WO1993024484A1

WO1993024484A1 - Substituted 2-arylpyrroles

Info

Publication number: WO1993024484A1
Application number: PCT/EP1993/001230
Authority: WO
Inventors: Hermann Uhr; Albrecht Marhold; Peter Andres; Christoph Erdelen; Ulrike Wachendorff-Neumann; Wilhelm Stendel
Original assignee: Bayer Aktiengesellschaft
Priority date: 1992-05-29
Filing date: 1993-05-17
Publication date: 1993-12-09
Also published as: DE4217725A1; AU4069193A

Abstract

New substituted 2-arylpyrroles having formula (I), in which Y?1, Y?2, R?1, R?2, R?3, R?5 and R?6 have the meaning given in the description, are disclosed, as well as a process for preparing the same. These new 2-arylpyrroles are used as pest control agents.

Description

Substituted 2-aryipyrroie

The present invention relates to new substituted 2-arylpyrroles, intermediates for their preparation and their use for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in the forests, in the protection of stocks and materials and in the hygiene sector . It has already become known that structurally similar cyanopyrroles are effective as molluscicides, fungicides and insecticides (see, for example, EP-A

0 347 488, EP-A 0 358 047, EP-A 0 312 723, DE-A 4 117 752). The effectiveness and range of action of these compounds, however, is not always completely satisfactory, especially at low application rates and concentrations.

New substituted 2-aryipyrroles of the general formula (I)

in which

R ^{1 represents} cyano or nitro

R ² for the residues

wöbei

X ¹ , X ² , X ³ and X ^{4 may be the} same or different

can represent hydrogen, halogen or alkyl,

R ^{4 represents} halogen and n represents a number from 0 to 3,

R ^{3 represents} hydrogen, phenyl or optionally

substituted alkyl, R ⁵ and R ⁶ independently of one another for hydrogen, in each case optionally substituted alkyl,

Are alkenyl, alkynyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl, alkylcarbonyl or where the radicals R ⁵ and R ⁶ together with the nitrogen atom enclosed by them form a cycle,

Y ^{1 represents} halogen and Y ^{2 represents} halogen, alkyl or haloalkyl.

It was also found that the substituted 2-arylpyrroles of the general formula (I)

in which

R ¹ is cyano or nitro, R ² for the residues

wöbe i

X ¹ , X ² , X ³ and X ^{4 may be the} same or different

can represent hydrogen, halogen or alkyl,

R ^{4 represents} halogen and n represents a number from 0 to 3

R ^{3 represents} hydrogen, phenyl or optionally substituted alkyl,

R ⁵ and R ⁶ independently of one another for hydrogen,

each optionally substituted alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl, alkyl carbonyl or where the radicals R ⁵ and R ⁶ together with the nitrogen atoms enclosed by them form a cycle, Y ¹ for halogen and

Y ^{2 represents} halogen, alkyl or shark ogenalkyl, is obtained if

2-arylpyrroles of the formula (II)

in which

R ¹ , R ² , Y ¹ and Y ^{2 have} the meaning given above, with compounds of the formula (III)

in which

R ³ , R ⁵ and R ^{6 have} the meaning given above and

X ^{6 represents} an anionic leaving group, if appropriate in the presence of bases and / or if appropriate in the presence of diluents, Finally, it was found that the new substituted 2-aryipyrroles of the formula (I) have highly pronounced biological properties and above all to control animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in the forests, in the supply and material protection as well as in the hygiene sector are suitable.

The new substituted 2-arylpyrroles according to the invention are defined by the general formula (I).

