EP1305302A1 - Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides (i) - Google Patents

Abstract

The invention relates to novel heterocyclic fluoroalkenyl thioethers of formula (I) wherein X represents hydrogen, halogen or alkyl, m represents whole numbers from 2 to 10, n represents 0, 1 or 2, Y represents optionally substituted methylene and p represents 1, 2 or 3. The invention also relates to a method for the production thereof and the use of the same as pesticides.

Description

HETEROCYCLIC FLUORALKENYLTHIOETHER AND THEIR USE AS PESTICIDES (I)

The present invention relates to novel heterocyclic fluoroalkenyl thioethers, processes for their preparation and their use as pesticides.

It is known that certain heterocyclic fluoroalkenyl thioethers have insecticidal, acaricidal and / or nematicidal properties (see, for example, US 3,914,251, US 5,952,359, WO 99/52874, WO 99/52882 or JP 11140063). The effectiveness or range of action of these compounds, however, is not always entirely satisfactory, particularly at low active substance concentrations and application rates.

We have now found new heterocyclic fluoroalkenyl thioethers of the formula (I)

in which

X represents hydrogen, halogen or alkyl,

m represents integers from 2 to 10,

n represents 0, 1 or 2,

Y represents optionally substituted methylene and

p represents 1, 2 or 3.

Furthermore, it was found that the heterocyclic fluoroalkenyl thioethers of the formula (I) can be obtained if a) Mercapto derivatives of the formula (II)

in which

Y and p have the meaning given above,

with fluoroalkenyl halides of the formula (III)

in which

X and m have the meaning given above and

Shark represents halogen, preferably bromine or chlorine,

in the presence of a diluent and, if appropriate, in the presence of a basic reaction auxiliary, the compounds of the formula (II) also being able to be used in the form of their salts, preferably the alkali metal salts, such as, in particular, the sodium or potassium salts; and if necessary

b) the inventive heterocyclic fluoroalkenyl thioethers of the formula (Ia)

in which

X, Y, m and p have the meaning given above, oxidized with an oxidizing agent, optionally in the presence of a diluent and optionally in the presence of a catalyst.

Finally, it was found that the new heterocyclic fluoroalkenyl thioethers of the formula (I) have highly pronounced biological properties and, above all, for controlling animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forestry, in the protection of stocks and materials, and occur in the hygiene sector, are suitable.

Formula (I) provides a general definition of the heterocyclic fluoroalkenyl thioethers according to the invention.

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

X preferably represents hydrogen, fluorine, chlorine or bromine,

m preferably represents integers from 2 to 8.

n is preferably 0 or 2.

Y preferably represents methylene which is substituted once or twice, identically or differently, examples of which may be mentioned as substituents: in each case optionally by halogen, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -

Alkylthio, C1-C4-haloalkoxy or CrC-j-haloalkylthio substituted C ₁ -C alkyl, C ₂ -C ₄ alkenyl or C ₂ -C alkynyl; or optionally mono- to trisubstituted by identical or different substituents, wherein are exemplified as substituents: halogen, cyano, nitro, C ₁ -C ₄ alkyl, C _\ - C ₄ alkoxy, C ₁ -C alkylthio, Ci- -Halogenalkyl, CrGrHalogenalkoxy or

-C ^ haloalkylthio. p is preferably 1 or 2.

X particularly preferably represents hydrogen or fluorine,

m particularly preferably represents integers from 2 to 6.

n particularly preferably represents 0.

Y particularly preferably represents methylene which is monosubstituted or disubstituted, identically or differently substituted, examples of which may be mentioned as substituents: C ₁ -C ₄ -alkyl or phenyl which is monosubstituted or disubstituted, identically or differently, examples of which are mentioned: halogen , Cyano, nitro, C ₁ -C ₂ alkyl, -Ca alkoxy, C ₁ -C ₂ alkylthio, C ₁ -C ₂ haloalkyl, Ci-C ₂ haloalkoxy or CrC ₂ -

Halogenoalkylthio.

p particularly preferably represents 1.

X very particularly preferably represents fluorine.

m very particularly preferably represents 2 or 4.

Y very particularly preferably represents methylene which is monosubstituted or disubstituted by the same or different substituents, examples of which may be mentioned as substituents: methyl, ethyl or phenyl which is monosubstituted or disubstituted by the same or different substitution, examples of which are mentioned: fluorine, chlorine, Methyl, methoxy, trifluoromethyl, cyano or nitro. From the meanings given as preferred, particularly preferred or very particularly preferred, compounds of the formula (I) in which

X represents hydrogen or fluorine,

m represents 2 or 4,

n represents 0, 1 or 2,

Y represents methylene optionally substituted once or twice, identically or differently by methyl or ethyl, or represents phenyl optionally substituted once or twice, identically or differently by fluorine, chlorine, methyl, methoxy, trifluoromethyl, cyano or nitro, and

p represents 1, 2 or 3.

The general definitions or explanations of residues or explanations listed 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, i.e. 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 above-mentioned (preferred) requirements.

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. According to the invention, very 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 listed above and below, hydrocarbon radicals, such as alkyl - are also straight-chain or branched as far as possible, even in compounds with heteroatoms such as alkoxy.

If, for example, the sodium salt of 5-mercapto-l, 3,4-dithiazoline-3,3-dioxide and 4,4,3-trifluorobut-3-enylbromide is used as starting materials, the course of the reaction of process (a) according to the invention can be carried out by the following formula scheme can be reproduced:

If, for example, 5- (4,4,3-trifluorobutenylthio) -1, 3,4-dithiazoline-3,3-dioxide is used as the starting material and H ₂ O ₂ as the oxidizing agent and sodium tungstate as the catalyst, the course of the reaction of the process according to the invention ( b) are represented by the following formula:

Formula (II) provides a general definition of the mercapto derivatives to be used as starting materials for carrying out process (a) according to the invention.

Some of the mercapto derivatives of the formula (II) are known and / or can be prepared analogously to known processes (see, for example, Angew. Chemie 74, 874 (1962); Bull. Chem. Soc. Japan 45, 1567 (1972) ; WO 98/29400 and the manufacturing examples).

Not yet known and also the subject of the present application are the mercapto derivatives of the formula (Ha)

in which

Y has the meaning given above.

The mercapto derivatives of the formula (Ha) are obtained in a generally known manner by, for example, halogen sulfonamides of the formula (IV) known in a first stage Hal ^, - (Y) ₃ -SO ₂ -NH ₂ (IV)

in which

Shark ^{1 represents} halogen, preferably chlorine and

Y has the meaning given above,

first reacted with carbon disulphide (CS ₂ ) in the presence of a diluent such as dimethylformamide and in the presence of a basic reaction auxiliary such as sodium hydroxide and then alkylated with a reaction auxiliary such as dimethylformamide, and then in a second stage the new 1,4s formed , 2-dithiazepine-l, l-dioxide of the formula (V)

in which

R is C ₁ -C - alkyl, preferably methyl and

Y has the meaning given above,

reacted with sulfuryl chloride and finally in a third stage the new 3-chloro-l, 4,2-dithiazepine-l, l-dioxide of the formula (VI)

in which Y has the meaning given above,

by means of alkali hydrogen sulfides, e.g. Sodium bisulfide in the presence of a diluent, e.g. Dioxane, optionally in a mixture with water, is converted into the mercapto derivatives of the formula (Ila) (cf. also the preparation examples). In certain cases it may be advantageous to isolate the mercapto derivatives of the formula (Ila) directly within the first step.

