EP1414815A1

EP1414815A1 - Tetrahydropyridazine derivatives and their use as pesticides

Info

Publication number: EP1414815A1
Application number: EP02748854A
Authority: EP
Inventors: Fritz Maurer; Christoph Erdelen; Udo Reckmann; Andreas Turberg; Angelika Lubos-Erdelen
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2001-07-25
Filing date: 2002-07-12
Publication date: 2004-05-06
Also published as: MXPA04000623A; BR0211480A; JP2005501045A; US20050150764A1; KR20040016989A; CN1535270A; WO2003010162A1; DE10136066A1

Abstract

The invention relates to novel tetrahydropyridazine derivatives of formula (I), in which R, X and Y have the meanings as cited in the description, to a method for the production thereof, and to their use as pesticides.

Description

TETRAHYDROPYRIDAZINE DERIVATIVES AND THEIR USE AS PESTICIDES

The present invention relates to new tetrahydropyridazine derivatives, a process for their preparation and their use as pesticides.

It is known that certain tetrahydropyridazine carboxamides show good activity against animal pests (cf. e.g. DE-A 43 03 658 or WO 91 / 17-983).

However, the level of action or duration of action of these previously known compounds is not entirely satisfactory in all areas of application, in particular in the case of certain organisms or at low application concentrations.

New tetrahydropyridazine derivatives of the formula (I) have been found

R represents hydrogen, halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, hydroxy, nitro, cyano, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl,

X represents halogen, haloalkyl, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl or cyano and Y represents halogen, haloalkyl, haloalkoxy, haloalkylthio, halosulfonyl, haloalkylsulfonyl or cyano.

It was also found that the tetrahydropyridazine derivatives of the formula

(I) is obtained if tetrahydropyridazme of the formula (II)

in which

R and X have the meaning given above,

with isocyanates of the formula (III)

in which

Y has the meaning given above,

if appropriate in the presence of a diluent.

Finally, it was found that the new tetrahydropyridazine derivatives of the formula (I) have highly pronounced biological properties, and especially for

Control of animal pests, in particular insects, arachnids and nematodes, which are found in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. Formula (I) provides a general definition of the tetrahydropyridazine derivatives according to the invention.

Preferred substituents or ranges of those mentioned in the above and below

The radicals listed in formulas are explained below:

R preferably represents hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alko y, C 1 -C 4 -alkylthio; for Cj- ^ haloalkyl, Cj-C4-haloalkoxy and C1-C4-haloalkylthio, each with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; for hydroxy, nitro, cyano; for C 1 -C 4 alkoxy-carbonyl, aminocarbonyl, C 1 -C 4 -alkylanιino-carbonyl or di-C 1 -C 4 -alkylamino-carbonyl.

X preferably represents halogen, -CC-C4-alkylthio, C] ^ C4-alkylsulfinyl, C1-C4-

alkylsulfonyl; for -C-C4-haloalkyl, Cι-C4-haloalkoxy, C \ -C ^ - haloalkylthio, Cι-C4-haloalkylsulfinyl and Cι-C4-haloalkylsulfonyl, each with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and Bromine; or for cyano.

preferably represents halogen; for Cj-C4-haloalkyl, Cι-C4-haloalkoxy, C] ^ C4-haloalkylthio, Cι-C4-haloalkylsulfinyl and C1-C4-haloalkylsulfonyl, each with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine ; or for cyano.

R particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl,

Methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,

Cyano, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl or methyl ethyl aminocarbonyl. X particularly preferably represents fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfonyl, trifluoromethylthio, trifluoromethylsulfonyl or cyano.

Y particularly preferably represents fluorine; Chlorine, bromine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl, difluoromethyl, difluoromethoxy or cyano.

The radical definitions or explanations listed above or listed 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 meanings listed above as preferred (preferred)

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

In the radical definitions listed above and below, hydrocarbon radicals, such as alkyl - in each case straight-chain or branched - as far as possible - also in connection with heteroatoms such as alkoxy.