Substituted 2-arylpyrroles of the above formula (I) in which R ^{1 represents} cyano or nitro, R ^{2 represents} the radicals, are preferred

.

wöbei X ¹ , X ² , X ³ and X ^{4 may be the} same or different and represent hydrogen, halogen or

Are C ₁ -C ₆ alkyl,

R ^{4 represents} halogen and n represents a number from 0 to 3,

R ^{3 represents} hydrogen, phenyl or C ₁ -C ₈ alkyl,

which is optionally substituted by 1 to 6 halogen atoms, C ₁ -C ₆ alkoxy, C ₁ -C ₆ -alkylthio, (C ₁ - C ₆ alkyl) carbonyloxy, (C ₁ -C ₆ alkoxy) carbonyl, phenyl , Cyano or nitro,

R ⁵ and R ⁶ independently of one another represent hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkeny 1 or C ₃ -C ₈ -alkynyl1, the alkyl, alkenyl or alkynyl radicals optionally being represented by 1 to 6 identical or different radicals of the series halogen, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkyl) carbonyloxy, (C ₁ -C ₆ alkoxy) carbonyl, optionally substituted

Phenyl, cyano or nitro are substituted, or represent (C ₁ -C ₈ alkoxy) carbonyl, (C ₁ -C ₈ alkenoxy) carbonyl or (C ₃ -C ₈ alkynoxy) carbonyl, the alkoxy -, Alkenoxy or alkynoxy, optionally by 1 to 6 identical or different radicals from the series halogen, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkyl) carbonyloxy, (C ₁ -C ₆ -A-koxy) -carbonyl, optionally substituted phenyl, cyano or nitro are substituted, or wherein R ⁵ and R ^{6 represent} (C ₁ -C ₈ alkyl) carbonyl, which is optionally substituted by 1 to 6 identical or different radicals from the series halogen, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkyl) carbonyloxy, (C ₁ -C ₆ alkoxy) carbonyl, optionally substituted phenyl, cyano or nitro, or where the radicals R ⁵ and R ⁶ together with the nitrogen atom enclosed by them form a 4- form up to 8-membered ring. Y ^{1 represents} fluorine, chlorine, bromine or iodine and

Y ² for fluorine, chlorine, bromine, iodine, C ₁ -C ₄ alkyl or

C ₁ -C ₄ haloalkyl. Substituted 2-arylpyrroles of the above formula (I), in which cyano or nitro represents the radicals, are particularly preferred

.

wöbei X ¹ , X ² , X ³ and X ^{4 can be the} same or different and represent hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl,

R ^{4 represents} fluorine, chlorine or bromine and n represents a number from 0 to 2,

R ^{3 represents} hydrogen, phenyl or C ₁ -C ₆ alkyl, which is optionally substituted by 1 to 5 fluorine and / or chlorine atoms, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, (C ₁ -C ₄ - alkyl) carbonyloxy, (C ₁ -C ₄ alkoxy) carbonyl, phenyl, cyano or nitro,

R ⁵ and R ⁶ independently of one another represent hydrogen, C 1 -C ₆ -alkyl, C ₃ -C ₆ -alkenyl or C ₃ -C ₆ -alkynyl, the alkyl, alkenyl or alkynyl radicals optionally being represented by 1 to 5 Radicals of the series fluorine, chlorine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, (C ₁ -C ₄ alkyl) carbonyloxy, (C ₁ -C ₄ alkoxy) carbonyl, optionally substituted phenyl, Cyano or

Are nitro-substituted, or represent (C ₁ -C ₆ -alkoxy) carbonyl, (C ₃ -C ₆ -alkenoxy) carbonyl or (C ₃ -C ₆ -alkynoxy) carbonyl, the alkoxy,

Alkenoxy or alkynoxy part, optionally with 1 to 5 radicals from the series fluorine, chlorine, C ₁ -C ₄ -alkoxy,

C ₁ -C ₄ alkylthio, (C ₁ -C ₄ alkyl) carbonyloxy, (C ₁ -C ₄ alkoxy) carbonyl, optionally substituted Phenyl, cyano or nitro are substituted, or represent (C ₁ -C ₆ alkyl) carbonyl, which may be by 1 to 5 fluorine and / or chlorine atoms, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - Alkylthio, (C ₁ -C ₄ alkyl) carbonyloxy, (C ₁ -C ₄ alkoxy) carbonyl, optionally substituted phenyl, cyano or nitro, or where the radicals R ⁵ and R ⁶ together with those enclosed by them Nitrogen atoms form a 4- to 6-membered ring, Y ^{1 represents} chlorine or bromine and

Y ^{2 represents} chlorine, bromine or CF ₃ .