Formula (III) provides a general definition of the fluoroalkenyl halogens to be used as starting materials in process (a) according to the invention. The

Fluoroalkenyl halides of the formula (III) are known (see, for example, J. Chem. Soc. Perkin Trans. 2, 219 (1998); Tetrahedron Lett. 37, 5321 (1996); EP 0 334 796 or WO 95/4727) or commercially available.

Inert organic solvents are suitable as diluents for carrying out process (a) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, anisole, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, ether such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, ketones such as acetone or butanone, nitriles such as acetonitrile or propionitrile, amides such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorus- such as ethyl acetate, sulfoxides such as dimethyl sulfoxide or sulfolane, but also alcohols such as methanol, ethanol or isopropanol.

Process (a) according to the invention can, if appropriate, be carried out in the presence of a basic reaction auxiliary. All conventional inorganic or organic bases are suitable as such. These include, for example, alkali metal and alkaline earth metal hydroxides, such as sodium hydroxide, potassium hydroxide or calcium hydroxide, alkali metal carbonates or hydrogen carbonates, such as Sodium carbonate, potassium carbonate, cesium carbonate or sodium bicarbonate and tertiary amines, such as triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and + 200 ° C, preferably at temperatures between + 20 ° C and + 140 ° C.

To carry out process (a) according to the invention, 0.3 to 3.0 mol, preferably a slight excess, of fluoroalkenyl halide of the formula (III) and, if appropriate, 0.5 to 2, are generally employed per mol of mercapto derivative of the formula (II) , 0 moles, preferably 0.5 to 1.0 mole of reaction auxiliary. The reaction, working up and isolation of the reaction products is carried out according to generally customary methods.

Suitable oxidizing agents for carrying out process (b) according to the invention are all customary oxidizing agents which can be used for sulfur oxidation. Hydrogen peroxide, organic peracids such as peracetic acid, m-chloroperbenzoic acid, p-nitroperbenzoic acid or atmospheric oxygen are particularly suitable.

Inert organic solvents are also suitable as diluents for carrying out process (b) according to the invention. It is preferred to use hydrocarbons such as gasoline, benzene, toluene, hexane or petroleum ether, chlorinated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene, ethers such as diethyl ether, dioxane or tetrahydrofuran, carboxylic acids such as acetic acid or Propionic acid, or dipolar aprotic solvents such as acetonitrile, acetone, ethyl acetate or dimethylformamide. If appropriate, process (b) according to the invention can be carried out in the presence of a suitable catalyst. All metal salt catalysts customarily used for such sulfur oxidations are suitable as such. Examples include ammonium molybdate and sodium tungstate.

The reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between -20 ° C and + 70 ° C, preferably at temperatures between 0 ° C and + 50 ° C.

To carry out process (b) according to the invention, 0.8 to 1.2 mol, preferably equimolar amounts, of oxidizing agent are generally used per mole of compound of the formula (Ia) if the oxidation of the sulfur is carried out on the

Wants to interrupt the sulfoxide stage. For oxidation to the sulfone, 1.8 to 3.0 mol, preferably double molar amounts, of oxidizing agent are generally used per mol of compound of the formula (Ia). The reaction, work-up and isolation of the end products is carried out by customary methods known to those skilled in the art.

With good plant tolerance and favorable warm-blood toxicity, the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. The active ingredients are particularly suitable for controlling nematodes. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include: 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 spp ..

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

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. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.

From the order of the Blattaria e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.

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 Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.

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, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigususpp. Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus s.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius,

Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxiaothpppp., Brassica. Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretaella retina, Cacoeciaiaanaana pellaellaiaanaella pia , Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephususpp sulcatus, Cosmopolites sordidus,

Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Agribiole spp., Tenebrio molitor. Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus. From the order of the Hymenoptera, for example 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., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp ..

From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..

From the class of the Arachnida e.g. Scorpio maurus, Latrodectus mactans, 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., Hemitarsonemus spp., Brevipalpus spp ..

Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.

The compounds of the invention can be particularly successful

Control of nematodes harmful to plants, e.g. against Meloidogyne incognita larvae, but also for combating plant-damaging insects, e.g. against the peach aphid (Myzus persicae), the larvae of the horseradish beetle (Phaedon cochleariae) as well as against the caterpillars of the army worm (Spodoptera frugiperda) and for combating plant-damaging spider mites

(Tetranychus urticae). When applied in appropriate amounts, the compounds according to the invention also show fungicidal properties, in particular against Pyricularia.

If appropriate, the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungal agents and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.

According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossing or protoplast fusion, are treated. In a further preferred embodiment, transgenes are

Plants and plant varieties, if necessary by genetic engineering methods obtained in combination with conventional methods (Genetic Modified Organisms) and their parts treated. The term "parts" or "parts of plants" or "plant parts" was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or expansions of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance , easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products possible, which go beyond the effects to be expected.

The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting,

Acceleration of ripeness, higher crop yields, higher quality and / or higher Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted. The traits are particularly emphasized as the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CryIA (b), CryΙA (c), CrylLA, CryπiA, CryiπB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). As properties

("Traits") are also particularly emphasized the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. The properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene), the genes which confer the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are corn varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YTELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn) , StarLink® (e.g. maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).

Examples of herbicide-tolerant plants are maize, cotton and

Soybeans known as Roundup Ready® (Tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas e.g. corn). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize).

Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").

The plants listed can be particularly advantageous according to the invention with the

Compounds of the general formula I or the active compound mixtures according to the invention are treated. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, impregnated with active ingredients

Natural and synthetic substances as well as very fine encapsulation 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 solid carriers, if appropriate using surface-active agents. thus emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as 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.

The following are suitable as solid carriers:

e.g. Ammonium salts and 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 are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho- lipids such as cephalins and lecithins and synthetic phosphophides. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

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

The active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.

