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
  • A01N47/20—N-Aryl derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
  • C07D215/38—Nitrogen atoms
  • C07D215/42—Nitrogen atoms attached in position 4

Definitions

• the present application relates to new condensed pyridine derivatives, processes for their preparation and their use for controlling animal pests and as fungicides.
• R 1 and R 2 together with the carbon atoms to which they are attached represent an optionally substituted, mono- or polyunsaturated 5- or 6-membered ring,
• R 3 represents alkyl, alkenyl, optionally substituted cycloalkyl or in each case optionally substituted phenyl or benzyl
• R 4 represents optionally substituted phenyl or optionally substituted 2-pyridyl
• X represents alkyl, halogen, alkoxy or haloalkyl
• n 0, 1, 2, 3 or 4
• R 1 , R 2 , R 4 , X and n have the meaning given above,
• R 3 has the meaning given above and G represents a leaving group, for example halogen (especially chlorine or bromine) or imidazolyl;
• R 1 , R 2 and R 3 have the meaning given above,
• G, R 4 , X and n have the meaning given above, in the presence of a base and optionally in the presence of a diluent
• the condensed pyridine derivatives according to the invention show a considerably better activity against animal pests than known compounds of similar constitution
• R 1 and R 2 together with the carbon atoms to which they are attached preferably represent an optionally monosubstituted to trisubstituted, identically or differently, mono- or polyunsaturated 5- or 6-membered, in particular carboxyclic ring, preferably halogen as a substituent , -C -C 4 alkyl, C 1 -C 4 alkoxy, C ] -C 4 haloalkyl and C 1 -C 4 haloalkoxy, each with 1 to 5 identical or different halogen atoms
• R preferably represents C j -C 4 alkyl, C 2 -C 4 alkenyl, optionally optionally mono- to trisubstituted, identically or differently, C 5 -C (-cycloalkyl, or substituted by C j -C 4 alkyl or halogen in each case optionally mono- to three times by identical or different substituents, phenyl or benzyl, in each case as substituents preferably halo, Cj ⁇ -C alkyl, C j -C 4 alkoxy, and C j -C 4 haloalkyl and Cj-C 4 haloalkoxy, each with 1 to 5 identical or different halogen atoms
• R 4 preferably represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents, preference being given to substituents
• R 4 also preferably represents 2-py ⁇ dyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the preferred substituents being halogen, C j -C ⁇ alkyl, C j -C 4 alkoxy, C j -C 4 haloalkyl and C. ] -C 4 -
• Halogenoalkoxy having in each case 1 to 5 identical or different halogen atoms, C ⁇ -C 4 -Alkylth ⁇ o, C] -C 4 -Alkylsulf ⁇ nyl, C j -C - alkylsulfonyl, also C! -C 4 -Halogenalkylth ⁇ o, -C-C 4 -Halogenalkylsulf ⁇ nyl and -C-C 4 -Halogen- alkylsulfonyl, each with 1 to 5 identical or different halogen atoms, nitro, cyano and aminothiocarbonyl come into question
• X preferably represents fluorine, chlorine, bromine, C j -C 4 alkyl, CC ⁇ alkoxy or C j -
• n is preferably 0, 1 or 2
• Halogen (atoms) in the preferred radical definitions is, for example, fluorine (atoms), chlorine (atoms) and bromine (atoms)
• R 1 and R 2 together with the Py ⁇ din ⁇ ng to which they are bound, particularly preferably for the following ring systems 'which are optionally monosubstituted to trisubstituted, identically or differently, the substituents being fluorine, chlorine,
• R 3 particularly preferably represents methyl, ethyl, isopropyl, allyl, cyclohexyl,
• R 4 particularly preferably represents phenyl which is substituted once or twice, identically or differently, where fluorine, chlorine,
• R 4 also particularly preferably represents 2-pyridyl which is substituted once or twice, identically or differently, by chlorine, methyl and trifluoromethyl
• X particularly preferably represents fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl
• n particularly preferably represents 0 or 1
• 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.
