EP1506164A1

EP1506164A1 - N -cyano-n-methyl-imidamide derivatives

Info

Publication number: EP1506164A1
Application number: EP03720556A
Authority: EP
Inventors: Achim Hense; Rüdiger Fischer; Ernst R. F. Gesing; Stefan Herrmann; Kristian Kather; Christoph Erdelen; Jörg KONZE; Peter Lösel
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2002-05-13
Filing date: 2003-05-08
Publication date: 2005-02-16
Also published as: US7365098B2; WO2003095418A1; JP2006507222A; DE10221121A1; AU2003224149A1; US20060035978A1

Abstract

The invention relates to novel N'-cyano-N-methyl-imidamide derivatives of general formula (I) wherein n represents 2, 3, 4 or 5, R represents optionally halogen-substituted C1-C4-alkyl, and X represents Halogen, wherein the substituents X can be respectively the same or different. The invention also relates to a method for the production thereof and the use thereof as pesticides.

Description

N-cyano-N-methyl-imidamide derivatives

The present application relates to new N'-cyano-N-methyl-imidamide derivatives, a process for their production and their use for controlling animal pests.

Certain Ν'-cyano-Ν-methyl-imidamide derivatives are already known (cf. WO 91/04 965, WO 93/04032, EP 0 403 159 A2; DE 195 48 783 AI, J Organomet. Chem. (1975) , 97 (1), pp. 39-44; Bull. Soc. Chim. Belg. (1981), 90 (1), pp. 89-98 and in particular WO 00/03976). Insecticidal properties of some of these compounds were also known (cf. EP 0 314 852 AI).

However, the action of these compounds is not entirely satisfactory in every respect. The object of the present invention was therefore to provide further compounds which have a convincing action against pests.

New imidamide derivatives of the general formula (I) have now been found

in which

n represents 2, 3, 4 or 5,

represents optionally substituted by halogen -CC ₄ alkyl, and X represents halogen, where the different substituents X can each be the same or different.

The N'-cyano-N-methylimidamide derivatives of the formula (I) can exist as optical and / or geometric isomers. The present invention relates both to the various isomer mixtures and in particular to the pure isomers of the compounds according to the invention.

The new N'-cyano-N-methylimidamide derivatives of the general formula (I) are obtained if amines of the formula (II)

in which

X and n have the meanings given above,

(a) with N-cyano-alkylimidic acid esters of the formula (III)

Y— Q,

^N x (TU)

CN in which

R has the meaning given above,

Q stands for oxygen or sulfur and

Y represents alkyl, in the presence of a diluent, or

(a ') with orthoesters of the formula (IV)

in which

R has the meaning given above, and

Y represents alkyl,

and optionally reacting cyanamide in the presence of a diluent, and

(b) then alkylated by the compounds of the formula (V) formed according to process (a) or (&)

in which

R, X and n have the meanings given above,

with compounds of the formula (VI)

CH ₃ -Z (VI) in which

for a leaving group, e.g. Halogen (e.g. chlorine, bromine or iodine), mesylate or tosylate,

implements.

However, it is also possible to obtain the compounds of the formula (I) by using N-methylated amines of the formula (VII)

in which

X and n have the meanings given above,

with N-cyano-alkylimidic acid esters of the formula (III) according to process (a) or with orthoesters of the formula (IV) and cyanamide according to process (a '), the subsequent alkylation not being necessary.

The new N'-cyano-N-methyl-imidamide derivatives of the general formula (I) have very pronounced biological properties and are particularly suitable for controlling animal pests, such as insects, arachnids and in particular nematodes, which are used in agriculture, in the Forests, in stock and material protection as well as in the hygiene sector, are suitable.

The compounds according to the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below. n is preferably 2, 3 or 4.

R preferably represents methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine or bromine.

X preferably represents fluorine, chlorine or bromine.