Particularly cheap mixing partners are e.g. the following:

fungicides:

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,

Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,

Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvon,

Quinomethionate (quinomethionate), chlobenthiazon, chlorfenazole, chloroneb, chloro- picrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimiethirimol, dimethomorph, diniconazole,

Diniconazol-M, Dinocap, Diphenyla in, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxolon,

Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,

Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusilazolutolol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis,

Furmecyclox,

guazatine,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, Imibenconazol, Iminoctadin, hninoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Jrumamycin, Isoprothiolan, Isovaledione,

Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,

Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb,

Propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

Quinconazole, quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, dioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutichl, triazoxid, triazoxid, triazoxid, triazoxide

Tridemorph, triflumizole, triforin, triticonazole,

uniconazole

Validamycin A, vinclozolin, viniconazole,

Zarilamid, Zineb, Ziram as well

Dagger G,

OK 8705, OK 8801,

α- (l, l-dimethylethyl) -S-S- (2-phenoxyethyl) -lH-l, 2,4-triazol-l-ethanol,

- (2,4-Dichlθφhenyl) -beta-fluoro-.beta.-propyl-lH-l, 2,4-triazol-l-ethanol,

α- (2,4-dichlorophenyl) -beta-methoxy-α-methyl-lH-l, 2,4-triazol-l-ethanol,

α- (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH-l, 2,4-triazol-1-ethanol,

(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (lH-l, 2,4-triazol-l-yl) -3-octanone,

(E) - α- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,

{2-Methyl-1 - [[[1 - (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester

l- (2,4-dichlorophenyl) -2- (lH-l, 2,4-triazol-l-yl) -ethanone-O- (phenylmethyl) oxime,

l- (2-methyl-l-naphthalenyl) -lH-pyrrole-2,5-dione,

l- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,

l - [(diiodomethyl) sulphonyl] -4-methylbenzene,

l - [[2- (2,4-dichlorophenyl) -l, 3-dioxolan-2-yl] methyl] -lH-imidazole,

l - [[2- (4-chlorophenyl) -3-ρhenyloxiranyl] methyl] -lH-l, 2,4-triazole, l- [l- [2 - [(2,4-Dichlθφhenyl) methoxy] phenyl] ethenyl] -lH-imidazole,

1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4 ^, -trifluoromethyl-1, 3-thiazole-5-carboxanilide,

2,2-DicUor-N- [l- (4-cMoφhenyl) ethyl] -l-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-DicMor-5- (methylthio) -4-pyrimidinyl thiocyanate,

2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide,

2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,

2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,

2 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1, 3,4-thiadiazole,

2 - [[6-Deoxy-4-O- (4-O-methyl-ß-D-glycopyranosyl) -α-D-glucopyranosyl] amino] -4-methoxy-lH-pyrrolo [2,3-d] pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2- (bromomethyl) -pentandinitril,

2-chloro-N- (2,3-dmydro-l, l, 3-trimethyl-lH-mden-4-yl) -3-pyridine carboxamide,

2-CUor-N- (2,6-dimethylphenyl) -N- (isot ocyanatomethyl) acetamide,

2-phenylphenol (OPP), 3,4-dichloro-l- [4- (difluoromethoxy) phenyl] -lH-pyrrole-2,5-dione,

3,5-dic or-N- [cyan [(l-memyl-2-proρvnyl) -oxy] -memyl] -benzamide,

3 - (1, 1-dimethylpropyl) - 1-oxo-lH-indene-2-carbonitrile,

3- [2- (4-Chloφhenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine,

4-C or-2-cyan-N, N-dimethyl-5- (4-methylρhenyl) -lH-imidazole-l-sulfonamide,

4-methyl-tetrazolo [l, 5-a] quinazolin-5 (4H) -one,

8- (l, l-dimethylethyl) -N-ethyl-N-propyl-l, 4-dioxaspiro [4.5] decane-2-methanamine,

8-hydroxyquinoline sulfate,

9H-xanthene-9-carboxylic acid-2- [φhenylamino) carbonyl] hydrazide,

bis- (l-Methylemyl) -3-memyl-4 - [(3-methylbenzoyl) oxy] -2,5-thiophene dicarboxylate,

cis-l- (4-Chloφhenyl) -2- (lH-l, 2,4-triazol-l-yl) cycloheptanol,

cis-4- [3- [4- (l, l-dimethylpropyl) phenyl-2-memylpropyl] -2,6-dimethyl-moφholin hydrochloride,

Ethyl - [(4-chloφhenyl) azo] cyanoacetate,

Kaliurnhydrogencarbonat,

Methantetrathiol sodium salt, Methyl l- (2,3-d dro-2,2-dime l-lH-mden-l-yl) -lH-imidazole-5-carboxylate,

Methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,

Memyl-N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,

N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide.

N- (2,6-Dirnethylphenyl) -2-methoxy-N- (tefrahydro-2-oxo-3-fiιranyl) -acetamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tefrahydro-2-oxo-3-tMenyl) -acetamide,

N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,

N- (4-Cyclohexyl-phenyl) -l, 4,5,6-tefrahydro-2-pyrimidineamine;

N- (4-hexylphenyl) -l, 4,5,6-tefrahydro-2-pyrimidineamine;

N- (5-chloro-2-memylphenyl) -2-memoxy-N- (2-oxo-3-oxazolidmyl) -acetamide,

N- (6-Memoxy) -3-pyridinyl) -cyclopropanecarboxamide,

N- [2,2,2-TricMor-l - [(chloroacetyl) -amino] -ethyl] -benzamide,

N- [3-CMor-4,5-bis (2-propmyloxy) phenyl] -N ^, -memoxy-memanimidamide,

N-fonnyl-N-hydroxy-DL-alanine sodium salt,

O, O-diethyl [2- (ώpropylamino) -2-oxoemyl] -emylphosphoramidothioat,

O-methyl-S-phenyl-phenylpropylphosphoramidothioat, S-methyl-1, 2,3-benzothiadiazole-7-carbothioate,

spiro [2H] -1-benzopyran-2, 1 '(3'H) -isobenzofuran] -3'-one.

bactericides:

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

Insecticides / acaricides / nematicides:

Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin,

Azamethiphos, Azinphos A, Azinphos M, Azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin

Biopermethrin, Bistrifluoron, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butylpyridaben,

Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron,

Chlormephos, Chloφyrifos, Chloφyrifos M, Chlovaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Clothianidine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cyphrinine Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazmon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,

Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp.,

Eprinomectin, Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,

Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate,

Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenoxuron, Flumethrin, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb,

granulosis

Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,

Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin, IKI 220,

nucleopolyhedroviruses

Lambda cyhalothrin, lufenuron

Malathion, mecarbam, metaldehyde, methamidophos, metharhilic anisopliae,

Metharhilicium flavoviride, methidathione, methiocarb, methomyl, methoprene, methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, monocrotophos,

Naled, Nitenpyram, Nithiazine, Novaluron Omethoate, Oxamyl, Oxydemethon M

Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pymetroz

Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxyfen,

quinalphos,

ribavirin

Salithion, Sebufos, Selamectin, Silafluofen, Spinosad, Spirodiclofen, Sulfotep, Sulprofos, S 1812,

Tau fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Theta-cyper-methhrin, Thiacloprid, Thiamethoxam, Thiapronilarbox, Thiapronilarbox, Thiapronilarbox, Thiapronil, Oxi Triarathenes, triazamates, triazophos, triazuron, trichlophenidines, trichlorfon,

Triflumuron, trimethacarb,

Vamidothion, Vaniliprole, Verticillium lecanii

YI 5302

Zeta-cypermethrin, zolaprofos

(IR-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropanecarboxylate (3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylat

l - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-l, 3,5-triazin-2 (1H) - imine

2- (2-chloro-6-fluoφhenyl) -4- [4- (l, l-dimethylethyl) phenyl] -4,5-dihydro-oxazol

2- (Acetlyoxy) -3-dodecyl-l, 4-naphthalenedione

2-Chloro-N - [[[4- (l -phenylethoxy) phenyl] amino] carbonyl] benzamide

2-chloro-N - [[[4- (2,2-dichloro-l, l-difluoroethoxy) -phenyl] -amino] -carbonyl] -benzamide