Come as substituents for the optionally substituted phenyl radicals listed above

Preferred white in question: halogen, in particular fluorine, chlorine, bromine, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy.

Is used according to method b) 4,5-dibromo-3-cyano-2- (2,2,3,3-tetrafluorobenzo-1,4-dioxol-6-y1) pyrrole and

Chloromethyl ethyl ether as starting products, the course of the reaction can be represented by the following reaction scheme:

The compounds of the general formula (II) required as starting materials in the production process

in which

R ¹ , R ² , Y ¹ and Y have the meaning given above, are known (DE-A 4 117 752) and / or can be prepared by methods known in principle (see, for example,

I.A. Benages et al, J. Org. Chem. 43, 4278 (1978), EP-A 0 347 488 or ÜS-A 5 030 735).

The starting materials of the general formula (III) used in the production process are known and / or can be prepared by methods known in principle (see, for example, KG Siver et al., J. Pharm. Sei, 79, 66 (1990)). The process of making compounds of the

Formula (I) is characterized in that compounds of the formula (II) with compounds of the formula

(III), if appropriate in the presence of bases and if appropriate in the presence of diluents.

All inert organic solvents are suitable as diluents in the process according to the invention. These preferably include hydrocarbons such as

Benzene, toluene, xylene, further ethers, such as dibutyl ether, tert. -Butyl methyl ether, tetrahydrofuran, dioxane, and also polar solvents, such as dimethyl sulfoxide, acetonitrile, sulfolane, dimethyl formamide and N-methyl-pyrrolidone. All conventional proton acceptors can be used as bases in the process according to the invention. Alkali metal and alkaline earth imetal 1-oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide or 18- Krone-6 can be used. Alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butylate, can also be used, The reaction temperatures can be varied within a wide range when carried out. In general, temperatures between -10 ° C and 200 ° C, preferably between 0 ° C and 120 ° C, the reaction components of the formula (II), the deprotonating bases and the components of the formula (III) generally in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).

The process is generally carried out under normal pressure, but it can also be carried out under pressure.

The processing of those produced according to the invention

Compounds of formula (I) are made by conventional methods, e.g. Extraction with organic solvents, chromatography etc.

The substituted 2-arylpyrroles (I) according to the invention are suitable for combating, with good plant tolerance and favorable warm-blood toxicity

animal pests, especially insects,

Arachnids and nematodes found in agriculture, in forests, in the protection of stocks and materials, and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual development stages. The pests mentioned above include: From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda e.g. Blaniulus

guttulatus.

From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla e.g. Scutigerella immaculate.

From the order of the Thysanura e.g. Lepisma saccharina.

From the order of the Collembola e.g. Onychiurus armatus. From the order of the Orthoptera e.g. Blatta orientalis,

Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis,

Schistocerca gregaria,

From the order of the Dermaptera e.g. Forficula auricularia.

From the order of the Isoptera e.g. Reticulitermes spp .. From the order of the Anoplura e.g. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp, from the order of the Thysanoptera e.g. Herc inothrips femoralis, Thrips tabaci.

From the order of the Heteroptera e.g. Eurygaster spp.,

Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis

gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum,

Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalos iphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus,

Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatαbia brumata, Lithocolletis blancardel la, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiel la, Phyllocnistis citrella, Agrotis spp., Euxoa spp «, Feltia spp., Earias insulana, Heliothis spp ,, Laphygma exigua, Mame- strass brassicae, Panolis flammea, Prodenia litura,

Spodoptera spp ,, Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophi la pseudospretella,

Cacoecia podana, Capua reticulana, Choristoneura

fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera, e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa deceml ineata, Phaedon cochleariae, Diabro- tica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Ot iorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilpperm, Trogoder spp., Hyperahrenma. Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealand.