If n is 2, a first substituent X is preferably in the σrtbo position (2) and a second substituent X is preferably in the rα position (4), or a first one

Substituent X is preferably in the metα position (3) and a second substituent X is preferably in the rα position (4).

If n is 3, a first substituent X is preferably in the ortbo position (2), a second substituent X in the αrα position (4), and a third substituent X in the metα position (5) a phenyl ring.

n particularly preferably represents 2 or 3.

R particularly preferably represents methyl, ethyl or n- or i-propyl optionally substituted by fluorine or chlorine.

X particularly preferably represents fluorine or chlorine.

If n is 2, a first substituent X is particularly preferably in the orbbo position (2) and a second substituent X is particularly preferably in the para position (4).

R very particularly preferably represents methyl or ethyl. Particularly preferred compounds in the context of the above substituent definitions are compounds of the formulas (IA) to (IE):

Very particularly preferred compounds in the context of the above substituent definitions are compounds of the following formulas (IA) to (IE):

The general or preferred radical definitions or explanations listed above apply to the end products and to the starting and intermediate products accordingly. 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.

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, as far as possible, straight-chain or branched.

The amines of the general formulas (II) and (VII) to be used as starting materials in the process according to the invention are generally known compounds of organic chemistry or are obtainable in a generally known manner, e.g. according to Houben-Weyl, Methods of Organic Chemistry, Volume XI, 1; Chantrapromma et al., J. Chem. Soc. Perkin Trans. (1983) 1049-1062; Salerno et al., J Org. Chem.

65: 3971-3981 (2000); Atkinson et al., 1983, J Med. Chem. 26: 1353-1360; Kosugi et al., Bull. Chem. Soc. Jpn., 60 (1987), 767-68.

Formula (III) provides a general formula for the N-cyano-alkylimidic acid esters which are also required as starting materials for carrying out process (a) according to the invention Are defined. In this formula, Y is preferably especially for methyl or ethyl.

The N-cyano-alkylimidic acid esters are largely known (see, for example, US 5,304,566 or J Org. Chem. 28, 1963, 1816-1821) and / or can be obtained by customary processes.

Formula (IV) provides a general definition of the orthoesters also required as starting materials for carrying out process (a ') according to the invention. In this formula, Y is preferably especially for methyl or

Ethyl.

The compounds of the formula (IV) are compounds known to the person skilled in the art (cf. also Schäfer and Gewald, J Prakt. Chem. 318, 1976, 347-349).

The compounds of the formula (VI) used for the alkylation (methylation) of compounds of the formula (V) are likewise known compounds.

Process (a ') according to the invention can e.g. analogous to Schäfer and Gewald, J Prakt. Chem. 318, 1976, 347-349, wherein the synthesis of

Arylaminoethylene cyanamides is described.

The processes (a) and (a ') according to the invention can, as described above, also be carried out starting from N-methylated amines of the formula (VII) (see, for example, Edenhofer, Heb. Chim. Acta 58, 1975, 2192-2209), in which case the subsequent methylation is eliminated.

The processes according to the invention are preferably carried out in the presence of a diluent, although this is not absolutely necessary in the case of process (a '). Alcohols such as methanol and ethanol; Nitriles such as acetonitrile or esters such as ethyl acetate. It is also possible to work in water or organic-aqueous mixtures if necessary.

When carrying out the process according to the invention, it is preferred to work in equimolar amounts; but it is also possible to use one or the other starting product in excess.

The reaction temperatures can in performing ^"the method of this invention in a wider range can be varied. In general, one operates at temperatures between 0 ° C and 180 ° C, preferably between 20 ° C and 150 ° C, more preferably between 20 ° C and 80 ° C.

The end products are worked up and isolated in a manner known to us.

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 e.g. Geophilus carpophagus, Scutigera spp ..

From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example 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. Reticύlitermes 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 pal i, Frankliniella accidentalis.