3-methylphenyl propylcarbamate

4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene

4-Chloro-2- (l, 1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone

4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) -pyridazinone

4-Chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3, 4-dichloφhenyl) -3 (2H) -pyridazinone

Bacillus thuringiensis strain EG-2348

Benzoic acid [2-benzoyl-1 - (1, 1-dimethylethyl) hydrazide

Butanoic acid 2,2-dimethyl-3 - (2,4-dichloφhenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester [3 - [(6-chloro-3-pyridinyl) methyl] -2-t azolidinylidene] cyanamide

Dihydro-2- (nitromethylene) -2H- 1,3-thiazine-3 (4H) -carboxaldehyde

Ethyl [2 - [[l, 6-dihydro-6-oxo-l- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate

N- (3,4,4-trifluoro-1-oxo-3-butenyl) glycine

N- (4-Chloφhenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-lH-pyrazol-

1-carboxamide

N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine

N-methyl-N '- (1-methyl-2-propenyl) - 1, 2-hydrazinedicarbothioamide

N-methyl-N'-2-propenyl-1, 2-hydrazine dicarbothioamide

O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat

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

When used as insecticides, the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The drug concentration of the Application forms can be from 0.0000001 to 95% by weight of active compound, 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 pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.

The active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. These parasites include:

From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..

From the order of the Mallophagida and the subordinates Amblycerina as well

Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..

From the order Diptera and the subordinates Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp.,

Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp ., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora 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 Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..

From the order of the Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp.,

Panstrongylus spp ..

From the order of the Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp ..

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietssus spp., ., Stemostoma spp., Varroa spp ..

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp., Chorioptes 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 controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats,

Horses, pigs, donkeys, camels, buffaloes, 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. Fighting these arthropods is said to result in deaths and reduced performance (in meat, milk, wool, skins, eggs, honey, etc.) be reduced, so that more economical and simple animal husbandry is possible through the use of the active compounds according to the invention.

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, watering, drenching, granules, pastes, boluses, the feed-through method, of suppositories, by parenteral administration, such as 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), des

Washing, powdering and with the help of shaped bodies containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.

When used for cattle, poultry, pets etc., you can use the active ingredients in

Use formula (I) as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10,000 times dilution, or use them as a chemical bath.

With favorable warm-blood toxicity, the agents according to the invention are suitable for combating pathogenic endoparasites which occur in humans and in animal husbandry and animal breeding in farm animals, breeding, zoo, laboratory, experimental and hobby animals. They are effective against all or individual stages of development of the pests and against resistant and normally sensitive species. By fighting the pathogenic

Endoparasites are said to reduce illness, deaths and impaired performance (e.g. in the production of meat, milk, wool, hides, eggs, honey, etc.), so that the use of the active ingredients enables more economical and easier animal husbandry. Pathogenic endoparasites include cestodes, trematodes, nematodes, acantocephals in particular: From the order of the Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diphlogonoporus spp ..

From the order of the Cyclophyllidea, for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomsa spp., Thysaniezia spp., Avitelellina spp., Stilesia spp., Cittotaenia spp., Andyella spp., Bertella spp spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplop. ,

From the subclass of Monogenea e.g. Gyrodactylus spp., Dactylogyrus spp., Polystoma spp ..

From the subclass of Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinopin spp., Echinopin spp., Hypoderaeum spp., Fasciola spp Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp Paramphistomum spp., Calicophoron spp-, Cotylophoron spp., Gigantocotyle spp, Fischor. sppyl., sppyl. Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., CoUyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp ..

From the order of the Enoplida, for example: Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp ..

From the order of the Rhabditiaz.B .: Micronema spp., Strongyloides spp ..

From the order of the Strongylida, e.g .: Stronylus spp., Triodontophorus spp.,

Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cyhcostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamususpppp., Cyastostong spp. Dictyocaulus spp., Muellerius spp., Protostrongylus spp. Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus sp

Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp. Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Cooperagia spp., Marshallagia spp., Marshallagia spp. Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp ..

From the order of the Oxyurida, for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp ..

From the order of Ascaridia, for example: Ascaris spp., Toxascaris spp., Toxocara spp.,

Parascaris spp., Anisakis spp., Ascaridia spp ..

From the order of the Spimrida, for example: Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp ..

From the order of the Filariida, for example: Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp ..

From the order of the Gigantorhynchida, for example: Filicollis spp., Moniliformis spp., Macracanthorhynchus spp., Prosthenorchis spp ..

Livestock and breeding animals include mammals such as Cattle, horses, sheep, pigs, goats, camels, water buffalos, donkeys, rabbits, fallow deer, reindeer,

Fur animals such as mink, chinchilla, raccoon, birds such as chickens, geese, turkeys, Ducks, ostriches, fresh and saltwater fish such as trout, beef, eels, reptiles, insects such as honeybees and silkworms.

Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters, dogs and cats.

The pets include dogs and cats.

The application can be prophylactic as well as therapeutic.

The active ingredients are used directly or in the form of suitable preparations enterally, parenterally, dermally, nasally, by treating the environment or with the aid of shaped bodies containing the active ingredient, e.g. Strips, plates, ribbons, collars, ear tags, limb straps, marking devices.

The enteral application of the active ingredients takes place e.g. orally in the form of powder, tablets, capsules, pastes, drinkers, granules, orally applicable solutions, suspensions and emulsions, boluses, medicated feed or drinking water. The dermal application happens e.g. in the form of diving (dipping), spraying (spraying) or pouring on (pour-on and spot-on). Parenteral use happens e.g. in the form of injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or by implants.

Suitable preparations are:

Solutions such as solutions for injection, oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, infusion formulations, gels;

Emulsions and suspensions for oral or dermal use and for injection; semi-solid preparations; Formulations in which the active ingredient is processed in an ointment base or in an oil in water or water in oil emulsion base;

Solid preparations such as powders, premixes or concentrates, granules, pellets,

Tablets, boluses, capsules; Aerosols and inhalants, shaped bodies containing active ingredients.

Solutions for injection are administered intravenously, intramuscularly and subcutaneously.

Injection solutions are made by adding the active ingredient in a suitable

Solvent is dissolved and additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives may be added. The solutions are sterile filtered and filled.

The following may be mentioned as solvents: Physiologically compatible solvents such as

Water, alcohols such as ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, and mixtures thereof.

If appropriate, the active compounds can also be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

The following may be mentioned as solubilizers: solvents which promote the dissolution of the active ingredient in the main solvent or prevent its precipitation. Examples are polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.

Preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol.

Oral solutions are applied directly. After prior dilution to the application concentration, concentrates are used orally. Oral solutions and Concentrates are produced as described above for the injection solutions, whereby sterile work can be dispensed with.

Solutions for use on the skin are dripped on, spread on, rubbed in, sprayed on or sprayed on. These solutions are prepared as described above for the injection solutions.

It may be advantageous to add thickeners during manufacture. Thickeners are: inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as cellulose derivatives,

Polyvinyl alcohols and their copolymers, acrylates and metacrylates.