If, for example, 4- (4-chloropyrazol-l-yl) -3- (3-fluorophenyl) -1, 4,5,6-tetrahydropyridazine and 4-trifluoromethylphenyl isocyanate are used as starting materials, the reaction sequence of the process according to the invention can be determined using the following formula are reproduced:

Formula (II) provides a general definition of the tetrahydropyridazines to be used as starting materials in the process according to the invention. The tetrahydropyridazines of the formula (II) are not yet known and are also the subject of this application. They can be obtained in a generally known manner by using ω-chloro ketones of the formula (IV)

in which

R and X have the meanings given above, with hydrazine hydrate (NH2-H2 H2O), optionally in the presence of a diluent, such as ethanol, at temperatures between 0 ° C and 50 ° C (see also the preparation examples).

The ω-chloro ketones of formula (IV) are also new and the subject of this application. They can be obtained in a generally known manner by using dihalogen ketones of the formula (V)

in which

X has the meaning given above,

with known pyrazoles of the formula (VI)

in which

R has the meaning given above;

preferably in the form of the hydrohalides, such as hydrochlorides, optionally in the presence of an inert diluent, preferably nitriles, such as acetonitrile; Ketones, such as acetone or amides, such as dimethylformamide and optionally in the presence of bases, such as, for example, alkaline earth metal carbonates _. converts tertiary alcoholates, alkali metal hydrides or tertiary amines at temperatures from -20 ° C to 40 ° C (see also the preparation examples). The dihaloketones of the formula (V) are known (cf., for example, EP-A 657 421) or can be obtained by known processes by, for example, the corresponding monohalogen ketones of the formula (VI)

in which

X has the meaning given above,

Brominated in the usual way (see also the manufacturing examples).

The monohalogen ketones of the formula (VI) are known (cf. e.g. EP-A 657 421 or US 3 859290) or can be obtained by known processes by using furanone derivatives of the formula (VII)

X has the meaning given above,

in a known manner with concentrated hydrochloric acid at temperatures between

30 ° C and 60 ° C (see also the manufacturing examples).

Some of the furanone derivatives of the formula (VII) are known (cf., for example, JP-A 55127382 [CA 94, 174852]). Not yet known and also the subject of this application are furanone derivatives of the formula (VIIa) in which

X ¹ for fluorine, bromine; C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 acylsulfonyl; for -C -C4-haloalkyl, Cι-C4-haloalkoxy, C ^ -C4-haloalkylthio, Cι-C4-haloalkylsulfinyl and Cι -C4-haloalkylsulfonyl each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine , or stands for cyano.

The new furanone derivatives of the formula (VIIIa) can be obtained in a generally known manner by known methyl benzoates of the formula (VIII)

in which

X ^{1 has} the meaning given above,

with γ-butyrolactone of the formula (IX)

in a generally known manner in the presence of a diluent, such as, for example, tetrahydrofuran and in the presence of alcoholates, such as, for example, potassium tert-butoxide, at temperatures between 0 ° C. and 80 ° C. (cf. also the preparation examples). The isocyanates of the formula (III) which are also to be used as starting materials for carrying out the process according to the invention are generally known compounds of organic chemistry.

The process according to the invention is preferably carried out using diluents. Practically all inert organic solvents can be used as diluents. These preferably include ahphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ether such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl or methyl isobutyl ketone, esters such as methyl acetate or ethyl acetate, nitriles such as, for example Acetonitrile or propionitrile, amides such as e.g.

Dimefhylformamide, dimethylacetamide and N-methylpyrrolidone as well as dimethyl sulfoxide, tetramethylene sulfone or hexamethylene phosphoric acid triamide.

The reaction temperatures can be varied within a wide range in the process according to the invention. In general, temperatures between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 80 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.

To carry out the process according to the invention, the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess. Working up is carried out in the methods according to the invention in each case by customary methods (cf. the preparation examples). 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. 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 e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda e.g. Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus _. Scutigera spp ..

From the order of the Symphylaz.B. 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, for example 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, for example Reticulitermes spp .. From the order of the Phthiraptera, for example 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 accidentalis.