From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Ci ex 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 po i, 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, Pseudococcuslapp. From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, LithocoUetis blancardella, Hyponomeuta padella, Plutella xylustella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Agristella spp ., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonellaellaellaellaellaellaellaella, Tineola tinmannella l , Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephuspp 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, A phimallon solstitialis, Costelytra zealandica.

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., Tabanus spp. Tannia spp., Bibio hortulanus, Oscinella ftit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp .. From the order of the Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp ..

From the class of the Arachnida e.g. Scorpio aurus, Latrodectus mactans.

From the order of the Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus 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., Bursa.

The compounds of the formula (I) according to the invention are notable in particular for good nematicidal activity. For example, they can be used with particularly good success to combat Meloidogyne incognita.

According to the invention, all plants and parts of plants can be treated. Under

Plants are understood 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 are produced by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations thereof

Methods can be obtained, including transgenic plants and including plant varieties that 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 are listed. To the Plant parts also include crops and vegetative and generative propagation material, such as 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 in the case of seeds, furthermore by coating in one or more layers.

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.

When used in the appropriate amounts, the compounds according to the invention show herbicidal effects in some cases.

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, organic solvents can, for example, 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, for example petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

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. 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 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 compound according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, 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 and others

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, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazol, Bupirimat, Buthiobat, Calciumpolysulfid, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Quinomethionate (Quinomethionat), Chlobenthiazon, Chlorfenazolonolon, Chlorfenazolonolon , Cuftaneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram, debacarb, dichlorophen, diclobutrazole,

Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethirimol, Dimethomorph, Diniconazol, Diniconazol-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxololid, Epipolazolox, Epipolazolox, Epipolazolox, Epipolazolox Fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,

Fentinhydroxyd, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-Alminium, fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr, Furcarbonil, furconazole, furconazole-cis, Furmecyclox, guazatin, hexachlorobenzene, hexaconazole, hymexazole, imazalil, imibenconazole, iminoctadine,

Iminoctadineal Besilat, Ltiiinoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, irumamycin, isoprothiolan, isovaledione, kasugamycin, kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, mancopper, mancozeb, maneb, meferim zone, mpranipilime, meponipilime, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram _^ Metomeclam, Metsulfovax, Mildiomycin,

Myclobutanil, Myclozolin, Nickel-dimethyldithiocarbamat, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin, Paclobutrazol, Pefurazoat, Penconazol, Polyciphenol, Proxinoxolin, Phonoxinol, Proxinoxolin, Phyconex, Proxinoxol Propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,

Pyroquilon, Pyroxyfur, Quinconazol, Quintozen (PCNB), Sulfur and Sulfur Preparations, Tebuconazole, Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazol, Thiabendazole, Thicyofen, Thifluzamide, Thiophanate-methyl, Toli, Cladlimolid, Tri, Tioxadlimid, Triadoflimid, Triadoflimid , Triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin, triticonazole, uniconazole,

Validamycin A, vinclozolin, viniconazole, zarilamide, zineb, ziram and Dagger G, OK-8705, OK-8801, - (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- 1H- 1, 2,4-triazole-1-ethanol, α- (5-methyl-1,3-dioxan-5-yl) -ß- [[4- (trifluoromethyl) phenyl] methylene] 1 H-1, 2,4-triazole-1-ethanol,

(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-l, 2,4-triazol-l-yl) -3-octanone, (E) -a- (methoxyimino ) -N-memyl-2-phenoxy-phenylacetamide, {2-methyl-l - [[[l- (4-memylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester, 1 - (2,4-Dicmorphenyl) -2- (lH-l, 2,4-triazol-l-yl) -emanone-O- (phenylmethyl) -oxime, l- (2-methyl-1-naphthalenyl) - 1 H -pyrrole-2,5-dione, 1 - (3,5-dichlorophenyl) -3 - (2-propenyl) -2, 5-pyrrolidinedione, l - [(diiodomethyl) sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1 H-imidazole, 1 - [[2- (4-chlorophenyl) -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 ', 6'-dibromo-2-methyl-4'-fluoromethoxy-4'-fluoro-memyl-l, 3-thiazole-5-carboxanilide, 2,2-dichloro- N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide, 2,6-dichloro-5- (MeÜιylthio) -4-pyrimidinyl-thiocyanate, 2,6-dichloro-N- (4-trifluoromethylbenzyl) - benzamide, 2,6-dicl-üor-N - [[4- (fluoromethyl) phenyl] -memyl] - benzamide, 2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole, 2 - [(l-methylethyl) sulfonyl] -5- (trichloromethyl) - 1, 3,4-thiadiazole, 2- [[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] - amino] -4-memoxy-lH-pyrrolo [2,3-d] pyrimidine-5- carbonitrile, 2-aminobutane, 2-bromo