Gels are applied or spread on the skin or placed in body cavities. Gels are made by adding enough thickening agent to solutions that have been prepared as described for the injection solutions to form a clear mass with an ointment-like consistency. The thickeners specified above are used as thickeners.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active ingredient penetrating the skin and acting systemically.

Pour-on formulations are prepared by dissolving, suspending or emulsifying the active ingredient in suitable solvents or solvent mixtures that are compatible with the skin. If necessary, other auxiliaries such as dyes, absorption-promoting substances, antioxidants, light stabilizers and adhesives are added.

The following may be mentioned as solvents: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerin, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol, mono-butyl glycol, mono Acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-methylpyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane.

Dyes are all dyes approved for use on animals, which can be dissolved or suspended.

Substances that demand resorption are e.g. DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.

Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid,

Butylated hydroxytoluene, butylated hydroxyanisole, tocopherol.

Light stabilizers are e.g. Novantisol acid.

Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.

Emulsions can be used orally, dermally or as injections.

Emulsions are either water in oil or oil in water.

They are produced by dissolving the active ingredient either in the hydrophobic or in the hydrophilic phase and homogenizing it with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as dyes, absorption-enhancing substances, preservatives, antioxidants, light stabilizers, viscosity-increasing substances ,

The following may be mentioned as hydrophobic phase (oils): paraffin oils, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric acid biglyceride, triglyceride mixture with vegetable fatty acids of chain length

C _8-1 or other specially selected natural fatty acids, partial glyceride Mix saturated or unsaturated, possibly also hydroxyl-containing fatty acids, mono- and diglycerides of Cg / Cio fatty acids.

Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, lauric acid hexyl ester, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length ₆ -C ₈ , isopropyl myristate, isopropyl palmitate, caprylic / capric alcohol ester of the saturated fatty length ₁₂ - C ₁₈ , isopropyl stearate, oleic acid oleyl ester, oleic acid decyl ester, ethyl oleate, lactic acid ethyl ester, waxy fatty acid esters such as artificial duckling gland fat, dibutyl phthalate, adipic acid diisopropyl ester, the latter related ester mixtures and others

Fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.

Fatty acids such as Oleic acid and its mixtures.

The following can be mentioned as the hydrophilic phase:

Water, alcohols such as e.g. Propylene glycol, glycerin, sorbitol and their mixtures.

The following may be mentioned as emulsifiers: nonionic surfactants, e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;

ampholytic surfactants such as di-Na-N-lauryl-β-iminodipropionate or lecithin;

anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether morphophosphate monoemanolamine salt;

cationic surfactants such as cetyltrimemylammonium chloride. Other auxiliaries that may be mentioned are: viscosity-increasing and emulsion-stabilizing substances such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes , colloidal silica or mixtures of the listed substances.

Suspensions can be used orally, dermally or as an injection. They are produced by adding the active ingredient in a carrier liquid, if necessary with the addition of other auxiliaries such as wetting agents, dyes, substances requiring resorption,

Preservatives, antioxidants, sunscreen suspended.

All homogeneous solvents and solvent mixtures may be mentioned as carrier liquids.

The surfactants specified above may be mentioned as wetting agents (dispersants).

Further additives mentioned are those mentioned above.

Semi-solid preparations can be administered orally or dermally. They differ from the suspensions and emulsions described above only in their higher viscosity.

To prepare solid preparations, the active ingredient is mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape.

All physiologically compatible solid inert substances may be mentioned as carriers. Inorganic and organic substances serve as such. Inorganic substances are e.g. Common salt, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides,

Silicas, clays, precipitated or colloidal silicon dioxide, phosphates. Organic substances are, for example, sugar, cellulose, food and feed such as milk powder, animal meal, cereal flour and meal, starches.

Excipients are preservatives, antioxidants, dyes, which have already been listed above.

Other suitable auxiliaries are lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decaying substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinyl pyrrolidone as well as dry binders such as microcrystalline cellulose.

The active substances can also be present in the preparations as a mixture with synergists or with other active substances which act against pathogenic endoparasites. Such

Active ingredients are e.g. L-2,3,5,6-tetrahydro-6-phenyl-imidazothiazole, benzimidazole carbamate, pyrantel.

Ready-to-use preparations contain the active ingredients in concentrations of 10 ppm to 20 percent by weight, preferably 0.1 to 10 percent by weight.

Preparations which are diluted before use contain the active compounds in concentrations of 0.5-90% by weight, preferably 5 to 50% by weight.

In general, it has proven advantageous to use amounts of the inventive

Mixture of about 10 to about 100 mg of active ingredient per kg of body weight per day to achieve effective results. 10 to 50 mg of active compound mixture per kg of body weight are preferred. The compositions generally maintain a weight ratio of praziquantel or epsiprantel to depsipeptide, such as 1 to 1 to 10, preferably 1 to 1 to 2, very particularly preferably 1 to 1.

It has also been found that the compounds according to the invention have a high insecticidal action against insects which destroy industrial materials.

The following insects may be mentioned by way of example and preferably, but without limitation:

Beetle like

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Emobius mollis, Priobium caφini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis,

Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleboms 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 like

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails such as Lepisma saccharina. In the present context, technical materials are to be understood as non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, 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:

Lumber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wooden products that are generally used in house construction or joinery.

The active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellant, optionally siccatives and UV stabilizers and, where appropriate, dyes and pigments and 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 occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.

An organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility 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 oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.

Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, Teφentinöl and Like. Used.

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 locker oil and / or monochlomaphthalene, preferably α-monochlomaphthalene, are used. The organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above

30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, part of the organic chemical solvent or solvent mixture is replaced by a polar organic chemical solvent or solvent mixture. Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.

In the context of the present invention, the organic-chemical binders which are known are water-dilutable and / or synthetic resins which are 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 I den coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or Resin used.

The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellents, odor correctors and

Inhibitors or anticorrosive 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 the organic chemical binder. Alkyd resins having an oil content of more than 45% by weight, preferably 50 to, are preferred according to the invention

68% by weight.

All or part of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 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 glycerol or glycerol ether - Kolether, 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, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.

A particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.

The ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides. The insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners. The compounds mentioned in this document are an integral part of the present application.

Insecticides such as chlorophyros, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthron, trifluoropuron, methifluoropuron, methifluoropuron, methifluoropuron

as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro - octylisothiazolin-3-one.

At the same time, the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.

Overgrowth by sessile oligochaetes, such as lime tube worms, and by mussels and species from the group Ledamoφha (barnacles), such as various types of Lepas and Scalpellurn, or by species from the group Balanomoφha (barnacles), such as Baianus or Pollicipes species, increases the frictional resistance of Ships and subsequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.

In addition to fouling by algae, for example Ectocaφus sp. and Ceramium sp., vegetation by sessile Entomostraken groups, which are grouped under the name Cirripedia (tendril crayfish), is particularly important. It has now surprisingly been found that the compounds according to the invention, alone or in combination with other active ingredients, have an outstanding antifouling effect.