• R 1 and R 2 have the meaning given above
• the 4-aminopyridines of the formula (VI) are known (cf., for example, J Praktician Chemie 154 (1988) and US Pat. No. 5,399,564) and / or can be obtained in an analogous manner
• the compounds of the formula (III) which are furthermore to be used as starting materials in process (a) according to the invention are generally known compounds of organic chemistry and / or can be obtained by generally known methods
• the compounds of the formula (IV) required as starting materials for carrying out process (b) according to the invention are new and are also the subject of the present application. They can be obtained in a manner known in principle (cf. WO 93/04580 and WO 96/33975) by man 4-Am ⁇ no-py ⁇ d ⁇ ne the
• the compounds of the formula (V) which are furthermore to be used as starting materials in process (b) according to the invention are generally known compounds of organic chemistry and / or can be obtained by generally known methods
• Halogenated aliphatic or aromatic hydrocarbons, ethers or nitols such as cyclohexane, toluene, chlorobenzene, choroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile are preferably usable
• Bases which can be used in processes (a) and (b) are all customary proton acceptors.
• Alkali or alkaline earth hydroxides, alkali or alkaline earth hydrides, alkali or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases can preferably be used, for example sodium hydroxide, calcium hydroxide, sodium hydride, potassium carbonate, sodium hydrogen carbonate, tethylamine, dibenzylamine, dnsopropylamine, py ⁇ din, chino n, diazabicyclooctane (DABCO),
• DABCO diazabicyclooctane
• Diazabicyclonones (DBN) and Diazabicycloundecen (DBU)
• DBN Diazabicyclonones
• DBU Diazabicycloundecen
• the reaction temperatures can be varied within a wide range in the processes (a) and (b) described. In general, temperatures between -40 ° C. and + 200 ° C., preferably between -10 ° C. and 100 ° C.
• the pyridm-N-oxides and salts of compounds of the formula (I) protomerized on the pyridine nitrogen can be obtained in a generally customary and known manner, for example by reacting the compounds of the formula (I) with an oxidizing agent such as, for example, Reacts chloroperbenzoic acid or reacts with organic or inorganic acids such as, for example, tetrafluoroacetic acid, hydrobromic acid or hydrochloric acid
• an oxidizing agent such as, for example, Reacts chloroperbenzoic acid or reacts with organic or inorganic acids such as, for example, tetrafluoroacetic acid, hydrobromic acid or hydrochloric acid
• the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector. They can preferably be used as crop protection agents They are effective against normally sensitive and resistant species and against all or individual stages of development.
• the pests mentioned above include
• Diplopoda for example, Blamulus guttulatus From the order of the Chilopoda, for example Geophilus carpophagus, Scutigera spec
• Thysanoptera for example Hercinoth ⁇ ps femorahs, Th ⁇ ps tabaci
• Heteroptera e.g. Eurygaster spp, Dysdercus intermedius, Piesma quadrata, Cimex lectula ⁇ us, Rhodnius prohxus, T ⁇ atoma spp
• From the order of the Homoptera for example Aleurodes brassicae, Bemisia tabaci, T ⁇ aleurodes vapora ⁇ orum, Aphis gossypn, Brevicoryne brassicae, Cryptomyzus ⁇ bis, Aphis fabae, Aphis pomi, E ⁇ osoma lamgerum, Hyalopterus arundinis, Phppoxemphoniphos, Phppoxemphoniphos, Phylloxeraphodum, Myppin, Phpp humuli,
• Rhopalosiphum padi Empoasca spp, Euscehs bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax st ⁇ atellus, Nilaparvata lugens, Aonidiella aurantn, Aspidiotus hederae, Pseudococcus spp, Psylla spp
• Tineola bissel ella Tinea pelhonella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Cho ⁇ stoneura fumiferana, Clysia ambiguella, Homona magnanima, Tort ⁇ x vi ⁇ dana
• Anthrenus spp Attagenus spp, Lyctus spp, Mehgethes aeneus, Ptinus spp, Niptus hololeucus, Gibbium psylloides, T ⁇ bolium spp, Teneb ⁇ o mohtor, Ag ⁇ otes spp, Conoderus spp, Melolontha melolontha, Amphimallely solstitia s
• Hymenoptera From the order of Hymenoptera, for example Dip ⁇ on spp, Hoplocampa spp, Lasius spp, Monomo ⁇ um pharaonis, Vespa spp
