EP1037879A1 - Condensed pyridine derivatives - Google Patents

Abstract

The invention relates to compounds of formula (I), wherein R?1, R2, R3, R4¿, n and X have the meanings given in the Description, to a method for producing said compounds and to the use of said compounds for combating animal pests and as fungicides.

Description

Condensed pyridine derivatives

The present application relates to new condensed pyridine derivatives, processes for their preparation and their use for controlling animal pests and as fungicides.

It is already known that certain substituted 4-aminopyridines have insecticidal properties (cf. e.g. WO 93/04580, WO 96/08475, WO 96/10016, WO 96/14301 or WO 96/33975).

However, the effectiveness or range of action of these compounds is not always completely satisfactory, in particular at low application rates and concentrations

New condensed pyridine derivatives of the formula (I) were found

in which

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 and

n represents 0, 1, 2, 3 or 4,

including the pyridine N-oxides and salts protonated on pyridine nitrogen.

It has also been found that the compounds of the formula (I) can be obtained if

a) compounds of the formula (II)

in which

R ¹ , R ² , R ⁴ , X and n have the meaning given above,

with compounds of the formula (III)

R3_0-CO-G (III)

in which

R ^{3 has} the meaning given above and G represents a leaving group, for example halogen (especially chlorine or bromine) or imidazolyl;

in the presence of a base and optionally in the presence of a diluent

or

b) compounds of the formula (IV)

in which

R ¹ , R ² and R ^{3 have} the meaning given above,

with compounds of formula (V)

in which

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

Finally, it was found that the new compounds of formula (I) have strong biological properties and especially as fungicides and

Control of animal pests, in particular insects, arachnids and nematodes, which are suitable in agriculture, in the forests, in the protection of stocks and materials and in the hygiene sector

Surprisingly, the condensed pyridine derivatives according to the invention show a considerably better activity against animal pests than known compounds of similar constitution

The compounds according to the invention are generally defined by the formula (I)

Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below

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

Halogen, C ₁ -C ₄ -alkyl, C 4 alkoxy, C ₁ -C ₄ haloalkyl and C _j -C ₄ - haloalkoxy having in each case 1 to 5 identical or different halogen atoms, _C] -C -Alkylthιo, C ₁ -C -Alkylsulfιnyl, C ₁ -C alkylsulfonyl, further Cι-C ₄ -Halogenalkylthιo, C ₁ -C ₄ alkylsulfonyl same -Halogenalkylsulfιnyl and halo-C ₁ -C each having from 1 to 5 or different halogen atoms,

Nitro, cyano and aminothiocarbonyl come into question

R ⁴ also preferably represents 2-pyπdyl 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, Cι-C ₄ -Alkylthιo, _C] -C ₄ -Alkylsulfιnyl, C _j -C - alkylsulfonyl, also _C! -C ₄ -Halogenalkylthιo, -C-C ₄ -Halogenalkylsulfιnyl 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 -

C ₄ haloalkyl having 1 to 5 identical or different halogen atoms

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 Pyπdinπng 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,

Bromine, methyl, ethyl, methoxy, Tπfluormethyl and Tπfluormethoxy come into question

R ³ particularly preferably represents methyl, ethyl, isopropyl, allyl, cyclohexyl,

Phenyl or benzyl

R ⁴ particularly preferably represents phenyl which is substituted once or twice, identically or differently, where fluorine, chlorine,

Bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio, nitro, cyano and aminothiocarbonyl are suitable,

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

The general definitions or explanations of residues or explanations given above or in preferred areas apply accordingly to the end products and to 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 According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred).

According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

In the radical definitions given above and below, 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.