By using compounds according to the invention alone or in combination with other active ingredients, the use of heavy metals such as e.g. in bis- (trialkyltin) sulfides, tri-ra- butyltin laurate, tri-fl-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-butyl (2-phenyl-4-chlθφhenoxy) tin, tributyltin oxide, molybdenum disulfide , antimony oxide, polymeric butyl titanate, phenyl-fbispyridin) - bismuth chloride, tri - "- butylzinnfluorid, Manganethylenbisthiocarbamat, zinc dimethyldithiocarbamate, Zinkethylenbisthiocarbamat, zinc and copper salts of 2 Pyridinthiol- 1 oxide, Bisdimethyldithiocarbamoylzinkethylenbisthiocarbamat, zinc oxide, copper (I) -ethylene bisdithiocarbamate, copper thiocyanate, copper phthalate and tributyltin halides are omitted or the concentration of these

Connections are significantly reduced.

The ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.

Suitable combination partners for the antifouling agents according to the invention are preferably:

Algicides like

2-tert-Bu1ylarnino-4-cyclopropylamino-6-methyltlιio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

Fungicides like

Benzo [b] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanide, fluorine folpet, 3-iodo-2-propynyl butyl carbamate, tolyl fluanide and azoles such as

Azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole;

Molluscicides like

Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb;

or conventional anti-fouling agents such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridine thiol-l-oxide, pyridine triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2,4,5, 6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2 , 4,6-Trichloφhenylmaleinimid.

The antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.

The antifouling agents according to the invention furthermore contain the usual ones

Components such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.

In addition to the algicidal, fungicidal, molluscicidal and insecticidal active compounds according to the invention, antifouling paints contain in particular binders.

Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, especially in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, dry oils such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.

Paints may also contain inorganic pigments, organic

Pigments or dyes, which are preferably insoluble in sea water. Paints may also contain materials such as rosin to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers that affect the rheological properties, and other conventional ingredients. Also in self-polishing antifouling

The compounds according to the invention or the abovementioned mixtures can be incorporated into systems.

The active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins and others. occurrence.

To control these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products.

They are effective against sensitive and resistant species and against all stages of development. These pests include:

From the order of the Scoφionidea e.g. Buthus occitanus.

From the order of the Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat,

Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.

From the order of the Araneae, for example Aviculariidae, Araneidae. From the order of the Opiliones, for example Pseudoscoφiones chelifer, Pseudoscoφiones cheiridium, Opiliones phalangium.

From the order of the Isopoda e.g. Oniscus asellus, Porcellio scaber.

From the order of the Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..

From the order of the Chilopoda e.g. Geophilus spp ..

From the order of the Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina,

Lepismodes inquilinus.

From the order of the Blattaria e.g. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa,

Supella longipalpa.

From the order of the Saltatoria e.g. Acheta domesticus.

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

From the order of the Isoptera e.g. Kalotermes spp., Reticulitermes spp.

From the order of the Psocoptera e.g. Lepinatus spp., Liposcelis spp.

From the order of the Coleptera e.g. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inteφunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.

From the order of the Siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.

From the order of the Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.

From the order of the anoplura e.g. Pediculus humanus capitis, Pediculus humanus coφoris, Phthirus pubis.

From the order of the Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

The application in the field of household insecticides is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, growth regulators or active ingredients from other known classes of insecticides.

They are used in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggels, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive evaporation systems, moth papers, moth bags and

Moth angels, as granules or dusts, in lures or bait stations. Preparation Examples

Example 1:

(Method a)

3.8 g (20 mmol) of sodium salt of 5-mercapto-l, 3,4-dithiazoline-3,3-dioxide and 5 g (26.5 mmol) of 4,4,3-trifluorobut-3-enyl bromide are dissolved in 30 ml of acetonitrile with 3.3 g (10 mmol) of cesium carbonate are heated to reflux with stirring for 6 hours. The reaction mixture is then poured onto water and the product is extracted with methylene chloride. After the solvent has been removed in vacuo, the residue (3.5 g of brown oil) is chromatographed on silica gel in the methylene chloride system.

2.0 g (36.1% of theory) of 5- (4,4,3-trifluorobutenylthio) -1, 3,4-dithiazoline-3,3-dioxide are obtained as yellowish crystals with a melting point of 50 ° C.

The compounds of the formula (I) given in Table 1 below are obtained analogously to Example 1 or according to the general information on the preparation:

Table 1

Example - -00p- n m X Melting (° C)

No. or logP (pH2)

2 -CH ₂ - 0 2 H 2.24

3 -CH ₂ - 0 4 F 2.93

4 -CH ₂ - 0 4 H 2.99

5 - (CH ₂ ) ₂ - 0 2 F 60

6 - (CH ₂ ) ₂ - 0 4 H 42

7 -CH (CH ₃ ) - 0 2 F 70

8 -CH (CH ₃ ) - 0 2 H 54

9 -CH (CH ₃ > 0 4 F 3.24

10 -CH (CH ₃ ) - 0 4 H 3.31

11 "(CH _{2) 2} - H 0 2 56

12 "(CH _{2) 2} - 0 4 F 56

13 - (CH ₂ ) ₃ - 0 2 F 92

14 - (CH ₂ ) ₃ - 0 2 H 58

15 - (CH ₂ ) ₃ - 0 4 F 68

16 - (CH _{2) 3} - H 76 0 4 Preparation of the mercapto derivatives of the formula (Ua)

The preparation of the mercapto derivatives of the formula (Ila) will be described using the synthesis of 3-mercapto-6,7-dihydro-5H-l, 4,2-dithiazepine-l, l-dioxide (H-l) as an example:

Step 1:

For the solution of 25.8 g (0.164 mol) of 3-chloropropanesulfonamide (Liebigs Ann. Chem.

657, 86 (1962)) in 150 ml of dimethylformamide, ION sodium hydroxide solution is added. 21.3 g (0.28 mol) of carbon disulfide are then slowly added dropwise with ice cooling. Then another 15 ml of ION sodium hydroxide solution are added and stirring is continued at 20 ° C. overnight. The mixture is then cooled to 5 ° C., 35.3 g (0.28 mol) of dimethyl sulfate are added and the mixture is allowed to warm to room temperature.

After stirring for 2.5 hours at room temperature, the mixture is poured onto ice water, extracted with ethyl acetate and the organic phase is washed with 10% sodium chloride solution. After drying over magnesium sulfate, the mixture is concentrated on a rotary evaporator and the oil which remains is crystallized in the acetone / dry ice bath with the addition of a little ethyl acetate.

10.5 g (35.3% of theory) of pale yellow crystals of 3-methylthio-6,7-dihydro-5H-l, 4,2-dithiazepine-l, l-dioxide with a melting point of 91 ° C. are obtained. Level 2:

10.5 g (50 mmol) of 3-methylthio-6,7-dihydro-5H-l, 4,2-dithiazepine-l, l-dioxide are mixed with 33.5 g (0.25 mol) of sulfuryl chloride at 40 for 2 hours ° C stirred, then overnight at 20 ° C. After the excess sulfuryl chloride has been removed, the residue is stirred with diisopropyl ether.

6.1 g (61% of theory) of 3-chloro-6,7-dihydro-5H-l, 4,2-dithiazepine-l, l-dioxide are obtained as white crystals with a melting point of 156 ° C.