• Diptera From the order of Diptera, for example Aedes spp, Anopheles spp, Culex spp, Drosophila melanogaster, Musca spp, Fannia spp, Calhphora erythrocephala, Luci a spp, Chrysomyia spp, Cuterebra spp, Gastrophilus spp, Hyppobosca spp,
• 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
• Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp, Globodera spp, Meloidogyne spp, Aphelenchoides spp, Longidorus spp, Xiphinema spp, Trichodor spp
• the compounds of the formula (I) according to the invention are notable in particular for a high level of insecticidal and azide 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 polymeric substances
• formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solids Carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• Liquid solvents are essentially aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride , aliphatic hydrocarbons, such as cyclohexane or paraffins, for example Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as
• Solid carrier materials are suitable
• ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, or synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carrier materials for granules are, for example, broken and fractionated natural powders Rocks such as calcite, marble, pumice, sepiolite, dolomite or synthetic
• Granules from inorganic and organic flours or granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, as emulsifiers and / or foam-generating agents are possible, for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, poly - Oxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolyzates, and dispersants are, for example, lignin sulfite liquors and methyl cellulose
• Adhesives such as carboxymethyl cellulose, natural or synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho- lipids, such as cephalins and lecithins or synthetic phospholipids.
• 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 in general contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%
• the active compound 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 compounds, such as insecticides, attractants, stericants, bactericides, acaecides, nematicides, fungicides, growth-regulating substances or herbicides.
• active compounds such as insecticides, attractants, stericants, bactericides, acaecides, nematicides, fungicides, growth-regulating substances or herbicides.
• the insecticides include, for example, phosphoric acid esters, carbamates , Carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
• Fenarimol, Fenbuconazole, Fen Inenarimol, Fenbuconazole, Fen Nameam, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam,
• Fludioxonil fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl aluminum, fthalides, fuberidazole, furalaxyl, furmecyclox,
• copper preparations such as: copper hydroxide, copper naphthenate,
• 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, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
• Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
• Fenoxycarb fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, Fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
• 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,
• Tebufenozid Tebufenpyrad
• Tebupirimiphos Teflubenzuron
• Tefluthrin Temephos
• Terbam Terbufos
• Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuringiensin, Tralomenhrononium, Triomenethriazonium, Triomenethriazonium, Tri Vamidothion, XMC, Xylylcarb, YI 5301/5302, Zetameth ⁇ n
• 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 ingredient When used against hygiene and storage pests, the active ingredient is characterized by an excellent residual effect on wood and clay as well as a good alkaline action on limed substrates
• the active substances according to the invention act not only against plant, hygiene and
• animal parasites such as shield ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic larvae of larvae, lice, hangers, featherlings and fleas.
• ectoparasites animal parasites
• shield ticks leather ticks, rough mites, running mites, flies (stinging and licking), parasitic larvae of larvae, lice, hangers, featherlings and fleas.
