone, and hexazazone, as well as fungonazole, as well as fungonazole, as well as fungonazole, as Azoles, cyproconazoles, metconazoles, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one or 4,5-dichloro-N-octylisothiazolin-3-one
  • the active compounds according to the invention also have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active ingredients are suitable for use as crop protection agents, in particular as fungicides. Fungicidal agents in crop protection are used to control Plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Bactericidal agents are used in crop protection to combat Pseudomonadaeae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • 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 Sportsiginea;
  • 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
  • Drechslera (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
  • Pelhcula ⁇ a species such as, for example, Pelhcula ⁇ a sasakn
  • Py ⁇ cula ⁇ a species such as, for example, Py ⁇ cula ⁇ a oryzae
  • Fusa ⁇ um species such as, for example, Fusa ⁇ um culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septo ⁇ a species such as, for example, Septo ⁇ a nodorum, Leptosphae ⁇ a species, such as, for example, Leptosphae ⁇ a nodorum, Cercospora species, such as, for example, Cercospora canescens, Alternaria species, such as, for example, Alterna ⁇ a brassicae, Pseudocercosporella species, such as, for example, Pseudocercosporella herpot ⁇ choides
  • the active compounds according to the invention can be used as such, in the form of their commercially available formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusting agents and granules. They are used in the customary manner, for example by Watering, spraying, spraying, scattering, foaming, brushing etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil. The seeds of the plants can also be used be treated
  • the active compound concentrations in the use forms can be varied within a substantial range and are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
  • 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 owl butterfly (Spodoptera exigua) while the leaves are still moist
  • the death rate is determined in%. 100% means that all the caterpillars have been killed, 0% means that none of the caterpillars have been killed

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux dérivés de 4-aminopyridine acylés de formule (I) dans laquelle R<1>, R<2>, R<3>, R<4>, A, X<1>, X<2>, m et n ont la signification indiquée dans la description. L'invention concerne également leur procédé de production ainsi que leur utilisation pour lutter contre les parasites animaux et comme fongicides.
EP98954472A 1997-11-14 1998-10-31 Derives de 4-aminopyridine acyles utilises comme pesticides et fongicides Withdrawn EP1044188A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19750403A DE19750403A1 (de) 1997-11-14 1997-11-14 Acylierte 4-Amino-pyridin-Derivate
DE19750403 1997-11-14
PCT/EP1998/006908 WO1999025691A1 (fr) 1997-11-14 1998-10-31 Derives de 4-aminopyridine acyles utilises comme pesticides et fongicides

Publications (1)

Publication Number Publication Date
EP1044188A1 true EP1044188A1 (fr) 2000-10-18

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ID=7848679

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98954472A Withdrawn EP1044188A1 (fr) 1997-11-14 1998-10-31 Derives de 4-aminopyridine acyles utilises comme pesticides et fongicides

Country Status (6)

Country Link
US (1) US6335325B1 (fr)
EP (1) EP1044188A1 (fr)
JP (1) JP2001523664A (fr)
AU (1) AU1157099A (fr)
DE (1) DE19750403A1 (fr)
WO (1) WO1999025691A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8236334B2 (en) * 2005-09-06 2012-08-07 Bass James S Composition and method for killing insects

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5399564A (en) 1991-09-03 1995-03-21 Dowelanco N-(4-pyridyl or 4-quinolinyl) arylacetamide and 4-(aralkoxy or aralkylamino) pyridine pesticides
TW306916B (fr) 1994-09-13 1997-06-01 Ciba Geigy Ag
DE4434637A1 (de) * 1994-09-28 1996-04-04 Hoechst Schering Agrevo Gmbh Substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide
TW334337B (en) 1994-11-07 1998-06-21 Novartis Ag Preparation and composition for a compound of controlling and preventing phytopathogenic fungi
ATE182585T1 (de) * 1995-04-28 1999-08-15 Kumiai Chemical Industry Co Pyridinderivative und pestizide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9925691A1 *

Also Published As

Publication number Publication date
AU1157099A (en) 1999-06-07
JP2001523664A (ja) 2001-11-27
DE19750403A1 (de) 1999-05-20
US6335325B1 (en) 2002-01-01
WO1999025691A1 (fr) 1999-05-27

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