The following compounds of the formula (Ia) may be mentioned in particular:

Table a

(Continued in table a)

If, for example, N-quinolin-4-yl-4- (4-chlorophenoxy) phenylacetic acid amide and isopropyl chloroformate are used as starting materials in process (a), the course of the process according to the invention is shown by the following reaction scheme:

If, for example, 4-isopropoxycarbonylaminoquinoline and 4- (4-cyanophenoxy) phenylacetic acid chloride are used as starting materials in process (b), the course of the process according to the invention is shown by the following reaction scheme: iC ₃ H

The compounds of formula (II) required as starting materials for carrying out process (a) according to the invention are known (see WO 93/04580) and / or can be obtained in a generally known manner (see WO 93/04580 and WO 96 / 33975) by using 4-aminopyridines of the formula (VI)

in which

R ¹ and R ^{2 have} the meaning given above,

reacted with compounds of formula (V) according to process (b)

The 4-aminopyridines of the formula (VI) are known (cf., for example, J Praktische 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-Amιno-pyπdιne the

Reacts formula (VI) with compounds of formula (III) according to process (a)

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

The processes (a) and (b) described above for the preparation of the compounds of the formula (I) are carried out in the presence of a diluent. All customary solvents can be used as diluents

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

The processes (a) and (b) described above for the preparation of the compounds of the formula (I) are carried out in the presence of a base (cf. also Chem Ber 98, 829 (1965), Liebigs Ann Chem 739, 201 (1970) and 636 ( 1973)

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, pyπdin, chino n, diazabicyclooctane (DABCO),

Diazabicyclonones (DBN) and Diazabicycloundecen (DBU) 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.

When carrying out the processes (a) and (b) described above for the preparation of the compounds of the formula (I), 1 to 3 mol, preferably 1 to 2 mol, are generally employed per mole of compounds of the formula (II) or (IV) Compound of formula (III) or (V)

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

The end products are worked up and isolated in a generally known manner

With good plant tolerance and favorable warm-blood toxicity, 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

From the order of the Isopoda, for example Oniscus asellus, Armadilhdium vulgare, Porcellio scaber

From the order of the Diplopoda, for example, Blamulus guttulatus From the order of the Chilopoda, for example Geophilus carpophagus, Scutigera spec

From the order of the Symphyla eg Scutigerella Immaculata

From the order of the Thysanura, for example Lepisma sacchaπna

From the order of the Collembola, for example Onychiurus armatus

From the order of the Orthoptera, for example Blatta oπentahs, Peπplaneta ameπcana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp,

Locusta migratoπa migratoπoides, Melanoplus differentiahs, Schistocerca gregaπa

From the order of the Dermaptera eg Forficula auπculaπa

From the order of the Isoptera, for example Reticulitermes spp

From the order of the Anoplura, for example Pediculus humanus corpoπs, Haematopinus spp, Linognathus spp

From the order of the Mallophaga, for example Tπchodectes spp, Damahnea spp

From the order of the Thysanoptera, for example Hercinothπps femorahs, Thπps tabaci

From the order of Heteroptera e.g. Eurygaster spp, Dysdercus intermedius, Piesma quadrata, Cimex lectulaπus, Rhodnius prohxus, Tπatoma spp

From the order of the Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Tπaleurodes vaporaπorum, Aphis gossypn, Brevicoryne brassicae, Cryptomyzus πbis, Aphis fabae, Aphis pomi, Eπosoma lamgerum, Hyalopterus arundinis, Phppoxemphoniphos, Phppoxemphoniphos, Phylloxeraphodum, Myppin, Phpp humuli,

Rhopalosiphum padi, Empoasca spp, Euscehs bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax stπatellus, Nilaparvata lugens, Aonidiella aurantn, Aspidiotus hederae, Pseudococcus spp, Psylla spp

From the order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniaπus, Cheimatobia brumata, LithocoUetis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustπa, Euproctis chrysorrhoea, Lymantπa spp, Phocellellapppp, Bucculppas insulana, Heliothis spp, Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera htura, Spodoptera spp, Tπchoplusia ni, Carpocapsa pomonella, Pieπs spp, Chilo spp, Pyrausta nubilalis, Ephestia kuehmellon, Galleπa

Tineola bissel ella, Tinea pelhonella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choπstoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortπx viπdana