2- (bromomethyl) pentandinitrile, 2-chloro-N- (2,3-dihydro-1, 1, 3-trimethyl-lH-inden-4-yl) - 3-pyridinecarboxamide, 2-CWor-N- (2nd , 6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide, 2-phenylphenol (OPP), 3, 4-dichloro-1 - [4- (difluoromethoxy) phenyl] - 1 H-pyrrole-2,5-dione, 3,5-dichloro-N- [cyan [(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) -IH-imidazole-1 -sulfonamide, 4-methyl-tetrazolo [1, 5-a] quinazoline -5 (4H) -on, 8- (l, 1-dimethylethyl) -N-ethyl-N-propyl-l, 4-dioxaspiro [4.5] decane-2-methanamine, 8-

Hydroxyquinoline sulfate, 9H-xanthene-9-carboxylic acid 2- [henyla-mino) carbonyl] hydrazide, bis- (l-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, 1 - Dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethyl-mo holin hydrochloride, ethyl - [(4-chlorophenyl) azo] cyanoacetate, potassium hydrogen carbonate, methane tetrathiol sodium salt, methyl 1 - (2,3 - dihydro-2,2-dimethyl-1 H-inden-1-yl) - 1 H -imidazole-5-carboxylate, methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate , Methyl-N- (cMoracetyl) -N- (2,6-dimemylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide, N- (2,6- Dimethylphenyl) -2- memoxy-N- (tetr-ydro-2-oxo-3-furanyl) acetamide, N- (2,6-dimethylphenyl) -2- memoxy-N- (tetrahydro-2-oxo-3- thienyl) -acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) - 1,4,5, 6-tetrahydro-2-pyrimidinamine, N - (4-Hexylph enyl) -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-TricMor-l - [(cUoracetyl) amino] ethyl] - benzamide, N- [3-Cωor-4,5- bis- (2-propynyloxy) phenyl] -N'-memoxy-me an-in-ύdaιnid, N-formyl-N-hydroxy-DL-alanine sodium salt, O, O-diemyl- [2- (dipropylamino) - 2-oxoethylj-ethyl phosphoramidothioate, O-methyl-S-phenyl- phenylpropylphosphoramidothioate, S-methyl-1, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] - 1-benzopyran-2, r (3'H) -isobenzofuran] -3 '-one.

bactericides:

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

Insecticides / acaricides / nematicides:

Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bifuthrin, Bensulhrin, Bensultaphr, Bensultap. Brofenprox, Bromophos A, Bufencarb,

Buprofezin, Butocarboxim, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifoshrin, Clopyrinoshrin, Clofifin, Cypyrifin, Clofyrin, Clofyrin, Clofifin, Cyrofyrin, Chlorpyrin, Clofifin, Cyrpyrin, Clofifin, Cyrpyrin, Clofifin, Cyrpyrenthrin, Clpyrifosin Cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, deltamethrin,

Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton, Edifenphos, Emamxatin, Ethofencarbin Ethoprophos, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb,

Fenoxycarb, fenpropathrin, fenpyrad, fenpyroximat, fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinat, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathlocophosidone, iphaflophosphidone, ICH Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,

Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NT 25, Nitenpyram, Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Permethron, Phathoatophon, Phenthoat , Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur,

Prothiofos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, RH 5992, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Spinosad, Tebufenpiridosin, Tebufenpyridos, Tebufenpyridos, Tebufenpiridos , Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin,

Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Thiamethoxam, Namidothion, XMC, Xylylcarb, YI 5301/5302, Zetamethrin.