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 e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigemm, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphorumumon., Macrosiphodumon. Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppppi, Fitrella, Phyllocnist spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionellaanaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaella pellaella , Choristoneura fumiferana, Clysia ambiguella, 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 chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulususoderhimpphppm, spp. , Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimalltrastitium Lissorhoptrus oryzophilus.

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

Monomorium pharaonis, Vespa spp.

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

Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomy

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., Hyalommodes spp., Ix. Chorioptes spp., Sarcoptes spp.,

Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp ..

Plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp ..

The substances according to the invention can be used with particularly good success for controlling plant-damaging insects, such as against caterpillars of the cotton capsule worm (Heliothis virescens), the larvae of the horseradish beetle (Phaedon cochleariae), the caterpillars of the cockroach (Plutella xylostella) and caterpillars of the army worm (Spodoptera exigua and Spodoptera frugioerda).

The substances according to the invention also show resistance-inducing

Effect, especially against Erysiphe graminis.

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 unwanted 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 those by

Plant variety rights of protectable or non-protectable plant varieties. 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. One of the plant parts also crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and plant parts according to the invention with the active substances takes place directly or by acting on their environment, habitat or

Storage room according to the usual 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 compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, 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 and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers: e.g. ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, MontmoriUonit or diatomaceous earth and synthetic rock powders such as highly disperse silicic acid, aluminum oxide and silicates, as solid carriers for granulates are possible: e.g. broken and fractionated natural rocks such as Calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters,

Polyoxyethylene fatty alcohol ethers, 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 powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc 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 compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order to thus, for example, improve the spectrum of action. broaden or prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:

fungicides:

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

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

Calciumpolysulfϊd, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon,

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

Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran,

Diethofencarb, Difenoconazol, Dimethirimol, Dimethomorph, Diniconazol, Diniconazol-M, Dinocap, Diphenylamin, 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, Fluquinconazol, Flu rimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-Alminium, Fosetyl- Sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,

guazatine,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, 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, Paclobutrazol, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Picoxystrobin, Pimaricin, Piperalin, Polyoxin, Polyoxorim, probenazol, Prochloronine, Propazazoline, Prochlorazinol

Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Pyroxyfur,

Quinconazole, quintozen (PCNB),

Sulfur and sulfur preparations, Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tri- cyclazol, tridemorph, trifloxystrobin, triflumizole, Triforin, triticonazole,

uniconazole

Validamycin A, vinclozolin, viniconazole,

Zarilamid, Zineb, Ziram as well

Dagger G,

OK 8705,

OK-8801, α- (l, l-dimethylethyl) -ß- (2-phenoxyethyl) -lH-l, 2,4-triazole-l-ethanol, - (2,4-dichlorophenyl) -ß-fluoro-b -propyl-lH-l, 2,4-triazole-l-ethanol, - (2,4-dichlorophenyl) -ß-methoxy-a-methyl-1 H-1, 2,4-triazole-1-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 ₅ 7,7-tetramethyl-5- (lH-l, 2,4-triazol-l-yl) -3-octanone,

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

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

1-isopropyl ester l- (2,4-dichlorophenyl) -2- (lH-l, 2,4-triazol-l-yl) -ethanone-0- (phenylmethyl) -oxime, l- (2-methyl-l- naphthalenyl) -IH-pyrrole-2,5-dione, l- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, l - [(diiodomethyl) sulfonyl] -4-methyl -benzene, l - [[2- (2,4-dichlorophenyl) -l _s 3-dioxolan-2-yl] methyl] -IH-imidazole, l - [[2- (4-CMoιhenyl) -3- phenyloxiranyl] -methyl] -lH-l, 2,4-triazole, l- [l- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] -ethenyl] -lH-imidazole, 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

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

2,2-dichloro-N- [1 - (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide, 2,6-dichloro-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-4-0- (4-0-methyl-β-D-glycopyranosyl ) -aD-glucopyranosyl] -amino] -4- memoxy-lH-pyιolo [2,3-d] pyrimidine-5-carbonitrile,