From the order of the Coleoptera, e.g. Anobium punctatum, Rhizopertha dommica,

Bruchidius obtectus, Acanthosce of obtectus, cochleaπae Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemhneata, Phaedon, Diabrotica spp, Psylliodes chrysocephala, Epilachna vaπvestis, Atomaπa spp spp Oryzaephilus suπnamensis, Anthonomus spp Sitophilus, Otiorrhynchus sulcatus, Cosmopo tes sordidus, Ceuthorrhynchus assimihs, Hypera postica, Dermestes spp, Trogoderma spp,

Anthrenus spp, Attagenus spp, Lyctus spp, Mehgethes aeneus, Ptinus spp, Niptus hololeucus, Gibbium psylloides, Tπbolium spp, Tenebπo mohtor, Agπotes spp, Conoderus spp, Melolontha melolontha, Amphimallely solstitia s

From the order of Hymenoptera, for example Dipπon spp, Hoplocampa spp, Lasius spp, Monomoπum pharaonis, Vespa spp

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,

Stomoxys spp, Oestrus spp, Hypoderma spp, Tabanus spp, Tannia spp, Bibio hortulanus, Oscinella fπt, Phorbia spp, Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa

From the order of the Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp

From the order of the Arachnida, for example Scorpio maurus, Latrodectus mactans

From the order of the Acarina, for example Acarus siro, Argas spp, Ornithodoros spp, Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp, Rhipicephalus spp, Amblyomma spp, Hyalomma spp, Ixodes spp, Psoroptes spp,

Chorioptes spp, Sarcoptes spp, Tarsonemus spp, Bryobia praetiosa, Panonychus spp, Tetranychus spp

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

They can be used with particularly good success to control plant-damaging insects, such as, for example, against the larvae of the horseradish beetle (Phaedon cochleariae) or the caterpillars of the owl butterfly (Spodoptera exigua)

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

These 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.

If water is used as an extender, 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

Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water

Solid carrier materials are suitable

e.g. 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. The insecticides include, for example, phosphoric acid esters, carbamates , Carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others

The following are particularly advantageous mixed partners

Fungicides:

2-aminobutane, 2-anion-4-methyl-6-cyclopropyl-pyπmιdιn, 2 ', 6'-di-bromo-2-methyl-4'-tπfluoromethoxy-4'-tπfluoromethyl-l, 3-thιazol-5- carboxanιlιd, 2,6-DιchloroN- (4-tπfluoromethylbenzyl) -benzamιd, (E) -2-methoxyιmιno-N-methyl-2- (2-phenoxy-phenyl) -acetamιd, 8-Hydroxyquιnolιnsulfat, methyl- (E) - 2- {2- [6- (2-cyanophenoxy) - pyπmιdιn-4-yloxy] phenyl} -3-methoxyacrylate, methyl- (E) -methoxιmιno [alpha- (o-tolyloxy) -o-tolyl] acetate, 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole, Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,

Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb,

Cymoxanil, cyproconazole, cyprofüram,

Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,

Edifenphos, epoxyconazole, ethirimol, etridiazole,

Fenarimol, Fenbuconazole, Fenfüram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam,

Fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl aluminum, fthalides, fuberidazole, furalaxyl, furmecyclox,

Guazatine,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,

Kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate,

Copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,

Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfüroxam, Metiram, Metsulfovax, Myclobutanil,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol, Ofrace, oxadixyl, oxamocarb, oxycarboxin,

Pefürazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,

Quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,

Validamycin A, vinclozolin,

Zineb, ziram

Bactericides:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, teclofalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M,

Azocyclotin,

Bacillus thuringiensis, Bendiocarb, Benfüracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,

Cadusafos, Carbaryl, Carbofüran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocytezhrinhrinhrinhrinhrinhrinhrin, Clofythrinhrinhrinhrin, Clofythrinhrinhrinhrin, Clofythrinhrinhrinhrinhrin, Clofythrinhrinhrinhrin, Clofythrinhrinhrinhrinhrinhrin, Clofythrinhrinhrinhrinhrin, Clofythrinhrinhrinhrinhrinotin Cyhexatin, cypermethrin,