Level 3:

To a mixture of 20 g (0.1 mol) of 3-chloro-6,7-dihydro-5H-l, 4,2-dithiazeρin-

1,1-dioxide in 185 ml of dioxane and 185 ml of water are added 14.8 g (0.2 mol) of sodium hydrogen sulfide monohydrate and stirred overnight at 20 ° C. The reaction mixture is acidified with dilute hydrochloric acid and the product extracted with dichloromethane. The organic phase is washed twice with dilute hydrochloric acid, dried over magnesium sulfate and concentrated on a rotary evaporator.

13.1 g (66.4% of theory) of 3-mercapto-6,7-dihydro-5H-l, 4,2-dithiazepine-1,1-dioxide with a melting point of 134 ° C. are obtained. applications

Example A

Meloidogyne Test

Solvent: 8 parts by weight of acetone 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.

Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larvae suspension and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots.

After the desired time, the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% effect means that the number of galls on the treated plants corresponds to that of the untreated control.

In this test, at an exemplary active ingredient concentration of 20 ppm, the compounds of Preparation Examples 1 and 2, for example, show an activity of 100%. Example B

Myzus Test

Solvent: 30 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 amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.

Cabbage leaves (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration.

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

In this test, at an exemplary active ingredient concentration of 0.1%, for example the compounds of preparation examples 2 and 4 show a kill of 100% after 6 days.

Example C

Phaedon larvae test

Solvent: 30 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 amounts of solvent and emulsifier, and the concentrate is diluted to the desired amount with water containing emulsifier

Concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.

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

In this test, at an exemplary active ingredient concentration of 0.1%, for example the compounds of preparation examples 2 and 4 show a kill of 100% after 7 days.

Example D

Spodoptera frugiperda test

Solvent: 30 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 amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.

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

In this test, at an exemplary active ingredient concentration of 0.1%, the compound of preparation example 2, for example, shows a kill of 100% after 7 days.

Example E

Tetranychus test (OP-resistant / immersion treatment)

Solvent: 30 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 amounts of solvent and emulsifier, and the concentrate is diluted to the desired amount with water containing emulsifier

Concentration.

Bean plants (Phaseolus vulgaris), which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration.

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

In this test, at an exemplary active ingredient concentration of 0.1%, the compound of preparation example 4, for example, shows a kill of 100% after 7 days.

Example F

Test with Boophilus microplus resistant (SP-resistant Parkhurst strain)

Test animals: adult sucked females

Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are made by dilution with distilled water.

10 adult Boophilus microplus res. are immersed in the drug preparation to be tested for 1 minute. After being transferred to a plastic cup and stored in an air-conditioned room, the degree of killing is determined.

100% means that all ticks have been killed; 0% means that none

Ticks were killed.

In this test, for example at an active substance concentration of 100 ppm, the compound of preparation example 2 shows a kill of 90%, the compound of preparation example 4 shows a kill of 100%.

Example G

Test with Boophilus microplus resistant (SP-resistant Parkhurst strain)

Test animals: adult sucked females

Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are made by dilution in the same solvent.

The test is carried out in 5-fold determination. 1 μl of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The active ingredient control is carried out after 7 days on the storage of fertile eggs. Eggs, whose fertility is not visible from the outside, are kept in glass tubes until larvae hatch in the climatic chamber. An effect of 100% means that no tick has laid fertile eggs.

In this test, at an exemplary active ingredient concentration of 20 ppm, e.g. the compounds of Preparation Examples 1, 2, 3 and 4 each have a kill rate of 100%). At an active ingredient concentration of 4 ppm, e.g. the compounds of Preparation Examples 1, 2, 3 and 4 each also have a kill rate of 100%. At an active ingredient concentration of 100 ppm, the compounds of Preparation Examples 6, 8, 10 and 16 also show a kill of 100%. With an active ingredient concentration of 20, 4 or 0.8 μg per animal, the compounds of preparation examples 6, 8, 10, 11, 13 and 16 likewise show a kill of

100%. Example H

Test with cat fleas / oral intake

Test animals: adults of Ctenocephalides felis

Solvent: dimethyl sulfoxide (DMSO)

To produce a suitable formulation, a suitable active ingredient solution is prepared from 20 mg of active ingredient with 1 ml of DMSO. 15 μl of this formulation are added to 3 ml of titrated bovine blood and stirred.

10 fasting adult fleas (Ctenocephalides felis, strain "Georgi") are placed in a chamber (0 3.2 cm) which is closed at the top and bottom with gauze. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the 3 ml blood drug formulation, which the

Fleas can be absorbed through the parafilm membrane. While the blood is being heated to 37 ° C, a temperature of 25 ° C is set in the area of the flob chambers. Controls are mixed with the same volume of DMSO without the addition of a compound. Triple determinations are carried out.

After 28 h, the mortality is determined in% (= dead fleas).

Compounds that achieve at least 25% flea kill within 28 hours are considered effective.

In this test, at an exemplary active ingredient concentration of 100 ppm, e.g. the compounds of Preparation Examples 2 and 4 each have a kill of 100%, the compounds of Preparation Examples 6, 8, 10 and 16 each have a kill of 95, 91, 95 and 91%. At an active ingredient concentration of 20 ppm, the present test found for the compounds of Preparation Examples 6, 8

10 and 16 kill 73, 79, 83 and 89% respectively. Example I

Test with flies (Musca domestica)

Test animals: adult Musca domestica, trunk Reichswald (OP, SP,

Carbamate resistant) Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are made by dilution with distilled water.

2 ml of this preparation of active substance are pipetted onto filter paper dishes (0 9.5 cm), which are located in Petri dishes of the appropriate size. After the filter disks have dried, 25 test animals are transferred to the Petri dishes and covered.

After 1, 3, 5, 24 and 48 hours, the effectiveness of the active ingredient preparation is determined. 100% means that all flies have been killed; 0% means that no flies have been killed.

In this test, for example, at an active substance concentration of 100 ppm, the compound of preparation example 2 shows a kill of 60%, the compound of preparation example 4 shows a kill of 40%.

Example J

Blowfly larva test (development-inhibiting effect)

Test animals: Lucϊlia cuprina larvae

Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are made by dilution with distilled water.

About 20 Luciliα cuprinα larvae are placed in a test tube which contains approx. 1 cm ³ horse meat and 0.5 ml of the active ingredient preparation to be tested. The effectiveness of the active substance preparation is determined after 24 and 48 hours. The test tubes are transferred to beakers with a sand-covered bottom. After a further 2 days, the test tubes are removed and the dolls are counted.

The effect of the active substance preparation is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched; 0% means that all flies hatched normally.

In this test, at an exemplary active ingredient concentration of 100 ppm, the compounds of Preparation Examples 1, 3, 6, 8 and 10, for example, each show a kill of 100%. At an active ingredient concentration of 20 ppm, for example, the compounds of Preparation Examples 1 and 3 likewise show a kill of 100%. Example K

Nippostrongylus brasiliensis in vitro

Test animals: Adult Nippostrongylus brasiliensis

Solvent: dimethyl sulfoxide

Nippostrongylus brasiliensis worms are isolated from the small intestine of female Wistar rats and collected in aqueous 0.9% NaCl containing 20 μg / ml sisomycin and 2 μg / ml canesten. The incubation of both worm groups (male / female sex) is carried out in 1.0 ml medium, which is used for the determination of the acetylcholinesterase activity. The incubation conditions and the determination of the enzyme activity were described in Martin et al., Pesticide Science (1996) 48, 343-349. The compounds are dissolved in the specified solvent (10 mg to 0.5 ml) and brought to the desired concentration. The controls contain only the solvent.