• Anoplu ⁇ da for example Haematopinus spp, Linognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp From the order of the Mallophagida and the subordinates Amblyce ⁇ na and Ischnoce ⁇ na, e.g. T ⁇ menopon spp, Menopon spp, T ⁇ noton spp, Bovicola spp, Werneckiella spp, Lepikentron spp, Damalina spp, T ⁇ chodectes spp, Fe cola spp
• Nematocerma and Brachycerma e.g. Aedes spp, Anopheles spp, Culex spp, Simuhum spp, Eusimuhum spp, Phlebotomus spp, Lutzomyia spp, Cuhcoides spp, Chrysops spp, Hybomitra spp, Atylotus spp, Atylotusota, , Philipomyia spp, Braula spp, Musca spp, Hydrotaea spp, Stomoxys spp, Haematobia spp, Morel a spp, Fannia spp,
• Glossina spp Calhphora spp, Lucilia spp, Chrysomyia spp, Wohlfahrtia spp, Sarcophaga spp, Oestrus spp, Hypoderma spp, Gasterophilus spp, Hippobosca spp, Lipoptena spp, Melophagus 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 cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, Other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice are to be attacked by fighting these arthropods
• arthropods which are used for agricultural purposes, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, Other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice are to be attacked by fighting these arthropods
• 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, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or
• 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 It has also been found that the compounds of the formula (I) according to the invention have a high insecticidal action against insects which destroy industrial materials.
• Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucihegus, Mastoter es 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 it are to be understood as examples of 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 ingredients can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes
• 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 repellants, optionally siccatives and UV stabilizers and, if appropriate
• 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 optimum amount of use can be determined in each case by use of test series. In general, however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 up 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 difficultly volatile, 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, test gasoline 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, turpentine oil are advantageous and the like for use
• Evaporation rate 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 above 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
• Solvents or solvent mixtures replaced by an aliphatic polar organic-chemical solvent or solvent mixture.
• Aliphatic hydroxyl and / or ester and / or ether groups are preferably used organic chemical solvents such as glycol ether, ester or the like for use
• 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, e.g. polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin,
• Silicone resin drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin are used
• the synthetic resin used as the binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water repellents, odor agents and inhibitors or inhibitors Corrosion protection agents and the like are used
• 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.
• the 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 dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycol or glycerol glycol - ether, glycerol ester and p-toluenesulfonic acid ester.
• 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 by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
• the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides
• Possible additional admixing partners are preferably the insecticides and fungicides mentioned in WO 94/29 268.
• the compounds mentioned in this document are an express component of the present application.
• Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, are very particularly preferred mixing partners.
• the active compounds according to the invention also have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
• the active compounds are suitable for use as crop protection agents, in particular as fungicides
• Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chyt ⁇ diomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes
• Bactericidal agents are used in crop protection to combat Pseudomonadaeae, Rhizobiaceae, Enterobacte ⁇ aceae, Corynebacte ⁇ aceae and Streptomycetaceae
• Xanthomonas species such as, for example, Xanthomonas campest ⁇ s pv oryzae,
• Pseudomonas species such as, for example, Pseudomonas sy ⁇ ngae 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 humuh 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 für ginea,
• Podosphaera species such as, for example, Podosphaera leucot ⁇ cha, Ventu ⁇ a species, such as, for example, Ventu ⁇ a inaequalis,
• Pyrenophora species such as, for example, Pyrenophora teres or P graminea
• Cochliobolus species such as, for example, Cochliobolus sativus
• 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 herpotrichoides
• the active compounds according to the invention can, when used as fungicides as such, in
• 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 substance concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action
• logP The logP values were determined in accordance with EEC Directive 79/831 Annex V A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid) Examples of use
• Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist
• the death rate is determined in%. 100% means that all the beetle larvae have been killed, 0% means that no beetle larvae have been killed
• 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)
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• Dentistry (AREA)
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• Engineering & Computer Science (AREA)
• Plant Pathology (AREA)
• General Health & Medical Sciences (AREA)
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• Zoology (AREA)
• Environmental Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Quinoline Compounds (AREA)

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• 1997
  • 1997-11-14 DE DE1997150401 patent/DE19750401A1/de not_active Withdrawn
• 1998
  • 1998-10-31 EP EP98959820A patent/EP1037879A1/de not_active Withdrawn
  • 1998-10-31 WO PCT/EP1998/006909 patent/WO1999025694A1/de not_active Application Discontinuation
  • 1998-10-31 JP JP2000521078A patent/JP2001523667A/ja active Pending
  • 1998-10-31 AU AU15586/99A patent/AU1558699A/en not_active Abandoned

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