Cyromazine,

Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,

Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,

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,

HCH, heptenophos, hexaflumuron, hexythiazox,

Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,

Lambda cyhalothrin, lufenuron,

Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos,

Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,

Naled, NC 184, NI 25, Nitenpyram

Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,

Pyriadaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,

Quinalphos,

RH 5992,

Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,

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, Zetamethπn

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible

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

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

Storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as shield ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic larvae of larvae, lice, hangers, featherlings and fleas. These parasites include

From the order of the Anopluπda, for example Haematopinus spp, Linognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp From the order of the Mallophagida and the subordinates Amblyceπna and Ischnoceπna, e.g. Tπmenopon spp, Menopon spp, Tπnoton spp, Bovicola spp, Werneckiella spp, Lepikentron spp, Damalina spp, Tπchodectes spp, Fe cola spp

From the order Diptera and the subordinates 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

From the order of the Siphonapteπda e.g. Pulex spp, Ctenocepha des spp,

Xenopsylla spp, Ceratophyllus spp

From the order of the Heteropteπda, for example Cimex spp, Tπatoma spp, Rhodnius spp, Panstrongylus spp

From the order of the Blattaπda, for example Blatta oπenta s, Peπplaneta ameπcana, Blattela germanica, Supella spp

From the subclass of the Acaπa (Acaπda) and the orders of the Meta and Mesostigmata e.g. Argas spp, Ornithodorus spp, Otobius spp, Ixodes spp,

Amblyomma spp, Boophilus spp, Dermacentor spp, Haemophysahs spp, Hyalomma spp, Rhipicephalus spp, Dermanyssus spp, Railhetia spp, Pneumonyssus spp, Sternostoma spp, Varroa spp

From the order of the Actinedida (Prostigmata) and Acaπdida (Astigmata) z

Acarapis spp, Cheyletiella spp, Ornithocheyletia spp, Myobia spp, Psorergates spp, Demodex spp, Trombicula spp, Listrophorus spp, Acarus spp, Tyrophagus spp, Caloglyphus spp, Hypodectes spp, Pterolichus spp, Psoroptes spp, Choπoptes spp, Otodectes spp, Sarcoptes spp, Notoedres spp, Knemidocoptes spp, Cytodites spp, Laminosioptes 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

Reductions in performance (for meat, milk, wool, skin, eggs, honey, etc.) are reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry

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

Bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped bodies containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holders, marking devices, etc

When used for cattle, poultry, pets, etc., 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.

The following are examples and preferably - but without limitation -

Called insects:

Beetle like

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces rugus, Lyctus pubescescus, Lyctus pubis linearis, Lyctus linearesces rug Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus

Skin wings like

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur

Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifügus, Mastoter es darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails, such as Lepisma saccarina.

In the present context, technical materials are understood to mean 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

Material around wood and wood processing products. 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

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 repellants, 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 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

An 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 The organic-chemical solvents used 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

In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or spindeol and / or monochloronaphthalene, preferably α-mono- chlorophane cock used

The organic volatile oily or oil-like solvents with a

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

According to a preferred embodiment, part of the organic chemical

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

In the context of the present invention, 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

According to the invention, 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. According to the invention, alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68%, are preferred % By weight used

All or part of the binder mentioned can be replaced by a fixative (gemιsch) or a plasticizer (gemιsch). 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.

Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron and Triflumuron, as well as fungicides such as Epoxyconazole, Hexaconazole, Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanidyl, 3-Iodylfluanid, Tolyl-3-Iodyl-Flanidyl, Iodyl-2-Fluoro-Iodide -isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one in question 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, Chytπdiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes

Bactericidal agents are used in crop protection to combat Pseudomonadaeae, Rhizobiaceae, Enterobacteπaceae, Corynebacteπaceae and Streptomycetaceae

Some pathogens of fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation

Xanthomonas species, such as, for example, Xanthomonas campestπs pv oryzae,

Pseudomonas species, such as, for example, Pseudomonas syπngae 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

Pseudoperonospora cubensis,

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 leucotπcha, Ventuπa species, such as, for example, Ventuπa inaequalis,

Pyrenophora species, such as, for example, Pyrenophora teres or P graminea

(Conidial form Drechslera, Syn Helminthospoπum), 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 herpotrichoides

The fact that the active ingredients are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil

In addition, they show a broad in vitro activity against phytopathogenic fungi

The active compounds according to the invention can, when used as fungicides as such, in

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 pouring, spraying, atomizing, scattering, scattering , Brushing, etc. It is also possible to use the active ingredients according to the ultra-low

Apply volume method or the drug preparation or the drug to inject yourself into the soil The seeds of the plants can also be treated

In the treatment of parts of plants, 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.

In the case of seed treatment, amounts of active compound of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required

When treating the soil, 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

The preparation and use of the active compounds according to the invention can be seen from the examples below

Manufacturing examples

example

(Method a)

To 1.75 g (4.5 mmol) of N-quinolin-4-yl-4- (4-chlorophenoxy) phenylacetic acid amide (cf. WO 93/04580, Ex. 61) in 50 ml of tetrahydrofuran, 0.13 g (5, 4 mmol) of sodium hydride (60%) are added and the mixture is stirred until the evolution of hydrogen has ended

9.0 ml (9.0 mmol) of a 1 molar solution of isopropyl chloroformate in toluene are then added dropwise at -5 ° C. to 0 ° C. and the mixture is stirred overnight at room temperature

For working up, the reaction solution is partitioned between ethyl acetate and water, the organic phase is dried and concentrated by distilling off the solvent. Chromatographic purification on silica gel (chloroform / acetone 95/5) gives 0.28 g (13% of theory) of N-quinoline -4-yl-N-isopropoxycarbonyl-4- (4-chlorophenoxy) phenylacetic acid amide with a logP (pH2) = 4 35

^! H-NMR (CDCI ₃ ) 0 95 (d, 3H), 1 05 (d, 3H), 4 45 (m, 2H), 4 95 (m, 1H), 6 90 - 7 90 (m, 12H), 8 15 (d, 1H), 8 95 (d, 1H) ppm

[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

In the following application examples, the compound of the formula (A) known from WO 96/33975 was

used as a reference substance.

Example A

Phaedon larval test

Solvent 7 parts by weight of dimethylformamide emulsifier 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of 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 with water to the desired concentration

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

After the desired time, 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

In this test, at an exemplary active ingredient concentration of 0.0008%, the compound according to Preparation Example 1 caused a death rate of 100%, while the known compound (A) had no effect, in each case after 6 days

Example B

Spodoptera exigua test

Solvent 7 weight unit dimethylformamide

Emulsifier 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration

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

After the desired time, 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

In this test, at an exemplary active ingredient concentration of 0.0008%, the compound according to Preparation Example 1 caused a death rate of 100%, while the known compound (A) only caused 50% death rate, in each case after 6 days

Claims

claims

1 compounds of formula (I)

in which

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 and

n represents 0, 1, 2, 3 or 4,

including the Pyπdin-N-oxides and salts protonated on the Pyπdin nitrogen

2 compounds of formula (I) according to claim 1 in which R ¹ and R ² together with the carbon atoms to which they are attached represent an optionally monosubstituted to trisubstituted, identically or differently, mono- or polyunsaturated 5 or 6-ghedπgen, in particular carboxyclic ring, the preferred substituents being halogen, C _j -C ₄ alkyl, C _] -C alkoxy, Ci-

C ₄ -haloalkyl and Cj-C ₄ -haloalkoxy, each with 1 to 5 identical or different halogen atoms, are suitable,