2-aminobutane,

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

2-chloro-N- (2,3-dihydro-1, 1, 3 -trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N - (isothiocyanatomethyl) acetamide,

2-phenylphenol (OPP),

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

3,5-dichloro-N- [cyano [(l-methyl-2-propynyl) -oxy] -methyl] -benzamide,

3 - (1,1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile, 3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,

4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -1 H-imidazole-1-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- [(phenylamino) carbonyl] hydrazide, bis- (1-methylethyl) -3-methyl-4- [(3-methylbenzoyl) -oxy] -2, 5-thiophene dicarboxylate, ice-1 - (4-chlorophenyl) -2- (1 H- 1, 2,4-triazol-1-yl) -cycloheptanol, cis-4- [3- [4- (l, l- Dime ylρropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride, ethyl - [(4-chlorophenyl) azo] cyanoacetate,

potassium bicarbonate, Methantetrathiol sodium salt,

Methyl-l- (2,3-dihydro-2,2-dimethyl-lH-inden-l-yl) -lH-imidazol-5-carboxylate,

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

Methyl-N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide.

N- (2,6-Dimemylphenyl) -2-methoxy-N- (tettahydro-2-oxo-3-furanyl) acetamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,

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

N- (4-cyclohexylphenyl) -l, 4,5,6-tetrahydro-2-pyrimidinamine, N- (4-hexylphenyl) -l, 4,5,6-tetrahydro-2-pyrimidinamine,

N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,

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

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

N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxymanimidamide, N-formyl-N-hydroxy-DL-alanine sodium salt,

0,0-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat,

0-methyl-S-phenyl-phenylpropylphosphoramidothioat,

S-methyl-l, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] -l-benzopyran-2, r (3Η) -isobenzofuran] -3'-one, 4- [3,4-dimethoxyphenyl) - 3- (4-fluorophenyl) acryloyl] morpholine

bactericides:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, 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 Üruringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Berrfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomifinin, Bifinhromifrin, Bifurin Bifurin, Bethiromifinin , Butocarboxime, butylpyridaben,

Cadusafos, carbaryl, carbofuran, Carbophenofhion, carbosulfan, cartap, Chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, Chlo yrifos M, Chlovaporthrin, chromafenozide, cis-resmethrin, Cispermethrin, Clocythrin, cloethocarb, clofentezine, Clothianidine, Cyanophos, Cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Dicofol, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,

Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,

Fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim,

Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazina, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucyfhrinate, Flufenoxuron, Flumethrin, Flutenzine, Fluvalinate, Fonophos, Fostiarbof, Fosarbiazil, Fosti Methfiazole

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

Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,

nucleopolyhedroviruses

Lambda cyhalothrin, lufenuron

Malathion, mecarbam, metaldehyde, methamidophos, metharhilic anisopliae,

Metharhilicium flavoviride, methidathione, methiocarb, methoprene, methomyl, 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, Propargite, Propoxur, Prothiofos, Prothoat, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxyfen,

quinalphos,

ribavirin

Salithion, Sebufos, Silafluofen, Spinosad, Spirodiclofen, Sulfotep, Sulprofos, Tau-fluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, tetradifon theta cypermethrin, thiacloprid thiocyclam hydrogen oxalate, thiamethoxam, Thiapronil, Thiatriphos, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene , 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-dimethylcyclopropane carboxylate

(3-phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropane decarboxylate l - [(2-chloro-5-toluene) methyl] tettahydro-3,5-dimethyl-N-nitro-l ₃ 3.5 -triazin-2 (lH) - imine

2- (2-Chloro-6-fluoφhenyl) -4- [4- (l, 1-dimethylethyl) phenyl] -4,5-dihydro-oxazole 2- (acetyloxy) -3 -dodecyl- 1, 4-naphthalenedione

2-chloro-N- [[[4- (1-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] -l-fluoro-2-phenoxy-benzene 4-Cωor-2- (l, l-dime le l) -5 - [[2- (2, 6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -

-pyridazinone 3 (2H)