A mixture with other known active ingredients, such as herbicides or with

Fertilizers and growth regulators are possible.

When used as insecticides and nematicides, 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.

At appropriate application rates, the compounds according to the invention also show herbicidal properties or plant growth-regulating activity, such as a defoliant effect.

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 and 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 ., 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, for example 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) 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, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Hamsters, guinea pigs, rats and

Infest mice. By combating these arthropods, deaths and reduced performance (in 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, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal

Application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags , Limb straps, holsters, marking devices etc.

When used for cattle, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.

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

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

Beetle like

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

Hymenoptera such as 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 saccarina.

In the present context, technical materials are understood to mean non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.

The material to be protected against insect infestation is very particularly preferably 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: timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors , Plywood, chipboard, carpentry or wood products that are used in general in house construction or joinery.

The active 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, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellants, if appropriate siccatives and UV stabilizers and the like - if 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 are advantageous from 250 to 350 ° C, petroleum or aromatics from the boiling range of 160 to 280 ° C, turpentine oil and the like.

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 spindle oil and / or monochloronaphthalene, preferably α-monochloronaphthalene, 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 is also a Evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced. 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 known organic-chemical binders are the water-thinnable 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, for example 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.

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-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be 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 with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.

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 polyvinyl methyl ether or ketones such as benzophenone and 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 particularly suitable as additional mixing partners. The compounds mentioned in this document are an integral part of the present application.

Particularly preferred mixing partners can be insecticides, such as chlorpyriphos,

Phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, as well as fungicides such as epoxyconazole, hexaconazole, azazonazole, propaconazole, propaconazole, propaconazole, propaconazole, propaconazole, propaconazole, propaconazole, propaconazole, propacone azole -Iod-2-propynyl-butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octyl-isothiazolin-3-one.

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 biological breeding methods, such as crossing or protoplast fusion, are 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 (Genetically Modified Organisms) and their parts. 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 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, 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, which go beyond the effects to be expected.

The preferred transgenic 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 drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher harvest 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. 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) are mentioned, whereby maize, soybeans, potatoes, cotton and rapeseed are particularly emphasized. 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

Bacillus thuringiensis (e.g. by the genes CryΙA (a), CryΙA (b), CryΙA (c), CryllA, CrylflA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants (hereinafter "Bt plants" ). The properties ("traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR),

Systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins. The traits are also particularly emphasized the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylans, glyphosate or phosphinotricin (e.g. "PAT" gene). Each of the desired properties

Genes conferring ("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 that are sold 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) are sold. Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are marketed under the trade names Roundup Ready ^® (tolerance to glyphosates, e.g. maize, cotton, soy), Liberty Link ^® (tolerance to phosphinotricin, e.g. rape), EMI ^® (tolerance to Imidazolinone) and STS ^® (tolerance to sulfonylureas eg

Maize). As a herbicide resistant (conventional herbicide- Plants cultivated with tolerance should also be mentioned 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 treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention. 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 plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mite 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 and 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 as well

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., Phüipomyia 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) 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 preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples

Example 1 (Method (a ¹ ))

N'-cyano-N-π - (2.4-dichlorophenyl ethyl1propanimidamide (intermediate of formula (V))

1.85 g of l- (2,4-dichlorophenyl) ethylamine, 1.63 g of trimethyl orthopropionate and 0.46 g of cyanamide were heated under reflux for about 30 minutes. After the volatile components had been removed under reduced pressure, the residue was stirred with water. After filtration and drying, 2.22 g of N'-cyano-N- [l- (2,4-dichlorophenyl) ethyl] propanimidamide remained with a logP of 2.56.