From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp.,

Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp «, Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyatitis hyoscyami capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophy1 lus spp ..

From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.

From the order of the Acarina, for example Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyl locoptruta oleivora, Boophilus spp., Rhipi cephalus spp., Amblyomma spp., Hyalomma spp.,

Ixodes spp ,, Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp .. The substituted 2-aryipyrroles (I) according to the invention not only act against plant, hygiene and ^Storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tortoise ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitizing

Fly larvae, lice, hair lice, featherlings, fleas.

They are effective against normally sensitive and resistant species and strains, as well as against all parasitic and non-parasitic stages of development of the ectoparasites.

The substituted 2-arylpyrroles (I) according to the invention are notable for high insecticidal activity. They can be used with good success against plant-damaging insects, for example against the

Use larvae of horseradish leaf beetles (Phaedon cochleariae), against green peach aphids (Myzus persicae) or against black bean leaf lice (Aphis fabae). The active compounds according to the invention show not only protective but also leaf-systemic and root-systemic properties.

In addition, the substituted 2-aryipyrroles (I) according to the invention are also suitable for controlling soil insects and can be used, for example, to control the maggots of the onion fly (Phorbia antiqua) in the soil.

In addition, the substituted 2-arylpyrroles (I) according to the invention have a high activity against pests of hygiene and pests and can be used, for example, to control the German cockroach (Blattella germanica).

The substituted 2-arylpyrroles (I) according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as

Incense cartridges, cans, spirals, etc., as well as ULV cold and warm mist formulations,

These formulations are made in a known manner, e.g. by mixing the substituted 2-arylpyrroles (I) according to the invention with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents

Agents, ie emulsifiers and t or dispersants and / or foam-generating agents. In case of

Use of water as an extender can e.g. also organic solvents as auxiliary solvents

be used. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or Alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,

Chlorethylene or methylene chloride, aliphatic

Hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl formamide and dimethyl sulfoxide, and water; Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers are possible: e.g. natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates; Solid carriers for granulates are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic

Material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers 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; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose. Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g.

Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used

become. The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The substituted 2-arylpyrroles (I) according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, 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 The substituted 2-arylpyrroles (I) 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 through which the action of the active ingredients 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 ingredient concentration of the use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight. The application is carried out in a manner custom-adapted to the application .

When used against hygiene pests and pests of stored products, the active substances are distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.

The 2-arylpyrroles (I) substituted according to the invention are also suitable for controlling insects, mites, ticks, etc. in the field of animal husbandry and

Livestock breeding, whereby pest control can achieve better results, e.g. higher milk yields, higher weight, more beautiful animal fur, longer lifespan etc. The use of the substituted 2-arylpyrroles (I) according to the invention takes place in this field in a known manner, such as by oral use in the form of, for example, tablets, capsules, waterings, granules, by dermal or external use in the form of, for example, immersion (dipping), spraying (Spraying), pouring (pour-on and spot-on) and powdering as well as by parenteral application in the form of, for example

Injection and also through the "feed-through" process. There is also an application as

Shaped body (collar, ear tag) possible.

The following examples describe the production and use of active compounds according to the invention without restricting them to them.

Manufacturing examples

example 1

3 g (0.0066 mo 1) 4, 5-dibromo-3-cyano-2- (2,2,3,3-tetrafluorobenzo-1,4-dioxol-6-yl) pyrrole are dissolved in 50 ml of dry tetrahydrofuran (THF) dissolved and mixed with 0.88 g (0.0079 ml) of potassium tert-butoxide. A solution of 1.24 g (0.0069 mol) of N-propyl-N-chloromethyl-carbamic acid ethyl ester in 20 ml of THF is then added dropwise, and the mixture is stirred at room temperature for 16 hours. Water is added and the mixture is extracted with methylene chloride. The combined extracts are dried over sodium sulfate and evaporated.

The crude product is purified by chromatography on silica gel (eluent: methylene chloride).