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

4-CMor-5 - [(6-cmor-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -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-dichlorophenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4-yl ester

[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cy anamide

Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde ethyl- [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy ] ethyl] carbamate

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

N- (4-Chlθφhenyl) -3 - [4- (difluoromethoxy) phenyl] -4.5 -dihydro-4-phenyl- 1 H-pyrazole-

1-carboxamide

N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine N-methyl-N '- (1-methyl-2-propenyl) -l, 2-hydrazinedicarbothioamide

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

0,0-Diemyl- [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat

N-cyanomethyl-4-trifluoromethyl-nicotinamide

3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propoxyj-benzene

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 also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds 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 active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight. The application takes place in a customary manner adapted to the application forms

Wise.

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

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild or conventional organic breeding methods, such as crossbreeding or

Protoplast fusion obtained plant species and plant varieties and their parts treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated. The term "parts" or "parts of

Plants "or" parts of plants "was explained above.

According to the invention, plants of the plant cultivars which are in each case commercially available or in use are particularly preferably treated. Plant cultivars are understood to mean plants with new properties (“traits”) which have been bred 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 widening of the spectrum of action 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, Accelerated 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 possible, which go beyond the effects that are actually to be expected.

The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, have received genetic material 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 drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, 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 insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants include 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 , Cotton and rapeseed are highlighted. The traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CryΙA (b), CryΙA (c), CryllA, CryfflA, CryIIIB2, Cry9c Cry2Ab,

Cry3Bb and CrylF and their combinations) are generated in the plants (hereinafter "Bt plants"). The properties ("traits") also particularly emphasize 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 increased tolerance is further emphasized as properties ("traits") the plants against certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene). The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize, cotton, soybean and

Potato varieties named under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato) to be expelled. Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties which are sold under the trade names 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® (e.g. 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 active compounds according to the invention act not only against pests from plants, hygiene and stored products, 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, for example 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 e.g. 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., Raillietia spp.,

Pneumonyssus spp., Sternostoma spp., Varroa spp .. From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., 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 Infest hamsters, guinea pigs, rats and mice. By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets,

Capsules, 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 aid of shaped articles 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

Formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active substances in an amount of 1 to 80% by weight, directly or after 100 to 10,000-fold dilution or use them as a chemical bath.

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 pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis,

Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.

Skin wings like

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

Termites 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 ingredient 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, turpentine oil 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 lock oil and / or monochloronaphthalene, preferably α-monochloronaphthalene, are used. The organic non-volatile 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 or an aliphatic polar organic chemical solvent or solvent mixture is replaced. Aliphatic organochemical 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 indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin used.

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

According to the invention, preference is given to at least one alkyd resin or modified alkyd resin and / or a drying plant-based organic-chemical binder

Contain oil in the medium or in the concentrate. Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.

The binder mentioned can be wholly or partly by a fixing agent.

(mixture) or a plasticizer (mixture) can be replaced. 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 alcohols such as 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 by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes. The ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.

The insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional mixing partners. The ones mentioned in this document

Connections are an integral part of this application.

Insecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, methoxyphenuriflifon, trifluoropurine,

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 -octyl-isothiazolin-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 Scalpellum, or by species from the group Balanomoφha (barnacles), such as

Baianus or pollicipes species, increases the frictional resistance of ships and, as a result, 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., the vegetation comes in particular through sessile Entomostraken groups, which are summarized under the name Cirripedia (barnacles).

It has now surprisingly been found that the compounds according to the invention, alone or in combination with other active ingredients, are excellent

Have 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-K-butyltin laurate, tri-butyltin chloride, copper (I) oxide,

Triethyltin chloride, tri - «- butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-M-butyltin fluoride, manganese ethylene thiothiocarbamate, Zinc ethylene bishiocarbamate, zinc and copper salts of 2-pyridine-thiol-1-oxide, bisdimethyldithiocarbamoyl zinc ethylene bisthiocarbamate, zinc oxide,

Copper (I) ethylene bisdithiocarbamate, copper thiocyanate, copper phthalate and tributyltin halides can be dispensed with or the concentration of these compounds can be significantly reduced.