Example 2 (Nerfahren (b))

Ν'-Cvano-Ν-ri-f∑ -dichlorpheny ethyl-Ν-methylpropanimidamide

1.00 g of N'-cyano-N- [1- (2,4-dichlorophenyl) ethyl] propanimidamide was added in 25 ml

Dissolved dimethylformamide and 0.16 g of sodium hydride (60% in paraffin oil) was added at room temperature. After 30 minutes, 0.63 g of iodoethane was added. The mixture was stirred at room temperature overnight and, after removal of the solvent, purified by chromatography. This left 0.86 g of N'- Cyano-N- [1- (2,4-dichlorophenyl) ethyl] -N-methylpropanimidamide with a logP of 2.80 and an mp of 148 ° C.

Analogously to Examples 1 and 2 and in accordance with the general description of the production processes according to the invention, for example the compounds of the general formula (I) listed in Table 1 below can also be prepared.

Table 1

Expl Connection of physical data

10 logP: 2.55

11 logP: 2.55

12 logP: 2.59

13 logP: 2.59

14 logP: 2.68

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C. Eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms), the logP values of which are known (determination of the logP values on the basis of the

Retention times by linear interpolation between two consecutive alkanones).

applications

Example A

Meloidogyne Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

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

Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva 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% means that the number of galls on the treated plants corresponds to that of the untreated control.

In this test, for example, the following compounds of the preparation examples show good activity: 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 17, 18, 19, 20, 22, 23 , 24, 25, 26, 27, 28, 29. Compared to the prior art, the compounds according to the invention in the test described above show a clear superiority in terms of their effectiveness at a given active ingredient concentration in ppm (cf. Table II). The effectiveness of the compounds is given as a kill in%.

Example B

Spodoptera frugiperda test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts 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.

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.

Production examples 5, 9 and 19 show good activity in this test.

Example C

Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkyl 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, e.g. the following compounds of the preparation examples have good activity: 19.

Claims

claims

Compounds of formula (I)

in which

n represents 2, 3, 4 or 5,

R represents C 1 -C ₄ -alkyl optionally substituted by halogen, and

X represents halogen, where the different substituents X can each be the same or different.

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

in which

X and n have the meanings given in claim 1, (a) with compounds of the formula (ϊϊl)

in which

R has the meaning given in claim 1,

Q stands for oxygen or sulfur and

Y represents alkyl,

or

with compounds of the formula (IN)

in which

R has the meaning given in claim 1, and

Y represents alkyl,

and cyanamide,

optionally in the presence of a diluent,

and (b) then alkylated by following the procedure described in. Process (a) or (a ') resulting compounds of the formula (V)

in which

R, X and n have the meanings given in claim 1,

with compounds of the formula (VI)

CH ₃ -Z (VI) in which

Z represents a leaving group,

implements.

3. Nerfahren for producing compounds of formula (I) according to claim 1, characterized in that compounds of formula (VII)

in which X and n have the meanings given in claim 1,

with compounds of the formula (III) according to process (a) according to claim 2,

or with compounds of the formula (TV) according to process (a ') according to claim 2.

4. Compounds of formula (I) according to claim 1, characterized in that

n represents 2, 3 or 4,

R represents methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine or bromine, and

X represents fluorine, chlorine or bromine.

5. Compounds of formula (I) according to claim 1, characterized in that

n represents 2 or 3,

R represents methyl, ethyl or n- or i-propyl optionally substituted by fluorine or chlorine, and

X represents fluorine or chlorine.

6. Compounds of formula (I) according to claim 1, characterized in that

R represents methyl or ethyl.

7. pesticide, characterized by the content of at least one compound of the formula (I) according to claim 1.

8. Use of compounds of formula (I) according to claim 1 for

Pest control.

9. A method for controlling pests, characterized in that compounds of the formula (I) according to Claim 1 or agents according to Claim 7 are allowed to act on pests and / or their habitat.

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