The vitality of the worms is characterized by the activity of acetylcholinesterase, which the worms actively secreted into the incubation medium. The classification of acetylcholinesterase activity follows the work of

Martin et al. (1996). 0 means no activity, 1 weak activity, 2 good activity and 3 full activity (<50%, 50 - 75%,> 75%, 100% enzyme inhibition).

In this test, at an exemplary active ingredient concentration of 100 ppm, e.g. the compounds of Preparation Examples 2, 4, 10, 11, 16, a weak one

Effect, the compounds of Preparation Examples 3, 6, 8 have a good effect. Example L

Trichinella spiralis in vitro

Test animals: Trichinella spiralis larvae

Solvent: dimethyl sulfoxide

Trichinella spiralis larvae are isolated from the skeletal muscles and muscles below the skin of SPF / CFW1 mice and collected in aqueous 0.9% NaCl containing 20 μg / ml sisomycin. 20 larvae in 2 ml of a

Incubated nutrient solution (20 g / 1 Bacto Casitone, 10 g / 1 yeast extract, 5 g / 1 glucose, 0.8 g / 1 KH ₂ PO ₄ , 0.8 g K ₂ HPO ₄ ; 10 g / ml sisomycin and 1 μg / ml Canesten; pH = 7.2).

Incubation and determination was described in Martin et al., Pesticide Science (1996) 48,

343-349. 10 mg of the test compound are dissolved in 0.5 ml of the specified solvent and enough of the solution obtained is added to the incubation medium such that the desired concentration is calibrated. The controls contain only the solvent.

The experiment is ended after an incubation period of 5 days at a temperature of 19 ° C. The anthelmintic activity of a substance is divided into 4 levels. 0 means no, 1 weak, 2 good and 3 full activity (<50%, 50 - 75%,> 75%, 100% of the larvae dead).

In this test, at an exemplary active ingredient concentration of 100 ppm, e.g. the compound of preparation example 3 had a weak action. The compounds of preparation examples 4, 6, 8, 10, 11 and 16 showed no effect in this test at an exemplary active compound concentration of 100 ppm.

Claims

Patentansprflche

1. Compounds of formula (I)

in which

X represents hydrogen, halogen or alkyl,

m represents integers from 2 to 10,

n represents 0, 1 or 2,

Y represents optionally substituted methylene and

p represents 1, 2 or 3.

2. A method for producing connections according to claim 1, characterized in that

a) Mercapto derivatives of the formula (II)

in which

Y and p have the meaning given in Claim 1, with fluoroalkenyl halides of the formula (III)

in which

X and m have the meaning given in spoke 1 and

Shark represents halogen,

in the presence of a diluent and, if appropriate, in the presence of a basic reaction auxiliary, the compounds of the formula (II) also being able to be used in the form of their salts, preferably the alkali metal salts, in particular the sodium or potassium salts; and if necessary

the heterocyclic according to the invention thus obtained

Fluoroalkenyl thioethers of the formula (Ia)

in which

X, Y, m and p have the meaning given in claim 1,

oxidized with an oxidizing agent, optionally in the presence of a diluent and optionally in the presence of a catalyst.

3. Compounds according to claim 1, characterized in that

X represents hydrogen, fluorine, chlorine or bromine,

m represents integers from 2 to 8,

n represents 0 or 2,

Y for optionally single or double, identical or different by in each case optionally by halogen, -C ₄ - alkoxy, C ₁ -C ₄ -

Alkylthio, C] -C ₄ - haloalkoxy or C ₁ -C ₄ haloalkylthio substituted CrC - alkyl, C ₂ -C ₄ alkenyl or C ₂ -C ₄ alkynyl substituted methylene, or trisubstituted optionally monosubstituted to the same or different from halogen, cyano, nitro, Cj-C ₄ -alkyl, CC ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkyl, -C ₄ -

Halogenalkoxy or C ₁ -C ₄ haloalkylthio substituted phenyl substituted methylene, and

p represents 1 or 2.

4. Connections according spoke 1 or 3, characterized in that

X represents hydrogen or fluorine,

m represents integers from 2 to 6,

n stands for 0,

Y represents methylene optionally substituted once or twice, identically or differently by - - alkyl, or represents methylene optionally substituted once or twice, identically or differently by halogen, Cyano, nitro, C ₁ -C ₂ alkyl, Ci-C ₂ alkoxy, dC ^ alkylthio, CrC ₂ - haloalkyl, C ₁ -C ₂ haloalkoxy or C ₁ -C ₂ haloalkylthio substituted phenyl substituted methylene, and

p stands for 1.

5. Compounds according to any one of claims 1, 3 or 4, characterized in that

X represents fluorine,

m represents 2 or 4, and

Y represents methylene optionally substituted once or twice, identically or differently by methyl or ethyl, or represents methylene substituted optionally substituted once or twice, identically or differently by fluorine, chlorine, methyl, methoxy, trifluoromethyl, cyano or nitro.

6. Compounds of the formula (Ila)

in which

Y has the meaning given in spoke 1.

7. Compounds of formula (V)

in which

R represents - - alkyl, preferably methyl and

Y has the meaning given in claim 1.

8. Compounds of the formula (VI)

in which

Y has the meaning given in spoke 1.

9. Compounds of formula (I)

in which

Y, p, n, m and X have the meanings given in the table below for the individual compounds. Connection -00p - nm X

No.

1 -CH ₂ - 0 2 F

2 -CH ₂ - 0 2 H

3 -CH ₂ - 0 4 F

4 -CH ₂ - 0 4 H

5 ~ (CH ₂ ) ₂ - 0 2 F

6 - (CH ₂ ) ₂ - 0 4 H

7 -CH (CH ₃ ) - 0 2 F

8 -CH (CH ₃ > 0 2 H

9 -CH (CH ₃ 0 4 F

10 -CH (CH ₃ ) - 0 4 H

11 - (CH ₂ ) ₂ - 0 2 H

12 - (CH ₂ ) ₂ - 0 4 F

13 - (CH ₂ ) ₃ - 0 2 F

14 - (CH _{2) 3} - H 0 2

15 - (CH ₂ ) ₃ - 0 4 F

16 - (CH _{2) 3} - H 0 4

10. pesticide, characterized by a content of at least one compound of the formula (I) according to spoke 1 and conventional extenders.

11. Use of compounds of formula (I) according to spoke 1 for controlling pests.

12. A method for controlling pests, characterized in that compounds of the formula (I) according to Claim 1 or a pesticide according to Claim 10 are allowed to act on pests and / or their habitat.

13. A process for the preparation of pesticides, characterized in that compounds of the formula I according to spoke 1 are mixed with extenders and / or surface-active agents.

14. Use of compounds of formula (I) according to claim 1 for the preparation of pesticides.