The ready-to-use antifouling paints can also be used if necessary

Contain 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-butylamino-4-cyclopropylamino-6-methylthio-1, 3,5-triazine, dichlorophen, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen,

Quinoclamine and Terbutryn; Fungicides like

Benzo [ό] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorofolpet, 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, diiodomethyl paratryl sulfone, 2- (N, N-dimethyl ylthiocarbamoylthio) -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 inventive insecticidal active substances, 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, in particular 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, drying

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 substances are also suitable for combating animal pests, in particular insects, arachnids and mites, which live in closed spaces such as, for example, apartments, factories, offices, vehicle cabins and the like. 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, for example 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 e.g. Aviculariidae, Araneidae.

From the order of the Opiüones e.g. 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 Psocoptera, for example Lepinatus spp., Liposcelis spp. From the order of the Coleptera, for example 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 e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Phrosophila spp., Fannia canicularis. Spp., Fannia canicularis 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, Xenops lla cheopis.

From the order of the Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius urnbratus, 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, unpressurized sprays, e.g. pump and atomizer sprays, automatic 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 papers and moth gels, as granules or dusts, in lures or bait stations.

Preparation Examples

example 1

To a solution of 1.27 g (4.4 mmol) of 3- (3-cyanophenyl) -4- (4-chloro-yrazol-l-yl) - 1,4,5,6-tetrahydropyridazine (Ex. II-1) In 30 ml of acetonitrile, a solution of 0.89 g (4.4 mmol) of 4-trifluoromethoxyphenyl isocyanate in 10 ml of acetonitrile is added dropwise at room temperature and the mixture is stirred for 6 hours at room temperature. Then the precipitated product is filtered off, the filtrate is evaporated in vacuo. The residue is triturated with ethanol, the product is filtered off after crystallization and washed with ethanol.

0.44 g (20% of theory) of 3- (3-cyanophenyl) -4- (4-chloro-yrazol-l-yl) -l- (4-trifluoromethoxyphenylamino) -carbonyl-l, 4.5 are thus obtained , 6-tetrahydropyridazine in the form of colorless

Crystals with logP (pH2) = 4.08 and melting point 216 ° C.

Manufacture of raw materials

1 is added to a solution of 5.3 g (17.2 mmol) of 3'-cyano-2- (4-chloro-yrazol-l-yl) -4-chlorobutyrophenone (Example IV-1) in 50 ml of ethanol , 7 g (35 mmol) hydrazine hydrate and stir the mixture overnight at room temperature. Then the solvent is distilled off in vacuo, the residue is mixed with water and extracted with ethyl acetate. The organic phase is separated off, dried over sodium sulfate and evaporated in vacuo.

This gives 3.8 g (78% of theory) of 3- (3-cyanophenyl) -4- (4-chloro-yrazol-l-yl) - 1,4,5,6-tetrahydropyridazine as a colorless powder with the logP ( pH2) = 2.29 and the melting point 171 ° C.

A solution of 14.3 g (0.05 mol) is added dropwise at -5.degree. C. to a mixture of 7 g (0.05 mol) 4-chloro-pyrazole hydrochloride, 13.8 g (0.1 mol) potassium carbonate and 60 ml acetonitrile. 05 mol) of 3'-cyano-2-bromo-4-chloro-butyrophenone (Example VI) in 20 ml of acetonitrile and the mixture is then stirred for 18 hours at room temperature. Then the reaction mixture is mixed with water and extracted with vinegar acid ethyl ester. The organic phase is separated off, dried over sodium sulfate and evaporated in vacuo. The residue is triturated with isopropanol, left to stand at room temperature overnight and then the precipitated product is filtered off with suction.