R ³ is Cι-C ₄ alkyl, C ₂ -C ₄ alkenyl, optionally substituted once to three times, identically or differently, by C1-C ₄ - alkyl or halogen substituted C ₅ -CG-cycloalkyl, or in each case optionally mono- to trisubstituted, identically or differently substituted, phenyl or benzyl, in each case preferably halogen, C _j -C ₄ alkyl, C _] -C ₄ alkoxy and C _j -C ^ haloalkyl and C _j -C ₄ - as substituents Haloalkoxy with 1 to 5 identical or different halogen atoms in question,

R ^{4 represents} phenyl which is optionally monosubstituted to pentasubstituted by identical or different substituents, the preferred substituents being halogen, C _j ^ alkyl, C _j -C ^ alkoxy, C _j -C ^ haloalkyl and Ci

C ₄ haloalkoxy each having 1 to 5 identical or different halogen atoms, C _] -C ₄ alkylthio, C 1 -C ₄ alkylsulfinyl, C _r C ₄ - alkylsulfonyl, furthermore C _j -C ₄ haloalkylthio, C _] -C ₄ - Haloalkylsulfinyl and C _] -C -haloalkylsulfonyl, each with 1 to 5 identical or different halogen atoms, nitro, cyano and aminothiocarbonyl in

Question come, or

optionally monosubstituted to trisubstituted by identical or different substituents 2-Pyπdyl, preferred substituents being halogen, C _j -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ haloalkyl and C _j -

C ₄ haloalkoxy each having 1 to 5 identical or different halogen atoms, C _j -C ₄ alkylthio, C _j -C ^ alkylsulfinyl, C _| -C ₄ - alkyl sulfonyl; Further, Cj-C ₄ haloalkylthio, C] -C ₄ haloalkylsulfinyl and _{Cι-C4-haloalkylsulfonyl} having in each case 1 to 5 identical or different halogen atoms, nitro, cyano and aminothiocarbonyl come into question,

X for fluorine, chlorine, bromine, C, -C ₄ alkyl, C _r C ₄ - alkoxy or C _r C ₄ -

Haloalkyl having 1 to 5 identical or different halogen atoms, and

n stands for 0, 1 or 2.

3. Compounds of formula (I) according to claim 1 in which

R ¹ and R ² together with the pyridine ring to which they are attached represent the following ring systems:

which are optionally monosubstituted to trisubstituted, identically or differently, fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl and trifluoromethoxy being suitable as substituents,

R ^{3 represents} methyl, ethyl, isopropyl, allyl, cyclohexyl, phenyl or benzyl,

R ^{4 represents} phenyl which is mono- or disubstituted, identically or differently substituted, fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio, nitro, cyano and aminothiocarbonyl being suitable as substituents or for 2-pyridyl, optionally substituted once or twice, identically or differently, by chlorine, methyl and trifluoromethyl.

X represents fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl, and

n stands for 0 or 1.

A process for the preparation of compounds of formula (I) according to claim 1, characterized in that

a) compounds of the formula (II)

in which

R ¹ , R ² , R ⁴ , X and n have the meaning given in claim 1,

with compounds of the formula (III)

in which

R ^{3 has} the meaning given in claim 1 and stands for a leaving group,

or

b) compounds of the formula (IV)

in which

R ¹ , R ² and R ^{3 have} the meaning given above,

with compounds of formula (V)

in which

G, R ⁴ , X and n have the meaning given above,

in each case in the presence of a base and optionally in the presence of a diluent.

Compounds of formula IV

in which

R ¹ , R ² and R ^{3 have} the meaning given in claim 1

Pesticides and antifungal agents, characterized in that they contain at least one compound of the formula (I) according to Claim 1

Use of compounds of the formula (I) according to Claim 1 for combating pests and fungi

Process for combating pests and fungi, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests or fungi and / or their habitat

Process for the preparation of pesticides and fungicides, characterized in that compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents

Use of compounds of formula (I) according to claim 1 for the preparation of pesticides and fungicides