Yield: 2.6 g (66% of theory)

¹ H NMR (CDCl ₃ ) δ = 0.75 (3H, t), 1.10-1.30 (5H, m), 2.85

(2H, dd), 3.95 (2H, q), 5.60 (2H, s), 7.15-7.35 (3H, m).

The substances of the formula (I) listed below in Table 1 are obtained in an analogous manner and taking into account the information in the description.

t c

Examples of use

In the following application examples, the following compound was used as a comparison substance

1- (ethoxymethyl) -2- (4-trifluoromethyl-phenyl) -3-cyano-4,5-dichloropyrrole known from EP-A 0 347 488

Example: A

Plutella 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 dipping them into the active ingredient preparation of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella maculipennis) while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0 V. means that no caterpillars have been killed.

In this test, for example, the following compounds of the preparation examples show activity which is superior to the prior art: 1, 3, 4, 5, 6, 7, 8, 10, 11, 12.

Example B

Tetranychus test (phosphorester resistant)

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 containing emulsifier to the desired concentrations,

Bean plants (Phaseolus vulgaris) which are heavily infested with all stages of development of the common spider mite or bean spider mite (Tetranychus urticae) are sprayed to runoff point with an active ingredient preparation of the desired concentration. After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.

In this test, for example, the following compound of the preparation examples shows superior activity compared to the prior art: 1, 6, 7, 8.

Claims

1. Substituted 2-arylpyrroles of the general formula (I)

in which

R ^{1 represents} cyano or nitro,

R ² for the residues

in which

X ¹ , X ² , X ³ and X ^{4 may be the} same or different and represent hydrogen, halogen or alkyl, R ^{4 represents} halogen and n represents a number from 0 to 3

R ^{3 represents} hydrogen, phenyl or optionally substituted alkyl,

R ⁵ and R ⁶ independently of one another represent hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl, alkylcarbonyl or the radicals R ⁵ and R ⁶ together with the nitrogen atom enclosed by them form a cycle, Y ^{1 represents} halogen and Y ^{2 represents} halogen, alkyl or haloalkyl

2. Substituted 2-arylpyrroles of formula (I) according to claim 1, in which

R ^{1 represents} cyano or nitro

R ² for the residues,

in which

X ¹ , X ² , X ³ and X ^{4 can be the} same or different and represent hydrogen, halogen or C ₁ -C ₆ alkyl,

R ^{4 represents} halogen and n represents a number from 0 to 3, R ^{3 represents} hydrogen, phenyl or C ₁ -C ₈ alkyl

group, which is optionally substituted by 1 to 6 halogen atoms, C ₁ -C ₆ alkoxy, C ₁ - C ₆ alkylthio, (C ₁ -C ₆ alkyl) carbonyloxy, (C ₁ - C ₆ alkoxy) carbonyl, Phenyl, cyano or nitro,

R ⁵ and R ⁶ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl or C ₃ -C ₈ -alkynyl, the alkyl, alkenyl or alkynyl radicals optionally being represented by 1 to 6 identical or different radicals from the halogen series, C ₁ -

C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkyl) carbonyloxy, (C ₁ -C ₆ alkoxy) carbonyl, optionally substituted phenyl, cyano or nitro, or for (C ₁ -C ₈ alkoxy) carbonyl, (C ₃ -C ₈ alkenoxy) carbonyl or (C ₃ -C ₈ alkynoxy) carbonyl, the alkoxy, alkenoxy or alkynoxy part optionally being 1 to 6 identical or different Residues of the halogen series, C ₁ -C ₆ - Alkoxy, C ₁ -C ₆ -alkylthio, (C ₁ -C ₆ -alkyl) carbonyloxy, (C ₁ -C ₆ -alkoxy) carbonyl, optionally substituted phenyl, cyano or nitro or where R ⁵ and R ⁶ are substituted for ( C ₁ -C ₈ alkyl) carbonyl, which is optionally substituted by 1 to 6 identical or different radicals from the series halogen, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ - C ₆ - Alkyl) carbonyloxy, (C ₁ -C ₆ -alkoxy) carbonyl, optionally substituted phenyl, cyano or nitro or where the radicals R ⁵ and R ⁶ together with the nitrogen atom enclosed by them form a 4- to 8-membered ring, Y ¹ represents fluorine, chlorine, bromine or iodine and