This gives 3.8 g (25% of theory) of 3'-cyano-2- (4-chlθφyrazol-l-yl) -4-chlorobutyrophenone as a beige powder with the logP (pH2) = 2, 95th

0.1 g of aluminum chloride is added to a solution of 32.7 g (0.15 mol) of 3'-cyano-4-chloro-butyrolphenone (Ex. VI-1) in 150 ml of methylene chloride, and 25.6 g are then added dropwise

(0.16 mol) of bromine. The mixture is stirred overnight at room temperature and then nitrogen is passed through the reaction mixture to remove the hydrogen bromide. Then, with stirring, water and then saturated sodium bicarbonate solution are added until the aqueous phase is neutral. Now the organic phase is separated off, dried over sodium sulfate, filtered and evaporated in vacuo. The residue is triturated with petroleum ether and the product is filtered off after crystallization.

This gives 40.8 g (95% of theory) of 3'-cyano-2-bromo-4-chloro-butyrophenone as a beige powder with the logP (pH2) = 3.09.

A mixture of 48 g (0.22 mol) of 3- (3-cyanobenzoyl) -γ-butyrolactone (Ex. VIIa-1) and 200 ml of concentrated hydrochloric acid is stirred for 2 hours at 35 to Heated 40 ° C, then the temperature is increased to 50 ° C for 30 minutes. The reaction mixture is cooled in an ice bath and then the precipitated product is filtered off with suction, washed with water and air-dried

This gives 32.9 g (71% of theory) of 3'-cyano-4-chloro-butyrophenone in the form of a beige powder with the logP (pH2) = 2.49.

A solution of 40.3 g (0.25 mol) of 3-cyanobenzoe is added dropwise to a solution of 30.2 g (0.27 mol) of potassium tert-butoxide in 300 ml of tetrahydrofuran - Acid methyl ester and 21.8 g (0.25 mol) of γ-butyrolactone in 50 ml of tetrahydrofuran and the mixture is stirred for 18 hours at room temperature. Then the solvent is distilled off in vacuo, the residue is dissolved in water and extracted with diethyl ether. The aqueous phase is separated off and adjusted to about pH 1-2 with ice-cooling using dilute hydrochloric acid. The mixture is extracted twice with methylene chloride, the organic phases are dried over sodium sulfate and the solvent is then evaporated off in vacuo.

46.1 g (86% of theory) of 3- (3-cyanobenzoyl) -γ-butyrolactone are thus obtained in the form of a partially crystalline oil with the logP (pH2) = 1.48.

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

Analogously to Example 1, the new starting products of the formula (II) given in Table 2 below can be obtained:

Table 2:

The new intermediates of the formula (IV) given in Table 3 below can be obtained analogously to Example 1:

Table 3:

The intermediates of the formula (V) given in Table 4 below can be obtained analogously to Example 1: Table 4:

The intermediates of the formula (VI) given in Table 5 below can be obtained analogously to Example 1:

Table 5:

Analogously to Example 1, the new intermediates of the formula (VIIa) given in Table 6 below can be obtained:

Table 6:

Application examples:

Example A

Heliothis virescens 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.

Soybean shoots (Glycine max) are treated by dipping into the active ingredient preparation of the desired concentration and populated with Heliothis virescens caterpillars 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 500 ppm, for example the compounds of Preparation Examples 1, 13, 14, 15 and 17 show 100% killing after 6 days.

Example B

Phaedon pine 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 leaf 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 1000 ppm, the compounds of preparation examples 2,3,4,5,6,7,8,9,10,11,12 and 16, for example, show 100% killing after 7 days.

Example C

Plutella Test

Solvent: 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

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 cockroach (Plutella xylostella) while the leaves are still moist.

Example D

Spodoptera exigua test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Concentration.

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

Example E

Spodoptera frugiperda test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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.

In this test, at an exemplary active ingredient concentration of 1000 ppm, the compounds of Preparation Examples 2,3,4,5,6,7,8,9,10,11,12 and 16, for example, show 100% kill after 7 days.

Example F

Effectiveness test: Heliothis virescens

Solvent: 9 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Concentration.

Cotton plants (Gossypium hirsutum) are sprayed with an active ingredient preparation of the desired concentration. After the specified days, Heliothis virescens caterpillars are placed on the treated leaves in infection chambers.

In this test, at an exemplary active ingredient concentration of 20 ppm, the compound according to preparation example 14, for example, shows an infection of 100% after 5, 12, 19 and 26 days.

Example G

Effectiveness test: Spodoptera frugiperda

Solvent: 9 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

Cotton plants (Gossypium hirsutum) are sprayed with an active ingredient preparation of the desired concentration. After the specified days, caterpillars of the army worm (Spodoptera frugiperda) are placed on the treated leaves in infection chambers.

This test shows a good effect with an exemplary active ingredient concentration of 20 ppm:

Example H

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 discs 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, e.g. the following compounds of the preparation examples have a good effect

Example I

BIowfly larva test / development-inhibiting effect

Test animals: Lucilia cuprina larvae

Solvent: dimethyl sulfoxide

About 20 Lucilia cuprina larvae are placed in a test tube, which contains approx.

Contains 1 cm ³ horse meat and 0.5 ml of the drug 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 another

The test tubes are removed for 2 days 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.

Claims

Patentanspräche

1. Compounds of formula (I)

in which

X represents halogen, haloalkyl, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfmyl, haloalkylsulfonyl or cyano and

Y represents halogen, haloalkyl, haloalkoxy, haloalkylthio, halosulfinyl, haloalkylsulfonyl or cyano.

2. Compounds of formula (I) according to spoke 1, in which

R is hydrogen, halogen, Cι-C4-alkyl, _Cι-C4 alkoxy, C1-C4 alkylthio; for C1-C4_.Halogena.kyl, Cι-C4-haloalkoxy and C \ - C4-haloalkylthio, each with 1 to 5 identical or different Halogen atoms from the series fluorine, chlorine and bromine; for hydroxy, nitro, cyano; stands for Ci-Gj-alkoxy-carbonyl, aminocarbonyl, C1-C4-alkylamino-carbonyl or di-Cι-C4-alkylamino-carbonyl.

X for halogen, -CC4-alkylthio, -C-C4-alkylsulfinyl, -C-C4-alkylsulfonyl; for -C -C-haloalkyl, Cι-C4-haloalkoxy, C1-C4-haloalkylthio, C] -C4-haloalkylsulfinyl and Cι-C4-haloalkylsulfonyl, each with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine ; or stands for cyano.

Y for halogen; for -C-C4-haloalkyl, Cι-C4-haloalkoxy, Ci

C4-haloalkylthio, Cι-C4-haloalkylsulfonyl and Cι- 4-haloalkylsulfonyl each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; or stands for cyano.

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

R for hydrogen, fluorine, chlorine, bromine, methyl, methoxy, methylthio,

Trifluoromethyl, trifluoromethoxy, trifluoromethylthio, cyano, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl or methylethylamino carbonyl.

X represents fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy, methylthio, methylsulfonyl, trifluoromethylthio, trifluoromethylsulfonyl or cyano. Y for fluorine; Chlorine, bromine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl, difluoromethyl, difluoromethoxy or cyano.

Process for the preparation of compounds of formula (I), characterized in that compounds of formula (II)

in which

R and X have the meaning given above,

with compounds of the formula (III)

in which

has the meaning given above,

if appropriate in the presence of a diluent.

5. Compounds of formula (II)

in which

R and X have the meaning given above.

6. Compounds of the formula (IV)

in which

R and X have the meaning given above.

7. Compounds of the formula (VII a)

in which

X ¹ for fluorine, bromine; C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl; for C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 4 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfmyl and C 1 -C 4 haloalkylsulfonyl, each with 1 to 5 identical or different

Halogen atoms from the series fluorine, chlorine and bromine, or cyano.

8. pesticides, characterized by a content of at least one compound of the formula (I) according to claim 1.

9. A method for controlling animal pests, characterized in that compounds of the formula (T) according to claim 1 are allowed to act on pests and / or their habitat.

10. Use of compounds of formula (I) according to claim 1 for combating animal pests.

11. A process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claim 1 with

Extenders and / or surfactants mixed.

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