Y ^{2 represents} fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl. Substituted 2-arylpyrroles of the general formula (I) according to Claim 1, in which R ^{1 represents} cyano or nitro,

R ² for the residues .

in which

X ¹ , X ² , X ³ and X ^{4 may be the} same or different and represent hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl

stand,

R ^{3 represents} hydrogen, phenyl or C ₁ -C ₆ alkyl, which is optionally substituted by 1 to 5 fluorine and / or chlorine atoms, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, (C ₁ -C _4- alkyl) carbonyloxy, (C ₁ -C ₄ -alkoxy) carbonyl, phenyl, cyano or nitro,

R ⁵ and R ^{6 are} independently hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl, the alkyl, alkenyl or

Alkynyl radicals, optionally with 1 to 5 radicals from the series fluorine, chlorine, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, (C ₁ -C ₄ -alkyl) carbonyloxy, (C ₁ -C ₄ alkoxy) carbonyl, optionally substituted phenyl, cyano or nitro are substituted, or for (C ₁ -C ₆ alkoxy) carbonyl, (C ₃ -C ₆ alkenoxy) carbonyl or ( C ₃ -C ₆ -alkinoxy) carbonyl, the alkoxy, alkenoxy or alkynoxy part optionally being 1 to 5 residues of the series

Fluorine, chlorine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -alkylthio, (C ₁ - C ₄ alkyl) carbonyloxy, (C ₁ -C ₄ alkoxy) carbonyl, optionally substituted phenyl, cyano or nitro are substituted, or stand for (C ₁ -C ₆ alkyl) carbonyl, which is optionally by 1 to

5 fluorine and / or chlorine atoms, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, (C ₁ -C ₄ alkyl) carbonyloxy, (C ₁ -C ₄ alkoxy) carbonyl, optionally substituted phenyl , Cyano or nitro, or where the radicals R ⁵ and R ⁶ together with the nitrogen atoms enclosed by them form a 4- to 6-membered ring,

Y ^{1 represents} chlorine or bromine and

Y ^{2 represents} chlorine, bromine or CF ₃ .

4. Process for the preparation of substituted 2-arylpyrroles of the general formula (I)

in which

R ^{1 represents} cyano or nitro,

R ² for the residues

.

in which

X ¹ , X ² , X ³ and X ^{4 may be the} same or different and represent hydrogen, halogen or alkyl,

R ⁴ stands for Haloαen and n stands for a number from 0 to 3

R ^{3 represents} hydrogen, phenyl or optionally substituted alkyl,

R ⁵ and R ⁶ independently of one another for hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxycarbonyl, alkenoxy carbonyl, alkynoxycarbonyl, alkylcarbonyl or where the radicals R ⁵ and R ⁶ together with the nitrogen atom enclosed by them form a Cylcus, Y ¹ for halogen and

Y ^{2 represents} halogen, alkyl or haloalkyl, characterized in that

2-arylpyrroles of the formula (II)

in which

R ¹ , R ² , Y and Y ^{2 have} the meaning given above, with compounds of the formula (III)

in which

R ³ , R ⁵ and R ^{6 have} the meaning given above and X ^{5 represents} an anionic leaving group, if appropriate in the presence of bases and / or if appropriate in the presence of diluents.

5. pesticide, characterized by a content of at least one substituted 2-arylpyrrole of the formula (I). 6. A method for controlling animal pests, characterized in that substituted 2-arylpyrroles of the formula (I) are allowed to act on animal pests and / or their habitat.

7. Use of substituted 2-arylpyrroles of the formula (I) for controlling animal pests. 8. A process for the preparation of pesticides, characterized in that substituted 2-arylpyrroles of the formula (I) are used

Extenders and / or surface-active agents mixed,